Do you remember the first guy that fucked you?

[AlB]

Julian DiLorca.  I was in my early 30s; a ten-year “convert” to getting off with men.  I was probably four years into fucking men but had never been fucked; sucked but my ass was off limits.  “Converted” meant starting to get off with men in the Army.  It was convenience and damn good way to get off with little hassle.  Anyway one particular really hot masculine bottom fuck-bud I had one day out of the blue started massaging my ass when we were giving me time to recharge after a fist fuck.  He’d always been complimentary of my hairy bubble butt but that night was different.  He had what I thought was a frighteningly huge dick (until I hooked-up withr my husband; then I knew what HUGE is!) and I had never even had a passing thought of getting fucked much less by him.  But we were blissed-out and out of the blue in his very deep voice he asked, “Are you ever going to let me stick anything other than my tongue in here?”  Call it the endorphin rush, something primal with his deep voice and oozing masculinity but I said, “Promise you’ll drive me to the ER and stay with me afterward?”  Two hours later I was begging him to fuck me a third time even though my hole felt like a dump truck had backed up in there and ripped me apart.  I was covered in my own cum and filled with his; what hadn’t run out of my stretched gaped hole.  Oddly I never saw him again and never talked to him again after the next day.  He had left on a business trip to Asia and was just poof gone after that.  I admit that as time passed I rationalized my decreasing interest in finding closure as my wrecked hole convincing me it was for the best.  But I’d like to know; ya know?

[PaganzofLA]

ACTUALLY NO, I'M A 57 YO VIRGIN LOOKING TO MAKE A MEMORY THIS AFTERNOON...HMU

[KindaBasic]

Yes. With the fondest of memories. 

[wh0rehole]

Literally the best fuck ever, and I'll never forget it.

The mailman hand delivered one of those racy pin-up type birthday cards with a male bodybuilder and had written his phone number in it the day before my 18th birthday. Being the polite young man I was, I called later that evening to thank him for remembering me, and the next thing I knew I was headed to his house the following afternoon. It was my exact 18th birthday, and 2 weeks before I left for college.

He lived in a community where you had to be at least 55 to live there. This stud was a MINIMUM 37 years older than me, and he plowed me raw in every position I had seen in porn, plus a few I hadn't yet seen.

He bred me 3 times and throughout the afternoon taught me how to service an older man.

I'm convinced this is why I'm so fond of older men. No fuck has ever compared to this one since.

[TomOnHisKnees]

My best friend after we double dated.

His girlfriend wouldn't put out so I offered and he accepted.

[Nikba]

7 hours ago, wh0rehole said:

Literally the best fuck ever, and I'll never forget it.

The mailman hand delivered one of those racy pin-up type birthday cards with a male bodybuilder and had written his phone number in it the day before my 18th birthday. Being the polite young man I was, I called later that evening to thank him for remembering me, and the next thing I knew I was headed to his house the following afternoon. It was my exact 18th birthday, and 2 weeks before I left for college.

He lived in a community where you had to be at least 55 to live there. This stud was a MINIMUM 37 years older than me, and he plowed me raw in every position I had seen in porn, plus a few I hadn't yet seen.

He bred me 3 times and throughout the afternoon taught me how to service an older man.

I'm convinced this is why I'm so fond of older men. No fuck has ever compared to this one since.

I had the same experience at the west side. The guy took his time to explore every inches of me and made sure I received every imaginable pleasure. A very experienced person with technique and passion. He later introduced me to his friends. 

[Guest]

Absolutely. I remember I was like 25 and this 40+ dude invited me over to his place. First time I ever did that with a guy (usually a little worried about meeting strangers). Anyway I digress… turns out he had a private sauna and an area he called his own playroom. 
 

He knew I wasn’t experienced so he took a lead of the situation, told me to get naked and did so himself. While I was undressing he groped me all over and we started kissing. This made me rock hard. It was then he reminded me I was „there to get fucked“, so I better get to work on his cock. I got on my knees and started playing and licking it. This progressed into me giving him oral which in turn got him rock hard. He wasn’t that huge, but he sure was girthy.

