In the early 2000s I met several guys on Craigslist m4m message board. I saw one guy mid 20s white, 5’10”, 150 lbs, vers who lived downtown, so I hit him up since I lived downtown as well. We emailed back and forth a few times and he eventually invited me over to his place. I guess I was more adventurous back then because we didn’t even exchange photos. I went over to his apartment in the afternoon and he buzzed me in. I knocked on his door and he opened it. He was a cute blonde, wore glasses (definitely a turn on for me), and had on a black tank top, jeans, and running shoes. 
“Am I okay?” I asked him, “I can leave if you want.”

”No, you’re cute,” he told me, “come in.”

I followed him inside and he gave me a quick tour of his 1 bedroom apartment. He had a cute little patio and we chatted out there a bit before moving inside to his couch. We hadn’t explicitly talked about having sex, but I was getting good vibes, so when we had a lull in the conversation I pulled his head to me and kissed him. Our tongues dueled for a couple minutes until he pulled my shirt off me. I returned the favor and resumed kissing him, eventually going down his neck and chest to his nipples as I removed my shoes and socks.

I knelt down in front of him and took off his shoes and socks, and then unbuttoned his jeans and pulled them down along with his underwear, revealing a curved cut 6 inch cock. I stripped him completely then stood up to remove my jeans and boxer briefs. I just stepped out of my clothes when he leaned forward and took my own 6 inch circumcised dick into his mouth, slowly sucking up and down. After about a minute he stood up and led me into his bedroom and pushed me down on the bed on my back. He go on the bed and flipped around so we could 69. I took his cock into my mouth and he took mine into his and we had a languid mutual blowjob session for about 10 minutes.

He pulled off me and flipped around to lay beside me.

“I don’t have a condom,” he told me.

”Oh,” I replied. “You should’ve said something. I could’ve brought one.” He took my cock in his hand and started stroking me. I grabbed his and started stroking him as well. His spit from the blowjob dried up pretty quickly so I asked him if he had lube, and he grabbed a bottle out of his bedside table and squirted it on both our cocks. We kissed some more as we lay side by side slowly stroking each other. After a couple minutes he pulled me over on top of him, my legs going in between his and sliding them apart slightly. 

Our lubed cocks slid against each other as I started to grind on him. His kissing got more intense and his arms were pulling on my back. My arms were wrapped around him as I thrust against him. His hips were grinding up on me as well and eventually as we both pulled back away from each other during our thrusting, my rock hard cock dropped underneath him and started sliding along his ass crack. Every once in a while I would pull back enough so the head of my dick made contact with his hole. He was squirming so much beneath me I couldn’t tell if he was pulling away from me when that happened. 
I was so horny at this point and just wanted to drive my raw cock in his hole, but we hadn’t talked at all about fucking, other than him letting me know he didn’t have a condom. I decided to test my luck so I wrapped my hand around my dick and placed my fist at his hole so when I thrust through my hand the head pushed against it. Each time I did that it seemed to get a reaction out of him but I couldn’t tell if he was into it. We were still passionately kissing so the only noises he was making were some moans. I thrust again and felt the lubed tip of my cock start to spread his hole. His tongue was deep in my mouth and his arms were wrapped around my body. I thrust a few more times, his hole spreading more and more. Finally I felt his sphincter give way and the head of my uncovered cock sank into him, my fist keeping the rest from going the rest of the way in.

He arched his back up, thrusting his hips against me, kissing me harder and his arms pulling my chest closer to him. I let go of my cock and wrapped my arms around him as his legs came up and wrapped around my back. My bareback cock sank balls deep into him. He broke off our kiss and threw his head back. 
“Oh fuck!” He cried.  
“Are you okay?” I asked slowly starting to pull out. 
“Yeah,” he replied, “I’ve never fucked without a condom before, it feels awesome.”

”We can stop if you want,” I told him. 
“No,” he said, “you can keep going. I’ve been wanting to do this for a while now but couldn’t find anyone who was willing. Everyone always uses a condom.”

“Do you want me to pull out before I cum?” I asked him.

“No,” he said, “I wanna feel you shoot in me.”

He grabbed the back of my head and pulled me into another passionate kiss. I started fucking him like crazy, so turned on that this cute twink was willing to take my cock bareback and wanted my load spilling into his unprotected ass.  My uncovered dick slammed in and out of him as he thrust back against me, his legs and arms pulling at me trying to get me deeper into him. After a few minutes of me railing him he eased up a bit and grabbed his cock and started furiously jerking off. My own orgasm was slowly building, driven by the fact that my semen would soon be flooding this ass for the first time. I felt myself go over the edge, the orgasm ripping through my entire body as jets of cum streamed out of my cock into him. His own cock started spraying at almost the same time, sending cum up into his chest and face and even the headboard behind him. I collapsed down on to his cum soaked chest, my raw dick still buried inside him. I kissed his lips and started licking the cum off his face before pulling my cock out of him and laying down beside him. 
“Fuck,” he said, “feels like I lost my virginity again.” 
“Thanks for letting me be the one to do it,” I said. We kissed again and we lay there for a bit until I said I had to go. I got dressed and kissed him and left. 
 

A few days later I called him and asked if he wanted to hook up again. He agreed, so I got cleaned out and lubed up my hole before heading over. He buzzed me up and when I knocked he opened up the door and when I walked in, I saw that he was completely naked and his cock was already hard. I followed him to the bedroom and quickly stripped as he lay down on his back on the bed. I straddled him, my ass pressing down on his cock. 
“You taken a load bareback, you wanna give one?” I asked him. 
“Only if you’re cool with it,” he replied. In response I lifted up and grabbed his cock and placed the head at my already prepared hole. I slowly slid my ass down the length of it and started riding it. 
“Fuck, I’m not gonna last long,” he said after about thirty seconds. 
“How long is not long?” I asked. He grabbed my hips and gave three quick thrusts and moaned, and I knew he was breeding my unprotected hole. 
“That long,” he said, “sorry.”

“Don’t apologize,” I told him, “that’s all I want when I bottom. An ass loaded with cum and a satisfied top.” I pulled off him and lay down next to him. 
“Thanks,” he said, “if you wanna get off you can fuck me.” Five minutes later I dumped another load in his ass.