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

[FanOfMrMagoo]

Well the 58yr bear, probably had some self-conscious issues,too bad,I hope that his experience made it worth it. Honesty is rare it seems when it comes to sex. Too bad the oldest one you bottomed for didn't have better self control,and the last one sounds like the best. I hope that you had more encounters with him. Thanks for replying.

We never saw each other again, he blocked me from the app where I had met him and once I found him on another app and as soon as he saw that I had looked at his profile he blocked me.
I think he even forgot that I have his phone number. It kind of put me off apps for at least 6 months. It's mostly because he was the second guy I topped and the first one had been so good that I didn't expect that.

 

[deleted784661]

We never saw each other again, he blocked me from the app where I had met him and once I found him on another app and as soon as he saw that I had looked at his profile he blocked me.
I think he even forgot that I have his phone number. It kind of put me off apps for at least 6 months. It's mostly because he was the second guy I topped and the first one had been so good that I didn't expect that.

Was that the last one? If it was the first one,he sounds desperate,the the second one,well what can I say,but the last one maybe married and DL not wanting anyone to find out. He's not worth obsessing about. I hope that you've moved on.

 

[FanOfMrMagoo]

Was that the last one? If it was the first one,he sounds desperate,the the second one,well what can I say,but the last one maybe married and DL not wanting anyone to find out. He's not worth obsessing about. I hope that you've moved on.

I misspoke a bit. I had my first time as a top with a 51 year old guy and I was 26. He told me his age and that was fine. Then I did it with this 58 year old guy. I had set a limit for myself after my first time, "never do it with a guy twice my age" and this guy had broken my limit without my consent. He told me he was 48 and he really didn't look old.
He told me that he wasn't looking for anything serious and that he liked to do it with young people in their twenties and that he was in a relationship when his profile said he was single. I moved on, it clearly wasn't worth it.

 

[deleted784661]

I misspoke a bit. I had my first time as a top with a 51 year old guy and I was 26. He told me his age and that was fine. Then I did it with this 58 year old guy. I had set a limit for myself after my first time, "never do it with a guy twice my age" and this guy had broken my limit without my consent. He told me he was 48 and he really didn't look old.
He told me that he wasn't looking for anything serious and that he liked to do it with young people in their twenties and that he was in a relationship when his profile said he was single. I moved on, it clearly wasn't worth it.

Good for you. How old are you now,and would you break your limit for an older guy if you knew he was over your limit? I bet older guys like me( 73 in a month) would be willing to give you a great time, topping or bottoming!!

 

[FanOfMrMagoo]

Good for you. How old are you now,and would you break your limit for an older guy if you knew he was over your limit? I bet older guys like me( 73 in a month) would be willing to give you a great time, topping or bottoming!!

Now I am 28 years old. I don't think I can go beyond 58 for the time being.
I also noticed with time I only want to be a top with the under 45s and be a bottom or versa with the over 45s.

 

[deleted784661]

Now I am 28 years old. I don't think I can go beyond 58 for the time being.
I also noticed with time I only want to be a top with the under 45s and be a bottom or versa with the over 45s.

Well at least you're honest,you never know though,some hot looking older guy with a nice cock...

 

[deleted784661]

Well at least you're honest,you never know though,some hot looking older guy with a nice cock...

Okay, anyone else have something to say? I'm hoping for an arousing story about someone older,please give details!!!

 

[mango_twinkie]

