Have You Ever: Slept With Someone Twice Your Age?

Yes, we realize this post has the potential to spawn a ton of ageist comments, but we think it’s important to break the stereotype that older men are always chasing after younger men. Although society may tell you otherwise, eighteen year-old twinks are actively pursuing hot mature men on a daily basis. Okay, so we may not have evidence of this, but we swear it’s one-hundred percent true!

As these boys swoop down to prey on an experienced gentleman, they’re let down by lines like, “Sorry, but you’re half my age” or “It creeps me out that I have a son who’s older than you”. It’s reverse age discrimination, we tell ya! These guys are breaking hearts left and right, turning down young boners like nobody’s business.

So without further ado, we’ve got to ask–have you ever pursued or slept with someone twice your age? On the flip side, have you ever rejected a potential partner because he was too young? Let’s get this conversation rolling! Leave a comment with your thoughts, secondhand stories or personal experiences.

– Dewitt

Photo credit: Jake Cruise

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107 thoughts on “Have You Ever: Slept With Someone Twice Your Age?

  1. i have, before.
    although, the older i get, the less likely i’ll be able to find more compatible partners, of the “twice-aged” status.

    i’m still not automatically wary of the idea of having relations with gentlemen up to 53, 54.

    as always, it’s really a matter of how well a person has taken care of himself, through the decades.

  2. Not at my current age, (24) but I used to do it when I was younger..=P // I have sex with people my current age, but also with little bit older, to even around 40. I lost my virginity at very young age, at 14 y.o. and from that ’til I turned 18, it was weird to have sex with someone of my age, most guys were around 30 (couple years younger, couple years older). I love to be with people around my age, but still right now, the best sex I have are with 30-40 years old. They just know what they doing when they’re dong it.

  3. I’m 24 as well, and have always had a thing for older guys. The idea that they have twice the sexual knowledge as I do, have had twice the orgasms, always excites me. I have been turned down by a few older dudes, solely on my age. And it isn’t fair. Just because I’m younger doesn’t mean I don’t know how to use my blessings, just like you age doesn’t automatically mean you have saggy balls!

    age ain’t nothing but a number

  4. my partner is younger than me, much much much (10 years per much)– he pursued me, I honestly thought ”nothing would come of it”, but when you stay in ”the now”, you don’t let sterotypical things run your life. Here we are 7 years later and we over come lots of odds, strange looks, ”are you or your son paying?”..etc. I’m told I don’t look or act my age, still don’t know what that means..I’m me, he’s him, together we’re fine…there’s way more to fuck up a relationship than any single aspect.

  5. Well Im kinda the reverse side of the coin as the previous commentors – Im 51 and lately seem to be a chicken magnet – been hit on and have slept with more 18-20 year olds this last year than when I was that age….. When my sexual life started B.C. (before computers ;o) ), there was a lot less emphasis on how old a guy you were hot for was.. My second boyfriend was 18 years older than me – I liked the days when intergenerational socializing was more common….
    The best sex I had as an 18 year old was with this 39 year old guy – man, he taught me lots!!!! All my subsequent partners were benificiaries of the things I learned from Carl…, and now Im happy to pass on those secrets to a new generation – my sacred duty as a card carrying homo.

  6. i’m 26 and have a boyfriend who is 47. It’s totally perfect!!! we met 2 years ago!
    the best part is sex, because the experience of a man who lived 20 years more than me appears in bed. But out of bed it’s great too, i think the younger must be a little bit mature or inverse.. but the chemical could be really awesome!

  7. Absolutely! They know everything about the male body…also, they have no gag reflex…I have never came 6 times in one night til I met up with a 39 year old (I was 18 at the time). We still meet up regularly and I’m going up to his lodge next weekend to have a weekend of hot sex.

  8. I can honestly say I’ve never turned down sex with someone half my age! I’m I’m attracted and vice-versa, it doesn’t matter the age, just the attraction.

  9. I’ve always had it for a more mature stud in the sack. As I’ve gotten older, I’ve gotten better in bed, and likewise, the older guys usually mature nicely in their technique and passion.

