[MF] The Bet

This is my first time recollecting a real sexual experience in writing, but I thought I’d give it a shot, I’ve got a fair few stories. **[I just noticed that I wrote quite a long-winded intro, will indicate when the naughty bits start.]**

This took place when I was a student, 21 at the time. I used to go to this small bar four nights a week, became good friends with the regulars which were all in their twenties or thirties. It was a really nice place to be at, not the most popular, but the prices were decent and the owner would let us stay after closing time to play pool for free.

Most of the people there were quite sex positive, and some of them had had some fun together on occasions. It wasn’t rare for everyone to notice when a regular picked up someone, and then became a less frequent visitor for a while as they’d better things to do at night. In a way, I was the odd one out on that front, and there was some friendly ribbing about it. I’ve never been shy about physical touch, so it wasn’t rare to find me cozying up to someone, but I never made a move.

Truth is, I’d only slept with people I was dating for a while, never really felt like a one-night stand kind of guy. I was also a bit oblivious at the time, and often thought of flirty behavior as friendliness. I’ve had women invite me to their place for “one last drink” and not catch their drift at all.

Naturally, with this kind of “good boy” image I had amongst the regulars, it made a bit of a wave when I finally did have a one-night stand. It happened with the roommate of one of the regulars I’d made friends with, not someone who frequented the bar. Simply the most attractive woman I’d been with at the time, still one of the most attractive to this day, which is pretty much why it happened. I don’t think I figured out she wanted to slip with me until she started taking off her clothes, but this is not the encounter this post is about.

So I had a lovely time with this woman, and with classes and projects, and lack of sleep, it takes me a few days to finally get back to the bar. When I finally find my way back, I can see most of the regulars just grinning at me, the owner pours down a drink and says there’s a few more coming my way. One of the regulars I get the most along with just sits down next to me, slaps my back, and says, “My condolences.” I just stare at him without understanding at first.

The thing is, I’m a hard man to please, quite literally. For some reason, it’s always taken me ages to finish. So while my partner had a few orgasm, I had a whole total of zero of them. Which was quite frustrating at the time, but I’ve come to be more acceptant of since then. Anyway, not exactly something I was shouting from the rooftop. Except the lady in question loves to talk about her sex life to her roommate, who happens to love whiskey a bit too much.

With me not being too comfortable talking about sex in public, it became a bit of a recurring joke to make flattering comments about my abilities. Stuff like telling women, “he doesn’t look it, but it’ll keep you up all night.” Or, “he’s champion of the bedroom marathon.” Just overall good-hearted things that made me blush like a five year-old and gave everyone a good laugh.

**[Naughty bits are about to start here.]**

Everything goes back to normal, until one night, a young lady who’s feeling particularly frisky starts making claims about her oral prowess. The regulars who like to have a bit of banter with the students that come through start telling her to pipe down in a playful manner. Saying things like, “If you were so good at it, you’d be too busy to be here on your own.” Stuff that must have struck a nerve, because she became even more adamant about it.

Worst of all, the lady is here with her friends, and one of them decides to have her back. So you have two young women just arguing with a bunch of patrons about how good one of them is at sucking cock. Which leads to a fateful hand coming to slap my back. “Are you ready to bet on it?” my dear friend asks them.

The braggard immediately says yes, her friend seems a bit more cautious about it. So he says, “If you can make this guy cum with your mouth in under fifteen minutes, I’ll buy you a bottle. If you don’t, you’re paying for my next drink!” Like an idiot, I get a big smile on my face. Good one, right? Just a bit of an inside joke. Nothing like that would ever happen, that’s just ridiculous.

“Okay,” says the girl’s friend. “If we win, we get a bottle of tequila.” The guy slaps his wallet on the bar. “Ready when you are.” I’m still smiling at that point. Then the girl swallows her drink in one gulp and gets up. Smile starts to falter a bit. Her friend joins her. I’m feeling a bit wobbly. The regular asks the owner for a key to the backroom. I’m slightly panicking.

I went into that backroom telling myself this was a prank. I was about to crack a joke when the self-proclaimed fellatio virtuoso suddenly grabbed my pants. Her friend points an accusing finger at me, and tells me to keep my hands to myself. I get the sense that she joined to make sure her friend is safe, which I think is sweet until I hear my zipper coming down and there’s a sudden breeze around my thighs.

This sudden, strange situation was a bit uncomfortable, but I was still half-hard by then. I’ve got to say, the intense look I was getting from her friend did as much to get me fully erect as her tongue did. Maybe it was because I found her more attractive, I don’t know? She was a petite brunette with light-brown eyes and freckles. I remember thinking I wanted to kiss her, turn that suspicious look into something more friendly. I think she saw it, because she looked away and just stood beside us while her friend was going down on me.

I don’t know if I can speak much about her technique, but her enthusiasm was definitely there. This was a woman who definitely took pride in her hobby. She was fondling my balls with a gentle hand while bobbing her head on the tip of my cock. I wanted her to take it deeper though, but I was too dumbstruck to make any suggestion, and I’d been clearly told not to touch a hair on her head. I was definitely turned on by the way she was going at it, eager to make me cum, I didn’t care much that this was a bet.

A bet she couldn’t win, of course. I’ve had only two women in my life who could make me cum with their mouth, and never as the first thing we did. Oh, seeing her work the shaft while she sucked on the tip of my cock was fascinating, and definitely made me hard, but she didn’t have a chance. I think she realized it when she looked up at me, probably to see if I was close, and realize I was as cool, calm, and collected as if I’d been doing homework.

“Shit,” she sighed, still stroking my cock – out of habit probably. Then, to me, “You don’t like that?” she said. And she smiled at me for the first time that evening. It really lit up her face, and with my cock right next to it too. She opened her mouth wide, and slapped my cock against her tongue. “You know I want it, right? I love it. You can even cum on my face if you want.”

That made me smile too. Both because there was no way I’d finish that fast and she had no idea, and because I really wanted to cum on someone’s face like I’d seen in porn but I’d never done it. Made me wish I could have cum right then and there, so I guess she knew what she was doing. She started sucking me again and I just watched her, imagining myself grabbing her hair to cum on her face eventually. Trying to convince myself that she’d love it. That she was waiting for it. I thought that was the hottest thing she could do.

But then, she lifted her hand, and snapped. That took me by surprise, I even wondered if she thought that was some kink I didn’t know about. But what she was really trying to do was getting her friend’s attention. What followed still blows my mind to this day. She nodded, my cock still in her mouth, and pointed down next to her.

Her friend looked shocked at first, she’d been looking at her phone for a few minutes now. Then she looked at me, then at my cock. Fuck… I can still remember her eyes fixed on my cock as she stepped closer and got on her knees. I don’t even want to think about the kind of dumb expression that must have been on my face then.

She was short, shorter than her friend, but much, much shorter than me. Her mouth was small enough that my cock was a tight fit even when she opened wide. I still didn’t have an orgasm, but I damn near had a heart attack from the sheer arousal. It didn’t last long after that. Someone knocked on the door, shouting, “time is up”. I barely had time to put my pants back on before they stepped out.

I can’t remember for sure, but I think they never paid for my friend’s drink, although he still thanked me for it. I locked eyes with the braggard’s friend a couple of times after that, that night, and each time it made my trousers feel a little tighter, but I never had the balls to go ask for her number.

They never came back to that bar which in all honesty, I was glad about, because that would have been quite awkward.

Source: reddit.com/r/gonewildstories/comments/10g38vm/mf_the_bet