One of the Girls Ch. 02 - The Pool

Days have passed since the stripping incident, and I haven't even talked to Megan since, but I have jerked off to that picture of her tits at least 20 times.

I'm just not sure how to talk to her again after that humiliating night, I'm sure she thinks less of me after running home in pink princess panties, so what could I possibly do now to try and salvage any form of relationship?

I'm minding my own business throughout the day until surprisingly Megan texts me asking to hangout today. Truly a perplexing situation, on one hand I do still like her, but I'm not going over there again just to get humiliated by her friends, so I text back "I'm not so sure". She responds with "My friends won't come this time, it will just be us". This immediately changed my attitude, just us, all alone? It doesn't take much time to tell her yes and get really excited about seeing her.

I get in my car and start heading over, she texts again and I only see the first part as I'm very focus on driving and refuse to use my phone "Oh and don't forget to bring..." I really wish I caught the rest of that, but I can't afford a ticket for texting and driving, plus I'm already halfway there, it wouldn't be convenient to turn back for anything.

I get to her house and she answers the door, she notices that I'm nervously looking behind her "It's okay silly, they aren't here" she says reassuringly. She then says "Did you remember to bring a swimsuit?" So that's what she texted, I completely forgot once I got there. "Oh no I'm sorry, I didn't see your text." She says "It's okay, I just really wanted to go swimming with you." Now I feel horrible, not only did I make her sad, I also lost my opportunity to see her in a swimsuit, so I say "do you have a brother I can borrow a suit from?" She responds "No, I only live with my mom, but I... Nevermind..." She cuts herself off. "What's that? I'm willing to do whatever it takes to make this work" I am becoming more determined. "Well I do own two different suits, perhaps you could borrow one..." I cannot believe I'm getting put into a situation where I wear women's clothing again. "I'm not so sure..." I say when she starts tearing up a bit, I didn't know this meant so much to her "Okay can I see the options first?" I say immediately regretting, but she perks up and she grabs my hand and leads me to her room.

She pulls out the two suits, one is a black and white striped bikini, the other is a one-piece light blue swimsuit, both seem like bad options but at least one would cover me more... I say shyly "I could wear the blue one" she gets very excited and hands it to me "You're awesome! You can go get changed in the bathroom!" I smile hearing her compliment me, but now I am forced into crossdressing again. I get naked and stare at the suit, it at least look normal, maybe I can pretend it's a wrestling singlet. I put it on and it's really comfortable, it feels very light and free, but then I look in the mirror and feel embarrassed again. It's so thin I can see the entire outline of my little dick and it also shows a considerable amount of butt check. It's almost looked like I was checking out a woman's ass, was mine always this feminine? I must have been staring for too long because Megan knocks at the door asking if everything is okay. I respond and open the door, covering my crotch. She blushes and says shyly "You look really cute..." I couldn't help but notice how cute she looked in the bikini, I respond "You too..." We both then head outback to her pool.

I stare into the water, if I get in, I am committing myself to swimming in a women's swimsuit, I'm contemplating when Megan just pushes me in! She then jumps in as well. I emerge at the surface when she comes up behind me and hugs me "Thanks for coming over" she says sweetly. We then have a lot of fun playing in the pool, so much that I completely forget that I'm wearing her swimsuit. We bounced a beach ball, played with water guns, pool noodles, etc.

I decide to grab her gun and take it away to tease her, I had it up out of the water where she can't reach. "Hey! That's no fair, I'm defenseless!" She swims up to me, her breasts are pressed against my chest as she reaches up for the water gun. I blush and stare into her eyes, then she stares back. Then in the moment we kiss. Never expected my first kiss to happen like this, but I'm certainly not complaining. We kiss for a good few seconds until she feels my boner poking her leg and she pulls away. "Sorry for that..." She says blushing immensely. "No, no, I'm glad..." I awkwardly say smiling.

She then decides it's about time to dry off, when I get out I'm once again covering my crotch, but this time it's because I want to hide my erection. We dry off and I head to the bathroom to change, I notice that the swimsuit has ridden up more than before and most of my ass was on display "That's it" I think to myself "No more crossdressing."

I change and meet with Megan before I leave "Thanks again for coming over, it was a lot of fun" she says, I respond with "it was a lot of fun coming over!" We then hug before I walk out the front door. I drive home, thinking about everything, and despite the weirdness that came with wearing the swimsuit, this was definitely the best day ever.