Who's the oldest you've fucked,top/bottom give details

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deleted784661

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I'm curious, who's the oldest you've fucked,as a top or a bottom. I'd love to hear the details. Would you fuck him again? Was he as good as a twink or other younger guys you've been with? Rate the fuck.
 
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1373263

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Oldest for me would have to be a 77 year old guy a friend introduced me to. I visited his house at his invitation and one thing led to another; after a few mutual touches he stripped my clothes off, sat me down on a daybed in his sunroom and proceeded to give me a leisurely sponge bath. He was very thorough and gentle, and after about 20 minutes I was rock hard. It wasn't long before he took my cock in his mouth ad proceeded to give me one of the best blowjobs I have ever experienced; every time I got close to blowing he would back off with a teasing look and after half an hour I was begging him to finish me. He kept me going for another couple of minutes before he sucked me totally dry.
 
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deleted784661

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I'll take sucking, sounds great. Did you ever fuck him or get fucked by him?
 
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deleted784661

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Oral works for me, anybody else want to chime in about who's the oldest that you've fucked,top or bottom? Rate and give some details, inquiring minds want to know!
 
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1373263

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I'll take sucking, sounds great. Did you ever fuck him or get fucked by him?
Yes, we regularly got together and generally he would spend his time sucking me dry- he didn't want to be sucked very often. He wasn't really interested in fucking me but as my confidence grew I started to play with his arse as he blew me, until one day he asked after swallowing a week's load if I wanted to fuck him.
His arse was velvet smooth the first time I fucked him and he was very receptive; in time things developed to the point where I could be lazily fucking him on the bed in the sunroom for up to 35 minutes after he had blown me.
 
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deleted784661

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Yes, we regularly got together and generally he would spend his time sucking me dry- he didn't want to be sucked very often. He wasn't really interested in fucking me but as my confidence grew I started to play with his arse as he blew me, until one day he asked after swallowing a week's load if I wanted to fuck him.
His arse was velvet smooth the first time I fucked him and he was very receptive; in time things developed to the point where I could be lazily fucking him on the bed in the sunroom for up to 35 minutes after he had blown me.
Did you make him cum? Sounds like you had a nice fuck buddy. Whatever happened to him? And how long did it go on? Did he ever top you?
 
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1373263

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Did you make him cum? Sounds like you had a nice fuck buddy. Whatever happened to him? And how long did it go on? Did he ever top you?
We met regularly for nearly two years before he had a stroke, didn't recover well and had to go into care; he has since passed. He sometimes got hard but not reliably and he didn't always ejaculate, but we were both aware when he had cum by his muscle spasms.
I wasn't aware he was into cock when I first visited (my friend knew) but he gave subtle signals to the point where I wasn't surprised when he reached over and started to unbutton my trousers. I didn't say anything and he continued, unzipping my fly and gently touching my cock. We looked at each other for a moment before he encouraged me to stand up and remove my shorts; I was hardening quickly. As I removed my shorts he went into the kitchen and returned with a basin of warm water before proceeding to unbutton my shirt and slip my underpants off.
He made some encouraging comments as he touched me, and then started to wash me with a facecloth and warm water; I didn't quite know what to do so just stood there, initially awkwardly before I started to relax and enjoy what he was doing. After 5 minutes and a very through wash he invited me to lie on the sunbed; when I did so he proceeded to wash me again with the facecloth but paid attention to my cock, arse, chest and shoulders. I was on my front and he had just been washing between my legs when he stopped and encouraged me to roll over. I was very relaxed by this stage and when I rolled over, he knelt on the floor and took my dribbling cock in his mouth, subtly working me to the point where I was sure I was going to cum, and then backing off. He did this over and over again until I was sure something was going to break, and then out of the blue he kept going, taking my load in his mouth and sucking me until I couldn't take any more.
 
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deleted784661

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We met regularly for nearly two years before he had a stroke, didn't recover well and had to go into care; he has since passed. He sometimes got hard but not reliably and he didn't always ejaculate, but we were both aware when he had cum by his muscle spasms.
I wasn't aware he was into cock when I first visited (my friend knew) but he gave subtle signals to the point where I wasn't surprised when he reached over and started to unbutton my trousers. I didn't say anything and he continued, unzipping my fly and gently touching my cock. We looked at each other for a moment before he encouraged me to stand up and remove my shorts; I was hardening quickly. As I removed my shorts he went into the kitchen and returned with a basin of warm water before proceeding to unbutton my shirt and slip my underpants off.
He made some encouraging comments as he touched me, and then started to wash me with a facecloth and warm water; I didn't quite know what to do so just stood there, initially awkwardly before I started to relax and enjoy what he was doing. After 5 minutes and a very through wash he invited me to lie on the sunbed; when I did so he proceeded to wash me again with the facecloth but paid attention to my cock, arse, chest and shoulders. I was on my front and he had just been washing between my legs when he stopped and encouraged me to roll over. I was very relaxed by this stage and when I rolled over, he knelt on the floor and took my dribbling cock in his mouth, subtly working me to the point where I was sure I was going to cum, and then backing off. He did this over and over again until I was sure something was going to break, and then out of the blue he kept going, taking my load in his mouth and sucking me until I couldn't take any more.
Thank you for sharing this with me. I'm sad for you that he passed.
 

rm1128

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disillusioned by any and all kinds of relationships with my contemporaries, the summer I graduated college (at 21) I fully indulged in my attraction to older men. up until then, I had only been with generational peers but sex with them started to feel too superficial and almost competitive at times. I felt self conscious. my foray into a wider range of partners, older men in particular, taught me so much about myself and what sex could be.

