So sophomore year of college, I was your average shitty loud virgin white boy. I know, hard to believe considering my shitty loud slutty androgynous self now. Suspend your disbelief for the story:
So I’m out to literally no one, not even myself yet really, but I’m soooo horny. I’m looking everywhere. Tinder, Ok Cupid, the fuckin yik yak app. No luck. I’m jerking off basically daily when my roommate’s not in the room (and pretty often even when he was). I *need* to lose my virginity, and I’m running out of options.
So I try craigslist.
So many old men, just searching for college girls who want a free place to live. Unnecessary dick pics, terrible grammar and spelling, the whole shebang. At this point, I’m just tryna find cute college girls who want a fwb, like any rational person would be. So I’m always surprised, and kinda weirded out when these guys respond to my ads. Like, I’m all for shooting your shot, but I’m posting as a straight dude. Like what are the chances Ima respond, come on.
But god dammit, they must have worn me down, cuz the slut I am started putting m4a. “Why not?” I thought. Any attention is better than no attention. So I start reading through some of these responses, and fuck, did it feel good to be wanted that bad. It blew my mind how much people drooled over the pics I posted. Talking about draining me of cum, worshiping my body and giving me pleasures I’d never felt before. Just the thought of it had me hornier than I already was.
So one day, I decide to respond. I post, “Looking for tonight.” I get responses of course, but I wait for one that seems rational. I’m in the campus library when a message with this subject hits my inbox: “42M, Professional top, love your pics.”
So I message back. “Hey! Glad you like, ok that I’ve never done this before? Little nervous.”
“For sure, I can be really gentle, and I wanna respect your boundaries. Free tonight?”
I’m freaking out. “Yea, totally, do you have a place? I can’t host.”
“Sure, we can go to my office just outside of town.”
“Cool, I’m at the library.”
“Be there in 20.”
Holy. Fuck. This is happening. This complete stranger is on his way to pick me up, and no one knows. If you’ve never been in this situation, the rush of not knowing whether the guy coming to fuck you is a serial killer is intense. I was extremely naive, so I thought it was normal; like, I told myself it was just the rush of impending sex. I gather up my shit from the library, and head down in front, and send an email saying: “Just look for red hair, I’m the only one.”
The car he described pulls up, and he rolls down the window. “Mike?” I ask. He smiles, and nods.
“Adi?” He said my now deadname of course, but ya know.
“That’s me!” I smile, and get in this fucking stranger’s car. What the fuck am I doing. We start driving, and I’m like *Should I suck his dick? Does he want me to strip, should I text someone where I’m going?* Before I can decide, he starts chatting me up, talking about his days in college as a frat boy, how he was an athlete and isn’t really out to anyone. Honestly, bless him for making it somewhat normal, it really helped to cut the tension. Eventually, after about fifteen, twenty minutes, we pull into the lot of his work.
He turns the car off, looks at me, and smiles. “Shall we head inside?” I nod. We get out of the car, and he tells me to wait outside while he checks that no one is inside. I do, and after a minute, the guy opens the door, and gestures me in.
“To the right.” He points to a door, and I enter. I stand there and look at him. After a moment, “Do you wanna suck my cock?” I nod silently, and drop to my knees. He undoes his pants, and pulls it out.
Literally without hesitation, I put it in my mouth. I shit you not, it felt so right. It felt like I was born to do this. Sucking gently, sliding my lips up and down his shaft, using a hand to reach the shaft I couldn’t get down my throat. Remember, I’ve never even sucked a dildo, or a goddamn popsicle like this, so these skills are just as shocking to me as they were to him.
I suck until I’ve got him hard, and after a bit of him moaning and stroking my hair, he asks, “Do you want me to fuck you now?”
I pull his hard cock out of my mouth. “Yea. How do you want me?”
“Doggy.”
We reposition, he puts down a towel, applies a condom, and begins lubing me up. Y’ALL. The moment this man’s cold, lubed up finger touched my tight virgin asshole was the very moment that led to me being the person you see in all my pictures. It was e u p h o r i c. My whole body shivered. I sank into the most submissive, hip opening doggy position my body would allow. I can only imagine the view he had: moonlight from outside lighting up my plump pale ass, short haired ginger boi moaning like a bitch on the floor of his office. His finger went from lubing me up, to gently sliding in and out of me.
“That ok?” he asks.
“That’s amazing..” Moaning louder now. He keeps fingering, telling me how he’ll start slow, and speed up once he’s in, and if anything at all feels off, say something. Y’all, seriously, I got so fucking lucky with this man.
“Ok, Ima put my cock, in. You ready?”
“Fuck yea.” I’ve never been more certain of anything in my life. The head of his cock, wrapped in a condom, pressed against my asshole. His hips bump against me, and I feel his cock bend, not quite hard enough.
“Fuck, I can’t stay hard with the condom. Do you mind if I take it off? I’m clean.”
Nervous, but with a fuck-it mentality, I say, “Yea totally.”
I hear the *snap* of him pulling off the condom, and then I feel it. His now hard cock pushes gently into my ass. A quarter, then out. Halfway, then out, Two thirds, then out. Tantalizingly slow. “That ok?” I nod, and moan, biting my lip. Finally, he pushes all the way in. “Fuck..” He moans, the slapping of his hips on mine signaling his lack of restraint.
He fucks me for real. Rhythmically, sensually, pushing and pulling his hard daddy cock through my tight, no longer virgin boi pussy. No pain, no friction, nothing to ruin this absolutely perfect moment. Just a comfortably thick cock gently stretching me, hips bouncing off my bubble butt and rocking my whole body. He squeezes my ass, pulls my hips onto him, and for who knows how long, we exist in this blissful carnal state.
“Do you want me to cum on your ass or on your face?”
“Ass.” I say, but not wanting it to end.
He pulls out, I hear fapping behind me, and I feel hot curtains of semen drape my tush.
Feeling satisfied, so, so satisfied, I stay in my position. My legs are spread, asshole slightly agape, panting from the experience. He wipes his load off of me, and slaps a cheek once more for good measure, then we get dressed, hop in his car, and he drops me off, wishing me a good night. Oh, and on the way home, he definitely told me, “You’d really never done that? You took my cock so quickly! Barely took any warming up!”
I go back up to where I was studying in the library, and inner slut awoken, finish my homework.
I swear to Jengus Christler, this happened. It’s been a while, so the convo is a hair fuzzy, but I lost my virginity to a stranger with no condom in his office at 11:00 p.m. The funny thing, is I never considered that my first time until like 5 or 6 years later. Heteronormativity convinced me that my first time had to be with a woman.
If you ever find yourself in a situation like this, let me be the first to say: DON”T FUCKING DO IT. That shit could have ended so goddamn bad, and I got REALLY lucky. I didn’t even catch anything from it, despite the EXTREMELY IRRESPONSIBLE DECISION TO LET HIM GO BAREBACK. That being said, I had a blast, and Mike, if you see this, thanks for being amazing.
TL;DR: 19m me met 42m on craigslist and 42m fucked me in the ass in his office in the middle of the night without a condom, no one knew where I was, and I had an amazing time. Don’t do this. You could die.
Source: reddit.com/r/gonewildstories/comments/ipsvg0/26_nb_when_i_was_19m_i_lost_my_virginity
Was perfect until you had to put the heteronormativity line in there, there are plenty stories here whos first time is same gender, none of them make it a same sex pc thing. But nonetheless great story