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Speak Out: What’s The Best Experience You’ve Had With An Older Man?

Image credit: Tom Daley’s Instagram @tomdaley1994

Earlier this month, Tom Daley opened up to the Belfast Telegraph about his relationship with Academy Award-winning screenwriter Dustin Lance Black. Daley and Black had gotten married earlier this year after announcing their engagement a year ago in the Times.

Of course, one of the things that the couple had to weather was the 20-year age difference between the two of them. At the time they first met, Daley was only 18-years-old and Black was 38. At the time of their marriage, Daley was 22 and Black was already 42.

Daley talks about the difference in the Belfast Telegraph interview, saying: “I don’t really think about age and we never notice the age gap.” Further on, he proclaims that “Being with Lance has been the best thing that’s happened in my life. It’s very exciting moving forward and it’s nice to be in love.”

While Daley and Black may be the most recognizable May-December gay couple at the moment, it’s not like they’re the first to have one. If our post “Hot or Not: Older Men” is anything to go by, lots of mature Adam4Adam members are hooking up with guys half their age. There’s also something to be said about the fact that a lot of gay men’s fantasies involve finding a “daddy”.

Taking the cue from Daley and Black’s relationship, we want to hear from you younger Adam4Adam readers. What’s the best experience you’ve ever had with an older man? Is it something you’re still looking for until today? Don’t be shy, we’d love to hear your stories! Share your stories with all of us in the comments section below!

There are 30 comments

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  1. West

    I have not yet had a good, fulfilling, democratically inclined (good and fulfilling), human experience and therefore have grown to appreciate catastrophe. I would spare all the patriarchs per my own interpretation of reality but should the have to go to hell for what the majority is so be it. Of course you could always man up, I can teach you how boys. Amen.

  2. Joe

    I met my first real love at 23 and he was 56 and he was the best I ever had. He was lean and thin with a good size and very firm dick! He knew how to use it and was a very good lover. He did not use viagra or any of those drugs to keep it up either.. He died at 75 and 2 years before he died I paid a visit and he would not let me leave until I gave him some head.he still had it going on. I am 62 now and I would go with a older guy if he is healthy and in good shape

  3. B

    Nothing out of the ordinary but when I was in the military (21) I met a far older man (late 40s?) who was a high ranking officer of a different branch. He was really handsome, muscular, and rather wealthy compared to me.
    He liked me a lot and took me to his jacuzzi where we drank and he gave me a naked massage. When we had sex he had a huge dick and knew how to eat my ass perfectly lol. We had fun till I moved to my next station.

  4. secretary cuttlefish

    Gay mens’ fantasies involving a daddy just lays bare their own unfulfilled psychological needs with their own father s growing up, likewise for women. When some people give in to it others will prey on it. Once you grow up it takes on this illusion of love by the underlying issues are still there.

  5. hotmale4u32801

    One of my best experiences was in Hawaii with his daddy! I was 24, he was in his 50s, a tennis instructor had a sexy speedo tan lines! We met on A4A, I was there on business and only had a random hours I can play though I was there for a week he didn’t come by till the fourth day. I told him I wanted to try to bottom, I have tried many times before then. He took his time and was able to loosen me up he missed a pound of me for hours that night. And came back every night after that. It was the most amazing session I have ever had

  6. Nolaron

    I’m the older side of your equation. The problem with the May-December situation most of the time is too many younger guys are expecting a “sugar” daddy. I get along with younger guys and all my friends are younger but too often the ones that are wanting to have a sexual relation want Daddy to take care of them. I want a 50/50 relationship!

  7. rodney

    When he took my anal cherry at age 18. I’m now 41 and I still have a thing for older men or men my age. I still love to bottom.

  8. HunterWI

    How about “What’s The Best Experience You’ve Had With A Younger or an Older Man?”

    What does a one-way younger vs. older view have to do with what’s “Best”?

    The focus for the question here comes from a gay man stereotypical bias where everyone is young, urban, and trendy and encounters are only of the “Once and Done” variety in which the younger is the only perspective that matters.

    Gay guys come in types FAR beyond just that.

    So how about a REAL question … “What made the best first experience you’ve ever had with a guy? What factors came into play? How did that play out in the short term and the long term?”

  9. Jriley154

    I’ll be honest I’ve always preferred older men. In my late 20’s I was involved with a retired firefighter, mid 50’s. He was the sexiest man I’ve ever been with. It helped that he was hung, with a capital H!!

    The hottest thing ever was him fucking me till my legs gave out, pulling out and cumming all over my cock and balls, then had my use it as lube to jerk off!