I've actually written about some of these hookups maybe I'll blog them but I just generally loved the way older guys were more communicative, sensual and slower, more indulgent. I was also was able to share my own inexperience ( I had only been sexually active for like 3 years at that point) with them without being judged and several guys took time to teach me stuff, which was hot tbh.

the oldest person I've hooked up with was in his 60s and I was 21 at the time. I was extremely horny and deliberate in my quest for someone older lol. this person happened to be available and we had an afternoon tryst I often think about still. He was an older white gentleman with gray hair (all over) which I found to be so sexy. He was clean and natural. He was soft spoken and easy going. He let me really take the lead that day and that made for an extremely sexy dynamic considering I was the novice.

an expectation of mine for hooking up that day, was to finally bottom. because of the couple of hookups with older dudes that took place before this one, I realized how much more at ease I was with a mature partner. I had always heard that you gotta relax when bottoming so, I figured what better partner than one that I am at EASE with. I never accomplished my goal of stuffing my hole that day. but ultimately I didn't care because we had so much otherwise. In fact he wasn't hard for a lot our time together and i didn't mind. I still thought him extremely sexy, giving and open. I actually find flaccid cock hot too. I remember his fluffy white pubes being a big turn on for me. I found myself burying my face in his pubes and pits a lot.

He looked older with clothes on if that makes sense. probably because his style really dated him. I remember thinking his body looked younger than his face which is sooo something a 21 year old would think smh. he had an average build with a slight belly that i adored. he was bald except for the temples and had a little bit of stubble which I loved. he was an amazing kisser. And because I hosted in my empty house and had the whole day to myself, I spent most of the time naked while he would dress himself whenever we weren't in the bedroom (he took smoke breaks). the whole clothed vs nude thing turned me on a lot.

My biggest takeaway from meeting him the one and only time was seeing how liberating sex can be when the goal is pleasure and not strictly escapism or dominance or whatever else I had known it to be up until then. He let me be myself and that was so hot. especially bc I was having body image issues at the time (and i was such a snack smh) and he was so obsessed with mine for whatever reason and I thought his totally sexy without any stigma about it regarding age or whatever. He never came and neither did I. I had just been dripping LOTS precum throughout, which he couldnt get enough of, constantly cleaning it up with his mouth. And I remember learning then that sex didn't always have to end with orgasm. Wish we got to do one more time before I left town, but it's ok.

in terms of "fucking" tho.... one of my "daddy" hookups made me top him and that was my first time topping. it wouldve been hot except for the fact that he had snuck me into his marital home and I found myself fucking him in a room full of family portraits. he was an Indian cab driver and didn't talk much. Even so, he was commanding and it felt very intense and a little rushed and obviously risky (it was an AM hookup in the middle of the work week). because of that, topping him felt like a lot pressure. So yes, I was hot and hard and sticking my dick in someone for the first time was AMAZING but his silence and my brandnewness made me feel like I had to perform in a certain way.

pretty much I got in my head. I tried communicating to him that I wasn't going to cum like this, thinking maybe it was the doggystyle we were doing but idk what he understood because next thing I know, he turns around, yanks the condom off, lays on his back, flips he legs up and drills my dick back in him. Writing it down, I realize how problematic it was. And I for sure knew I didn't want to be fucking raw but I had admit it felt so much hotter. Even with the changes I knew I wasn't cumming anytime soon and by that point I had broken into a sweat. I guess the pressure was on for him too, bc he sort of sits up a bit still me still inside, rubs my sweaty belly and chest and kind of pulls away. letting me know it's ok to stop. He then takes my throbbing dick and sucks me off.

he was amazing at oral but didn't really allow me to do it on him. in fact this guy never got hard either, which again is fine but he was definitely strictly a giver and made no space for me to please. except for my rock hard virgin dick that at the time could become erect at the gust of mild breeze, so it wasn't that surprising that I could fuck and still not get off... He was nice enough. He finally let me kiss him as we showered together. That was probably also where my lil shower fetish manifested, as I found it extremely sexy to be washed/bathed my another.

