u/InformalPeach102

Obligatory everyone was 18+ in this story.

So about 6 months after I got head in a steam room on a cruise ship (if you want to read that story, it’s posted here), I desparately wanted to feel what it was like to get fucked.

As a senior in high school, scared of anyone finding Grindr on my phone, I decided to confide in the one gay classmate I knew. He was very open about his time playing with other men, but he seemed very trustworthy in being able to keep a secret.

One afternoon, I sent him a text, asking if he could keep a secret. I think this coming out of the blue gave him more than enough of a hint as to what was coming, but I eventually tell him I’m curious what it’s like to get fucked, and I wanted to experiment with him. He was open to the idea, and we made a plan to meet in the parking lot of the clubhouse in his neighborhood that night. I told my parents I was going to a friend’s house to play video games, and did what I could to prep for his dick in my ass (though looking back on it now, my prep was very much lacking, and I’m surprised there weren’t any unfortunate accidents lol).

We park in the empty parking lot and I climb into the back seat of his car. He can tell I’m extremely nervous, so we chat for a minute about random things. I tell him I don’t know how to proceed, and so he says, “what would you do if I did this?” And places his hand on my crotch, gently rubbing my cock through my shorts. In response, I reach down and start to rub his, feeling it growing in his shorts. I tell him I want to see it, and he takes his shorts off, revealing a 6” cut cock, somewhat thin but with a nice mushroom head, neatly shaved pubes, and some very stark speedo tan lines.

I take a hold of his cock, gently stroking it with my left hand as I take my own shorts down with my right hand. Once my shorts are off, he lets go of my cock to pull me into a kiss. We make out for a minute, tongues fighting, before I pull away, asking him if I can put his dick in my mouth. He adjusts himself to give me more room to explore, and I lean down, his dick just inches from my lips. I’m nervous as hell, having never sucked a dick before, but the butterflies are soon replaced by a primal urge to take his cock in my throat. I lick his head, then dive in and take as much of it in my throat as I can. Having never done this before, I gag almost immediately, tears streaming down my cheeks as I cough on his dick.

He coaches me through my first blow job, and as I take his advice, I taste his precum on my tongue, salty, but also a bit sweet. He put his hand on the back of my head, guiding the rhythm, and my dick throbs as the overwhelming sensation of sucking a dick makes me even more aroused.

After a minute or two, I take his dick out of my mouth, and I ask him if he wants to fuck me. He says yes, then reaches into his shorts on the floor and pulls out a condom. He tells me to get out of the car, and follows me to the front of my car, both of us bottomless in this neighborhood parking lot. The thought of being fucked in public has me so aroused, I don’t think twice about the ramifications of getting caught, so I oblige him.

He lubes up his finger, rubs my virgin hole, and tells me to breathe out as he slides his finger in. It feels so good going in, and he slowly fingers my ass before adding a second finger. After a minute, he takes his fingers out, and bends me over the hood of my car, telling me to breathe slowly, that it’s probably going to hurt, and presses his dick against my hole.

As the head of his dick pops through my sphincter, the immediate burning is too much for me to bear, and I tell him to pull out. Lightheaded, I start breathing heavy, feeling like I’m going to pass out, leaned up against the hood of my car. He tells me the pain will subside if I let myself acclimate, and I agree. He presses his dick inside me again, and the pain immediately returns. I try to breathe slowly, and after a few seconds, the pain subsides, and the realization that there is a dick in my ass causes the arousal to flood back, pain now a rising pleasure in my ass.

He slowly starts to slide in and out, and the pleasure continues to rise, pressure in my ass causing my dick to throb uncontrollably as he starts to fuck me faster.

After a minute or two of adjusting to the sensation, he grabs my shoulders, picking up the pace, fucking me hard and fast, and my mind melts into the pleasure of getting fucked for the first time. It doesn’t take long, but I reach down and start to stroke my cock, maybe 30 seconds before I tell him I’m going to cum.

He continues fucking me hard, and I can’t contain it anymore. I start to cum the most intense orgasm I’ve ever had, blowing my load all over the grill of my car. He maintains his pace, and maybe 60 seconds after I cum, he tells me he’s going to cum too. He pushes deep into my ass, burying his dick inside me so our balls are pressed together, and cums inside my ass. He pulls out, pulling the condom off, and lets the cum fall on the pavement. After a minute of heavy breathing, he kisses me, tells me my ass felt amazing, and tells me I’m probably hooked now lol.

We get dressed, say our goodbyes, and both drive home.

And that’s the story of my first time getting fucked. Hope y’all enjoy, I have some more stories if anyone is interested, thanks for reading!

Obligatory everyone was 18+ in this story.

So I had pretty much always been curious about what playing with a man was like, watched enough gay porn leading up to this point that I wondered how different it would feel from being with a woman.

I was 18 on a family cruise to celebrate my brother’s birthday. Spent plenty of time on board the cruise ship with the family, doing the typical family things.

One morning, I decided I wanted to get in a workout at the gym before the day’s activities, so I left everyone in their rooms and worked out. Confirmed after my workout that everyone was still in their rooms, getting food, not coming to the gym being the most important detail, and I decided I would get bold and try sitting naked in the sauna, trying my hand at a little exhibitionism.

Walked into the sauna and there was only one guy already there, sitting on the bottom row of the benches. I asked if he minded if I sat with my towel open, as I didn’t want to get told to leave by security, and he accepted. I sat across from him and opened my towel and spread my legs, letting my hot, sweaty balls hang freely. He opened his towel to reveal quite a small dick, so I knew I wasn’t interested in trying anything with him, but being nude in a public space was exhilirating.

Shortly after I sat down, another man came in. I sort of panicked, as I didn’t know if I would get in trouble, and I loosely covered myself, but he didn’t seem to mind. He sat across from me, on the row of benches above the other man, and opened his towel. We all sat in silence, dicks hanging freely, and I noticed the second man eyeing me up and down, eyes lingering on my dick. He nods at me, making a point of looking at my dick, then sort of motions his head toward the door. I nod back, and I wrap my towel around my waist as I stand up. I tell the two men “have a good one,” and walk out of the sauna into the adjacent steam room which was empty.

I sit down toward the back of the room, in the thick of the steam, and the second man follows me in and promptly sits beside me, undoing my towel. He doesn’t say a word, just reaches in and starts stroking my cock with one hand as he undoes his own towel with the other hand. I nervously reach over and grab his cock, and he takes this as a sign that I’m into it, and he quickly dives in and puts my dick in his mouth. I start breathing heavy, the growing horniness pushing out every rational thought in my brain, and I start to melt in the sensation of his lips around my cock. He uses one hand to stroke my cock into his mouth and takes his other hand and gently starts to probe at my asshole.

At this point, I can’t hold it anymore, and I tell him I’m going to cum. He doesn’t slow down at all, and I blow my load directly into his mouth. He doesn’t waste a drop, swallowing it all at once, and then pats my thigh with a smile. I get up, tell him thanks, and walk out of the steam room.

I got out, wiped off in front of my locker, and get dressed. Saw him one other time that day by the pool with another man who appeared to be his husband, but I don’t think he saw me.

And that’s the story of my first time with another man. I have plenty of other stories if anyone is interested in hearing them.