Just to carbon date the time a bit. I lived in a rundown apartment complex on the southeast side of town nicknamed ‘South Ghettos’ during my sophomore year in college. My internet was dial up America Online and I had a Gateway computer. I had a very small one bedroom apartment that I had planned to share with my girlfriend but things didn’t work out and so I was left to float the bill myself. Ok enough about the sad story, let’s move on…
I was 5’10”, 135lbs pale white, with shaggy blonde hair, blue eyes, 19 and always horny. I found myself masturbating daily to porn, while surfing personal ads and hanging out in various chat rooms. I had a job working at movie rental place, where I was promoted to assistant manager on account I showed up to work.
I was becoming more bicurious due to watching gay porn and being so turned on by it. My erections were harder and my ejaculations were so explosive. My seven inch extra thick cut cock with a nice mushroom shaped tip was throbbing in my right hand. I had been chatting with other gay men. I did role play, exchanged nude pictures, and did cam to cam mutual jerk off sessions. Most of the guys online at the time were much older but that didn’t bother me….I liked the attention!
One Tuesday night, I was in a local m4m chatroom when I started talking to this guy. His name was Mike. He was 37, bisexual and in an open long term relationship with his partner of four years. We exchanged pics and I was immediately impressed by Mike’s body and his long slender cock. Mike was hung! He was just over 8 inches and had this wonderfully mushroom shaped tip. He was taller than me about 6’1″, in good shape moderately hairy and he was a top. He lived just twenty minutes away from me.
We started talking and it turned very sexual quickly. I told him I was curious as a bottom and had been masturbating while using a dildo in my ass. Mike easily persuaded me into sharing graphic pictures of myself including a head shot. Mike was very interested in meeting me in person and he suggested a provocative idea to me. He listed off some desires he wanted me to do for him. I got very turned on by the ideas.
Mike and I agreed to meet at my apartment within just an hour and half of chatting online and a brief phone call verifying I was real. He gave me on hour to prep for him. On Mike’s advice, I rushed to the store and bought an enema, condoms, and lube. I came back to my apartment and jumped in the shower to shave my cock and balls. I was shaking nervously as I shaved. I got out and toweled off my newly shaved smooth body and laid on the floor of my bathroom and inserted the enema. The cool liquid filled my ass and I stayed on my side for as long as I could. The sensation of having to go came on so quickly that I barely made it to the toilet. My body pushed the contents out with such force it sounded like I was pissing out my ass. Even when there was nothing left in me I still wanted to push out. When the urge had stopped, I flushed myself one more time then prelubed my ass for Mike.
I had just minutes to spare and wrapped a small town around my 30 inch waist and waited nervously for Mike to show up. The anticipation was excruciating, I paced around my small apartment thinking. I had even contemplated backing out shutting off my lights and hiding in my bedroom. Then I heard a door slam shut and I peeked out and saw him. He stood by his car taking one last drag from his cigarette before flicking it away as he saw me peeking through the blinds. I knew then there was no turning back. I heard him walking up the stairs to my apartment. He knocked and I immediately opened the door.
Mike stood there. It was the first time I actually saw his face. He had a thick moustache and I stood there witty my cock fully erect under the tiny towel wrapped around my waist. He stepped in and locked the door behind him as I backed into my small living room. I was shaking so badly and my voice quivered as we spoke. Mike looked at me with his dark brown eyes and he suggested we sit down on my couch. He sat next to me and opened up my towel. He touched my chest and quickly ran his hand down to my cock and balls. I could help myself as I moaned softly from his touch. Instinctively, I rubbed his crotch. His cock began to grow under his pant leg. He let me unzip his pants and I was allowed to pull his massive cock out. It jumped out of his pants and I couldn’t take my eyes off his perfectly shaped cock.
