Female prisoner’s boyfriend

Female prisoner’s boyfriend

A fantasy of women using a man

Part one Getting in.


Bob was an eighteen-year-old student nervous and unsure of women when he met Sara. She picked him up in a bar and took him to her flat for sex. Sara was slim blonde attractive with long legs and pert boobs and eighteen. She was not a student and Bob was not able to find out what she did but she always seemed to have a lot of money. The sex was wild for Bob with Sara definitely the one in control. Sara demanded from Bob a lot of cunnilingus and sex usually with her on top. The fact that Bob when exhausted stayed hard pleased her. Soon Bob was seeing Sara three or four times a week for the night and wild sex and by the end of the month he was sure he was in love with her. As for Sara she was a lot cooler but enjoyed the sex with him and dominating him to her pleasure and several times when he lay moaning sore and exhausted she told him it was his wooden delight that made her see him.

Then one night he went to her flat and found it sealed up with police tape. Confused and worried he phoned the police station and was ordered to come and talk to them. Instead of a night of wild passion Bob spent two hours being questioned by a policeman about Sara. He was told Sara had been charged with drug and firearm offences as well as three attempted murders and GBH. Bob was horrified and went home in a daze. He tried to forget Sara but could not and three days latter he got a letter from her admitting to some of the crimes but telling him how marvellous he was. For three weeks they corresponded and by the end Bob was back in love with her. Bob went to the court to see her first trial and was very surprised when she was only charged with the firearm and drug offences and the other charges were dropped. Even odder she pleaded guilty. Sara then saw Bob and gave him a big smile and a wave before the judge moved to sentence her again it was odd to be doing this so quickly. In fact Bob guessed correctly that Sara had struck a deal with the police. The judge told Sara that if she had contested the charges and not fully admitted her crimes she would have faced a twenty-year term. However he told her as she had recognised her guilt he was instead going to sentence her to six years with parole available after three years. Bob groaned at that but Sara seemed quite pleased and gave Bob a wave and blew him a kiss as she was taken down.

It was three days before Bob got a letter and Sara told him she was in a prison for young adult offenders where she could expect to serve the whole three years and unless she committed a major offence she would not go to an adult prison. She also told Bob that if she had not fully confessed and given the police the dirt on a few of her associates she would have gone down for a life sentence and served at least fifteen. They carried on writing and after two weeks Bob went to see her in prison. It was a train ride and then a bus to the prison that was right out in the country. An earth bank with a tall wire fence surrounded the prison and when the guards let Bob and about eight more people in he saw inside fields and then three dull concrete buildings. A large ugly middle aged female guard escorted them across and then into a small building next to the main ones and told them to sit and then a group of female prisoners came in. All were wearing T-shirts and skirts in grey. Then Sara saw Bob and moved quickly over and gave him a long kiss before the prison officer coughed and she let him go. They chatted and Sara told him the jail had in it about one hundred and twenty girls aged from seventeen to twenty two mainly doing six to twelve months here for drug offences and with three years to do Sara was serving about the most. Sara told her the girls were usually celled in pairs and that the work was dull and monotonous. In fact boredom was the biggest bad thing about being inside she told him apart from and at this she gave his hand a sexy rub the lack of sex. Then her foot moved and under the table she started to rub his groin with her bare foot bringing him to erection. She told him many of the girls played around with lesbian affairs to have something to do. As for the guards they were mainly female and quite a few were genuine lesbians. It seemed grim and Sara told him the nights were the worse as lock down was at eight and on Sunday due to lack of staff they were frequently in the cells all day. All the time she was rubbing his groin getting him close to orgasm but frustratingly he knew he would not get off. Then the time was up and Bob left Sara with cigarettes for trading and a mass of sweets.

They carried on writing and Sara wrote Bob some very erotic letters. Bob replied and kind and soon they had agreed to masturbate alone in their own beds every other night at ten thinking of the other person. It was a month before he was able to see her again and again she rubbed his groin with her foot under the table. She told him she was bored to death by the prison and had twice got solitary for fighting with other girls more as something to do. Bob urged her to hold on and she told him she was sure he would drop her but he assured her he would not do so. Again he left her with cigarettes and sweets. By now it was summer and Bob went to stay with his mother and stepfather. However when they discovered he had a girlfriend in prison a major row developed and Bob moved out. Sara was sympathetic to Bob who was now staying above the bar he was now working in. Their letters were always erotic but the only thing was Sara never really responded to Bob's comments about living together when she got out. When he saw her next she seemed depressed and while she again rubbed him with her foot to tease him she told him the lack of a man was driving her mad. She told him that the girls were not allowed dildos or vibrators and her fingers did not feel as good as his dick or his tongue.

Bob was full of sympathy and lust and looked at the guards who was watching the prisoners and their visitors and told Sara nothing could happen. Sara then asked did he love her and he assured her he did. Then she gave a smile and told him that maybe something could happen if he really did want her and was brave. He told her he was and she told him that her cellmate was being released this week and that she was extremely friendly with one of the girls who worked in the file section. Bob looked confused and Sara told him he looked quite feminine even though she knew he was male though and though and for example he only had to shave about once a week. Bob nodded as Sara smiled and said he could pose as a prisoner. Bob laughed and told her it was never work and she smiled and told him she had worked out it would. The problem she said was to get him in as all visitors were carefully checked however Fridays were rubbish days. The rubbish was placed by the third building and a gate left open to the building to allow the van to get in. Bob would have to do was sneak in and hide and then in the afternoon the gate was closed and the girls made to clear the area up. Sara told Bob this was how loads of stuff got smuggled in but no one had tried it with a boyfriend before. Sara's friend would then add a prisoner to the role for six weeks the minimum time a prisoner served and after that he would be released. Bob was amazed and realised this could work. Sara smiled and begged him and Bob had no way to refuse. The idea of spending the summer with his girlfriend excited him and Bob did not think about the dangers of being in a girl's prison.

Therefore they agreed to do it next week as first Sara needed his fingerprints and a photo of him looking as feminine as possible. She told him not to worry as some of the girls were very odd looking but to remember to bring his shaver. That night Bob wrote to her and hide in the letter his fingerprints as for a picture he took one of his face in a mirror with him wearing a girls scarf he had found in the bar and also with some make up on he had brought in the train station. Sara wrote back and told him that was perfect and then told him what to bring with him. Apart from his shaver and a spare she wanted him to bring in female underwear in white to fit him including bras and Sara suggested Bob became a B cup. For the bras she told him to get some silicon false breasts to go in them and suggested he got them for a transvestite clothing company and gave him its address. As well as that she told him to get a girls T-shirt, jumper and a skirt that would be his release clothing. Then there was a load of make up so Sara could disguise his male face and female deodorants for his male smell. Then she told him to bring in loads of cigarettes for them to trade but also as much vodka as he could carry and at least six bottles. Bob got all the stuff finding it embarrassing to get female underwear and as for the silicon false boobs that was very difficult as the woman when he phoned up to order them assumed he was a transvestite. One night he tried on the female underwear and boobs and found the whole affect very disturbing. The false boobs looked good in the bra and were stuck onto his skin by glue and he knew would fool someone unless he was fully investigated. Then as instructed by Sara he shaved his legs and armpits to make him look more feminine. The next day he left the bar and his boss gave him a dozen vodkas as a leaving bonus. Bob got the train and bus to the prison as he had arranged with Sara and then as she had instructed dressed as a man he walked to the back of the prison.

Just as Sara had said the gate was open and Bob quickly sneaked in. As Sara had said in her letter their was a pile of plastic bin bags and next to them a shed full of wood. Bob went in and closed the door and then as Sara had told him he hid behind the wood. For two hours nothing happened and then there was a load of noise and Bob looked out and saw the dustbin men removing the rubbish. As soon as they had gone Bob stripped as Sara had told him and then put on the female clothing including the bra and silicon boobs and placed the male clothing in a plastic bag. Then it went quiet for another tedious hour until Bob heard a noise and two prison officers came out locking doors. They were obviously doing a check but did not really bother much to Bob's relief. Then they locked the gate and suddenly Bob felt sick as he knew he was trapped in the female prison and he realised he should have checked the penalty for breaking in to a prison.

Then the prison officers opened a gate and a party of girls came out looking totally bored and were set to work picking up bits of rubbish and also sweeping the yard. Bob peeped out and saw Sara with a broom and a bag. For thirty minutes Sara swept and then when she saw no officer was looking she quickly undid the storeroom and went in. When she saw Bob her face lit up with a big smile and she moved over and kissed him hard for a couple of minutes. Then she broke off and said, “You look like a girl admittedly a very ugly girl but a girl! Nice tits as well! God you are clever! Okay you are Bobbie Bailey new here today! Now put these on instead of the civvy stuff!" And with that Sara pulled off a T-shirt and a skirt and Bob saw she was wearing two sets. Bob stripped but as soon as he was in the female underwear Sara grabbed him and groped his groin and his dick got erect in the panties. Sara said, "Take these off and lie down! It will only take thirty seconds for me to come!" Bob nodded and pulled them down but before he could get them off Sara had him on the ground and she raised her skirt and tugged her panties to one side and engulfed him her pussy sodden. In less than twenty seconds Sara screamed in orgasm and Bob blew powerfully into her lost by the power of her orgasm. Immediately Sara pulled off and said, "Christ I needed that! Okay get dressed, as a prisoner and I will get rid of the male stuff!" and before Bob could react she had dumped all his male clothing in a bin bag. Then Sara saw the cigarettes and vodka and smiled and said, "Great a dozen bottles! Six pays for no girl mentioning the number in the party and six more for us! Bloody hell I have missed alcohol nearly as much I have missed cock!" Bob nodded and dressed and then Sara checked his make up and then placed the vodka, cigarettes and Bob's things in two more bin bags leaving six bottle of vodka out.

They waited inside for ten minutes and then one of the prison officers blew a whistle and Sara said, "Here goes! I feel really nervous! Okay act cool and female but mainly act totally bored. And follow me I will lead you to our cell!" Bob followed her out feeling terrified. Outside stood a tough looking chunky blonde who gave Bob a leer and then smiled as Sara pointed out the bottles of vodka and said, "For you Charlie! You saw nothing!" and the tough girl nodded. Then Sara threw Bob's clothing onto a pile of other bin bags and pushed the now frightened boy along both holding a bag of contraband. As she did so Bob suddenly realised that apart from her letters he did not know much about Sara apart from the fact she was a violent criminal and sexually dominant. He also wondered what would happen to him if he were found out and also what the next few weeks would bring.

Part two Inside the cell.

