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Not sure if this post belongs in this forum. It's a story I wrote. It's fiction, but the sex it contains is a modified version of my first encounter with a shemale. Hope you enjoy:
It was Friday night, and Michael sat in the student pub, alone. He should be out with his friends, having a good time. But he was all alone. The evening started normally enough. But things had quickly turned sour. Kimberly had clued him in right away that something was wrong.
"You asshole," she had said, not mincing words. "Did you write that fucking letter to the editor?"
"Look, it's not like you think, o.k.? I meant it as a joke."
"Here's my joke," said Kim, dumping an almost full pitcher of beer on him. His former friends all took this as their cue to leave. Michael was left alone trying to dry himself off with paper napkins.
He was surprised that the letter to the editor of the student newspaper had been so badly received. His subject was poorly chosen, given that he was in Toronto. Perhaps there were universities in the United States where an anti-gay, anti-transvestite diatribe might be received with mirth, but Toronto was rather different. The letter had been printed the day before, and he'd committed a blunder of the worst kind, and he could look forward to a rather solitary existence at U of T for some time.
But not all of his friends had deserted him - Angie, a medical student arrived at the pub just in time to see the drink dumped on Michael. Grabbing some paper towels, she came to help.
"She got you really good," said Angie, drying his hair. "What did you say to her?"
"It wasn't anything I said. It was what a wrote."
"That letter in the school newspaper?" said Angie.
"Yup," said Michael. "Some people just can't take a joke."
"You're just too soaked to dry off here," said Angie. "My apartment's only a couple of minutes from here. You're about my boyfriend's size, and he keeps some of his clothes at my place. I'll lend them to you." Michael expressed his gratitude, and followed Angie out of the pub, his ego deflated by his public humiliation.
"It's nice of you to bring me here like this," said Michael. "Aren't you afraid your neighbors will see you bringing a guy home who's not your boyfriend?"
"Not at all," Angie replied. "Even if I worried about that kind of thing, it's Friday night, and I'm sure no one's around." She handed him some clothes and a towel. and showed him the door to the bathroom. When Michael emerged a few minutes later dressed in borrowed clothes, Angie was sitting on her bed, with two mugs of hot chocolate. There was nothing suggestive about her sitting on the bed -the apartment was very small, and the bed doubled as a sofa.
"Don't leave until you hair is dry," she said, passing Michael one of the mugs. He sat next to her, gratefully accepting the drink. Angie had changed her clothes too, and now was in her pyjamas and a robe. She was a stunner, thought Michael, no doubt about that. Almost his height, with very long, wavy black hair, grey eyes and a perfect figure. They made small talk as they drank their drinks, Angie laughing at his jokes. At one point she leaned forward as she laughed, inadvertently displaying her cleavage. She sat up suddenly, and Michael was not quick enough at averting his gaze. Caught looking, he felt himself blushing.
To his relief, Angie laughed, and then kissed him.
"I have this thing where I have to be the one in charge," said Angie. "It's my body and my place, and you have to play by my rules."
"Deal," said Michael. He removed the jeans and underwear at Angie's bidding, and lay back on the bed, his eyes closed.
"Before we get started, we need the cuffs."
"The what?" said Michael, surprised.
"Yes, the cuffs. You do want to make love to me, don't you?
Michael quickly confirmed his wishes in this regard, and so allowed himself to be cuffed. Angie didn't cuff his hands together, but instead attached him to a short steel rod which hung from a cord fastened firmly to the top of the bed frame. He watched quietly as she cuffed his legs at the ankles, the cuffs joined by a length of chain. Had he been able to stand, he would have been able to walk, but running would be out of the question. Michael looked up at Angie, a smile on his face as she let her robe fall to the ground, and took off her pyjama top, treating her guest to his first view of her perfect 34B breasts.
"I think it's time for a blowjob," said Angie. "What do you think?" Michael was in full agreement. There was no doubt about it, in his view. He closed his eyes and lay back expectantly.
"That's great," said Angie, as she began to pull down her pants. "It is blow job time, so open your mouth."
Michael began to laugh, and opening his eyes, turned towards Angie.
