Pool Day Takes a Turn

"There's people up ahead, watch out!" I yell into my headset. It was just a typical Sunday. I was gaming with some online buddies of mine, relieving myself from the stress of the work week. I work a tech support job 5 days a week, Tuesday-Saturday, so Sunday is my day to unwind. I got a text from my good friend Nick that I hadn't seen in a while. He asks if I want to come over and hang out with him and while I do like to relax on Sunday's, I hadn't gone out in a while, so I agreed. I finished up my game, put on a t-shirt and some sweatpants, and headed to his house.

Upon leaving, the wave of heat hit me like a ton of bricks. I spend most of my time inside as of late and hadn't noticed the temperature change. It seemed warmer than usual for a mid May day and shorts would be the right choice of attire, but all of mine were dirty and had yet to be washed, so I continued on in my sweatpants.

I arrive at Nick's house and notice his girlfriend Angie, an old friend of mine, is there as well. I say my hello's and after the small greetings, Angie gives me a big hug, stating how much she missed me. She looked stunning, dressed in a tiny two piece bikini, with a pink top and a flower design on the bottom. The bottom was Brazilian cut, that her ass absolutely swallowed. Nick was ripped to shreds, shirtless in his bathing suit.

"Bathing suits, huh? I didn't realize you had a pool?" I ask. I wish he would've told me they were hanging out in the pool, I would've brought my suit, but I wasn't going to drive all the way back home now.

"Oh yea I guess it has been that long. We got it put in last summer, come on let's check it out," Nick responds.

We stand on the deck, chatting it up. The weather is horrible. The heat was eating us alive. Nick decides to dive in the pool, leaving me and Angie on the deck.

"Damn, I wish I brought my bathing suit. This heat is something else. I practically feel like I'm dying out here."

Nick overhears from the pool, "Just borrow one of mine. Angie take Randy into my bedroom and find something for him to wear."

I follow Angie into the house, past Nick's parents, giving them a wave. Inside his room, she starts looking through his swimwear. She throws me a pair, and I size it up. It's way too big for me. I'm a small guy and would be lucky to fit into a medium. There was no way I would fit into a large. Still, though, I go into the bathroom to try it on, and as expected, too big. I show Angie my dilemma and she just shakes her head.

"Why don't you just go in your underwear?" she asks.

I mentioned how I hadn't done laundry recently and all my shorts were dirty. The same went for underwear. They were all currently in the wash and I didn't expect to leave the house today, so I didn't exactly need them. I didn't want to reveal to Angie I was going commando, so I replied flustered, "Uhh no no... I don't want to do that."

I look out the window to see Nick swimming in his pool. Even with the air conditioner on in the house, I could feel the heat. All of a sudden, I feel a tap on my shoulder. I turn around to see Angie with her hands behind her back.

"Randy, I have an idea, but you have to promise not to get mad at me, alright?" She had a devilish smile on her face.

"Sure, I won't. What is it?"

She reveals her hands from behind her back to show me a pink, one piece, bathing suit. I was appalled. Why did she think I'd be okay with this? There's no way I'd walk out there in that thing... or so I thought.

"Just try it on! It's a one piece so it's full coverage. Feel it, it feels so nice."

I run my hand over it and I start to get goosebumps. It does feel really nice. Old memories of me trying on my mom's panties when I was younger come flushing back to me. I am a closet crossdresser, who hadn't practiced my habits since I was almost discovered by my father. It started innocently enough, with my mothers things being mixed into my laundry basket, but upon feeling the material way back then, I knew I was hooked, and trying them on was icing on the cake. I became addicted and if it wasn't for my father being seconds away from walking in on me wanking it in her panties, I would have never stopped. Those feelings still run deep inside me, but I try desperately to forget about them. Still, though, this was the opportunity of a lifetime. I grab the bathing suit and hold it up to myself.

"Angie, there's no way I can fit into this! Look at it!" It was true. The suit was very small, but at the same time, I was a small dude. I also didn't want to let out how I truly wanted to put it on.

"Yes you can! Nick's suits you definitely can't, they'd be falling with every step you take. Sure, this one may be a little tight, but it won't be too restrictive. It stretches out. Try it on. Let's see it."

I reluctantly agree. Even inside in the cool air I was sweating bullets. Going back outside in my sweatpants was not an option.

"Fine, I'll try it on. But you can't tell anyone about this."

I undress and step into the bathing suit. As expected, the suit was extremely tight. The back went straight up my crack, and despite it being a one piece, I felt like I was barely covered up. It covered my package fine, but I still felt so exposed. I walk out of the bathroom to show Angie and she screams with glee.

"That looks great! Here, turn around." She grabs my hand and twirls me around and pinches my butt. "Oh my god your ass looks great in this!"

