That time I won a prize [MF]

I’ve had a few fairly long term relationships, most with a generally decent sexual component. Just after the break-up with a long term post high school gf (and after an almost unbroken 7 month dry spell that had been preceded by almost daily sexual activity) I was approached by someone in a college class I had. Melissa, physically, was the polar opposite of my ex, with D-cup breasts and a decent ass. She was a little chubby, but that didn’t bother me, as, when in college, I wasn’t the most outgoing person, and the combination of the dry spell and the fact that she approached me led to a frankly not great in any way relationship.

Anyway, the sex was…fairly vanilla, as I was (and presumably still am) more experimental than her and willing to try new things, both in and out of bed. The “kinkiest” thing she would do is ask me to rent some porn from the local video store for us to watch together (damn I’m old). And she would get invested in the story.

She had this thing about blowjobs. She wouldn’t ever finish me off with one, despite demanding that I finish her off with oral (which I’ve never minded, but sometimes reciprocation is nice). She claimed this was the only way she could cum, having never been able to in any other way, despite trying. She really wanted to be able to cum in nearly any position or manner like guys could. I asked her what I would get if I could get her to cum in any other position way (aside from fingering). She replied that she’d let me finish anywhere I wanted. So, I’m the kinda guy who, given a favorable goal, will work towards that goal unrelentingly. The next few weeks, we would study together and then I would go to town, enjoying my work, but getting more and more frustrated as I achieved nothing.

One night though, somehow, the planets aligned and she rode my cock to orgasm. I will never forget the surprised tone in her voice as she said, almost incredulously, “Oh my god, I’m cumming!” This was doubly surprising as I had eaten her out and she had cum about 10-15 minutes before this, and she was not generally multi-orgasmic.

I just smiled at her and said, “Guess I get to choose, huh?” She was confused at first but remembered our bet/deal. I don’t know why she thought I’d forget. She climbed off me and began stroking my cock, and warily asked, “So what do you want?” I was still smiling when I told her, “On your knees and suck my cock, I’ll let you know when I’m close.” Before she could protest, I reminded her she was a woman of her word, and I did just give her something she was craving.

Without another word, she dropped down and began to give me probably the best head she ever had. She stroked my balls, used her tongue and lips, and no teeth (she was just normally not that good at it). My eyes are closed at this point, enjoying the sensation, when I feel a tap on my side. I open my eyes and lock with hers. She reaches her fingers up to my mouth and I knew she wanted me to suck on them. After they were wet enough, she takes them out and starts rubbing her pussy, eventually inserting about 3 fingers inside herself. Seeing this, I get close and let her know to stop.

I tell her to stay on her knees, keep her mouth open and close her eyes, and keep fingering herself. I start to stroke my cock and feel myself getting closer and closer, until with a growl, I explode. Cum goes all over her tongue, her nose, her chin, and even some up her nose. I got her a towel and we both laughed. She said the taste wasn’t bad. I often wonder if anyone who came after me got to do that, as she never let me again.

Comments are always welcome.

Source: reddit.com/r/gonewildstories/comments/hztj2d/that_time_i_won_a_prize_mf