I accidentally fucked someone who was 10 years older than me. I was 19 at the time. I was pretty new to all things sex, I was a virgin, and the only thing I'd done before this was got head, but I wanted to get laid, so I got on Grindr and found a guy who looked young, pretty hot, and hung and asked him to come over. It was my first time bottoming and he was 7in at least. It started like all hookups; we made out and undressed each other. then I took him into my bedroom where we 69ed (this was also the first time I put a dick in my mouth, and 7in is a lot for a newbie). He wasn't at the best angle to suck my dick so I sat on his chest and he started sucking me while I drilled my cock down his throat until I came. He swallowed all of my cum and then flipped me back around so we were back in 69; instead, this time, he was rimming me and prepping my hole with his finger. Soon after, he had me on my fours and he fucked me bareback, doggy style. No lube, no condoms, just his spit and precum keeping my tight hole from skinning his dick. It was painful, as it was my first time, and I kept whimpering "stop" and tried pushing him out, but that just seemed to rile him up and got him going faster and harder until he came in deep inside me. He tried rimming me and opening me up to lick his cum out, but I closed up so tight after that and I ended up carrying his load to school that day, too lol.
It was a great fuck, only downside was him lying about his age when we met. He told me he was 22 but when I saw his profile on hinge a couple weeks later, I found out he was actually 29. And that's how I accidentally fucked someone 10 years older than me.
(P.S. I don't mind fucking older men, hell, I prefer mature guys. Just don't lie about it, lol. If I think you're hot, then you're hot)

 

[deleted784661]

I accidentally fucked someone who was 10 years older than me. I was 19 at the time. I was pretty new to all things sex, I was a virgin, and the only thing I'd done before this was got head, but I wanted to get laid, so I got on Grindr and found a guy who looked young, pretty hot, and hung and asked him to come over. It was my first time bottoming and he was 7in at least. It started like all hookups; we made out and undressed each other. then I took him into my bedroom where we 69ed (this was also the first time I put a dick in my mouth, and 7in is a lot for a newbie). He wasn't at the best angle to suck my dick so I sat on his chest and he started sucking me while I drilled my cock down his throat until I came. He swallowed all of my cum and then flipped me back around so we were back in 69; instead, this time, he was rimming me and prepping my hole with his finger. Soon after, he had me on my fours and he fucked me bareback, doggy style. No lube, no condoms, just his spit and precum keeping my tight hole from skinning his dick. It was painful, as it was my first time, and I kept whimpering "stop" and tried pushing him out, but that just seemed to rile him up and got him going faster and harder until he came in deep inside me. He tried rimming me and opening me up to lick his cum out, but I closed up so tight after that and I ended up carrying his load to school that day, too lol.
It was a great fuck, only downside was him lying about his age when we met. He told me he was 22 but when I saw his profile on hinge a couple weeks later, I found out he was actually 29. And that's how I accidentally fucked someone 10 years older than me.
(P.S. I don't mind fucking older men, hell, I prefer mature guys. Just don't lie about it, lol. If I think you're hot, then you're hot)

IMHO,honesty is the best thing for anything,thanks for replying.

 

[PutItInHere691]

I was 22 he was 64….. I mowed his neighbors grass and one day I saw him on porch.. the grass around his yard was at least a feet high.. the guys grass that I just got done mowing .. David.. tells me his age (which didn’t look 64. I was thinking more like 50.. but I wasn’t good at guessing ages..
David says he lost his spouse about 5 years ago.. he used to keep it mowed and one day he just quit..I told David see him next week and loaded up my truck and pulled up the man’s driveway .. I went to talk him about doing his yard.. he says it didn’t need mowed .. I told him I’d do it free of charge he was like free as if he was asking me if that’s what I said .. I said got my jobs done for the week he says ok if I wanted to waste my time. I can do it.. .. I used a weed eater cut it down so far then took a rake cleaned it up and checked for anything the the grass then set my riding mower up high. Mowed it once. The lowered it some more and finished mowing it ..
He comes back out on the porch tells me have a seat while reaching me bottle of pop…. Root beer .. it was nice and cold. .. he says thanks .. that he didn’t remember it looking that nice when mowed.he brings up ever since he lost his better hall he wasn’t in the mood and time and time again

so when I mowed David’s grass I mowed hi.. on a riding mower it didn’t take long .. so I’d mow his yard and visit with him as his kids moved away to live their lives..he had two sons when he was with a woman years ago ) he had a few friends that came around but not often..

one week I mowed his grasss and it began pouring the rain.. he says get on the porch .. I got there and told him couple more swipes and I’d be done.. he says it happens.. and went back into the house and told me to follow him .. I took my shoes off and socks as they were soak n wet ..