    When I was young, sex was over much too fast, for both myself and the young guy I was with. Now, it can last a mind blowing long time, and that’s what I appreciate most about a more “seasoned” guy.

  10. on the flip side: since 26 (or maybe 25), i’ve turned away a few younger adults, once it became evident they didn’t possess enough maturity or/and “direction,” for my taste.

    i predict that i will continue rejecting some youthful suitors, well into the future — likely, those individuals in the 18 – 24 group.

    i can tell you this much: i don’t have a very high opinion of the under-aged drinker. especially since i don’t drink at all (but have already witnessed enough drunken foolishness to last me a lifetime), i’m not impressed by alcohol, one bit.
    so, the Under-Aged Drinker has automatically decreased his chances with me by around 92%

  11. I’m 22, and I’m dating the sexiest 44 year old! I too have a thing for older guys, seems like salt and pepper hair turns me on.

    Unfortunately, it seems like we’re on different pages a lot of the time. He’s already done most of the things I hope to do in the future. I like to go out a couple of nights a week, he doesn’t, I want kids, he says he’s “too old” for that… hopefully it works out!

  12. Yes, I’ve hooked up with guys twice my age before, and once with a guy who was atleast 3 times my age, lmao! Older can be hot as long as you haven’t let your body go to hell and still have all your teeth. In fact I actually prefer older. Gerard Butler, Hugh Jackman, Anderson Cooper type of guys really get me going…Woof!

  13. I have. Shrug. Sometimes I think they’re 30 or something, go home, let them rip the fuck out of me, hook up a few more times, and end up shocked to discover he’s in his 50s.

    Oh well. Daddy can tear the fuck out of me.

    And yes, it’s true. There’s a lot of young guys in their early 20s late teens who chase much older men. I never understood why.

  14. this is gross, just a bunch of young guys with daddy complexes. fuckin old guys wont substitute for your daddy not loving u, sorry, or maybe its for money, gross either way.

    i hate when old guys come on to me, just because a bunch of teenaged or early twenty year old sluts fuck around with you doesnt mean youre hot, or younger looking. disgust.

  15. My first boyfriend was twice my age (18 and 36). We stayed together for almost a year but he was heading towards settling down and I wasn’t exactly going to be satisfied for my whole life only have slept with two people, including him.

  16. This is a difficult subject for me “twice my age” or “Half my age” Frankly I don’t feel my recorded age but the comments so far refer to 40/50 years old. I’ll be 70 next June and still hope to fill a space vacated by a special man less than half my age but a relationship of 25 years, ended when I moved countries.
    The fears of this great age begin with disbelief, how can this young and beautiful person fancy this old body, he must be here for the money. Well that’s a very big hill to get over in bed and badly affects performance. The fears are easily transferred to the willing beautiful man in bed and a wall of difficulty arises. It takes time to build confidence and if confidence comes along so does the physical attributes so necessay for a good night in bed. The other thing I would say is as age dominates one side of the liaison the chances of success are improved by the accelerated need for “give and Take” and probably more give on the younger side

  17. Young Guys, Twinks
    .I have some news for you.

    You will age. You will become the older gay man in time.
    So give them a break, if your attracted go for it

  18. I am past 50 and get hit more often by guys under 30 than guys my own age. The other day an 18 yo was hot for me. I turn them down all the time. Prefer guys past 40.

  19. It’s actually rather ironic that this post came up today… I’m 26, and I’ve never been a blatant “age limit” guy, or a “types” guy. I know what I like, when I see it… regardless of race, age, anything. But the other day.

    However, the other day, an 18 year old started chatting with me, and we went back and forth a few times in emails, then text messages. We met up the other night for coffee, and I felt VERY awkward! I felt so much older, he was taking about his college midterms! He called me later that night, he came over, wanted to fool around, and I wouldn’t let it go past making out. I just felt like he was far too young for me! (albeit, he was REALLY hot)

  20. Never…I have never been attracted to men much older than myself. However, I found it uncomfortable yet hot that my prior BF was nine years younger than me. What really shocked me is my current BF is 18 years younger than me, and HE pursued ME. I must be getting in touch with my inner daddy…and loving every minute of it!

