[M]y first [F]WB Made Me Cum in My Boxers, Which Led to Us Competing in Just About Everything Sexually

Please bear with me, as I don’t think I’m the most descriptive or eloquent story-teller around. But this is one of my favorite sexual memories, and a go-to during alone time… so I thought I’d share!

To set the stage, I’m Tyler. Currently 31, but an 18yo high school senior at this point. I was a late bloomer; a bit chubby until I grew into my height (6’2), and then became pretty tall and lanky. My cock is slightly above average size-wise (6.5 to 7″ if I’m really feeling it!), though I had no idea at the time that I was above average. I played baseball and was in decent shape, though the years of social awkwardness and not seeing myself as attractive had left me pretty unexperienced; I had kissed a girl, but never gotten past first base at this point. Until I started talking to Haley.

Haley was also an 18yo senior at the time, and on the soccer team. And I had always thought she was way, way, way out of my league. Short, but very fit, small breasts and a toned ass; long blonde hair, and very fair skin.

I’ll skip a lot of the initial flirting and such. We started chatting after our respective practices, when everyone was hanging out in the parking lot before heading home. It took me longer than I’d like to admit to realize she was into me; but eventually, I got the hint and we made plans to meet up at my parents house while they were away.

Soon enough, the day arrived, and I excited let her in. We chatted for a little bit, flirting and exchanging stories on the couch, slowly sliding closer and closer together, until our hands started to touch. If this sounds like a stereotypical inexperienced high school guy trying to make a move, you’re exactly right. I had debated how best to initiate, and ultimately chickened out of most of them. Thankfully, Haley was a bit more experienced than I was at the time and recognized my hesitation, moving her hand to my leg and ever so slowly up.

Even someone as oblivious as I was couldn’t miss that signal, and I leaned over and kissed her… the 2nd girl I’d ever kissed. I imagine it was quite sloppy, and messy, but she seemed to really enjoy it. And I was definitely quite into it. We kissed for a while, although it was probably only about 5-10 minutes, before I felt her working my shirt up over my head. I allowed her to take it off of me before returning the favor, lifting her shirt over her head to admire her breasts behind the bra.

We went back to kissing each other, though she again took the initiative and climbed on top of my lap while we were sitting on my parents couch. If I wasn’t hard before this, I was now… and I’m sure she could feel it. I probably should mention that I was wearing some lightweight basketball shorts and boxers, and I’m sure my bulge was very apparent. I kissed her while my hands explored her body, and clumsily fumbled at her bra clasp… which took me quite a while to unhook.

I’m not going to lie… I’d seen quite a bit of porn by this time in my life, so seeing a naked girl wasn’t a shock. But seeing a naked girl in person, watching that bra fall away, and being able to put my hands on her chest for the first time… those are memories you just don’t forget. And did I ever start playing with them, kissing her while massaging her nipples, kissing down her neck to suck on them… I was in heaven.

Now while all of this was going on, she was still on top of me, grinding her hips away on my lap, my cock trapped in my boxers. And as distracted as I was to play with her tits, I didn’t quite realize just how much friction there was between her ass and my cock, pushing me ever closer to that edge, until that familiar sensation of an impending orgasm approached.

When I realized what was happening, I did try to push her away. My hands on her hips, trying to pull her up. But I didn’t tell her what was about to happen, so she stayed put, continuing to kiss at my and dry hump away… and then it was too late. When I knew I couldn’t get away, I distinctly remember putting my head into her chest, and letting out a little moan into her tits… as my cock began to spasm and twitch in my shorts. I tried to hide it, but there was no way that she didn’t feel my cock twitching; thankfully there wasn’t too much of a wet spot as I was still in my shorts, though my boxers were drenched.

She stopped grinding and looked down, trying to judge what had happened… and I started apologizing profusely. My first time with a girl in-person, and I literally blew it. Thankfully, she was amazing about it. She smiled, not in a disappointing or mocking way, and reassured me. Told me how much of a compliment it was, and that she enjoyed herself. I’ll admit, I should have offered to get her off as well, but in my inexperience and embarrassment, we ended things there and got dressed, hung out and chatted for a bit more, before she left.

After she left, I honestly thought that would probably be the end of it. Who would want to hook up with a guy who can’t even hold it long enough to get out of his boxers? But to my surprise, we continued to chat afterwards, and she admitted that it actually really turned her on to get me so excited that I couldn’t hold it. Perhaps from years of playing sports, she told me that she’s super competitive and almost felt like she “won” our hookup… which to be fair, she totally did. And most surprising of all, she wanted to continue hooking up like that. With a little competitive edge to it.

I’ll probably stop here for now, but would be happy to share some more stories with Haley if there is interest. From there, we started hooking up pretty regularly and maintained an on-again-off-again FWB relationship for several years, when either of us weren’t dating someone else. Primarily, our dynamic involved little sexual competitions; trying to get the other person off first, seeing who could accomplish various sexual goals, trying to distract the other person with sex. I’ve never had another partner who was so eager, or enjoyed making me cum in my boxers, as Haley.

Source: reddit.com/r/gonewildstories/comments/nh63ic/my_first_fwb_made_me_cum_in_my_boxers_which_led