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. “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 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 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.”
“You look great too,” he replied.
“Oh, it’s nothing special,” she said. “But it gets me in here.”
“It’s my first time,” admitted Andrew. “I came with my friends.”
“I thought I saw you with Em and Calum. It’s cool that you’re here.”
“Thanks. It’s a bit different, but I’m kind of enjoying it.”
She smiled again. “I’m Robyn, by the way. Outside, that’s Robyn with a “y”, though in here I should spell it with an “i” really, if I ever needed to write it down.”
“I’m Andy, it’s nice to meet you.” He held out his hand, and she shook it in an exaggeratedly masculine way, with a firm grip and a cheeky smile. “I guess that’s Andi with an “i” too,” he added.
“Well, Andi-with-an-i, why don’t you drop those drinks over with Calum and Em, then come back here and tell me about yourself?”
Andrew felt a shiver of excitement. He had a feeling he’d just been “picked up”.
He took the drinks back to the table where Calum and Emily were chatting.
“I’ll be back in in a sec,” he said, “but I just got talking to this girl at the bar…”
Emily looked across. “You got lucky for a new boy,” she smiled. “Robyn’s lovely; you’ll have fun with her.” She waved, and Robyn waved back, then gesticulated for Andrew to come back.
So, back at the bar, Andrew explained about how he knew Calum and Emily (omitting certain details about his voyeurism, and most of the sex), and how they’d invited him to Jo-Jo’s. In turn, Robyn explained about her “excruciatingly dull” day job, and how discovering about the club (through a friend who was a member) had taught her all sorts of exciting things about herself and what turned her on sexually.
“And one of the things that really turns me on is seeing hot guys in cute dresses,” she murmured. She put her hand on Andrew’s leg and squeezed it. Then, instead of taking her hand away, she boldly slipped it under the hem of his dress and stroked his bare thigh.
“Mmm, Andi, you have such firm thighs,” purred Robyn, “and so smooth.” She leant over and began to lick his neck, while pushing her hand further up. Andrew felt his skin tingle as her fingers reached his panties and rested on the bulge of his genitals.
“Oh, Andi, what’s this? You’re a naughty girl, you didn’t tell me about this. Most girls don’t have one of these. And it’s weird; it seems to be getting bigger.”
Andy could indeed feel his cock swelling under the effect of Robyn’s stroking fingers. At first it was constrained by the material of the panties, but then she pulled at the elastic and his erection sprang free. Her hand immediately gripped it and gave it a squeeze, making it swell even more.
“Oh goodness, it’s escaped,” she giggled. “That’s very naughty. I wonder if I should have a look?”
With her other hand, she pulled the hem of Andrew’s dress right up. Looking down, he could see the tip of his erect penis cradled in her hand. As she fondled it, a little squirt of pre-cum shot out.
Robyn giggled. “Oh goodness, it just spat at me. That’s so dirty, Andi, I’ve got mess on my hand now.” She let go of his cock and licked the translucent liquid off her wrist.
She looked at Andrew. “Would you like to come upstairs? There are a couple of rooms people use, and I’d like to have a closer look at your spitty thing.”
Andy nodded, his heart starting to beat faster. He’d only just got here, and already he was getting off with a dirty, sexy woman. “Yeah, that’d be cool,” he said, his voice croaking with nervous excitement.
She led him towards the back of the bar. As they passed Emily and Calum, Emily gave them a thumbs-up sign.
“Be careful with her, Rob,” she said. Calum just sniggered.
Once they had reached the first floor, Robyn tried the first door they came to. It was locked, however, and Andrew could hear sounds of sexual activity inside. But the next was open, and she dragged him in. It was furnished like a standard hotel-type bedroom, but Andrew didn’t have time to look at it too carefully before Robyn had pushed him against the wall and begun to kiss him. His cock was still rearing up out of the top of his knickers, and Robyn rubbed herself against it. She put her hand up his dress and began to drag his knickers down. Then she pushed him down onto the bed and pulled the front of his dress right up.