I was in amazement and bewilderment and my body began to shake uncontrollably. I stood up naked in front of Mike. He also stood up and grabbed my firm little tight ass. He suggested we go into my bedroom. I nodded nervously and went before him. Mike undressed and followed me. I had a twin sized bed and Mike felt comfortable to lay down on the bed. I stood there admiring his muscled chest and abdomen with his cock hard. He motioned me to join him. I crept up on his legs touched his legs then his chest. Mike took both our cocks and held them together stroking us. His cock felt so warm against my smooth cock. He stopped and pulled my hips over his. I rubbed myself against Mike. I moved up and let his hard cock skim against my ass hole. I jumped and my cock bounced from just his tip touching me there. I began to sweat thinking about our earlier conversation about whether we use a condom or not. I wanted to to because I was scared. Mike preferred without but it was my call he said. His cock now was rubbing between my ass cheeks as he had his hands on my hips. I moved up and down backing my ass against his firm rod. I was nervous but also very aroused having never done anything like this before. I raised myself as Mike touched my firm chest and abs. I leaned over Mike and grabbed a condom. I opened it up and saw disappointment in his eyes. He did say a word, just gave me a look. I raised myself up onto my feet in a very low squat. Mike steadied me with his hands. I placed my one hand firmly upon his chest and with the other…..
I dropped the condom and took hold of his cock. I aligned it and lowered myself onto him. I remember how it felt as his tip passed into me. He felt huge, I felt atretched, I moaned and panicked almost falling over Mike. I groaned in both pleasure and pain as he passed into my ass. Mike told me to breathe as I winced in pain. I cried out terrified that his bare cock was in my ass. It was an incredible sensation to have his giant cock penetrate my ass. I lowered more then I had to stop from falling over I moved off of him. Mike didn’t seem upset and I moved to my knees and straddled him. I grabbed to lube and proceeded to squirt a generous amount down my backside crack and onto his cock. I worked his cock and Mike asked me to slow down. I tried but quickly attempted to insert him into me again. I raised myself on my knees and took his tip running it undue my balls and back and forth over my throbbing ass. I had to tilt to one side because his cock was so long and I lowered myself down. His tip slipped easier into me. It felt much smoother and with one breath. I lowered myself down onto him. I recall the sensation of wanting to throw up as his cock went deep into my ass. His cock stretched me in new ways. I groaned and winced as I tried to take as much as I could into my virgin ass. I looked at Mike, tears in my eyes and shaking still. He held me down on him and told me to relax.. He stated that it would be more pleasurable for me if I just let go of my nervousness. While nervous my ass was trying to push him out. Mike told me to masturbate and so I did. Then he began to play with my erect nipples. Mike told me how good my ass felt and that seemed to help. I began to move slowly up and down on him while jerking off for him.
We began to move in rythmn and my breathing became heavier. I was sweating alto as our bodies meshed. I moaned as he passes in and out of my ass. Mike suggested we change positions. He had afforded me being on top but preferred a more dominate position. I moved off of him and my ass let out juicy flatulence. Mike stood up and I moved onto my back and lifted my legs up. Mike moved into me and pressed his shoulders into the back of my legs and up into my ass. He used some lube and fingered my hole hard. I grunted from his fingers probing me. He guided his tip and pressed in. Again I tried to push him out but Mike was too powerful. I went deep and again I was touched deeper by him. I began to stroke myself harder as he continued to glide deeper into me. In a brief moment of humor, I asked Mike how deep he planned to go as I thought his cock would be coming up my throat. Mike laughed and in doing so I felt his cock jerk inside my ass. Sensing Mike relax too helped me. It still hurt like nothing I had ever experienced but I was also so turned on by what was happening. I let go of my inhibitions and my cock and began to enjoy touching Mike as he plowed into me harder. I told him how big he felt in my ass, I told him he was stretching me as he moved over me more forcing my legs over head. My cock now was touching my lips. Mike pushed down on me as he assisted me suck myself as he fucked my ass raw. I enjoyed seeing Mike enjoy the sight of me self sucking just my tip. I was so close and gargled to tell Mike. He was close too he said and wanted us to cum at the same time.
I tried to hold out but I couldn’t hold it back. My cock slipped out and surged seamen into my eyes, nose and mouth while covering my face. I gasped for air while swallowing as my whole body went into convulsions. Mike failed to pull out in time and also jerked hard three times injecting me with his fluids. My true fear had succumbed to Mike’s will. He had cum in my ass!!!
When he had finished he pulled out leaving an empty sensation in my ass. He opened my gape up and watched my ass involuntarily push his seeds out onto my bed sheets. When satisfied, Mike quickly got dressed and left me with weary dropping ass and cock wanting more,
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