[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.

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.

Once again, despite some embarrassment, Haley assured me that she absolutely loved our competition and how fast she won. We continued to chat frequently, though while still living at our parents’ places, it wasn’t very often that we got to hang out. Fortunately, a few weeks after our first little competition, my parents told me that news that is joy to every horny teenagers ears: they’re going to be away for an evening, and leaving me home alone.

Jackpot! You can bet that the first person I told was Haley, who was also quite excited and thankfully didn’t have any plans. It was about 2 weeks from when my parents told me, so we had plenty of time to prepare. And this time, Haley mentioned she wanted to try something a little different… rather than just seeing how quickly she could get me to finish, she wanted to see how many orgasms I could have in our evening together.

Once again, I eagerly agreed to this little experiment. She requested that, to fully test this out, I would need to go a little while without masturbating beforehand, so it could be a total clean slate. I knew that would definitely make me even more sensitive… but I was curious as well, and we agreed that I wouldn’t cum at all in the preceding 5 days (Monday-Friday after school).

An agonizingly slow two weeks followed, though thankfully she was merciful and didn’t tease/sext with me a bunch during that week where I couldn’t get off. I picked her up from her house around 5pm, and was already feeling so on edge. She looked stunning. Tight yoga pants, a light tank top… I couldn’t stop staring at her, and she noticed. When she confronted me about my ogling, and asked me how my week was without release, I was honest: it was incredibly hard, and I was incredibly eager for release.

Haley wasted no time on trying to set her record. I wish I could say that this was another first for me, and I got to experience road head for the first time… but that was not meant to be. Because as we started driving back to my place, I felt her hand on my leg, slow circles moving higher and higher towards my crotch. My cock, pretty much immediately hard after seeing her and talking about my week of no release, was showing a pretty impressive bulge already, and in just a minute or two, her hand found it. I tried to jokingly tell her to stop, that it was dangerous (which it definitely was, given that I was definitely peeking over at her cleavage)… though a large part of my mind didn’t want her to stop. She just kept laughing and telling me to watch the road while her hand gently stroked up and down my shaft from outside of my shorts. Before we got home to my place… she had gotten her first load, my cock spilling a week’s worth of pent-up semen all over my boxers, this time a clear wet spot being apparent even over my shorts. She giggled like she always did when she felt it start to shoot, and told me how excited she was to see how many more we could do.

When we got home, I begrudgingly changed boxers, though didn’t put on any more pants. We definitely wouldn’t need them, as we quickly found ourselves in my bedroom and kissing, tossing and turning again. I told her, like the gentleman that I was, that I didn’t want the focus to just be on my pleasure, and I wanted her to feel good as many times as she could as well. So, after getting her clothes off, for the first time in my life… I went down on a girl.

Laying flat on the bed on my stomach, Haley laying on my pillow with her legs spread wide, I went to work, imitating what I’d seen in porn as best as I could. I’m sure it wasn’t great, though her little sighs and moans and the gentle movement of her hips made me think I was doing something right. I was getting so into it, enjoying the taste and sounds and feeling of her pussy on my face… that I didn’t really recognize that just the grinding sensation, the friction between my cock and sheets of my bed, was starting to get to me. And before I knew it, I noticed that I was getting close to orgasming, with just my hips rocking ever so slightly into the bed while I ate her out.

I tried to pull away and stop, not wanting to end things like this, but I distinctly remember her saying those magic words: “don’t stop”, and putting her hands on my head to pull me back down. In that moment, I didn’t care what was going to happen to me… I wasn’t stopping. I got back to it, and despite the pleasure of gently grinding into my bed, I picked up my pace. And sure enough, just before she finished herself… I felt it happen. Just enough sensation to go over the edge, and once again I’m filling up my boxers while my head is buried between Haley’s legs. After she finished, I moved up and kissed her, and then admitted what had happened… which led to another round of fingering/kissing. She was so turned on by it, and so happy that she got another round out of me (and in my boxers!).

So, after a while, we were both pretty tired and decided to take a break to go to the movies. Typical high school date, sounded good to me. I honestly can’t remember what movie we decided to see… since I didn’t pay a lick of attention to it the whole time. Perhaps stereotypically, we arrived and went straight to the top, as dark and secluded as we could get. And as soon as the previews began, our hands starting wandering again and we were making out heavily.

This time, I can somewhat proudly admit, her rubbing my bulge outside my jeans wasn’t enough to make me lose control. I guess all it takes is some thicker fabric and two orgasms, and my stamina is solid! But… in the dark, with nobody else too nearby, Haley got a little bolder and unzipped my jeans, sliding a hand in to stroke my bare cock. And since this had been at least an hour or two since my previous orgasm… it didn’t take long at all before I was fully hard in her hand again, and she was stroking away while kissing my ear and whispering how much she wanted another load from me.

As if I had a choice, I obliged… and I honestly have no idea how long I lasted, but I eventually couldn’t hold back, my cock spurting again all over her hand and the inside of my boxers. Thankfully the load wasn’t quite as large as the first two… but I definitely remember walking out of the movie theater that evening was much more uncomfortable than usual, with a nice wet stain on my boxers.

So, to answer the question in my title: Haley filled 3 pairs of my boxers in one day, though she did spend the night and I came again the next morning before she left, though thankfully this time it wasn’t in my boxers.

Truthfully, after this there are only a few other fun, note-worthy stories with Haley. We both began dating other people a few months after these events, and then would just casually hook up when we were both single afterwards. Happy to continue sharing those last few stories if people are still interested!

Source: reddit.com/r/gonewildstories/comments/nq3two/my_first_fwb_made_me_cum_in_my_boxers_pt_3_how