First of Many
Just trying out an alternate venue for my captions.
Alistair sat on the hotel room bed and took a small sip of the glass of red wine, he was feeling a little nervous, it had always been one thing to fantasise about what he was about to do but it was another thing entirely to actually go ahead and do it.
It had all started some months ago when the divorce with his wife of fifteen years had finally gone through, they had married young, almost straight out of school in fact and to begin with their relationship had been pretty stable, there were no children, not for want of trying and on the surface everything was happy and normal. Alistair loved his wife and she was more than enough for him, but that was until Alistair unable to control passions he had thought long buried and supressed any longer had started to dress in his wife’s clothes, at first he had managed to keep it secret and to only a few times a year, but slowly the urges got stronger and he dressed up more and more often, losing his job when the company he worked for went bust was a blessing and a curse, he was earning no money but he was left alone in the house during the day so he had more and more time available to spend as his feminine alter ego Ally fantasizing about a life lived as a woman. But what it really did was make his relationship with his wife even more fractious as she started to notice odd things going on with her wardrobe, items in the wrong place and toiletries and make up lasting less time than they used to, she began to suspect Alistair of doing exactly what he had been doing for years, wearing her clothes and using her make up.
Finally, she caught Alistair in the act by pretending to go out and returning secretly, confronting him Alistair burst into tears and confessed it all, to his dressing up in her clothes, using her make up and eventually to the fact that he fantasised about being with men. Upset and unable to understand him Alistair’s wife had left and a few weeks later she was filing for divorce, Alistair didn’t fight, even when it turned out he would lose pretty much everything, he just couldn’t bring himself to hurt the woman he felt he had wronged so much.
But that left him in a precarious position, still out of work he struggled to afford the rent on the simple bedsit apartment he now lived in, that he could indulge in dressing in the few female clothes and accessories he had retained whenever he pleased was scant consolation, he needed to make money and quickly.
The more Alistair thought about how to make money the more his mind kept coming back to some of the erotic stories he had read where men in a similar position to the one he found himself in turned to the oldest profession. He had masturbated to so many that he knew what to do backwards, hire a hotel room for the night, set yourself up on a website and wait for the clients to roll in, but fantasy was different from reality, wasn’t it, Alistair had fantasized about experiencing sex as Ally, but he wasn’t sure he could really sell his body for sex like in the stories, would he even be good enough.
Just thinking about being alone with a man who expected one thing only from him turned him on no end and he couldn’t stop himself from pulling down the front of his pants to reveal his straining cock wrapped in the delicate lace panties he was wearing that day, taking it in his hand he brought himself to an earth-shaking orgasm that filled his hand with cum. Looking at the warm liquid cupped in his hand he knew that what would be expected of any good whore, so tentatively he lowered his head close to his hand and dipped his tongue in.
It tasted salty and warm, but wasn’t unpleasant so Alistair lapped a glob up with his tongue, swilled it around his mouth, the strange saltiness filled his mouth and then with a quick gulp he swallowed, for some reason he felt a little buzz of excitement and his cock twitched, he returned his tongue to his hand and lapped up the remainder and swallowed that down, this time though he retched instinctively, he held his breath thinking he might throw up but the queasy feeling passed, then lifting his hand to his mouth he licked it as clean of his cum as possible.
For a few weeks Alistair teetered on the brink, always pulling back from committing to prostituting himself in that moment of guilt and clarity that comes post orgasm, on seeing his bank balance though he knew that he really had no choice, if he didn’t do it in less than a month, he would be homeless.
Taking the last of his money Alistair brought the best wig he could possibly afford, he brought some new makeup, a new pair of stockings and taking the one piece of sexy lingerie he had purloined from his wife he headed to a nearby hotel where he booked a room for the night.
After a long bath where he shaved himself from head-to-toe Alistair fixed his makeup and put on the wig and lingerie, satisfied he looked as passable as possible he took a few candid shots with his phone and then found a website catering for transgender and transvestite escorts and spent an hour setting himself up as Ally Waye. Alistair thought adding the pun Waye as a surname would make him stand out and it worked, within twenty minutes he had his first enquiry and after a short text conversation he had his first client on their way to his hotel room.
To calm his nerves Alistair poured himself a large glass of wine and sat on the bed, he watched his phone as messages began to appear, there were at least four more men who wanted his company tonight, the thought worried and excited Alistair more than he was willing to admit, he took another sip of wine and as liquid warmed his insides he tried to mentally prepare himself for what was about to happen. He had fantasized about this so many times and now it was going to happen, he was about to be paid to have sex with a stranger, to lose his virginity, Alistair shivered and took another sip of wine, his head buzzing he smiled and licked his lips, he looked over to the packet of condoms and lube on the bedside table ready to be used. Taking up his phone he arranged times for two more of the men to visit him and took another sip of wine, those three men would enable him to easily pay his rent this month, after them he would start to make a profit.
There was a loud knock on the door, Alistair got up off the bed, finished the last of his wine in one gulp and placed the empty glass next to the bottle, for a second he fussed at his slip making sure it was uncrumpled. There was another knock on the door, Alistair took a deep breath and walked over, ready to open the door on his first client of the night.
