I’ve gotten a handful of requests to continue this story, so I’m happy to share the next part of my premature adventures with Haley. As I mentioned in [my last post](https://www.reddit.com/r/gonewildstories/comments/nq3two/my_first_fwb_made_me_cum_in_my_boxers_pt_3_how/), Haley and I began dating other people off and on after those initial set of stories, so our meet-ups became less frequent. However, when we were both single at the same time, we inevitably started hanging out and hooking up again, and this next part takes place during that period when we were in between partners.
As always, to recap who I and Haley are, 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. As described in my previous posts, we had started to hook up… and she had a way of making me absolutely lose control with her. The first time ended up with a mess in my boxers, and the second time was a competition that was about as one-sided as competitions can get.
So, Haley and I are both in college now, probably around 20-21. I had been single for a while, only had one serious girlfriend prior to this part of my life. And Haley had very recently gotten out of a relationship with some guy that she had been working with. I didn’t know much about him, but after she broke up and we began hanging out again, I learned a lot more about him.
His name was Carl, and he was a bartender at the restaurant she was a waitress at. He was a biker, and I remember Haley mentioning that she really enjoyed when he took her out on the bike. Otherwise… it sounded like he was an ass. She told me that he never did stuff she wanted to do, and didn’t make time for her, and still flirted with other customers and waitresses at their work. Ultimately, she had enough and called things off with him. Within a couple of weeks, we were hanging out again and she was giving me handjobs and the occasional blowjob to make me cum quickly again. I was pretty glad to have Carl out of the way!
So, one day a few weeks after we started hooking up again, Haley came over and we started chilling in my room, talking and snuggling on the bed. We started kissing, hands exploring each other… when she gets a text. She stops and leans over to check it, which wasn’t totally abnormal as we hadn’t really gotten into too much yet. But then, she pulls away from me and gets out of bed to start getting dressed.
I ask her what’s wrong, wondering if I did something or if everything is okay. She starts telling me that something came up and that she has to go, apologizing the whole time. Of course, I’m concerned but don’t try to stop her, telling her it’s totally okay and that she needs to take care of whatever she needs to. And, just like that, she gets dressed and leaves.
I send her a text an hour or so later, telling her I hope everything is okay and to let me know if she needs anything. She responds a bit later, telling me that it was all fine, no need to worry, and asks to come back over to my place. I quickly agree, and within the hour she’s back over, and we’re back in my room.
I didn’t want to be too nosy and ask for details, but thankfully she initiates the conversation and apologizes again for leaving earlier. She goes on to tell me that the text she received was from her ex, Carl, asking her to come over… for a booty call. And that as she was getting turned on from our foreplay, she really, really felt like she needed to get fucked.
She hadn’t told me much about this side of her relationship before, but I suppose in order to justify herself, she started to tell me a bit more about why she needed to get fucked by Carl in that moment. As bad as their relationship might have been, the sex between them was supposedly incredible. He was hung, had great stamina, and pushed all her buttons. A tale as old as time, she stuck it out with that relationship because of the sex for way too long, and was having trouble not going back to him because of it.
Truthfully, I was pretty shocked to hear all of this. Leaving me in the middle of us making out and getting into it to go get fucked by another guy? I didn’t really know how to react. And looking back on it, I wondered if Haley was testing me somewhat, seeing how I would react. I could’ve been angry, telling her it wasn’t cool to leave me like that. I could’ve asked her to leave. But if I was being honest with myself, hearing her talk about getting fucked, something I had still not done with her, simply got me imagining her naked, bent over, moaning out on a big cock… and I just told her it was okay. I didn’t mind.
The relief on her face was palpable, and she gave me another one of those coy, sexy smiles that I just couldn’t resist. She thanked me up and down, was glad that I wasn’t mad… and then told me she wanted to make it up to me. She leaned in and kissed me, a deep and passionate kiss. For the briefest of moments, I remember thinking that she had just been with Carl, probably kissing him… and perhaps doing lots more with her mouth… before I just started to kiss her back. Not thinking about it, just enjoying it.
And she definitely did make it up to me. After kissing for a few minutes, she slid my pants off and got on her knees at the edge of my bed, taking my cock in her mouth and working it expertly. As always, within a minute or two I was struggling to hold back, and she swallowed every drop I had before we resumed our kissing and cuddling on my bed while we watched something on TV.
After she learned that I was mostly okay with her fucking Carl still, it started to become a somewhat regular thing. We would chat for a bit, she’d mention that Carl had fucked her really good earlier, and then we’d resume our normal activities of all foreplay stuff. She didn’t rub it in my face like you might see in porn. She didn’t tell me that he came in her, or talk about him while we were having our fun. But in the back of my mind, I definitely thought about it. When we kissed, had she been sucking Carl’s cock a few hours before this? When I ate her out… had he cum in her? And there was the always-present dynamic that Carl was getting to fuck her over and over again, while Haley still was making me cum hard in her hands or mouth, but never letting me fuck her.
And if I’m being honest with myself, I enjoyed that dynamic. The power differential made things a little hotter, and I definitely came more than once while thinking about Haley getting fucked by him. It never progressed to a “true” cuckold scenario where I was present, or it became a part of our fantasy play or anything. But it definitely felt like another man was clearly taking charge and fucking the woman I was with, and definitely got me intrigued in that kind of stuff.
PMs and chats are always open if you’d like to hear more, or have any questions or would like to chat about any of these experiences! Thanks again for reading =)
Source: reddit.com/r/gonewildstories/comments/o3f3rf/my_first_fwb_made_me_cum_in_my_boxers_pt_4_i
She sounds terrible tbh, but to each their own.