My First Gay Experience [M/M] Warning: Story is long!

My first gay experience.

I’m new to posting on Reddit. Been around reading and checking out this sub for quite some time though, finally decided to share my story with everyone. I’ve never told anyone this before, figured I would get it all out in the open. Sorry in advance for its length.

I guess I’ll start by saying that I’m 28 now and the events in the story took place a little over a year ago. I’m from small town, Bible belt USA. Grew up in a town where everyone knows everyone, and I was always really popular in school, and had the reputation of a ladies’ man. Anyways, it was around 8th grade when I first found myself attracted to another guy. It was random, completely caught me off guard. I was sitting in History class when a tall, athletic, black guy named Tim walked into class. I was completely thrown off by how attracted I was to him. I would sit in class and stare at him, fantasizing, getting myself so turned on I could hardly control the desire let alone concentrate on class, just waiting until I could get home just so I could masturbate to the thought of kissing him or having his thick lips on my cock. This went on for some time, until he moved away the next year.

I obviously never told anyone that I had those thoughts, let alone acted on them and after Tim moved, they basically went away. I would find myself attracted to random people here and there, random celebrities. I remember being really turned on by Marilyn Manson when I was younger. But other than the random person, I was really still only attracted to women. I went through High School dating, having girlfriends, and the feelings and fantasies went away. Well, there was one time at a party where I drunkenly told the one openly gay guy at our school that I would fuck him, but other than that, there was nothing.

So anyways, almost a decade passes. In that time I’ve met a girl, moved in with her, got engaged, she ended up cheating on me, so I moved back to my hometown to start over again. Being single and lonely and horny and back in a boring town that I hate really got to me. I decided to try looking for a hook up on dating sites, something simple and discreet, but after weeks of trying, and multiple profiles, I didn’t find anything worthwhile. So, late one night, I get bored, horny, stoned, and decide to try and see if I had any luck with any single guys in my area. I figured it was time to finally try it and see what it was like after all my earlier fantasies.

So I set up new profiles, sent a few messages to guys I found attractive (twinks, all twinks, I’ve noticed. Quite the shift from my first same sex attraction) After weeks of nothing, I almost forgot about it, until one day I received an email notifying me that someone had messaged me on one of the sites. I checked my message and saw that it was from an 18 year old guy who lived in the same town as me. I checked out his profile and was immediately attracted, just the way I was with Tim. He instantly turned me on. He was short and skinny, wide brown eyes with long brown hair, feminine features, pale white skin, and thick pouty red lips. I definitely wanted to meet him.

So, after messaging back and forth a bit, I realized that he lived with his grandma who happened to stay only a few blocks away from me. I hate to admit this but, after my break up, I had to move back in with my parents for a while to get situated. Being broke, depressed, and living with your parents in your shitty hometown can really put a cramp on your sex life. Makes it even harder to meet a guy for your first random gay hookup, especially when you’re already nervous enough as it is. I doubt my parents would care, I know they would support me whatever my sexual orientation, but I wanted to keep this secret from them, as well as my friends.

Here’s where I feel like an asshole. We made plans to hang out a few times, and every time I would blow him off with either no excuse or no warning. I was scared suddenly, worried about what would happen, would anyone find out, and instead of being mature and talking with him about, I took the shitty childish route and blew him off and stopped talking to him. He would text me, call me and leave messages sounding really hurt and confused by my actions, and I never responded. This went on for weeks, and finally he decided to stop trying and I decided to try and move on like it never happened and put it behind me.

I finally got a new job, started making good money and turning myself around again. I bought a new car, paid my parents back for rent, and started saving up for my own place. I spent most of my time either working or hanging out with the 1 or 2 friends I still had left in this town. After weeks of getting back on track, one day at work I got a call from Shannon (that’s the guy’s name, guess I should have said that earlier, sorry) and it stuck with me. I started to think about him again, fantasizing while I was at work, and it made me feel good, helped me get through the day. I decided to start talking to him again, and I became determined to go through with this and finally make it happen. I wanted to fuck him and despite my fears and anxieties, I was going to make it happen.

So, one night I sent him a text and explained everything to him. I told him I was new to this, had been curious for a while but I was just scared. I apologized profusely for my immature behavior and surprisingly, he took it in stride and forgave me. It felt good to clear the air, and as soon as that was over, we made plans to hang out that night. He told me he would drive over around midnight and we could sit outside and hang out in his car, which sounded good to me. So, later that night, feeling like I was in High School again, I snuck out through my window and met him outside. He was even sexier in person, which immediately made me nervous. We sat in the car talking for over an hour, laughing about the situation and he reassured me that he was over it and all was forgiven. It was hard for me to concentrate, I wanted to get past the awkwardness and all I could think about was how I could make a move and kiss him. At the end of the night, after almost 2 hours of sitting in his car in front of my driveway talking, he turns to me and asks me if I’m going to kiss him goodnight. I smile awkwardly, obviously blushing, and instead of responding I just look at my lap like an idiot. After what feels like an eternity of silence I feel his hand on my chin, and he lifts my head, turning me to face him, and next think I know his mouth is on mine. He kisses me softly, slowly, his tongue barely sliding into my mouth, barely gliding along mine. I instantly get hard, pulling him into me and we make out hungrily in his car like teenagers.

