Doing the rounds. (Part two)

Doing the rounds. (Part two)

Also from 2001

A fantasy based on performing for a woman in different places..

Bob a nineteen year old college student had been dating Jo also nineteen for several weeks and had taken part in a bet with her. The price for losing was to give Jo one thousand sessions of lovemaking under her control. In part one Bob started to pay off his debt. It is now the holidays and in return for counting it as a hundred sessions Bob has agreed to spend it with Jo as her sex slave. Bob cannot escape Jo because not only does she have embarrassing photos of him but also more importantly he loves her and desperately wants to be with her even through sexually her demands scare him.

Bob was pleased when he got to Jo's house. He had not seen her for a week but before she had left him she had fitted a chastity belt to him. When the taxi dropped him off all he had on him was a suitcase with two sets of his clothing and several sets of second hand girls clothing that Jo had purchased for him. He felt randy, apprehensive and wished to have the chastity belt taken off as it was rubbing him most painfully. Still Jo greeted him at the door with a big kiss and she looked incredibly sexy wearing a white cut off top and a matching mini skirt and stockings. Bob knew that Jo lived with her mother Sandra and sixteen-year-old sister Kim. All were slim and blonde. Kim was probably more stunning than Jo as her breasts were larger and more prominent even through Bob believed that Jo's were the best in the world. However Kim's face was not as attractive as Jo's as it was harder. Sandra also had a fine figure however age and gravity had affected her skin and breasts but she was definitely a mature looker. No man lived in the house and Jo's father had left under acrimonious circumstances many years ago.

When Jo got him in she pulled him into her bedroom and said, " This is where we will be sleeping for the next three weeks exciting?" Then she sat on the bed and pulled up her skirt. She was not wearing any panties and Bob was able to see her beautiful pussy that was already wet. Jo said " strip and suck lover boy." Bob removed his clothes but as he got excited the chastity belt pinned his dick and he moaned with pain. Jo smiled at him and said, " oh dear painful when you get hard is it. If you lick me to heaven maybe I will allow you to take it off." Bob knelt and started to lick her stunning pussy and within seconds Jo had a massive screaming orgasm. Bob realised that she had not had pleasure since the end of term and this thought made him even more excited and increased the pain in his dick. He struggled to continue to lick her golden temple of delight and in the next ten minutes gave her two more powerful orgasms as his dick suffered. When she was satisfied Jo pulled Bob on to the bed and started to rub his body and his trapped dick. Bob moaned she said, " Okay you promised to serve me and if you agree to do whatever I want for the next three weeks we can take that off. I have shown your photos to mum and Kim and we had a good laugh at them. You will do what they demand as well and also we are going to keep you naked or dressed as a girl. If you need to wear male clothes you will wear the belt. However most of the time you will be doing housework as we think this house needs a good cleaning and what better than a slave to do it. Do you agree?" Bob had no choice but to say yes. Jo went and got the key and released the poor boys dick, which sprung erect. She played with him and he was rapidly on the brink However Jo kept him on the point of coming for ten long minutes until he was convinced that he would die then she rubbed him over the edge and he exploded with a loud scream of pleasure.

When he had recovered she pulled him into the bathroom next door and under a shower then as Bob watched she stripped off her clothing and exposed her perfect body. She joined Bob in the shower and soaped down his body. The feel of her fingers on his skin soon had him hard again. Jo smiled and started to play with his dick until she again had him on the brink of coming then she pulled down the shower hose and to Bob's horror turned on the cold water to full and fired it at his dick. Under the influence of the freezing water Bob soon lost his erection. Then Jo put the hose down and started to rub him again. As Bob expected when he was near to coming she again froze him soft with the hose. Six more times he suffered as she teased his dick. Then she replaced the hose and warmed up the water she said, " A fun little game. Now wash and clean me. I want you to use your tongue." Bob started to lick her back and then knelt and did her feet and legs. When he started on her pert backside he noticed that she was gently rubbing her clitoris she said, " Spend a lot of time on my arse and make certain your tongue goes right up me." As Bob obeyed and started to lick her she started to push her buttocks against his face and then with his tongue deep within her she came with her fingers rapidly rubbing her clit. Then she turned around and said, " Now lick my front baby!" Bob started to lick her stomach and then moved up to suck on her beautiful breasts after several minutes she pushed him down and rammed her wet pussy into his face. Bob applied his tongue to her clit sucking and licking it and in less than a minute she came screaming and flooding his face with wetness. Jo pulled Bob from the shower saying, " That was great. We will do that again very soon but now I am satisfied so lets have a lie down." They returned to the bed and lay down together. Jo pulled Bob close to her wet naked body his dick was rock hard Jo said, " I want to sleep but you can masturbate into your hand. However when you come make certain you lick all your spunk up as I do not want a mess on my bed." Jo closed her eyes and fell asleep on Bob. Bob looked at her wonderful body and then started to rub himself thinking how nice it would be to have normal sex with Jo and not put up with her kinky demands.