"What the fuck? WHAT THE FUCK?" he shouted, for only a few inches from his face bobbed Angie's cock, easily the same length as his own, hard, turgid and demanding. His exclamations of horror became more frantic as he sensed Angie trying to shove something in his mouth - a ball gag. She put a knee on his chest, both to pin him down and inflict pain, and as he grunted in agony she fastened the straps on the back of his head. She stepped back to take in the view.
"It's really a bore having to put a ball gag on you," she said while she set up a camcorder on a tripod. "I'd much rather you be able to talk, and I think you'd rather be able to talk, too. It's not that I'm worried anyone will hear you - we're in the basement, and no one's around. It's just I find it distracting. Now can I trust you to keep your voice down?"
Apparently not. Moving forward, she grabbed his hair with her right hand, and firmly closed his nose with her left. Instantly Michael's air was cut off. She only let him experience this for a few seconds, and then relented.
"Let's try this again," said Angie. "Can I trust you to keep your voice down?"
This time the answer was a yes, for Michael had not enjoyed the feeling of being suffocated, even for an instant. He lay back meekly as his captor removed the ball gag.
"That's better. Now what about that blow job?"
"Please don't do this to me," said Michael, but in a whisper, desperate to keep the ball gag out of his mouth. "Please - I'm just not in to this."
"Then I'll let you go," Angie replied. "Once I've made sure I don't turn you on, that is. If you can stay soft, that will prove to me that you're not turned on, and that I should let you go." She stroked him, and Michael despaired as he felt himself immediately return to tumescence against his will, his cock aching and harder than it had ever been before. While this shocked Michael, Angie was not at all surprised, for the hot chocolate she'd given Michael contained a ground-up Cialis pill.
Angie moved back down the bed, giving Michael's cock a gentle tug as she did so.
"Mr. Happy's pretty hard, if you ask me," she said. "So you can cut the bullshit. Let me ask you - is it possible for a guy to have a rock-hard cock if he's not turned on?"
Michael's 'no' turned into a moan as Angie briefly took his full length into her mouth.
"You shouldn't have fibbed, Michael." He flipped over on to his stomach when she ordered him to.
The room was almost silent, the only sounds the gentle hum of a refrigerator, a car driving by, and then the plastic rustle of a package being opened, like someone opening a chocolate bar. After a short pause, the sound was repeated, and then Angie was lying between his legs.
"Some lubricant will make things a bit easier," she said. "I assume this is the first time you've been fucked."
"Please - not this - I beg you - I'll suck your cock I will please Angie don't fuck me please-"
"Shut up, Michael, unless you want to be gagged." Her middle finger, covered in a rubber and well-lubricated, snaked into Michael's ass.
"God you're so big Angie fuck that hurts, please stop-
"Michael, if you actually think that's my cock, I pity you. I'm just lubing you up with my finger."
"Nooo" said Michael, softly, silencing himself for fear of the gag. And then he felt Angie at his entrance, the head of her cock ever so much larger than the finger that had just penetrated him. He shoved his face into a pillow to stifle a scream as the invading cock violated him, pushing past the sphincter muscle, Angie's cock now buried in his ass.
"Oh god Angie that's so fucking huge I can't take it any more!" he whispered.
"Bad news, Michael - that's just the first inch. Here's the rest." And with this, Angie slowly but firmly worked the rest of her cock into Michael's tight and unwilling ass. In him now to the hilt, she began to fuck him with abandon: the quick, hard strokes of an experienced lover. Michael involuntarily let out a gasp with each repeated penetration, his insides feeling ripped open. The agony was incredible, and he could take no more.
"Please Angie Please stop oh please stop I'm sorry I'm really sorry!"
"What was that?" asked Angie, pausing on the down stroke.
"I said I'm sorry."
Angie pulled out of him, flipping him onto his back, his legs spreading like wings on either side of him as she once again positioned herself at his entrance. In this position, it was much less painful. Once the head of her cock was past his entrance, he felt very stuffed and uncomfortable, but not really in pain. He opened his eyes to see Angie's beautiful face above his.
"Thank you," he said.
"Is that better for you?"
"Yes, oh yes much better," overtaken by the exquisite delight that he admitted to himself he was now feeling.