Anyway. this was fun to reminisce about. I haven't had sex in a while and I myself am a bit older now. Idk how the whole older younger thing would play out these days. I dont have a type and I'm not opposed to going younger I just never have. I hope the dads and grandads would still have me and didn't just hookup with me at a time when I was just barely grown haha. only time will tell
 
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deleted784661

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That was very interesting,a nice long story with details. Just what I was looking for. I like hearing about other's experiences and thank you for sharing. Especially like your thoughts about sex,and the fact that it doesn't always end in orgasm.
 
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deleted784661

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Wow , must've been a good stretch for you and a good time! Hope that you both had a happy ending. Did you cum hand's free?
 

integritymatters

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I'm curious, who's the oldest you've fucked,as a top or a bottom. I'd love to hear the details. Would you fuck him again? Was he as good as a twink or other younger guys you've been with? Rate the fuck.
Oldest is 41 (as a top and bottom).
Youngest as a top is probably 24 (I was 19 at the time, he was 24 - then again, I've dated so many guys I've lost count).
 
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Oldest is 41 (as a top and bottom).
Youngest as a top is probably 24 (I was 19 at the time, he was 24 - then again, I've dated so many guys I've lost count).
Thanks for the reply. Maybe you should try expanding ( pun intended) your experiences. Let me know when you hookup with a senior citizen,42 is just a kid compared to me at 72!!
 
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integritymatters

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Thanks for the reply. Maybe you should try expanding ( pun intended) your experiences. Let me know when you hookup with a senior citizen,42 is just a kid compared to me at 72!!
You're too funny!
And you're welcome.
Actually, after that "experience" a few years back with the older guy, I discovered I'm a top and I date y*un*er.

It's been 2 years, but since I'm poly and date long distance, I haven't had any action since 2021.
I'm 26, turning 27 in August - time is speeding by, and I'm getting older.
I have 1 boyfriend, who lives in Argentina (he's 23) - he's wonderful and always has been.

But I always find that more and more YouTubers are my type......
It's been awhile since we've been poly, so I think it's time we expand our dating pool.
72 is a little extreme (health insurance saves lives), but maybe dating a few years older than me - or even maybe a European guy - is something I'd be open to, for second and third boyfriends.

I've flirted with many European guys, but it never went anywhere besides that.
So I don't know.
 
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You're too funny!
And you're welcome.
Actually, after that "experience" a few years back with the older guy, I discovered I'm a top and I date y*un*er.

It's been 2 years, but since I'm poly and date long distance, I haven't had any action since 2021.
I'm 26, turning 27 in August - time is speeding by, and I'm getting older.
I have 1 boyfriend, who lives in Argentina (he's 23) - he's wonderful and always has been.

But I always find that more and more YouTubers are my type......
It's been awhile since we've been poly, so I think it's time we expand our dating pool.
72 is a little extreme (health insurance saves lives), but maybe dating a few years older than me - or even maybe a European guy - is something I'd be open to, for second and third boyfriends.

I've flirted with many European guys, but it never went anywhere besides that.
So I don't know.
You might be interested to know that some of us ",oldies"have inflatable implants. We stay hard as long as we want. I think we try harder to please. If you find someone older , who's versatile,you might get the fuck of your life!!
 

integritymatters

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You might be interested to know that some of us ",oldies"have inflatable implants. We stay hard as long as we want. I think we try harder to please. If you find someone older , who's versatile,you might get the fuck of your life!!
Well, you just reminded me of my crush on Ricky Martin.
He's 50-something and still hot.
Lance Bass too - I'd still let him bottom for me (if he is a bottom).
I'm very picky about the older men I'm into.
There's very few.
I suppose what turned me off to older men initially is not the sex itself; the guy was very rude, short-tempered, cheated on his girlfriend with me (something he deliberately only told me after the sex).
There were too many red flags.

He and I are two different people.
I'm patient, calm, open minded, intellectual - but all of that went out the window when he started screaming at me.
My mom (who's 60 herself) used to tell me to never date older men because, "They'll control you! Date someone your age!"
This coming from the woman who married my father (who was 8 years older than she).
A little hypocritical of her to not take her own advice!
 
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Well, you just reminded me of my crush on Ricky Martin.
He's 50-something and still hot.
Lance Bass too - I'd still let him bottom for me (if he is a bottom).
I'm very picky about the older men I'm into.
There's very few.
I suppose what turned me off to older men initially is not the sex itself; the guy was very rude, short-tempered, cheated on his girlfriend with me (something he deliberately only told me after the sex).
There were too many red flags.

He and I are two different people.
I'm patient, calm, open minded, intellectual - but all of that went out the window when he started screaming at me.
My mom (who's 60 herself) used to tell me to never date older men because, "They'll control you! Date someone your age!"
This coming from the woman who married my father (who was 8 years older than she).
A little hypocritical of her to not take her own advice!
You've got a point there,at any age , it's the attitude that usually kills things,and the fact that there's no honesty. If you look at the porn actors on Hotoldermale, I think they're hot,even if they're acting. I guess that if you use your intuition and red flags show up, don't be used. My dad was 19yrs older than my mom. I didn't see anything wrong with it. You sound like a thoughtful , considerate person.
 
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