Jessie

They looked at each other and laughed.

"Let's make it even more interesting," Devon suggested. "How about a little wager. I bet Jessie's a guy."

"And I bet it's a gal. Otherwise I've been hugging and kissing a guy all the time. Though that'd be interesting, too. Kissing a guy wearing a dress."

"Jessie is a good kisser, isn't he?" Devon smiled.

"You bet. He or she, a good kisser."

"So what're we betting for?"

He pondered for a moment. "Something appropriate... let's see... how about, loser performs oral sex on winner."

"Sounds like a deal. I hope your tongue works as well on my pussy as when you're kissing."

"You may never find out!" Taylor said confidently. "Let's go dance, and check out the others. We've got to see and be seen for the beauty contest."

The party was in full swing. People were dancing, others were sitting at the bar drinking and chatting. As was customary on the dance floor partners were swapped out regularly, so it was not long before Devon and Taylor lost sight of one another. Neither cared, it was exactly what these evenings were about.

Jessie fully participated as well, in both the drinking and the dancing parts.

I always participate in my parties. Of course I do, it's fun. Tonight I decided to go as man. So I dressed up in a nice suit, which is looking really good on me if I say so myself.

The dance floor is a great place to meet other people, and get up close and personal with them. Tonight's relaxed soul music includes many slow shuffles, allowing everyone to snuggle up and rub their bodies together. I participate in this as well. I love the physical touch, the touch of all those people. It makes me feel warm.

Always I try to give equal attention to both the men and the women. But it never works out quite like that. If dressed like a man, I always get more attention from the women, and the other way around. I dance with and kiss both genders, they're equal to me. I love the gentle soft kiss of a woman, the passionate rough kiss of a man. I love the gentle soft arms of a woman, and the strong demanding arms of a man.

After a few songs both Devon and Taylor had a dance with Jessie, taking their time to feel Jessie up as well as they could.

"So what do you think, male or female?" he asked her when they met again at the bar.

"He danced rather close with me," she told. "No chance to get a hand between us, at least not accidentally. I felt his butt. It's nice and round."

"Very feminine isn't it?"

"Could be. But not much of a waist. I still think it's a guy."

"Skinny girls don't have much of a waist, so I stand with my assessment that Jessie is indeed a female."

"We need a better grope," Devon concluded. "We can't tell just yet."

"Try again later. Now let's fill in our voting papers. Who do you think is the best of show tonight?"

It is time to collect the votes. I walk around the banquet as people make up their minds and write down their votes. I wonder who they will vote for tonight, and pass the notes to the bartender who will help me tally them.

It's game time. I always have some games in mind for people to loosen up, to get to know one another, to get together. Tonight I'm asking the couples to find their partner. Everyone is blind folded. Then the males, by assumed gender, so actually the girls, line up, and the females have to try to find their own partner.

The catch: no hands above shoulder level. Faces are easy to recognise, so no touching there. Only touching the rest of the body. Kissing is allowed, as everyone kisses differently they should be able to distinguish their partner that way even as their body shapes are so hidden.

And when they think they have their own partner, or rather when they find someone they like they can leave the line up together. This is how new couples are formed.

We're going to do this four times, switching roles each time. This just has to be fun.

"Got your eye on someone already?" Jaime asked.

"Sure. See that tux there? She's got lovely eyes," Taylor replied.

"So you're not going after me, huh?"

"Oh, was I supposed to?" he teased.

"Of course! Who knows who I end up with. It could be a guy in a dress!"

"It could indeed very well be. You got your eyes on anyone?"

"Well... look, that pink cocktail dress, doesn't he look hot?"

"Sure, but those boobs are fake."

"So are yours."

"Of course. Time to put on our blindfolds, game's on."

The next fifteen minutes were all about groping and kissing. It is not easy to find your partner when blindfolded, where many other people walk around, and where she's dressed in a way to obscure her normal curves. As Jessie said, kissing was the most reliable way of identifying one's own partner, as everyone's kiss feels different. That is, if any of the participants was out to find their real life partner.