Angie kissed him on the cheeks, the ears, his neck, and as her mouth moved towards her lips, he turned to her eagerly, their mouths locking as their tongues explored each other. Angie's control was excellent. No where near cumming, she was confident she'd discovered the optimal position for Michael, and in short, quick strokes drummed her cock repeatedly on his prostate.
"Angie - that's it - so good ... never ... no one's ... don't stop!"
Angie redoubled the speed of her fucking, rewarded by the moans and gasps coming from Michael. She experimented by putting a finger in his mouth, and he sucked it in greedily.
Angie stroked him into hardness, and then gave him a very professional handjob as she fucked him. Michael's hips began to buck as he felt orgasm approaching. Angie too felt herself beginning to lose control. She uncuffed his right hand, and then withdrawing from him, she quickly pulled the rubber from her cock. She brought her aching cock to Michael's lips. His mouth opened eagerly.
"Easy, Michael," said Angie gently. "Don't use your teeth, and don't try to take too much of me. Just do what you can comfortably manage." Michael could only take an inch or two without gagging, and once he learned the maximum depth, he began to move his head back and forth, possessed with a sexual excitement greater than anything he had hitherto experienced.
Feeling the moment approaching, Angie grabbed his head, and began to fuck Michael's mouth, Michael furiously pumping his own cock in time to the oral fucking. But Angie beat him to it, and Michael got only the briefest warning.
"I'm cumming!" shouted Angie. Michael made no effort to avoid the steady streams of sperm that fired from Angie's cock in his mouth. He swallowed greedily, but could not keep up with Angie's repeated and copious emissions, Angie's moans as her fierce orgasm continued serving as a spur to him to keep sucking and swallowing. Angie gathered her cum up with her fingers, and as her movements slowed and the sperm stopped flying from her cock, she inserted her fingers into Michael's mouth. He eagerly sucked and lapped, wanting to make sure he had all of what Angie had to offer. Coming down from her orgasm, she noted that Michael too had cum, his sperm launching itself in great jets on his chest and stomach.
Angie stepped back from the bed, and checking the camera, removed it from the tripod. Michael watched her in silence as she began to dress to go out. He knew better than to ask where she was going, and she stepped out of the apartment without a word.
With Angie gone, Michael easily could have escaped. After all, he had one hand free, and if he'd tried, he could have been free in a few minutes. But his put his free hand to better use, and by the time Angie returned well over an hour later, he'd masturbated himself three times to shockingly strong orgasms. He was working on a fourth when he heard Angie's key in the lock, and stopped his movements.
Angie stepped into the basement apartment, looking gorgeous. Michael noticed that she no longer had the camera. She unlocked Michael's other hand and undid the cuffs on his legs. He rose from the bed and got dressed only when she bade him do so.
"Take this," she said, dropping a key into his hand. "You'll notice that I etched off the locker number. The camera's in a locker somewhere around here, and you have the only key. But you don't know what locker it's in. You need me to tell you where to find it."
"What would you like me to do in exchange?" asked Michael.
"I'll give you the locker number when you prove to me that you really are sorry for that stupid letter you wrote to the school newspaper."
"Deal."
A week later Angie was pleased to see another letter from Michael to the school newspaper, retracting every syllable of his first letter, and asking for the forgiveness of everyone he'd offended. She had this in hand when she heard a knock at her apartment door - Michael, appearing at the time he'd appointed. He brought with him another copy of the newspaper, but after letting him in, Angie said she'd read the letter already, and was satisfied. She gave him the number and location of the locker, and a while later, Michael returned with her camera. She said he could watch her erase the file.
"Not until you've downloaded it," said Michael. "I'd love a copy. There's a couple of things I want to tell you, if you don't mind. First of all, I meant what I said in my letter. I really am sorry. I guess sexuality's a little more complicated that I thought."
"There's no need, Michael", said Angie. "I know you're sorry, and I hope you can mend things with the others."
"That brings me to my second thing I wanted to say," said Michael. "A bunch of us are going out tonight to a movie - want to come along?"
"I've love to," said Angie. "But on one condition. After the movie, when you come back to my place, you have to let me spank your ass while I fuck you. Now get on your knees."
Michael did as he was told.
"Mmmph - MPhmmmmm!"
"Don't try to talk with your mouth full," said Angie, pumping her hips back and forth and turning on the camcorder. "You'll find it easier to talk once you've swallowed my cum - but this time, you have to show it to me on your tongue first."
