Craigslist Hook Up

This is a fiction story involving unprotected sex. The author does not condone unprotected sex. Please be safe.

***

It was a typical gloomy March day, with time to kill before I went to work at my second-shift job. I looked around my small 4 room apartment, and sighed. I had clothes, my phone, a few kitchen things, and a mattress to sleep on. Not much, but it would do, and it was on the ground floor at least. My ex had announced that he wasn't ready for a committed relationship, and I had to move out and find another place. A co-worker had steered me to this apartment building, and I got lucky, this unit was available. The rent was income adjusted, so I could get by, just. Giving another sigh, I stretched out on the mattress, and pondered my situation. My ex and I had a great 3 months together, I had thought. We had similar tastes in music, movies, etc, always had a lot to talk about, and the sex had been very good. After a week, we'd agreed to throw away the condoms, got tested, and proceeded to have sex at least 4-5 times a week. I was really into him, and thought he felt the same way. But then he dropped the bomb on me, and now I was alone. Out of suspicion, I used the last test kit before I left, with a negative result, so at least I didn't have that to worry about.

Picking up my phone, I checked my email, and then browsed around for several minutes, finally landing on Craigslist. I always enjoyed reading the posts, some were absolutely hilarious. I'd never made a posting myself, nor had I answered any, but as I scrolled through them, looking for the ones with attached pictures, it occurred to me that it might be fun to try. I was bored, nothing else to do, so why not? It took a few minutes to type in the information, deliberately changing my city and age, since I was not out, and didn't want to take a chance. I attached a picture of my 7" cock, and submitted the posting. About an hour later, I started to get emails with responses. Most were awful, big fat guys, guys were total bottoms, or just weirdos. I was beginning to think it was a waste of time, so I set my phone aside, and took a nap. A couple of hours later, I woke up, and looked at my phone. Seeing I had new mail, I hoped it wasn't a problem at work, but when I opened the mail app, I saw I had a new message from Craigslist. I opened it figuring it would be another loser, and saw it had 2 pictures attached. They were body shots, from the neck down, and very nice. The guy was nice and trim, flat belly, a good amount of hair, and had a short cock that was sticking straight up. The other picture was of his back, broad shoulders tapering down to a nice ass. I read his message with interest.

He was 10 years or so older than I, married, and had very little experience with men. It seemed there were a lot of middle aged married guys who get the urge to experiment with man sex, but this one interested me. He said he liked to make out, liked foreplay, and would both top and bottom if it got that far. We were very close to the same height and weight. I looked again at his pictures, and imagined having that nice body naked in my arms. It had been a while for me, and my cock stiffened as my mind played over the possibilities. I typed out a response, and gave him my email address, saying I was very interested, and would like to exchange face pictures. I hit send, and played a game on my phone for a few minutes until I heard the tone for new mail. It was from him, with an attachment. I opened it eagerly, and saw the picture was another full body picture, including his head and face. He was very good looking, dark hair with a somewhat craggy face, looking at the camera with a serious expression. I quickly took a full body picture of myself, and sent it to him, along with the message that he was a real hot guy. His response was very fast, and we shot messages back and forth for a few minutes, addressing each other's concerns about being clean, discrete, and sane. My mind was made up, I wanted to meet this guy, and I asked if he could meet today at my apartment. He said he would, in 30 minutes or so, and I used the time to shower and make sure my asshole was clean both inside and out. I decided that if we fucked, it would be bare, since he was married, and had only fucked once, but with a condom.

I pulled on a pair of sweat pants, and waited nervously for time to pass. When I heard the knock at the door, I hurried over to open it, and was pleased to see my new friend. I smiled, he was much better looking than his picture. I could tell he was nervous too, glancing furtively around the apartment. I put my hand on his arm, and told him that he was very handsome. This seemed to relax him, just a little, and we made some small talk. I was itching to get his clothes off, and so decided to break the ice by kissing him. He flinched, from surprise I think, then eagerly kissed me back. Wow, he was a good kisser, dueling tongues with me, and running his hands up and down my naked back. We stopped for air, and he looked down at the bulge in my pants. With a smile, he tugged at the drawstring, and slid the waistband down my hips, then took my cock in hand and stroked it gently. I liked what he was doing, but I wanted to do it on my mattress, so I took his hand and led him into the next room. I slipped out of my sweats, and watched him undress. His body was very nice, more lean than muscular, with his cock standing up just like it did in the picture. It was shorter than mine, 6 inches at most, but with a good girth.

We got down on the mattress, embracing and kissing each other. He felt good in my arms, chest pressed against mine, and our cocks rubbing together, and I ran my hand down to his ass. The cheeks were round and soft, with a deep cleft, and I pushed a finger between them to find his hole. He gave a big jerk and a moan when I touched it. He surprised me, pulling away from me, but then he leaned over and sucked my cock into his mouth. I lay back to let him do as he wanted. He was definitely inexperienced, but did a good job, giving me a wet sucking and licking. As he did, I reached around behind him, and fingered his asshole again, hoping he would let me fuck him. This time, he wiggled his ass, obviously liking what I was doing. We went on like this for a few minutes, until I could feel an orgasm building up, so I made him stop.

