A Swimsuit Contest 1

By Jake.

So my girlfriend Kayla and I run with a large group of friends. There are six couples, and we do everything together. Holidays, vacations, you name it. We were on a long weekend trip to the lake when the power dynamic changed dramatically for me, at least.

The lake house was beautiful. It was a family property of Steve and Jessica. We all met there Friday at our own pace. When we got there, everyone was already at the lake. My girlfriend and I took advantage of the opportunity and began to make out and fool around in our room. She pushed me onto the bed and jumped on top. Between her leggings and my gym shorts, we were dry humping as we made it. This, of course, was too much stimulation for me and came quickly. She didn’t notice, so we kept making out until she suddenly jumped up.

“Babe, why are my leggings wet? Wait, did you cum from that?”

Embarrassingly I replied, “Yes.”

She shucked her leggings and said, “Well, it’s my turn then,” as she sat on my face.

Hearing her moan was hot, and before long, I felt like I was getting turned on again. I tapped her leg so she’d get up enough for me to speak. “Hey, I think I’m ready to go again.”

She turned around, sat back on my face, and giggled. “Wow, my big man’s ready for me. Do you want me to suck your clit or lick it?”

Man, I couldn’t hear this. When Kayla said ‘dick,’ I swear it sounded like she said ‘clit.’ I nod yes, as I don’t care how she does it. I want her to go down on me. She tickles right under my nuts and begins to flick my dick with her tongue. It was all too much, and I came again within five to ten seconds of her starting.

“Alright, stud, that’s enough for now. Let’s join the others.”


We had a relatively typical day at the lake. Lots of suns, beer, music, and company. All the men acted like horn dogs, and all the significant others wore hot bikinis. After dinner, everyone was ready to hop in the hot tub. Most didn’t change suits all day. Everett insisted he changes. He came out in a speedo, and let me tell you; nothing was left to the imagination. Kayla was visibly flustered.

Everett’s wife just laughed, saying, “Oh, good grief. No one wants to see that.”

“Speak for yourself,” one of the other wives said.

He got in the hot tub, and everything calmed down.

Several hours later, the girls returned from the house giggling. My wife seemed somewhat nervous as Everett’s wife declared, “We’ve decided there will be a competition.”

That’s a regular occurrence at these events.

“Since all the women and Everett are wearing far less than you other five,” Everitt’s wife said, “we’ve decided it’s only fair we see how all of you look in similar suits. Before you all start backing out, remember there will be consequences all the ladies agreed to. First and foremost, no sex until our next trip, which you already know is a month from now. And if that’s not bad enough, you all will have to wear a shirt during the next trip stating you chickened out of this competition. All right, now that we’ve set the tone. The competition is you will all don a speedo similar to Everett’s.”

One of the guys chimed in, “Yeah, super, don’t own one, let alone have one here.”

She replied, “Already ahead of you. Your wives gave me your swim trunk size a month ago for what I described as a first lake trip of the year gift. See how I left it vague. So anyway, I gave them the speedos while we were inside, so get to it. Oh, wait, sorry, I forgot to mention the stakes. The six women will vote on who looks best in a speedo, like a swimsuit contest. The winner gets to ask to see one of our boobs. The loser has to put on his wife’s bikini bottoms.”

So we all headed inside to change. Now, if you haven’t picked up on it yet, I was less than fully aware of how I stack up. I knew I was no Everett in the package department, but I was in no way worried about the competition. In reality, I am tiny (about an inch soft and a whopping three inches hard). We get to our room, and Kayla still seems nervous.

“Hey, don’t be nervous. I’m wearing the Speedo, and I got this,” I said.

She replies, “You seem confident.”

“I am. Look, I know I’m no Everett in that department. I think I stack up well to the others, and I never hear you complaining when I rock your world.”

“Alright, then, hot shot.” She forgot to mention the final rule. No erections (I’d soon find out this wasn’t a rule but a punishment for my cockiness). “Now strip so we can get to it and change. I know it takes a long time to get you off.”

That last part was somewhat sarcastic, but I chalked it up to the situation and dropped my trunks. Between the drinks and hot tub, I was feeling a little deflated. Kayla didn’t pass up the opportunity saying, “Wow, my big man!” She cupped my entire package in one hand and began to massage my dick with two fingers. I wasn’t getting any bigger between the alcohol and two previous orgasms. “I’ve got an idea. Lay down.”

