Very Mixed Doubles

Story Info
5 tennis friends decide to hold a Gender-Bender Party.
5.7k words
4.69
13.2k
7
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Very Mixed Doubles

Richard watched in admiration as his partner, Carey, gracefully picked the ball high out of the air on her backhand, and directed it out of reach, down the line for a clear winner. As he lined up to serve the next ball she crouched ahead of him, her skimpy tennis dress accentuating that delicious rear-end and long, toned legs.

Friday mixed-doubles was Richard's favourite afternoon. Two courts, four ladies and four guys were the ingredients for a very fun two hours. But even better was the flirtatious camaraderie of the five of them who had been playing together for several years. On the other side of the net were George and Penny; the former still single after a long marriage gradually disintegrated, and his partner seemingly more comfortable with her girlfriends than any occasional male who might try his luck. Carey, on his side, was temporarily single, her husband on a lengthy long-distance overseas posting. And, as for Richard, he was actively considering how to end a disastrous spell of inappropriate dates following his own long-dead marriage. Making up the numbers on the next court were a new-to-the-Club younger couple, temporarily filling in, a keen retired gentleman and the rather introverted but gorgeous Susanne. The latter had known the regular foursome for many years (and occupied Richard's lustful fantasies for all of them). Partners were alternated after every set so they all got pretty familiar with each other and the long-time five-some frequently stayed on for a drink when time allowed.

Today Richard and George exited the changing rooms to hear Carey, Susanne and Penny giggling at a corner table with a bottle of white wine already empty on the table between them. They hadn't bothered to change from their tennis gear, so long, bare legs were on careless display as Penny glanced over at the guys and said something that sent the other two into gales of laughter. She beckoned them over with a wink and nod of her head so they grabbed some chairs and moved to their table where a heady scent of female perspiration greeted them rather sensuously.

"For god's sake get a drink you guys and catch up" said Carey. "What the hell have you been up to in there all this time?"

"Well, if you must know" quipped Richard, "George was showing me the tennis skirt he's got for the next time you make him substitute as a girl. I'm beginning to think he's looking forward to putting on a bit of a show!"

"Jeeze, Rick, you didn't have to ruin the surprise" George played along, "Now they're all gonna want to see!

At this all three girls broke into gales of laughter, one wine glass was knocked over and both Penny and Carey collapsed into each others arms in total disarray. Richard and George exchanged puzzled glances wondering what they had done to cause this much reaction. Surely these two were not totally out of it after just a glass of house white.

Susanne tried to restore order, uncrossing her legs and leaning forward to make herself heard. "Listen guys, Penny has something to ask you". They both leaned in, more from the desire to sneak a better look at her wonderful cleavage than to listen more carefully.

"Ok, spill it Penney. Something's going on so don't be bashful, lets have it."

Penney looked at Carey and then Susanne, getting an enthusiastic YES from the former and a guarded nod from Susanne.

"Well it seems that we girls need a celebration. Carey has just heard that her hubby is not coming back and she has decided she's bloody fine with that."

"Wow, that's heavy, Carey. Are you sure you're OK?" George reached out for her hand but found that Penny had beaten him to it. Not only that but the two had turned to each other and exchanged a rather meaningful kiss -- on the lips."

Susanne added her hand to the two already clasped and looked over at Penney.

"So you see we have a great reason for a very fun party" announced Penney, "We were just talking about an appropriate theme and then you guys wandered over discussing the merits of cross-dressing!"

Richard tried to make sense of this. "So what am I missing. How does that fit in?"

"Well we had just decided.." she went on, still clutching Carey's hand, "that our party theme will be Gender-Bending!"

George and Richard exchanged puzzled glances.

"Well it seems...", explained Carey, "that I may have neglected half of the human race in my previous search for love and lust. On the other hand, maybe that's not for me. How do I know unless I live a little?"

"So guys, here's the deal" said Penney getting down to details. "If you want to join us and also live a little, you better be at my place by 8pm Saturday." Still holding Carey's hand she turned the other way to plant a kiss on Susanne's cheek. "And you better be prepared for the unexpected, with no rules and plenty of imagination. But, other than bringing plenty of booze, there is just one compulsory requirement."