Sara pushed Bob along and though a door followed by a couple more very bored looking girls. Inside was a room and a guard another massive middle aged ugly woman who asked if all the girls were here and Charlie replied yes so she unlocked a door and ordered them to follow her. They walked along a dull corridor and then though at least three more gates and Bob felt more and more worried and depressed. Then they arrived at a canteen not that there was any space to sit. The girls lined up and each was handed their supper on a tray to carry and eat in their cells. Bob staggered along finding it hard to hold the tray and the bin bag of contraband and was amazed no one had searched the bags. They were let into the cellblock and it was on two floors with an enclosed recreation area in the middle and six cells on both sides a total of twenty-four cells holding over forty girls. However the girls and Bob were urged to their cells. Sara's cell was on the second floor and as soon as they were in Sara pushed the bag under a bed and grabbed Bob's and did the same. The cell was painted pink but looked bleak with a barred window and two single beds on either side and at the back of the cell up against the beds and toilet and a sink. The light was recessed into the ceiling and covered with wire as well. Apart from the beds there was no where else to sit. Sara smiled and said, "Welcome to our new home honey! When you said you wanted us to live together I bet it was not here!" Bob went to reply but a large female guard interrupted and glared at Bob and said, "There you are you stupid girl! You had to wait here and not go off and work you silly slut! Okay get used to it Bobbie it is lock down time!" and she slammed the door. Sara smiled and said, “We are lucky they have a few staff off so we get locked down as soon as we have finished work! Usually I hate that but tonight that is great! Okay eat up honey and then we can chat and god make love!" Bob nodded feeling to nervous to eat and the state of the tepid food did not make him hungry. However Sara ate all he did not want and then said, "Okay it cost six vodkas to get you in! And a hundred fags for the clothing and bedding! Now I know you are a man and so do Charlie and Maxine my friend with the cushy office job! And those two are powerful girls in here baby! No one else does and they must not suspect! If we get caught then I lose nine months parole and get transferred to the adult prison and I do fancy serving the butch lesbians in there! As for you well if the authorities get hold of you then you will get at least five years for being here! And for making them look stupid they will make it tough and put you somewhere where you will quickly get gang raped and lose your parole as well!" Bob gasped and said, "five years!" "Yes it is a criminal offence to be here remember what you signed when you visited me!" and Bob recalled signing a paper on every visit about what he could do on a visit and it being a criminal offence if he did not. Sara gave Bob a smile and said, "However honey if some of the girls find out you are here you will be gang raped to death here until you cannot perform and then they will chop off your cock and balls! Oh do not panic I am sure no one will find out so long as you are careful!" "What do you mean?" "Okay always act like a girl! You only wash here and use the loo like a chick okay! Never get naked keep the panties on and the bra and boobs on at all times! Your voice is a bit deep but no one will notice. Wear the make up and shave every morning! Remember no one will believe you could get a guy in here least of all the screws!"

Bob nodded at that and felt a little better. Then Sara smiled and said, “As for sex well honey you and I will make out every night after lights out and my god I need to be fucked! As for the others well Maxine will want to be laid and so will Charlie!" Bob moaned and looked surprised as Sara smiled and said, "Oh yes I told you that you would have to be brave well giving girls sex is part of that! Now Charlie and Maxine will get cock and maybe a few more trusted girls will as well but that is not all!" "What do you mean?" "Well in here either you are a tough girl or you lick pussy! Well I am the tough girl okay and you are my honey bitch! Well honey bitches lick pussy! Do not worry they will not know you are a man because the honey bitch gets nothing back! So Bob I am afraid you will get quite a few pussies to lick off! Still you have always told me you love to give head so that will not be a big problem for you!" Bob looked dazed and said, "They will know!" "No they will not as sex here is an offence and costs an officer their job and a prisoner two weeks parole and three days solitary so sex is rushed and fast and clothing is only removed to allow access! You will stay dressed and the girl will get her knickers off and you will get under the skirt and satisfy her! They will think you are a girl! I will put the word around that you belong to me and that I am the only one allowed to touch your pussy and bare tits! I will tell the girls I am keeping you unsatisfied to keep you keen! You will not be the only one there is a girl on A wing whose owner has not let come for over a year poor cow! Now remember you are a girl or we both get raped! Now let’s sort out the loot!"

Bob was dazed and confused as Sara pulled the bags out and said, "You did well!" "Thanks but I am amazed we were not searched surely the officer saw the bags!" "True she did but Miss Town is an easy officer to pay off! Charlie told her they had alcohol in and offered her a pay off! One for you I am afraid to say!" "What?" “Well Miss Town is a lesbian! She likes to make girls go down on her and picks on the new girls! She only likes a girl to do her once but likes to do as many as possible! Well Charlie told her you would do her if she turned a blind eye!" "Oh no!" "Oh yes we needed that! It will be easy she come fast if a little wetly and her muff does not smell that bad! And the big joke is she hates men and would be sick if she thought a male was doing her!"

Bob felt sick as the truth of his position sunk in. He was trapped with Sara who while beautiful and sexy he was starting to realise was a nasty girl interested in her own pleasure and willing to use him to satisfy her. He realised from her conversation that Sara was mixed up in quite a lot of nasty dealing inside and maybe the two fights had not been the other prisoners fault but Sara. And also maybe the police officer had been telling the truth about Sara shooting a man in the groin in cold blood for repudiating on a drug deal. Then Sara deliberately took off her top and then her bra so her pert high breasts were free. She smiled and said, “I am hot and what is wrong with a girl being topless with another girl? Nothing unless it gives the girl a massive hard on! Shame you had better stay fully dressed Bob and I had better get used to calling you Bobbie! Do not worry the next few weeks will be fun and a real education for you! After all how many men get to live as a girl! Now I am going to wash my tits and you can watch and think sexy thoughts about lights out! God I cannot wait I think I will screw you all night long!" Then Sara picked up a flannel and seductively wiped her breasts. Bob watched spell bound aware that he was erect and while he felt sick by what Sara had said and was now terrified about being found out and also by what would happen to him as Sara's girl he knew he wanted to be Sara's man and knew that until she was released this was the only way he could get near to her.

It took Sara twenty minutes to massage her breasts clean and all the time Bob was hard. Then topless Sara picked up a book and said, “We get a book a week and no real choice! And we are locked inside for bloody hours! God it is so boring here! Still now I have you and the cows do not know! Okay you can read this one it is crap but the only thing here and this one is no better!" And she threw a romantic novel to Bob and then lay back on her bed to read. Bob had to do the same feeling dazed and sick. He read looking occasionally at the topless Sara who smiled every time she saw him looking. He knew he loved her and hoped she loved him but a large part of him suspected she had gone with him because she liked to be the boss. Then after her arrest he had stayed with her and this had suited her. As for her getting him in he was sure she had done that not for love of him but because of her total boredom with the prison and as a way of showing her power over the world. Then Sara smiled at him and cupped her breasts and said, “Do you remember writing about us living together when I get out? Well if you are a good boy with me in here we will! Do you think you would like owning these?" Bob gasped at that and was totally confused and then believed it was a test of his love. He replied, “But Sara you are always the boss and I do not think your breasts will belong to any one apart from you!" Sara laughed and said, “Very true! So let’s enjoy this adventure okay!" And the much happier boy nodded as Sara smiled at him. Another hour passed and then Bob needed to use the loo. He stood and walked over and Sara said, “As a girl dear!" And Bob blushed and sat on the loo Sara looked at him and said, “Keep the skirt covering you so anyone looking in cannot see your cock! I tell you Bob sorry Bobbie in this cell we will have no secrets from each other!" Bob nodded as he finished and returned to the bed and then Sara used the loo but see deliberately raised her skirt so Bob could see her doing it.

Then after thirty minutes the light flashed and Sara said, “Five minutes and then they turn the power off! Okay lets get into bed and give it five minutes and then we can fuck! Keep the T shirt and knickers on honey bun!" And with that Sara stripped naked and got into her bed. Bob did the same and then the light went out. As soon as it was out Sara moved and got into the bed and said, "Privacy! Just you an me together baby until the morning! Now let me have a look at your tits!" Sara tugged at the silicon boobs on Bob's chest and smiled as he moaned and said, “They look okay but feel odd! Cold and dead! They are well stuck on honey though and should only need regluing every week or so! Very nice but it is not your tits I want but your tongue and cock! Okay get under the sheets baby and kiss pussy hello again!" and roughly she pushed Bob underneath the sheets. Bob wiggled down until his head was between her slim thighs and then Sara grabbed his hair and steered him onto her already wet pussy. Bob gagged at the smell as he was used to a freshly showered Sara. Her pussy smelt very unwashed as indeed it was and Bob groaned as he recalled the lack of toilet paper in the cell and latter he discovered the girls were rationed to thirty sheets of hard waxed paper a week. Of course earlier he had come into her and he was able to taste his come solidified on her pubic hair as he licked away. Not that Sara cared as she pushed him in and moaned and he knew she was still terribly excited. He licked away and soon her fresh juices were filling his mouth replacing her stale taste. In less than two minutes Sara's moans rose and she came thrusting with her hips his mouth hard onto her pussy. She pulled him up and placed him on his back and said, “I want to kiss you! You can come if you like but you eat the come and keep it up because I am going to ride you until your knob falls off!" And with that she went under the sheet. Sara pulled his panties off and then wrapped a warm hand around his already erect dick. Then Bob groaned as her warm lips enclosed his dick and moaned again as he felt her tongue slip around the head. Sara started to lick and suck him making Bob moan and groan as his excitement rose. He did not really want to come so early in what he knew was going to be a long night of lovemaking as he knew latter on when Sara had reduced him to an exhausted wreak how painful her lovemaking could be but he could not resist her active warm mouth and came spurting into her mouth as her tongue lapped at the head of his dick.

Sara moved up and grabbed Bob and then kissed him forcing his come deep into his mouth and making him swallow. The first time she had done this Bob had been shocked but now he knew that this was the price you paid for a blowjob from Sara. Sara stopped kissing him and said, “Head again but this time me on top and then honey cock in cunt time!" And she moved up and sat herself on his face and once more Bob gave her oral pleasure. As he did so Sara placed his hands on her pert breasts and he rubbed her large erect nipples as she rode his face. This time it took the excited girl nearly five minutes to come moaning as she did so. As soon as she had come Sara moved and wiggled down and once more grabbed Bob's dick. It was semi hard but quickly her hand had him fully erect and then Sara eased him into her wet passage the excitement making both groan. Then Sara started to flex her hips as powerfully she rode him. By now Sara was so hot that sweat dripped off her face and onto Bob. He did not mind but moaned himself and started to rub her boobs again increasing the girl's excitement. Bob was amazed when in less than two minutes Sara came on him. After her orgasm Sara stopped and said, “I feel like a right nymphomaniac but three months without cock is too much! Still no problem now baby so let's do it again and then again!" Bob nodded to dazed and excited to resist as the beautiful girl again rode him. This time it took Sara longer to come and as she rode him his excitement rose as well. Sara noticed this and urged him to hold on for her and Bob just managed this but when she sat upright on him in orgasmic delight and buried his dick as deep as possible in her pussy he had a tremendously powerful orgasm and the world spun.

Bob lay dazed and exhausted and knew now all he wanted was sleep as the events of the day hit him. Not so Sara, who wiggled up him and plonked her pussy on his face and said, “Lick this clean baby! After all we do not want come stains on the sheets! And while you do that I will get your stick back in action!" Bob licked her pussy as Sara moaned on him and then Sara turned and lent and took Bob into her mouth and used her warm mouth and active tongue to get him hard. By then she was close again and broke off and once more rode Bob's face and tongue until she had reached orgasm. Then she took control of the exhausted boy's dick her hips flexing and her pert boobs rippling in the moon light as she enjoyed him. Three times Sara came on Bob and then he lost it again shuddering as her tight pussy milked the come from his dick. Bob would have passed out but Sara shook him and then got on his face and tugged at his hair until somehow he got his tongue active. He did not really lick her off rather he let her use his stuck out tongue but it was enough for the sex-crazed girl. Then Sara used her mouth to get him hard if wooden and sore and once more she engulfed him for her pleasure. Bob was unsure for how long she rode him but it was well over an hour and at least six strong orgasms for Sara before he spurted. As he was so tired his orgasm gave him little pleasure and a lot of pain in the testicles. Again he wanted to pass out and again Sara used her hands to pinch him awake and then abused his tongue as her hands and mouth forced him to stay erect. Then she ravished him once more and all Bob could do was lay there dazed and in pain as her pussy rasped his red sore dick. Bob had no idea of the passing time as Sara came and then came again. Each orgasm was taking her longer as finally she became sated but the power of each orgasm was increasing. Then suddenly without pleasure but with the feeling that his testicles had been set on fire Bob came and passed out sobbing in agony. However he was dimly aware of staying hard and suffering under his amazon mistress for a lot longer.

