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Andy opened the large carrier bag that Tom had dropped off earlier, and dropped the contents onto his bed. He hadn’t realised how excited he would be to wear the clothes that he had been given. In the bag were pink panties, pink suspender belt, pink stockings, pick bra, along with a black party dress and handbag. They all looked about the right size for Andy. Until now he had never thought about dressing like this, never dreamt of it, but this looked so exciting. And felt so exciting. Of course he had played with his sister’s panties a few times, and with his mother’s. But here was a complete sexy outfit for him to wear, out, in town. He was nervous, almost to the point of pulling out, but the excitement was keeping him going. He began to remove his clothes to get changed. This evening he was going to be Andrea, not Andy……………
It had all started a couple of weeks before.
Tom and his best friend Luke worked in the local sports centre. They had been friends of a long time, and people liked them. Both were over six foot, sporty, good looking lads in their mid twenties. Tom had fair hair, Luke black hair. Both muscular. Both played rugby for a local club. They were general workers at the sports centre — cleaning, manning the reception, sometimes helping in the weights room. They were popular, friendly guys. Both of them had at different times had girlfriends, and there were always girls willing to be with them. Quite a few had been members of the sports centre, and on the odd occasion they had done a threesome together with some kinky hot woman — generally a married member of the centre who was getting bored with her husband.
Also at the centre was one of the personal trainers — Bill. Bill was a bit older, always with new ideas, always trying to make an extra penny with some sort of scheme or plan. And he had told Tom and Luke about his latest madcap scheme — trannyoke! He had seen it mentioned on the internet, and fancied a go at running it. The idea — hire a bar midweek, have a tranny as host, and do Kareoke! And of course, try to get as many trannies along as possible. Bill wasn’t stupid — he knew several people in the trans community, and thought it was a group he could tap into to make some extra money.
Bill had talked Luke and Tom into coming along for his opening evening. Wednesday evenings were quiet, so Luke and Tom didn’t need much convincing. It’d be a good laugh, and if they had a couple of drinks they could sing as badly as the rest of them! Bill sold them the tickets, but then broke the bombshell. “You have to bring a tranny with you.” He said it jokingly, and they knew it wasn’t essential, but again they thought it would be a good laugh if they could find someone.
Luke and Tom talked about it, and thought about who they could get to dress up for the evening. Brothers were out. Other people at work were out. Friends at the rugby club were out. They needed someone they could ask who wouldn’t go and tell everyone if they didn’t want to do it.
Then Tom had the suggestion: Andy. His cousin. Luke had met Andy, and knew they had their man. Andy was 19, slim, and had grown his black hair long. He was a student, studying art history. He was friendly, quiet. Maybe he would…….
Tom had asked him, and after a bit of encouragement agreed — as long as it was just a bit of a laugh. He idolised Tom, and had liked Luke when he had met him. Tom had promised to find the right clothes for Andy, and had scrounged from family members, sisters, friends and got an outfit ready for Andy to wear. He had also got his sister Susie to agree to do some make-up for him as well.
There had just been istanbul travesti one odd incident that had set Tom and Luke thinking. They had been looking on the internet for the sort of thing a tranny might wear. They had ended up on a porn site, where two guys were having sex with a tranny, who looked very feminine in clothes and make-up. On the surface they had laughed at it, but Tom had jerked off later imagining it was him and Luke having sex with the tranny. Luke had also found the video a turn on, and had even given a hint when he said to Tom jokingly: “we’ll have to give that a go one day…….,” the comment seeming to pass quickly.
The day came, the evening after work for Tom and Luke, after college for Andy. Tom and Luke felt excited, but not as excited as Andy.
So Andy removed his clothes and began to dress himself. He put on the pink lacy panties — they were a bit of a stretch over his cock, but he felt comfortable when they were on properly. It took a few minutes to get the stockings and suspender straps right. He wasn’t sure whether they should inside or outside the panties. He settled for inside. He put on the bra — it was tight, but it was okay. He put on the dress, found the zip difficult but managed to do it up. He had insisted on flat shoes — and they had found a pair of black slip on female sandals. He looked at himself in a mirror and thought he didn’t look much like a woman.
