Andrew learns how to be a transvestite prostitute
Andrew stood in front of the mirror, his reflection showed a leggy woman wearing a short tight shift dress with black suspender belt, stockings and 6" stiletto's. He felt like a total slut and was very aware of the silky lacy pantie and bra set he was wearing under his dress. He had spent ages on his makeup and was pleased with the attractive woman he had created. Lately he had felt it wasnt enough to just feel and look like a woman, he had always liked looking at naked men and now he found he wanted one to use him as a female. He dreamed of men roughly pulling his smooth stocking clad legs apart and pushing their hard swollen cocks deep in his anus.
Well tonite it was finally going to happen. He had put some pics of himself dressed in a minidress on a website and a man had contacted him asking if he wanted fucked. The guy wanted to fuck him without a condom and spunk inside him. Andrew wasn't sure but when the guy said he would pay £200 for Andrew to dress like a tart and give him a full girlfriend experience including unprotected sex, he couldn't resist and agreed to sell himself to the man.
So now Andrew stood waiting at the front door dressed as an attractive woman,when the door went he started trembling uncontrollably but he opened it with a timid smile at the big man outside, she felt his eyes roving over her body her legs especially.
"So what's your name slut?," he said. "Andrea, sir," she simpered as she sank to her knees and started unbuckling his belt. She tugged down his trousers and gasped inwardly at the bulge in his boxers. His cock was very thick and at least 7 inches, it was circumcised and his bellend was an angry purple colour, it slapped her cheek a few times and felt very stiff, she opened her mouth and felt it fill her whole face as she sucked hungrily on his rigid cock.
She held the hard cock tight in her right hand as she worked her lips over it, looking up she saw he was watching her pleasure him with her mouth with a small smile on his face. He pulled her up and kissed her full on the mouth as he fondled her buttocks. Now she led him to her bedroom and where he pushed her sprawling on the bed, her dress rode up and revealed stocking tops and the smooth hairless milky white skin of her thighs.
"Put your legs over my shoulders sweetheart and I'll be able to fuck you deep," he said. Andrea lay back as she felt the hot head of his hard cock rubbing against his anal lips, she grunted with pain as he pushed his cock slippery with lube half way up her arse. "Ooohhh...it hurts," she squealed, "it's too big. I can't take it." He eased his cock out of her then thrust hard into her and now she had three quarters of his throbbing manhood stretching her hole as she screamed in pain. "Stop, please stop," she whimpered as he slid out of her again, this time he leant into her with his whole weight and she knew he was balls deep inside her, his cock filling her insides as he started thrusting harder, forcing his hardness deep within her gaping arse.
It seemed to go on forever before he arched his back and came with a flood of spunk into her wet hole. Andrew lay back sobbing as his lover withdrew his softening cock from his reddened arse, a trickle of cum came out with it and ran down her thigh. "That was good Andrea, you make a good woman. Well done," the guy said.
"I think I should pimp you to some men I know," he said with a grin. "I'm not doing this again," Andrew gasped as the man laughed. "Of course you will. You're a cock slut now and besides, once the video of me barebacking you is uploaded, you will be getting lots of customers." "From now on, I will find you cock and you will do as your customers want. I will dress you and instruct you how to please men...is that understood?" Andrea just lay there knowing that he was a transvestite prostitute now and would be used for sex many times.
Well tonite it was finally going to happen. He had put some pics of himself dressed in a minidress on a website and a man had contacted him asking if he wanted fucked. The guy wanted to fuck him without a condom and spunk inside him. Andrew wasn't sure but when the guy said he would pay £200 for Andrew to dress like a tart and give him a full girlfriend experience including unprotected sex, he couldn't resist and agreed to sell himself to the man.
So now Andrew stood waiting at the front door dressed as an attractive woman,when the door went he started trembling uncontrollably but he opened it with a timid smile at the big man outside, she felt his eyes roving over her body her legs especially.
"So what's your name slut?," he said. "Andrea, sir," she simpered as she sank to her knees and started unbuckling his belt. She tugged down his trousers and gasped inwardly at the bulge in his boxers. His cock was very thick and at least 7 inches, it was circumcised and his bellend was an angry purple colour, it slapped her cheek a few times and felt very stiff, she opened her mouth and felt it fill her whole face as she sucked hungrily on his rigid cock.
She held the hard cock tight in her right hand as she worked her lips over it, looking up she saw he was watching her pleasure him with her mouth with a small smile on his face. He pulled her up and kissed her full on the mouth as he fondled her buttocks. Now she led him to her bedroom and where he pushed her sprawling on the bed, her dress rode up and revealed stocking tops and the smooth hairless milky white skin of her thighs.
"Put your legs over my shoulders sweetheart and I'll be able to fuck you deep," he said. Andrea lay back as she felt the hot head of his hard cock rubbing against his anal lips, she grunted with pain as he pushed his cock slippery with lube half way up her arse. "Ooohhh...it hurts," she squealed, "it's too big. I can't take it." He eased his cock out of her then thrust hard into her and now she had three quarters of his throbbing manhood stretching her hole as she screamed in pain. "Stop, please stop," she whimpered as he slid out of her again, this time he leant into her with his whole weight and she knew he was balls deep inside her, his cock filling her insides as he started thrusting harder, forcing his hardness deep within her gaping arse.
It seemed to go on forever before he arched his back and came with a flood of spunk into her wet hole. Andrew lay back sobbing as his lover withdrew his softening cock from his reddened arse, a trickle of cum came out with it and ran down her thigh. "That was good Andrea, you make a good woman. Well done," the guy said.
"I think I should pimp you to some men I know," he said with a grin. "I'm not doing this again," Andrew gasped as the man laughed. "Of course you will. You're a cock slut now and besides, once the video of me barebacking you is uploaded, you will be getting lots of customers." "From now on, I will find you cock and you will do as your customers want. I will dress you and instruct you how to please men...is that understood?" Andrea just lay there knowing that he was a transvestite prostitute now and would be used for sex many times.
8 years ago