She paused for effect realizing that she had their very full attention."At least one of the girls and one of the guys must be cross-dressed. Get it. We will make that promise, but if one of you doesn't come through, we'll party without either. Deal?"

Richard looked at George and his mouth fell open. But George stopped any comment by putting his hand squarely over Richard's and nodding enthusiastically. A cheer broke out from all three ladies.

"Deal" he said, and reached across the table to shake Penney's waiting hand.

"For Christ's sake, George, what the hell have you got us into, man?" Said Richard as the two finally made it out to the parking lot.

"Well, Rick, you could see they were pretty keen to have us along and hey, maybe it will be fun!"

"Yeah, I don't doubt that, but what I mean is which one of us will be stuck in women's clothing for the evening? It's sure as hell's not going to be me."

George stopped and put down his sports bag. "OK let's be fair. I'll spin a racquet -- UP you're the dick and I'm the dyke, - DOWN -- you get to try on the frilly frock!"

"No bloody way, man....." started Richard but it was too late as George sent the racquet into the air. Deftly he caught it and quickly looked at the logo on the butt.

"Shit" he said immediately, and started to put it away. "Looks like I've got trapped in drag and you've lucked out." He zipped up the bag and started walking towards his car. "But hey, here's the good news. Now you're the one picking me up and I'm the date - so bring plenty of wine and DON"T BE LATE!"

Richard was left standing by his BMW wondering what the hell just happened. George's Mustang growled past and he wondered why his friend didn't seem the least pissed off. And then belatedly realized that he never had seen which way up that racquet landed.

On the other side of the lot two of the three girls could not seem to stop giggling. Suzanne wasn't quite so amused. "So thanks a lot for roping in the guys to this crazy party, you two. You could at least have checked that out with me!"

"Oh lighten up, Suzie, it'll be a blast" shot back Penny, "This may well be an evening's education you will never forget"

"I somehow don't doubt that, Penny. But I didn't get the education you did at girls' boarding school and I'm not sure I'm ready for that kind of an evening now."

"It'll be fine Suzie" put in Carey. "Look, get yourself dressed up, come over a bit early and we'll make sure you have a couple of drinks inside you before the guys arrive. Then you can just sit in the corner and have a good laugh why we all make fools of ourselves."

"Well that's settled then. Jump in, Carey, we've got plenty of planning to do and not much time" said Penny as she opened up her Mini convertible for their joint ride home.

"We'll see you on Saturday, Suzie. Make it around 7.30 and go straight home now and get some early nights. You may not get much shut-eye this weekend!"

Their hoots of laughter almost drowned out the revving Mini as it took off leaving Suzanne alone to find her Subaru. Her thoughts churned scarily but a strange excitement was spreading south through her body.

* * * * * *

Richard parked in front of George's apartment block at 7.30 dressed in his best jeans, a dress shirt, leather coat and some decent black shoes. He'd wondered about a tie but figured the girls would only have a good laugh if he he overdid it. But he had brought a few bottles of decent wine and was pretty intrigued as to what he might be in for tonight.

As he searched for George's bell on the board outside he couldn't help but notice a rather attractive brunette sitting in the lobby reading a magazine. Long dark hair over one shoulder obscured her face, but the shapely legs crossed beneath a knee-length pleated, dusky-pink skirt gave Richard plenty to look at.

Getting no response from George's bell he tried again. Maybe he was on the way down.

Suddenly the lobby door opened and the gorgeous brunette stepped outside, her 4" scarlet pumps totally complimenting those spectacular legs which he could now see were sexily clad in diamond-patterned charcoal tights.

"Hi, Richard. I thought I said don't be late. You could at least have put on a decent suit for a special night out!" The husky voice was all too familiar.

"Holy shit George, is that you? Where the hell did you come up with that outfit. You are totally hot!"

"It's Georgina tonight Rick, and don't forget it. Now let's get going and make sure you open the car door for me." Rick started to say something but couldn't quite think what. He felt Georgina take his arm as they walked to the car, those flashing red heels clicking sensuously beside him.

