Please visit my profile to get caught up on Chapter 1. Each chapter is based on a real story with only names altered.

It had been a little over a month since my first Craigslist encounter. I couldn’t believe he was a complete stranger and I’d let him fuck me. I was of course nervous and got myself checked out but once I knew I was all clear, the flood gates were open. I was busy preparing for finals and didn’t have time to go out. With no real action male or female, I was spending more time watching porn. It started by looking up anonymous encounter videos daily and soon I was only cumming to the idea of having random men use me.

I knew I’d be leaving to go home to my small hometown within a few weeks and I didn’t think the chance of getting cock back home would be high. I decided if I was going to fit it into my schedule I’d have to try Craigslist again when I had a few hours here and there. I messaged a few people who had posted but nothing really manifested. Over the next few days I tried a few times to connect with someone with no luck. I was so turned on by the idea of getting used again, I was starting to get a little desperate. After the fourth day of no luck messaging someone I decided it was time to post again. It was a Friday night, I figured someone would come get a 19 year old to fuck.

The biggest issue for me was that I would need to be picked up at my dorm and go to someone’s place. My roommate was holed up in our room studying for finals and I didn’t understand the bus routes yet. I made a post along the lines of “19M, 170lbs, 6ft, looking for a guy or two to blow and maybe fuck. Will need to be picked up. Please have condoms and lube.” I attached a picture of my cock and ass and hit post.

I received what must have been 15 messages in the first 20 minutes but no one was able to come get me. Even though nothing was working out, half of the fun was reading messages from dudes who wanted to fuck me. It was such a turn on knowing the cocks were local and I could potentially run into them and never know. I was edging and about ready to just say fuck it and cum to a rather large cock who couldn’t host, when I got an email.

“Hey man, 34, 190lbs, 5”c, bi guy here, I’ve got a gay buddy who would love to fuck you with me. He can pick up lube and condoms, I’ll pick up you. You down?” Attached was a photo of a smaller white cock but nothing to complain about.

At this point I was so aroused anything that seemed somewhat safe would have done. There was a brief back and forth where he was very open about his recent test, he agreed to condoms as he didn’t know his buddies status and seemed pretty normal for what we were about to do. On his second reply he asked if I was ready to get fucked and I responded back yes and told him where to pick me up. He was about 20 minutes away. I got myself ready and waited for his message that he’d arrived.

I paced my dorm, anxiously waiting for his message. Finally, my phone buzzed.

“Here, black car, lights on”

I made my way down to the parking lot and looked around. He had parked under one of the yellow street lamps which did nothing but illuminate how beat up his car was. The exhaust rattled to a point that I was worried it would start to draw attention. The lot he was in was dark with only one other light. My heart was pounding and I decided if I got any weird vibes I would go back inside. I tried to act casual walking over to the car door. His window was rolled down and he quietly introduced himself as Tyler. He was sporting an unkempt goatee but looked like a normal enough guy. He gave off a bartender vibe that was friendly and disarming. He was exactly what he described and I felt at ease with his demeanor. Easing up a little I got in the car and we took off.

He skipped through the small talk to make sure I was comfortable enough but as we turned onto the highway he got right into it. “My buddy said he would be a little late but we could get started without him. I’ve been tested but will wait for condoms. If I can’t fuck you yet that doesn’t mean I can’t get my mouth on your cock or vice versa.” He winked. “Have you ever been with two dudes before?”

“No, honestly I’ve only had a few experiences. I’ve enjoyed experimenting but I’m really just interested in the sexual acts and not the men. I’ll end up marrying a woman someday but I figure college is the time to try new things.” I replied.

Tyler glanced at me and said “Not to be blunt but if you’re at the point of wanting to fuck two dudes there’s no going back. You’re always going to want cock. Even if you marry a woman, someday you’ll wake up and want one in your mouth again. Trust me, as a bi guy, it doesn’t go away.”

His words stuck with me and I thought on them quietly as he drove. He smirked when I didn’t have a response but he didn’t follow up.