Before Bob could come he heard a hiss and looking up he saw Kim in the doorway. It was obvious that she had been watching him masturbate. Kim beckoned him to come with her and Bob got up and left the sleeping Jo behind and followed Kim into her bedroom. Kim closed the door and pushed the naked boy onto her bed. She said, " Hi Bob. Remember me? I loved your photos! Now did Jo say you could masturbate or were you being a naughty boy?" Bob gulped and assured her that Jo had given him permission. Kim said, " I will check when she wakes up. Now I am here however you can put on a sex show for me. I want you to dance play with yourself and rub your dick with what I tell you." Bob did as she ordered and was soon near to coming even if the humiliation of dancing for an attractive girl was distasteful. As Bob danced Kim removed her top and then her bra allowing Bob to admire her large sexy breasts and her erect nipples. She handed her bra to Bob and told him to rub his dick with it. Kim stroked her breasts as she looked at Bob dancing then she removed her shoes and made Bob rub his excited penis with them. Then she removed her panties and again Bob rubbed himself with them as he danced for Kim's pleasure and entertainment. Then Kim lay back on the bed exposing her tight pussy to Bob's gaze. She raised her legs out together and said, " Put your dick between my feet and move. Bob put his dick between her feet and started to move it in and out between them. Bob looked along Kim's sexy body at her pussy and breasts. Then Kim put on hand down and started to masturbate herself while the other hand squeezed her nipple she said, " When I come you come or I will rip your arse open slave boy." Bob moved his dick between her feet the sensation of it getting him close to say nothing of his earlier session with Jo or the sight of a stunning blonde masturbating in front of him. As Bob struggled not to come Kim became excited and to Bob's relief came with a scream pressing her feet hard together against his dick which allowed Bob to join her in a moaning release his spunk shooting out and splashed up her legs some of it reaching her knees. Kim looked at Bob and said, " lick my legs clean scum head!" Bob started to lick his come off her long legs and when he was finished Kim grabbed his head and pulled it into her cunt. Bob started to lick her tight sticky pussy and after several minutes of his oral attention Kim came with a low moan. Kim said, " This holiday is going to be such fun with a live in love toy. We should have had one a long time ago. Now go back to Jo I will use you latter toy boy." Bob left her and returned to the sleeping Jo and fell into an exhausted slumber next to her beautiful body.

Bob was awoken by the feel of female fingers on his dick and awoke to find Jo and Kim dressed and playing with his body Jo said, “ Soon be time for dinner. Let’s get you dressed.” Kim opened his suitcase and took out the woman’s clothing, which was in it she said, “ Oh excellent. He will make a wonderful sissy toy .Let us dress him in this!” She produced a pink short frilly night-dress and Jo said, “ Perfect he does not need much as I want to look at his dick tonight.” The girls placed the humiliating clothing on Bob and Kim said, “ Time for dinner, come on let’s go down “ and they pulled him out of the room and downstairs. When they got down stirs the girls mother Sandra was waiting she burst out laughing when she saw the blushing boy dressed in a pink night-dress and said, “ Oh excellent well done Jo. He will be real fun to have around for the next few weeks. Come on let’s eat and maybe then Bob can provide some after dinner entertainment.” They sat and ate a simple supper. The women talked about neighbours as Bob sat embarrassed and unable to eat. When they had finished eating Bob was made to clear the plates away and he was horrified to see that the kitchen was full of dirty saucepans and plates Sandra said, “ Tomorrow you can clear this up. But for now come on through as we want to see you dance and sing.”