I looked around at pics of his sons and I was looking at a pic with two guys on it.. I said his sons were quite handsome.. he said that not his boys that’s him and Richard.. I thought wow..

I said how old are you in that pic he said 34 .. I was like damn you look much younger than that .. as we went back through the house there was a record playing some soft music .. he said that was richards face song.. said they’d hold each other .. how he missed those days..

I reached my hand out he looks at me kind of shocked ..as he took my hand.. he made it a point to remind me the differences in age.. and I said age is just a number isn’t it .. he says that’s true.. and I said besides it’s just a dance ..

I wrapped my arm around him and held his hand and stood about same place he kept looking at my chest .. to reach down pulled his shirt up and over his head and pressed our chests together and I pour my arms over his shoulders .. I asked him how did it feel.. he says felt nice.. and rested his head against my chest

TBC ..
xbbxbxbxbbxxbx

 

[PutItInHere691]

Part 2

as we were dancing around I felt movement In my crotch.. I stepped back he looked down.. I said sorry.. he says is his old ass getting me excited.. I told him it has a mind if it’s own.. .. he mentioned it’s been so long .. since he has seen one other than his own.. I told him go ahead .. I guided his hands to top of my shorts and let go .. told him it needs out to dry off anyway..

He slid my shorts and underwear down some and I let them go to the floor and kicked them aside .. he saw my dick and was like wow .. .. takes it in his hand stroked it few times.. .. he kneeled down and took it in his mouth and his mouth felt so warm inside.. and one things for sure.. it may been while since he sucked a dick.. but he surely didn’t forget how..

I said let’s go over here.. I sat on couch he got on his knees and began sucking again.. time to time. Sucking ny balls.. as well.. he took off his clothes and his body was still tight with a little muscle outline and a nice dick.. I sat up and sucked his dick swallowed every inch of it as I played with his balls as I did..

He was so excited he began cumming and cumming fast powerful shots and I tried to keep up with it but some oozed out side of my lip..

He then gets on top of me spits in his hand few times lubing my dick.. and as it went inside him.. he was so tight .. .. and all he can do is look in my eyes. And tells me thanks he been wanting this a long time as he begins to ride my dick speeding up at his pace ..

He kisses me on the forehead and asked if I’d shoot inside him.. I looked at him and told him I’d let him know when it cums .. few minutes later I told him and he holds still feeling my cock throbbing then shooting g inside him.. ..

I put my shorts on saw it had quit raining .. told him be couple days before finish mowing it..

so I’d go to David’s now his grass go next door.. go inside fuck him .. sometimes more than once ..

October came along and I wasn’t mowing grass anymore rest of the year but I’d go visit him do whatever he wanted .. the last time I went he had a buddy with him .. his new boyfriend.. he thanked me for showing him that he still had more to do in this life

and I visited time to time but no sex occurred.. he was in love again and this guy was little closer to his age than I was .

 

[deleted784661]

Part 2

as we were dancing around I felt movement In my crotch.. I stepped back he looked down.. I said sorry.. he says is his old ass getting me excited.. I told him it has a mind if it’s own.. .. he mentioned it’s been so long .. since he has seen one other than his own.. I told him go ahead .. I guided his hands to top of my shorts and let go .. told him it needs out to dry off anyway..

He slid my shorts and underwear down some and I let them go to the floor and kicked them aside .. he saw my dick and was like wow .. .. takes it in his hand stroked it few times.. .. he kneeled down and took it in his mouth and his mouth felt so warm inside.. and one things for sure.. it may been while since he sucked a dick.. but he surely didn’t forget how..

I said let’s go over here.. I sat on couch he got on his knees and began sucking again.. time to time. Sucking ny balls.. as well.. he took off his clothes and his body was still tight with a little muscle outline and a nice dick.. I sat up and sucked his dick swallowed every inch of it as I played with his balls as I did..

