Did It Really Happen?

As I get older, I find my thoughts drifting back, more and more often, to that one night, 20 years ago. Though it consumes my thoughts, sometimes I still find myself questioning whether it ever really happened. Was it just some adolescent fantasy that I've managed to fool myself into believing actually happened to me? But then I close my eyes and it's like I'm right there again, in that tiny one room apartment. I can remember every minute detail: the precise placement of the beads of sweat on the small of Heather's back, the texture of the ribbed cotton on Carlie's tank top, the sounds of the x-rated movie playing in the background. And just like that, I'm rock hard. Twenty years later and it still does the trick instantly.

It was mid-July. I was a year out of college and working in Japan. I had a small, one room apartment on the outskirts of Osaka. Two of my best friends from college, Heather and Carlie, had flown all the way out to Japan to visit. We'd been through a lot together, backpacking through South America the summer before, staying in hostels and sharing dodgy hotel rooms. Once upon a time, there may have been some sexual tension between us - Carlie and I had even kissed a few times early in college - but we'd long since moved past that and settled into a very comfortable, very honest friendship.

Both Heather and Carlie had very similar personalities, which is why they were such good friends with each other. Neither had any real filter and would say whatever was on their mind. Carlie in particular had a habit of talking very candidly, and descriptively, about her sex life, which was quite active. Heather too was candid to a fault, and could cuss like sailor. Being around them had been an educational experience to say the least. I'd learned more about sex from listening to them talk than from any actual first-hand experience, and I don't mean to suggest that I was some sheltered virgin. But being with them always made me feel like I was sitting in on some private conversation that I was never meant to hear. It was almost voyeuristic. And as a bit of an introvert, being around them was healthy for me. It drew out a more honest, less inhibited side of myself.

Although I rarely noticed her appearance, I can still picture what Heather was wearing that night. She had on tight blue jeans and a baby blue tank top with a tiny white flower pattern. The jeans accentuated her hips, which were easily her best feature. She was pretty but in a plain sort of way. Long, straight brown hair. A small chest. Always a bit of a tan.

It was a typical sweltering summer night in central Japan, the last night of their trip, and we'd been out drinking and singing karaoke at a place down the street from my apartment. As we walked back to my place, I caught myself staring at Heather's hips as she walked in front of me. I'd seen her naked several times during our South American travels. She'd gotten to a point where she was so comfortable around me that she didn't even bother trying to find another room to change in. I could tell this immodesty bothered Matt, her long time boyfriend, who had also been on the trip. But Heather was either oblivious or just didn't care.

Carlie was very different physically. She was short, with curly brown hair. Her glasses gave her a bit of a bookish quality. She was attractive in a sexy librarian sort of way. But the thing you couldn't help but notice about her was the enormous size of her breasts. For a petite girl like that, they were really something else. And she couldn't help but show them off. There was no way to hide them. On that night, she too was wearing a tank top, a ribbed white one, with an unbuttoned blue shortsleeve shirt on over it. She had on short khaki shorts that showed off her skinny legs. Heather joked that she looked like a shorter, slightly more Jewish Lara Croft (Lara Croftberg, she'd cracked).

I had always been attracted to Carlie and was very up front about it when we first met. She had a boyfriend at the time (she always did) but she strung me along for a bit anyway, making me think we had a chance. We even kissed a few times. But I eventually realized that this was her M.O. I wasn't her type; she just liked being wanted. She liked that I liked her. Once I came to peace with that, I just moved on, and we transitioned into a very comfortable friendship.

At the time of the Japan visit, all three of us were in relationships. Heather and Matt were going strong. Carlie was dating some older lawyer back home. And I was in a pretty exciting new relationship with a fellow ex-pat in Japan. So there really wasn't any noticeable sexual tension between us and there hadn't been for years. There was no reason to expect anything but another night of talking and laughter among old friends.

When we got back to my apartment, I cranked up the wall-mounted AC unit, but it was still very hot and muggy. We cracked open a few 22 ounce Sapporos we'd picked up from the vending machine outside and drank them as we reminisced about Argentina and various other shared adventures we'd had of over the years. I sat on my twin bed while Heather and Carlie sat on their respective sleeping bags with their backs against the wall, each of us in a different corner of the small room.