Part three Inside the prison

Bob was woken up by Sara pinching his balls and groaned as she did so. Sara smiled and said, “Less than an hour before we get up sleepy head! Last night was great but my cunt needs a morning clean so get licking!" and with that she sat herself on the dazed boy's head. Bob had no choice but to lick her matted pussy clean and then bring her moaning to orgasm. Sara then got off and said, “Okay baby get washed and shaved and let me put a bit of make up on you!" Bob did so as embarrassed about using the toilet in front of her and then as he quickly shaved Sara stood in front of the door to block the view. Then she applied a little make up and did his hair before she checked his clothing. Bob felt odd in the bra and girls panties but the skirt was worse as the air moved underneath it in a very strange manner. However Sara was satisfied and said, "You look like a girl baby! Tits as tits small but wobbly! And my muff well last night was great I must have spent nearly two hours on you after you passed out honey! My last one! Wow! An hour to get there I reckon and I came for ages when I did! I do not think I would ever want sex again but this morning I had to get head off you and tonight well let’s say encore!" Bob nodded remembering how exhausting Sara was sexily. On the outside her nymphomaniac tendencies had excited him as he had been able to get nights to recover but locked into a small cell with her he knew she was going to screw him until he could not move every night and he groaned at that as he felt the emptiness of his balls and the soreness of his dick. Indeed as he moved the sensation of the very tight panties on his tender groin made him want to weep with pain.

Sara took his mind right off the pain by saying, “Okay time for work and also a few pay backs! You get to meet all the girls so remember you are female or they will castrate you! As for the work we are on the cleaning crew dull and dirty work. Still as a honey bitch you will get the easier but most boring work to do. In fact I think Charlie has set you up for washing and ironing with the other sad pussy lickers! No one will think you over odd there! Remember you love being my honey bitch and love my pussy and boobs! That at least is true! Okay here we go!” And as she spoke the door was unlocked.

Bob was surprised to see it was a male prison officer. The man was fat bald and middle aged and leered at Bob and Sara and said, “Time to stop your lesbian games whores and get out and do some work!” Bob blushed at that but followed Sara out. As they walked she said, “Mr Lloyd a right bastard! Still the girls keep him under some control by giving the bastard blowjobs! Apparently his cock is small and smelly not that I have had to lick it! I told the cunt where to go when he tried it on! The other screws on the wing are Mr Reeve he is okay but likes a blowjob if he thinks he can get one! And Miss Smith and Miss Callow both right bitches! Still all four are easy to corrupt for money or sex! We have no money so honey you will have to say hellos to bitch Smith and Callow’s cunts! Not today honey bun do not worry yet but soon I suspect they will make a move! After all the two ladies expect a girl to share her honey bitch! As for the men or rather bastards they only try it on with girls who let them so you should be safe from them! Do you know some of the girls are so desperate to see a cock they go down on their knees for those two just to taste come! So be careful baby because your sweet cock would be heaven for some of our cock crazy girls! Now say hello to the other girls and remember you are Bobbie my honey bitch! Hi girls say hello to my dear friend Bobbie”

Bob moaned as a group of about ten girls turned and smiled at him. He blushed as he felt their eyes appraising him. However most gave him a weak smile and he realised that his disguise as a girl had fooled them. The only one to leer at him was the tough looking chunky blonde Charlie. Bob gulped at that as he saw she was a muscular girl with big strong thighs and large boobs in her T shirt. Her hair was cut in a short mannish style and her face was flat and unattractive. She smiled at Sara and said, “Nice honey you own Sara! Heard you picked her up when you were last inside must be nice to have a familiar face on your cunt! And I am sure she will feel nice on mine and the rest of the gang!” Sara smiled and Bob looked horrified and heard some of the girls giggle. Charlie noticed his face and said, “Oh yes baby here you do not just get Sara to satisfy you have a load of girls who like to get off so expect to be on your back with girls on your face all though association! As for me well Sara has agreed we get a nice intimate massage session where I get to tease your cunt bitch! But no orgasms as your mistress has made it clear she is keeping you keen so no one gets your cunt or tits to play with except a few special friends of hers and we will make certain you do not get over wet!” Bob gasped at that and realised that Charlie had made it clear he belonged to Sara’s in front of all the other girls and that as far as they were concerned he was Sara’s female slave being kept in chastity.

Then a female prison officer came over and ordered the girls to follow her. She was middle aged and gigantic with a bottom like an elephants and platform boobs and to Bob’s horror he heard her called Miss Smith by one of the girls. The group followed her out and then Miss Smith turned to Bob and said, “Okay girl you are working on the laundry detail until further notice! Easy work but dull!” Bob was marched with three other girls to a room. Inside were numerous piles of female clothing and several machines as well as sets of ironing boards. Miss Smith said, “Bobbie you get a bag and put it in the washer dryer and while it is doing it you iron the last lot! Two hours a load so you had better iron fast and well! Anything that is torn iron and put to one side and you can then sew it up! You do prisoners shit and also officers clothing! Tear or damage the officers clothing and girl you really suffer some damage! One month’s parole off and a week in solitary and also bitch my truncheon right up your cunt!” Bob moaned at her aggression making her smile and say,”Weak little girl aren’t you Bobbie! No wonder Sara owns your face! Or at least thinks she does because you are on my wing and do as I say! Right here is a load done before you put this lot in and then get ironing and stop standing around you lazy whores you have work to do you slut cows!”

Bob was horrified by Miss Smith’s language and aggression as the girls set to work. Bob put into one of the large machines a mass of skirts and panties the female smell from them hitting him as he did so. Then one of the girls spoke to him. She was a skinny blonde with small boobs and a tired face who said, “Welcome to the wash crew Bobbie! The dullest job here and one reserved for the weak girls who get on their backs! My name is Linda and I serve Nicola. A much nicer mistress than Sara I have to say. Nicola does not share me around to much and is nice to me in bed. She makes me come and also makes me finger myself off for her! More than Sara is doing for you! She has made it clear that any girl who puts her hand in your knickers to get you off or in your bra gets bottled and as Sara is a real nasty bitch with a broken bottle no girl is going to risk it! Particularly with Charlie and her crews support. And Sara seems keen to let girls face ride you as much as they want! I would hate that! I am not a lesbian and find licking Nicola bad enough. To be made to go down on any girl or woman well yuk! The worse thing I have to do is give screw Reeve the occasional blowjob and at least he is sort of male. However Sara said you are a full lesbian and have no interest in men so I assume giving a woman head is okay for you.”


Bob moaned at that but did not dare deny what Linda had said as he realised that if his cover was blown the least of his immediate problems would be a five year prison term. From the way the girls spoke he knew they would abuse and humiliate him and he had to agree the staff would stand back and let them. Indeed the hideous thought crossed his mind that rather than make a fuss the prison staff would let the girls rape him to death and then just bury him in the grounds. He shuddered at living with such danger for six weeks but knew he was trapped and had no one to save him. Indeed his only chance of survival was to do what Sara demanded and hope somehow he was not found out by the girls or the guards. Then Bob saw the pile of ironing and groaned. It was a mass of female clothing obviously that of a larger lady. Linda smiled and said, “Bad! But you will get used to it! And that bitch Smith was not joking damage a guards clothing and you get it right up the pussy! The last girl who got that punishment was in the clinic for three weeks with vaginal bleeding!” Bob moaned and set to work on a shirt large enough for an elephant and saw the other girls doing the same.

The girls talked a little as they worked and told Bob about life inside the prison from the point of view of those at the bottom. Indeed the only girls below the laundry team were the child sex offenders who were kept away from the rest of the girls and worked on the sewerage system. For girls like Linda the prison was a tough place. She relied on the protection of a tougher girl in her case Nicola in return for sexual services. Everyone knew if you were a tough girl or a honey. A tough girl was a fighter and Bob was told that Sara had put four girls into the clinic after attacking them violently. In two of the fights she had cut the girls up with a bottle and had a reputation as a really nasty girl to cross. Lots of the tough girls banded together into girl gangs with a leader such as Charlie who controlled them. If you were in a gang girls below you in the pecking order went down on you and you went down on girls above you. Sara was a lone tough girl not in a gang but respected by the gangs because of her violence and also her contacts and ability to wheel and deal. About a quarter of the girls were tough girls and a new girl had to fight hard and fast to get a reputation. Most of the girls tried just to keep out of the way and suffered occasional abuse and made payments to the tough girls. However a much smaller group of girls were treated as slaves by the tough girls and these were called the honeys. A honey was a girl who a tough girl wanted and who could not fight or pay her off. A honey belonged to either a girl or to a girl gang and had to give sexual services on demand. As well as to the tough girls these girls also had to serve the female prison staff and frequently the male staff as well. A honey would sometimes be kept for the nearly exclusive use of a girl like Nicola kept Linda or she could suffer a lot worse. A honey could be sold and lent out by her mistress to any other girl without question by the honey. The payment for her services went to the mistress not the honey and was either goods or friendship between the girls. Two tough girls would swap honey’s to show they were friendly as would two gangs to show respect for each other. In fact Linda told Bob that Sara was selling her a lot because she needed as a non gang girl to prop up her position as the guards knew she had assaulted several girls badly and wanted to get her sent up to the adult prison without all her parole. As Sara had to be more careful about fighting selling a honey kept her on top. Bob moaned at that as it all sounded true and he was sure that for all her propositions of love Sara had made the desire to be a top girl was behind getting him in.

Linda then told Bob that when she had first been sent down she had tried to be a top girl but had been beaten up a few times. Then a larger girl had tried to make her her slave and when Linda had resisted attacked her with a bottle. Linda smiled and told Bob she would show her what happened if a girl resisted. Linda raised her top making Bob gasp and then smile as he thought that girls would be like this to each other. Then out of a large plain bra Linda pulled her left breast. The sight of it made Bob gasp as it was covered by thick red scars and bumps and as Bob looked in horror he could make out the outline of a bottle on her flesh. Linda smiled and told Bob the girl had stuck the bottle in her tit and then twisted it. Linda told Bob she had pretended it was an accident but the girl had still lost three months parole and been sent on to the adult prison. Linda had been in the clinic for a month and told Bob that as the prison was so short staffed she had to wait until she got parole in six months time to have plastic surgery and remove the worst of the damage. Bob shuddered at her damaged breast and knew he could not let the girls know he was male as they would surely castrate him.

Linda also told Bob about the staff. The prison was badly understaffed as no one wanted to work in such a lousy place and the officers were the scum of the prison service. Virtually all the female officers were lesbians and they preyed on the girls worse than the top girls. As for the few male staff they were all perverts and all the staff were to some degree corrupt. This made Bob shudder even more as he knew the prison was run by the top girls who were going to use him either as a girl or as a male. Bob questioned about lesbians and was told very few of the girls were real lesbians but did it for something to do and to show position. In fact for over half the girls nothing lesbian ever happened but some embraced the lifestyle fully either by choice or like Linda and the other girls in the laundry room by force. The ironing was taking ages and soon the next load was drying as Bob and the girls ironed in dull tedious near silence. For four hours Bob ironed clothing and by the time it was lunch he had a massive pile still to do. For lunch the prisoners were once more locked in their cells to eat to allow the staff a lunch break. The food was again grim and Bob was locked up with a sweaty Sara. Annoyed he questioned her about the prison and she agreed it was a tough place to be a girl at the bottom. Sara smiled and told him, “You wanted to find out about being a female prisoner and honey you will! As well as serving my sexual needs! And keep quiet about being a man because if the girls find out they will do to your balls what Linda had done to her tit and then hack your cock off! And the screws will let it happen!”