He was so excited he began cumming and cumming fast powerful shots and I tried to keep up with it but some oozed out side of my lip..

He then gets on top of me spits in his hand few times lubing my dick.. and as it went inside him.. he was so tight .. .. and all he can do is look in my eyes. And tells me thanks he been wanting this a long time as he begins to ride my dick speeding up at his pace ..

He kisses me on the forehead and asked if I’d shoot inside him.. I looked at him and told him I’d let him know when it cums .. few minutes later I told him and he holds still feeling my cock throbbing then shooting g inside him.. ..

I put my shorts on saw it had quit raining .. told him be couple days before finish mowing it..

so I’d go to David’s now his grass go next door.. go inside fuck him .. sometimes more than once ..

October came along and I wasn’t mowing grass anymore rest of the year but I’d go visit him do whatever he wanted .. the last time I went he had a buddy with him .. his new boyfriend.. he thanked me for showing him that he still had more to do in this life

and I visited time to time but no sex occurred.. he was in love again and this guy was little closer to his age than I was .

Wow,what a story,it's good that he realized there is still life after loss. Thanks for sharing.

 

[fuckee]

The oldest man that has fucked was 72. I was my thirties at the time so could really have been my dad. But the interesting thing was that for him it was the first time ever to fuck a man or a boy. He was married and a father and grandfather. His wife had health problems and I believe it was a long time ago that he ever had sex. We had been in touch through a forum about men wearing shorts. Like him I am very fond of traditional leather shorts. He had posted some photos where you could only see his legs, but they looked good. I didn't know what his age was. I had posted some photos of me in my leather shorts.

But also this one shirtless with my shorts open.

And one where I was fingering my hole.

He liked them very much and told me that he would be curious to fuck me in the ass, although he had never done it before. I was a bit surprised when he told me that he was already over 70 of age. However it was something of a thrill to have sex with a man who was so much older than me.

When I was young I had that thing for older men. First I thought men of 30 were older, but very fast I also tried men in their forties and then fifties. And I remember very well when I had my first man of over 60. He had white hair but a hot athletic body and was very much into jockstraps. He fucked me while we both wore jockstraps.

But crossing the line of 70 was a new step. When I met him he did look a bit older than I had had expected but not bad. Of course he had grey hair but he had a nice built. And in the hotel he sucked my cock and then fucked me. I had prepared myself well. I had shaved my ass, given myself an intense enema and had fucked myself with a dildo. He was already rock hard and put a condom on his cock. Although he had never done it his cock went in like nothing! And boy, he was moaning of joy. The only thing that was a bit of a pity was that already after a few minutes he had an orgasm. He apologized a little bit for it. Then sucked my cock until I came into his mouths. For a long time I lied naked on him while he caressed my body and my hair and he told he told he had never felt as good before. Well, that is a compliment from a guy of 72.
Then he had to go back to his wife. We exchanged some messages but we never met again. Still, I felt a bit proud that I had given him that special experience!

 

[fuckee]

Also the oldest men that I had ever fucked was a special story. He was 53 and a German army officer, divorced with an adult son. I was 37. He was not handsome in a classical way but very masculine and it was my first time with a military man. I do have a thing for men in uniform.

And he was quite a sex pig. On the one hand he was crazy for my piss. I had to piss over him and into his mouth. I was quite new to wet games but I loved it very much. Moreover he was crazy about ass play. We played with all kinds of toys that I had brought. The highlight was when we played with a double dildo. This is not a picture of us, but it showed what we did.

The dildo was not that big, but we enjoyed fucking each other with the dildo going in further and further until our butts touched each other. We had taken it completely up our asses!

First I was a bit disappointed when he told me that he was not a fucked but he compensated it completely with his fingers. He was really crazy about fingering me and spreading my hole wider and wider. First one finger, than a second. Then I asked for a third. I had never had so much up my ass, but I could take it and I loved it. Then without asking he put in a fourth finger. And finally a fifth! I had never thought that I could take that much! It was very close to fisting, but he didn't go that far.