I was still new to the city so I wasn’t entirely familiar with where he was taking me. As I looked out the window everything started to get a bit sketchier. He pulled off the side street we were on into an apartment complex. The building was in rough shape with overgrown landscaping everywhere. Liquor bottles and cigarette butts were overflowing the garbage in front of the entrance. He pushed a button and a door I hadn’t noticed opened to reveal a parking garage straight out of a murder film.

My heart began to race again as I had a sinking feeling I was just in for the ride at this point. He wasn’t going to just turn around and take me home. To cope, I decided to trust my initial gauge of him that he was just in a low paying profession and could use a good nut.

As we went underground the car jostled over uneven, busted concrete floors. He pulled into a space next to pillars that looked like they could collapse at any second. Chipping concrete was littered everywhere and there were only three other equally beat up cars down there.

“I know it ain’t much but hopefully that won’t matter in a few” he said as he got out and lead me to the door. I still felt comfortable enough but the apartment building I found myself in did nothing to enhance the mood. Luckily, there was no one else around and we had an uneventful trip to his apartment.

He walked in first and turned on a small lamp on the island between the kitchen and living space. The apartment was not much better than the rest of the building. A small studio made even smaller by the fact that he clearly didn’t feel a need to clean for the occasion. The view of the skyline out the window told me I was in a part of town that even I knew I didn’t want to be in. I pushed that out of my mind for the moment and decided I’d come this far and was again just along for the ride.

There was a futon bed pulled out in the middle of the room with piles of clothes and junk laid out around it. There were no blankets or pillows on the futon but at least the sheets looked clean.

“I need to take a shower before we start and my buddy will be a few minutes. Want to join me?” Tyler asked.

I nodded and followed him to the bathroom. He pulled his shirt over his slight beer belly leaving him in just his boxers. His cock was already rock hard and poking through the hole in his underwear. His photo did it justice. It was on the small side of 5” and had a sharp curve up but was thicker than I expected. He winked at me as he took his boxers off and stepped into the water. I got undressed and gave him a little show pulling my pants down. From the edge of the tub I reached into the shower and began stroking his cock. It began to stiffen even more in my hand and I could tell he wanted to get started.

I got into the shower and leaned down as best I could and took him into my mouth. I slowly wrapped my tongue around the tip as I massaged his balls. Water poured down my face and so I just closed my eyes and sucked. After a brief time he pulled my head to get me to stand and turned me around. He rubbed his hands all over my body, stopping to pinch my nipples and rub my balls in the warm water. He started stroking my cock while his other hand slid back and found my hole. I moaned in pleasure as my cock fully hardened in his hand. He teased me with a finger for a minute causing me to squirm in his hands. I felt him pull me close and his cock started rubbing against my ass, sliding between my cheeks. This snapped me back into reality and I turned around and said “Let’s dry off. Where is your buddy at?” he grunted in agreement and said “Let me call him.”

He only had one dry towel in the bathroom that he gave to me. He left me to dry off and went to grab one from the other room. I hung up the towel and stepped out in the main room. Tyler was in the kitchen with a towel around his waist on the phone. “Yeah, when do you think you’ll be here?” “Okay. Okay. Okay.” He hung up. “My buddy said the store he went to didn’t have any condoms so he’s going to another and then will be on his way. It could be another 30 minutes. The good news, as I said, I was just tested and I don’t play often.”

“Okay, we can definitely keep going but still want to wait for the condoms before fucking.”

“Ugh you fucking tease, fine. If you tease me I get to tease you though slut.” He said.

At this point I was ready to just keep playing with Tyler and wait. I didn’t think I had much of a choice. It was clear he would fuck me the moment I said okay so it was best to keep him occupied. I moved over to the futon and he waisted no time dropping his towel and making his way over.

I met him with mouth open. He slapped my face with his cock once or twice before sliding it into my open mouth. He pushed forward into my throat and roughly thrusted. The sharp angle made me gag and pull off but I quickly dove back on. I bobbed on his cock for a few minutes before he grabbed my head and started fucking my face. After he got a few good thrusts in he pulled away and told me to lay back.