Bob felt like crying as Sara gave a smile and said, “You told me you wanted to live my life so here you are! Not nice is it? Still with you as a honey I get to be a top girl! Now your presence has caused quite a few comments along the girls and a few want paying off so I had better organise some sexual service for you! Or you will get castrated! Now this afternoon you do the educational tests but you are to fail them baby! Then you get some nice lessons! Now as you have finished eating the food you can get on your knees and eat me! It may be a little smelly but I am sure my honey can cope!” Bob groaned but having no choice he got to his knees and pulled Sara’s panties off and applied himself to her musky pussy and soon brought her once more to orgasm.

Part four First afternoon


Bob was sitting red-faced as Sara pulled her panties up and the door was flung open and Miss Smith the massive guard stood there. She leered and said, “Get back to work Sara! Now have you told Bobbie what she has to do? In return for letting you two love birds share a nest I get head of her at least once a week! That had better be okay!” It is!” said Sara as she stood to go and gave the terrified boy a smile and said, “Enjoy Miss Smith’s pussy darling!” Miss Smith gave her a glare as she left and then turned to Bob and said, “That girl is one of the most horrid girls in this jail and we have the scum of scum! Why on earth do you want to be her honey you must be a right masochist lesbian to like her! Okay the price is my pussy so on your knees you daft slut!”

Miss Smith sat on the bed and opened her legs and pulled off a massive pair of white panties. Bob groaned and knelt terrified of what he had to do and what could happen to him if she groped him. Miss Smith raised her skirt and Bob shuddered as her saw her pussy. It was massive and covered in thick black pubic hair. Bob moved closer and her thick musky smell hit him and made his head spin. He went forward and tentatively licked her and the taste was foul. Miss Smith moaned and said, “Get on with it I want your tongue right up my cunt girl! Or you get my truncheon right up the arse!” Bob moved nearer and started to lick feeling ill as he did so. As he licked her Miss Smith closed her thighs and Bob felt their massive hot flesh against her ears. He could not hear and as Miss Smith dropped the skirt he could not see and all he could smell was her foul odour. Then she started to get wet and her thick juices covered the shocked boys face as he licked away trapped in female servitude. To his relief after maybe ten minutes she started to wiggle and grunt and came filling his mouth as she did so. Miss Smith pushed him off and said,” a little rest my cute baby chicken and then you can do me again! Shame you are off limits as I would like to get my hand up your cunt and wank you off! How about you rub my tits when you do me a second time!”

Bob nodded gloomily and then he was suddenly aware that in his panties his penis was erect and painfully bent in it. Bob shuddered as his erection confirmed his submissive tendencies because who but a male pervert would enjoy what he had been forced to do to Miss Smith. He was also terrified she would see but his skirt covered him up. Not that Miss Smith looked as she pointed once more to her pussy and also undid her shirt. Her boobs were encased in a gigantic white bra and she undid the bra and they spilled out onto her stomach had two gigantic lumps of blubber making Bob shudder. Luckily Miss Smith did not see his reaction as he knelt aware that the sight of her breasts had actually excited his penis even more. He moved between her enormous thighs and applied himself to her wet open pussy and as he did so he moved his hands up. The ends of her breasts were on her stomach as Bob rubbed them and as he cupped them he was amazed by the weight of them and wondered how Miss Smith could move around with two such massive items on her front. Indeed as he rubbed her nipples and licked her pussy Bob became aware of the pain from his chest of the silicon breasts pulling from his skin and was pleased not to be a woman. However as Miss Smith moaned and rocked as she approached orgasm he was jealous of a woman’s ability to come time after time. Miss Smith had a second powerful orgasm and once moved pushed Bob off and leered down at him. Miss Smith smiled and said, “You are good on the cunt girl! Sara said you were a lesbian and she was right you lick pussy as if you want to not like some of the honeys who you can tell hate the taste of a cunt! Why some of them prefer to give a blowjob than go down on a woman! Stupid cows a cunt is best! Okay get back into action girl I want number three!” and Bob groaned and moved and once more licked the massive woman off and rubbed her floppy massive breasts until she reached a very powerful orgasm.

Then he was pushed off and Miss Smith smiled and said, “Great head honey! I look forward to next week as to let you share with Sara is a session a week! Cheap at the price! Okay now we have to go the educational unit and get you tested so follow me cutie!” Bob followed Miss Smith out and as he did so she roughly pinched his bottom making him squeak and her laugh. However that was all she did to him and Bob was very glad of that as he did not want her to know he was male as the thought of the massive lesbian discovering she had been pleasured by a man was too much to think of.

The unit was a small hut and inside was a skinny woman who made Bob sit and start to complete various tests. Miss Smith left and then returned with another prisoner. She was a massive black girl several inches taller than Bob and with gigantic boobs. Miss Smith said,”Okay girl I am going back on duty! This is Maxine and she will supervise the test!” Bob gasped at that as he realised this was the girl who had helped Sara get him in by fixing the records. As soon as Miss Smith had gone Maxine turned to Bob and said, “Having fun baby! A boy in a girl’s prison heaven but hell I bet! Particularly with Sara in charge that girl is one evil bitch! I could not believe her plan but good god she made it work a criminal genius. Now the price of my silence and keeping the records in order is sex from you! And not just for me boy! I am the top girl in the solid crew eight real tough black girls and we run C wing for the screws! Shame you are not on our wing but most of the girls have nice office jobs and will be able to enjoy you when you come for your literacy lessons here little toy boy! Now the teacher here is a lush and will not return and neither will Miss Smith so you can say hello to my pussy first as a girl and then the main event as a boy! And you had better have a really good erection or I am going to castrate you nice and slowly! Today you will only have me from the solid crew to satisfy as all the rest still think you are female! Still I am sure Sara deals with your lust after lights out as she is a right slut! Okay time to make me a very happy girl or lose your fucking balls boy!”

Bob felt sick as the girl stood and pulled off a pair of off white panties and leered at him. Maxine said, “Lie on the floor because as a top girl I obviously go on top! Something you as a honey will never do baby is be on top! Okay baby get licking my pussy! And think sexy because when I pull your panties off I want to see a really stiff dick!” Maxine’s pussy was covered in a fine fuzz of black hair as she reared over Bob and then sunk onto his face. He smelt her musky aroma but she did not smell as bad as Sara had and Bob knew she was being licked regularly. Bob started to lick her and felt her moan with pleasure on him and then he found her small bud like clitoris and concentrated his attentions on that and was rewarded by more moans from the increasingly excited girl. Then Maxine stopped and moved down him and said, “Skirt up and knickers down baby! I can get head any time I want but I have not had a cock up me for over a year!” Bob wiggled his panties down aware that he was hard and gasped as Maxine grabbed his dick. She smiled and said, “That feels nice baby!” and engulfed him in her wet pussy. As she did so she let out a loud deep moan of pure pleasure and said, “That feels wonderful! A real live bit of meat in me! Not a girls tongue but a guy’s dick! Perfect just what I need! Okay boy relax and let me ride you! I will not take long to come but no way am I letting you go after just a single blow!” and she slowly with a big smile on her face started to ride his erection. Then she lent forward and pinned him down and started to move faster and faster until she was hammering into him. Her boobs moved under her T-shirt and sweat appeared on her face as she reached a powerful orgasm. Then she slowed and resumed her slow languid progress on his dick. She said, “That was nice it was worth helping Sara to get a real cock in! The lucky cow getting this up her whenever she wants all I get is head! And head from a girl not a guy! It is not the same baby for a big girl with a big girl’s appetite for sex! This feels lovely god when I was on the outside I used to ride my man for hour after hour! I used to have to tie the guys down because they would complain about having a sore cock! Still you fail to please and then you will not have a cock and I will wear your balls as my ear rings!” and she started to go faster. Soon Maxine was moaning as she reached a second powerful orgasm on Bob. As she peaked Bob felt his dick pulse and he came moaning underneath her. Maxine laughed as she watched him come and said, “My power cunt was too much for you boy! Good! But remember baby you have a lot of sex to give and only one set of balls so do not empty them to fast boy! Okay that was fun and I will screw you soon! Now I am going to leave my pussy nice and sticky so the rest of the gang believe me when I tell them we have a cock slave to fuck!” and she stood up and replaced her panties. Bob staggered up pulling his panties over his sore dick and letting the skirt drop. Quickly both he and Maxine looked as if noting had ever happened and Bob realised this was one advantage a skirt had over trousers.

Bob finished the test answering the questions wrong as Sara had ordered. It did not take him long and when he finished another officer entered the room. It was the massive ugly Miss Town who said, “Okay bitch get out of here I am taking over!” and Maxine left giving the officer the finger behind her back as she did so. Miss Town leered at Bob and said, “Sucking her cunt I bet girl! Well I am glad you have warmed your tongue up girl as you have my cunt to satisfy right now! So get on your knees and get over here I want it right up me! Rumour is that you suck pussy well so let me have a go girl!” Bob shuddered as the evil ugly woman flopped onto a chair and leered at him. Trapped he knelt and crawled over as she lifted her skirt. Underneath she had removed her panties and Bob was confronted by her large hairy smell pussy and resigned he set to work to make her happy. Miss Town moaned with pleasure as he licked he rand said, “Yes you do know how to kiss a woman you lesbian whore slut!” Bob groaned as once more he licked a female guard off knowing if they discovered he was male he would be at least castrated. Soon Miss Town started to moan and her wetness filled his mouth as the massive ugly woman reached orgasm on him. Then she pushed him off and leered down and said, “I can tell you have licked a lot of cunt girl you know how to get a girl off! Still I prefer a virgin tongue that I can train to lick my cunt your expertise as a pussy licker does little for me baby but when I tell the other guards baby expect to have a lot of cunt to kiss as most of the girls prefer a girl who knows what she has to do! Okay as a finale girl you can kiss my arse!” and Bob gasped as Miss Town stood and turned and raised her skirt and he was confronted by her huge white flabby bottom. He gingerly kissed the massive bottom cheeks and Miss Town laughed and said, “Not so sure on a bum girl well I want it licked and your tongue right up my crack after all why should I waste paper when a bitch can lick my bum clean? Get going whore slut!” Bob groaned but licked her massive cheeks and then shuddering applied his tongue into her bottom. Miss Town moaned and pulled her bottom cheeks apart so he could lick deeper and feeling sick Bob did so. As he licked away he felt Miss Town move a hand onto her pussy and masturbate and her groaned as she came thrusting her bottom hard against him. Then she pulled off and leered at him and said, “Make certain you wash your face girl as you will have a lot of cunt to lick tonight and then he gasped as Miss Town felt down and brutally squeezed his plastic breasts. One came loose and then Bob remember that for a girl this would hurt so he moaned and Miss Town laughed and called him a slut before walking away. Bob stood and quickly adjusted his bra and plastic breasts thinking he was pleased that Miss Town had not done that to his balls.

Then Bob went and washed his face and within a couple of minutes Miss Smith returned and leered at him. She said, “Heard you pleasing one of my colleagues! She says you lick cunt really well but she prefers a virgin pussy licker the silly cow I like a girl who knows how to lick cunt properly! Of course what I really want would be a guy to serve me with his cock and tongue but no chance here so your girly tongue will have to do!” Bob groaned at that as he realised that if discovered he would also be raped by some of the female staff as well. Then Miss Smith ordered him to follow her and took him back to the cell block and told him, “Association time where you can say hello to the other girls Bobbie and in your case lick pussy! Do it well girl as I want a happy cell block tonight!”

