Losing virginity to much older man, what was it like?

[Guest dtlbreeder]

For those of you lucky enough to have lost your v-card to an older guy when you were younger, what was it like?

[Leo177]

Pretty nice tbh (16/33)

We met on grindr, he drove me to his home, was really chill all the time, didn't rush me, used a ton of lube

Him being so nice was probably the reason i never cared about condoms

[Bokkierob]

I was 14, he was 34. I knew what I wanted so I made it obvious to him so I guess I picked him up. He started me off sucking his cock. After a couple of weeks when he saw how much I enjoyed it he told me “next time I’m gunna fuck you”. Next time he stripped me naked, ate out my hole and slathered a big wad of lube on it. He fingered it into me. That was the first time I’d ever been penetrated. He lubed his cock and put me on my belly. He got on top of me and pressed his cock on my hole. He warned me it would feel weird or uncomfortable and might even hurt a bit but he wouldn’t pull out or stop until he was balls deep and had finished inside me. I was nervous as fuck but horny as hell. He kept up the pressure until my hole relaxed and opened up and his cock slid in. He slowly pushed every inch into me. He felt fucking enormous but was probably average, about 6 inches. Once he was all inside me he stayed still until I was used to him, then he started fucking me slowly. It wasn’t exactly painful but I felt “full”. He fucked me gently for about 10 minutes then grunted “I’m gunna cum” and he shot his load into me. I loved it and it was a great introduction.

[PozToxVersPig]

19 minutes ago, Bokkierob said:

I was 14, he was 34. I knew what I wanted so I made it obvious to him so I guess I picked him up. He started me off sucking his cock. After a couple of weeks when he saw how much I enjoyed it he told me “next time I’m gunna fuck you”. Next time he stripped me naked, ate out my hole and slathered a big wad of lube on it. He fingered it into me. That was the first time I’d ever been penetrated. He lubed his cock and put me on my belly. He got on top of me and pressed his cock on my hole. He warned me it would feel weird or uncomfortable and might even hurt a bit but he wouldn’t pull out or stop until he was balls deep and had finished inside me. I was nervous as fuck but horny as hell. He kept up the pressure until my hole relaxed and opened up and his cock slid in. He slowly pushed every inch into me. He felt fucking enormous but was probably average, about 6 inches. Once he was all inside me he stayed still until I was used to him, then he started fucking me slowly. It wasn’t exactly painful but I felt “full”. He fucked me gently for about 10 minutes then grunted “I’m gunna cum” and he shot his load into me. I loved it and it was a great introduction.

Wow - similar to @Bokkierob - he was 34.  I knew I wanted to get fucked, this was 1994...dial up modems and text only chat rooms.  
I rode my bike there.  I didn't really think much it...he invited me inside, pulled down my pants, gave me head, i did the same, Jergen's almond hand lotion for lube (I can still smell it in my mind), a few minutes and I was back on my bike headed home.  I don't think either of us actually took off our clothes.
I could tell you where the house is, not who he was.  It was a shitty house by the mall and he lived in some converted garage as a renter.
It wasn't monumental for me - it was more like "breaking the seal" after which I really did never stop.  

[Bokkierob]

8 minutes ago, PozToxVersPig said:

Wow - similar to @Bokkierob - he was 34.  I knew I wanted to get fucked, this was 1994...dial up modems and text only chat rooms.  
I rode my bike there.  I didn't really think much it...he invited me inside, pulled down my pants, gave me head, i did the same, Jergen's almond hand lotion for lube (I can still smell it in my mind), a few minutes and I was back on my bike headed home.  I don't think either of us actually took off our clothes.
I could tell you where the house is, not who he was.  It was a shitty house by the mall and he lived in some converted garage as a renter.
It wasn't monumental for me - it was more like "breaking the seal" after which I really did never stop.  

Fucking hot Buddy. Do you remember how you felt as he was forcing each inch of his cock inside you? Were you hard? I was.

[Spoogebottom]

I was 20 he was in his early 50s. Really boce guy knew I was an anal virgin.  Went slow, letting me blow him while he lube. Lingered and used various toys on me.  Fucked me slowly the first time and shot a huge load of cum in me.   Spent lots of weekends at his place trading cum in our holes.  Even had a few threesomes with him and other guys.  2 of the ones I remember the most, one was a huge black guy 13-14 inch cock.  My guy held my legs back and let him hammer me balls deep. Until he came inside me. 2nd was an 18 year old virgin we got to come meet us.  He let me take the boys cherry. We got the kid to fuck us both 3 times each that day. 

[PozToxVersPig]

4 minutes ago, Bokkierob said:

Fucking hot Buddy. Do you remember how you felt as he was forcing each inch of his cock inside you? Were you hard? I was.

