A hard game of chess.

my second story also from the 1990's (noter Jon not Bob!)

A hard game of chess.

A fantasy based on the familiar theme of losing a bet to a sexually aggressive girl.

It was a dull evening in the college chess club and Jon the colleges number two had already beaten three of the regulars. As the evening drew to a close Jon saw that a new girl member was playing one of the older female professors and losing badly. The professor was calling this girl Wendy. Wendy was short, red haired with a very nice pair of large breasts and a big sexy mouth. The professor checkmated Wendy and after a short conversation left. Wendy saw Jon and called him over saying " fancy a game ". Jon replied " no thanks I am to good for you". " Wanna bet," said Wendy. "I do not bet money," said John. " Okay how about sex " smiled Wendy. Jon was extremely surprised but thought to himself 'no way can I lose and she has got nice tits and I will enjoy screwing her tonight' so he said " okay what's the deal, You can have odds if you like ". Wendy paused and then said, " I am white. If you win I spend the week as your sex slave but if I win you spend a month as mine. To get your freedom you must win a game at the end of the month or it starts again. If we draw we replay you as white." Jon agreed quickly and at Wendy's suggestion the terms of the bet were written down and the game began.

Wendy started out very defensively and Jon soon launched a fast attack. However to his horror Wendy found a string of excellent moves and turned the attack around and he was in serious trouble. Jon tried to launch another attack but Wendy crushed it with ease and started to chase Jon's king up the board. Jon realised that he was lost and said to Wendy " the bet was only a joke okay? ". Wendy replied " no it's serious and if you do not pay up, I will publish it and you will be the laughing stock of the college". Jon considered his position, the game was lost, but it would not be to bad to be with Wendy even if she was in charge, I mean what harm could he come to and sex was good sex. Therefore Jon with a smile resigned and said, " I am in your hands now but wait till next time". Wendy grabbed his hand a led him out of the club.

After a short walk they arrived at one of the girl's residential blocks and went in and up to Wendy's room. When they were in the room Wendy pulled Jon onto the bed and they started to kiss him. Her hands groped his arse and Jon responded by touching her large heavy breasts. Wendy stopped kissing him and said, " No I am in charge I grope you and you take it. When I want stroking I will tell you" with that she pushed his hands away. They started to kiss again but now it was Wendy's tongue aggressively in Jon's mouth. Her hands unzipped his fly and pulled his rapidly erecting member out she looked down and said, " nice dick I'm glad I own it. We are going to have so much fun". With that she started to rub his dick between her fingers after a minute of this Jon started to moan and push himself against her hand. Wendy took him to the brink of coming and then let him go. She looked at the excited boy and said, " not yet darling. Do you know I love it when a man strips for me." Wendy pushed Jon up and said "striptease time get naked and make me wet!" Jon started to dance in front of her and to slowly remove his clothes. As he danced Jon felt embarrassed and he felt worse as he got more and more naked, however it obviously turned Wendy on so may be he would screw her soon? When Jon was down to his boxers Wendy jumped up and pulled them off him with a laugh, she then pushed him on the bed and flung herself down on top of his naked body.

Wendy kissed the naked boy roughly and pushed his hands up and before he could react she had produced from under the pillow some handcuffs and attached his hands to the top of the bed. Jon was amazed but before he could speak Wendy lent down and started to lick his dick and balls from top to bottom. However as he started to moan with pleasure she got off his and body and walked over to a chest of drawers.

Wendy returned with a camera and before he could react she had taken several photos of him tied, naked and erect. She put the camera down and produced from the draw a handful of women's clothing saying, " I love a sissy boy." As Jon tried to resist her she smacked him hard on his naked behind and managed to grab his balls saying, " can it cutie I want some more photos to make certain you will keep your side of the bargain". Jon lay still as she dressed him in black stockings and suspenders with a pair of red crotchless panties and a red mini skirt. She then played with his dick until he was moaning with excitement and then posed him with the skirt up and took some more photos. When she had finished she left the room. After a few minutes she returned without the camera to Jon who had now lost his erection as he realised what she had done to him. Wendy started to stroke his dick and as she got him excited and hard she said " I have the photos nice and safe and only I can see them. However break the bet and they go public. Do you want to go? Or stay as my naked love toy?" Jon realised that he had no choice but to stay and do as she wanted and he sadly agreed.