“Let’s get these off you,” she purred, pulling Andrew’s black knickers down his legs and tossing them onto the floor. Then she pulled his thighs roughly apart and knelt between them. His cock twitched in anticipation as she took hold of the base, then bent down and took the smooth shiny head in her mouth.
Robyn was an enthusiastic cock-sucker. She sucked in her cheeks and rolled his knob-head around in her mouth, before easing the full length of his shaft into her mouth until the tip was bumping against the back of her throat. Then she carefully adjusted the angle of her head and Andrew felt the end of his penis slide down her throat. She looked up at him with a twinkle in her eye, and slurped at the base of his shaft.
“Oh Jesus fuck,” moaned Andrew. She was better than good, she was a master – or should that be mistress?
Robyn cradled his smooth ball-sack in her hand, and slid his penis in and out of her mouth, coating it in her saliva. Then she sat up and removed her tie, before starting to undo her shirt.
As she undid the last button and let the front gape open, Andrew realised that one reason she looked so boyish was that her breasts were almost non-existent, just two small swellings on her chest. But her nipples were dark, with prominent areolae, and currently sticking out like the proverbial chapel hat-pegs. Andrew reached up and ran his hands over them, while Robyn began to undo her trousers.
“Oh Andi, that’s nice,” she breathed as his fingers tweaked her little nipples. “I so want to fuck you.”
“God, yes, Robin, I want you too,” said Andrew. Her androgynous figure and masculine attire had got him very aroused and his cock was rock hard. He reached round to unzip his dress, but Robyn stopped him before he had got very far.
“No, babe, keep it on,” she said. “I want you to wear your dress while I fuck you.”
Quickly, she dragged off her shoes and socks, before pulling down her trousers and briefs. Then she straddled him, and he saw that her sex was totally hairless, though he was intrigued to see that she had a silver bar-style piercing through the folds of her outer labia. Her lips were glistening with juices. She was clearly as much turned on as he was.
She leant over and kissed him, while he played with her little nipples. She was frotting her pussy against his leg, leaving smears of juice.
“Lick my cunt first, Andi,” purred Robyn, relishing the harsh crude obscenity. “Then we can fuck.”
He didn’t need to be asked twice, and rolled her over onto her back. Her pale naked body was coated in a thin sheen of sweat, and Andrew gently licked the moisture from her flat stomach, tasting its saltiness on his tongue. Then he licked up over where her breasts would have been if she had had any, and flicked his tongue across her dark nipples, feeling the areolae dimpling with arousal as he sucked the hard little buds one at a time. Gently he nipped at them with his teeth, making her moan under her breath and push her flat chest up against him. He could hear her heart beating, fast and excited, and smell her exotic musky aroma.
He kissed back down her firm flat tummy, momentarily letting his tongue flick round the neat little cavity of her navel, before pressing at last into the soft smooth tissue of her plump pubic mound.
As he reached his goal, Robyn sighed and parted her legs in welcome, offering him her vulva. With his fingers, he carefully spread apart the tight folds of her outer labia, exposing the pink wet flesh. She clenched her vaginal muscles, forcing out a little trickle of juices. Andrew breathed in the sweet, delicate scent, before licking at the delicious secretions. Carefully and tenderly, he sucked the delicate folds of her labia into his mouth. Robyn’s breathing was heavy and audible, and he could hear little high-pitched squeaks in her throat. He focused on the labial piercing, flicking it with his tongue, and Robyn squealed with delight.
Easing his tongue into her vagina, he licked round inside, pressing against the soft spongy walls. His mouth was pressed right into her spread-open vulva and her juices smeared themselves across his face.
He had deliberately left her clitoris until last. As he licked up her slit and around the tight little hood, he teasingly avoided the bud itself. Then he gave in, and flicked his tongue back and forth against the firm little nub of flesh.
Robyn let out a stream of profanity. “Oh fucking cunting shitting hell!” she exploded. “Yes, yes, fucking yes, that’s it. Cunting Jesus!”
She rocked her hips up, her hands grasping the sheets so hard her knuckles were white. Andrew put his mouth over her clit and encircled it with his lips, while building up a rhythm with his tongue. The little bud was rock hard with arousal. His own cock was rock-hard too, pressed against Robyn’s leg.
