She Sends Pictures

Sherry was my girlfriend senior year of high school. She is a slender blonde with long legs and a fantastic derriere; her breasts are fine, but kind of small. What makes Sherry irresistible is her large, soft eyes. She looked sweet and innocent even when she looked over her shoulder to watch me fuck her.

We ended up going to different colleges, and her subsequent adventure is what I want to tell you about. We decided at first that we would stay together as long as possible—totally monogamous. I didn't have too much trouble with that, since I didn't meet anyone like her at my school. But as the months rolled by, it got harder and harder for us to be happy with the situation. We visited a few times, but it was expensive. I told her how horny I was without her, and she said it was hard for her too.

Finally, in February of freshman year, I ended up having sex with a girl in my dorm. It was very casual and only so-so, but I had to confess right away to Sherry because I felt bad. She was a lot less disappointed than I expected. She ended up saying that maybe it was time to start a new phase in our relationship, that maybe we could start dating other people even though we would get back together in the summer. I was reluctant, but in the end I said ok. I hadn't really thought what it would be like for me if Sherry had sex with another guy, but the more I thought about it, the more exciting it sounded. About a week later, Sherry sent me an email, saying that she had met a guy the night before and would probably have sex with him in the next day or two. "I don't know...are you ok with this? Well, you do owe me one. I'll just see how it goes."

That night I beat myself off three times, thinking about Sherry going down on another guy, getting rammed from behind, and so forth. The next morning, she sounded tired and a little giddy. "I'm really sore! We did it three times, and I have to say it was fun. Derek is, you know, kind of a big guy, and I don't just mean his muscles." I found this incredibly arousing, even though she was openly teasing me about being with a guy whose dick was bigger than mine. I asked her to tell me more. She told me that she gave him head, that she was on top for the first twenty minutes, and that the rest of the time he fucked her doggy style and missionary—just as I had fantasized. I told her not to get too carried away with this guy, and she said she wouldn't. "I hardly know him, after all. He's very nice and courteous. He wants to take me out to dinner." I told her not to get too emotionally involved, because I still wanted to be together at the end of all this. She said she wanted that too and that she loved me.

Over the next several days and weeks, Sherry had sex with Derek almost every day. She only told me about it when I asked, which I began to do with more frequency and urgency. The whole thing took over my thoughts, as I imagined all the things she did with him, and what she must have looked like riding on his big cock. I wasn't able to keep my obsession from her very well, and soon she began sending me emails from the library about this or that detail of her adventures.

Then one day I got a photograph in my inbox. It was a picture of Sherry, naked, standing over a desk and looking over her shoulder with a "come fuck me" look on her face. This was getting to be too much. I wacked off again and again looking at that picture, enjoying how sexy she looked and imagining what must have happened next.

I begged for more photographs. A couple days later, things got crazier. I opened up a picture in my inbox of Sherry sucking on Derek's cock—damn that thing was big! Her entire grip barely fit around his shaft, and she stared at me with those puppy dog eyes and her lips pursed around the top of his cock head. There was another photo with her trying to swallow him—her eyes were closed, but there was effort and passion on her face. In the next one, she was eye to eye with his massive tool, a tie of semen connecting him to her lips. Just to have fun with me, she had on a cowgirl hat even though she was totally nude otherwise. Finally, I got a picture of her bending over in the other direction. He was obviously fucking her doggy style while taking the photo, but he didn't have the best angle for the shot.

Finally, I asked Sherry if she would be willing to videotape herself with Derek. At first she said no way, and I dropped it. Then, a week later, she told me that her friend Hannah had got hold of a video camera, and that they were going to make a movie after all. I knew from hearsay that Hannah was wild and liked this sort of thing.

So the video finally arrived. Yet again, I was overwhelmed by shock and lust at what I saw, even more so than from the pictures and stories. Sherry had a look of bliss on her face has she rode up and down on his cock, slowly and with great emotion for about ten minutes. She was much more vocal than she had ever been with me. This was a different Sherry. Then they got into doggy style, and the action went faster and harder. For a while, she let out short, soft moans with each of his thrusts, but then she started building towards orgasm, and he responded with more and more energy. It started to look like he was banging her hard enough to hurt, but I guess she had stretched to meet his dimensions. Just to make it fun, Sherry blurted out that she wanted him to come on her face like a porn star, which he got a thrill from doing. The whole thing had me wiped out for days.

Sherry and I stayed together until the summer, but she ended up messing around with some other hung dude from our high school. We parted ways, sadly—it was the most erotic experience I never had.