As it inevitably did, the conversation soon turned to sex. Repeating something she'd said in my presence many times over the years, Carlie complained that she was only capable of having an orgasm when she was on top (at least without manual stimulation). This was a constant source of frustration for her, as she considered herself to be far more sexually sophisticated than most girls her age. She'd been sexually active since she was 15 and had amassed an impressively long list of partners. As she usually did when this topic arose, Heather chimed in that she too found it easier to come on top, but that she could come in the missionary position too. In her words, "it just hits the right parts for me." But she added - which was news to me - that recently she'd be able to come pretty regularly while doing it doggie-style (a term she hated). She said that it was just a matter of angling her butt in the right way and that when she'd finally figured it out, it was a "eureka" moment. Upon hearing that, Carlie actually made Heather get onto all fours and demonstrate the right angle. My only real contribution to the discussion was to note that I'd rarely made a girl come in any position other than her on top, at least without using my hand to help. That seemed to make Carlie feel better.

Next the conversation turned to porn. Both Heather and Carlie were curious what I thought of Japanese porn. They'd noticed the two VHS porn tapes sitting near my TV, loaners from one of my neighbors, which I hadn't bothered to hide because I knew these two would be the last two people on earth to be offended by them. I told them it was very hit or miss. Some of it was pretty sexy, but a lot of it was very weird and almost clinical. The Japanese practice of blurring out the genatalia was also very strange.

You would think that watching pretty girls in tank tops graphically discussing sex, and even demonstrating various sexual positions, would get a bit of a rise out of me, get me a little hot under the collar. But it didn't. This was just par for the course with these two and I'd gotten used to it over the years.

From there the subject somehow turned to our own bodies, and Heather mentioned that she and I had seen each other naked on several occasions during the South America trip. Carlie was a bit taken aback by that news. She had been with us only for the first half of that trip, when we were staying in hostels. She missed all of the time we'd spent on the tail end of the trip staying in cheap hotels where we'd often all crashed in the same room.

Carlie liked nothing better than mentally undressing guys and speculating what they'd be like in bed. She did it all the time, in front of me, and given that we'd almost hooked up several times early in our friendship, I'm sure she'd gone through the same mental exercise with me on many an occasion. I think that's why it bugged her that Heather had seen the real thing. Carlie joked - semi-seriously - that it wasn't fair that Heather had gotten to see me naked and she hadn't. I responded that it was fair because Heather, unlike Carlie, had undressed in front of me several times.

Without any hesitation, Carlie fired back: "So if I show you mine, you'll show me yours?"

Though she had a smile on her face, I could tell she was serious. I had no doubt that if I was willing to whip out my cock, she'd show me her breasts - which I'd always wanted to see. At the same time, I was suddenly very self-conscious. This was a girl who often talked about the cock size of her ex-lovers and had clearly seen enough naked men in her day to be able to grade me along a pretty wide continuum. And I had no doubt that's exactly what she'd do if I showed her. As much as I wanted to see those breasts, part of me wanted to preserve the mystery and not just become another datapoint on her scale.

So I stalled. "This isn't really a fair exchange," I said, "your parts don't change. They're always the same size, always ready to be displayed. But if I show my flaccid penis, you're not really seeing me at my best. And that'll be the image you'll always have in your head when you see me. It's bad enough that Heather's burdened with that." I grinned as I said it but I was dead serious.

They both laughed at that, but Carlie wasn't so easily deterred. She raised her eyebrow: "So who said it had to be flaccid?"

There was an uncomfortable pause as I struggled to catch up with her implication. "So what are you saying? That I should whip it out and start jerking off?"

"I'm not saying you should do anything. I'm just saying I understand why you'd want to look your best." She looked over at the TV stand, "what if we put on one those pornos for a few minutes? That might do the trick, right?"

Heather spoke up, grinning, "I'd like to watch one of those anyway, even if you don't want to show Carlie your dick."

