This is my second submission to Nifty. My first submission is here: https://www.nifty.org/nifty/gay/encounters/figuring-out-my-role
I was mostly proud of that story, but the actual sex description is kind of lacking due to me (shamefully) never have been actually fucked before. It's tough to really describe something you've never really experienced.
Here's how I want my first time to go. -----------------------------------------------------
It was time. I'd finally made the decision. For as long as I can remember, I've been putting things in my ass to get off. First it was a finger, then 2, then 3. Next, I moved on to things that were vaguely penis shaped, but that wasn't particularly satisfying (and it was dangerous.) Eventually, I got my first dildo. It was one modeled after the black cocks that I have lusted after for years. I still remember lubing it and trying to force it in. It hurt like hell...at first. After a minute or two though, it felt awesome. As I used it day after day, I started really looking forward to having time alone to jerk off with it in my ass. Since I looked forward to having that dildo in my ass so much, I figured it was time to try the real thing. I wanted someone to fuck me.
My taste in men has always been pretty consistent. I liked looking at pictures of black guys, with big muscles and bigger dicks. I'm 6'2", 210, and my ideal man is big enough to "man handle" me (pun intended.) I figured the easiest way to find someone that matches that description was on Adam4Adam and I created a profile listing exactly what I wanted: a big, black dick to fuck me. Over the course of a few days, I started messaging various members of the site. Though I did my initial searching based on physical traits, I wanted to find someone who understood what I was looking for to be the one who actually got to pop my cherry.
After some back and forth with a few different guys, I narrowed my selection to Jason. He was 235 lbs of 6'3" tall muscle and had an 8" cock that made me salivate just thinking about it. He also was pleasant in his messages and respected that I had some minor anxiety about how this whole thing would go down. After a little more back and forth, we settled on an upcoming Saturday night for when he would finally give me what I wanted.
When Saturday night came around, I started going through the plan that Jason and I discussed. First, I checked into the hotel room that I had chosen to be the location for my first time. I made sure the room was well stocked with condoms and lube for what was to come. I then made my way to the nearby coffee shop where I was to meet Jason and verify he was an actual person before giving him the room number. I felt my ass twitch as I walked in and saw Jason sitting against the back wall. He was wearing a tight, black shirt that barely hid his muscles and he flashed a smile when he saw me that made me want to bend over for him right there.
"Hey" he said as I approached. "How's it going?"
"Good" I managed to stumble out.
"How's the day going? You catch the game this afternoon?"
"Yeah. I got bits of it, here and there, in between errands." The conversation continued like this for a few minutes until I felt a little more at ease. Once I felt comfortable with him (which really didn't take that long), I told I'd catch him later and slid a hotel key listing a room number across the table as I left.
When I got back to the hotel room, I--as we had talked about--stripped down to just a pair of gym shorts. I wanted minimal amounts of clothes to get in the way of what was about to happen. After a few minutes of waiting, I heard a key in the door and Jason walked in. As we had planned, he didn't say a word, but immediately began taking off his clothes. His body was even more impressive in person and I started to get hard just looking at him. He moved into the center of the room and started stroking his dick. With each stroke it grew longer and harder. After years of looking at pictures of dicks like this on the internet, seeing the real thing made me salivate. It was time.
I got down on my knees in front of Jason and kissed his balls. I licked my way up his shaft. After teasing him for a few seconds, I finally put my mouth around his shaft. The sensation of Jason in my mouth was incredible. The skin of his dick was both soft, but unyielding. The more I sucked, the harder he got and the more I wanted to please him. He grabbed the back of my head and started moving me back and forth on his cock as he moaned. I tried my best to get all of him in my month, but my inexperience betrayed me. Even though I'm sure I gagged more than he would have liked Jason continued to moan as I did my best to please him.
Without saying anything, Jason pulled me off his pulsing dick and directed me to the bed. I laid down on the bed and Jason pulled off my shorts. He took my dick in his mouth and started working rubbing his hands all over my body. When I tried to move, even slightly, he forcefully held me in place to show me that I was his. I couldn't have been more turned on. At one point, as he was licking my balls, Jason move closer to my ass. At first, I felt his tongue around my hole, then in my ass. The feeling was strange at first, but as he continued to tongue fuck me, it started to feel amazing. When I started moaning and bucking on the bed, Jason began working his way back up to my dick. As he took me in his mouth again, I felt a lubed finger slowly enter my ass. I moaned. He began working my cock and ass at the same time. Before long it was two fingers, and then three. I wasn't sure how much of it I could take.
"You're ready," Jason said. And I was. Jason grabbed one of the condoms from the bed side table and put it on. He lubed up his dick, and put some more lube on my now heavily lubed ass. He grabbed me by the legs, put his dick at the entrance to my ass, and smiled at me. Shit. I wanted this guy to fuck me so bad.
"Be slow" I said. Jason smirked and started slowly entering me. It felt weird at first, not being in control of what was entering my ass. I let out a moan as he pushed in further and pain flashed through my body as he continued to push into me. I started to wince.
"It's okay, it'll be okay" he said, pulling me harder and continuing to push that 8" cock deep inside me. I looked down when I felt his thighs resting on me. He was in.
"Fuck," I said, not fully adjusted to having him inside me. At first, he just stayed there, pulsing inside me, then he started slowly pulling out and pushing back in. As he continued to move, and I continued to relax, the pain went away. In his place, I felt more pleasure than I ever had before. I had jerked off with a dildo in my ass more times than I could count, but this took things to a different level. Jason's hard dick inside me as he thrusted, over and over, holding my legs tightly to give him the access he wanted. It was overwhelming. I started moaning, shaking, and writhing on the bed. How had I waited so long to experience this?
"God. You feel so good." Jason said. I looked up to see his muscles flexing and a bead of sweat rolling down his forehead. Jason continued to fuck me, changing between long, slow thrusts and harder, faster ones. Just as I was thinking I couldn't handle any more pleasure, Jason pulled out and forcefully turned me over. I was left kneeling on the bed and I raised my ass in the air, begging for him to re-enter. It didn't take him long to oblige. This time, there was no pain. Just pure ecstasy as he entered me from behind.
"Fuck,yes" he said as grabbed my hips and pulled me toward him. "Are you sure this is your first time, because this is amazing." I could only moan in response and push my ass back along his dick. Like before, we started slow. Moving in and out as I got used to him inside me in this new position. It didn't take long, however, before things picked up. I met him half away as he thrust into me, harder, faster.
"Yes, god. Fuck, yes. Fuck me. Fuck me!" I screamed. I had lost control. All I wanted, all I could think about, was Jason fucking my ass and I never wanted it to stop. I moaned and shook. I buried my face in the sheets as my body twisted and contorted in pleasure like I had never felt before. At some point Jason had started spanking my ass (I had been too wrapped up in everything else to notice) and the burning pain from his slaps, combined with his dick buried in me was overwhelming. I have no idea how long this continued, since I had lost track of time long before. Eventually, Jason reached down and started stroking my dick as he fucked me. I couldn't take anymore and I blew cum all over the bed as my whole body orgasmed. Judging from Jason's reaction, this had been by design, as my orgasm also pushed him over the edge and I felt his cock pulsing and twitching in my ass as he left out a loud moan.
When Jason pulled out, I collapsed on the bed. I was covered in sweat and my ass burned. My dick was still leaking semen everywhere. I didn't know if I ever wanted to move again. When I rolled over, Jason was standing there. Sweat glistening off his muscles. Smiling.
"Let's do this again." he said.
"Yes," I responded. "Let's."