I have LITERALLY no recollection of that - I'm sure I was.  I remember he was wearing shitty khaki pants and a really ugly lump sweater and he was overweight white dude with bad hair.....and the smell of the Jergen's Almond lotion.

[Modestcub]

I lost my virginity when I was 19 to 37 overweight guy. We met in the park after messaging online. We kissed and sucked each other off in the bushes. We went to his place right after, there I fucked his ass and did plenty more of sucking. He's married and I still meet him occasionally. He's not big just around 5 inch

[phillygwm]

18 hours ago, Bokkierob said:

I was 14, he was 34. I knew what I wanted so I made it obvious to him so I guess I picked him up. He started me off sucking his cock. After a couple of weeks when he saw how much I enjoyed it he told me “next time I’m gunna fuck you”. Next time he stripped me naked, ate out my hole and slathered a big wad of lube on it. He fingered it into me. That was the first time I’d ever been penetrated. He lubed his cock and put me on my belly. He got on top of me and pressed his cock on my hole. He warned me it would feel weird or uncomfortable and might even hurt a bit but he wouldn’t pull out or stop until he was balls deep and had finished inside me. I was nervous as fuck but horny as hell. He kept up the pressure until my hole relaxed and opened up and his cock slid in. He slowly pushed every inch into me. He felt fucking enormous but was probably average, about 6 inches. Once he was all inside me he stayed still until I was used to him, then he started fucking me slowly. It wasn’t exactly painful but I felt “full”. He fucked me gently for about 10 minutes then grunted “I’m gunna cum” and he shot his load into me. I loved it and it was a great introduction.

So, as a practical matter, when I've been with inexperienced guys it's been a bit "messy".  I've found, as with so many other things, that getting someone's (anal) virginity is much hotter in theory than in practice.  I haven't been a guy's first in a very long time but it was hotter (though frustrating) orally.  I remember one guy -- I was maybe 20 or so and he was about 17.  We got naked and started making out.  He came from kissing before I could even touch him down there, then he panicked 😞  

I always said that a guy should be swallowed for his first time.  I love hearing about guys' early experiences and too many were when an older guy used a younger guy and left him hanging.  I like receiving no recip oral as much as anyone but I'd feel a responsibility toward making someone shoot like a volcano for their first time.

[ckskr1963]

I was 11 at the time & it was the evening after my mums funeral and my sister went to my aunts house and my uncle, dad, myself, & few other men went to my dads house. They all drank heavy and gave me a few sips here and there but it was my uncle who gave me a full stink and I was a bit light headed after. I had suck my uncles cock many times so i didn't find it odd to go into the bathroom as I thought I was going to suck him off but instead he had strip naked and lay on a towel face down on the floor. He told me it was time for me to be able to take care of dads needs now that mum was gone. My uncle used vaseline fingering my hole before he slipped his cock in and though he didn't go balls deep which was good cause he's a good 10 inches uncut, he did get enough in and blew his load and laid on top of me till he softened a bit. Once he pulled out I was told to stay where I was and then heard my dad say to my uncle "is he ready?" dad came in & fucked his load in me and though I wish it was dad who took my "V" I was to learn later that my dad was more of a bottom and my uncle was the top who took my dads "V" After dad finished he told me to get dressed and come have a drink with the others now that I was a man. Later that night I watched as dad got more drunk off came his clothes and I watched as several guys took their turn fucking dad and even though I got take a turn I was still only able to have a dry orgasm. One of the highlights of the night was watching my uncle plow my dads ass balls deep while the others watched and it seemed like it went on for a long time before he blew his load into dad. After he pulled out of dad, dads ass was almost spewing cum and my uncle told to me to eat dads ass. I don't remember falling asleep but I remember waking up to dad fucking me in his bed where I would be sleeping from then on and taking care of dads needs which I did for years and would gladly do it again as it brought us together for a special bond only those that have it with their dad can truly know.

[pnwboy18]

I was lucky enough to lose my virginity to my dad when I was 10. He was gentle and loving and it was super emotional and intense! We were both addicted after that and he started fucking me every chance we got. 

[SamBedManc]

Lost my virginity when I was 6 to a man in his 50’s… he still fucks me in his 80s!

[bbinbpark]

19 to a college senior an hour drive away in cornfields. Was a biggish dick, we had similar size and girth and when he said I was big it was a surprise to me. Hurt so good  

[yoursinmine]

35 years older. I was 18. I had been trying for years to get fucked. Couldn't make it happen. Finally got introduced to the right man by the last guy who backed out. 

He got right down to business. We met, put his hand on my head, pushed me to my knees and I sucked him hard. He has a nice cock that starts average, then swells thicker as it reaches his balls. Thickest in the middle. 

He then ate my ass doggy, fucked me after a minute or two, pushed me prone, and finished loudly in my ass. 

I've been fucking him, his friends and whomever he invites over for almost a year now. I'll take any cock, but I love older men.