* * * * * *

Suzanne had arrived early as instructed but was not particularly happy with events so far. As usual she had dressed with great care. Tonight she wore a tight, black leather skirt with a prominent, hem-to-waist brass zipper, sensuously open to half thigh. Underneath peeked a short, black lace slip which matched the bra peeking enticingly from her maroon, silk blouse. This in turn was matched exactly by strappy, 5" maroon stilettos. She sat alone with her second white wine on a bar stool by a love-seat, fuming at the other girls as they kidded around and joked at either end of a long couch the other side of the room.

"I thought you said you were dressing up, Penney," Carey was saying, "I was expecting some sort of James Bond-with-a-tux look!" Penney was wearing dark, very tight-fitting men's pants over black cowboy boots. Her masculine, white, long-sleeved shirt was set off by a narrow black tie and a multi-coloured gilet, giving the outfit a distinctly mischievous look. A jaunty, grey fedora capped off the butch-look perfectly.

"Well hello, Carey, who's talking," shot back Penney. "I already know you've got great legs but if that skirt was any shorter I'd be looking at your navel instead of that hot little sex-shop, red thong you're flashing at me." In truth it seemed that Carey had relied on her skimpiest tennis skirt for effect while adding most decidedly not-tennis, spiked heels and a sequined, pink sweater. The latter was so tight that her red lace, push-up bra was straining to be seen and the overall effect would not have been out of place after midnight at the wrong end of main street.

"OK so I might have pushed the envelope a bit but we are here for some fun and, in truth I'm wondering why we asked the others because from over here I'm beginning to find you rather irresistible"

Penney raise her eyebrows sensuously and reached over to place one hand on Carey's bare thigh, "I'll bet you say that to all the boys, Carey - but what shall we do about the lovely Suzanne?"

At that moment the doorbell rang and a voice announced the new arrivals over the intercom.

"Well, welcome boys......." Penny's voice stopped abruptly as she opened the door to see Richard with a stunning brunette on his arm.

"Hi Penney, I'm Georgina. So pleased to meet you" she said extending a feminine hand. "Richard has told me so many great things about you two".

"Come on both of you and get a drink. I certainly need another and you're several behind already." Penney recovered her composure and offered a spot on the couch and a bar stool for the pair. "Hey Suzanne; say hello and don't be such a stranger over there".

Georgina's head turned towards Suzanne and their eyes locked for some seconds. Something intangible passed between them and Suzanne's cool composure was visibly dented. "Oh...hi.." was all she could muster.

Georgina said nothing but dropped her camel coat on the bar-stool and made her way over to Susanne where the two became straightaway engaged in an intimate conversation

Three pairs of eyes had taken full note of this development and there was plenty of eye-rolling in wonderment.

"Well I guess we'll stop worrying about Susanne now," said Penney. "Carey, you sit in the middle. George, get a drink and sit down right here; we three have a few things to figure out."

Richard didn't need any more invitation but reached into the nearby cooler for a beer while Carey moved over to make room, displaying her legs to the max while her breasts struggled heroically for independence. Richard's eyes were already popping out when he noticed that Penney's tight trousers displayed an alarming and lengthy bulge nestled at the crotch. He hadn't a clue what was going on here but knew he wouldn't miss it for the world.

* * * * * *

"Hi Susanne, I'm Georgina" she breathed coyly. Please tell me where you got that gorgeous skirt. It suits you sooo beautifully and I am totally jealous".

"Oh, Georgina, you are quite exquisite. I've been trying to find a pleated skirt with a top like yours for ages. Do sit down and help me with this wine while we find out all about each other and trade secrets." "Oh yes, that sounds like a great plan. Do you mind telling me where you shop for those lovely things?"

"Well I have a few special places where I find my size easily. But really, I might ask you the same?"

Georgina hesitated, "The thing is Suzanne, I've never been out dressed like this before. To be honest I get everything online and only dress up on special occasions at home. I'm kind of wishing I had the nerve to go shopping as a girl".

"Georgina, you are so obviously feminine you simply must get out more. I would love to take you shopping and we could give each other fashion tips. Don't you think that would be fun?"

Georgina's heart skipped a beat. Could this really be happening? Could she really go out as a girl and have Susanne as a close friend?

"I would absolutely love that! Maybe you could help me a bit with make-up choices and fill me in on all the real girl-talk stuff." For a moment she thought she had gone too far but then Suzanne reached over and, for a second, they clasped hands in an unspoken bond.

