I gave my first blowjob after losing a bet [FM]

I’d loved reading stories on here, so I thought I’d share my own. Sorry if it’s a bit slow, I tend to ramble.

For a little context, I’d known this boy through school and we had fucked around a bit on Snapchat for a few years, but never really talked at all in real life.

Before all of covid happened, I remember that whenever I’d see him around school, I’d get excited; partially because he’s cute and I know he’s got a nice cock, but also because I knew that every time he saw me in real life, he’d hit me up that night to masturbate together on Snap. He’d been asking me to take things from just videos and calls to doing something in real life for a while, but I’d never had the guts to do it, though I really wanted to. The fear of being outed as a slut, despite having been pretty slutty online, was fairly immense.

A few years of turning him down had passed, and every time he proposed it, I’d get really wet and really tempted; there was nothing I wanted more than to see and hold a cock in real life, and to get him off with my hands and mouth.

Thus, I proposed a bet. If I lost, I’d give him a blowjob. I’d kinda known I would probably lose, but the risk of it was kinda fun. And evidently, I lost the bet.

The time between losing the bet and actually sucking him off was kinda awkward and long. Neither of us had a car or were ever home alone, so it took us a while to figure out where and when. He lived on the other side of the city from me. Eventually, one night while we were masturbating together, he asked if I was free, and I just so happened to be, on top of having a decent excuse to leave the house that night, so we both agreed to bike to a high school that was kinda near me, and a bit farther from him. It was around 11pm, so it was quite dark out.

He’d texted me beforehand about the location, and he’d asked if he could finger me.

> I’ll only bike that far if I get to touch your pussy

I’d always turned him down for this for several reasons: I didn’t know him well so I wasn’t sure I wanted to let him touch me, and I’d never been able to get myself off, so that made me a bit nervous about letting him finger me knowing I wouldn’t be able to cum for him anyway. But ultimately, I was too horny to wanna say no, and so it was set.

As I biked there, I was so excited for what was to come, I went the wrong way, twice. It took me much longer than it should’ve to get there, and he was texting me along the way. He had just been jerking off before and was scared he’d cum too fast if I kept going now, so he wanted to touch me first.

Keep in mind, we’d barely ever talked in real life, so it was just a bit awkward when I got there. I’d also never done anything in real life, I’d never even kissed my ex, and I’m pretty sure he was also fairly inexperienced.

It was a bit of a shock seeing him, not that I didn’t expect him to be there, but things feel so abnormally real when it’s always just been over video. We rode into a bit of a secluded corner, got off our bikes, and he pulled me to him, my back to his front, before pulling my top up and grabbing one of my tits as his other hand went down my shorts. I would’ve tried to get waxed or something if I’d known beforehand that we’d be meeting up that night and that he’d ask to touch me, not that I have much hair down there, but I felt a bit self conscious off the bat. Though, it was evident he had probably never touched a girl before. His fingers explored my clit a bit and he was almost kinda struggling to find my pussy. I was moaning for him lightly and breathing heavily by this point, and I took his hand in mine and guided it to my dripping wet pussy. As he touched and teased me, he took my hand and led it down to his hard cock. I could feel how warm and hard he was through his shorts, and to this day, I still touch myself to the thought of his fingers in me while I felt him over his shorts, feeling a cock in my hand for the first time. I’m not sure why I hadn’t expected a hard cock to be so warm, and, well, hard, but it was a really nice feeling to be able to stroke him lightly over his shorts, running my fingers over the tip and back, over and over, as he had his fingers working my g spot. It came as a shock that he was actually pretty good at fingering me, considering how he’d fumbled a bit at first. This feeling of pleasure as well as excitement feeling his cock is something I’ll never forget – I guess that’s what comes with doing something fun for the first time.

We stayed in this position for a bit, but apparently 11pm was still a time that people would go on walks, and so we had to stop, get on our bikes, and move to a different spot when people got near us. It sucked a bit, but I think it added a bit of an excitement factor, knowing it was kinda risky. Either way, I didn’t mind it too much. He fingered me for a bit longer before I turned around and asked if I could suck his cock. I realize now that I never knew what he did with his drenched fingers, but I knelt down on my knees in front of him, he pulled his shorts down for me and his hard cock popped out in my face. I made sure to pull my top down so he could see my tits, since he’d seemed to enjoy seeing and touching them. I’d seen his cock in videos several times before, but seeing and holding it in real life was so different.

He was uncut (my favorite), rock hard, and at least 5 or 6 inches, I’d guess, but I’m not too sure. All I know is that he was enough to make me choke, a lot. I hope that’s something that you can learn from practice, because I really wanted to be able to take all of him in. It kinda became a bit of a cycle, I’d jerk him off a bit, run my fingers over the tip, take him into my mouth, try to take it all in, and choke. I’d keep a couple fingers wrapped around what I couldn’t fit in my mouth, and I’d keep trying to take him deeper in my throat. I could feel him thrusting his hips a bit, fucking my throat, but I’d keep choking and began tearing up. It felt like I was making some really unpleasant choking and gagging noises, so I’d pull off and jerk him in my hands instead. I tried and choked several times, before I ultimately gave up and just used my hands and licked and sucked on the tip every so often. I wish he’d given me more guidance and told me what he wanted more often, since I felt a bit lost and wasn’t sure if I was giving him what he wanted.

At some point, he asked if we could stop so he could finger me again and if he could see my pussy, which I agreed to. I let him pull my shorts down, and he knelt down as he pumped his fingers in and out of my dripping pussy. I wrapped a leg around his shoulder so he could see better, and just let him play with me for a bit. It felt good to know I was probably the first pussy he’s seen and touched.

Eventually I went back to struggling to suck his cock a bit, and then jerking him whilst teasing the tip with my mouth. It didn’t feel like too long before he took my hand in his, helping me to jerk his cock, and went faster. Much faster than I’d been going. Again, wish he’d told me so I could’ve tried for myself, but he was helping me to jerk him off. I’d told him weeks beforehand that I’d let him cum wherever he wanted to, and he chose my mouth, so as he helped me jerk him quickly, I awaited his cum patiently and soon enough, let him put the tip into my mouth and felt his cum on my tongue. Not the most pleasant taste, but I didn’t mind it. I swallowed, and sucked his cock clean one last time before I got up, and that was that.

It probably won’t happen again, but I hope that someday I’ll have a boyfriend who’ll help me get better at sucking cock with some guidance, tips & feedback. I really want to learn how to choke less and be able to get him to cum on my own, without him having to help me get him there.

EDIT: feel free to pm me if you wanna :) i’m always down to talk to new ppl (preferably around my age 18-22) and am open to talk about pretty much anything

Source: reddit.com/r/gonewildstories/comments/hr6xe7/i_gave_my_first_blowjob_after_losing_a_bet_fm