I was taking a trip across the country, and I needed a place to crash halfway to my eventual destination of Des Moines. There was a girl I knew a little, Shannon, who lived in Indiana, and I was hoping to stop at her place. I had only met her once, at a friend's summer place on a lake for one week. She had come along with yet another friend of mine, Tom. Tom had basically had a crush on her for his whole teenage years, but now that we were well into our 20s, it was clear to everyone but him that that was not going to happen, they were stuck in friendship mode. In any case, I had gotten along well with Shannon, and she had offered to let me stop by when I had mentioned my trip to her that week on the lake. But now that the time was actually approaching, I was nervous. I was never the most forward person about asking anyone for a favor, and was definitely at my least comfortable when it came to girls. I wasn't a virgin, but I was not exactly the most experienced guy in the world.
Shannon was cute, hot—not supermodel hot by any means, but when you're a normal guy, and you see a chick in a bathing suit for a week, you get to lusting after her no matter what. And she did have the looks to back up that lust no matter what the circumstances. She was short, maybe 5'4", a cute round face with big dark eyes, sweet full lips, and nice cheekbones. She had shoulder-length brown hair, a nice round, tight ass that packed her worn-out jeans well, and was in good shape—not skinny, but no extra weight, and perhaps most prominently, she had the feature that probably should have been first on this list: a fantastic rack, a heavy set of D-cup knockers that weighed down nicely on her chest, not saggy, just big and real and round. Her nipples were the object of my constant attention during our week on the lake—they were pretty long and stood out proudly through her swim suits, even though she wore somewhat conservative one-pieces. A one-piece is still pretty fucking hot if worn by the right girl in the right way, and I had spent half the week with a woody in the water, watching her tits bounce up and down, her ass saunter back and forth, and we all played and talked on the beach.
Yes, she was clearly the kind of chick that I was perfectly happy to jerk off about for weeks afterward. Asking if I could stay with her, however, was intimidating, even if she had already invited me, especially since there was the somewhat forbidden aspect of the whole situation, since my friend Tom was still secretly in love with her. It made me even a little guilty just to jerk off about her.
But I did need a place to stay, and even if I was a pussy and knew I would never actually hit on her, I also couldn't stand it if I didn't at least put in the minimal effort of talking to her again, so I called her up. She was totally glad to hear from me, perky even, and we set it up. I jerked off again just anticipating seeing her, knowing that was going to be as close as I would get.
I drove in a few days later, and knocked on the door of her apartment. She opened the door, and immediately I had a stiffy. She wasn't dressed in an obviously hot way, just a tight grey t-shirt and jeans, but that t-shirt was clearly showing off her best assets in a way that made it hard for me not to stare. She gave me a hug and was really friendly, touching my arm a number of times. She really seemed glad I came. We went out to dinner, and I was feeling like maybe something might happen after all, against all odds, at which point she dropped the info that killed off any of my anticipations: she had a boyfriend. He was away for the weekend, he wouldn't be back until tomorrow after I left, and he was sorry we couldn't hang out. Well, fuck, that sunk it. But we still had a nice dinner, and then went to a movie. We walked around a bit and she showed me the college town, and eventually I started to wonder again. What was the deal here? She kept looking at me in the eyes, kept touching me lightly. I'm no expert, in fact I'm a body-language idiot, but it seemed to me that she was sending signals.
When we eventually got back to her room, it was pretty late, so we got ready for bed. She dressed in a threadbare white t-shirt that hung just slightly below her crotch. The view of her long nipples brushing against that shirt, tits swinging around freely without the confines of a bra, gave me enough material for weeks more of jerk-off sessions. I was in a t-shirt and boxers. She got in bed, and I made as if to lay on the couch, but she suddenly said, wait, that couch is really uncomfortable, it's got loose springs, just come in the bed, there's no harm done, I've got a boyfriend, right?
What the hell. What was I supposed to do here? My cock clearly told me that I was supposed to jump up immediately and get in bed. However, my ethical side told me that I was possibly screwing over my friend Tom, not to mention her boyfriend Justin. And really, was my mind just playing with me? What if I got in bed and nothing happened, but I couldn't hide my hard-on, and it became obvious, would she kick me out? I was in a land of mixed signals from her, and mixed motives from my own brain. I said the couch would be fine. But she insisted, and after a few more back and forths, I got in bed with her.
I laid down, and she did too, facing each other, and we talked a bit. I had to put an enormous effort into not coming in my shorts right there. But after her big moves earlier, she seemed to change course yet again, and eventually we dropped off to sleep, with me turned around facing the side of the bed so as not to let her see my engorged cock.
A little later in the night, however, I felt some kind of soft crawling touch, and slowly re-entered the world of consciousness. A hand was slowly making its way across my side, slowly moving across my front, slowly making its way down to my hips, slowy—going inside my boxers! Her small hand lightly caressed my cock, feeling its column of flesh, touching my balls, and it was impossible for it to remain unresponsive. It slowly started to grow under her ministrations, and enlarged to its full size within a minute. Oh my god, I felt so goddamn good.