It was Friday night, and Michael sat in the student pub, alone. He should be out with his friends, having a good time. But he was all alone. The evening started normally enough. But things had quickly turned sour. Kimberly had clued him in right away that something was wrong.
"You asshole," she had said, not mincing words. "Did you write that fucking letter to the editor?"
"Look, it's not like you think, o.k.? I meant it as a joke."
"Here's my joke," said Kim, dumping an almost full pitcher of beer on him. His former friends all took this as their cue to leave. Michael was left alone trying to dry himself off with paper napkins.
He was surprised that the letter to the editor of the student newspaper had been so badly received. His subject was poorly chosen, given that he was in Toronto. Perhaps there were universities in the United States where an anti-gay, anti-transvestite diatribe might be received with mirth, but Toronto was rather different. The letter had been printed the day before, and he'd committed a blunder of the worst kind, and he could look forward to a rather solitary existence at U of T for some time.
But not all of his friends had deserted him - Angie, a medical student arrived at the pub just in time to see the drink dumped on Michael. Grabbing some paper towels, she came to help.
"She got you really good," said Angie, drying his hair. "What did you say to her?"
"It wasn't anything I said. It was what a wrote."
"That letter in the school newspaper?" said Angie.
"Yup," said Michael. "Some people just can't take a joke."
"You're just too soaked to dry off here," said Angie. "My apartment's only a couple of minutes from here. You're about my boyfriend's size, and he keeps some of his clothes at my place. I'll lend them to you." Michael expressed his gratitude, and followed Angie out of the pub, his ego deflated by his public humiliation.
"It's nice of you to bring me here like this," said Michael. "Aren't you afraid your neighbors will see you bringing a guy home who's not your boyfriend?"
"Not at all," Angie replied. "Even if I worried about that kind of thing, it's Friday night, and I'm sure no one's around." She handed him some clothes and a towel. and showed him the door to the bathroom. When Michael emerged a few minutes later dressed in borrowed clothes, Angie was sitting on her bed, with two mugs of hot chocolate. There was nothing suggestive about her sitting on the bed -the apartment was very small, and the bed doubled as a sofa.
"Don't leave until you hair is dry," she said, passing Michael one of the mugs. He sat next to her, gratefully accepting the drink. Angie had changed her clothes too, and now was in her pyjamas and a robe. She was a stunner, thought Michael, no doubt about that. Almost his height, with very long, wavy black hair, grey eyes and a perfect figure. They made small talk as they drank their drinks, Angie laughing at his jokes. At one point she leaned forward as she laughed, inadvertently displaying her cleavage. She sat up suddenly, and Michael was not quick enough at averting his gaze. Caught looking, he felt himself blushing.
To his relief, Angie laughed, and then kissed him.
"I have this thing where I have to be the one in charge," said Angie. "It's my body and my place, and you have to play by my rules."
"Deal," said Michael. He removed the jeans and underwear at Angie's bidding, and lay back on the bed, his eyes closed.
"Before we get started, we need the cuffs."
"The what?" said Michael, surprised.
"Yes, the cuffs. You do want to make love to me, don't you?
Michael quickly confirmed his wishes in this regard, and so allowed himself to be cuffed. Angie didn't cuff his hands together, but instead attached him to a short steel rod which hung from a cord fastened firmly to the top of the bed frame. He watched quietly as she cuffed his legs at the ankles, the cuffs joined by a length of chain. Had he been able to stand, he would have been able to walk, but running would be out of the question. Michael looked up at Angie, a smile on his face as she let her robe fall to the ground, and took off her pyjama top, treating her guest to his first view of her perfect 34B breasts.
"I think it's time for a blowjob," said Angie. "What do you think?" Michael was in full agreement. There was no doubt about it, in his view. He closed his eyes and lay back expectantly.
"That's great," said Angie, as she began to pull down her pants. "It is blow job time, so open your mouth."
Michael began to laugh, and opening his eyes, turned towards Angie.
"What the fuck? WHAT THE FUCK?" he shouted, for only a few inches from his face bobbed Angie's cock, easily the same length as his own, hard, turgid and demanding. His exclamations of horror became more frantic as he sensed Angie trying to shove something in his mouth - a ball gag. She put a knee on his chest, both to pin him down and inflict pain, and as he grunted in agony she fastened the straps on the back of his head. She stepped back to take in the view.