  21. I was always the young guy with the older guy…. one of my great loves was 38 when I was 24…..

    my last relationship that lasted about a year (we r still in eachother’s lives, on and off), was 20 years older than me (I am going to be 37 in a couple weeks)..

    the older I get the more complicated relationships with older men become, because they r even more settled than I am… but I like the experience they have..

    it is funny, I have had lots of guys in their 20s approach me online… and I always think they r too young, that there is very little in common… they r in college, I teach college, they r getting their first apartment, I own my first home, etc… I think I am becoming the object of desire of my youth hehehe…

    I think I am going to reconsider the 20 something crowd, give them a try =-)

  22. there are older hot men, and then there is jake cruise…please dont confuse the two…his vids are like creepy-palooza.

  23. I was chatting with this guy off of manhunt before. Really nice, cute, but older than I’d ever been with before. The fact that he was only 3 years younger than my dad was a little off putting. (I’m 20, this guy was 48) but I was willing to give it a try. Until he told me that his daughter was 26. That’s a deal breaker. I could never date someone if I was younger than their kids.

  24. Yes i did many times if still looking hot why not:-)
    Now i’m having hard time in sleeping with a young dude:-(

  25. there are older hot men, and then there is jake cruise…please dont confuse the two…his vids are like creepy-palooza.

    Thanks Rob for saying exactly what I was thinking. I freakin love older guys..but Jake makes me want Puke!

  26. As a 47 year old I have found lately more younger guys seem to be chasing me although to be honest I do not chase the younger ones.

    But everytime I see a Jake Cruise posting I absolutely CRINGE I really don’t think he would get majority of these guys unless he paid them.

    I am sorry but he reminds me of some kind of gross old troll.

    I think that is why he created his Spin Off web sites cause they make more money then the ones with him.

  27. Yes I have, many times, haha. Even right now, my boyfriend is 53 and I’m 25. I don’t go exclusively for older guys, I just like mature and masculine, which is a rarity in my age group.

    @TimBo: Jake Cruise is sexy as hell and I would gladly hook up with him, paid or not, haha.

  28. I’m nineteen and I’m a self proclaimed Old man molester. I like men in their thirties and forties. Guys who like like they could be my dad. Huge turn on being with a man a bit bigger and older than i am.

  29. I had my first sexual experience with a man who I thought was 34…but was actually 45. i definitely could not tell though…he had a muscular, firm, and tight body, had the cutest face, and was an AMAZING first time!

  30. Yeah i did just recently, am 20 and he was 40. wasn’t so much that he was better in bed, rather than the the scenario being comfortable as there was no young guy drama. the older guys look at the best parts of you and get off on it. the younger guys search for the worst in you so they have a reason not too. older guys are just more respectful and caring. if younger guys had the maturity of older men i would be in heaven…

  31. I’m in a Dad/boy relationship for two years and counting, and I can obviously answer a big, loud “YES” to the question posed in this posting. There’s a 26-year difference between us–I’m 23 and he’s 49–and it’s really all about an eternal love and attraction that’s between us. That being said, there ARE things that we “miss out” on because of the age difference, and that’s something we’ve agreed on early on in the relationship. We both understand that there’s only so much that we can give each other (for us…I’m not saying this is true across the board for cross-generational relationships), which is why we are open to dating people closer to our respective ages. As he always tells me, he wants someone who can “remember the Reagan era”!

    As for merely sleeping with, I think that’s really easy. I’ve always been attracted to those who were older–teachers, professors, etc. One of the first people I fooled around with was over 50 and I was 19. I rather enjoyed it. I get a kick out of being liked by older guys, and I’m sure they get a kick out of me liking them as well!

  32. No, I’ve never slept with anyone who is 108.

    Yes, I’ve slept with a number of guys who are 27 (or even younger).

  33. I feel like Dan above. I am 62, the other guy is 23 and frankly, I am not quite sure how to handle it. He is pretty hot, and I am not in the best of shape. He tells me that he loves me, and I keep wondering what he wants. I don’t know how to just let it happen. Or if I should.

