His First Time In A Dress

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The next morning, Andrew woke up to find a text from Emily on his phone.“Come over at 11,” it read.  “Gr8 idea 4 2nite.”That sounded intriguing, he thought. He showered, made himself some breakfast, then ambled over to Cavendish Hall. When he got to Emily’s room, Calum was already there, sitting with his feet on the table and nursing a cup of coffee.“Hey, Andy,” he said with a wave. “Last night, eh? Wow. My arse is still sore from the banging you gave it.”“That’s cool,” said Andrew, trying to sound as if this was a normal topic of conversation among his circle of friends. “I enjoyed it too. It was fun.”Emily smiled. “His arse should be used to it by now, the number of cocks it’s had up there. Not to mention all the other stuff,” she observed, handing Andrew a coffee.“Yeah, yeah, that gerbil was fully consensual,” said Calum with a grin.“Ignore him,” said Emily. “He’s winding you up. He’s always like this when he’s had a good fuck the night before.”Then she sat down on the bed, indicating that Andrew should do the same.“Calum’s had a great plan,” she announced. “Tonight we’re all going to go to Jo-Jo’s. Have you heard of it?”Andrew thought hard. The name rang a bell, but he wasn’t sure why.“Isn’t it some sort of club?” he hazarded. “Up by the station?”“Some sort of club, yes,” agreed Calum. “But Saturdays you can’t just turn up. There’s a dress code.”That seemed fair enough to Andrew. Lots of the Nottingham clubs had dress codes, especially at weekends. No football shirts, no DMs, that sort of thing.“That’s fine, just tell me what not to wear,” he offered.“It’s more a case of what you do wear,” said Emily enigmatically. “And you might not have everything handy. But don’t worry, Calum can lend you some stuff. Can’t you, fam?”“Mi casa es su casa,” said Calum, with a terrible Spanish accent. “We might as well have a look now, in case something doesn’t fit and we need to go shopping this afternoon.”They went next door, and Calum opened his wardrobe.“Now,” he said, rustling about and pulling out something on a hanger, “this might do for starters.”He held it out for inspection. Andrew looked at it. At first he thought it was a long fancy shirt. But of course it wasn’t. It was a frock, with a bright flowery pattern, all reds and greens and yellows.He gave a wry smile, as Calum and Emily looked at him, trying not to laugh.“Okay,” he said at last. “I think I get it. This is a dress, right, and we’re going to some sort of kinky club?”“Well, sort of,” agreed Calum. “But it’s a bit more than that. You have to try the dress on, then we’ll explain. Actually, maybe try this one as well,” and he pulled out another, this time in a fetching shade of pastel blue.Andrew stripped to his boxers. The flowery dress was quite low-cut at the front, and was fastened by a zipper down the back. He stepped into it and pulled it up, sliding his arms through the sleeves. Emily smirked as he struggled to do up the zip.“You could always give me a hand instead of standing there sniggering,” he grumbled, and Emily smartly took the zip from him and pulled it up in one smooth movement.Andrew looked at himself in the wardrobe door mirror. bahis siteleri “It’s a bit loose at the front,” he commented.“That’s because you’ve got no boobs, sweetie,” said Emily scathingly. “We’ll sort that out next. But you’d better explain to him about Jo-Jo’s, Calum. It’s your place really.”“You’re right about Jo-Jo’s being a sort of club,” said Calum. “They used to have different themed musical nights at the weekend; heavy metal, country, sixties, you know the sort of thing. But then one month they decided to have a sort of cross-dressing night, when men had to come as women and vice versa. It was mostly just aimed at students, as a sort of a laugh, like a “vicars and tarts” party. But it really took off, and they started doing it every month on the first Saturday. And then all sorts of actual trans people started going there, not just students in fancy dress, and it became a real meeting place for them. Of course, some people started using the toilets to have sex, and there were a couple of incidents with unsuspecting “normal” customers getting a bit upset. Then the police started asking questions, so they made it a “Members Only” club for Trans Night. Non-Members can get in as a guest, but only if they’re accompanied by two existing Members. And they can only do that once; after that, they have to sign up as a full Member if they want to come back. Emily and me are Members, so you’re okay this time.”Andrew nodded. He had a feeling he’d heard some gossip about Jo-Jo’s before, but hadn’t really considered going there, even if he could have got in.In the meantime, Emily had been searching through one of the drawers. She produced a rather pretty yellow bra.“Obviously, if I was wearing this dress I wouldn’t normally bother with a bra,” she said, “but the whole point of you wearing it, is that you need to compensate for your lack of boobage. So we use these pads in here, to fill the cups out a bit, and you put the bra on.”She took a couple of small soft padded cushions out of the drawer, and fitted them into the bra cups. Andrew pulled down the dress, slipped the bra over his arms, while Emily did it up at the back. He adjusted the pads until they fitted snugly, then with Emily’s help zipped up the dress again. He adjusted his boobs, and looked at himself in the mirror, not quite sure what to think.Emily smiled. “You look so cute,” she giggled. “Calum has some more interesting clothes that he likes to wear, but this little dress looks right for a first-timer. It helps if people know where you fit in. You can try the blue one if you like, but to be honest I think this is perfect.”Andrew was relieved to hear this. He felt happy being identified as a beginner at the cross-dressing game.“You might like to try these too,” suggested Calum. He handed over a pair of lacy black briefs. “They look about your size.”Andrew pulled down his boxers, and replaced them with the briefs. They were pretty skimpy, and had a see-through mesh at the front through which his penis was clearly visible, curled up at the moment but ready to swell up.“Mmm,” said Calum appreciatively. “Those look pretty good. I’d fuck canlı bahis siteleri you.”