Straight Male / 49
Losing My Anal Virginity
When I was 18 I had to do two weeks in jail for a traffic violation and property damage. It was in a pretty shitty county in Ohio. Lucky me I guess.
Upon arriving to jail I was strip searched had to spread my cheeks and what not. Then I was issued their jail clothes. Just sweat pants a white shirt sweat shirt and some white briefs. They briefs were kinda worn out too.
Got placed in a cell with a guy in his late 40s I’d say. Comes bedtime this guy was in the cell in just his briefs. Pretty big bulge in them. Never once crossed my mind that sex happens in a county jail. No idea how long that guy was in for either.
Well the second night after the lights went out he jumped off the top bunk and pulled his dick out. He just told me to suck it. I thought he was joking but he said we can either start with sucking or I’ll just go straight to fucking.
So I was bent over my bunk. He took my underwear off and tossed them on my pillow. He spit on my hole twice and once on his dick. He began to push his dick in my butt. Hurt at first. It was uncomfortable the whole time. Luckily he got off fairly quick. He shot his load in my butt then he put his underwear back on and got back on the top bunk. I put my underwear back on and laid in bed with a sore asshole kinda in shock.
This went on for the whole two weeks. Definitely made me never get in trouble again.
Upon arriving to jail I was strip searched had to spread my cheeks and what not. Then I was issued their jail clothes. Just sweat pants a white shirt sweat shirt and some white briefs. They briefs were kinda worn out too.
Got placed in a cell with a guy in his late 40s I’d say. Comes bedtime this guy was in the cell in just his briefs. Pretty big bulge in them. Never once crossed my mind that sex happens in a county jail. No idea how long that guy was in for either.
Well the second night after the lights went out he jumped off the top bunk and pulled his dick out. He just told me to suck it. I thought he was joking but he said we can either start with sucking or I’ll just go straight to fucking.
So I was bent over my bunk. He took my underwear off and tossed them on my pillow. He spit on my hole twice and once on his dick. He began to push his dick in my butt. Hurt at first. It was uncomfortable the whole time. Luckily he got off fairly quick. He shot his load in my butt then he put his underwear back on and got back on the top bunk. I put my underwear back on and laid in bed with a sore asshole kinda in shock.
This went on for the whole two weeks. Definitely made me never get in trouble again.
- That's Juicy! 20
- Remove It! 2