  34. Had a lover who was 11 yrs older than me.We were together 24 yrs til he died of a heart attack.Now,beginning again in my life,I find the dynamics are uncredibly diff.I am older,true,but not some ‘gross old troll’.Shame on the haters.At 51,I do OK,with guys of a variety of ages.Some are fun,some not.It isnt as much about age as it is being yourself.I do OK,just no lover at my age.THAT part sucks.But I am happy to say I knew love once.

  35. scottdicks, that was a great line.

    most spring/fall relationships are boys acting out daddy/son dynamics because they were abused at a young age by an older man; ie they’re not really gay but the experience scrambled their sexual radar.

    but getting older and more beaten down by life (called “experience”) does make you a more gentle and understanding person. less judgemental as you have been up and been down (most young people have never failed because they never tried anything). so quite aside from abuse dynamics, old men have a lot to offer 🙂

  36. Wow, Ray. I wish you the best. Your story touched my heart.

    I’ve never been with someone twice my age.. Close to it, I guess. I’m always getting the younger ones. I’d prefer someone in their thirties/early 40’s but am open to anyone as long as they are mature and over the drama phase. My main thing is that they know how to fall in love and to love me in spite of my faults. Anyone should be capable of that, regardless of age.

  37. No I haven’t. But I tend to date/see older guys…usually in their 30s. I don’t particularly click with anyone in my age bracket.

  38. Age is just a number. I’m with guys older or younger as long as they take care of themselves. When I was 18, I had a steady relationship with a guy in the late 50. He was in great shape, hung thick and can fuck me every night.

  39. Oh yeah, I’ve always been a fan of the silverfoxes. When I was 23, I had 2 fuckbuddies that were both 46, and both of them were some of the hottest guys I’ve ever laid hands on. Plus they were incredible in the sack!

    Its a shame a lot of younger guys immediately dismiss guys over 30 on their MH profiles… Actually its a good thing for me because it means less competition for me!

  40. I’m 62 and my partner is 43. We’ve been together for 6 years, although I’ve been searching for him forever. I didn’t know what “love at first sight” was til I met him.

  41. I am 22 y/o and have always been more attracted to older guys, not because i am looking for a daddy to replace the “love” my daddy never gave me. More for the fact that I have always been more mature and “grown-up” for my age, and most older men do not come with drama and have their lives figured out. I have too much going on with my life to worry about someone my age who is freaking out because their ex is talking to some new guy…but that is why I mainly am attracted to older guys.

    When i was about 19 I hooked up with a guy who was about 54. I just hate it when older guys lie about their age. One guy I was with, swore up and down he was 23, we dated for a few months, and then became best friends…and that was when i was 18. He is still 23 tho…plus 7. I always tell him he needs to just be honest, if someone doesnt like him cuz he is 30 and can pass for 23…then he is just too good for them.

  42. It was easier to have sex with men twice my age when I was younger, but now that I am 33, it’s not so easy. I still have a thing for older guys though, always have. Guys my age rarely do anything for me. I need the mental maturity to get along with a guy, and that doesn’t happen with guys my age.

  43. I have slept with a few guys who were twice my age and some that were a bit more than that. I like older guys 🙂

    I have had the older guy make a very non-sexy comment referring to me as being young enough to be his son but that doesn’t happen too often.

  44. Although I have been approached by a couple of older gentlemen [don’t know if they were twice my age] I’ve NEVER dated [or anything else] somebody twice my age. And the way I feel now I don’t think that I ever will. This in NO WAY means that older men can’t be handsome and sexy, check out: Jimmy Smits, Pierce Brosnan or Viggo Mortensen to name a few and all in their fifties.

    I don’t understand this Daddy fixation that some people seem to have. I love my father dearly but I find the idea of Dad and Sex extremely disturbing. When I discuss this topic I always get a picture of Hugh Hefner and those extremely young playmates going at it. The idea of a Hugh Hefner type in my bed getting ready to come just creeps me out big time.