I'm not sure why but I took that as a compliment. I fumble out a thank you. She continues, "And oh my god I can barely see your dick through the front of the suit. It must be so small! You were born to wear these types of bathing suits."

Before I could respond to that, Nick calls out, "What's taking you guys so long! I'm getting bored out here!"

"Coming!" Angie yells and she pulls me back out into the backyard.

Nick doesn't seem too thrown off by my choice of bathing suit, and even compliments me.

"Randy, you look great. Come on and jump in the waters fine."

I blush as Angie and I both jump into the pool. First we're just chilling in the pool then we decide to do some pool basketball. Whenever I had the ball, I noticed Nick rubbed up against me a bit more than one normally would, but I didn't think much of it.

Eventually, we get out of the pool and are back on the deck. There's a table with only two chairs, along with two towels on each of them. Both Nick and Angie take their seats and the towels accompanying them and start drying themselves off. I'm left standing there, shivering slightly. Even though the heat would warm me up quickly, I was still a bit uncomfortable at the time.

"Go ahead Randy sit on Nick's lap, he'll dry you off and warm you up," Angie says.

I'm hesitant to do this. I feel slightly weirded out, sitting on my friend's lap, especially dressed like this but Nick taps his lap.

"Come on, man, don't be weird about it. You need a place to sit and I have a towel here to get you dry. Just sit down, it's fine."

I walk over slowly and Nick grabs my wrist and pulls me onto his lap. He first uses his towel to dry me. Once he does that for a bit, he places the towel on the table, but continues to rub me with his hand and arms. The three of us start talking. I notice I've drifted further into his lap. He goes from rubbing my arms, to rubbing my bare thighs. All of a sudden I feel something hardening at my backside and I immediately know what it is. I begin to worry a bit, but for some reason, it's turning me on and I start getting an erection of my own. I've never been attracted to men, despite my attraction to wearing womens underwear, but being out here, dressed like this, it just felt... different. I snap myself back to reality. I can't have these thoughts. I'm straight! My family would practically disown me if they thought I was gay or worse, wore womens clothes. But still, I felt what I felt, and I was getting increasingly horny by the second. I close my eyes, trying desperately to fight it off.

"Are you guys done in the pool already?"

My eyes dart open and I see Nick's mom coming over to us with a tray of margaritas. As she hands them out she says, "Oh, Randy, I just love your bathing suit."

I'm flushed red with embarrassment as I had known his mom for years and didn't want her to think I was some sort of weirdo. I was sitting on her son's lap, with a women's bathing suit on after all! But, I thought to myself, she said she liked it, didn't she?

"Thank you, Mrs. Johnson."

"Why don't you stand up and give me a little twirl?"

Still hard, I'm reluctant, but I look down and see my erection isn't really showing. One of the advantages of having a small dick, I guess. I stand and spin and she is giddy with excitement, much like Angie was.

"Yes, yes, yes," she says, clapping her hands. "You look so good and I never realized how cute and petite your body was. It's because you always wear those baggy, gross boy clothes ugh. I've never been able to see your body. I'm glad you've decided to do away with that. Next time you come over I'll give you one of my bathing suits to borrow. Do you like the way that one fits you?" I'm slightly confused. Does Mrs. Johnson think this is a permanent change in style, or does she think I just prefer to wear womens bathing suits to mens for some odd reason? I respond to her as politely as possible.

"Yes I do, Mrs. Johnson."

"Perfect, because I noticed that one's a bit skimpy, and I have this tiny little red one I'd LOVE to see on you. Look at you! Your cute little bubble butt is so hungry, it's absolutely swallowing the bottom of that suit! If we were on a beach we wouldn't be able to keep prying eyes off of you."

"Thank you, Mrs. Johnson," I say embarrassed.

"By the way, Randy, a little piece of advice. That suit would feel so much better on you if you had shaved your legs."

I lower my head. I didn't have much leg hair, but it was enough to notice.

"Next time you're here, I'll see to it that you're completely smooth. Oh you look so cute! I could eat you up right now." She says giving me a big juicy kiss on the cheek. If I wasn't hard before, I am now. Nick's mom is a smoke show and I couldn't help but imagine her in that little red bathing suit she was talking about. But wait, she wanted me to wear it? I do have to admit, Angie's suit did feel great, and I was having such a good time today, I wasn't exactly opposed to the idea of doing it again. Plus, no one made me feel weird about it...

"I'll let you three carry on. By the way, did you want me to bring out another chair for you?" Before I could answer, Angie chimes in.

"No, he's fine sitting on Nick's lap. He seems to be enjoying it," Angie said with a wicked smile.

