The Time I [M] Had a Chance at a Threesome [FF] and Blew It… Literally

Life is full of missed opportunities, and this is one that I still remember to this day. And even if it may be spank bank material, I can’t help but wonder what more it could have been.

To set the scene: I’m Tyler. Probably around 19 or 20 years old at the time, in college, living in a student-style apartment (4 bedrooms, community pool/amenities, etc.). I was probably in the best shape of my life at the time, having played sports throughout high school, but was always more on the tall and thin side than heavily muscular. About 6’0, 170lbs, with short brown hair and brown eyes. No beard at the time, but a bit of chest hair.

The other main characters of this memory are Sarah and Jessica, two girls I had known in high school who had both gone their separate ways for college. I actually briefly dated Sarah in high school (three month freshman relationships are fun, aren’t they?); she was my first kiss! She had a bit of an alternative vibe to her. Fairly short, with shoulder length hair that often changed colors every few months, and a couple of tattoos and piercings. She was a bit chubby but had great curves.

Jessica was someone I was friends with in high school, but never envisioned myself having a chance with. She was taller, just a few inches shorter than me, and rail thin. Flat chest but an incredible figure, with an attitude that exuded confidence. She was hot and she knew it. She had a reputation in high school for having slept around a bit, and being quite good at what she did (side note: I know, high school sucks when it comes to “slut shaming” women who sleep around… but while I’m sure there were bad connotations to her reputation, I distinctively remember the guys who talked about her not trying to shame her as much as talk about how sexy she was).

So, winter break arrives, and I see on Facebook that Sarah and Jessica are coming to town for a week or so for the holidays. I invite them over to hang out, catch up, smoke and drink a bit, and maybe hit up the hot tub at my apartment (living in the South in the winter has its perks!). They agreed, and this is where the fun starts.

The day arrives, and Sarah arrives around like 6pm. We chat and hug and crack open a drink until Jessica arrives around 7. We quickly catch Jessica up, both on the updates in our lives and with the drink count, and start smoking a bit. The plan is to go to the hot tub after a few drinks, so we change into bathing suits; me in my cargo shorts with a tank top, and the girls into their bikinis. And as we drink and smoke, we talk about everything, from how school is going to mutual friends from high school to how we’ve been spending our time in college. And of course, the conversation naturally turns to relationships and who we’ve been dating.

To my surprise, it’s Sarah who offers up that she has primarily been seeing women so far, which begins a whole new line of conversation and discussion. I distinctly remember my first thought being “Oh no, was I so bad that Sarah learned she was gay after we started dating?!” before realizing that she and I hadn’t done anything but kissed. I guess it could’ve been a really bad kiss… but I digress.

This seemed to pique Jessica’s interest a bit, and the topic quickly turned a bit more sexual. She started sharing about all of the fuck boi types who had been hitting on her in college, and even opened up her phone to show Sarah some of the ridiculous dick pics she had been sent, which got some giggles out of both of them.

This whole time, they’re both on my bed while I’m sitting at my desk chair nearby, mostly keeping quiet while listening to these two women discussing their love and sex lives. I didn’t have a ton to contribute to the dating conversation anyways. And I won’t lie, hearing two sexy ladies talk about sex while in bikinis on my bed was just a bit too much for my young adult mind to think about without getting aroused, so I was trying to look inconspicuous while battling an erection in the chair.

And then, the most shocking admission of the evening. After sharing about some of their experiences and people they’d been seeing, Sarah made an offhand comment about how she still felt like she enjoyed being with Jessica more than any of the girls she met in college.

… wait, what?! Sarah and Jessica had… hooked up? I couldn’t just let the conversation pass this, so I chimed in and asked for more details. Turns out, just before going off to college, Sarah and Jessica had begun their “exploring” phase a little early together and hooked up a few times. They obviously didn’t provide me with all the details my horny mind desired, but sometimes leaving things to the imagination is even better.

Sometimes life imitates art, or TV… and this evening, life imitated porn for a brief moment. It seemed that all of this talking wasn’t only having an affect on me, because Jessica mentioned that she missed exploring with Sarah… and leaned in for a kiss. And just like that, I was watching two gorgeous women make out on my bed.

As you could have guessed from the title of this story, I regret to report that things didn’t go much further at this point. Because life is not porn, and they did not immediately rip their clothes off, pull out a dildo, or start tribbing away. It was slow, gentle, passion. Kissing, hands exploring. And yet as I sat there, still in awe at what was happening, my cock was absolutely throbbing in my shorts. I had hardly touched it, yet the scene in front of me was just so arousing.

I do know that this had the potential to turn into a threesome because of what happened next: Jessica briefly stopped kissing Sarah and turned to me. She asked if I was just going to watch or if I was going to join in, and told me to take my shorts off. I never got undressed faster than I did that evening.

Part of why I remember this so well is because of their reactions. I’m quite fortunate to be above-average sized, which is often a fun dichotomy to my thin frame and shy, introverted demeanor. So when I pulled my shorts off and revealed my already fully erect cock, the reactions were perfect. The gentle lip bite from Jessica with a “Wow…”. And Sarah, who I had dated briefly in high school, made a joke about how things may have turned out differently if she knew that’s what I was packing. Damn, this is every man’s dream right here.

But this is where reality sets in. Because as Jessica pulled herself away from Sarah to give me a bit of attention, I knew what was going to happen. I felt her hand reach out to grasp my cock, gently at first, a few long strokes to feel my whole length… I already felt that familiar feeling of orgasm approaching. I thought about all of the things this threesome might entail… blowjobs, fucking both girls, etc., which obviously didn’t help quell my arousal. As Jessica began speeding up her pumping and leaned in for a kiss, all I could focus on was trying to delay the inevitable.

While I may have thought I was subtly trying to hide my imminent climax, I don’t think I did as good of a job as I thought. Because not 30 seconds after Jessica had been stroking and kissing me, she pulled away for a moment. Maybe it was my cock throbbing in her hand, or the pre-cum already dripping out, or maybe I was groaning too much for foreplay. Whatever it was, she just gave me a big smile and said, “It’s okay. Go ahead and cum,” and kept stroking away.

I don’t know why this is, but when a girl talks about cumming, it’s like a switch gets flipped in my head and I can’t hold back. If she says “Cum for me,” I’m gonna cum. If she says, “I’m cumming,” well, so am I. If she says, “Don’t you dare stop, I’m gonna cum,” well, that’s unfortunate, because if I don’t stop I’m gonna cum too.

So when Jessica mentioned in that soft, assertive voice to cum… that was it. Less than a minute of a handjob and kissing and I felt myself go past that point of no return as my cock began to twitch in her hand… and unload. Several thick ropes of cum in her hand, all over my sheets. And that was all she wrote.

If Sarah and Jessica were disappointed, they acted like saints not to show it. Jessica seemed genuinely excited to see me cum like that and kissed me again, while Sarah, who had been watching, had a big smile on her face as well. After she stopped stroking me and had cleaned up her hand a bit, Jessica went back to kiss Sarah a little more, but that was basically the end of it. Life stopped imitating a porno and we eventually made our way down to the hot tub for a bit.

I never saw either of them naked, and unfortunately this was the only encounter with these two. We stayed in touch for a while before drifting apart, but this was the only time anything like this ever happened with us.

I always enjoy chatting and sharing stories, so feel free to DM or chat me if you’d just like to chat. Particularly if you enjoy big dicks and/or premature orgasms, since those tend to be my specialities =P

Source: reddit.com/r/gonewildstories/comments/uwoe1j/the_time_i_m_had_a_chance_at_a_threesome_ff_and