    I’m still too young to actually date somebody half my age [that would make them jail-bait] 🙂 Yet I can’t see myself dating a 25 year old when I’m 50.

    I appreciate that other people don’t have my weird hang-ups. If both parties sincerely care for and are committed to each other then I don’t see why such a May-December relationship wouldn’t work. What is it they say? “Variety is the spice of life”

  45. i personaly like older guys, slept with some twice my age but never dated anyone more than a few years older, personaly for dating draw the line at 32ish im 23 now. But otherwise depends on the guy, love older dominant tops, so with the right guy easly go twice my age or older

  46. Well, I have to say, I never thought I would be one of those guys that dated a younger man. I always thought that they were immature, childish and just looking for someone to take care of them. I looked at men my age as stable, self sufficient and financially responsible. It was just a few weeks prior that I had a discussion with a friend about him wanting to date a 25 year old (he is 41).

    Then I met Dex. He is truly like no other man I have ever dated. I am 41, he is 18. I would never have guessed him to be that young. Again, it all boils down to maturity. I’m not saying we don’t have hurdles to jump. My work dictates my schedule in that I am up early and generally in bed by 10. He is just getting revved up and usually stays up until 3am. I just can’t do it.

    Empirically, he is ideal. We have adult discussions, we have fought and usually do it like adults. I want to be able to enhance his life and he mine. So far, that is how we are headed. Also, I can see that I truly love him. I read not too long ago something along the lines of “…one day you will meet the person that will make you understand why all the ones before never worked…”. I think I have.

  47. I’m so glad reading these stories from all of you. I’m 18 but I’ve been openly gay since I was 14, and started going on gay chatrooms around about that time, since I was the only gay guy I knew in real life… then it led to camming… then it led to pictures… then it led to MANHUNT… then when I was 17, I began to have sex with men much older than me. The oldest I “had” was 44, that was only a few months ago. It’s mainly a factor of guys around my age just not being that interested in me, and because I do consider myself mature for my years.

  48. joel, tommy, jesse others… it is great isn’t it?
    [then there are those who judge and condemn; oh well, that’s why we have the religious right]
    My partner is half my age and a couple more years. We are coming up on 5 years together. I relate to the ‘staying in the now and bucking the normal’. When he first contacted me, 1000+ miles away, I told him nothing would come of us. We talked over the internet. He pursued me a lot. I teach mind development and spiritual counsel plus some and finally meditated about it… I instantly heard to pay attention to this young man. Since I have been doing intuitive training I have learned to listen. So, I did. Everytime I went inside it got much stronger. There was/still is something very different about him. We have the most comfortable relationship that I have ever had with anyone. This is my first ever younger relationship. I always dated men a few years older than me. So, I had to completely modify some mental concepts, stop being concerned about what others think and just let it be.

    What really made it work is 2 years in we stayed a week at his parents home in NY over Christmas holidays; even made out in his bed. His love is all that matters and having his family’s acceptance made it all the sweeter.

    Saint Impatience: maturity is not automatically gained with increased years. I know some very immature old people and some very mature younger people. Maturity is connected to something much deeper inside us. Some people come into this life ‘deeper’ and some ‘not so’… and neither one is better than the other

    Anyway, wherever we find love let it in… why would we ever reject love? Anything that is healthy, good for the soul, mind and body, is worth putting our heart into.

  49. One night when I went out clubbing, a few days before I turned 17 and I was chatting to this guy and all such and ended up going home with him, I thought he was in his early 20’s, so only a few years older than me, the next day I found out he was 33 and had two children. He had no idea how old I was either (I’ve always looked a fair bit older than I am)

    Now two years on I’m in a relationship with the guy and we’re as happy as larry.

    Also. In Victoria, the age of consent in 16 so nothing illegal was involved (aside form me being in clubs :P)

  50. If I dated someone twice my age he would be about 99 years old. Most of the guys I’ve been with have been younger. These days they’re in there 30’s. When I had my MH profile I did talk to a lot of twenty somethings and even hook-up with a few of them. I usually let them decide if they really want to. I think the youngest was about 24.I would have to say I’d be open to dating younger but have yet to meet someone with the level of maturity I’d be looking for. Right now the guy I’m interested in is 34. So we’ll see what happens with him.

