[M]y First [F]WB Made Me Cum in My Boxers, Pt 4: I Think I Got Cucked?

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.

[M]y first [F]WB Made Me Cum in My Boxers, Pt. 3: How Many Pairs of Boxers Can She Ruin in One Day?

Once again, thank you all for your response to the previous stories of my quick, fun times with Haley. I’ve really enjoyed all of your comments, DMs/chats, and even awards (!!!). Sorry for the delay in posting these, I want to take my time writing them up! For those who have missed previous ones, you can find [Part One here](https://www.reddit.com/r/gonewildstories/comments/nh63ic/my_first_fwb_made_me_cum_in_my_boxers_which_led/) and [Part Two here](http://reddit.com/r/gonewildstories/comments/njidm7/my_first_fwb_made_me_cum_in_my_boxers_pt_2_video/).

Just 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.

[M]y first [F]WB Made Me Cum in My Boxers, Pt 2: Video Games are much Harder with a Hand around Your Cock

First things first, wow. Thanks to all of you lovely people who commented on, messaged, awarded (!!!), and showed your support for the first part of the story. The reception blew me away, so I obviously had to continue the story. For those who missed it, you can find [Part One here](https://www.reddit.com/r/gonewildstories/comments/nh63ic/my_first_fwb_made_me_cum_in_my_boxers_which_led/).

To recap for those who don’t want to go back and read: 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!). 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. The first time we hooked up, her grinding while we were still partially dressed was too much for my cock to handle, and I filled my boxers.

[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.