  10. Steve

    I was 50 he was 56, was curious about why guys wore jock straps. So I posted an ad on Craigslist about it and he responded. We met for a drink and we rented a room and he gave me the best blowjob I’ve ever had ! No jocks were worn. But it was my first bi experience! We hooked up several times over the years when the moons were aligned.
    I then had a hot time with a 65 year old retired guy who had 8″ and FAT COCK! He worked over my nipples and smacked my ass. He then had me on my back forcing his cock down my throats for 15-20 minutes after that he pulled out and came all over my chest. With his nuts in my mouth.
    Had a 3 way with two guys who wore lingerie and were few years older then me. Hot time there.

  11. Bigolly

    Tender, extremely passionate, aggressive, patient all wrapped up in that hot moment, but most of all physically being with an older man makes me feel like I am the only sexy existence in his entire world. It’s a very connecting feeling I live for:)

  12. BriBry

    I’m in a 17 1/2 year relationship with someone 13 years my senior. The only thing I’m sorry about is that I didn’t meet him sooner. Our relationship is nothing less than amazing.

  13. Travelingtroop

    It’s not the best experience however I had an interesting experience with an older guy when I was in my early 20s. He was in his 60s. The short version is that all he wanted to do is get naked and stick his penis in between my legs and grind until he jizzed. He did just that. I decided that in the future I will turn down invites of that nature because it was kinda weird. The plus side was he gave me $200 up front because he said that he knew I would have never done that if there wasn’t an incentive. lol

  14. Jim

    I dont think younger guys on this site are looking for older. Numerous profiles indicates “No Fat Old Guys”, “No Fathers or Grandpas I already Have One”. So I am not convinced younger like older.

    • soft & fluffy

      Jim , the problem is that most guys on this site are very poor at saying what they’re actually looking for .
      As an example (and yes, I have seen the profiles saying ‘no grandpas wanted’ ) I have a dear friend who is the ex of another good friend who stays in touch with me monthly since they broke up . I met this guy when he was about 22 , his friend (my friend also) was almost 50 back then. he’s now about 33 and he really has the hots for me even though there’s a near 29 year age difference. He really likes the older guys and he’s a real catch too .
      He signed onto a4a about 5 months ago and his profile has no mention at all about liking older guys .
      And I’ll be real here , I like a bit of slightly younger stuff too but from his own life experiences before he even joined a4a he tells me that the guys who like ‘older’ are very common and everywhere . Just wish could locate one good one !

  15. Leo

    I had probably the best sex of my life with an older man nearly two years ago. We had played before, but it was never so intense as on this occasion. I make a lousy bottom, but he got me opened up and f*cked me so hard I was seeing stars and having split-second blackouts. This daddy got me in all kinds of positions I didn’t know I was capable of, and even though I had worked in porn, there were several new points. His thick hard cock, his nice foreskin, and his dominance were intoxicating. It was wonderful.
    Sure, I got gonorrhea from the experience and it ruined the best relationship I ever had (at that time), but I still count it as the best sex of my life.

  16. George

    once in a blue moon i would escort an have sex with wrinkle old dude for money an do viagra it was disgusting gross last less then one hour i couldnt wait for it to be over..(vomit).

  17. Triangleguy

    I always find the ageism in our community baffling largely because you can say you prefer x or y or z and there’s about a zero chance you’ll end up x or y or z. But when it comes to age, face up “boys,” one thing you will do is age and one thing you will be is old. As well, if we are so bent on being treated equally in society and greater community, shouldn’t we be treating others equally?

  18. azaleanpop

    I’m still waiting for some older guy to blow my mind, sexually.. I met an older guy that sucked on my nipples like no other, but other than that……..

  19. Zachary

    Most of my encounters have been with older men, men at most 20-25 years older than me. My first time with a guy was 5 years ago, two days after I turned 30. He was 49. It was a blow job, but he didn’t pressure me into it at all. He was so nice to me. I hung out with him for two hours and swam in his pool. He told me we didn’t have to do anything if I didn’t want to. He was so nice, and his niceness suddenly turned me on. So I let him do it. We hooked up a few times over a couple of years, I topped him once and bottomed for him a couple of times, but it was uncomfortable. I kind of developed feelings for him, still have some feelings for him. But I have had many encounters over the last five years. I actually got to be the older guy for once last year, when I turned 34 and he was 23. I just prefer men older than me. 10, 15, 20 years older.

  20. Eric

    I been having sex with an older guy for about three yrs now (fuck buds) I’m 36 he’s in his mid 60’s. best sexual relationship I have ever had.

  21. Kyle

    When I was 45 I met a guy who was 63. He worked with a personal trainer and his body put mine to shame. He was kind, strong, and an incredible kisser. I had a lot of fun for a while but he moved to California. I miss going to his place at lunch.

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