Do you remember the first guy that fucked you?

[Gayasian]

Yes, my uncle and I was young.

[daemien]

I was 15, he was 21. We knew each other through a theater group. We had messed around naked a few times before, but the night he fucked me we had gone out to a movie. He was living with his parents, so he knew that we couldn't go into his house after. Instead, he had set up a cot in their garage. 

It didn't take much convincing to get me out of my clothes. I kind of enjoyed the danger. It had become a regular part of my sexual life, no matter whom I was having sex with. Since the age of ten I had been sneaking around with an older cousin sucking his cock in any space we could find whenever our families got together. 

Once we were both naked on the cod he very sweetly asked if he could fuck me. I responded with only one word, please.  He placed my legs on his shoulders and with only spit for lube he entered me. He had a modest five inch cock with a pointed head that flared and the shaft turned upward toward his belly in a gentle curve. 

He didn't hurt me. It felt amazing. I had been wanting it for some time and I had such a crush on him that I was so glad to to give my virginity to him. 

I went to sleep in my own bed that night with his load inside me. 

[InTown]

I had experimented in high school and early college with sticking the head in my ass but not much more.  I tried to do a little more bit it hurt too much.  In hindsight, it was really because I was too up tight.

Thus happened around 1990. I went to college in Cleveland and one night I met this guy out at the bar one night.  I believe it was Keys but it could have been Numbers.. His name was Tom and he worked at Eddie Bauer.  He was only slightly older than me.  

He asked me to come home with him so I did.  He had a couple staying with him from out of town.   They had the bed so we had the couch.  He sucked me off but I don't remember where I came.  He had not cum.  I was so exhausted at this point that I told him that I would make it up to him in the AM.  I had decided that it was only fair to let him fuck me for giving him blue balls but did not tell him choosing instead to surprise him.  That is exactly what happened he fucked me into spoon position.  We used hair gel for lube. I made him pull out before coming.  I was so proud of myself an I remember telling him that it was worth his wait from the night before. Ha. I was a little full of myself.

I was hooked.

We fooled around a couple of times after that and I was really falling for him.  We flipped fucked a couple if times always pulling out but I each time i did let the first shot go in him before pulling oit.   He became a jerk and essentially ghosted me or at least he tried to since we would see each other out at the club.

Armed with my new found bottoming skills, I decided that I would let my boyfriend back home fuck me.  This is  the boyfriend who I was cheating on with Tom.   My boyfriend was always the bottom in the relationship and always took it raw from me.

That is exactly what happened. Me and the bf were parked in a parking lot at a playground late at night after clubbing He fucked my bare and missionary in the passenger seat of my Honda Accord with his thick 8 inches.   We used suntan oil for lube. I knew that since I had shot my load in him countless times that I could not ask him to pull out so I did not and took my first load.   In hindsight, I should not have trusted him but I ended up being fine.  We broke up soon after and I never got his cock in my ass again.

 

[TightBott7]

Mine happened at 24. I had previously sucked off my best friend and swallowed his cum, but he never fucked me even though I had been fantasizing about getting fucked since I was like 9.

At 24, I went out to a Gay bar in a Chicago suburb with two friends. Then a guy about my age approached me and went right to the point: he wanted to fuck and get sucked. He was not particularly good looking, kind of thin and nerdy but it was his dom attitude that seduced me. I said yes and went to his place. The actual fucking was not very pleasant. Even though he had a small to average size dick, it hurt like hell. He took my ass raw and then he just sent me on my way. I could not have been in his apartment more than 30 minutes. A few days later on a Saturday, he called me and asked to come over to get fucked again and to buy some lube. I went as asked. The second time he fucked me I withstood the pain better but again he sent me home right after he shot his load in my ass. In all this I realized that at that point in my life I wanted a BF not a fuck buddy. When he called me again, I declined and he got pissed off. Never heard from him again. All in all, this experience reinforced my notion that I was a total bottom. To this day, I wondered how this guy knew I was a total bottom before he approached me even though I look very masculine.

[DaddyZboy]

Will you guys post more videos ?

