Straight Boy to Bi Bottom

This is my first story. Please feel free to leave constructive feedback and let me know if I should continue.

The following is a true story, with minor embellishments, of my first gay experience. Everyone in the story is an 18+ consenting adult. NOTE: if this story encourages you to use Craigslist or another online site, please be safe. My biggest tip is if something doesn't feel right about it, do not meet that person. Never give personal information to a stranger.

When I was in high school I started becoming more and more interested in cock. I'm not gay, as in I've never been romantically interested in men, but something about cock really gets me going. It started with shemale porn and gradually grew into both shemale and gay porn. All throughout college I would alternate between straight and gay porn. I just kept coming back to it. Eventually I bought a toy, but had to keep it hidden because my girlfriend wasn't really interested in that kind of play. I was always interested in what it would be like to get fucked by a man and suck cock, but was too nervous to do anything about it; and honestly I wasn't really sure where I would start. After graduating college, however, I was spending time near a big city waiting for fall to come so I could move to another state with my girlfriend. During this time I discovered craigslist. I put an add up, just to see what would happen, but chickened out after a few emails. As fall was growing nearer, I decided it was time to just go for it. This was something I've always wanted to try, so why not just do it? I'd be leaving soon, so there was really no reason not to just do it.

I put up another ad: Bi Curious Young Bottom Looking for First Cock" along with a picture of my shapely ass. I knew I would get a bunch of responses, because I have a very nice ass, but only one really caught my eye. It was a POV of one of the best looking cocks I have ever seen. It looked to be about my length, seven inches or so, but THICK. I've always been kind of a size queen, so this cock looked perfect. The man was in his late 30s and had a little bit of a gut, but overall in fairly good shape. We emailed back and forth a little bit and he seemed to be the perfect guy for my first time.

The day came when I would drive over to his place. I would be buzzed up then just walk into his place. He would already be on the bed naked. We had decided to keep it mostly anonymous. No names and the only light that was on was the porn playing on his TV. I was so nervous on the drive I actually turned around and had to force myself to go through with it. I just had to remember how much I wanted this and how hot his cock was going to be.

When I got there, everything went as planned. He buzzed me up, and I walked through the door. I was still really nervous, but as soon as I saw this man on his bed jerking his cock...something changed. I immediately got turned on, just looking at the scene. The porn that was playing was two young, hung, guys going at it in a whirlpool, which was definitely adding to my horniness. So there I was in my shirt and sweatpants, standing at the foot of a strangers bed, as he stared at me stroking his thick cock. At that point instinct just took over and I began to strip. But I wanted to be at least a little seductive, so I tried to be as slow and sexy as possible. After taking off my shirt, I turned around to give him a nice view of my ass, and bent over as I pulled my sweatpants off. After kicking them away, I stood straight up and arched my back, put both hands on my ass and gave it a nice spank. I was rewarded with a small moan, he was really liking the show! Then I turned around and climbed onto the bed and in between my mans legs. He let go of his cock, which was the first time I could get a good look at it. I was not disappointed. It was a good length, but fuck...this cock was thick. I wrapped my hand around it and just looked at it for a minute. I was in awe. It felt really good in my hand. His cock was hard, but soft at the same time. The only way I can really think to describe how it felt to be holding another man's cock was, amazing. Now I have a pretty good sized dick, but he was putting me to shame. I could barely get my fingers all the way around this hot piece of meat! And he had a perfectly proportioned head. This cock was a thing of beauty. Although we were both enjoying me stroking his cock, I desperately wanted it in my mouth. Fantasizing about giving a blowjob, and practicing on my dildo make me hard as a rock. I started by licking his cock all over, especially his head and slit. I had just moved to licking his balls when he said the only thing he will have said all night, "take your underwear off!", and he even started to reach over me to pull them down.

I stood up and gave him another show of my ass as I took my tight briefs off. Now that he could look at all of me, I got back between his legs with my ass in the air, and I made sure to arch my back to give him a good view. This time I jumped right in and took his head in my mouth. I wanted to suck him for all I was worth, but I also wanted to enjoy my first blowjob and explore my first cock. I sucked his head and licked around his slit, trying to tease him as much as possible. I could tell my his moaning that I was doing a good job. After a minute of teasing him, I started trying to fit as much of that cock in my mouth as I could. It took a few minutes but I ended up getting almost the whole thing in my throat, as my forehead pressed into him belly. I continued to alternate deepthroating him as best I could, and licking and worshipping his cock. After a few minutes I said, "I think I'm ready to fill a different hole with this thing". He didn't waste any time grabbing a condom and lubing up. The whole time I was spreading my ass and giving him a show.

After he put the condom on he laid back down so I could ride him. I climbed on top and grabbed his thick cock and lined it up at my hole. This was it. I was going to get fucked. I have never been so turned on in my life. I pressed his cock head to my tight hole, and started to lower myself. Now I've used toys before, and it usually hurt just a little bit at the beginning, so I was ready to take it slow...but for some reason his cock just slid right in with no discomfort. And oh my god...it felt AMAZING. He was so thick, and stretching my tight ass in all the right places. I rode him for a couple minutes, as he stroked my cock and rubbed my chest and abs, but there was something about the angle and I was only able to get a couple inches inside of me.

Since I was getting a little frustrated, I told him to fuck me from behind and turned around on the bed and got on all fours, again making sure to arch my back so he could get a good view. He got behind me and just slid that big dick in my tight hole. This time, however, he slid all the way inside until his hips and belly were resting against my round ass. Without even thinking the words came out of my mouth, "Oh yeah, that's it baby. Fuck me with that big cock!" And he didn't waste any time. He immediately started pounding my ass. I was moaning like a girl every time he would bottom out inside of me. I couldn't control what was coming out of my mouth, "Oh god fuck me" "Spank my naughty ass" "Don't stop!" "Give me that thick cock!". All the while he was giving me exactly what I was asking for. All I heard from him was grunting as he fucked me for all he was worth. Eventually he started fucking me fast and I knew he was about to cum, "Yeah that's it stud, cum in my ass" "Fuck, that cock is so good!". That sent him over the top and he came inside of me. After he pulled out I realized I hadn't even touched my rock hard cock. So as he laid down on the bed, he pulled me to his mouth and started sucking my cock. I can't say I was excited about this, but it did feel really good! As he sucked me I pulled on his condom and started sucking his thick cock again. Like I said before sucking cock turns me on so much, and I came almost immediately right down his throat. Without a word I got up, got dressed and left.

It was so hot I jacked off twice when I got home. And I knew I would have to meet him again before I moved.