"It's really a bore having to put a ball gag on you," she said while she set up a camcorder on a tripod. "I'd much rather you be able to talk, and I think you'd rather be able to talk, too. It's not that I'm worried anyone will hear you - we're in the basement, and no one's around. It's just I find it distracting. Now can I trust you to keep your voice down?"
Apparently not. Moving forward, she grabbed his hair with her right hand, and firmly closed his nose with her left. Instantly Michael's air was cut off. She only let him experience this for a few seconds, and then relented.
"Let's try this again," said Angie. "Can I trust you to keep your voice down?"
This time the answer was a yes, for Michael had not enjoyed the feeling of being suffocated, even for an instant. He lay back meekly as his captor removed the ball gag.
"That's better. Now what about that blow job?"
"Please don't do this to me," said Michael, but in a whisper, desperate to keep the ball gag out of his mouth. "Please - I'm just not in to this."
"Then I'll let you go," Angie replied. "Once I've made sure I don't turn you on, that is. If you can stay soft, that will prove to me that you're not turned on, and that I should let you go." She stroked him, and Michael despaired as he felt himself immediately return to tumescence against his will, his cock aching and harder than it had ever been before. While this shocked Michael, Angie was not at all surprised, for the hot chocolate she'd given Michael contained a ground-up Cialis pill.
Angie moved back down the bed, giving Michael's cock a gentle tug as she did so.
"Mr. Happy's pretty hard, if you ask me," she said. "So you can cut the bullshit. Let me ask you - is it possible for a guy to have a rock-hard cock if he's not turned on?"
Michael's 'no' turned into a moan as Angie briefly took his full length into her mouth.
"You shouldn't have fibbed, Michael." He flipped over on to his stomach when she ordered him to.
The room was almost silent, the only sounds the gentle hum of a refrigerator, a car driving by, and then the plastic rustle of a package being opened, like someone opening a chocolate bar. After a short pause, the sound was repeated, and then Angie was lying between his legs.
"Some lubricant will make things a bit easier," she said. "I assume this is the first time you've been fucked."
"Please - not this - I beg you - I'll suck your cock I will please Angie don't fuck me please-"
"Shut up, Michael, unless you want to be gagged." Her middle finger, covered in a rubber and well-lubricated, snaked into Michael's ass.
"God you're so big Angie fuck that hurts, please stop-
"Michael, if you actually think that's my cock, I pity you. I'm just lubing you up with my finger."
"Nooo" said Michael, softly, silencing himself for fear of the gag. And then he felt Angie at his entrance, the head of her cock ever so much larger than the finger that had just penetrated him. He shoved his face into a pillow to stifle a scream as the invading cock violated him, pushing past the sphincter muscle, Angie's cock now buried in his ass.
"Oh god Angie that's so fucking huge I can't take it any more!" he whispered.
"Bad news, Michael - that's just the first inch. Here's the rest." And with this, Angie slowly but firmly worked the rest of her cock into Michael's tight and unwilling ass. In him now to the hilt, she began to fuck him with abandon: the quick, hard strokes of an experienced lover. Michael involuntarily let out a gasp with each repeated penetration, his insides feeling ripped open. The agony was incredible, and he could take no more.
"Please Angie Please stop oh please stop I'm sorry I'm really sorry!"
"What was that?" asked Angie, pausing on the down stroke.
"I said I'm sorry."
Angie pulled out of him, flipping him onto his back, his legs spreading like wings on either side of him as she once again positioned herself at his entrance. In this position, it was much less painful. Once the head of her cock was past his entrance, he felt very stuffed and uncomfortable, but not really in pain. He opened his eyes to see Angie's beautiful face above his.
"Thank you," he said.
"Is that better for you?"
"Yes, oh yes much better," overtaken by the exquisite delight that he admitted to himself he was now feeling.
Angie kissed him on the cheeks, the ears, his neck, and as her mouth moved towards her lips, he turned to her eagerly, their mouths locking as their tongues explored each other. Angie's control was excellent. No where near cumming, she was confident she'd discovered the optimal position for Michael, and in short, quick strokes drummed her cock repeatedly on his prostate.
