How My Daddy-Kink Turned Into My First Threesome

Introductions are best done first. I’m Oliver, I’m 19, I’m a gay man, and I’m about to detail my first threesome. Now that we’re assimilated, allow me to share some context.

I’ve always been attracted to men slightly older than me. Or significantly older than me. Or decades older than me… Which is why I started seeing a 51-year-old man right around April of this year. It began after I turned 19, while I was working an internship in LA I had just started trying apps like Grindr and had found this man (Let’s call him Sam) that lived in the area. He was cute, and much, much older than anyone I had been with before. His age was by far the most attractive feature about him and made every one of our encounters thrilling. We met up and did all the normal first-time date stuff (dinner and such). Then we came back to his apartment. What happened next was my first experience of the type, considering every other guy I had been with until then was my age and was relatively inexperienced in terms of what was about to happen. Sam and I, despite the 32-year age difference between us, had the most passionate, engaging, and exciting sex that night. Things were hot off the bat, fulfilling my stereotypical daddy-kink. Beginning with rough foreplay, submissive blowjobs, and eye-opening ass rimming, we quickly melted into rough and erotic sex, filled with just the right amount of pleasure and pain. The 32-year age difference came with an experience difference too, and it stood out.

Fast forward six or seven hot hookups, and I’m sitting outside my house texting Sam. We talk about meeting up that night with the usual tongue and eggplant emojis. I put my phone down to do something and when I come back I see another message from Sam. “Care if someone else joins us tonight?” A slight head-rush comes up and I struggle to find an answer in my head. A three-way? Sounds fun, but am I pushing too many boundaries? My head rush passes, and my thumbs are already at the keys replying with an appropriate amount of emojis and an indirect “fuck yes.” What have I got to lose? Sam and I exchange a few photos and, and I’m even more excited for the night. The guy joining us is twenty-seven (I think that’s one from every generation), a friend of Sam, and hunky. Let’s call him Alex.

It’s 8:30 and I’m finally driving to Sam’s apartment. I’m more nervous than usual, partly because this is my first threesome, and partly because I’ve never met this guy before, AKA, I’m having sex with a complete stranger without meeting them first. I wasn’t sure if I was excited or horrified by that. As I got closer to Sam’s, I began to lean towards excited. How many times are do you get to blow someone within minutes of meeting them?

I finally get to Sam’s complex, and with a racing heart make my way to his unit. At this point, thoughts are flushing out my head—mostly about how to introduce myself to someone completely new that I know I'm about to fuck. My head is kind of in a haze at this point, with absolutely no expectation of what’s about to happen. Then a message pops up on my phone. “Alex and I are having fun. Just knock.” Great, they’re already naked in bed and I’m about to knock on his door. How the hell do you meet someone for the first time as they’re already in bed with someone else? My head gets woozy.

It’s 9:05, and I finally knock on his door. My heart races a little more, but the door creaks open within seconds. “Come in, we’re in the bedroom,” whispers a naked silhouette. It’s Sam. I make my way into the dimly lit living room and follow Sam to the bedroom. I’m on auto-pilot at this point, about to turn the corner into the bedroom holding someone I’ve never met, who’s about to fuck me. I round the corner and there’s Alex, on his knees, kneeling on the bed. I get out a keen “nice to meet you,” and begin taking off my clothes, unsure of what else to do.

I start to unwind as my clothes come off, and things start to get fun. Sam pushes me onto the bed and onto Alex’s dick and starts eating my ass. As Sam eats me out, I continue blowing Alex almost in rhythm. Sam’s ass eating skills push me into a trance-like state, allowing me to deep throat Alex with ease. After a few minutes, Sam throws me on the bed and Alex starts to eat my ass while I take on Sam’s dick with my mouth. Alex spits into my ass and continues rimming me, then moves onto fingering me. One finger turns to two, and then to three. Eventually, I feel wet enough and let Alex know he’s free to go in. He start’s jerking me off and slowly enters me, pulling out and pushing further each time until he’s finally thrusting in and out of me. All the while his thrusting is pushing my mouth back and forth over Sam’s dick. My back arched, Alex continues pounding me and jerking me. Sam steps away and throws the rest of my body over the side of the bed. He joins Alex behind me and they take turns pounding my ass, going back and forth. Alex takes my ass and starts pounding me again, this time rougher than I’ve ever been pounded before. Sam comes back to my mouth and pushes my head down on his dick once more. Eventually, Alex cums and falls over to the side after thrusting a bit more. Sam flips me over and cums on my face, and follows after Alex by laying down on the bed. Alex and Sam take turns jerking me until I finally cum too.

By the end of this all, I’m out of breath and completely unsure how to process what just happened. It was by far the most promiscuous thing I’ve ever done and by far the most thrilling. Have I betrayed my “boundaries” by engaging in such a rough threesome? Or was this just a pleasurable experience and nothing else? My post-sex pondering has me concluding this promiscuous Friday night wasn’t anything crazy, but just an expression of sexuality that was filled with supreme pleasure. Unless you consider sex to be a sacred act of the ever-holy human body, this was nothing more than an adventurous engagement that pushed beyond social boundaries for some unprecedented pleasure and thrill. And it’s something I would absolutely do again, should the chance come up.

After that night, I have come to appreciate what group sex can do. With a sexual sphere dominated by single-partner sex, group sex can feel like a thrill pushing us just beyond our comfort zones into a sexual thrill zone. Group sex is a pulsating experience, and because of that an unmatchable sexual experience if you’re up to it. So, if right now you’re wondering if a threesome is for you, heed my message: It absolutely is.