Their eyes locked. "Georgina, I'm starting to think you might be that one special person I've never managed to find. You see I've had boyfriends and I've even tried girlfriends but for some reason nothing clicks. The men are too boring and crude and the girls too flighty and... well just not sexy enough, if you know what I mean." She reached over and poured Georgina some more wine. "If you don't mind telling, just how have you managed your two life-styles? Do you think you really want to cross right over?"

"Its just so confusing, Suzanne. I love being a girl but its hard to pull it off for more than an evening at home alone. If you could really be my friend it would be incredible to go out together as girl-friends."

"Of course we will Georgina," she reached across to stroke the pleated skirt. "We can dress to kill and flirt outrageously with any men we want" She stopped for a moment her fingers stroking the soft pleats. "But is that what you want too? Do you dress to feel sexy and do you watch the men's eyes as they lust after you?"

"I never have but, oh god yes, that sounds fantastic? Do you think I could ever pull that off, Suzanne?"

"Absolutely, Georgina. I think the two of us together could do anything we wanted. We could seduce anyone we wanted. But now I've said that I wonder whether it actually is a man or a woman that you really want?"

Georgina took a deep breath. Well here's the thing. Half of me does want to attract men. I'm not sure but I might even want to try something with a man. But deep down I really think I will never stop craving the touch of a woman. Does that make any sense?" She wondered if she had said too much. "What about you?" Susanne sipped her wine and also wondered where she should let this conversation roam. But she knew that this might one of those rare moments when things just fell into place.

"Georgina, I think this sounds perfect. We can be girls together whenever we please. But, at the end of the day, you just might occasionally end up by being the man of my dreams -whenever that pleases us both, of course."

There was a long pause as they looked at each other. And then both leaned in for a soft but passionate kiss.

* * * * * *

Richard gulped down his beer trying desperately to think of something sensible to say. Beside him his tennis buddy Carey had turned into a jaw-dropping tart. Then, looking past her amazing cleavage all he saw was some sort of androgynous she-man eyeing both her friends with amusement and lust equally. Penney then pulled a heavy black eye-mask from her vest pocket and addressed them both.

"It seems my friend Carey is having a little sexuality confusion, Richard. While part of her is doing just fine encouraging that blatant erection of yours the rest apparently wants to see what I'm hiding in my britches. I'm thinking we might need a little to help to figure this crazy lady out".

Embarrassed, Richard crossed his legs trying to hide the obvious truth but that merely made it worse as Carey now turned to stare, knees slightly apart to flash that triangle of scarlet right in his gaze.

"OK, Carey, knock it off and put this on right now." Penney slipped the mask over her friend's eyes and tightened it up so that not a glimmer of vision would show through. "Now sit still and just trust your senses. We will offer you two versions of everything and I want you just to say 'ONE' or 'TWO' depending which you find the most turn-on. Now, no reaching out to figure out who is who. Just let me keep score on this little notepad.

She turned up the music to better cover up any whispers between them, pulled out her pad and showed Richard the plan. The list ran from a soft kiss on the neck to gentle stroking of shoulders, then breasts followed by more daring caresses of the legs and upper thigh and finishing with a deep and passionate kiss on the lips. They would alternate as first and second and she dusted a short spray of her perfume on Richards neck to confuse things. He was now on his third beer and totally blown away by the outrageous but well thought-out and plan.

And so it started as Carey swayed her head, crossing and uncrossing her legs, shivering with anticipation as the game began. True to the rules she kept her hands to herself and called out One or Two as demanded, her breathing quickening and her face becoming quite flushed as delightful caresses moved tantalizingly around her breasts.

"Oh, My GOD" she shrieked as Penney's fingers drifted below her waist and then moved up her inner thigh just grazing her panties. But Richard wasn't to be beaten as he gently parted her legs further and slid one finger slowly up the other leg until he too was caressing that dampening scarlet thong and Carey's breath came in ragged pants.. This drew a sharp look from Penney who drew his hand away before moving in for her final sensual kiss. After about 20 seconds it was Richard's turn to ease her aside for as passionate and juicy a smooch as he could manage.

12