This story is 100% true, it’s not quite my first time with a man but where my curiosity took me further than I knew how to go. 18 years old during this story
I was a horny high school senior who was fairly new to dating but hadn’t had anyone long term. I have always been extra curious about men & sex. I’d found porn that belonged to my father & used it many times when I was able to sneak away. His private collection contained multiple genres stuffed in this giant box but I normally grabbed whatever DVD was on top for convenience & quickness. On a particular particular day it was out of order from the usual titles I’d seen strewn about. What initially put me in a panic was a cover I’d never seen before. It had 4 naked men on the cover, no women. Even more alarming to me was my sudden & extreme interest despite knowing it was gay porn. The anticipation. Excitement. The trembling of my fingers & I grabbed it & flipped the case over to see the back. Men on their knees, men being bent over. I was instantly hard & came so hard & quick I thought about it for days after. My brain was reeling because I knew I needed to try it. Regular sex seemed bland by comparison. It never got that excited. Was I bi? Gay? I needed to find out.
This was around 2010 during the infancy of smartphones. You had angry birds but Grindr wasn’t really a thing yet. But lucky for me, Craigslist was alive & thriving & had a giant personal section. Men seeking men. M4m. Hundreds of posts. Thousands? All near me. All looking for the same thing. I made my first post with jittery hands knowing that out of all these men, there had to be one that was close & willing to give a first timer a try.
‘Scoop me up & let me blow you-18m’. That was my title. Not very original but it was to the point. I wasn’t driving & figured a horny guy would be into the idea. My email blew up overnight. I sifted through all of them. Checked distances first. Then by pictures. Got rid of all the younger looking guys under 30(not my thing). As I was looking, one title stuck out in my email. It wasn’t like the rest. It wasn’t horny & it didn’t have any pictures attached. It was just a warning in the heading. ‘Be Careful’ it said. ‘You sound young & inexperienced & an ad like that brings a lot of sketchy people & it can put you in a bad situation.’
I wrote back & agreed but told him my story & my situation. My desire but lack of mobility. I was extremely curious about this man & maintained contact over a few days. His words cautioning but guiding at the same time. Telling me what not to do, but what I could do instead to be safer. I felt safe & warm & looked to a message in my inbox from him every hour I looked. I came to learn his name was Michael & he was a 56yo black gentleman that lived just 2.5 miles away. I knew the exact apartments he lived at. I passed them anytime I got on the freeway as they lined the frontage road. Not nice apartments by any means. Not even decent. But close. The buildings were a beige/yellow color that looked like they were white at one point but faded with sun & cigarette smoke. The roofs & railings were an ugly teal green color. Broke entry gates on either end of the property that seemed to attract homeless people. Shopping carts left in bushes & blankets strewn about. Tattered bodies sleeping on sidewalks feet away from the road in patches of grass. No where I’d ever want to be or live. But somehow that made me even more excited. The more I thought about how dirty it was, how scary & sketchy it would be, the more my heart raced. The more my adrenaline pulsed & shook my hands. I needed it. A part of me wanted to be chased. Lusted after. I lived off the messages from men throwing themselves at me, but not Michael. He was slow & deliberate. He didn’t beg or ask for pictures, nor did he send any. He just spoke to me like a friend or a father after a day at school. After about three days of knowing how close was, I threw myself at him. I begged him to take me. I uttered & wrote sentences that made me seem pathetic. I sent everything I had. I waited & waited. All day. All night. And then I saw it. One lone bold email atop my email.
He didnt fucking drive. He didn’t even have a car. He was from out of state & this or that & he wasn’t able to drive. Fuckkkkk.
Fast forward some weeks, I was actually gifted a car from my older sister & her husband. I had gotten my license several months before as soon as I was able to but had nothing to drive. Until now. I emailed him with a frenzy & we made plans for that Friday. Got his apartment number, time to be there. It was set.
Friday night comes & im in my car driving there. I back into a spot against a fence on the far side of the complex but it’s pitch black. My heart is racing. I can barely move my hands they’re shaking so bad. One slow email at a time I’m given directions on where to go. Through this courtyard. Left turn here. You’ll see this patio on the right. I’m panicking & shaking about after searching for 5 minutes I’m beginning to get cold feet. Maybe my trouble finding him is a sign. The obscured apartment complex looked like something from a horror movie. No lights. No people. Just quite calm. I haven’t found him so I’ll just tell him I got lost & leave. Then I hear a creak of a door. A short, pudgy man steps out of a building straight ahead. He waves me over. I’d already told myself I was going to leave but my legs betrayed me. I was shaking with every step in the wrong direction. I can feel my cock leaking & -my heart racing as I come face to face with him as we do our formalities & shake hands. He invites me inside & as I hear the thud of his heavy, creaking door, I felt stuck. Scared. So turned on.
We sat on the couch watching whatever movie he had on. It was pitch black except for the blue tv flare bouncing off the wall. He didn’t speak. I was too scared to let sounds out. We sat in silence for 15 minutes until I worked up the courage to ask him, ‘can I start touching you?’ He smiles & nods as I get on my knees. I remember it so vivid. The way the spongy cock felt in my mouth. Fumbling around trying to figure out tongue & hand & mouth. I can tell I was terrible but fuck was I turned on. I pull my pants down & jerk myself as I taste him & feel my body start to jerk. I’m close. But he senses it & slowly stands up. I begin to panic, I just wanted to give a blowjob. I didn’t want to bottom, I didn’t know how to bottom. This wasn’t a part of my baby steps of exploration. I was terrified it would hurt. I said absolutely nothing. I just accepted my fate & told myself it wasn’t any less gay to suck cock just because I wasn’t fucked. It was all th same. And I was about to experience it. He pushed me gently down, face first into this cluttered carpet. I vaguely remember pushing old newspapers & ads away to make room. Feeling some crumbs on my forearm as I rested my head. He got behind me & just begged me to please keep it quiet, to use my hands as guides for him. And with a little squelch of lube he slowly enters me. He fucked me slow & deep for about 5 minutes. I barely remember how it felt, I was in such a shock. It honestly just felt like a small pressure. I do remember the light turning on in the middle of it. His strokes coming to a stop. Turning into a statue we were just there in the middle of the floor as his roommate walked out of the only bedroom. Groggy. Incoherent. He stumbled into the kitchen to grab water & he stood there in his underwear staring at us as Michael slowly began to pump me again. He watched while I softly grunted with every thrust & I felt my face turn white hot with embarrassment. Another few minutes of this went on before I felt him pull out & cum in his hand. The roommate finished his water & went back to bed & Michael went back to the couch without a word. Resumed his movie like nothing happened. Fully clothed before I could even process what happened. Still hard, I began jerking myself off slowly on the floor & without looking, Michael tossed a box Kleenex to the floor next to me. I shot a small load, kind of confused & cleaned up. Got dressed & stood up where he gave me a half hug & congratulated me on my first time & said he hoped I liked it. He walked me to the door that was it. My head was empty. I stumbled to my car feeling used. Confused. Still horny. Still nervous. I felt like I was assaulted. But I loved it. I was used & couldn’t wait to do it again. It was dirty in every sense & I knew I was ruined for ‘normal’ sex. I went home andmade another ad immediately & found another play partner. That was probably 100 men ago. I’m a certified, turned out slut now. Women just don’t do it for me sexually & I love it.