My First Anal Experience

I was 20 and in college. I’ve always been in great shape because I ran track and was a runner in my free time. So I guess my skinny fit body with a nice bubble butt and perky breasts caught the eye of an older guy.

The guy who took my anal virginity was a teacher. He was in his mid 50s. Also a runner so he had a nice fit hairy body. At first I figured I’d just be giving him a bj. Being 20 at the time I loved giving bjs.

I’m on my knees in front of this guy. He asks me to remove my pants so he can see my thong. I’m holding his tighty whities under his balls as I suck on him

He had the perfect dick to me. 6 inches long I’d say. Cut. Decent girth and trimmed pubes. And nice balls.

As I sucked him we fully undressed. I got on top and rode him some. But he got in his desk drawer and grabbed lube. He started to finger my butthole.

Eventually he asked if I’ve taken it in the butt. I told him no.

He lubes up his dick and puts more lube on my hole. I sit on his dick. The initial stretch hurt but he talked me through it. Finally he was balls deep in my butt

I let this guy bend me over and fuck my ass. It felt so weird but felt so good.

As he was moaning and cumming in my butt I was rubbing my clit. I had the more intense orgasm ever. It surprised me.

As he pulled out of my butt he grabbed a few tissues to wipe me off. When I turned around I saw his wet hard dick. I couldn’t believe that fit in my butt.

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# 70582 - by Sarah / March 16, 2024

by Anonymous on Mar 17, 2024 at 7:20 AM

My first anal experience was when I was 13 and my grandma tickled my asshole while rubbing cream between my legs after I got into Poison Ivy. I was embarrassed when I couldn't hide my big boner, but it was a cool experience.

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by Anonymous on Mar 18, 2024 at 8:46 AM

My first anal sex was with my best friend when we were both 13. We had been sucking each others dicks for a couple of weeks and had gotten used to swallowing each others cum
We were at my house one day after school and no one else was home. We were in my bathroom naked jacking off together just about to suck each other off when he asked if he could fuck me.
I wasn’t sure about that but after we talked about it and I bent over and let him rub his dick on my ass I agreed to try it. I bent over with my elbows on the countertop and he got behind me. I was watching his face in the mirror as he tried to stick his dick in my ass. He started to spit in the crack of my ass and before long I felt the head of his dick go in my tight young asshole.
Both of us let out a moan and I felt a little bit of a sting as he pushed the rest of his dick up my ass. He grabbed my hips and started to fuck me and right away I began to like it and told him it felt good. I told him a few times to do it harder and I watched his face in the mirror as he was fucking me and I knew he was about to cum. I figured he would pull his dick out and cum on my ass but he didn’t. Instead he shoved his dick up my ass really hard and pulled on my hips. His head went back and his eyes were closed and his cum was shooting up my ass.
I just barely touched my dick and shot my cum all over the front of the cabinet I was bent over.
I started to move my add and shove it back towards him and squeezing his dick with my asshole. He started fucking my ass again but this time it felt so much better because his cum in my ass made my asshole very slick and his dick felt so much better fucking my hole.
We did it for a long time and he stopped a couple of times so he wouldn’t cum so fast. I was jacking myself off while he was fucking me and a couple of times I reached back and spread my ass cheeks apart so he could get as far up my ass as possible. It felt great and both of us were working to try and make it feel the best.
I asked him if he was going to cum in my ass again and he just nodded his head yes. I couldn’t wait and kept telling him to fuck me ! Fuck me faster! Don’t harder! Then once I started telling him to cum in me he got excited and shot his warm load deep in my ass. He kept his dick in my asshole until it got soft and began to slip out of me.
After it came out I felt his cum on my nuts and we just stood there quietly looking at each other. He asked me how I liked it and I told him I liked it a lot. He said he wanted to fuck me again real soon.
From that day on just about every day he fucked me and came in my ass for several years. Even after high school we would get together so he could fuck me. It was very casual between us and all one of us had to do was ask the other and we would go somewhere and he would fuck me and cum in my ass.
We are both married with children and grandchildren but about twice a year he and I go hunting and fishing together and all we do is suck each other off and he fucks the hell out of me with his long fat uncut dick.
If we drink too much it can get kinky he likes to tie me up and r**e my ass and fuck me with other things like beer bottles cucumbers and he had ever used a long thick flashlight up my ass.
A few months ago on our fishing trip I brought a bag full of sex toys for him to use on me. He spent hours sticking them up my ass and once he fucked me with the biggest one he tried to get his hand up my ass. It wouldn’t fit but just the feeling of trying to take such a large object up my ass with my dick in his throat made me cum like never before. He really got off watching me walk around the cabin naked with the big ten butt plug ip my ass.
That weekend was pretty wild and I almost took his hand up my ass. We are going to work on that until he gets his hand up my ass. We both want to do it and I like it when he played with my asshole
I wish we got together more often because I love ass play and he loves giving it to me. I bought a big long very thick 13” rubber cock for him to use on me next time and I will have a few other things in my bag by that time.

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My First Anal Experience

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by Anonymous on Mar 17, 2024 at 7:20 AM

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