A tale from my younger days, exploring my first masturbation session with another person and my frequent peeping. This isn't a continuation from my previous story, 'Rosa's Bra', but rather a prequel of sorts (before I got into music). Once again, it is a fictional reference to my childhood, with basis on fact. Please comment and provide feedback if you enjoy my writing.
The simple lure of the curves of the female body has had me hooked for as long as I can remember. I had, and always have had, so much respect for women and everything they do, but in my hormone induced youth, I could not help my look (and often stare, albeit sneakily). A raging erection was the daily norm and having to wait until I got home for release was sometimes difficult.
As school was where I spent the majority of my time; school was where I did the majority of my peeping. I went to a co-educational school, and girls were everywhere. The bottom half of their uniform was a simple pleated skirt, stockings optional. Neither with nor without stockings was preferred by me, stockings looked incredibly sexy, but well defined, naked legs were held in the same regard.
As we got older, skirts got shorter and shorter, much to my pleasure. Catching a peek up a girls skirt and seeing her thighs and, if I was lucky, seeing the colour of her panties, was one of my ultimate thrills. I often positioned myself purposely to increase the chances of me seeing some panties. One of the main fantasies I masturbated about was any girl from school undressing from her school uniform, and knowing what panties she was wearing that day made this seem more realistic.
Even so, my main fantasy lay elsewhere. I have always had a fascination for breasts, and subsequently, bras. From the young age when I began exploring my sexuality and masturbating regularly this was the main thing I fantasised about. Tight tops, cleavage and looking down the front of a shirt were what I considered to be the sexiest things, but when there was a bra involved, even more so. Seeing a hint of a bra strap on a shoulder or the outline of a bra through the back of a shirt were just as much of a turn on. At school, all types of breasts were on show, small and perky, large and firm. Needless to say, the way they hugged the tight blouses the girls wore and the way they jiggled and swayed had me finding it difficult to concentrate.
My best friend, Mike, was similarly obsessed with the female body, and often just as aroused as I was. We discussed women in the ways expected of young men; constantly debating about who had the biggest breasts, most shapely legs or firmest ass, and of course, who was sexiest girl we knew. Mike enjoyed seeing panties just as much as I did, and we always traded stories of when we were lucky enough to see a pair.
We both knew the other masturbated but never acknowledged it further than that. I had often thought of taking my lust for women further and masturbating together with Mike about what was discussed. Whenever we slept over at each others houses and talked about sexy topics late into the night; it left us both severely aroused, but we were too shy to take it further.
One uneventful Maths lesson, we were both sitting opposite a girl named Kylie. She had recently switched classes into ours and had immediately taken our interest. She was incredibly sexy, and knew it, long, soft blonde hair around a very pretty face with big blue eyes, and amazing 32C chest which she kept tightly hugged by her too small blouse, long and defined legs under a skirt of questionable length with no stockings and a little, firm ass. She flaunted her body and probably secretly enjoyed the amount of attention she got from all of the males around her. We were patient, and our patience was rewarded: at the end of the lesson as she stood up, she flashed us little pink panties with frills around the sides.
Mike and I were grinning from ear to ear as we walked to our next class, Gym, discussing how sexy Kylie was. When we were getting changed, I noticed Mike's obvious arousal in his tightie whities as he started telling me about how he would like to run his hands up Kylie's skirt.
Slowly up her legs, and then squeezing her ass gently I can only imagine how nice it would feel. Mike was an ass man (just like I was a breast man) and his erection mirrored his thoughts on how nice it would feel.
Not to mention running your hands down her blouse, and cupping those tits, man, they would be a handful! was my response, my own member growing in anticipation.
I think you would enjoy that, Mike replied with a half smirk, half smile, throwing an obvious glance to my state of arousal. He did nothing to hide his own though, which throbbed when I mentioned cupping those tits.
I think we both would, I replied with another grin, and to that we both laughed. As we dressed into the rest of our sports gear, I saw Mike give his erection a quick tug. It seemed he was just as turned on by Kylie as I was, and we were both in need of desperate release.