“You’d fuck a hoover if it had frilly undies on,” commented Emily rudely.Andrew had expected to feel a bit uncomfortable standing there in his dress, but he was rather enjoying it.  “Do I need stockings or tights?” he asked.“Tights are a pain to get off,” said Emily, “And I’m not sure stockings go with that frock. You’re trying to look virginal, not sophisticated. So let’s stick with bare legs. Though you definitely need to shave them, unless you’re going for the total lesbo dyke look.”“Jesus, Em, you can’t say that,” chastised Calum. “That’s so wrong, and you know it. Even so, she’s right, hairy legs don’t go with that frock at all.”“No problem, I’ll go back and shave them before we go out,” agreed Andrew.“Two more things,” said Emily. “Shoes – what size are you?”“10.”“That’s a bit of luck, so’m I,” said Calum. “Let’s stick with the innocent virgin theme, and give you a pair of flats.” He found a pair of simple black pumps, and Andrew slipped them on.“And finally, the pièce de résistance, some hair,” said Emily triumphantly. She opened one of several boxes and took out a blonde shoulder-length wig. She slipped it over Andrew’s own hair, and adjusted it with an expert eye.The wig certainly put the finishing touch to the ensemble. Andrew had to admit that as cross-dressers go, he was very definitely still a bloke in a dress, but he guessed that that was probably the right look for a complete beginner. It would have to be a very dark pub for anyone to be fooled for more than a second or two.“So do you think I’ll fit in okay like this?” he asked.“No problem,” said Calum. “You already look better than some of the guys you get in there, though of course there are others who take it all much more seriously. You wouldn’t look twice if you passed them in the street in broad daylight, unless you fancied them of course.”“Right,” said Emily, “That’s sorted then. Leave the clothes here, go back and get to work on those legs with the razor this afternoon, and be back here by eight. Then we’ll doll you up properly again, and hit Jo-Jos.”—“Cheers, mate,” said Calum with a wave, and the taxi drove off into the night. Andrew looked up at the entrance to Jo-Jos. To be honest, it looked pretty seedy, with its pink, flickering neon sign, blacked-out windows, and slightly menacing bouncer on the door. Now that he was actually here, standing outside in his frock, he felt a bit nervous.On the other hand, compared to Calum he looked pretty inconspicuous. His new friend must have been wearing a whole cow-and-a-half of leather, from tight bustier to thigh-length boots, with whip to match.  Andrew wondered who would be on the other end of the whip that evening; somehow he didn’t think it was just for show.“Okay, babe?” said Emily. She was looking smartly butch in a black dinner suit with frilly shirt and plain bow-tie. As she’d admitted, there wasn’t so much choice for women who wanted to dress like a man. Because so much casual clothing was unisex, you were pretty much forced to go for the suit-and-tie combination. “I did try canlı bahis a cowboy outfit once,” she’d confessed, “but I just looked like a member of a bad Village People tribute act.”“Come on then, guys,” said Calum. He went over to the doorman and greeted him like an old friend.“Evening, Norman,” he said. “Here we are again. This is Andy, he’s our guest tonight.”“Good to see you, Cal,” said Norman, high-fiving Calum. “There’s a good crowd in tonight, plenty of your mates, and some new skins too. You’ll have fun, I reckon. You too, Andy, have a good time, and don’t let Cal get you into trouble.”He held the door open, and they went in.Andrew hadn’t been quite sure what to expect Jo-Jo’s to be like inside, but at first glance it all seemed remarkably like any old pub on a Saturday night. There were groups of people sitting round tables, talking and laughing, while others clustered round the bar buying drinks. It was only when you looked closely that you realised that the ones in dresses and skirts were men, and the ones in suits were women. Some of the “women” were almost comically non-feminine, even having beards and moustaches; others were totally convincing in their alternative identities, to the extent that Andrew wouldn’t have realised they were cross-dressing if he’d met them in the street.  But they were all clearly having a good time, and he began to feel a lot more relaxed.“Right, first things first,” said Calum, “Drinks. Shall we have a whip?” And he slammed his leather lash onto the table.Emily sighed deeply. “I swear to God he only brings it so he can make that joke every time,” she said, putting down a twenty.“You’re just jealous of my natural wit and charisma,” said Calum, throwing a note onto the table as well. “You want to get them in, Andy? Mine’s a Peroni.”“And I’ll have a white wine; large,” said Emily.  “Just the house; it’s pretty good, surprisingly.”One thing Andrew did notice as he waited his turn at the bar was that there was quite a lot of kissing and heavy petting going on, and some of it went rather further than you’d see in your local Wetherspoons, even at closing time in Leeds. He saw one woman with her shirt unbuttoned having her breasts felt by a man in a purple frock, and there was clearly a blow-job being given under a table in the corner by the toilets. So people clearly came to Jo-Jo’s with the intention of getting down and dirty, and Andrew wondered just how far it was acceptable to go. Surely actual intercourse didn’t take place in the bar area?  Suddenly it was his turn, and he ordered two Peronis and a large house white. When he was waiting for the beer to pour, he felt someone ease themselves into the space next to him. He looked round, and saw an attractive girl with short black hair, wearing a man’s two-piece suit with a plain white shirt and a tie loosely knotted around the neck. Even without the context of this being a cross-dressing establishment, she was clearly a female, and a very attractive one. The masculine attire seemed to enhance rather than mask her feminine allure. She looked a much better man than he did a woman, but he’d worked out by now that that didn’t matter a great deal.Andrew smiled.“Hi,” he said.She smiled back, a cute knowing grin.“Hi, that’s a nice dress,” she said, taking hold of the edge of his sleeve and rubbing it between her fingers. “It suits you.”

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