A/N: Starting to realise that a storyboard might be in order, but hopefully you'll understand why this isn't written like a well-planned series, and more of a loose connection of scenarios I find hot. I promise to work up to an actual sex scene.
Also, I got really stuck on trying to write a female orgasm scene, feel free to hum with suggestions.
********
Madelyn walked along with a spring in her step, and my eyes bounced up and down with her as we left the pool. There was no denying her beauty and appeal, my eyes were practically glued to the state of her clothes. Our little antics at the swimming pool had left her in an absolute state, and she was proudly showing off the aftermath to any unfortunate passers-by. Her hair was slowly drying, but with clumps and strands sticking out from the cum in her hair. Her clothes were not much better, her unzipped hoodie still showed off her swimming top, splattered all over with cum, little pale dots and streaks slowly forming as it dried out. I could only imagine the same was happening to her swimming trunks under her skirt.
"Hey, quick, take out your phone and record this." Madelyn tugged at my hand like an excited little child, before turning round to face me. Once my phone was recording, Madelyn flipped her hoodie jacket so that it was resting on her elbows, her cum-streaked top on full display. She brought both hands up to her breasts and started fondling them through the top, the tight fabric holding them in place, jiggling in her hands as she massaged them. She then slid one hand down her stomach, the other down her side, and pushed down on the waistband of her skirt, just low enough so that the top of her bush was showing.
I was wrong about her keeping on the swimming trunks. She was walking with breeze.
Madelyn let out a cheeky giggle before turning back round and taking my hand, though not before leaning over to make sure I had taken the video properly. "Oh yeah, that's hot." She slithered her arm around mine as we continued to the station.
"I have to say, Madelyn, I'm starting to think that you're a lot dirtier than you normally let on."
"I mean, obviously, can't really go around the office like a raging whore, dummy."
"I was thinking more of how you're normally quite prudish in the office."
"Well, now you know I'm not. I like it rough, and you'd better live up to my expectations..."
"Try me."
"Tell you what, let's take a detour, I know a toy store nearby, let's grab a few things there to help us along."
"Sure, or maybe we'll find yours." To be honest with myself, I was a bit taken aback, I had never done much more with a woman other than with a vibrator, everything else had been mostly vanilla, if not a bit rough.
The two of us headed off towards a nearby adult store. The building itself was quite old looking, probably about 50 years old, and the store itself was four flights of stairs up, which graced me with a wonderful view of Madelyn's skirt and lack of undergarments. I opened the door to the store, where a freezing blast of air conditioning greeted both of us. We walked through the shelves of lube, toys, and kinky outfits. "First things first." I muttered, picking up a pack of condoms. "I guess I should've packed some today, but I thought otherwise.
"Well, some might consider it presumptuous if you bring condoms just to go swimming with a lady, but you would've gotten a pass since I've been touching myself silly thinking about you anyways." Madelyn led me towards the dildo section and teased. "You sure you aren't going to be intimidated by a bigger one?"
"Go ahead, just don't blame me when I use it to run you ragged later."
"Thanks. Why don't you take a look at some other toys we might use. I'd feel more comfortable choosing one when talking with another girl."
"Um, sure." I didn't really understand why talking to a stranger, even another girl, would be easier than discussing the choice with a close friend turned lover, but if she felt that was the case, I had no need to intrude. I walked off to the couples toys section, filled with gags and handcuffs, whilst Madelyn approached the young lady behind the counter. I looked at all the toys on display, most of which I had only ever seen in pornos. There were themed handcuffs with police department logos, and fluffy white mink ones as well. Some more extreme tools such as sex swings, latex bodysuits, riding crops, and "romantic hot wax candles"? I was getting a bit lost. I figured I might as well stay with the basics, and picked out some fabric handcuffs and ropes I recognised from... well you know. As I was eyeing some roleplaying outfits, Madelyn walked up next to me, holding something behind her back. "I got my little surprises, is there anything you're interested in?"
"Honestly, I haven't really done much of anything with toys before. I mean, there's rough sex and then there's the kink-based stuff. Not judging, just... I've never done any of it."