Susie came, and did his make-up. Bright red lipstick. Eye-liner. Other powders and creams he didn’t understand. He looked in the mirror and there was someone who could be a woman looking out at him. Susie had been very encouraging that he looked amazing. She left — he still had half an hour before Tom and Luke were going to collect him.
It was about nine when Luke and Tom had turned up. When they saw Andy — Andrea as he now called himself, and told Tom and Luke to call him — Tom smiled, Luke wolf-whistled. Neither has come across a tranny before, and here was a really hot shemale in front of them. Of at least — Andy dressed as a woman, and looking very sexy.
When they arrived at the pub there were already several people there, including a number of men gorgeously dressed. Andrea thought he looked as good as any. He — no, she was really nervous, walking into a public space dressed so sexily. The three headed towards a table with a corner bench. They got Andrea to sit in the corner on the bench and Luke sat next to her. Tom got some drinks in, then Bill came over with a couple of friends and sat at the table as well. It was when one of them looked at Andrea, smiled, and said “mmmm, you’re a sexy little minx,” that Andrea felt worst, or best. She went bright red, and demurely turned to the side. It was then that Tom returned with the drinks and sat the other side of Andrea from Luke.
Bill’s friend — Andrea quickly learnt he was called Tony – turned to Tom and spoke. “You didn’t tell me you knew such a hot little cow as this one here.”
Tom laughed. “Leave her alone. It’s her first night doing this.”
“First night? We’d all want to spend the first night with her!”
Tom laughed again. “Leave her alone. She only came with us so we could get in. It’s was Bill’s instructions.”
“Okay,” said the friend, Tony, then turned and smiled directly at Andrea. “But if you want to go the whole way and more, and none of these blokes want to, then come back to my place at the end of the night.” He smiled, then the conversation became more general, discussing what they might sing that evening. Andrea was quiet. She had never had anyone speak to her like that, ever, before. It was embarrassing. istanbul travestileri But exciting. But, what was going to happen…….
Bill started the show. It was a great laugh. People got up and sang, most of them really badly. Everyone sang along when they could. Tom and Luke kept Andrea in drinks.
Towards the end of the evening Bill said they were going to have a pause -to get last drinks in. To decide who was the best, and get them up to do the finale.
Bills two friends, Tom and Luke and Andrea sat chatting, poking fun at each other. It was then that Andrea felt it.
There was a hand on her knee, caressing gently.
Perhaps it was the drink, but maybe deep down it was what she wanted, but she did nothing to stop it. It was Luke — it was under the table, but it was Luke’s side. The hand slowly moving up her leg, moving under her skirt. To the top of the stockings. Andrea never knew why she let her legs open, but her body was buzzing as the hand caressed the inside of her leg above the top of her panties. For Andrea it was amazing. The fingers caressed for three of four minutes as the conversation went on around Andrea. And then the hand moved again.
It was cupping Andrea’s cock. Over her panties. It was squeezing her cock, tickling her cock, caressing her cock. Gently squeezing her balls. Andrea was sitting back breathing heavily. It was so good. So exciting. She didn’t realise that her face was glazed, her breathing heavy.
“You playing with her cock?” The voice broke in — Bill’s friend Tony from earlier. He looked at Andrea. “Is he playing with your cock?”
Andrea felt the hand release him. “Not any more.” somehow it was the honest reply.
At that moment Bill took to the microphone to announce the winner, who started singing Frank Sinatra’s “My Way” and everyone joined in. As Andrea put her arms in the air to sing along she felt the hand on her knee again, moving up her thigh and grasping her cock again through the panties. She was immediately hard again, but the hand was very skillful — exciting Andrea, but never letting her cum, releasing her as she felt the cum rising in her balls.
It was closing time, “My Way” had finished. It was Tony who said: “I only live ten minutes walk away. Who’s coming with me and Andrea for drinks?”
Only Luke seemed interested. Andrea felt rushed into it, but didn’t mind. Andrea felt strange walking between the two men, each holding her hands, one on each side. Truth was — for Andrea it was so exciting to be walking, dressed as a woman, through the streets, even if it was nearly midnight and dark. Maybe it was the drinks she had at the pub that made her lose her inhibitions. Or the buzz in her body after the treatment from Luke in the pub.