Part five First evening

He was left in the well of the block but quickly Sara came over and grabbed his arm. She was red faced and dirty as she smiled at him and said, “Having fun Bobbie? Well you have paid two of the screws off and Maxine has gone back a happy girl! Now we have a couple of hours until lock down and you have some more ladies to say a big hello too! Follow me you can eat latter! Or rather eat food latter because I think you are going to be tasting quite a few pussies!” Bob groaned as Sara pulled him up to their cell. Worse outside was standing the tough looking muscular Charlie and a group of girls. Sara pulled him up to them and said, “Here she is girls my honey Bobbie a real cute pussy kisser! Now as I am a friendly top girl I will let you lot share her with me! But remember she is mine and no touching of her cunt or tits they belong to me!” one of the girls another plump blonde with short hair and big boobs leered and said, “Yeah she looks a right dog still she is meant to be good on the cunt so we will have some fun!” then Charlie said, “Yeah what we need are some good pussy licking girls to suck us off!” the girl laughed and said, “No what we really need is a hard cock to ride whenever we fancy it!” Charlie laughed and said, “Yeah Debby we do! Okay this evening rather than putting Bobbie on general hire Sara has given her to us! Okay Jaz go and get sucked off!” A buxom blonde with bad teeth grabbed Bob and pulled him into the cell with a laugh as Charlie grabbed Sara and steered her off to one side.

Jaz sat on Bob’s bed and lifted her skirt and said, “Get my knickers off girl and then get sucking! And shut up I want to imagine it is a handsome man doing me not an ugly bitch!” Bob moaned as he knelt and gently pulled her panties off shuddering at the sight of her sweaty hairy pussy. He applied his tongue to her and started to lick grimacing at her stale taste and already feeling sick from eating too much pussy juice. Jaz moaned and said, “Get stuck in that feels great! God if all girls gave head as well as this I would become a lesbian!” Bob smiled to himself at the irony of Jaz getting off on his tongue thinking about having a man rather than a woman doing her while he knelt and did her. In fact he felt his dick stiffen and groaned as it chaffed in his panties. Soon Jaz was moaning and shaking and she came moaning several men’s names as she blew. Jaz got up and pulled her panties up and said, “You are good at pussy kissing shame you do not have a cock because you know when I look at you I could easily see you as a man!” Bob blushed at that and Jaz smiled and said, “No seriously you could be a man but a real pretty man! Sorry I did not mean to hurt your feelings I know it is rough in here particularly for a honey!” and with that Jaz left obviously embarrassed. Bob felt confused as it was obvious Jaz had interpreted his blush at being seen as a man as annoyance at being insulted.

Quickly the next girl was in and she was a slim redhead with a big nose. She too sat and raised her skirt and resigned Bob pulled her panties down exposing her dirty pussy covered in a thick red thatch and set to work. The redhead came quite quickly but did not tell Bob her name and was replaced by another thick set blonde who just sat and waited for Bob to pull her panties down and satisfy her with his now tired tongue. By now Bob realised the truth that in the prison sex was a rushed affair conducted virtually fully clothed by the girls. Also as Sara had said the top girls ignored the needs of the honeys and did not touch them or really even acknowledge them. Bob realised something Sara had not however known. That was that one of the reasons for this was not to do with prison discipline it was simply that most of the girls were not lesbians and were only using a member of the same sex to get off with because no man was available. Therefore they restricted contact and he was sure most of the girls were thinking of men as he licked away and once more the paradox of the situation made him smile. After the girl on his tongue had come three more times nameless girls sat and he removed their panties and pleased them. By the time he had satisfied the first six girls in Charlie’s gang he was feeling sick.

Worse Charlie and the other girl Debby came in. Charlie smiled and said, “Prison rules say no more than three girls in a cell and no more than one from another cell but I think we can risk it for tonight Bobbie as we have several lookouts. Well the rest of the gang think you give great head baby and that means Sara will get a lot of bookings for you on the general wing! You even got Jaz off and that is not easy for a girl! Okay lie on the bed and put your hands behind your head Bobbie!” Bob gasped and did as she wanted and Charlie smiled and said, “I spoke to Sara and she agreed with me that our gang oaths are strong so we can let a few girls into the secret!” Bob moaned and felt even sicker at that as he saw Debby looking puzzled. Charlie continued, “Now Debby is my number two and we like to share! Now Debby dear remember you said what we need is a hard cock to ride whenever we fancy? Have a look at this!” And with that Charlie pulled Bob’s skirt up and his panties down. Bob’s dick sprung free erect and eager making him groan. Debby stared in amazement and said, “A hard cock what the hell is she a he man?” “No!” laughed Charlie, “She is a he Sara has smuggled her boyfriend into the prison as a female prisoner and trapped him here as her sex toy! And we get to fuck him as well!” Debby laughed and said, “Fucking great I love getting something big up me! It has been nine months since I screwed a guy!” Charlie laughed and said, “Six months for me! I can hardly wait but Debby this is the big secret the screws would go mad if they found out! Think of the stink and how stupid they would all feel! If the authorities find out then this place will not be such an easy number!” Debby nodded and said, “True not even the rest of the girls but I tell you Charlie I think Jaz will guess she told me that he had a man’s tongue as no woman had ever licked her off like that! We will have to tell her!” Charlie laughed and said, “Okay! Now let’s fuck him! Me first Debby!” “Okay he can lick my tits while you do him! I love having my tits kissed by a guy! No girl can make a tit tingly like a man can!”

Bob gasped as Charlie pulled her panties off and mounted him as Debby pulled her T shirt off and quickly her bra. Her boobs were big and fat as she leered down at him and said, “Good god a guy to fuck! Now kiss these baby I want to get even wetter so I can go straight on top when Charlie has come!” Charlie meanwhile was pushing Bob’s erection into her pussy and she laughed and said, “Yeah make her wet boy as I will not take long! God that feels wonderful! Something right up my cunt! Warm and sexy! You can come in me Bobbie! In fact I want to feel you shoot a load up me when I come as that would be just right for my first fuck for ages! Bloody hell I have really missed a hot cock!” and she started to ride him. Debby pushed a boob into his face and said, “Yeah blow for Charlie honey but stay up as I want a ride and then I want a come load as well!” Bob shudder at the thought of having to come for both girls but as Charlie roughly rode him he felt his excitement rise as well as the excitement of all the cunnilingus got to him as did the softness of the boob in his mouth. Charlie came with a sob and as she did so Bob let go moaning and desperately not biting the soft boob filling his mouth. Charlie pulled off and said, “God that was great I loved to feel him come! Okay get on him Debby before he goes soft! That is the only thing better about a girl honey they do not need to stop after coming!” Debby mounted Bob and pushed his sensitive dick into her pussy and said, “No worries I learnt a long time ago that a strong vagina can keep a guy hard whether he wants it or not!” Bob moaned in pain as Debby rode him and to shut him up Charlie took her top off and then pushed a large sweaty boob into his mouth saying, “Shut up you will suffer a lot worse than this if you are found out! If you want to live boy you ensure every girl leaves this cell a happy girl! Do not worry you do not have to come every time with me I just wanted to feel man come in my pussy for once!” Debby rode away moaning her big boobs bouncing up and down and Bob groaned underneath her. She rapidly came on him moaning as she did so. Then she sat on him and said, “Shit the bastard did not come!” Charlie laughed and said, “Typical guy to selfish to come when you want him to blow! Get off Debby I will ride him now and Bobbie do not come with me but hold back for Debby’s second go!” Bob gasped as once more Charlie raped him as and as she did so he licked the other breast of Debby. Charlie came just as fast this time and soon once more Bob was being ridden by Debby while he licked Charlie’s breasts. He felt his excitement rise but was able to hold off and come with her moaning as he had a very powerful orgasm.

Debby pulled off and Bob moaned as Charlie replaced her and once more he was in her powerful vagina. Now as she moved up and down he sobbed in pain underneath her making both girls laugh and Charlie said, “No way boy we want sex and even if you are a man you are still a love slave! So lie still and let me screw you! Debby we do not have a lot more time how about getting head off him while I do him?” “Great idea I would love to share a guy with you Charlie remember how we said we would do a guy together when we got out! Well I never imagined doing one in a cell!” “I know Sara is a queen bitch but getting a guy to agree to be trapped here as her slave well magic girl!” Bob shuddered as Debby mounted him and presented her wet hairy open and sticky pussy for licking. He struggled to satisfy her with his tongue as Charlie rode his tender dick. Both girls took longer to come but came together sobbing with delight with Charlie clutching Debby around the waist as she came. Then Debby got off as Charlie moved up and said, “Better clean my cunt boy! I do not want my regular honey to wonder why I have come up me!” Debby laughed and said, “No way do I want a girl tonight! God a boy is so much better! When can we fuck him again Charlie?” “Probably tomorrow night I will ask Sara!” “Lucky bitch she gets him all night!” Bob licked Charlie’s filthy sticky pussy clean and then she pulled off him and said, “Pretend to be a girl well boy because if you do not I guarantee you will lose those nice balls of yours and your cock before the screws can save you! Imagine doing five years in a male prison as a eunuch! Much worse than a little pussy service here!” And with that she and Debby dressed and left Bob dazed on the bed.

He pulled his panties over his sore dick and sat up feeling very ill and knew Charlie had spoken the truth and until he was due to be released he was a helpless slave who had to do as any girl wanted. Sara came in and smiled and said, “Did you enjoy that? It must be a boy’s daydream to live with a load of really randy girls? No! Well I did sort of warn you!” “You did not!” “Yes I did sexy I told you it would be tough and hard but you would get loads of sex more than a normal man could cope with! Well did I lie?” “No but” “See so stop complaining and eat your supper. It has gone cold but you are going to need the energy. Charlie and Debby thought you were great and the rest of the gang think you give great girl head. They want to use you tomorrow night and I have agreed!” “Oh no!” “Yes I have Bobbie we need to keep Charlie and her crew onside. They have to feel part of the team or they could sell us or castrate you for fun! You want to keep your balls and I want you to keep them and also not get sent away from here without parole! We are both taking a risk you know honey! Now eat up the lights will go out soon!” Bob did so even though after so much cunnilingus he felt sick. Then in the doorway appeared Miss Smith who smiled and said, “Time to lock you two love birds up! I hope you enjoyed the last couple of hours Bobbie you seemed to be a busy girl!” and with that the big door was slammed shut and locked.

Bob finished as food and gasped as Sara removed her top and bra and gently rubbed her boobs. Even though sexually he was exhausted he felt his dick respond and moaned as he saw Sara smile in triumph. Then the lights went out and Sara said, “In bed baby!” Bob removed his outer clothing and got under the sheet and quickly Sara was naked and in the bed. She hauled off his panties and rubbed him erect and them threw a leg over him and mounted him and said, “I do not think you will come over fast tonight honey so I can get a few real nice long rides!” Bob groaned as his mistress ravished him. Sara used him for over thirty minutes until he had a very powerful orgasm and passed out and by then she had come four times. Quickly however her eager hands and tongue got him awake and after providing her with oral delight his ordeal resumed. For nearly two hours she used him moving from his sore dick to his exhausted tongue as the fancy took her and coming at least ten times before finally she dragged a painful orgasm out of him and he passed out knowing she would still use his unconscious body for her pleasure.

Part six Another day

Again Sara woke him up early and demanded and received oral pleasure from the exhausted boy. Then she helped him wash and apply make up and check he looked as feminine as possible before they had to go to work once more. Another morning of tedious tiring labour followed for Bob in the laundry room with the other honey girls and by lunchtime he needed to sleep so tired was he. However he was returned to his cell where a laughing sweaty Sara made him give her oral pleasure before allowing him a short rest. However then Miss Smith arrived and said, “You Sara back to work you have a lot of dirt to shift before the afternoon is over! As for you Bobbie you get it nice and easy as you have been tested as needing basic lessons every afternoon! Very relaxing for some I am sure but I suspect Sara will make you work tonight!” Bob groaned as he knew that all the education centre meant was that Maxine got hold of him.