Still a bit flustered by the turn the conversation had taken, I got up and put in one of the videos. I figured this would at least buy me some time to get my thoughts together. The video I chose was actually a pretty good one, friendly Japanese stewardesses taking turns servicing first class customers on an airplane. It had a high production value and the girls were very attractive. The situations, while totally absurd, were pretty erotic.

While I knew Heather and Carlie were no strangers to pornography, I could tell this was something new to them, and they were soon totally engrossed by it. Our prior conversation was forgotten, at least for the moment. A stewardess on the screen had finished sucking off the businessman in the front row and was now delicately applying a condom. After rolling it on, she matter-of-factly straddled him and they began to fuck, right in front of all the other passengers. Watching Carlie and Heather watch the screen, mesmerized, somehow amplified its effect. And I soon found myself with a raging erection.

We'd been watching the movie for about 15 minutes and I could tell that they were prepared to let Carlie's early proposition drop, probably having sensed that it made me a little uncomfortable. But the truth was that if we were going to do this exchange, now was the time. My cock was as big as it was ever going to be. And watching the movie had only increased my desire to see Carlie's breasts, finally after all these years. Had I been completely sober, I'm virtually certain that I would not have done what I did next. But I wasn't sober. So I stood up and announced that I was ready.

Heather and Carlie were so engrossed in the movie that it took them a few moments to understand what I was saying. But when it finally registered, Carlie smiled and said "Okay then, you go first. Show me your cock."

I took a deep breath, steeled my nerves, and then pulled my shorts and boxers down to my knees in one motion. My cock sprang out of its confinement, and, to my satisfaction, stood rigid at a 45 degree angle from my stomach. I don't think my cock is anything more than average sized, but by my standards, this was as good as an erection got.

Seeing an erect cock in such close quarters caused a momentary gasp from both Heather and Carlie, who were already pretty hot under the collar from watching the movie. As I stood there, stroking my cock gently to make sure it stayed hard, I spoke: "Alright, your turn, Carlie."

Carlie just sat there staring at my cock, clearly struggling to fully process the situation. But after a moment, what I had said finally registered and she got to her knees. She slowly lifted her tank top above her breasts, without taking it all the way off. Her massive breasts were practically bursting out of her white silk bra. She then reached behind her back and undid the clasp, which caused the bra to fly off her chest like a rubber band.

And there they were, in all of their glory. The two most perfect breasts I had ever seen (and have ever seen since). They were huge and round and so clearly natural. They were everything I had imagined them to be.

Now you might think that, having fulfilled my end of the bargain, my instinct would have been to pull my shorts back up and cover up. That would have made sense. But for whatever reason, I just stood there the whole time, continuing to gently stroke my cock as I stared at her breasts. No one said anything for what seemed like minutes, but was probably just 30 seconds or so. Eventually Carlie lowered her tank top back down, but without the bra, the shape of her breasts and nipples were still clearly visible through the cotton shirt. Taking my cue from Carlie, I began reaching down for my shorts.

It was then that Heather - whom I'd practically forgotten was in the room - broke the silence "Jake, I will give you a hundred dollars if you finish off what you are doing. I can tell you're close. Just come. I want to see it."

"Hell yeah," was Carlie's enthusiastic response. "Me too. Count me in for a hundred."

In that moment, between the alcohol and the sheer excitement of it all, my thoughts were a jumble. I did have a strong urge to finish what I'd started, but what if it could be more than that? Then something occurred to me and I blurted it out before my filters had time to kick in. "Keep your money," I said, "I'll do it for free if you do it too...if you make yourselves come."

By the look on their faces, that was not the response they were anticipating. But they looked at each other for a few seconds - as if silently conversing - and then looked back at me. Heather spoke first: "You've got a deal." Without even waiting for Carlie to respond, she began unbuttoning her jeans and sliding them off to reveal a pair of baby blue cotton panties.

By the time Carlie finally spoke, Heather already had her pants off. "Okay," she said "but no one touches anyone else. Agreed?"

"Agreed" Heather and I both responded. With that, Carlie began taking off her shorts, revealing red thong panties. In the background, the movie - which had been playing the whole time - had reached a particularly intense scene. A man had a stewardess bent over a seat and was thrusting furiously as she moaned.