He grabbed my legs and pulled me to the edge of the futon. He kneeled down and took my cock straight into his throat. I cried out in pleasure. After a few times feeling his chin press into my balls I was the horniest I had ever been. He stopped his inhalation of my cock and lifted my legs into the air. He massaged my balls before he sucked them into his mouth. I moaned and he responded by collecting his saliva with a finger and started swirling it around my hole. My mind started to go blank from pleasure as he stroked my cock, tickled my hole and tongued my balls. I felt an orgasm begin to build that he sensed. He stopped and stood and grabbed lube from the side table.

He squirted it onto my cock and started to stroke me again. With his other hand I felt him line up his cock with my hole and I said “whoa whoa, this is so hot but condoms.” He said “I know, I told you if you’re going to tease me, I’m going to tease you. I won’t stick it in.”

I sighed but let him do it. He lined back up with my hole and started stroking my cock again. The combination sent a fire burning in my gut and feeling his tip at my hole I desperately wanted him to slide in. It took everything I had to refrain from letting him pound my brains out. He would lean slightly forward putting the slightest pressure into me until I’d whimper in disapproval and he’d back off. With each push I felt my willpower weakening. I had never felt hornier as this older guy I just met was a cough away from being in me. I wanted nothing more than for him to just say fuck it and push harder but I kept my mouth shut.

He felt my cock stiffen in his hand and he could tell I was losing resolve. Taking his opportunity he took his other hand off his cock and grabbed my foot. I didn’t register what he was doing until he pulled it to his face and put my toes into his mouth. This had never been and still isn’t a kink of mine but the feeling caught me by surprise and was so erotic I couldn’t help but be overcome. He swirled his tongue between them causing me to moan and push back onto his cock. Tyler taking that as consent gave a thrust and with no resistance was balls deep in me.

I was so lost in the sensation of him slipping in and starting to fuck me, I didn’t fully comprehend what was happening. He was still stroking my cock and it only took a minute before I felt an orgasm building in me. I opened my eyes and simply watched as this complete stranger fucked my ass raw. It was such an incredible feeling I started to cum almost immediately. My load shot out over his hand onto my stomach in ropes. He slowed his fucking and in a moment of clarity I had him pull out.

“Fuck, that was sneaky. Fucking hot but sneaky. I thought we said condoms.”

“Sorry dude, you pushed back and that ass is so sexy I couldn’t help myself. Clearly you liked it.” Tyler responded. “If it helps I was tested and I didn’t cum”

“Alright alright, whatever. Is your buddy going to make it or not?”

He called him back and it quickly became apparent his friend was not coming. Tyler hung up and turned to me. “Sorry dude, I can drive you home if you want. At least you got to cum. Any shot you’d blow me?” At this point I was getting horny again so I said “sure, go shower”

He quickly cleaned himself up from our round one as I laid on the futon. He came out of the bathroom and I sat up on the edge like the first time. After cumming I had lost some enthusiasm but without saying anything I took his cock into my mouth. I blew him for a few minutes but I couldn’t help but think of his cock in my ass. It had felt so good and he was adamant about being clean. His cock was getting me worked up again and he didn’t appear to be cumming any time soon. I made a decision and didn’t look back. I pulled off his cock and laid down in the same position as earlier. I pulled my legs back behind my head and told him. “Don’t cum in me.”

His eyes lit up and he waisted no time grabbing the lube again. He lined his cock back up and with no ceremony slid in. He started slow but was soon fucking my ass with a fierce tempo. I moaned like a whore as he hit the spot over and over again. He pounded me for what felt like ten minutes and I started to feel a second orgasm build. I didn’t get the chance to see that through though as Tyler started to slow down and grunt. He pulled out and began furiously stroking his cock. It only took a second for him to shout and begin to cum. I felt a warmth cover my torso as shot after shot sprayed onto me. Instead of ropes his cum was shot out in hundreds of droplets. The volume was huge and he even managed to get quite a bit on my face.

I laid there covered in his cum as he caught his breath. He handed me my towel from earlier and I got myself cleaned up as best I could.

He finally broke the silence and said “Thanks man, I promise you’ve got nothing to worry about. That was super hot.”

He gave me a ride home. After he dropped me off I jerked off again thinking of him fucking me raw. Two weeks later I got myself tested and went home for the summer where the fun will continue in Chapter 3.