As he expected when he got there Maxine was there and the massive black girl leered at him. Worse standing next to her were two more black girls. One was a very fat girl with a massive bottom and boobs while the other was a pretty girl with a delicate face and large boobs on a curvy body. However in her case she had a large scar on her face making her look strange as she and the other girl smiled at Bob. Maxine said, “Good afternoon officer. The officer in charge is unwell and we are to supervise the prisoner’s orientation lesions.” Miss Smith laughed and said, “Too pissed to wake up I bet! Right be nice to our little Bobbie as his top girl Sara has strict rules about using her!” Maxine nodded and said, “We will not upset Sara and cause a fight officer you can rely on us to behave with her.” And Miss Smith gave them a laugh and then left Bob to his fate with the three black girls.

Maxine said, “Hello Bob meet Charlene and Beverley my two closest friends and fellow members of the solid crew!” Bob groaned as Charlene the fat girl and Beverley the curvy one leered at him. Maxine continued, “My crew could not believe I had a come filled cunt last night but I assured them that Sara had got a toy boy in and they were amazed! Do not worry they will keep their mouths shut but of course they all want a ride on your sunshine stick! Particularly after I told them what great orgasms I had on it yesterday! Now we are going to be alone for an hour and we have already got a nice comfortable mattress for you to lie on so get naked and let us fuck you! Or do you want to be castrated?” Bob shook his head and stripped as the three girls watched. When he was in his underwear Maxine came over and squeezed the plastic breasts and said, “Neat! They look okay so long as you cannot fully see them! Okay get them off we want to fuck a boy not a transvestite!” Bob moaned and removed the breasts and felt a cool freshness on his chest as he did so. Then he pealed off the panties and was aware of all three girls watching. As soon as his dick was in view Charlene grabbed it and as it got hard in her hand she said,”Wow a real one! God it feels nice as it gets hard and ready for my cunt!” Maxine laughed and said, “Get on the mattress baby and keep it up you have three active young ladies to make happy in the next hour!”

In the corner of the room the girls had placed and old tatty mattress and Bob lay on it as all three stood around and then stripped naked. Then Bob gasped as all three jumped him on the mattress. Soon he was being kissed and groped by the three hot girls and he was aware of how unclean they all were. He knew this was not their fault as the prison wash facilities were inadequate particularly on a hot day. However the smell and then the taste of unwashed females made him feel ill. Soon he was kissing Maxine’s massive black breasts as the other two amused themselves with his groin laughing at his erect penis. After that he licked the floppy boobs of Charlene and then Beverley’s firm pert black breasts while all the time his groin was teased.

Then he moaned as Maxine mounted him and started to ravish him. Soon he was pinned back by her as the big black girl powerfully rode him with the other two girls lying and kissing him and urging him to stay hard for them. Maxine came powerfully on him and pulled off and quickly he was mounted and engulfed by Charlene. She was a rougher rider and Bob groaned as she ravished him making the other two girls laughed as quickly Charlene came on him. Instantly she was off and he was in Beverley and her tight pussy made him moan as expertly she rode him. He knew he had to come but desperately held on until to his relief Beverley came and then groaning he came as well. He was given no rest as Maxine once more mounted him. Charlene laughed and said, “That was nice dick work but having a boy to fuck rather than a girl makes me super randy! Can I use his mouth Maxine? Excellent okay boy kiss this!” and with that Charlene mounted the stunned boy as well. Bob groaned as her large wet dirty hairy black pussy was forced into his mouth but a slap on the head got him licking as Maxine grated his tender dick in her powerful pussy. Then Beverley grabbed his hands and placed one on her boobs and the other on her pussy and soon Bob was desperately trying to please the three black amazons at the same time. Maxine came first and moved off and to Bob’s horror Charlene replaced her on his dick while his tired mouth was presented with the open pussy of Beverley to lick and Maxine moved and took control of his hands. After Charlene Beverley ravished him while Maxine enjoyed his oral attentions and Charlene his hands. For an hour he was abused and used by the girls without any rest. Every three or four minutes the girl on his dick moaned in orgasm but was replaced by the next eager rider. Twice Bob had powerful orgasms himself once into Beverley and the other again into Maxine but the girls forced him to carry on using their vaginal muscles to keep him hard and their fists to keep him rubbing and licking.

Finally Maxine said, “Last time ladies!” and he finished off them one by one until he had Maxine powering away on his very sore dick with the other two lying sated and watching. Then after Maxine had come she sat herself on him and looked at him and said, “Great gang bang honey! Now every afternoon you have some lessons here and I am going to ensure that every afternoon we get you alone in this room with three of the solid crew for some girl fun! I know Sara is using up your cock but boy it had better be ready for the sex because the girls of the solid crew know how to hurt a guy who stays soft! Okay we had better dress and look respectable!” and the girls got up laughing in delight. Bob stood and replaced the plastic breasts and the bra and panties and as he did so Maxine looked and said, “Amazing with the make up you pass as a girl but naked on the mat with your cock right up you are a true boy! Okay when you have your skirt and top on boy I had better do your make up! And get used to calling you a girl honey rather than my toy boy!” Bob stood exhausted and let Maxine do his face and while she did so the other two girls groped his bottom laughing as they did so.

After thirty or so minutes another large female guard turned up and took Bob back to his cell. He lay dazed on the bed. He knew now he did not want to live with Sara and knew as soon as he was out he would never visit her again. However he knew his only hope was to keep quiet at that even though he wanted to scream at her for having tricked him into coming. His groin ached and he knew he had many days before he was released to go and knew by then he would feel a lot worse. Then a bell went and the exhausted boy stood and went and got his tea. He was eating it in the cell when Sara arrived. She was red faced and covered in sweat and said, “Those bitch screws made me dig fucking dirt all afternoon the cows! I hate it in here! Still at least I have my boyfriend to screw tonight! More than those fat cows do they could not get laid anywhere they are so ugly! Not a problem for you baby as Charlie and her gang want to use you in association and also they have told Jaz you are a guy as she seemed nearly to have guessed so she wants cock as well! And after Maxine and a few of her crew I bet you are a little sore! Still you told me you could cope with anything a girl gave you sexually so we shall see! And remember as soon as it is lights out I want a long long session of loving!”

Bob moaned making Sara smile but then Charlie and her gang turned up and soon Bob was on his knees facing once more a girl’s pussy. Five times the tired boy gave a girl cunnilingus until she moaned in orgasm aware all the time that while he was half erect his dick ached and shuddering about what was soon to happen. Then it was Jaz’s turn and she leered at him and said, “I did guess it you are a boy! I knew it was not a girl sucking me off! Now Charlie has told me the big secret baby I get properly laid! God I need that! For most of the girls a girls tongue is okay but for me I want a man! Okay get on the bed and show me your knob! Oh very nice! Looks a little red but I imagine lots of ladies are getting pleasure off it! Feels nice and smooth and hot just right for me! Okay kiss my pussy for a minute then I want a ride to orgasm and honey I want you to fire into me as I come! That’s a good boy lick me excited and wet! I bet I am really smelly as it was hot work today and I have not washed! Still here you must be used to the natural smell of a woman! God you have a nice tongue you can give me number two with it! But first I want your knob! Right now! God that feels great! Really great! Okay relax and let me ride you after all you may be a boy but you are still a love slave! Great! Yes! Yes! Yes! Yes! Yes! Wow I came really fast and you have not! Naughty boy! Still I will be kind you can lick me out and then we can fuck again and then I want to feel spunk up me! Okay kiss this baby! Nice! Get your tongue right up me honey! Very nice! Yes! Yes! Keep going whore boy! Yes! Yes! Yes! Wow I am a right slut for a cock! Okay inside me again honey and remember I want you to come! Relax and let me ride you baby! That feels great! Yes! Oh Yes! I can feel you are getting there honey let me come first! Yes! Yes! Hold on baby nearly there! Yes! Yes! A little more! God! Yes! Yes! Yes! Come now you bastard! Yes! Yes! Yes!” and together they came. Afterwards Jaz pulled off looking dazed as Bob lay shattered on the bed. Jaz grabbed his soft red dick and said, “So much pleasure! I tell you baby even on the outside you would be a great fuck but in here you are solid gold fuck meat! Now relax and let me lick you! Firstly because I know Debby wants a hard cock knob to get on and secondly because I love the taste of a young man’s drained hot knob!” and with that she took him into her hot mouth. Bob sobbed in pain as she sucked him and forced his exhausted penis hard. Then with a laugh she dressed and left him for the next girl. This was Debby who removed her panties on got on the bed and Bob and made him first lick her sweaty pussy before ravishing him. Three times she came on him before moving off and dressing and then quickly Charlie was in the room and she ravished Bob until she had come twice. As she had her first orgasm Bob had a painful orgasm but he was punched and slapped to stay awake and after licking her clean he was made to rub himself hard for her inflexible pussy once more.

When she left Sara returned and laughed at him lying shattered on the bed and forced him to make himself decent. To do this she slapped him around the face the first time she had hit him not that the broken boy really noticed this abuse. As soon as the lights were out she was in his bed. He begged her to let him rest as he was finished but she just laughed at him. Then she said, “Okay baby I will let you have a few more minutes for your cock to recover but meanwhile baby so as not to waste time you can lick my entire body from top to bottom to make me clean!” Bob moaned but was helpless and was soon kneeling and performing oral duties on Sara’s slim but filthy body. By the time he had finished this task and it took him nearly an hour he was feeling sick. Sara had come twice once when he licked her breasts she had masturbated and the other time when he had licked her matted pussy. Then she forced him onto his back rubbed him hard and for two long painful hours she ravished him using his mouth or his dick as she wished. Three times he sobbed in some sort of orgasm as Sara had numerous comings before finally even Sara was sated and she let him pass painfully into sleep.

Part seven More time

The next morning Bob felt like crying when Sara woke him up and demanded oral pleasure before forcing him to dress and put on the make up. He felt like a zombie as he staggered to the wash room to do more tedious laundry. Linda was sympathetic and said, “Hideous being a honey I know! And much worse for you as Sara is lending you out not only to Charlie and her crew but also the solid crew girls and those are real bitches. I wish I could help but baby here it is every girl for herself!” however Bob was pleased when she took half the ironing off him so he was at least able to keep up with the work. Then at lunchtime Miss Smith arrived and told him, “You are a very lucky girl as it has been agreed for you to spend all afternoon in the learning centre! Okay follow me baby!” and Bob groaned as he knew all this meant was that Maxine and her girls got more access to his body.

His worse fears were confirmed when he got there and saw Maxine standing around with a whole group of girls. Miss Smith moved them on but soon he was left alone in a classroom. Quickly Maxine came in accompanied by Beverley and a third girl. She was a tall slim black girl with small boobs and a long nose who leered happily at him. Maxine smiled at the frightened boy and said,”Hello Bobbie ready for some hard sex? Say hello to Jenny she is really looking forward to getting a dick up her fanny! And the good news is we have arranged it for you to spend an hour pleasing us three and then immediately afterwards you can please three more of the solid crew! Two hours an afternoon whore boy of lovemaking and girl pleasure to give! Okay get in the corner and get them off because we want to fuck and fuck a lot!” Bob groaned but moved and stripped and was soon lying naked on the dirty mattress as the three girls stripped naked. As he looked at the slim girls small breasts and lanky legs. Maxine lent forward naked and powerful and rubbed his dick making him moan. She laughed and said, “Must be getting sore baby! Hardly surprising with two crews of girls to satisfy and Sara! Now do not worry we have five girls on look out so we will not be disturbed until we have all got laid! In the solid crew now honey the girls get three days on your cock and then a day off! Nice for us hard work for you because if you do not please us we will ram a baseball bat up your bum for starters! Okay now kiss my tits and think sexy because you are doing all three of us at once as we only have an hour to fuck!”

