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Bi-Sexual Male / 30

Lost My Virginity

I’m a pretty shy guy when it comes to sex so the thought of losing my virginity just made me nervous and embarrassed

Last week I had to go out of town for a doctors appointment. Afterwards I was out shopping for some stuff and also looking on a hook up app. I ended up chatting with a 63 year old.

Chatting along he asked what I was into and I just mentioned I’m new to this. He figured out really quick that i was a virgin. After convincing me to go to his place I nervously agreed. But I told him I’m very nervous and he said that’s understandable

To say I was very horny is an understatement. I was extremely horny and my hard dick was ready to rip out of my briefs.

He had me suck him at first which was amazing to say the least. Nice dick he had. Then he sucked me for a minute before telling me to flip over. He ate my butt. I had no idea that would feel so good

But then came the anal sex. It hurt as he penetrated me and once he penetrated me it felt like my butthole was gonna tear. I was moaning and breathing heavily as he told me to relax and let my hole relax. He told me the first time always hurts

But as I worked on relaxing he started to fuck me. It started feeling better and eventually just felt like I had to poop honestly. But my dick was rock hard

As he’s behind me holding my butt as he fucks me he starts to moan and says you got a tight butt. Then he lets out louder moans as I feel his dick pulsate. I could tell he was cumming in my butt.

As he finished cumming he tells me I have a really tight butt and he couldn’t last any longer. He pulls out and says virgin butts are always so nice to fuck

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# 77792 - by Tony / March 25, 2025
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Comments

Anonymous

by Anonymous on Mar 25, 2025 at 2:49 PM

First timers are the best. So unsure, nervous, scared and cute.

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Anonymous

by Anonymous on Mar 26, 2025 at 6:13 AM

Similar to you. I am a shy guy in his early 20's. Was seduced by an older trucker last year after he checked in to the motel where I worked as a desk clerk. He asked me to his room and after I got there made advances on me.He is a burly strong guy and ended up quickly lubing my tight little ass and pounding me hard until he came in me. It hurt like hell that first time but he has had me at my place many times since and slides that big cock in me with no pain at all. I love it now.

