My first anal

I was a sophomore in college when I met Mike. We met through a Yahoo chat room titled M4M. It was a local chat room where guys would sometimes cam to cam, talk about sex, and possibly hook up. This was back in the early 1990's, so the internet was just catching on. Most porn videos were only 5 seconds long because of the size of the files compared to most computer processing speeds.

I was living off campus in a very small one bedroom apartment. I had just been dumped by my girlfriend and was very horny. I discovered gay porn and was fascinated by having a cock in my ass. I wondered how it would feel. I had fingered my ass before, used a plunger handle, even used a squirt gun and shot warm water into me. It made my masturbating more exciting. I scraped together a little money and bought my first twelve inch double dong dildo, a small set of anal beads, and some strawberry lube. Most of my time in my apartment I was nude jerking off to porn and chatting witn older guys. One night around 11pm, I started chatting with Mike. He was 34 and had an open relationship with his partner. He told me he was a top, preferred bareback, and liked to fuck college aged boys. I was a perfect match!!

We swapped pictures. I shared a full frontal and back picture of myself fully erect. He sent me a picture of him from the neck down showcasing his wonderful long slender mushroom tipped cock. He was very well endowed at eight inches!! My cock was only 6.5 inches and extra thick. Mike and I chatted and he had me cumming hard into my T-shirt just by how he wanted to fuck me when we met. It sounded perfect. He would come to my apartment and I would only be wearing a towel. But first I had to prep for him. He asked me to shave my pubic hair, give myself an enema, and lube my ass. Mike had me begging for him to come over. I gave him my address. Mike agreed to meet me at 2am. It was just after midnight.

Mike had to drive about 25 miles and I had to run to the store for supplies. I drove quickly and bought an enema and condoms. I was scared about being barebacked by someone i hardly knew and Mike agreed to wearing a condom if I bought them. I got a funny look from the check out girl as I paid and I blushed. I went home and laid on my side inserting the cool enema liquid into my ass. I stayed there until the urge over powered me and jumped onto the toilet to expelled the contents. It sounded like I was taking a pissed from my ass!! I felt relieved and weak. I stepped into the shower and began shaving myself. I liked how my bare cock looked. I then dried off and admired myself naked in the mirror. I had a nice lean athletic build from working out and running, I had light blond hair which was shoulder length with blue eyes, I considered myself average looking at best. I was 5'10" tall with a slender waist and a nice tight pale bubble ass. Mike was 6'1" in good shape, tan, a sexy dark moustache, dark hair and piercing brown eyes.

I stood shaking uncontrollably as i paced back and forth waiting for Mike. I began to wonder if he would even show up because everyone else before never did. I saw Mike's car pull up. He stepped out and finished cigarette. He flicked it out just before coming up the stairs. He knocked softly on my door. My hands were shaky as I unlocked and opened the door.

I opened it and let Mike step in. He scoped my tiny apartment without saying a word. I stood there in a towel. Mike pushed the door close behind him. I quivered introducing myself. Mike and I shook hands. We stood there awkwardly for a few seconds then he suggested we sit on my small couch. He sat next to me and unwrapped my towel. He began to touch me. My cock bounced witn delight. I began rubbing his pant leg. He cock throbbed and grew. Mike easily had me hard as he touched my chest and abdomen. I undid his buckle and unzipped his pants. I fumbled to pull out his long slender snake which was still growing. We stood up and we kissed. His moustache tickled me and the heavy smell of his cigarette filled my mouth.We went to my bed. I laid on the edge of the bed and was instructed to pull my legs up. Mike took his cock and mine and began rubbing them together in his hand gently. I reached for a condom off my nightstand. My hands were shaking so bad as I tried to open it. Mike said we didn't need it and I felt compelled to let the condom drop to the floor. Mike began to finger me. It was exhilarating and excruciating. He was rough especially when he bore two fingers into my ass. I cried out in pain. Mike smiled and said i was really tight. Somehow I took it as a compliment and gave a smile back with a shaky laugh. Mike moved over me and asked me to open myself up. He guided his perfect mushroom shaped tip into me as I painfully open my ass up with two fingers on each side. Mike felt much bigger than my dildo or anything else I had ever put into me. I grunted and moaned as he entered. I grabbed my cock and began to masturbate hoping that would mask my pain. My ass tightened and somehow I pushed Mike out. He seemed amused. Mike told me it would be better if I relaxed. I wanted to but the excitement of this older man I hardly knew was about to bareback me was much more intense. Mike forced himself in. It felt like I was about to throw up as I groaned loudly when he stuffed himself all the way in. My legs were shaking as thug were up in the air. Mike leaned over me very satisfied. He asked me how I was doing but knew by my expression on my face. My breathing was erratic my heart was racing. I squeezed the bed sheets firmly as my body broke into a feverish sweat. Mike took long deep plunges into my ass. I tried to not squeal. He felt so massive, my ass was expanding and it was killing me. The pain was much more than I had anticipated. Tears streamed down my face as I cringed everytime he plowed into me. Mike pushed my legs down over my head as he kept pumping. I involuntary pleaded with him to stop but Mike just kept going. He stared at me and I could tell he enjoyed my pain. He reminded me to jerk off. I did at a feverish pace. The faster i went the faster Mike pounded my ass in submissiveness. I was close to climax and Mike said he was too. The plan was for both of us to cum at the same time. Unfortunately, I erupted first. I had never shot my cum so hard. It rocketed up over my head and hitting the wall behind my headboard. One, then two, then three massive loads shot over and on me. Mike was astounded as my trajectory and the amount of cum that came out of me. I moaned and grunted savagely with every burst. Mike in his excitement unloaded in my ass!!! I could tell how his body jerked violently and his more modest grunting. He is injected me with his seeds. My eyes got huge as I tried to push him away instinctively. Mike swatted my feeble attempt easily away as he bore down deep in my ass. Now Mike had said before he was clean but could I trust him was going through my mind. Mike collapsed on me forcing me to exhale as his massive cock throbbed in me. When he did slowly pull out. I let out this hoarse cry. I sense of emptiness consumed me by his flesh no longer being inside me body. He stood up as I curled up on my side into a ball. My whole body ached and yet a warm sensation of enlightenment came over me like a warm blanket. Mike moved over to the side of the bed i was facing.

He informed me it wasn't over yet. He held his long slender cock in my face and gently rubbed his tip on my mouth. I looked up at him in bewilderment as I knew what he was expecting. Without a word, I opened my mouth and tasted his cum and my ass in my mouth. He slowly worked in and out past my lips. I suckled on it gagging hard on the salty stench. Then I gulped it down. Gagging hard. It made me sick to my stomach. Tears started to flow again as Mike touched my sweaty blond hair. "I think I found my new boy toy." He said with a smile.