As they walked, Andrea looked a little closer at Tony and squeezed his hand. He was probably late thirties, confident, a couple of inches taller than Andrea. He wasn’t heavily tone, but with his short fair hair he looked kind of hot, for a man. She wondered what would happen at Bill’s friend’s……
It happened very quickly! They were through the door, and while still in the hall Tony had grabbed Andrea and kissed her on the lips, hard, then thrust his tongue into Andrea’s mouth. Luke responded almost as quickly, standing closed behind Andrea, raising her skirt, letting his hands rest on Andrea’s ass, over her panties, then under her panties, pushing fingers into the crack of her ass.
Andrea responded instinctively — this felt so exciting. Her tongue moved to meet Tony’s tongue, and wrestle with it. At the same she let her legs spread wider, allowing Luke easier travesti istanbul access to her asshole. As Andrea kissed, so she felt her asshole caressed, then pushed into, a finger just getting through the ring.
Andrea felt Tony’s cock pushing through his trousers against her, both rock hard. Tony broke the kiss and whispered to Luke “We’ve gotta fuck her, now.”
They pushed Andrea along the corridor and into the bedroom. Tony said — “I wanna fuck her mouth. You want her ass?”
Luke smiled — there was nothing more he wanted, than to fuck Andrea’s ass, Andrea’s mancunt.
Tony stripped as quickly as possible, sat on the bed, pulling Andrea on with him. He lay back, and pulled Andrea onto all fours, her mouth by his cock, her ass in the air. He pulled her mouth to his cock, and pushed his cock to her lips. Andrea didn’t need any encouragement — she opened her mouth letting Tony slip inside. It was big, but not too big. She had never sucked a cock before but this was the most amazing experience she had had. She trapped his cock with her lips, and began slowly to caress it with her tongue.
Andrea felt the hands grasp her hips. She felt her skirt pushed up to her waist. She felt her panties pulled down over her stockinged legs, and to the floor. She stopped sucking for a moment as she felt the bed move — Luke kneeling on it. Then she felt it pressing against her asshole. It was clear Luke had found some gel somewhere, because the cock slipped through the ring, stretching Andrea almost to the point of real pain. Luke pushed hard until his cock was buried full length in Andrea’s asshole.
Andrea felt so taken. So full. So exposed. This was too much. She was invaded, totally. Andrea felt totally out of control as Tony pushed up with his cock, beginning to fuck Andrea’s warm, wet, welcoming mouth. Out of control as Luke reached around Andrea to grab her cock and begin to slide in and out of this tight, warm, gripping hole.
Somehow Tony and Luke managed to get into a rhythm. Tony had his hands on Andrea’s head, holding as his cock thrust in and out, as Andrea tasted his pre-cum. At the same Luke grasped Andrea’s cock using it to help pull his own cock in and out of Andrea’s ass. Andrea suddenly had a moment’s panic — he knew neither were going to release him when they were shooting their cum, and he worried about the taste, and swallowing…..but it was still too exciting to even think of stopping.
Suddenly Luke cried out, moaning loudly as the cum shot out of his balls, up his cock, deep into Andrea’s guts. He thrust and pumped over and over…………….. It was too much for Tony: suddenly he thrust up and started shooting his cum into Andrea’s throat. Andrea tasted it, swallowed, struggled to swallow all of it as Tony shot load after to load.
Andrea thought they would never stop, but at last they did, both coming down from the best fuck they had ever had — with the hottest slut they had ever met — so they thought at that moment.
Both allowed their cocks to shrink out of Andrea, then slumped on the bed, breathing heavily, gasping, Andrea still on all fours.
After a few minutes it was Luke who rolled Andrea onto her back, grasped her cock and began to wank him off. It took moments until Andrea was shooting cum all up the front of her dress, leaving great white drops of gue all over it. For Andrea, this was amazing, as these two men watched him cum as one of them jerked him off.
It seemed strange after that. Luke walked back to the pub to collect his car, then drove Andrea home. The bad thing about trannyoke was that it had to be midweek, and they had to work the next day. Andrea was soon Andrew again, and fast asleep in his own bed. Piled on the floor in the corner was stocking, suspenders, bra and dress. The next morning back at Tony’s house, he was wanking himself off with a pair of panties that had been worn by the hottest sexiest fuck he had ever known…
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