Bob went into the lounge and the women sat down in the chairs with coffees Jo said, “ Okay sexy. Dance and play with your dick. Remember to smile we want to be entertained.” Bob started to dance and rub his dick and after a few minutes he was hard and able to forget the sheer humiliation of the situation. However Jo increased his humiliation by producing a small dildo and saying, “ Add some arse play to your dance and a bigger smile. “ Bob was forced to insert the dildo into himself as he danced and then Kim called him over and roughly pushed the dildo hard into him causing him to moan with pain. Then she grabbed his balls and made him dance in front of her as she squeezed them. After several minutes of this Sandra pulled him in front of her and said, “ Come on young man. Shake your dick and make me smile.” Bob was forced to vigorously dance for the older women as her and her daughters made witty and rude comments about him. After a couple of minutes Sandra started to grope and fondle his body and Bob blushed with embarrassment. Finally Jo called him over and he danced in front of the woman he loved her hands however were not gentle as they pinched and squeezed his body. It was thirty minutes before the women allowed Bob to stop his humiliating dance and to sit down next to Jo who immediately started to snog and masturbate him. As Bob approached orgasm Jo slowed and kept him on the edge of coming for another thirty painful and embarrassing minutes. During this time the women talked normally as if it was a daily occurrence to have a boy dressed in a night-dress on the edge of coming sitting in the lounge. Then Jo said, “ I think he should come now but how?” Kim replied “ Masturbating into a glass on his knees while one of us manipulates the dildo in his arse. “ Jo laughed and said, “ Excellent come on Bob get ready to show us what you are made of. “ Bob was forced to knell and hold his erect dick into a glass then he felt Jo seize the end of the dildo and start to move it in and out of him she said, “ Bring yourself off my cute little sex toy.” And with his other hand Bob started to rub his dick. Bob had never been so embarrassed and found it difficult to come however the feel of Jo’s body near to his and the sensation she was producing on his prostate finally produce an orgasm and he fired into the glass as the women looked and laughed. Then as he expected he was forced to drink his own come again to the general amusement of the women.

Sandra said, “ I am off to bed. What are you girls doing?” Jo replied “ We are going to watch the late horror movie. Why don’t you take Bob with you and get him to give you a good massage. “ Sandra nodded and beckoned the tired boy up the stairs and into her large bedroom she said, “ Strip and lie on the bed. I am going to wash. “ Bob did as she requested and was relived to remove the dildo and night-dress. After ten minutes Sandra returned. She was wearing a long white nightie and had removed her make up, which made her look both older and younger. Her body was firm and in the night-dress it was difficult for Bob to believe that she was as old as he knew she must be. She lay down beside him and started to stroke his chest saying, “ Poor little boy so abused by us violent demanding women. I bet you want to go to sleep but you have me to serve and then I am sure my daughters will want more” Bob moaned and she added “ Do you love Jo?” “Yes” “ She can be very hard but basically it is because she feels insecure and she will test you to the limits. I am afraid that she will always be like that. I blame her father however it is Kim I worry about she actually enjoys causing severe pain to boys. Still lets not talk any more I want you to go down on me and give my pussy a good licking. “ With that comment she pulled up her nightie and pushed Bob down her mature body. His tongue found her cunt which she had obviously washed clean and started to lick her clitoris and vagina as he did so her hands started to gently play with his dick and balls. It took Sandra a long time to become wet and excited but when she did she had a long series of rapid and powerful orgasms on Bob’s tongue. Her hands had brought him close to coming but before he did so she said, “ Thank you. Go downstairs and please my daughters now. Latter this week I am having a bridge party here for myself and some friends you can be our waiter, stripper and pleasure toy.” Bob left the satisfied women and went downstairs he was exhausted in body and mind and worried ‘Jo was testing him but could he survive? And what horrors could Kim inflict.’

When he got downstairs he saw the girls were watching television Jo saw him and said, “ Come here darling and suck me off” Kim said, “ I want him now as well!” Jo smiled and said, “ That’s okay he can lick me and stroke you. Get serving cunt slave!” Bob knelt in front of Jo’s stunning pussy and applied his tongue. As he licked Jo Kim grabbed his hand and pushed it into her wet pussy and he was forced to gently stroke her clitoris with his thumb as his fingers slipped into her vagina. As Bob worked the girls became excited and during the next thirty minutes Jo had three orgasms and Kim had two. After she had come for a third time Jo pushed Bob away and Kim said, “ If you’ve finished with him I will take him upstairs as I need a lot more pleasing.” Jo said, “ Okay I will watch the end of the movie. When you have finished send him to my bed.” Kim grabbed Bob by the penis and balls and pulled him up to the bathroom.

Kim pulled Bob into the shower and then she stripped and got in with him she said, " Knell I want to piss on you. " Bob moaned and did as he was told. Kim pulled his open mouth up to her pussy and let loose a stream of yellow liquid into his mouth. Bob choked and spluttered but was able not to swallow any of the foul liquid even through it filled his mouth. When she was finished she pulled him close and Bob was forced to lick her. Firstly he cleaned her pussy and pubic hair and then he licked her to a powerful orgasm. Kim got out of the shower and said, " lie down slut. I want to watch you piss all up your body. Kim lent down and grabbed his dick and pointed it upwards and said, " Now piss " Bob struggled and then he started to piss. The liquid poured over his body as Kim laughed at him. When he was finished Bob was lying wet, dirt in a puddle of foul liquid and feeling seriously humiliated. Kim smiled at him and then she spat in his face and said, " Shower and go to Jo's bed. Tomorrow I am going to really humiliate you." Bob washed himself clean and then went into Jo's room.