Bob groaned but licked her boobs aware of the other two naked girls gently rubbing him and then Maxine got on him and rammed his dick into her pussy as she did so Beverley mounted him and presented her pussy to his face and then the third girl Jenny grabbed his hands and placed them on her small boobs. Bob groaned as Maxine rode him and he licked Beverley and rubbed the erect nipples of Jenny as he realised that the solid crew girls intended to ravish him as they had done so yesterday. This turned out to be true because when Maxine orgasmed the girls moved and into Beverley’s pussy he went while his tongue discovered just how dirty Jenny’s pussy was. Beverley came quickly and the girls moved and Jenny sobbed in delight as he went up her and came in less than two minutes before moving once more onto his hands. For fifty more minutes the girls used him and each girl had four more orgasms during the orgy. Bob was kept licking, rubbing and ridden by the girls and came into Jenny and then much latter Maxine but the girls powerful vaginas kept him in action. Then the three girls got off him and dressed but Maxine ordered him to lie still. Within three minutes into the room came Charlene and two more large plump black girls. They stripped naked and once more Bob was forced to give triple satisfaction to a moving train of hot sweaty black girls. They used his body for an hour dragging two more painful orgasms out of him as each girl sobbed four times in orgasm on him. By the end he felt exhausted sick and his whole body felt squashed from the weight of the girls on top of him.

The worse thing was when they pealed their hot black bodies of his broken one Charlene cupped his balls and said, “Same thing tomorrow honey pie! We love to fuck you! So keep it hard or suffer!” and only then he was allowed to dress and re apply his make up and he sat exhausted waiting for an officer to take him to his cell. He ate his tea and then Sara turned up and said, “Hope you have some energy baby because I need some cash so have sold your tongue to six ladies! Try and get them off fast because Charlie and Jaz want some cock and a couple more of her crew want girl tongue! Okay on your knees baby while I get the first girl!” Bob shuddered but did as she wanted and moaned as into the room came a plump blonde girl called Fiona who smiled and lifted her skirt and removed her panties and sat in front of Bob and said, “Kiss cunt honey! I paid three chocolate bars for this so make it good!” Bob shuddered at being sold as a sex toy for such a small price but applied himself to her dirty pussy and soon had her moaning in orgasm. Fiona got up and pulled her panties up and said,”Nice head as Sara says you do know how to lick a girl well! Okay see you around and baby I will buy that tongue of yours real soon!” The next girl was a dark haired skinny girl who moved in front of the knelling Bob pulled her panties down and sat on the bed legs apart and once more Bob licked dirty pussy. By the time all the six girls had been satisfied he was hot and his mouth ached. Worse however was the appearance of two members of Charlie’s crew who spat at him before he licked them both off. Then to his horror Jaz and Charlie entered the room. They made him remove his panties and lie on the bed as they removed their panties and then mounted him and he satisfied them both with his tongue and dick until both had come four times. He spurted into Jaz but Charlie ravished him without rest immediately after he had come and kept the exhausted boy hard. He was saved from further abuse by the bell and laughing the two amazons got off him and left him dazed on the bed. Latter Sara got in his bed and used him until he passed out with exhaustion under her sexy nymphomaniac body

The next three days were the same with Sara waking him for oral pleasure then a morning of laundry followed by lunch and oral pleasure for Sara. Then came two hours in the education centre naked on the mattress pleasing six members of the solid crew. The other two girls in the crew Bob discovered were large powerful black girls. By the time the girls of the solid crew had finished with him he was a broken boy and wanted to curl up in the corner holding his sore dick and empty balls and sleep. Only he could not as every night Sara sold his tongue to six girls and then he satisfied a couple of girls from Charlie’s crew on his knees before Charlie and either Debby or Jaz entered the room and ravished him. Then after lights out Sara abused his exhausted body until he passed out. A day when they had no staff to let them out was for Bob nearly a relief as he was locked up with Sara and after ten hours of sex even she was satisfied. In fact Bob was counting was the days until he was released and could safely leave this mad house and the danger of death, imprisonment and worse slow castration.

The next day was the mind numbing physically exhausting return to service and by the time the lights were out his mouth and dick ached as Sara got on him in the bed. He did not think things could get worse when suddenly as Sara reached yet another orgasm on his shattered body the light came on and the door was flung open. Standing there holding a massive wooden baton was Miss Smith who said, “Having fun girls? Get out of the bed Sara we need a word!” Sara climbed off Bob letting his erect tender dick flop back as he pulled up his panties. Sara said, “Come on Miss we had a deal I gave you head from my honey and you left us in peace!” “Well Sara I am a little confused because when I looked it you seemed to be riding the girl! Very odd?” “No we were playing at man and woman and we were acting!” “Very good acting children particularly the orgasmic moans Sara! Still such things would not surprise me as I know that you girls get up to all sorts of kinky things after lights out and play all sorts of fake man games! However get up Bobbie because I want to search you because I think I may find something”!” Bob stood dazed and shaking with terror as Miss Smith approached him. He was sure she could see the outline of his dick in the panties and this was confirmed as she said, “And what is this?” and Miss Smith’s hand moved and pulled the panties down exposing his erection. Bob gasped as Miss Smith gripped his dick and said, “Alive and hot if a little tired and those are fake tits! Okay Sara and whoever you are what is going on?” Bob felt like crying but Sara was quicker and said, “Please Miss Smith she is a she! I first found her when I was inside last time she is one of those transsexual people she may look like a man but she is a girl! “Looks like a boy and feels like a boy Sara!” Bob groaned as he was aware that Miss Smith had not let go of his dick and was indeed gently rubbing it and he knew he was in deep trouble. Sara was equal to this and said, “Outside she calls herself a girl and acts like one but medically she is quite male as you can see and indeed feel! In a male prison she would really suffer so she is safer here!” “A she male?” “Yes Miss Smith” “Does the medical officer know? I do not think the full facts are in her records but some are! Please Miss Smith you cannot let her go to a male prison!” and Sara pretended to be upset. Bob gasped as he felt Miss Smith give his erection and squeeze and then she said,”True we have a duty to protect the prisoners even bitches like you Sara! And this she man has made Charlie’s gang and Maxine’s gang a lot easier to handle and they are not fighting each other or you! A few toy boys in here would make it a lot easier place to work in! Okay Sara I will adjust Bobbie’s medical records to show the truth as to her masculine qualities. However Sara I warn you pull any more stunts and you will get big face ripping trouble do you understand me?” “Yes Miss Smith” “You are here for a long time you know and I cannot see you surviving with your attitude!” “Yes Miss Smith I do try and Miss Smith I do have an appeal to be heard!” “You Sara are pure evil!” And Bob inwardly nodded in agreement with Miss Smith but was aware that her grip on his erection had not lessened. Then Miss Smith spoke again and said, “However our deal is now daily with your honey and how I want! Okay?” “Yes Miss Smith” Right for tonight Bobbie you are sleeping in the punishment cell! Also Sara keep this secret or you will get slashed!” “Yes Miss Smith” “Follow me Bobbie!” and Miss Smith pulled the terrified boy out by his erection.

She took him to a small cell with just a bare mattress on the floor and pushed him in and onto it and then knelt over him on the mattress. Her hand resumed rubbing his dick making him moan. Miss Smith smiled and said,”Sara speaks a load of shit! You are a full male Bobbie! Her daft boyfriend in fact! I now remember a sad weak wimp visiting the bitch! And getting hard in his pants from her foot! Well if I turn you in the shit hits the fan big time here and I could lose my job! So baby if you do not play ball the simple thing is for you to lose them! Yes baby muck this one up and I will get a couple of the real lesbian man haters to cut your cock and balls off and crave your chest up so no one would ever have guessed you were once a man! So you are going to stay here as Sara’s toy and keep the girls happy as they think they have pulled a massive one over us! And even better I get laid! I do not mind a girl doing my muff but I love a man doing me and baby your cock feels fucking great! Relax and let a mature lady show you the real joy of sex!”

Bob shuddered as Miss Smith stood and stripped naked. Her body naked was gross and her boobs hung blubber like down as she got on the mattress and Bob. He groaned at her weight as she wiggled up and said, “Some oral foreplay baby before the main even as I can see Sara has got you nice and hot for me!” once more he licked her large pussy and then he groaned as she moved and engulfed him and then heaved up and down on his battered body. Quickly her massive boobs shook as she rode him and Bob saw in the moonlight her flesh wobbling as Miss Smith quickly and powerfully reached orgasm on him. She pulled off and rubbed him and said,” I should have guessed when you gave me head you were a boy! Now you did not come so I will give you a treat honey knell and fuck my tits!” and she knelt and raised her massive breasts and cupped them together. Dazed Bob also knelt and placed his dick between their sweaty surfaces and urged on by Miss Smith he moved in and out. It felt nice but Bob was exhausted and after several minutes he had not come. By then Miss Smith was excited once more and she grabbed him and flopped back and slotted him on and into her and placed her hands on his bottom and forced the exhausted boy to love her. As Bob did so he moaned as Miss Smith pushed two fingers up his bottom and used those to control his movements as he slowly brought her once more to a powerful orgasm. Then she pushed him off and said,”Still not coming! I know you have had a lot of sex but I want to see you come! Okay I think I will show you how a girl feels baby on your front! I am going to rape your arse until you blow!” Bob gasped as she turned him over and then Miss Smith positioned the end of the large baton at the entrance to his bottom. He begged and then screamed as she pushed it up him and as he sobbed he heard her laugh. She raped him and then fisted his dick as she urged him to come. Bob was sobbing in pain and then suddenly felt an intense pain and had some sort of orgasm and would have passed out if Miss Smith had not squeezed his balls. She carried on raping him and said, “Tell me when you can keep it up I want cock!” Bob sobbed and told her he could and was soon on his back underneath her suffering in her large pussy. He felt ill as she used him but let her have him until twice more she had moaned in orgasmic delight on him. Then she dragged him up and back to his cell and threw him in. Sara woke up and asked him what had happened and then laughed and got him into bed and then used him until after thirty minutes he came again and once more passed out.

Part eight closure

The next day adding to his general body pains was an aching bottom from the baton. The morning passed in the laundry room but at lunchtime Miss Smith took him back to the punishment room and made him get naked and there she stripped and ravished him until she had come three times and she had drained a shot from him. Then in the afternoon he served six members of the solid crew in an exhausting double hour foursome. Then in association time his tongue served six girls and then Charlie, Debby and Jaz. Then after lights out once more his nymphomaniac mistress broke him with her slender body. Each of the next five days was the same and all the time Bob’s body ached from the sexual demands being placed on him. Many times he wanted to cry and beg to be realised but he knew before he was separated from the girls they would be allowed to castrate him and while his groin ached the thought of that was too much for him to contemplate.

Then suddenly his life got a little easier as at association as he served Charlie she told him that her, Jaz and Debby had got transferred to an open prison for the last few months of their sentences. Charlie squeezed his balls and said,” You are a good fuck and should be kept in here for life or until you are a broken husk! However we will not need you as in the open prison we get to go out during the daytime! Jaz has a friend who lives near to the prison! A sexy young man with a nice tongue and a keen dick and she knows precisely which drug gang would pay a lot to get him as he owes them loads of dosh! Well in return for his silence we will get to use his flat and also his body for our amusement! Should be a laugh! Now the rest of my crew think you are a normal honey so let’s keep it that way as I am sure your cock needs some rest!” Bob nodded and had to agree Charlie spoke the truth. The next day she and the other two were gone and it seemed that Sara took over running the gang even though as a gang it sort of collapsed. However Bob was still serving Miss Smith every lunchtime and six of Maxine’s solid crew every afternoon with his cock. For the two hours of association he knelt in front of his bed as ten girls took turns to sit panties down and legs apart and enjoy his oral devotion. They all assumed he was a girl and Bob knew he had a reputation as the best head giver in the prison and even felt pleased by this. He could not understand why Sara wanted to sell him so much and she just laughed when he asked her. By now he hated her but kept quiet as he was totally in her amazon power. Her sexual desire was amazing and every night after lights out for an hour at least he lay as she ravished him and then after he passed out she used him even more.

