Barebacking - My first experience

Here I am, twenty-one years old, on my couch in my apartment wearing just a towel. The man sitting by me, Mike, a thirty-seven year old who I met online just a few hours earlier. He is fully dressed. He opens my towel and starts playing with my freshly shaved cock. How did I end up in this situation?

Go back just a few weeks earlier. My girlfriend and I had broken up. She moved out of our apartment and went back to her home state. Probably because her ex boyfriend lived in the same town as her folks did. I was alone and horny. The internet was a steady supply of porn to jerk off too and have sexually explicit conversations with other people. I was very niece when it came to chatting online. I had given out my phone number, sent nude pictures of myself, and even gave my address too. Most people online were just pretending to be someone else. I am sure that most women online I chatted with back then were probably men. Still I played along.

I had gotten into gay porn and it got me very aroused and my ejaculations were pretty impressive. I was mostly fascinated by the guys who liked getting fucked in the ass. I wanted to know how it felt. So days later I went to a local porn shop and bought a dildo and lube. It was a double dong, twelve inches, with a cock head on each end. I also stopped by a store and bought a couple enemas. A few guys I had chatted with suggested it for cleaner play. I also bought some anal beads to break me in.

The anal beads were amazing. I pushed them in one at a time while I sat over a towel naked. I was on my knees and pushed the first bead in. My ass stretched then the bead just popped inside me. I used plenty of lube on the beads and prelubed my ass sticking my fingers in me. I was extremely nervous wondering if the string that held the anal beads together would hold. When I got to the last bead, which was the fifth, I was surpriisd how they fit inside me so well. It was an odd sensation of having something go up inside me instead of pushing out. I was jerking off to a porn I had in my VHS player in my living room in the middle of the day. When I got close to shooting my wad, I slowly pulled the first bead out. As the second bead was cresting out of my ass, I exploded!! I had never shot so far. My cum hitting the wall over the TV! I moaned louder than I ever had. As continued to extract the beads, I shot another smaller load and another. My whole body quivered and the sensation of the bead being pulled and pushed out of my ass was exhilarating!

Hours later, I was jerking off in my living room again. I was naked on a towel. This time I was on my back with my legs open. I was desperate to try the dildo. I got into the mood by testing my oral skills on it. I found out, I needed lots more practice when I almost made myself throw up. Still, that did not detour me from going on. My cock was hard as I stuffed two fingers heavily lubed into my ass. I tried to pry myself open but I was so tight. I looked at this long thick dildo I had bought and wondered if I could even get it in. With so much lube on my hands, the dildo was slippery. I pushed it in. My ass involuntarily pushed it out. My ass put up a good fight pushing back on me trying to advance the dildo in. If I wanted the dildo to stay in I needed to push it in further. I am sure I looked like a fool, I had my legs up and open, I had both hands on the dildo reaching down between my legs. I plunged the dildo in hard and stuffed maybe three or four inches into me. I let out this loud "Unggggh!!" It felt huge inside me. I groaned as my ass puckered while it was being stretched open. I groaned and started masturbating furiously. I had one hand on the dildo keeping it in. My body tried to push it out but it was too deep. I thought it would stay inside me so I rubbed my cock with one hand and massaged my ball sack with the other. I was breathing heavy. In my excitement, the dildo started to slide out of me. I had to keep one hand on it. I stuffed it in deeper and it was amazing! I really enjoyed having it in my ass plus my erection seemed much stronger. The veins in my cock were showing, my extra thick cock looked bigger. It didn't take long to get me to climax. I rotated myself and put my legs up on my couch. I was on my back on the floor. I aimed my cock at my face and opened my mouth. My ass clenched and I grunted hard pushing the cock out of me as my whole body started shaking. I released my load hard. The first went straight into my eyes. I was blinded but kept jerking hard as the dildo was nearly pushed out of me. The second landed up my nose and partially in my mouth. It tasted bitter. The last good load hit my mouth and chin. I closed my mouth and swallowed hard. My cock still throbbing and let the last of my seeds go as the dildo was pushed out at last. My cum filled my bellybutton and I rubbed the excess out onto my abdomen. I laid there in a daze. The anal stimulation was incredible. I felt relaxed and exhausted.

I finally got up and took the dildo into the shower with me. I washed myself up particularly my ass and cock, then the dildo for the next time. I began to wonder what a really cock might feel like. Unknowingly just days away from my first experience. Enter Mike!

I met Mike through a local Yahoo m4m chatroom. He was one of the first guys who actually lived within thirty minutes of me. Mike was in a relationship with another guy. Mike was a top, and his partner was versatile. He told me they were in an open relationship and he liked fucking college aged boys. I was a little top old compared to most college guys he had hooked up with but when he saw my nude picture of me..he made an exception. Mike exchanged a nude pic of him from the neck down. He was in good shape, and had a very nice slender cock. I was a bit intimidated because his was an inch longer than mine. We chatted about meeting around 11:15pm. Mike did have some requirements. First he liked guys to be completely shaved.cock and balls. I wasn't very hairy down there and had no problem with it. The next was no condoms. I was a bit apprehensive but I understood it felt better. The last one seemed odd but Mike insisted I greet him at my door wearing just a towel. He went on to explain some guys chicken out and this was a way of showing how serious I was. I agreed to his terms and just forty minutes later, Mike was in his way. I rushed to the bathroom and gave myself an enema.