Now it was my turn. With my new partner on is back, I took his cock in hand, and gave the head a sucking kiss. This made him suck in his breath and hunch up, and I took most of his cock in. I wanted to give him a good sucking, but didn't want him to cum, so I while I worked on his cock, I found the tube of lubricant, and got some on and in my asshole with my free hand. Then I pulled off his cock, and squirted lube on the end, letting it run down, and smearing it around with my hand. He just lay there with wide eyes, watching me. I think he knew what I was doing, but he acted like he couldn't move. That was fine, I was planning to do all the work. I straddled his hips, reached behind me to find is cock, and lowered my self down on it. The head was pretty fat, so I had to push down to get it started, then it popped through and I had it in me all the way. I looked down at him, and almost laughed out loud, he looked terrified, I had obviously surprised him, and now he was committed. But I controlled my mirth, and began to ride him slowly. As much as I like to top, I like to get fucked too, and I definitely prefer smaller cocks. They are all fun, no pain, and the one inside my ass was perfect, filling me up just right, and just long enough to bump against my prostate.

My grip on his cock was getting to him, he was breathing hard with his eyes closed, and letting his hands roam all over my chest. I reached down and fingered his nipples, making him squirm under me. I wanted to make it last, but couldn't help myself, I had to go faster, so I bounced on him harder, my ass slapping his legs when I hit bottom each time. It didn't take long, he grimaced, and hunched up, lifting me up and pressing his cock into me, shooting his cum inside me. Then he slumped back down on the mattress, spent. I stayed on him, and leaned down to give him a long kiss, and told him he'd given me a good fucking. Then I whispered in his ear. "Do you want me to fuck you?"

"Yes." he said in a ragged voice.

"Okay, I'll get off you, and you turn over on your side." Once he was in position, I located the lube, and got his ass ready, then my cock. I snuggled up against his back, and slipping a hand between his legs, lifted the top one up to expose his asshole. "Hold your leg up like that." I said, and slid closer to him. I found his hole with the end of my cock, and gave a push. The head went in partway, and I heard him gasp, so I stopped. I could feel his anal ring twitch and contract, trying to expel the intruder, but I held my ground, and pushed again. This time, it went all the way in.

"Shit." he moaned.

"You okay?" I asked. I wanted to fuck him, but not force him.

"Yeah, give me a minute." I could feel his anal muscles contract and relax a few times, then he took a deep breath and let it out. "Okay, go ahead." Slowly, I pushed it in the rest of the way, until I was up against his ass cheeks. I stopped, and withdrew partway, then pushed all the way in him again. I had an arm around his chest, and I could feel his heart hammering away. I gave him some more slow strokes, and felt his hand slide over my hip, to clutch my ass, pulling me tighter against him. Now I knew he was ready. I started fucking him with quick shallow strokes, and it felt great. His ass was tight, gripping my cock and milking it. Horny as I was, it wasn't going to take long.

"Hey, can we do a different position?" he asked. I stopped, and looked over his shoulder at him.

"Sure, what do you want?"

"Um, can I get on my back, and wrap my legs around you, and you fuck me that way?" Wow, I liked the way this guy thought. I pulled out, and got up on my knees while he swiveled around and put a leg on each side of me. I leaned forward, and held my cock until I got it lined up, then pushed it in. This time, he moaned, and put his arms around me, pulling me down on him. I wrapped mine around his neck, and felt him cross his ankles behind me. Locked together, I fed my tongue into his mouth, and started fucking him.

"Aaah, fuck me, fuck me with your big cock." he breathed in my ear. I wasn't holding back now, giving it to him with long strokes, smacking against him on every downstroke. We clutched each other, hanging on as I pushed to the finish, breathing hard and grunting with effort. Another minute, and I drove into his tight ass as deep as I could, and felt the cum surge out of me, 3 big spurts, and a couple smaller ones. I shuddered, and relaxed my grip, letting my weight rest on his chest, while he caressed my back and kissed at my neck. When I felt like I could stand, I got up, and fetched some wipes for us.

"Wow." he said. "I didn't expect that, but I'm glad we did. it was amazing."

"Yeah, you looked shocked when I sat down on your cock."

"Oh shit, I didn't know what to do. Then it was in your ass, and all I could think about was how good it felt."

"You liked it when I fucked you?" I asked.

"It hurt real bad at first. But as we went along, it felt better, then when I was on my back it felt great. Best sex I've ever had."

"Good, it's supposed to feel good. Once you get stretched out, it will be a lot better."

After he left, I felt an odd letdown. I puzzled over my feelings the rest of the day and at work, and the next day when I woke up. It wasn't that he was older, I actually got off on that. Finally, I realized it was the fact he was married. It was never going to be any more than sex with him, and that bummed me out. I've always been an idealist, and that's often been my downfall in relationships. Now I was struggling with the fact I'd found a great guy, but couldn't have him to myself. Several days passed, and my self-induced misery slowly went away. Work was very busy, and I started to get some overtime, improving my finances and my outlook. When a day off came, I was lounging in a second hand recliner I'd bought, when my phone chirped, I had new mail. I almost ignored it, thinking it might be my supervisor, then decided I wasn't going to turn down overtime. I opened the app, and saw it was from the married guy. I paused, knowing what he was going to ask if we could hook up again. I thought back to the day he came here, and my cock stiffened as I recalled how good it felt to have him under me, my cock deep inside him. I opened his message: Hi, I'm free today. Want to get together? I smiled as my cock won the battle with the morose side of me, and I typed in return: Sure, I'd love to.

The End