"Fair enough, I've never tried the stuff I just got either, just thought that they'd be hot. Just pick one, if it doesn't work for us, it doesn't work, no hard feelings."
"Alright then." I picked out the fluffy handcuffs and a rope harness. "Let's see what we can do with these."
"That's the spirit! Ooooh let's get an outfit! What'd you think, me as a sexy little schoolgirl?."
It was oddly appealing as an idea, thinking of Madelyn as a secondary school student, but it also felt so very very wrong. "Maybe this instead, I think it suits you well." I picked out a beautiful red qipao style outfit, complete with the tight waistline and old fashioned Chinese buttons, made perfect for the occasion by way of high slits that ran up all the way from her legs to just under the side of the chest.
"Ooh, I love that one! Traditional and sexy, perfect! Lemme see..." She rifled through the rack. "The sizes are pretty standard so... This one! Hiya, can I get one in my size?"
******
Madelyn and I stood on the subway towards a nice hotel a few stops away. "I'm not saying I regret doing so, but wearing the swimsuit for this long is starting to get a bit uncomfortable." Remarked Madelyn, a bit louder than expected. "Also I'm starting to smell the cum on me."
I held in a chuckle and pointed out to her, "I think someone might have overheard." A group of teenagers standing together down the train were now shooting furtive glances over towards us, well, towards Madelyn's frizzy hair and streaky top. The boys had eyes as big as dinnerplates, and the girls switched between looks of disgust and shock.
"Awww" chuckled Madelyn, how adorable of them. She picked at her swimsuit top, letting it snap back, sticking to the curve of her breasts, and pinching around her chest to make her nipples poke through. "I bet they won't forget this in a hurry."
"You dirty dirty girl, in front of a bunch of teens? Are you sure I shouldn't just call the cops?" I teased, before taking her in for a kiss. Slowly, she slid one hand down her skirt as she pressed the other one against my chest, slowly sliding down, and cupping my rapidly hardening dick through my pants. "Jesus, Madelyn, really?" She flashed a smile, and continued to rub up against me.
The sudden jolt of the subway car shocked us back to attention as we arrived at our station. We quickly hopped off, chuckling at the sight of the teenagers, their eyes still fixated on us, well, Madelyn.
***
When I entered the bathroom, I was greeted by an extremely erotic Madelyn, standing under the water, leaning backwards with her hair down, using her right hand to play with her pussy. Her left hand was behind her, holding onto the side of the shower. She closed her eyes and bit her lips as she continued to rub herself.
"I thought you wanted to wash your hair first." I joked, taking the shampoo and gently lathering her scalp. Madelyn backed up closer to me, pressing her back into my chest, and her ass against my crotch.
"Mmmmmm... I mean, you're here helping me right? Let me enjoy this." She murmured, continuing to finger herself. I began to shampoo her hair, massaging her scalp and running my fingers through her hair as she slowly grinded against me.
My cock had grown painfully hard, and was straining against her ass. I gave her another spritz of shampoo and leaned down to her ear, whispering, "Oh don't worry, I'll have you in ecstacy soon." I kissed her neck and trailed kisses downwards, brushing my tongue against her earlobe.
Madelyn moaned and shuddered. She turned around and wrapped her arms around my neck, pressing her body against mine. My cock was trapped between us, rubbing against her stomach, so tantalizingly close to bliss.
I lowered one hand to finger her folds, my fingers dancing deftly around her sex. My fingers flicked up and down until they found a bump, causing Madelyn to let out another moan. I hunched over a little to give myself a bit more leverage, and started pushing up against her clit as I massaged her. Madelyn was panting and gasping as I continued to finger her, and continued as I straightened up and turned her around.
Pulling her into me, I wrapped one arm tightly around her, and continued playing with her using the other. Madelyn couldn't do much more than squirm, trying to arch her back as I slowly sped up my touch. I continued on, adjusting my fingers in accordance with the pace of Madelyn's breathing, getting her closer and closer. "ngghhh... fuck, don't stop, don't stop." Madelyn gripped the sides of my thighs, her fingers clawing into me as she shuddered and moaned.