And then he asked me to fuck him in the ass. Normally I am rather a bottom and when I had fucked in the past it was rather with guys who were younger than me. But I was so horny that I loved to fuck him. And in the end I shot my load up his ass!

We did more naughty things the weekend that I was with him. After midnight we went for a walk throught the village where he leaved. We only wear a tanktop, shoes and socks. Our cocks and asses were naked, but he didn't care for the neighbours!

We only met once and I have written to him a couple of times. He was not only the oldest man that I have ever fucked but also one of my hottest experiences!

 

[Srome2808]

The oldest guy I've been with was a guy I met online who was 72. He invited me over to have some wine with him and I ended up staying the night with him. We didn't end up doing much except oral, since apparently he had a partner of 40+ years who lived overseas.

The next oldest guy I met was a guy thats 64. Very nice guy. Nice dick with a huge head. Apparently he usually would be a top but not this time around. We started by making out, oral and rimming. It got to the point where he was enjoying himself so much he asked me to fuck him. So after I had rimmed him, had a beautiful hairy hole, i flipped him around and I slowly inserted myself and fucked him. His ass up in the air, arched his back and I just went to town on his ass. It felt so good and he ended up cumming while I was fucking him. He ended up sucking me off and I came.

I've always been more attracted to older guys, usually guys twice my age. I don't usually go for guys my age, currently 32. Nothing wrong with younger just a preference for older.

 

[PutItInHere691]

Oldest I been with .. he was 55 .. I was 24… I had put a sign up on bulletin boards seeking work.. will do anything from mow grass to painting g fences .. cleaning up yards and so one ..

a few guys called wanted grass mowed and weed eating done .. one guys house had this older guy lived in house next to him. Almost looked like no one lived there .. all junked and and grass was so tall came to my waist . ..


he tells me older guy lived there.. his wife passed away few years ago and since then the place had gone to crap….

one day I was bored and nothing to do.. so went to the older guys house knocked on his door.. few minutes later he opened the door I told him my name .. Lance … told him I do yard work .. and he says he’d like to get it done but didn’t have the money to pay for it ..

 

[PutItInHere691]

The oldest man that has fucked was 72. I was my thirties at the time so could really have been my dad. But the interesting thing was that for him it was the first time ever to fuck a man or a boy. He was married and a father and grandfather. His wife had health problems and I believe it was a long time ago that he ever had sex. We had been in touch through a forum about men wearing shorts. Like him I am very fond of traditional leather shorts. He had posted some photos where you could only see his legs, but they looked good. I didn't know what his age was. I had posted some photos of me in my leather shorts.

View attachment 98195711
But also this one shirtless with my shorts open.
View attachment 98195811
And one where I was fingering my hole.
View attachment 98195881
He liked them very much and told me that he would be curious to fuck me in the ass, although he had never done it before. I was a bit surprised when he told me that he was already over 70 of age. However it was something of a thrill to have sex with a man who was so much older than me.

When I was young I had that thing for older men. First I thought men of 30 were older, but very fast I also tried men in their forties and then fifties. And I remember very well when I had my first man of over 60. He had white hair but a hot athletic body and was very much into jockstraps. He fucked me while we both wore jockstraps.

But crossing the line of 70 was a new step. When I met him he did look a bit older than I had had expected but not bad. Of course he had grey hair but he had a nice built. And in the hotel he sucked my cock and then fucked me. I had prepared myself well. I had shaved my ass, given myself an intense enema and had fucked myself with a dildo. He was already rock hard and put a condom on his cock. Although he had never done it his cock went in like nothing! And boy, he was moaning of joy. The only thing that was a bit of a pity was that already after a few minutes he had an orgasm. He apologized a little bit for it. Then sucked my cock until I came into his mouths. For a long time I lied naked on him while he caressed my body and my hair and he told he told he had never felt as good before. Well, that is a compliment from a guy of 72.
Then he had to go back to his wife. We exchanged some messages but we never met again. Still, I felt a bit proud that I had given him that special experience!