The scene had caught all of our attention, and when I looked back across the room, both Heather and Carlie were wearing just their tank tops and panties, sitting with their backs to the wall. Both were stroking themselves through their panties. I let my shorts fall all the way to the floor and stepped out of them. I sat on the edge of my bed and continued to stroke my cock, wondering if I'd ever again be more turned on than I was at that moment.

We continued like this for quite a while. I tried to pace myself, wanting to give the girls time to catch up. Both had increased their own pace significantly. Heather had moved her panties to the side and was stroking her clit directly. Carlie was moving her right arm so fast that the spaghetti strap on her tank top fell off her shoulder and the part of her shirt covering her right breast fell forward, exposing it completely.

That was almost too much for me and I had to throttle back for a moment to keep from coming too soon. Having abandoned all modesty, I reached into my nightstand and pulled out a bottle of lube. I squirted a generous portion onto my hand and then went back to work. The squishing sound it made when I resumed stroking myself was clearly a turn on for the girls, who both let out stifled moans. Those moans seemed to break the silence, and, over the next few minutes, the sounds of the movie were slowly drowned out by the sounds in the room, grunts and moans and gasps coming from all three of us.

Heather in particular was clearly getting very close. She had pulled her tank top up over her breasts and was touching her own nipples with her non-stroking hand. I'd seen her breasts before but not in anything close to this context. They were small, but very sexy, with large nipples. Again, I had to hold back to keep from coming.

Then, abruptly, Heather sat up and removed her panties entirely. Once they were off her legs, she rolled over onto her knees and laid her head down on her pillow, thrusting her hips and ass into the air. I could see her hand between her legs, furiously stroking her pussy, which was now visibly wet. Even today, so many years later, that image of Heather's ass pointed up at me is burned into my mind. I can get an erection just thinking about it.

And in that moment, when it was actually happening, I damn near lost my mind. As I stroked my cock, I looked at her. I could see her face on the pillow, her eyes closed. Then they opened and, for a moment, our eyes locked for the first time since this entire masturbation session began. Whether I interpreted her look correctly, I'm still not sure, but I convinced myself - in that moment that our eyes locked - that we both wanted the same thing.

In that next moment, I did something that surprises me to this day. Without saying a word, I stood up, walked quickly across the room, knelt down behind her, and in one smooth motion drove my cock as far as it would go into Heather's pussy. The simultaneous gasp that came from both Heather and Carlie is difficult to describe. It was equal parts shock and excitement. And it made me freeze, with my cock buried to the hilt inside Heather. I just stood there, on my knees, my hands squeezing each of her ass cheeks, the insanity of what I'd just done only beginning to register.

But that would only last a moment, because Heather finally managed to find her voice. She screamed "Oh god, fuck me, Jake!" And that was all the encouragement I needed. I started thrusting hard, slamming into her ass cheeks with each go. Within seconds, she had completely lost it and started cursing and screaming. "Fuck me." "Harder." "Just like that." She moved her hand away from her pussy and used both hands to brace herself against the wall.

I could hear Carlie over my shoulder, out of breath, still stroking herself furiously. She kept repeating "Oh my god. I can't believe you're fucking. Oh my god." At one point she blurted out "this is the hottest thing I've ever seen."

As Heather and I continued furiously fucking, I could tell she was getting close. Confirming my suspicion, her vocalizations changed. She panted, "Oh my god, I'm gonna come. He's going to make me come." A few seconds later, I felt her spasm on my cock and she screamed: "Oh fuuuucckkkkk!"

That was all I could take. Remembering our original agreement, I pulled out of her at the last second and shot the single biggest load of cum I've ever produced in a series of arcing shots across Heather's back. Apparently the sight of me drenching Heather with cum was what finally put Carlie over the top, because I heard a gasp, followed moments later by Carlie screaming "holy fuuuucck" and then collapsing in a breathless heap. By then Heather had done the same. I rolled onto my ass and then laid down on my back next to Heather, staring at the droplets of sweat and cum dotting her back.