"Okay, no problem. I'll come back in a bit to check on you guys," Mrs. Johnson said, turning around and leaving. Her fat ass swaying in the skirt she was wearing.

So we continued talking, now drinking, and the margarita was getting to me. Being smaller, it doesn't take much to get me drunk, but this margarita brought me to another level. Mrs. Johnson must have loaded it with alcohol.

"You know, they say if someone licks your elbow you aren't able to feel it," Nick says.

"Stop it, that's such bullshit," I playfully said back to him, slurring my words, drunk from the alcohol.

"It's true, I'll show you right now." He bends his head down and licks my elbow, but he doesn't stop there. He brings his tongue up my arm up onto my neck and gives that a fat kiss. I laugh pulling away from him, as I hear a camera flash. Angie had just taken a photo of me and Nick.

"Angie what the hell!" I say still laughing, "I don't want myself in your swimsuit on record."

"Oh, but you just looked so cute here." She shows me her phone and it's Nick giving my neck a fat kiss as I have my head tilted, with a huge smile on my face. Looking at myself for the first time in a while, I saw how I looked in this bathing suit, and I must say, aside from the lack of boobs and light leg hair, my body did look very feminine. For the first time in my life I was disgusted by the fact that I had leg hair. I wanted so badly to shave it off. The big smile on my face made it seem like I really enjoyed Nick's kiss. While I did, it was very obviously myself, Randy, in the photo, and I didn't want anyone who may see it to think that.

I protest for her to delete it but she holds firm, saying she won't share it and that it's just a memory. We continue talking and Nick continues rubbing my thighs, getting closer and closer to my groin area each time. The constant touch is getting my dick hard as I tune out of the conversation and start rocking back and forth on his lap. He meets my movement with movements of his own, and I feel his hard dick rub between the small material wedged in my ass. His hands come up even higher and he grabs my dick through my one piece. Before I can object he kisses my neck again but this time more sexually. He sucks on my neck while rubbing my cock through my suit, as I feel him shuffling with his off hand, lowering his bathing suit. He is basically rubbing his dick into my almost bare ass, as I moan in delight. I feel close to cumming but before I can he stops. He instead brings his hands to the back of my suit. Nick takes the bottom portion out of my ass and inserts his dick into my hole. I scream out in pain and as I do, I see both his parents coming outside in swim wear.

I quickly close my mouth and try my best not to make noise. They give us a quick wave and dive into the pool. The angle of the table makes it so they can see I'm sitting on his lap, but they can't see exactly what's going on underneath. Nick lifts me up and down on top of his lap as soon as his parents were on the far side of the pool and out of the pool. I start working myself, pushing down on his dick, quietly moaning in delight. I look ahead of me to see Angie recording the entire thing. I can't even protest it. I was lost in bliss.

I continue riding him reverse cowgirl style and he starts getting more aggressive. I can't hold my voice any longer as I moan louder and louder. He pulls me completely out of him, then quickly lodges himself back into my hole and I practically scream. Nick's mom swims back into view, and asks if everythings alright.

"Yes, Mrs. Johnson, don't you worry. Everything over here is just fine," Angie responds.

She swims back out of view and we continue. I bounce up and down on his dick as I hold onto the sides of the chair. I can't hold back any longer.

"I'm gonna cum. I'm gonna cum."

"I AM TOO SLUT. TAKE IT, TAKE IT DEEP IN YOUR ASS. CUM AS I CUM," Nick says loud enough to where I'm pretty sure his parents can hear.

He explodes in my ass and it triggers me to cum as well. We stay panting with him still inside me. I collapse on the table and try to catch my breath. I look down and see the front of my bathing suit is wet and soaked with my cum. I look over to see Nick's parents exiting the pool. I lock eyes with his dad as he shakes his head with disgust and walks inside. Mrs. Johnson exits the pool next and looks at me with a mischievous smile.

"You just couldn't resist, huh? Well I can't blame you, my son is a bit of a stud. Nick, are you still inside her? Pull out already, so I can help clean her up." Nick pulls out of me and in my state of post orgasmic bliss I barely register Mrs. Johnson referring to me as a girl.

Mrs. Johnson helps me up off of her son's lap as cum immediately starts leaking out of my ass. She quickly yanks up the bottom of the bikini, wedging it up into my crack.

"There you go baby. It's still going to leak a little, but that will help it out." She gives my bottom a couple slaps. "I guess your little butt was pretty hungry, huh? Here let me take a look at you."

She stands back and sees the state of disarray I'm in.

"Aw man, you ruined that cute little bathing suit. Don't worry hun, I'll just bring you inside and get you all cleaned up. I have something for you to wear."

With that, she takes my hand and leads me inside, as I feel the pool of cum collecting into the small fabric of my bathing suit.