As we walked out of our change room, Kylie walked out of hers and turned and strutted away from us, dropping her bag on the bag rack as she did. This did nothing to aid our state of arousal. She was wearing tiny black gym shorts and Mike was eyeing her ass with some disbelief as he watched it sway from side to side with every step, and I could see the clear outline of her sports bra through her sheer white top.
Mike, clearly losing most of the blood in his head to his now painful erection, whispered to me to follow his lead. I shot him a questioning glance, and then watched as he casually picked up Kylie's bag (pretending it was his own) and walked back into our change room. I walked in as casually as I could after him, and followed him into one of the toilet cubicles, locking the door behind us.
What are you doing? I said, more turned on than I had ever been in my life.
You don't have to stay if you want, but I really can't wait until tonight, if you know what I mean man. She just looks so good! Mike said, blushing furiously.
Do you mind if I do stay? She's turning me on just as much, and I need it, I replied, secretly hoping he wouldn't mind at all.
No, I think it would be kind of hot, you know, not gay, but both of us getting off to Kylie, Mike replied sheepishly.
Yeah I agree I can't wait any longer, I said, and with that I pulled my shirt off and began untying my shoes. Mike started doing much the same, and before long we were both in our tightie whities, together in a small toilet cubicle with Kylie's bag between us.
Mike immediately began rubbing his erection through his undies and seeing this turned me on more then I could have imagined, knowing he was aroused by the exact same girl as me. Did you see how her ass swayed in those little shorts? I said, wanting to help him as much as possible, while beginning to rub my own member.
Oh God, God yes, it was amazing. Mike moaned, now panting slightly with each breath. Her bra too, you could see the outline of it through her top, he added for my benefit, wanting to help me out too. To this, my erection throbbed painfully, and I needed more.
Can we drop the undies? I panted, getting closer to release.
I was hoping you would say that, I'm getting close, Mike panted in reply, and we both dropped our tightie whities at the same time. Looking up, I saw Mike quickly pumping his erection, while stopping to fondle the head every few thrusts, his eyes closed in obvious pleasure. My own member grew harder then it ever had before, and I was similarly servicing myself.
Remembering Kylie's bag, I stopped and quickly unzipped it. What I found lying in her bag made my whole world stop for a moment.
A pink, frilly bra, matching the little panties she was wearing earlier.
I picked it up and held it in front of me. Mike, I said quietly, having reached a whole new level of arousal I hadn't before considered possible.
Yeah? Mike replied, slowly opening his eyes, but still working his member.
Look at....I began, but as soon as Mike saw the bra, his eyes widened and he gasped.
Oh my fuck. That is so hot! Mike exclaimed, and took one of the shoulder straps in his hand, me holding the other. This effectively held the bra in the air between us and we were looking into the cups.
Mike began jacking off as fast as he could, and I knew he was approaching the final stretch. I closed my eyes and did the same, picturing Kylie slowly getting undressing from her school uniform in my mind.
First she unbuckled her shoes and kicked them off sexily before removing her cute little socks. She unbuttoned her blouse and removed it facing away from me, revealing her toned back and the back of her pink bra. Sliding her skirt down over her hips she bent over revealing her amazing ass, and matching pink panties. Turning around, her breasts bounced in her pink bra, and I felt my cum rising.
Almost as if on cue, Mike moaned loudly and exclaimed, Fuck Kylie! I opened my eyes as he began shooting his load into the left bra cup, accompanied by a series of grunts. Seeing my best friend cum over Kylie, and seeing her in my mind with her breasts bouncing in her matching pink bra and panties, sent me over the edge in a spectacular fashion.
My whole body tensed up, and every ounce of feeling I had raced towards the helm of my member. It slowly built up the shaft, getting closer and closer to the edge, before I released my own load into the right cup of the bra. The orgasm lasted for almost half a minute, as I squirted again and again, and the incredible feeling at the head of my erection was mirrored in my mind.
Mike and I came down from our post orgasmic highs together, and smiled sheepishly as we saw that we had both cum in her bra. We decided to wash the bra and then take it home that night (where we were both sleeping over at my house) and continue what we had started.
A few days later, we heard Kylie saying that she had lost one of her bras. Needless to say, Mike and I jumped at the opportunity to aid a damsel in distress; or rather, continue fulfilling our sexual fantasies, but that story is for next time.