[Guest]

I cannot ever forget my first fuck,he was my best friend, he fucked me for three years daily, he made me what I am today, a faggot whore, i was his bitch, to him i was nothing more then his bitch but to me he was my lover, i did everything he wanted, i was his release, his breeding hole basically i was his whore and pleasured him when ever he wanted, needed and met his erotic needs and pleasures.

[408curious]

Yes.

Although,  when I first thought id my answer I was wrong. 

... but yes.

[Faggotuser]

First ass I fucked was some faggot in my class in grade 7. Ifucked him and used his mouth for several years on the regular. Go ahead and tell them who it was @LittleCumSewer then tell them who the first stranger was.

[astrongoralfixatio]

I definitely lost my anal virginity to a craigslist hookup in a college bathroom. Just planned on blowing him and then in the heat of the moment asked him to fuck me. 

[LittleCumSewer]

22 minutes ago, Faggotuser said:

First ass I fucked was some faggot in my class in grade 7. Ifucked him and used his mouth for several years on the regular. Go ahead and tell them who it was @LittleCumSewer then tell them who the first stranger was.

the first guy that fucked me was my older brother. him and his buddy had been using my mouth for a couple years already. the first stranger was a guy who picked me up off the street dressed like a tiny gay slut at night. he parked somewhere quiet and fucked me in his car and busted his nuts in me. he also took my email address cause he knew his buddies would wanna fuck me too.

Edited March 18, 2021 by LittleCumSewer

[Puppyhole]

My first guy was my uncle while spending a summer week at his place.

[Guest faggotbitchboi]

The first guy who fucked me was a cabin steward on a cruise ship, I was 14.  Each morning provided all the cabins he looked after with a cup of tea (if they asked for one)...after the first time he fucked me in his galley (the day my parents, sister and I boarded the ship) I got a cup of tea each morning and more 😀

[bocini]

Best friend 15. Turned into a relationship that lasted too I was 20 yrs old. We had a lot of fun exploring the gay world together. Also made school interesting.  

[OhNoDontPozMe]

Topped first for a couple years before I ever bottomed. First one I fucked a guy was in a booth at an ABS. Raw of course. Felt so good. Like velvet. Loaded him up.

First time I bottomed, had met some guy in AOL. I was 23, he was perhaps 40’s. I went over to his house. He had a dog that barked a lot. He answered the door in an open robe. He was nude. I was super nervous. Immediately went to his bed. Not much foreplay at all. I don’t remember if I asked him to, or he did it on his own, but he put on a condom. 
I was straddling him. I’m 6’5”, and he was much shorter. Great big cock though, probably 9 or 10 inches. No kidding. So I’m sitting on him, his cock hard and pressing against my hole. In one motion, he pulls me down on his cock and he slides right inside me. No pain. He bottomed out inside me, and then began to fuck me. It may have been my first time but I quickly got into rhythm. I began riding his cock, matching his thrusts. 
I was really enjoying this. I remember being dialed into the moment and sensation, and loving it. A craving took over. I wanted him inside me bareback. 
I reached back, took his cock out of me. Took the condom off, and slid him right back inside me. He began fucking me without pause, so I think he preferred it raw too. 
So I’m riding him, really enjoying everything. All of the sudden, my ass felt really wet. I didn’t think he came that fast, but you never know. I reached down, to feel the wetness, that was now running down the inside of my thighs. It wasn’t cum.

I don’t know if it was the excitement, or being nervous, but I had shit while he was fucking me. He noticed pretty quick after that. Both of us were not pleased with the situation. He jumped up and ran to the shower. I ran to the toilet. I remember apologizing over and over.

He finished in the shower, then I took one. When I got out, he was dressed, and I didn’t need an invitation to leave. 
That was that. My cherry was gone, in the most embarrassing way. 
Needless to say, we didn’t communicate again. 

[BlackDude]

I’ve never bottomed.

But first guy I topped was a week before my birthday in my late 20s. I was lying to myself saying as long as I didn’t fuck guys, I’m still “experimenting.” He was Latino and invited me over for head with his BF, and I said fuck it, I’m gay. His ads looked so good and he was so cute. I finally owned it, and fucked him.

Invited me back a week later, without his BF knowing. He came home while we were fucking and it got awkward. I always regretted I waited so long and wasted so much time, but things happen for a reason.