During my last few months of college, I hung out with a fellow student and neighbor from a few houses down. Her name was Mary, and we met earlier that year and hit it off as very good friends, and despite both our perpetually single statuses, never managed to get tangled romantically. Sexually, however, it was a different score.
On a typical Friday night after classes, we had gone to a nearby mall and done some shopping, her mainly for clothes, and myself because I had nothing better to do. Somehow she managed to convince me to buy a couple new pairs of jeans.
We got home and during the evening we started talking about things sexual. The topics intertwined, and again, about half an hour later, we began discussing masturbation, when I proclaimed my 'undying love for jacking off,' and how I liked to masturbate at least once or twice a day. She laughed, but admitted she did as well, but not as often as I did. Then we talked of other topics again, but I was aroused enough at this point that it wasn't going to go away all on its own.
About an hour later, now a solid three hours into our conversations, Mary asked me to model my new jeans. At this point, things get a little hazy to recollect. I know I retreated to my bedroom to change, and came back into the living room with all my clothes on. I think I then went back into my bedroom, and removed all my clothes, and then put just the jeans on, sans underwear. I came back in and mumbled something about how this was much more comfortable; I sure felt warm! Mary gave me a look that said, yeah, whatever. I think I then made mention that actually, I was so hot, I should take my pants off too. Mary watched me in amusement as they fell to the floor, and I stood there totally nude. What, no underwear? She asked me.
No, I told her. I explained our talk earlier had made me horny and when I'm horny, I like to be nude. I think I then tried to convince her that she should be nude as well. Mary seemed a bit more reluctant than I was, but she did mention how she felt content for me to remain that way and she actually was enjoying looking at me nude. Then she peered over at me in a very obvious manner, looking especially over my penis and genital area.
Did you shave yourself? She asked me. I had. Why? I explained to her that I liked the feel, and it was a big turn-on when I have my masturbation sessions.
Well, she said, you certainly take your jacking off seriously. Even as she said that, she continued to look at my penis. Now that she was watching it, I started to get hard.
I asked Mary again if she would like to undress, but she again politely declined. I told her I was very horny and had to jack off NOW. She started to get a little annoyed, and told me to put some clothes on. She certainly looked a bit more uncomfortable now, and I tried to convince her that it would be really 'hot' If we each masturbated ourselves while watching the other.
She said probably another time, but not tonight sweetie.
Somehow, as I was pleading with her to touch herself, or at the very least take some of her clothes off, my hand slid downward along its familiar route, and grasped my now full erection. It was so without thought, I didn't realize I was actually jacking myself off until I saw Mary's face turn into this horrified look. I glanced down and saw my hand moving up and down my penis. It was surreal, I didn't realize I was actually getting myself off until I saw gobs of my cum flying up in the air, and then, at least FIVE seconds later, I felt the overwhelming convulsions and contractions of an orgasm. I sat back down on the floor. It was probably a 12 on a scale of 1 to 10 orgasm. Mary left quickly and quietly, saying she would call me the next day.
I felt terrible the next day, due to what I had done to Mary. I called her, which still wasn't until two or three the next afternoon, and I apologized to her profusely. Mary was actually very gracious, and later explained she felt bad for getting so upset and she realized I was very very horny and she didn't do enough to stop me sooner. I told her it was still all my fault and continued to offer my apologies and I'm sorrys for nearly two more days.
Finally, she was over at my place again the next week. Things were somewhat back to normal between us and she confessed to me that she had been extremely turned on a couple days later when she really thought about it, and had masturbated on her own, reliving the scene in her mind of my engorged penis spewing semen straight up in front of me. In fact, every time we were together alone again, she would bring that up. Finally, about three weeks later, she asked me if I would jack off for her again, she wanted to watch. I agreed, and we went into my bedroom, where I again stripped for her. She thanked me when I was done and promised someday she would 'return the favor.'
She did. And then some!