How I Lost My Anal Virginity

This is a completely true story as to how I lost my anal virginity about a year ago. This is also my first time posting on here. Constructive criticism is more than welcomed. Hope you enjoy.

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I had previous success with posting to Craigslist. I had met a few times before, but it was just for some oral play. Ever since I was eighteen I wanted to be fucked. I decided I would post an ad stating I needed fucked. I said I was down to suck and play, but fucking my ass needed to happen as well. In my ad I explained I was an anal virgin. I had used toys to fuck myself, but I needed a real cock to satisfy my craving. I had multiple replies, but I was being picky. I settled on an older white gentleman who had a huge 9-inch cock. We arranged to meet at his work later that day after I got off work. I was happy I had shaved early that morning, so I was smooth all over.

I got off work and nervously drove over to where he worked. I followed his directions to go back to the building he told me in our emails. He told me to find the door with "314" on it. I parked and walked up the steps. I finally found the door on the third floor. I knocked and nervously waited for someone to answer. The door opened and a tall white male appeared behind the door. He had some scruff on his face from not shaving for a few days, but he smiled and welcomed me in. He wore jeans and a button down plaid shirt. He directed me into a room a few feet off to the side. I saw sitting on the window sill he had lube and condoms laid out ready and waiting

I shed my outer clothing quickly and got down to my boxers.

As he came in behind me he said, "I've needed this for a long time. I've got a big load built up."

Eager to get to it I dropped my boxers and kicked them to the side of the room. I dropped to my knees in front of him as he started to undo his belt. He unzipped his jeans and put his thumb in his briefs. He let them drop and I started to see his hung cock. As his pants dropped it felt like forever before I finally say the tip of his head. He was not kidding about his size. I started to have second thoughts about whether I should tackle such a large cock as my first time. I felt I was in too deep to back out now. So, I took my hand and took the base of his long circumcised cock in between my fingers. I lifted his heavy tool up so it pointed directed at my face. His balls hung down just as monstrous below his member.

I was in awe for a moment because he blew me out of the water size wise. I am maybe 6-inches on a good day, but my cock wasn't getting touched today, so it doesn't matter.

"You like what you see?" He asked.

"I love it. It looks so tasty," I replied.

With that I licked my lips and pushed his tip to them. I let my lips part just enough to hug his tip as I slid it in my wet eager mouth. It was bigger than any cock I had ever sucked. I knew there was no way I could deep throat this monster. I slowly started to stroke his cock's shaft while I sucked on his tip. I let my tongue explore his hole and wrap around the head of his big cock. I felt him start to grow and become more stiff. I lowered my head down to take more of his cock in. I swallowed as much as I could before I started to gag. I heard him start to moan, so I didn't want to stop. I started bobbing my head back and forth while letting my tongue run down his shaft each pass. He put his hands on my head and use them to increase my speed to his liking.

"Oh fuck yeah," he moaned.

After a few minutes his cock was slippery and dribbling with my spit as I swallowed most of his cock every time I went down. He pulled my head back and told me to get on my hands and knees. Without a second thought I spun around and bent over ready for what was to come next. I spread my knees and laid my head down on the floor so my ass was up in the air waiting for his huge rock hard cock.

"Do you want bareback or a condom?" He asked while he stroked his cock.

"Bareback," I replied. "I want to feel you cum in my ass."

"Oh I will fill your tight ass up."

He took the lube and put some on his fingers. He started to massage my hole to try and loosen me up before tackling his cock. He knew to take it slow and gentle at first since my ass was a virgin. He slipped one finger in first and slide it in and out a few times. I felt another finger enter my hole and he started to pull them apart stretching my entrance. He coaxed me and reassured me to relax. I just laid with my head on my hands on the floor. Another finger entered and he started to finger fuck my ass. I moaned quietly as I felt his fourth finger enter and stretch me a little bit more. Satisfied with his work he withdrew his hand and started to lube up his big cock. I looked back at him as his rubbed his member and I scooted back to him eagerly. He took his cock and pointed his head at my entrance. I felt the tip press against my hole. It started to feel uncomfortable as his tip broke my entrance. I felt it slip in and I let out a gasp. He paused a moment to let me relax again and then he pushed farther in. It burned at first. I thought I couldn't do it. He is too big for my first time. This was a mistake. Then he pushed again and another few inches slipped in. He grabbed my hips and started to slide his cock back out. I felt his tip get to my entrance before he slowly buried his cock back in my ass. I felt every inch until he was pressed against me. I felt his balls press against mine. It was still uncomfortable, but it didn't burn like at first. I just felt really full. He started to exit me again and I left out a soft moan.

His grip on my hips hardened and he pulled me back against his cock as he pushed himself forward. I realized it was starting to actually feel good now. It no longer hurt.

"Oh my god you are so tight," he breathed.

"Oh fuck my tight ass," I begged.

He increased his speed to where it was a steady pumping. His strides were so long. To pull his whole 9-inches out and slide them back down in me felt like each one took forever. I closed my eyes and buried my face in the carpet. My hands clawed at the carpet as he started to fuck me harder. He started moaning with each push. He repositioned himself so he was standing over me and plunging directly down into my ass. I felt his cock hammer down in my ass with force each time. I realized I was moaning each thrust. I didn't realize I was before. It was subconscious. My body telling me I was actually really enjoying being plowed by this monster. He went back to his original position behind me and started forcefully thrusting his cock in me. I started matching his thrusts so it would plunge down into me even harder. By this time I was moaning uncontrollably. I felt him grab my hips to the point it was starting to hurt. I could tell he was getting close. He cock felt like it was swelling up and he started to move to short rapid bursts. We moaned together while I pushed back against his cock so his balls slapped against mine each time he pushed in.

"Oh yeah, cum in me," I moaned.

A few rapid thrusts later he made one final hard thrust down into my ass before I felt a warm splash against my walls inside my ass. He pushed so hard against me I almost collapsed. With his full weight on me with his cock buried in my ass his cum kept exploding from his cock. I felt hot shot after shot fill deep within my ass. I moaned so loud I thought for sure someone would have heard us. After about seven or eight shots of his hot cum he started to pull his cock out. I laid there exhausted as he exited my ass.

"Oh my god I needed that," He gasped exhausted.

I got back up on my hands and knees and felt a dribble start to run down my balls. I knew what it was. And I was so happy I finally got what I was after.