The next morning Bob was awoken by Sandra rubbing his dick she said” rise and shine time for work. You can do it naked.” She took him downstairs and into the kitchen and handed hi, a piece of paper full of chores for him to do saying “ This is today’s list. Kim will keep an eye on you and punish you if you slacken.” And left obviously for work. Bob groaned and started the long list of tasks. All day he washed scrubbed and polished occasionally Kim or Jo disturbed him but in general he laboured alone. Bob was horrified weeks of sexual humiliation and domestic slavery. In the evening Jo cooked a meal for the family in the now pristine kitchen and Bob served and cleared up before eating himself. Bob was exhausted and surprised when he saw that Jo and Kim were dressed to go out they said, “ Come on let us get you ready. “ and dragged him upstairs. They dressed him in a long pink dress, panties and a stuffed bra and then made his face up. Bob now looked in a dim light female.

Kim, Jo and Bob went out in a taxi. They arrived at a club which had a large sign – Ladies night! Naked men for your entertainment! And went in. Bob was horrified to sit down dressed as a girl in a roomful of women. However his cover was not broken and then the lights went down. A man dressed as a cowboy appeared on stage and to Bob’s embarrassment stripped and danced with the women in the audience. The audience started to whistle and scream as more men appeared and stripped for them. Bob was seriously embarrassed and worried about what would happen if he were found out. After an hour Jo who had been drinking heavily said, “ Bobbie I am randy. Let us go to the loo and you can lick me!” and dragged him off. They entered the bathroom and went into a cubicle. Jo raised her skirt and removed her black sexy panties exposing her golden pussy as Bob knelt and applied his mouth to her pleasure. She came quickly and noisily but Bob was forced to carry on until she had come three times. Then they left the cubicle. Outside were four large middle aged women obviously the worse for drink. One of them said, “ Hey girls that’s a bloody man!” Jo replied “ Yes it is my sissy love slave! He has a nice tongue. If you want you can use him for a bit. Tease him, use him, abuse him but do not let him come!” and left him in the bathroom with the drunk women.

The large women grabbed Bob and pushed him to the floor ripping off his dress and laughing. Then one of them a fat dark haired woman pulled up her skirt removed her panties and sat on his face. Bob choked and was forced to lick her large fat sweaty pussy. As he did so the other women assaulted his body. He felt rough hands on his penis and balls and felt fingers ramming into his anus. Eventually the woman on his face came but was replaced by another equally fat and disgusting and Bob was forced to lick her. He satisfied her and then the other two all the time the rest of the group abused his body. When all four were satisfied the first women said, “ Lets piss on the sod to show him what we think of men!” She squatted over Bob and another women grabbed his balls and squeezed until he opened his mouth then she pissed into it flooding Bob with foul liquid. It got worse as the other three took turns in pissing on the unfortunate boy. Then Bob was turned over and one of the women a greying blonde produced a large dildo which she rammed up his behind saying, “ You want to be a girl this is what it feels like now wiggle and say how you love it!” Instead Bob screamed in pain and begged for mercy the woman kicked him in the balls saying, “ No pretend you love it fuck yourself with it!” Bob rolled in agony but he had no escape and was forced to knell and bugger himself pretending that he was excited. After five minutes of this extreme humiliation the woman removed the dildo and Bob collapsed in pain on the floor. The women started to kick him around the floor trying to hit him in the balls and landing many agonising blows until after a few minutes they became bored and left. Bob pulled his battered body off the floor and quickly hid himself in one of the cubicles to escape any more assaults. For the next hour he lay in the cubicle his body racked with pain until he heard Kim calling and was forced to let her in. She smiled at his shattered body and pushed him to his knees. He applied himself and licked her to a rapid orgasm. Then Kim forced him to dress in his soiled female clothes and pulled him back into the hall.