So I did. Kayla climbed on top and slid herself up and down my crotch. “Damn, that feels good,” I said.

Kayla replied, “This feels much better than when we try to keep you on me.”

I want to say I got hard, threw her off, and fucked her for ten minutes, but that didn’t happen. About thirty seconds later, I started cumming despite never getting hard. Kayla continued to ride my soft near innie using my cum as lube until she also orgasmed.

I cleaned up and slipped my Speedo on. It wasn’t very flattering in my post-orgasm state. Given my three orgasms, even my balls were pulled tight. The front pouch of the Speedo just kind of hung there.

The guys gathered in the kitchen while the girls got ready to judge in the living room. I could tell I didn’t stack up well with the ones there. Some were bigger than others, but none looked as pitiful as I did. Thankfully Sam wasn’t there yet. I assumed he looked worse than me and was trying to figure out a way to avoid it. Right before the big reveal, Sam showed up. It looked like he’d smuggled a small animal in his Speedo. So we went out.

There was loud applause for Everett and Sam, moderate excitement for the middle three, and complete silence when I walked out.

One of the women even turned her head sideways, trying to figure out what was happening. After deliberating, the guys were brought in, and Sam and Everett declared a tie for the winner. They both decided they could pick a woman to take off her top. Everett picked his wife (wise man), and Sam picked Kayla.

Kayla said, “Only if you come here and untie me.”

Much to everyone’s surprise, Sam was happy to do so, freeing her beautiful C-cup breasts. Sam reminded everyone, “Isn’t it time to declare a loser?”

Kayla replied, “Yes, it is. By unanimous vote, my boyfriend Jake is the loser. Let’s go, sweetie. You have a wardrobe change to attend to.”

I objected. “There’s no way I’ll fit.”

“Oh? Do you want to double down?”


“Perfect,” Kayla said. “If my bikini bottoms fit you, or better yet, if you fit in them, then you must wear women’s bathing suits and underwear exclusively for the duration of the trip.”

“Deal,” I said.

So we head inside. I chuck the Speedo, ready to end this embarrassment. There’s no way we’re even the same waist size; she should have thought that through.

Kayla asks when we enter the room, “Do you want a one or two-piece?”

“I’m pretty sure the bet was just the bottoms,” I said.

“OK, suit yourself. Do you want pink or floral?”

“Doesn’t matter. They aren’t going to fit anyway. You pick.”

“Alright, pink it is,” Kayla said.

“Geez, babe, that’s a string bikini. Do you want it to be easy?”


So I went to put on the pink string bikini. The first thing I noticed, it was stretchy. The next thing was it was sliding up me as if it would fit my waist (of course, Kayla had adjusted the ties to ensure it would fit). No worries, my balls will spill out the bottom. Nope, too many orgasms later. They were nonexistent next to my body. OK, this is a women’s string bikini; no way my dick fits inside it. But there it was. The material was both stretchy and compressing, so I was left with nothing resembling a man’s bulge in a women’s bikini. When I realized it, I threw my hands over my crotch, but Kayla was ready and had already taken pics of both.

“Alright, boyfriend. Let’s be honest: you look more like a girlfriend right now. Time to face the music. Shouldn’t have been so cocky with such a little dick to show for it.”

And out we went.

Everyone lost it.

Kayla said, “So, did he lose the double down?”

And everyone yelled “YES!

We got questions all evening. “How do you guys have sex?”

To which she replied, “Just like you would think. Like lesbians for the most part.”

“There’s no bulge at all. It looks like you have a pussy,” someone said.

Kayla said, “He might as well. It’s small, doesn’t get very hard, and he finishes quickly.”

I was ready by bedtime. I didn’t argue as Kayla handed me a pair of silky white panties. Once we got in bed, she was the big spoon and spent the night constantly rubbing me through the panties right up to the point of orgasm and then stopping.

She finally let me finish when I agreed to repeat, “Please rub my clitty through my panties. I’m so horny and need attention.”

I came with a whimper as I said it.

What further embarrassment will the rest of this trip bring?


To Be Continued…?


*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story was submitted directly to this website.


  • ryan

    fantastic story! having to wear the bikini bottom and TOP the rest of the trip should lead to some very deep dark sissy tan lines!!

  • smallwhitedick

    I love it. can’t wait to read the next part 🙂
    I cumed as much as Jake reading this story.


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