One by one couples left the playground and settled down at the bar, still blindfolded. Only when everyone had been coupled, the blindfolds were removed and laughter ensued. Everyone was curious who they ended up with, and with whom their partner ended up with. They were given another fifteen minutes to socialise, after which it was time for the next round.

Jaime quickly walked towards the guy in pink cocktail dress she fancied.

"Hi, I'd like to have a date with you," she said to him.

He looked at her, his eyes roamed her body. "Sounds fine with me. I'm Lindsey, what's your name?"

"Jaime."

"Nice name. How are you going to find me?"

"That's why I'm here, to get to know you a little better," she said, and stepped closer to him. She pressed her body against his, roaming her hands over his body, and kissing him deeply. Their embrace lasted for a minute after which she broke away. "You kiss really well, that's promising. And it should help me to recognise you."

"You make me wonder what more you can do with that mouth," he answered.

"Maybe you get to find out later! At least I like what I'm feeling down there."

He moaned a little. "You know what you want, don't you?"

"Sure I do. I just hope you want me, too."

Isn't it lovely if people try to make such dates? This is what I do it for. Have people have fun together, break away gender and other boundaries, have them make new connections, if only for a single night.

I put on a blindfold myself, let's be fair, and join the girls in their quest to find a guy. After all I'm also dressed up like a man tonight. I'm not going to form a couple with anyone of course, but I'm also not going to stay at the sidelines all the time. This is way too much fun. Kissing, feeling up some bodies, being felt up, no way I'm going to pass on that.

Jaime managed to find her agreed date within a few minutes. It was about the seventh person she found, felt up, and kissed. Finally she felt the correct kiss, the kiss she received just before the game, and also the body was the correct size and shape. Confidently she took the man to the bar, continuing to kiss him, rubbing her body against him.

"Don't remove your blindfold," she whispered. "It's better like that. You got to know me blindfolded to be able to find me next time."

"Agreed. But maybe you should remove your hand from under my dress. If you continue like that, I'm going to shoot."

"And maybe you should have worn underwear."

"This is more fun isn't it? Now stop it, will you?"

"Maybe I shouldn't, making you cum now will help you last longer later."

In the meantime, Devon had also made her choice, and took her date to the bar.

"Devon, it's you, right?" he said.

"Sure."

"Why pick me? Not interested in fooling around with another guy?"

"Well, I was wondering if I could actually recognise you. Jessie challenged us to find our real partner, and that's what I did. Even though I'm sure most people won't. We still have two more rounds to go, no worries about the fooling around part."

Charley laughed. "You're quite something. So was it easy to find me?"

"Well, reasonably easy. I was more and more worried you'd been taken already as I had to kiss and feel up like ten guys in dresses before I finally had the correct one."

"I also immediately recognised you when you touched me."

The third round started, and again the women had to stand and wait. It was not for long until Jaime felt a man's hands on her body, and soon felt some fake boobs pressed against hers, and lips locking with hers. They kissed for a minute, before he left again, soon to be replaced by another guy.

This continued for a while. Five, six, seven men touched and kissed her, but not her intended date. She got impatient and nervous, would he be able to find her? The eighth man kissed her deep and hard, a pretty nice kiss, but still not the man she was after. Then he took her arm, and to her shock took her out. She missed her date.

He took her straight to a sofa, one of the few that had been lined up strategically along the walls. "Have a seat," he invited her, and they sat close down together, their legs intertwined.

"You feel nice. From the moment I found you I felt like we have a connection," he said softly.

"You kiss well," she admitted.

"Thanks. I'm Jamie, how about you?"

She giggled. "Jaime. What a coincidence."

"I knew we had some kind of connection!"

"It seems so. Oh, we can remove our blindfolds now."