"Angie - that's it - so good ... never ... no one's ... don't stop!"
Angie redoubled the speed of her fucking, rewarded by the moans and gasps coming from Michael. She experimented by putting a finger in his mouth, and he sucked it in greedily.
Angie stroked him into hardness, and then gave him a very professional handjob as she fucked him. Michael's hips began to buck as he felt orgasm approaching. Angie too felt herself beginning to lose control. She uncuffed his right hand, and then withdrawing from him, she quickly pulled the rubber from her cock. She brought her aching cock to Michael's lips. His mouth opened eagerly.
"Easy, Michael," said Angie gently. "Don't use your teeth, and don't try to take too much of me. Just do what you can comfortably manage." Michael could only take an inch or two without gagging, and once he learned the maximum depth, he began to move his head back and forth, possessed with a sexual excitement greater than anything he had hitherto experienced.
Feeling the moment approaching, Angie grabbed his head, and began to fuck Michael's mouth, Michael furiously pumping his own cock in time to the oral fucking. But Angie beat him to it, and Michael got only the briefest warning.
"I'm cumming!" shouted Angie. Michael made no effort to avoid the steady streams of sperm that fired from Angie's cock in his mouth. He swallowed greedily, but could not keep up with Angie's repeated and copious emissions, Angie's moans as her fierce orgasm continued serving as a spur to him to keep sucking and swallowing. Angie gathered her cum up with her fingers, and as her movements slowed and the sperm stopped flying from her cock, she inserted her fingers into Michael's mouth. He eagerly sucked and lapped, wanting to make sure he had all of what Angie had to offer. Coming down from her orgasm, she noted that Michael too had cum, his sperm launching itself in great jets on his chest and stomach.
Angie stepped back from the bed, and checking the camera, removed it from the tripod. Michael watched her in silence as she began to dress to go out. He knew better than to ask where she was going, and she stepped out of the apartment without a word.
With Angie gone, Michael easily could have escaped. After all, he had one hand free, and if he'd tried, he could have been free in a few minutes. But his put his free hand to better use, and by the time Angie returned well over an hour later, he'd masturbated himself three times to shockingly strong orgasms. He was working on a fourth when he heard Angie's key in the lock, and stopped his movements.
Angie stepped into the basement apartment, looking gorgeous. Michael noticed that she no longer had the camera. She unlocked Michael's other hand and undid the cuffs on his legs. He rose from the bed and got dressed only when she bade him do so.
"Take this," she said, dropping a key into his hand. "You'll notice that I etched off the locker number. The camera's in a locker somewhere around here, and you have the only key. But you don't know what locker it's in. You need me to tell you where to find it."
"What would you like me to do in exchange?" asked Michael.
"I'll give you the locker number when you prove to me that you really are sorry for that stupid letter you wrote to the school newspaper."
"Deal."
A week later Angie was pleased to see another letter from Michael to the school newspaper, retracting every syllable of his first letter, and asking for the forgiveness of everyone he'd offended. She had this in hand when she heard a knock at her apartment door - Michael, appearing at the time he'd appointed. He brought with him another copy of the newspaper, but after letting him in, Angie said she'd read the letter already, and was satisfied. She gave him the number and location of the locker, and a while later, Michael returned with her camera. She said he could watch her erase the file.
"Not until you've downloaded it," said Michael. "I'd love a copy. There's a couple of things I want to tell you, if you don't mind. First of all, I meant what I said in my letter. I really am sorry. I guess sexuality's a little more complicated that I thought."
"There's no need, Michael", said Angie. "I know you're sorry, and I hope you can mend things with the others."
"That brings me to my second thing I wanted to say," said Michael. "A bunch of us are going out tonight to a movie - want to come along?"
"I've love to," said Angie. "But on one condition. After the movie, when you come back to my place, you have to let me spank your ass while I fuck you. Now get on your knees."
Michael did as he was told.
"Mmmph - MPhmmmmm!"
"Don't try to talk with your mouth full," said Angie, pumping her hips back and forth and turning on the camcorder. "You'll find it easier to talk once you've swallowed my cum - but this time, you have to show it to me on your tongue first."
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