Robyn’s ragged breathing suggested her orgasm was not far off. He continued to flick his tongue across her clit, and slid two fingers into her wet passage. Teasing her, he scissored them inside her, pressing the tips into the spongy walls of her cunt, then began to pump them in and out of her. He may not have had much actual sex, but the hours spent on the internet meant that he had a pretty good idea what women liked. It certainly worked with Robyn. With each squelch of his fingers her cunt seemed to get even wetter, and her juices squirted out onto the bed.
Andrew curled his fingers up inside her cunt, pressing them against her G-spot. At the same time he sped up his clit-licking. Robyn was thrashing about on the bed, and with a huge cry of pleasure she orgasmed. It must have been audible to anyone within about 100 yards of the room.
Andrew withdrew his digits as Robyn lay panting on the bed. A thin string of her juices hung between her cunt and his fingers as he raised them to his mouth and licked them clean. But Robyn was still horny.
“I’m going to fuck you now,” she panted, “I’m going to stick your thick cock in me.”
She reached up, grabbed his arms and pulled him down on top of her, pressing her mouth to his and kissed him as if she was trying to suck out his soul. Then she rolled him over onto his back and straddled him, taking his erect penis in her hand. Andrew didn’t think he’d ever been as hard, even when spying on Emily through her window.
“Oh honey, you’re so big and hard,” she purred. She pulled down his foreskin and pressed his round firm head against her clitoris, rubbing it against the firm little bud. Then she let it slide between her labia and lowered herself onto it. Andrew signed as he felt his penis enveloped by the warm wet sheaf of her tight vagina.
Robyn clenched her vaginal muscles around his shaft, then began to ride him up and down. Her tiny breasts jiggled up and down delightfully. Andrew reached up and tweaked her nipples, and she growled deep in her throat.
“Pinch them, Andi, hard, hard,” she gasped. Andrew pressed them as hard as he could between his fingers. It must have hurt, but Robyn just begged him to squeeze harder.
He was doing his best to hold himself back, but he realised that his cock was going to erupt pretty soon.
“I’m gonna come, Robin,” he managed to gasp. She smiled, and raised herself up, letting his sticky cock slip out.
“I want to see you come,” she said, grabbing hold of his erection and beginning to pump her hand up and down the well-lubricated shaft.
“That’s such a pretty dress, Andi, it would be such a shame to get a load of spunk all over it,” she said. “But I think it’s going to happen anyway.”
She aimed his cock at his own chest, and rubbed him until he ejaculated. As loop after loop of his semen spurted out of the end, she made sure as much as possible of it was spread all over the front of his dress. Several long ropes of stuff splattered over the front, some of it even hitting his neck and dripping off his chin. Thick dollops clung to the material, starting to soak in at the edges.
“Oh Andi, you look like such a dirty girl,” said, Robyn, sitting back and admiring her handiwork. “Let’s go back to the bar and show Em and Calum.”
Andrew stood up and smoothed down his semen-coated dress, taking care not to get too much of the goo on his hands. Showing off the results of their fun was clearly all part of the deal. He adjusted his bra and artificial boobs, which had got a bit twisted out of position by the vigour of their fucking.
As soon as Robyn had finished getting dressed, they left the room and went downstairs. Another couple (both men in dresses) were waiting in the corridor, and they slipped quickly into the just-vacated room. Andrew felt a momentary urge to stay and listen at the door, but he also wanted Emily and Calum to see his messy dress.
“I’m sorry, mate,” he said to Calum, as he and Robyn sat down at the table, “We seem to have got a bit of mess on your dress.”
“No problemo, compadre,” said Calum. “The more mess, the more fun. And it’s had worse.”
Emily leant over and scooped up with her finger a thickly tenacious globule of semen that hadn’t yet soaked into the dress. She put the finger in her mouth and made an appreciative noise.
“You do have the tastiest cum,” she said.
Andrew wondered if he’d be producing any more before the evening was over.