They removed their blindfolds, and Jaime had a good look of her date. "You look really sexy," she said. "Nice boobs you made. And good that you shaved those legs, otherwise that miniskirt would really look terrible. Feels good too, nice and smooth."

"Thanks. That dress is my girlfriend's, she thought it'd suit me."

"It does suit you. And your make up is done very nicely. You know if I were a lesbian I may instantly fall for you."

"And now you're not a lesbian, and I'm not a woman?"

"I know you're not a woman, I felt that already. Mmm, what's this, no-one wearing underwear under their dresses?"

"Why?"

"You're the second guy without underwear I meet tonight. They should make dresses into regular men's wear. Very nice."

"You look like you like what you feel."

"And you look like you like me touching you. You like the thought of a guy playing with you?"

"I know you're not a guy. You're a girl in a suit. Your chest gives you away. Would love to see them when they're free."

"I could hook you up with hubby. You two may make a nice couple."

"Thanks for the offer but I think I prefer you, lovely lady."

They kissed again, Jaime climbing on top of him, her hand still in his dress.

The fourth round starts soon. I see people making out all over the place, they are really enjoying themselves. There are indeed some really well looking cross dressers out there, I am really curious who are going to be voted winners.

The girls are making good use of the easy access provided by the dresses. I really wonder how many guys will end up messing up their partner's dresses. And how they're going to explain that to the dry-cleaner's when the dress comes up for cleaning.

When the fourth round started Jaime did not take any risks. As quickly as possible she was going from partner to partner, trying to beat any competition. She got lucky, the fourth man she kissed felt like Lindsey. The total package felt like him. Wasting no time she grabbed his arm and took him towards the bar. A sneak peek from under her blindfold confirmed not only that she had the correct guy, but also where to find the sofa that proved so comfortable when she was making out with Jamie.

"Glad you found me so quickly," Lindsey said.

"Of course. You failed last round."

"No luck. I tried and tried, got one girl that felt very much like you, spent some extra time with her then realised it's the wrong one. In the meantime someone must have taken you out. In the end there were three left, I just took one of them."

"How was she?"

"Nice. We had a fun chat, kissing and cuddling a bit."

"Your leg is sticky. That cuddling was not 'a bit'."

"You put me on a hair trigger."

"Your long search for me didn't let the tension drop?"

"You mean with all those girls kissing and fondling me? That's not helpful in that matter."

"It explains why there was no hard pole pressing my belly this time. I was already wondering why."

"Yeah, sorry about that."

"Don't worry, you'll last longer for me tonight."

"I definitely will. Looking forward to see that chest of yours without restraints. Even with it's quite obvious."

They started kissing again, feeling one another, until Jessie started to announce the results of the evening's beauty contest.

"The results of the election are in. The results were pretty close, everybody got their fair share of votes. You all did a really great job with your reversals, please give yourself a big hand!"

Everyone applauded.

"Now it is time to put some beautiful people in the spotlights. The two of you that got just a few more votes than the others. The differences were small, but in the end the winners are Sammie and Alex. Where are you guys? Please come forward."

This is my favourite part of the night. See how well they did. And did they do great!

Sammie is wearing a stylish, ankle long evening gown. His hair flowing down his shoulders and some subtle make up completes the picture of a beautiful woman. He also walks really elegantly, even though he's on pretty high heels. I think he's wearing a corset as he has a waist. I give him a warm hug as he walks up the stage.

Next is Alex, wearing an impeccable tuxedo. She could have dropped into any black tie party, no problem. She could have taken Sammie as her partner, and the two of them would easily get away with it. Alex her hairstyle is very well done, her chest and shoulders have been moulded to make for a strong, masculine look.

"Congratulations you two, you really did an excellent job. For each of you the coveted Medal of Honour, please cherish it."

Everyone applauded, and the band started to play again.

This is always the moment the evening really begins. This crowd is great. The game went great, they all have been nicely warmed up. I'm sure soon we'll see the first couples move off to the privacy of a hotel room.