I held the fluid in as long as I could then expelled the contents in a pissing from my ass fashion. It was very painful how my ass kept pushing even when it had been emptied. I jumped into the shower and shaved my pubic hair off. I nicked my balls and the water stung when it hit the spot. I got out and dried off quickly. I took a few ibuprofen for the pain, Mike had warned it could be painful my first time. I changed from a wet towel around my waist to a dry one and began pacing nervously in my small apartment. I was just minutes away from meeting Mike. Unsure what he looked like and just going off a body pic he had sent me. I had a phase while pacing where I got scared. I thought about chickening out on Mike by turning off all the lights and hiding in my bedroom. I was very close as horrible images began to pop in my head. By then it was too late, I saw a car pull into my parking lot just below my second floor window at 12:25am. My curtains were open and I am sure Mike could see me as he exited his car. He took one long drag of his cigarette and flicked the rest away. He walked slowly toward my building as he exhaled the smoke in his lungs. I heard his footsteps coming up the staircase. My heart wee racing when he lightly knocked on my door. I opened it just as my neighbor across from opened her door. She saw me in just a towel and this strange tall slender man in the hallway. She gave me a weird look and quickly shut the door. I was shaking so badly when Mike stepped in. I locked the door behind him. I shook Mike's hand and introduced myself. Mike found me strange but we shook hands. Mike was holding a gay porn he brought with him. He put it on top of my VCR and suggested we sit. He had been looking me over the moment I opened the door. Mike was surprising good looking! He had a nice thick moustache, dark hair and brown eyes. We sat down and he immediately opened up my towel. My cock was so nervous it just laid there until he started playing with me.

We didn't say anything! I began to rub Mike's crotch area. His cock was easily aroused. Mike worked me up stiff. The rubbing went on for a while as I couldn't believe this was actually happening! I unzipped Mike and his long slender cock jumped out. Upon seeing his perfect cock, I felt inferior. I told him in a shaky voice how huge he looked compared to me. Mike smiled for the first time and he told me I was the hottest guy he had ever met. Then he started rubbing my chest and touching my abdomen. Mike told me I had the biggest chest and I had nice abs. We stood up. I played with Mike's torpedo and he grabbed my ass. I jumped into him as his pants fell down to his ankles our cock touched! Mike was two inches taller than me and it was the closest our lips ever got. Mike being in a relationship didn't kiss usually and I had no problem with that. Mike took off his clothes and walked into my bedroom with Mike following me naked. It was dark except for my curtains open letting the moonlight in. I moved up on the bed and Mike moved up between my legs. I handed him the bottle of lube. Mike casually lubed his fingers and drove them into my ass hard. I wasn't expecting how hard he drove two fingers into. I grunted hard trying to mask my fear. He kept stuffing them in over and over. I cringed as Mike said how tight I was. He chatted stating he liked breaking in tight asses. I had joked online my ass was tight but now...I was second guessing myself. Mike took his fingers out and rubbed lube on his cock. I began to rub mine. We had chatted and Mike wanted both of us to cum at the same time. He would pull out and cum on me and I would do the same. Mike pushed his tip against me and my ass tightened up. He pushed harder. His tip passed into me. I grunted and moaned in scared pain. I pushed him out again. Mike told me to relax but I was too nervous. Again I pushed him out making a strained noise as my ass fought to keep him out. Mike had me raise my legs up and he bore down into me. I thought I heart a pop sound when he broke me. My heart was racing and my head was spinning. I cried out in total shock when Mike entered me. He leaned into me from above. His cock felt huge! I gasped for air and began to masturbate fast with his cock in me. I jerked oft incredible fast and hard trying to counter the intense pain from in my ass. Mike pushed deeper and deeper. My breathing was quick and shallow. Mike worked himself in and out. I had never experienced such pain. My face cringed. Mike asked if I was ok. I was jerking off so hard and focused on wanting to cum. I nodded while grunting loudly I was ok. Mike's cock was stretching me and my moans were long and loud. My face said it all. Mike continued to work methodically. I moved much faster. I shot my load high up in the air in front of Mike. His eyes got big at how high shot. I kept jerking off faster as the cum landed on my body and face and bed sheets. When I emptied, my cock was still throbbing and bouncing against my lower abdomen as Mike kept fucking my ass. My eyes looked at Mike's hairy chest and his chiseled abs as he worked into a sweat in and out of me. I continued to groan and cringed in pain. I was now gripping the bed sheets hard. Mike looked at me for s few minutes then he asked if he should stop. I managed to ask if he was close and he shook his head. The look of terror on my face was enough and Mike being a nice guy pulled out. The fire in my ass continued to burn inside me. When he pulled out my cock jumped and I curled up into a ball. Mike stood up from the bed and he moved beside me jerking off. I reached over and helped. Minutes later Mike shot his load onto my face. The cum didn't erupt like mine, instead his just seeped out in three clumps. He tasted awful along with the smell of lube and my ass on him. I made a face as I wiped it off me.

It all ended as quickly as it started. I had hope Mike would stay and we could have another go at it but I saw the disappointment on Mike's face. He said he had to go. We took a brief shower together to clean up. I was washing his cock and almost started to suck him but I chickened out. We toweled and I watched Mike dress quickly as I stood there naked with a very sore ass. He left without saying much. I asked him to im me when he got home.

Mike chatted briefly with me. He was disappointed in me. He said I was very good looking and in better shape than most guys but the sex wasn't good for Mike. He had hoped that I would sucked him off after he pulled out of me or even in the shower. He was very blunt telling me I should of swallowed his cum instead of making a face of disgust and wiping it away. I felt like shit and rightfully so.