I was walking home downtown late one Friday night, when I looked down a side street and saw Jesse and the cop. I decided to walk over and see what was going on.
Jesse was obviously drunk - talking too loudly, slurring, staggering a bit. The cop was unimpressed. I decided to intervene.
The cop wasn't all that impressed with me either, but he didn't really want to be bothered with Jesse, so he let me take him. This city was rough enough that an amiable drunk didn't count as a priority call. So I put my arm around Jesse's shoulder and half dragged him one more block to my building and then up the elevator into my apartment.
Now, I didn't have any bad intentions here, really I didn't. I put him on the couch, took his shoes off, covered him with a blanket, and pre-positioned a bucket, just in case. He passed out right away and I crawled into my own bed.
I was living temporarily for a couple of months in a furnished 1-bedroom apartment in a city strange to me. I was an IT contractor working at a manufacturing plant on a project. The money was good, but outside of work it was boring.
Jesse was one of the workers out on the floor at the plant. I had met him in the parking lot at quitting time a few days earlier, when he asked me to jump start his truck. It was a beat up old 4x4, covered in mud. His alternator must have died. I got him going again, we shook hands and I headed home without giving it a lot of thought, other than that he was kind of good looking, in a rugged, rough-around-the-edges way.
I woke up around 3 am to hear him yakking in the toilet, so I got up to check on him. He was okay, but was a stinking mess. He tried wiping the puke off his chin and chest hair with some toilet paper that kept disintegrating.
"Do you want to just take a shower?" I offered. "I'll get you a towel."
He apologized over and over again, the way drunks do. "I'm so sorry, man. It's all over your floor."
"I don't mind," I said. I got him a towel and went to wait on a chair in the living room while he showered. I closed my eyes until I heard the water stop.
"Do you live alone?" Jesse asked as he re-entered the living room with just a towel wrapped around his waist.
"Yeah, I'm single."
"I thought you had a boyfriend?" he asked. Jesse sat on the couch where he had been sleeping.
"Nah, just dating." I had tried going on a couple of dates with some guy at the same plant that I had met on Grindr, but he was too weird for me. "How did you know that?"
"I heard it at work. My sister is in accounting in the front office."
"Small world. I only met up with that guy twice. What else did she say?"
"Not much. She thinks that guy you dated is weird, though, so don't sweat it."
I laughed.
"Thanks for keeping me out of jail and letting me stay. I'm really sorry about all this." He seemed to have sobered up some.
"No worries." I stood up and got us each a glass of water.
"Goodnight," I said as turned out the lights. I went to my bedroom but left the door ajar. I got in bed to go to back to sleep.
Twenty minutes later, Jesse climbed into bed with me. I rolled over towards him and we naturally started to spoon. My hand slid down his front to check for a boner through the fabric of his boxer briefs, yup.
He pulled off his underwear and I sucked him for a bit. Then he repositioned to suck me and we 69'd for a bit. I stuck my finger in his ass, which he didn't mind at all, and a few minutes of that made him cum. I finished myself as he lay there panting and I blew my load on his chest.
We went back to spooning and fell asleep.
In the morning, we groggily woke up at more or less the same time.
"You really know how to look after a guy."
"You can come visit whenever."
"I want to cum again right now."
I felt his cock, which was already hard. We did again exactly what we had done a few hours before, but I went a little slower to make it last a little longer.
I offered to make him breakfast but he declined, claiming he had to go. We did, however, exchange cell numbers before he left.
Two days later, he texted me around 9 pm and asked if he can come over. Of course I said yes.
I opened the door when he knocked. He was dressed in his high school football jacket. It was dark purple with white leather arms. His hands were jammed in his pockets and he had his head cocked to one side and a sheepish grin on his face.
"Get in here," I said with a smile.
He stepped in and kicked off his sneakers.
I felt his crotch through his jeans. He was already hard. "I know what you came here for."
"Yeah," he said heavily. "I need it bad."
We pulled off our clothes without waiting, right there by the door. I got on my knees and sucked him while he leaned back against the wall. He was freshly showered for the visit. I licked his sack and sucked his nuts in my mouth one by one.
"Let's go to the bedroom," he said.
He led the way and I followed. But when he climbed up on the bed, he got on his elbows and knees and presented his ass, burying his head in the pillow. "I've always wanted to try this. I need to know what it feels like."
I was surprised, but I wasn't going to say no. I ran my finger down his crack, rubbing his hole. He wanted it all right. I rimmed him and he moaned like crazy, first in surprise and then because he liked it.
"Fuck me. Please."
I got some lube from my nightstand and started applying it first to his hole and then to my cock. I wasn't going to bother with a condom with a virgin.
The first entry was painful for him, but he didn't complain or ask me to stop. I pulled out to give him a break and then pushed back in a few times. Eventually, he opened up and I was all the way in. He was breathing hard but okay. His hole was tight and gripping my cock hard.
I fucked him slowly at first but then the need to cum overtook me and I fucked him hard. He whimpered but I didn't care. Then it hit me and I just held his hips close while I shot my load into him, over and over again. When I was done, I reached around. His cock had gone soft but sprang back to life when I stroked him. I made him cum without pulling out. I wanted him to orgasm with my cock still inside him.
After he shot his load all over the bed, I pulled out and we collapsed on the bed together. He shoved right up against me to avoid the puddle of cold cum. We just lay on our backs, recovering, with our legs touching. Neither of us spoke.
Finally, Jesse broke the silence, still staring at the ceiling. "That hurt more than I was expecting."
"Sorry, I was trying to break you in easy."
"It's okay." He turned his head to look me in the eye. "Does it get easier?"
"Definitely, with practice."
"I'm gonna need you to do that to me again. I've never had an orgasm like that in my life."
I leaned over and kissed him, open mouth. He was caught by surprise but gave in to it. We made out for a few minutes and then I lay back and pulled him to me and we cuddled.
He was over pretty regularly after that.