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.