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Anonymous

by Anonymous on Mar 26, 2025 at 6:24 AM

I lost my anal virginity when I was 12 to my best friend in the woods. His dick was big and we were just horny young boys needing to get off.
He asked me several times over a couple of weeks and even pulled his dick out and let me see it and watch him stroke it and I watched him cum and it was a lot more than I came. He got me to jack off with him then jack him off. By then I was very curious and decided to let him try to fuck me.
We agreed that the only place we could do this was in one of the spots we knew that was very secluded down by the creek in some very thick brush. He brought some Vaseline and we were both excited about giving this a try.
Once we got to the spot we started to undress and once we were both naked our cocks were rock hard. He began to tell me how his cousin let him fuck him a couple of times and how to use the Vaseline to make it easier to stick his cock in me.
I will never forget laying face down on our clothes in the cool grass in the shade as he spread my legs then used his hands to spread my ass cheeks apart. I felt his rub the Vaseline on my asshole then put his finger inside me. That really felt good but what happened next was very painful. I felt him hold the big head of his dick to my asdhole then start to push. I felt my hole begging to open up and it felt good until it opened up enough to let the head of his dick go in my ass. I remember pulling at the grass and biting on my bottom lip as it felt like my asshole was on fire. I asked him to go slower and he pushed even more telling me it felt to good to stop.
It felt like a baseball bat was being shoved up my ass and for the next few minutes I had tears in my eyes as his big dick went deeper and deeper until I felt his big nuts on mine. I asked him to stop for a minute and he did but he kept pushing his cock up inside of me.
He said it felt so good that he was about to cum so he just laid on top of me awhile as his big cock pulsed deep in my ass. I had pre cum dripping out of my cock so I knew his pre cum was going up my ass.
Laying there naked with him naked on top of me with his cock way up inside of me made me start to feel like I belonged there and I wanted him to fuck me. I told him I was ready so he started out with short slow strokes as I bit my bottom lip still pulling at the grass waiting for it to start feeling better. It stung like hell but I wanted it and in a little while her was going slow but using the whole length of his long fat cock pulling out leaving only the head inside of me and it was pulling my asshole inside out.
He started doing it harder and faster and I could feel his nuts hitting mine and I started to cum all over myself and laid there in my cum as he fucked my asshole until I felt his cock grow even bigger inside of me then he started telling me he was going to cum. He got very excited and told me again he was going to cum. It felt too good to stop and I thought he would pull out to cum but I was wrong. He really fucked me hard a few times and I was making a lot of noise as I felt his cock explode deep in my asshole. He held on to me really tight as he shook all over and moaned out really loud as his cum filled me up.
To this day I still remember how exciting it was to think that my best friend had just came up my ass and how good it felt and I knew I would want it to happen again. He laid on top of me with his dick up my ass and we started to talk as he slowly pushed his cock up my ass and we shared our thoughts on what had just happened.
I made sure he knew I liked it and told him I would do it again if he wanted to. He told me he would always want to do it if I did. As he worked his dick back and forth in my asshole I began to feel his cum leak out of me and before long he was starting to fuck me again. The more he fucked me the more cum he pulled out if me and I had a lot of cum in the crack of my ass on my nuts and by the time he finished fucking me the second time we both had a lot of cum on
He fucked me for the longest time the second time and I caught myself asking him to do it harder. I came really hard the second time and I had my cum all over my stomach as he fucked me and fucked me then I started asking him to cum in my ass again. I guess that excited him because he started to pound my asshole and hold onto me really tight then he pushed his cock up my ass really hard and started to grunt and moan as his cum filled my insides again.
He left his cock in me until it got soft and started to slip out of me. As soon as his cock came out of me his cum ran out of me like a river. He got to his knees and pushed my ass cheeks apart and told me he liked watching the cum run out of my ass and I could tell my asshole was opened up like never before.
We jumped in the creek to wash off then back up in the brush to drip dry. We sat there naked talking about everything and we both got hard again after a good hour of nothing but talking about fucking. I still had cum leaking out of me and I asked him if he wanted to do it again. He said “sure if you want to”. I told him I really wanted it again so I turned face down spread my legs as he got between my legs leaning out over the top of me holding himself up with one arm as he held his dick to my cum dripping hole and lowered himself down on top of me as his cock went all the way up my ass then he fucked me for the longest time before he pumped my ass full of cum again.
We were there about 3 hours he fucked me three times and came in my ass three times and he made me cum four times. We swam and washed off in the creek once we were dry we got dressed and headed back to my house.
A few days later after he had fucked me several more times I asked him to fuck me again down by the creek and he said he would but he wanted to suck my cock and he wanted me to try sucking his too.
Once my cock was in his mouth I wanted his cock in my mouth and we ended up on our sides sucking on each other at the same time and when I came he never stopped sucking and had my cum in his mouth and that made him cum and now I had a mouth full of cum too and we both swallowed it and it wasn’t bad at all. He fucked me right after that and all the way thru the rest of our school days together he and I sucked each other off almost every day and he fucked me all the time.
Even after we got steady girlfriends he and I would sneak around and have sex with each other.
Once we got old enough to drive we both had a pick up truck and an hour for lunch so we had a couple of places we could drive to right quick and I remember both of us having our jeans down around our knees as he fucked me face down on the seat of the truck then we would hurry back to school with a bunch of napkins in the crack of my ass so his cum wouldn’t make a wet spot on my jeans.
Those were the good old days. Two best friends sucking each other off and his big cock fucking my ass and me taking his cum up my ass many times. I liked getting fucked so much many times I told him I wish we had a few more guys to join us because I wouldn’t mind having more cocks to fuck me and that always got him excited and he told me he would sure like to watch me get fucked by several guys. He and I drifted apart after high school and last had sex when he and I were 21 years old I wish we still
Lived close to each other because I would sure like for him to fuck me again just to feel that big cock up inside of me and have his cum in mecagain.

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