When they arrived back at the table Jo was sitting with three other young women. Kim said, “ The coward was hiding. I think he was no match for the others. Now darling get down under the table and pleasure lick us. You can start with Jo! Make it good or we will give you to the previous group for a whole night!” Bob knelt under the table. Jo had removed her panties and Bob started to lick her. She came fast stimulated by Bob’s tongue and the naked sexy men dancing on the stage. Then he moved to the next pussy it was hairless and small but he was able to rapidly enlarge and pleasure it until he could hear the girl coming loudly. The next women had a hairy and already very wet pussy with a prominent clitoris. Bob licked and sucked her clitoris and her hands pulled him close as she came fast and screaming the sound of her coming drowned out by the noise in the hall. The last girl had a large tight pussy but again as she was excited by the drink and the naked men Bob was able to bring her off quickly. Before he could please Kim the strip show was over and the lights went up. Kim quickly pulled Bob up and they left the club. Kim said to Jo “ We are going on a man hunt at the local disco. Our toy has warmed us up. We are going to pick up a bloke and make him lick us off as we rape his arse with a bottle. Then we are going to piss on him, crush his balls, twist his dick and leave him naked and humiliated to get himself home as best he can. He will never doubt the superiority of women after we have finished with him.” Jo laughed and said, “ Have fun. I will take Bob home he has a busy day of housework tomorrow and a busy night between my legs before I let him sleep.” And dragged Bob into a taxi and took him home.

Bob and Jo got in the taxi and left Bob lying semi-conscious in the back. Bob was aware of Jo talking to the taxi driver and explaining all about him. As he looked at the driver he realised that she was female. She was large, tough looking with tattoos on both her thick arms with short greasy black hair and a flat ugly face. Jo was calling her Debra and laughing as they joked about him. When they got to Jo’s house Debra said, “ Jo you can have the fare for free if I can borrow your slave for an hour to please me and my friend Flo. “ To Bob’s horror Jo replied, “ Deal, He is yours for one hour. He can come but no intercourse.” And got out. The taxi drove off with Bob in the back. Debra drove for a couple of minutes then pulled off the main road and up a deserted track and stopped. She spoke on the radio saying, “ Flo stud lane quickly. I have got a live toy for us to enjoy.” And then said to Bob, “Climb into the front and go down on me!” Bob did as she ordered and Debra pulled off her pants exposing a large hairy pussy. Bob knelt on the floor of the taxi a very uncomfortable position and Debra pulled his face tight against her. His tongue searched in her smelly thick pubic hair and found her clitoris and started to lick her. As Debra became excited she started to push her body against his face until after five minutes her hips were pushing Bob’s face high and bashing the back of his head on the steering wheel. Bob was in agony as his head suffered and his face was jammed into her wet pussy he was pleased when with a loud scream she exploded and came. As Debra relaxed back they heard a voice saying, “ Nice one Deb’s. “ and as Bob looked up he saw a women in her forties looking in. He assumed it was Flo who was tall skinny with very small breasts and a lined face. Debra said, “ let’s get out “ and pulled Bob out. Flo grabbed him and forced her tongue down his throat. Her breathe smelt of smoke and Bob was not aroused even worse her hands twisted his penis and he felt Debra’s fingers enter his arse and abuse him.

After a couple of minutes Flo said, “ Okay sissy boy strip and rub yourself off. We want a good show. “ Bob was pushed to stand in the taxi headlights. As the women laughed he removed the female clothing he was wearing and danced naked in the car lights his hands stroking his penis. After a couple of minutes he was getting excited but he heard Debra say, “ Cut, come here and please us!” Bob walked out of the lights and saw that the women were sitting on a blanket watching him. As he got close he was pulled down and onto his back. Debra said, “ Your dick is not allowed in our pussy’s but your shaft can rub my clit!” She mounted him and grabbed his dick and started to use it to masturbate her clitoris and pussy. It was a most uncomfortable sensation for Bob and it got worse as Flo removed her clothes and mounted his face and dropped her hard smelly pussy against his face. Bob started to lick Flo and her pussy soon became extremely wet on his face. He could feel Debra using his dick and the sensation was not that uncomfortable even if her pubic hair scratched his penis. After a couple of minutes both the two women came together on top of Bob. However they did not stop but continued to use him. It took another ten minutes before Flo came for a second time on Bob’s face. She pulled off him and lighting a cigarette sat back to watch Debra using him. It took only a few more minutes before Debra had a massive loud coming as she vigorously rubbed his dick against her clitoris. This was also exciting for Bob who was on the point of coming and when Flo lent forward and gently rubbed his dick he exploded shooting spunk all over his body. After a couple of minute’s rest Flo left and Debra picked up the exhausted boy and threw him into the back of the taxi. Debra drove him to Jo’s house and then dumped him on the doorstep naked, exhausted and battered. Bob lay groaning and trying to think how he could survive the rest of his stay.

Can he survive?