Wendy removed her top and bra and let her large white breasts drop over Jon's face. She said "lick them gently as I direct" and with her hands started to push Jon's face around. Jon licked them and after about ten minutes he noticed that she was getting highly excited, he hoped that they would screw soon and his hopes were raised when she stripped off. However it was not his dick that she went for but his face which she pushed into her wet pussy. Wendy's pussy smelt feminine and she had obviously not washed it for sometime but Jon was forced to hunt out her clitoris and lick her. As her excitement increased she slammed herself against his face and crushed his head between her strong thighs. Jon desperately licked away hoping that she would come before he passed out. Eventually she came with a scream but she did not stop but kept on going until Jon had pleased her five times by then he was dizzy with wetness and exhaustion.

Wendy undid the handcuffs and said to him " let's go and clean up". She grabbed him by the balls and pulled him towards the door. Jon was horrified that someone would see him, dressed as he was in women's clothing, but as it was late the passage was empty. They went into a bathroom with a toilet and shower inside. Wendy said, " strip off those clothes." When he was naked she placed the clothes in a bag and then she sat on the toilet she smiled and said, " knell and come here I have got a surprise for you." Jon assumed that she wanted more oral sex and did as he was told however as he put his face between her legs she squeezed his head with her thighs so he could not move. Jon was horrified as she then emitted a stream of strong yellow liquid into his shocked face and he choked as some entered his mouth but she held his head firmly in position. When she had finished she told him " lick me clean" Jon licked the remaining drops off her thighs and cleaned with his tongue the thick pubic hair.

When Jon had licked her clean she pushed him into the shower and turned it on. Wendy joined him and started to wash him with some soap and told him to wash her as well. Soon both were covered in soap and Jon was excited again. Wendy turned him to face the wall and started to rub his arse with the bar of soap. Then Wendy pushed the bar up his back passage. As Jon moaned with pain Wendy said, "shut up wimp I want you clean" and with that she pushed it in and out rapidly. After a minute of this Wendy pushed it deep into him and forced him to knell and start licking her again. Jon was knelling water pouring over him with the soap hurting his arse, as Wendy took her pleasure not once but three times.

When she was finished Wendy got out of the shower and got Jon to dry her. She then pulled him into the luckily empty corridor naked with the soap still in place and back into her room and handcuffed him to the bed. Wendy then grabbed his balls and started to squeeze. Jon moaned in pain and begged her for mercy. Wendy stopped and picked up something from under the bed and before Jon could react she had placed it over his flaccid dick and tightened it up. Jon looked down and saw that his entire dick was fixed inside a metal tube with a gauze like opening at the end. Wendy stood up and said, " this will keep you pure cutie. If you get hard the pins inside will soon make you soft. Let me show you". With that comment she started to stroke his chest and balls and rub his face with her breasts. Jon was soon getting excited but as he got hard he felt the sharp pins start to dig into his dick and the pain make him lose his erection. Wendy continued to play and six times Jon went through the cycle of erection and pain before she jumped astride his body and forced his tongue into her pussy and made him lick her to another orgasm.

Wendy sat back of the exhausted boy's stomach and playing with his nipples said, " Not a bad beginning. You may go now but from now on you will wear women's underwear and shave your legs and pubes. The tube and photos will keep you true for the next month of sexually slavery. May be at the end of it you can come but you will really have to work to earn that." The shocked Jon said, " yes but if I can beat you at chess I get my freedom and when you played the professor you were not very good". Wendy smiled and said, " I love a stupid slave. Don't you know that I am the women's world number 4. The professor is my coach and was helping me to trap you. You will be serving her with your tongue as well as satisfying all my desires and you will never win your freedom. Now go shave, sleep and think of ways of pleasing me to earn an orgasm next month." Jon left with the soap still in place and the tube digging into his dick. He was exhausted, defeated, frustrated and terrified of what was still to happen to him under the control of a superior woman. He started to cry.