She bet me a blowjob, and lost. She was too scared to do it so her friend sucked me instead.

I met a girl on some chat site years ago, and we chatted for a while before ever deciding to meet up. I was 22M, she was 18F. We’d exchanged plenty of dirty pics of ourselves before ever meeting up, and we’d talked about potentially hooking up, but it was mostly just fun and hanging out once we met up.

So this girl (let’s call her Stephanie) always brought her friend (also 18F) with her when she came to hang with me and my friends. Stephanie was a little overweight and kind of cute. Her friend Ashley was not as cute, but she had an absolutely smashing body. Not thin, but thinner than Stephanie, and she still had some nice curves, a great ass, and the most magnificent set of tits.

Ashley and I kind of hit it off pretty well and we’d flirt a lot and there was definitely some sexual energy. I feel bad now looking back because Stephanie obviously was interested and I just kind of moved onto the hotter friend. But we all hung out together pretty often and had a good time.

One night we were all bowling, pretty big group of guys and gals mixed. Ashley and I were making silly little bets throughout the games, and being playfully competitive. Finally, we end up making a bet that if I beat her in the next game, she would go outside and suck my dick. (I honestly don’t remember what the bet was had she beaten me, but it doesn’t matter because it didn’t happen lol). I beat her that game of course, so I was pretty ramped up about getting head from this girl.

Turns out she’s a virgin and she’s never even sucked dick before lol. So she’s nervous. Stephanie is encouraging her to just go do it. My friends are egging her on to do it too of course. I could tell she wanted to but she was just too scared. So Stephanie finally says, “if you won’t do it, I’m going to”. I agreed that if she did it, it’d satisfy the bet for Ashley. So out the door we go!

Once outside we walked around the corner from the door to the bowling alley and down a little pathway where it’s pretty deserted, nobody really around. She spotted a bench and she told me to pull my shorts down and sit on the bench. I’m pretty sure my shorts were around my ankles and I was sitting down before she even finished the sentence. She sat next to me and started to stroke my cock. I grew pretty quickly in her hand. Then she tells me that she’s never done this before either, but she’ll give it her best shot.

She moves herself to lay across the bench and she proceeds to take my dick into her mouth. She barely had my head all the way into her mouth and she started to bob up and down on just the head. No tongue, no suction, definitely a very amateur blowjob. But a bad blowjob is better than no blowjob so I was still trying to get into it. I’m very thick and she was not able to get much more than just the head into her mouth and her bobbing was not doing much for me. I started giving her guidance while she struggled, telling her to just try to go a little further, or to use a little tongue and suction on my dick head, stuff like that.

Give the girl credit, she definitely was trying, but she was not doing a good job at all. There was no way this was going to make me cum. So to save her the embarrassment (and to get my nut off lol) I told her to kneel down on her knees so I could stand in front of her. I put the head of my cock back into her mouth and let her go back to attempting to suck me off. I started to stroke my cock into her mouth while she sucked the head. My stroking felt good and the view was nice seeing my dick in this girls mouth so I knew I’d be able to cum this way.

I put one hand on back of her head but didn’t push her down onto me, just kind of guiding her movements to be in tune with my strokes. I told her I was getting close to cumming. I wasn’t sure if I should even cum in her mouth or what that would be like. But when I said I was close, she looked up at me, and it was so fucking hot. Her eyes were a mix of fear, excitement, and the unknown. Tip of my dick between her lips and me still stroking my shaft, I felt my load cumming.

I told her to stay just like that and keep looking up at me while I cum in her mouth. I started to flood her mouth with cum (I cum a lot and it shoots out really hard). The first one or two shots went into her mouth, but it apparently caught her off guard and she pulled back off my cock. The last 3-4 shots of cum hit her in the face, in her hair, and on her shirt.

We put my dick away, cleaned her up a bit, and we went back inside with our friends. Ashley didn’t believe she really did it, but Stephanie had the cum splatter on her shirt to prove it lol. Wasn’t a great blowjob by any stretch of the imagination, but I’m sure it’s a great story for her to remember the first time she sucked a dick lol. And obviously I still like to talk about it!