It had all started some months ago when the divorce with his wife of fifteen years had finally gone through, they had married young, almost straight out of school in fact and to begin with their relationship had been pretty stable, there were no children, not for want of trying and on the surface everything was happy and normal. Alistair loved his wife and she was more than enough for him, but that was until Alistair unable to control passions he had thought long buried and supressed any longer had started to dress in his wife’s clothes, at first he had managed to keep it secret and to only a few times a year, but slowly the urges got stronger and he dressed up more and more often, losing his job when the company he worked for went bust was a blessing and a curse, he was earning no money but he was left alone in the house during the day so he had more and more time available to spend as his feminine alter ego Ally fantasizing about a life lived as a woman. But what it really did was make his relationship with his wife even more fractious as she started to notice odd things going on with her wardrobe, items in the wrong place and toiletries and make up lasting less time than they used to, she began to suspect Alistair of doing exactly what he had been doing for years, wearing her clothes and using her make up.
Finally, she caught Alistair in the act by pretending to go out and returning secretly, confronting him Alistair burst into tears and confessed it all, to his dressing up in her clothes, using her make up and eventually to the fact that he fantasised about being with men. Upset and unable to understand him Alistair’s wife had left and a few weeks later she was filing for divorce, Alistair didn’t fight, even when it turned out he would lose pretty much everything, he just couldn’t bring himself to hurt the woman he felt he had wronged so much.
But that left him in a precarious position, still out of work he struggled to afford the rent on the simple bedsit apartment he now lived in, that he could indulge in dressing in the few female clothes and accessories he had retained whenever he pleased was scant consolation, he needed to make money and quickly.
The more Alistair thought about how to make money the more his mind kept coming back to some of the erotic stories he had read where men in a similar position to the one he found himself in turned to the oldest profession. He had masturbated to so many that he knew what to do backwards, hire a hotel room for the night, set yourself up on a website and wait for the clients to roll in, but fantasy was different from reality, wasn’t it, Alistair had fantasized about experiencing sex as Ally, but he wasn’t sure he could really sell his body for sex like in the stories, would he even be good enough.
Just thinking about being alone with a man who expected one thing only from him turned him on no end and he couldn’t stop himself from pulling down the front of his pants to reveal his straining cock wrapped in the delicate lace panties he was wearing that day, taking it in his hand he brought himself to an earth-shaking orgasm that filled his hand with cum. Looking at the warm liquid cupped in his hand he knew that what would be expected of any good whore, so tentatively he lowered his head close to his hand and dipped his tongue in.
It tasted salty and warm, but wasn’t unpleasant so Alistair lapped a glob up with his tongue, swilled it around his mouth, the strange saltiness filled his mouth and then with a quick gulp he swallowed, for some reason he felt a little buzz of excitement and his cock twitched, he returned his tongue to his hand and lapped up the remainder and swallowed that down, this time though he retched instinctively, he held his breath thinking he might throw up but the queasy feeling passed, then lifting his hand to his mouth he licked it as clean of his cum as possible.
For a few weeks Alistair teetered on the brink, always pulling back from committing to prostituting himself in that moment of guilt and clarity that comes post orgasm, on seeing his bank balance though he knew that he really had no choice, if he didn’t do it in less than a month, he would be homeless.
Taking the last of his money Alistair brought the best wig he could possibly afford, he brought some new makeup, a new pair of stockings and taking the one piece of sexy lingerie he had purloined from his wife he headed to a nearby hotel where he booked a room for the night.
After a long bath where he shaved himself from head-to-toe Alistair fixed his makeup and put on the wig and lingerie, satisfied he looked as passable as possible he took a few candid shots with his phone and then found a website catering for transgender and transvestite escorts and spent an hour setting himself up as Ally Waye. Alistair thought adding the pun Waye as a surname would make him stand out and it worked, within twenty minutes he had his first enquiry and after a short text conversation he had his first client on their way to his hotel room.
To calm his nerves Alistair poured himself a large glass of wine and sat on the bed, he watched his phone as messages began to appear, there were at least four more men who wanted his company tonight, the thought worried and excited Alistair more than he was willing to admit, he took another sip of wine and as liquid warmed his insides he tried to mentally prepare himself for what was about to happen. He had fantasized about this so many times and now it was going to happen, he was about to be paid to have sex with a stranger, to lose his virginity, Alistair shivered and took another sip of wine, his head buzzing he smiled and licked his lips, he looked over to the packet of condoms and lube on the bedside table ready to be used. Taking up his phone he arranged times for two more of the men to visit him and took another sip of wine, those three men would enable him to easily pay his rent this month, after them he would start to make a profit.
There was a loud knock on the door, Alistair got up off the bed, finished the last of his wine in one gulp and placed the empty glass next to the bottle, for a second he fussed at his slip making sure it was uncrumpled. There was another knock on the door, Alistair took a deep breath and walked over, ready to open the door on his first client of the night.
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