Very sexy .. wished that was my finger in that hole next to my tongue hehe

 

[twinkerbelled]

The oldest I've bottomed for was probably mid 50s (I'm not totally sure) while I was 18. The oldest I've topped for is 28 while I am currently 22.

The guy in his mid 50s was this big hair bear-ish biker guy from my hometown that I would regularly hookup with when I came home from college during the summers. It was a regular thing to look forward to up until last year when I graduated college and moved out on my own (and now I'm in the real world and don't get summer break anymore rip).

The guy I topped for was very special, because I don't get a lot of guys (especially older men) willing to let me top being a 22 year old asian twink. So there is just a lot of expectations when guys hit me up. So, it was a lot of fun, and we've been hooking up off and on for the last couple of months.

 

[somedudewhosplaingay]

when i was 23 i got fucked by a hook up with a 71 year old bear, he was hot, hung and kinky

 

[RugbyGuy42]

The first find he would have been early 60s when I was early 20s.

A lot of my early sexual encounters happened at my local leisure/sports centre. I discovered that the open showers were a great place to meet, mostly older, guys.

Then I discovered the separate spa area they had and that half the week was mixed and half was single sex sessions. As I started going to those men only times I soon discovered the regulars, the ones who turned up regularly. Though some were in their 30s/40s the majority were older particularly during the week.

A nice thing about that was you soon knew who was safe and therefore you'd be able to get off with a guy in front of the other regulars. Me and a sexy daddy bear used to really go for it while the other regulars would watch and stroke.

The guy in his 60s was a real gym goer and maintained a great body with a nice level of hairiness. I'd seen him around but the first time something happened was on a quiet week day when I was sitting in the steam room on my own thinking of leaving as there was no one around.

He came in naked, which was usually a sign they were interested as the straight guys often kept towels or shorts on and sat, not right next to me but also not that far away given we were the only guys there.

I was pretty keen and confident he was up for something so didn't waste time with the usual eye contact, subtle stroking dance and to my delight he responded and we were both soon obviously hard. Moving over to him we kissed and stroked each other. I was delighted with the size of his hard cock, particularly the thickness. As there was still no sound of anyone else coming into the spa area I slipped onto my knees in front of him and after an initial struggle took his whole cock in my mouth. He was clearly really enjoying it, his fingers running through my hair and his moans and occasional murmurs of that's it boy, suck it.

Soon I could feel he was near and I eagerly picked up the pace and was rewarded with a loud moan and a nice big load to swallow. When he was done he pulled me to my feet and reached out and started to stroke me again. Between the heat and the load in had just taken I didn't last long and soon I shot my load all over his body and face. He stood up and we kissed, him tasting himself on my lips and my feeling my cum on his body rub against mine. We then headed for the showers and kissed a bit more before someone else came in.

After that I would see him for for to time and we would play when we could, though he was generally only up for it if no one else was around even if it was other like minded guys. Then one time it was quite busy so limited chances of anything happening and in one brief quiet moment he asked if I wanted to go back to his to which I instantly agreed.

He drove us back to his which wasn't far and we were on each other soon after getting through the door. Taking me upstairs we were soon naked and it was nice to have more time to admire and explore his older but well maintained and hairy body. As we got down to it his fingers were often straying to my hole so I asked if he wanted to fuck me and he was soon eagerly lubing me up and slowly sliding his hard thick cock inside me. My legs were over his shoulder as he pounded my eager hole, I remember him saying 'fuck you're so tight boy, I'm not gonna last long' and so he didn't, pulling out to spray me with his load.

As we lay there after he had wanked me off I found a bit more about him. He had come out late in life, splitting from his wife around 10 years earlier, and had three kids. One had just been visiting with his grandchild so he hadn't had much opportunity to have fun hence why he'd been so horny and invited me back.

After that we met irregularly for a few years, sometimes at the spa and others he's just invite me over for fun. So last time he fucked me he would have been around 66.