After that night, I was hooked. It was all I thought about. We talked constantly, trying to make plans to see each other again, but our conflicting schedules made it difficult. After a long day of work, I decided to go to the bar with a couple of coworkers, and we ended up closing the bar down. On my way home, all I could think about was how badly I wanted to finally have sex with another guy. I texted him to see if he was busy, and right as I got home he messaged me back saying he was free and that he would come over. I showered quickly and changed clothes hoping I didn’t reek of alcohol or cigarette smoke from the bar. By the time he texted me to tell me he was outside, I was so turned on and excited and nervous I couldn’t think straight. Instead of going out to meet him at his car, I tell him to come around the side of the house to my window and I would meet him outside. I climb out my window just as he rounds the corner and walks through the gate, and after a nervous yet pleasant greeting, we decide to sit down against the side of my house and talk. Things start off painfully awkward, my inexperience causing me to second guess everything I say or do, and finally the anticipation was too much to take and I leaned over and kissed him mid-sentence. His thick wet lips felt good against mine, and my mouth opened reflexively allowing his tongue to slide into my mouth and I sucked on it hungrily, licking at his lips as I pushed him back onto the ground.

I laid him down on the grass along the side of my house, our mouths pressed together, tongues entwined, and I began to rub my hands along his body, sliding underneath his shirt, his pale slender chest smooth and hairless. I rubbed his creamy flesh, moved down to his pants, and slowly began to fumble with the buckle and zipper before he reached down and helped me slowly slide his pants along his ankles. I reached down his boxers and gripped his hard cock, slowly stoking it as I kissed along his chin and neck, tracing my lips down along his nipples, his sternum, stomach, and before I knew it, his boxers were gone and I had my lips wrapped around his penis.

I was lost in the moment, trying my hardest to pleasure him as best as possible, but at the same time my mind was racing with pure excitement at the fact that I was actually giving a guy a blowjob, outside my childhood bedroom window no less. So I licked and sucked at his head, stroked the shaft, slide my tongue up and down, trying to deepthroat as best as I could, hoping to make him cum. At that moment all I wanted was him to blow his load in my mouth. I just wanted to suck him dry, but before I got the chance, he was pulling my head up, guiding my mouth back to his and without hesitation our lips were back together.

As we made out noisily in the dark, his hand began to slide down my pants, and I furiously fumbled with the zipper, trying to get my pants off as quickly as possible. The thought of his mouth on my dick was causing me to shiver with anticipation, and soon the anticipation gave way to reality, his thick lips wrapped expertly around my member, taking it all the way to the back of this throat. I couldn’t control my moans, it was the best blowjob I had ever had, and soon it was getting even better as he started to slowly lick up and down my testicles, up along the shaft, and just as he took it all in his mouth again, gagging slightly (which made me feel good,) he slid two fingers up my asshole. My body throbbed at the insertion, pain and pleasure overlapping, and just before I could cum, I pulled his head away from my penis and without thinking moaned “Oh god, I want you to fuck me….”

Now, when I would fantasize about fucking him, I always envisioned me being the top and him being the bottom. I wanted to know what it felt like to fuck a guy. But, before I could really grasp what I had said, I was standing up, hands pressed against the wall next to my window, slightly bent over as Shannon spit repeatedly in his hand so he could lube up his cock and my asshole. The positioning was awkward and didn’t seem to be working, so he pulled me away from the wall, pushed me to my knees and slid in behind me on the ground, grabbing my hips and lifting my ass into the air. He slid his cock in slowly and I gasped at the pain. It hurt bad, but after my anus was finished contracting, he began to slowly grind against me and I couldn’t help but let out the loudest, girliest moan as he impaled me with his thick cock. After that, I blacked out. I don’t know how much time passed but the next thing I know, I’m reaching behind me, grabbing onto Shannons head and sloppily kissing him, moaning into his mouth as he grunts repeatedly, biting my lip when he cums, and I feel his penis quivering as it explodes in my asshole and the thought of it makes me cum shortly afterwards and we collapse on the grass together in a post coital lump.

After a few minutes of laying face first in the dewy grass, we both slowly come back to life and pull ourselves to our feet, slowly and awkwardly re-dressing. After a few minutes of near silence he turns to me and says “Wow, I’ve never done that before,” and laughs. I laugh too. I give him a quick kiss and climb back into my bedroom as he turns and heads home. I laid in bed that night and re played the whole scene over and over until it got me excited enough to masturbate, and as I came I felt proud of myself that I finally went through with it.

Thanks for reading everybody, sorry again it’s so long. Thanks for sticking it out, hope to hear some feedback!

Source: reddit.com/r/gonewildstories/comments/37kk94/my_first_gay_experience_mm_warning_story_is_long