Another killing week passed and then just a Bob started to think about getting parole soon his life again got worse. Sara had him dressed in the morning when the fat middle aged officer Mr Lloyd opened the door and leered at them and said,” I was on duty last night and heard you two perverts licking cunt! Well I am going to report you and get you both shat on you bitches or tell me girls do you want to strike a deal?” Bob shuddered as Sara said,”What sort of deal? No let me guess we give you a blowjob and you shut up?” “Yes you bitch!” Sara smiled and said, “I am a top girl in here Mr Lloyd as you know! If I go on my knees for you I lose respect and I would rather face a charge of lesbianism than that! However my honey does as I say so she will knell and suck! Being a lesbian she is not very good at it so I will tell her what to do. Do we have a deal?” “Yes you bitch I would not stick anything of mine in your dirty pox ridden mouth!” “Okay but Mr Lloyd this is a one off ask again and I will set you up as well! After all surely Helga gives you head in return for the heroin?” “Shut up slut and get your bitch knelling!” Sara smiled and pushed the shocked Bob to his knees and knelt next to him and said, “This will not take long!” Bob shuddered in horror as Mr Lloyd unzipped his trousers and flopped out a small study dick. Bob looked in despair at Sara and saw from her wide eyes the idea of forcing him to give head excited her. She pushed the back of his head and neatly grabbed Mr Lloyd’s dick and stuck it in his mouth. Mr Lloyd became erect fast making Bob gasp as Sara pushed his head back and forth and to Bob’s total disgust within a couple of minutes he came and Bob was forced to swallow the slime down. As Bob knelt bemused Mr Lloyd zipped himself up and said,” Lesbian bitches! You are right Sara Helga gives much better head particularly if I make her wait for the smack for a few hours! Okay I will leave you two alone if you leave me alone!” and with that he stormed off. Bob stood and washed his mouth out as Sara smiled and said,” Even better! The bastard got gay head! He would kill you if he found out baby! Also baby after you had been castrated and were in the male prison apart from using your arse your mouth would suck cock all day long! You have to admit a pussy is a lot nicer!” Bob shuddered and agreed making Sara laugh.

From then on Mr Lloyd ignored him and Sara to Bob’s relief as he had hated giving a blowjob. However he was giving masses of head and being ravished every day by eight women so he was always sore and exhausted. His body hair had started to re-grow so Sara shaved it off but Bob was amazed his cover had not been blown. Then one morning Miss Smith came to the laundry and pulled him out and said, ”Shut it up when I speak boy or you will get hell!” and she made him follow her to the prison hospital. There they were greeted by the prison doctor Dr Wilde. She was a grossly fat woman in her fifties with a rank body odour of stale alcohol. She glared at Bob and said, “Miss Smith has told me you have a few bodily anomalies girl! Get that skirt and knickers off I want to look!” Bob blinked but Miss Smith nodded so he stripped naked below the waist aware of his plastic breasts. Dr Wilde approached him and grabbed his soft dick and rubbed it saying,” Miss Smith tells me this over grown clitoris gets hard! Oh yes it does and you know it does look to the uneducated as a penis but my trained eye tells me it is an overgrown clitoris! And you have body hair problems girl!” Bob nodded in confusion. Dr Wilde turned away and said, “You will be allowed a free ration of make up and a shaver to cover up this personal problem girl! I agree with Miss Smith that you should keep it quiet as the girls will comment and that could cause problems!” Bob nodded and knew somehow Miss Smith had struck a deal with the doctor. Then he realised it was in all the authorities interest to register him as female admittedly an odd female and Miss Smith was acting in both her interest and that of the prison.

This was confirmed when Dr Wilde said,” Now lie on the couch girl and relax! I want to test out this over large clitoris and see how it works! Miss Smith will wait outside!” Bob did as she had ordered and then shuddered as the grim ugly women removed her overall. She was naked underneath and her body was grey and wrinkled and her breasts had no shape as they hung down. She moved over and rubbed him and desperately he managed somehow to get hard. She climbed on the couch and he shuddered as her hairy smelly pussy was presented for licking. Bob licked away at her and then worse she moved and ravished him as he lay horrified on the couch. It took the old woman nearly twenty minutes to come and then once more she sat herself on his face and he licked her for the same amount of time rubbing her saggy breasts until she had a second orgasm. Then she climbed off and made him dress before saying, “You have been in the laundry room enough girl. Every morning now you will work here cleaning for me and I will help you with that overgrown clitoris!” and she leered at him. Then Miss Smith took him away and in his cell she ravished him three times. In the afternoon of course he had six of the solid crew to serve and then ten girls to give head to before Sara abused him to exhaustion.

The next day Miss Smith took him to the medical unit and he spent the morning washing dirty sheets and cleaning in a small side room. Many times during the tedious morning Dr Wilde visited him and pinched his bottom and made crude comments about his “clitoris” and twice she ravished him with her revolting body on a medical couch. Both times she got naked but only made the disgusted boy removed his panties and hold his skirt up. By the time he was taken off by Miss Smith he knew there were worse things than the laundry room. The next week passed in a blur of exhausting sexual service as with Dr Wilde in the morning to please before he was used throughout the day and for a large part of the night as well. However while he was battered and in pain and his dick was always red and aching Bob knew the days were passing and soon he would be free and able to leave the mad house and it was this that kept him sane and able to survive the constant usage, the abuse and the threats of castration. Sara used him every night and was now hardly bothering to disguise the fact she had deliberately tricked him into visiting to improve her position among the prisoners and Bob now hated her perfect body and her cruel manners and knew she was an evil woman.

Then one afternoon after serving Maxine and her crew and feeling exhausted as the black girls had forced four painful orgasms out of him Miss Smith took him to his cell. Bob gasped as all Sara’s stuff had gone and Miss Smith ordered him to pack his few belongings and follow her. Feeling sick he did as she wanted and when he asked what was happening she said,” A change of plan boy your girlfriend does not want you but I know a group of bitches who do! You are moving wings honey and serving another sexy gang!” Bob groaned as he was escorted by her to another wing and groaned as she marched him up some stairs and into a cell. Sitting on a bed was Maxine who smiled and said,”Hello pretty honey make yourself at home here. Thank you Miss Smith for bringing my toy here! Give Miss Smith a kiss of thanks Bobbie as you will be spending an hour dealing with her needs a day from now on!” Bob groaned and did so and gasped as Miss Smith put a hand up his skirt and pinched his balls. Then she left and Maxine smiled and said,”Welcome to my parlour said the spider to the fly! Relax baby I cannot wait until lights out and then you and I can have a full session of fun. I own you now not Sara and you belong to the solid crew! We are a much tighter crew than Nicola’s girls or even Charlie’s were and we stay together and one leaves as I will in a year we pass on to the next leader in our case Charlene! And honey bun four more girls have taken to oath of loyalty to the gang last week and I am going to let them in on our big secret! Your cock! So you will have a dozen crew girls to serve. Six in the afternoon in the education centre and then a few more in the evening followed by me at night! And baby you should have time to knell and please eight or nine girls a night as well in return for goods to the gang! What with Miss Smith and a few of the guards I think you will be in constant usage!”

Bob moaned as this seemed even worse than serving Sara and also he was worried about what had happened to her. Then Maxine ordered him to lie on the bed and dazed he did so. At that moment Charlene entered the room with four more large black girls. Maxine smiled and said,” Welcome sisters and allow me to show you the solid crew’s secret weapon and pleasure tool! And pulled his panties down and exposed his red semi erect dick. The four girls gasped and then were invited by Maxine to grope the poor body making him moan and get hard. Then one after another they removed their panties and presented their dirty black pussies for wetting on his tongue before each ravished him underneath their strong amazon bodies. After all four had come they took turns to enjoy him twice more in pairs having an orgasm on his tongue and then his dick. Three times Bob had sobbed in exhausted orgasm before the new gang members were finished with him and then he served Charlene and Beverley before lock up. As soon as the lights were out Maxine was naked and on him and for over an hour the powerful black girl battered his exhausted body until he passed out.

The next morning just like Sara Maxine woke him early and demanded oral pleasure before making him dress and make up. He was broken but worried about what had happened to Sara and about her telling. He knew trapped in a cell with Maxine he was in serious trouble but also knew if everyone kept quiet he would soon escape this nightmare of sexual slavery. In the morning he was taken to Dr Wilde’s area and three times she used him laughing at his performance with his “clitoris” then Miss Smith used him twice and when he asked about Sara she pushed her baton up his bottom in reply. Then she took him to the education area where he saw Maxine and two more of the solid crew. He expected to be naked as always on the mattress but instead they waited and ignored him.

To his amazement Sara walked into the room accompanied by Miss Smith. His surprise was that Sara was wearing a short skirt and a black top and not prison uniform. She smiled sat him and said, “Thank you Miss Smith for allowing me a few minutes to say goodbye to my special friend. And Miss Smith glared and left. Sara walked over to the amazed Bob and pushed a hand up his skirt and then into his panties and grabbed his balls and said,”Hello sexy boy! A change of plan baby I know you have fallen out of love with me no surprising as I got you in here! And as for me well you were only ever a toy boy to amuse me with! Now remember I told you that Maxine had adjusted the records to get you in for six weeks! Well she wants you to stay for years and I agree a boy makes life nice here! So we have changed the records around a little with the help of a few bribes both sexual and financial! To make it simple honey I have swapped your record with mine!” Bob moaned at that and felt Sara squeeze his balls as with a smile she said,” Of course the problem is the screws knew I had six years to serve but a fake letter told them I had been let out on appeal with the sentence reduced to nine months! Great I hate being inside! I am off to Spain with the money the drug deals made me baby and I am going to have a new life lounging on a beach and fucking boy after boy for my amusement! As for you well baby you have three years to go before you get parole and that depends on behaving yourself and Miss Smith wanting to let go of your dick! A perfect set up the prison roll and records all balance! I get freedom and the girls get a dick! The only loser is you boy and you get hell! You have to live in this shit hole as a girl serving without question which ever girl wants you or suffering hideous pain, death and of course castration. Do not worry honey it will only be for three or four years and then you can leave and maybe have a normal life if you are lucky! Now give me a nice kiss baby! No? Okay then have fun toy boy!” and with that she gave his balls a violent twist making Bob scream and collapse to the ground. Sara spat on him and said,”I will send you a postcard from Spain honey!” and then with a laugh she left the room.

Maxine moved over and pulled him up and said,”Three years as the solid crews toy boy and pussy licker honey! Remember if you get found out you will be castrated and then get hard time in the male prison as a bitch boy! As Sara said all the records both here and at central office read right. I sorted them here by selling the last honey and the cash we raised and Sara paid a big bride to a central office clerk! She gets out and we stay in but we get you as compensation so you had better be worth it honey! Okay let’s fuck we have wasted time this afternoon and I fancy a big orgasm!” The girls dragged Bob over to the mattress and flung him onto it. Then Maxine pulled her panties off and yanked Bob’s down and grabbed his tender dick and said,”We own this and if in three years you want it back it had better serve us and our many friends well! Okay let’s fuck I want a really big orgasm toy boy!” and as Maxine engulfed him he started to cry as he knew he was now trapped into years of hellish female servitude.