I am also going for a dance. There are so many delicious bodies to rub against, so many beautiful mouths to kiss.

I'm not going to a room with any of them. That would break the Jessie mystique. Don't worry about me, I get my share of sex. Some of my close friends do know what's under those clothes.

With the music playing, some people went on the dance floor, others were sitting at the bar having drinks, chatting. Jaime was out on the dance floor with Lindsey, making out.

Devon looked around, looking for Taylor. She still had this bet open, and was wondering if Taylor had made any progress sexing Jessie. She spotted him at the bar, chatting with another beautiful woman, who of course is actually a man. She recognised him, it was Morgan.

"Hi Taylor, Morgan. How're you guys tonight?"

"Pretty good," Taylor answered. "How about you? Had some good dates?"

"Very good. I love men in dresses, especially if they're not wearing underwear."

"I take it you took full advantage of that," Morgan said.

"Oh yes, I did. My hand is still a little sticky."

"No surprise there, knowing you," Taylor said. "By the way, any luck with Jessie?"

"You trying to date her or so?" Morgan asked, looking surprised.

"Oh, you also think it's a girl? How come you think that?"

"Jessie is a girl's name, and she looks girlish, even in a suit."

"Jessie is just as much a boy's name. Jessie looks more like a guy to me. But Charley also thinks he's a girl. We hope to find out tonight."

"How?"

"A dance and a grope. We put a little wager on it, loser to - oh, there she is. I'm going for it. See you later."

Devon jumped up and darted towards the dance floor, asking Jessie for a dance. It was a nice slow song, giving them an opportunity to get up close and personal.

"What's going on here? What wager?" Morgan asked.

"Oh, she's going to try to figure out whether Jessie is a boy or a girl. I said girl, she said boy. Loser will give oral to the winner."

"Sounds like a bet you can't lose."

On the dance floor Devon was having a slow dance with Jessie, praising Jessie for the good organisation and the great time she had there.

She bent her head in for a kiss, eagerly answered by Jessie. Then, moving a little away to get access, she quickly moved her hand and placed it right in Jessie's crotch.

"Like what you're feeling?" Jessie asked, breaking their kiss.

"What is that, you wearing a cup?"

"Yes."

"Why? You don't like people grabbing your balls?" Devon asked surprised, letting her grip go.

"Who says I have balls?"

"You're wearing a cup."

"But is it empty, or is it full?" Jessie asked, smiling. "There are more people trying to get a grip on my sex. Maybe sometime I'll let you know. But that time is not tonight. Now where were we?"

Jessie embraced Devon, pulling her close and kissing her again. A passionate, loving kiss, which Devon eagerly answered. She realised that, man or woman, Jessie is simply a good kisser.

When the song finished, Devon returned to the bar, where Taylor and Morgan still were.

"So, what's the result?" Taylor asked.

"Jessie's wearing a cup."

"So it's a guy after all," Morgan concluded.

"Well, only if that cup is filled. And that, we don't know. A girl can wear a cup as well, of course."

"Mmm," Taylor pondered. "That's not going to bring us anywhere. But what if she appears as a woman? Can't wear a cup under a dress."

"Well a guy can tuck away his stuff, add a little padding in the panties, and still you're none the wiser if you try to feel what's there," Morgan commented.

"Indeed. And Jessie also told me he's not about to reveal his actual sex to us any time soon," Devon added. "He wants to remain androgynous. So I'm afraid the bet is off, no blow job for you."

"Doesn't that actually make you two both losers?"

Taylor and Devon looked at each other.

"I think you're right there, Morgan. Good thinking. Seems I can still get to feel your tongue on my pussy," Devon muttered.

"And I'm really looking forward to feel your sweet mouth around my dick," Taylor added.

"Oh, just go and get a room you two, and disappear for the night," Morgan exclaimed.

"That may not be a too bad idea indeed." She moved to Morgan, giving him a hug and a kiss. "Find yourself a hot date, and have a good night. We're off to settle our wager."