First time bottom

My first time being fucked

I am a died in the wool TOP. I love sucking dick and even enjoy sucking my bottom while fucking him. I have bottomed three times. My first was with a Middle eastern sailor. He spoke no English and I spoke no Arabic.

I walked up to him in a gay club in San Francisco. He had been giving me the eye and I liked what I saw. He was about 20 with light skin and curly black hair. Very pretty in a handsome way. Manly yet quite a twink. He was about 5’5” and slim. I followed him into the back room of the club and he stopped and leaned against the wall with one foot up.

I looked at him and bent down to kiss him. He reacted oddly to the kiss and turned away resisting. I thought he was just playing so I increased my pressure against his mouth and probed him with my tongue. He reciprocated and started humming and panting while our tongues enjoyed each other’s mouths. He grabbed my dick sizing it up through my jeans. He pulled my dick out of my pants and started sucking it right in the back hall. He seemed to enjoy my uncut dick and was quite masterful with the foreskin.

Since we were dressed, I reached down and unzipped his pants. His dick was sweet. It was about 5 inches long and thinner than two fingers wide. I had never been penetrated successfully. Many have tried but those massive hoses would not fit into my virgin hole. His seemed right sized.

There was a chair at the end of the hall and I led him to it and sat him down. I slobbered on his small dick until it was slicked up and dropped my pants and sat down on his dick. I really didn’t know anything about prep for bottoming or anything about slow and steady or PAIN. I found out immediately.

Once I was impaled on his dick the pain hit me. It was like someone shoved a hot poker up my ass. Well, that was what happened. There was no pleasure and I just sat there trying to breath. He on the other hand had his dick in a hot tight place and he started to enjoy himself. I could feel his dick widen and stretch my pained hole even more. I didn’t know some guys have a hardon that grew wider after more attention. Mine goes from zero to hard in 3.2 seconds. I do grow a little more after attention but usually by fucking time it has had time to get to the max.

I started to pull off and that hurt even more. I had visions of us walking to a hospital attached like dogs, not a good thought. He pushed up and came in my ass. It wasn’t a two-pump chump but a one thrust gush. I could feel every pulse and knew what was going on but was not enjoying it even a little. Blessedly his dick started to subside and the cum acted as lubricant to help me get him out of me with little further pain. The head on his uncircumcised dick had a flare and it caught on my sphincter giving me a little more trouble, but I finally just pulled off like a band aid.

As I stood up, he looked at me with his dick covered in blood stained cum and particles of shit. What a mess. He just sat there like what had just happened. I headed to the bathroom and wiped my ass off. A lot of blood was coming out and I had to form a wad of toilet paper to plug my asshole. Then I pulled my pants up and started to walk out. My dick was limp from the time I sat down on. No pleasure from pain there.

Each step felt like my ass was being torn. As I walked out of the club there were a lot of guys snickering and looking at my hitched gate. As if they never walked funny after being fucked. I really felt like asking if there was a better way to walk while bleeding out of your bottom but didn’t.

I have bottomed two more times without the problems of my first time, but those stories are for another time. I always read and hear about how great bottoming is, and how you will get used to it. Let me hear your thoughts.