Soon enough he told me „it’s now time for you to get fucked“ so I was told to lie down on the mattress on the floor and spread my legs. He said since I got him nice and wet this would probably be good lube if we do it bare, but he didn’t want to pressure me. He told me he is going to cum in one of my holes whatever my choice.

I was a coward back then so I regret to say I asked for a condom. He put it on, rubbed some coconut oil on and inside my hole, then lined his cock up and gave a long and hard push. He wasn’t pulling out until it was all the way inside. My hole took him way better than I thought it would. After a few moments to adjust he started fucking me harder and harder. 

This fucking went on for what felt like hours. When he wanted to change to doggy, he pulled out and told me to get up on me knees. It was then we realised the condom had broken. „I’m not wasting another condom tonight, they’re too expensive“ he laughed, and started putting it inside me again. This felt a lot better for the both of us and he proceeded to fuck me nice and hard. At some point, I knew he was getting closer to completion.

I was so scared of him cumming inside, I pleaded with him to please pull out before he cums, a request he could have easily ignored. „I am going to cum soon, if you don’t want it in your ass you will have to take it in your mouth“. I had never done ass to mouth, so the idea was a little off putting at first. But I guess it was safer than a huge load of cum inside my ass, so I agreed. 

„You better turn around quick once I pull out“ he said. He gave me a few more strokes. He could have easily ignored my wish to pull out, but being the gentlemen he was, he did actually pull out - and started cumming before he even reached my mouth. While sucking him and swallowing the remaining cum he said „it was almost too late“, and that he seems to have managed to cum in both my holes.

I was a little shocked at that statement and when I felt my hole and felt the sticky liquid on it it was confirmed. He saw my worried look and said not to worry and began to finger me, forcing the liquid back my hole. His fingering got faster and this made me hard. He grabbed a hand and started stroking my cock. This was too much to handle and I came all over the mattress.

He asked me if I’d be back again. I came back often. 

[wh0rehole]

6 hours ago, Nikba said:

I had the same experience at the west side. The guy took his time to explore every inches of me and made sure I received every imaginable pleasure. A very experienced person with technique and passion. He later introduced me to his friends. 

I feel like we are so very lucky to have experienced this. So gentle and affirming to my young gay self that I was OK. That getting fucked up the ass by a man could feel so good and didn't have to be shameful.

I went to college on the other side of the country, mostly to get away from my shit family. I wish I had kept in touch and seen him again on breaks, or that he could introduce me to his friends. But I was especially terrified because it was the early 90s and he went in raw and BRED. He didn't even ask, he just did it, and I had a lot of feelings about why it felt so normal and good. The only porn available showed condoms, and going bareback wasn't really a "movement" per se like it is today. It was a real mindfuck at the time (I know he didn't do that on purpose, he just did what a man his age would do), but I'm grateful for it.

[Jeanscumpig]

Oh yeah, yes he was awesome, unfortunately he passed away but I will never forget him

[nettlekiss]

Yes, I do. He was in his 40s and muscular. I was 19 and had only had a finger or two in me. Watching too much gay porn that day I guess 🤷 lol..  got to the point where I just had to feel a real cock in me.. ..and his cock.....omg, hurt so good.

[Markcumdumpguy]

Not first cock, but do remember first bareback fuck, started prep and hooked up with a young fit dancer. His cock was massive and only just take it and even better I got his cum raw. So prob best experience for first bb. 

[KindaBasic]

I still jerk off to the memory of it. 
 

[Luxbrit]

Yes I do because it was awful and the guy was rubbish but hey at least I can say I lost my virginity on a water bed 🤣🤣

[Willing]

Never been fucked by a guy, but I remember being fed by my 13 year old friend when I was 8 after church on Sundays 

[Searchingforit]

I remember it weĺl. Trouble is it was all over very quickly and not satisfying at all