  51. Yep, I’ve done it. I actually don’t know his exact age, but I know he completed dental school in 1986. I’m 21.

    He was nice though.

  52. Way back when, was with a guy almost twice my age. He was a great teacher.
    Then..marriage, a child, then, 12 years later, divorce.
    After 2 years, met the love of my life, who is only 9 years my senior. I’m 45, you guys do the math.
    Enjoy developing the “talents” taught to me years ago by the guy almost twice my age..we both do!
    To Ray, a few posts before this..my best wishes to you, sincerely!!

  53. Yeah I’ve been with a few guys twice my age. I’m 20 and I the oldest I’ve been with was 45, we had pretty good relationship while it lasted. I have to problems with guys of any age older or younger than me. Love is love, isn’t that what the whole gay rights movement is about?

  54. I prefer older guys, been with my guy for 4 and a half years and 2 and a half years ago we got married. Being with him is amazing. I am 28 and he is 50

  55. dear L. in Austin, i thank you for sharing that tidbit with me.
    but i can assure you that i’m already cognizant of it.


    if anything, an emotionally-/psychologically-immature older adult is even worse: what’s their excuse, for not having developed as they should have?


    i can find many examples of those very individuals in Wall Street, and in the run-of-the-mill “high ‘leadership'” positions!)

  56. The unfortunate “reality check” is most of the guys looking for someone twice their age are looking for a sugar daddy to take care of them…I have first hand experience in that arena! But, I do have to admit that I had a lover for 14 years who was 20 years younger and when we met he was 1/2 my age exactly so…maybe not so bad after all.

  57. LOL…being the TOP Papi I have fucked men HALF my age…I hsve them 19 and up…and plan to continue to do so…Gawd Bless Gay Men…lol

  58. I met a guy four years ago when he was 18 and now he is almost 22. We have been doing the hook up thing about once a week of so. But now this last month he wants to date me exclusively. He has been sending me flowers, taking me out to dinner, introducing me to his friends etc. He is a hot triathlete and all my friends say i should date him. The problem isn’t our age difference now. Yes I’m more than twice his age. I’m 52. The problems is time. What happens when i’m 62 and he is 32 and even more important, god willing i’m 72 and he is 42. I really think that is an issue.

  59. I love older men. I lost my virginity when I was 14 to a 45 year old man. And when I was 17 I entered a long term relationship with a 42 year old. Recently I fell for a hot muscle daddy who is 57. And no I was not looking for a sugar daddy.

  60. The oldest guy I have been with was 72…and I was was 23, but he didn’t look aged. He gave the best head ever.

  61. The oldest man I’ve been with was probably in his late 50s or early 60s. Nice guy, but not for me. The oldest I’ve been with on a regular basis is about ten years my senior. I generally go for men around my own age, but if a man is mature, sincere, willing, and we’re attractive to each other, age isn’t an issue.

    As far as younger/older relationships, as long as it’s a relationship based on mututal trust, love, and support (meaning one or the other isn’t a sugar daddy), I say go for it. Love IS love.

  62. Well I tell you one thing, if I was Jake Cruise and made a living fucking younger dudes and made a living with my cock, I would be hitting the gym every day and at least be a really sexy older guy.

  63. I’m on the other side of that equation – I’m happily surprised how many twenty-somethings (and occasionally younger) want to hook up with this daddy. Not complaining at all, mind you – just surprised.

  64. There is certainly something to be said for us “older” guys. Many of us have great experiences and techniques that the younger guys can learn from. That being said, while the young boys are all hot and sexy, I’d much rather have sex with someone nearer my age…but would probably rather look at pics and videos of the younger ones. Generally speaking of course but there you have it.

  65. Lately, I’ve been getting a lot of hits from guys in their early 20s. Just played with a guy 19 years younger than me earlier this week. It helps that submissive guys often gravitate to older dominants, because older doms are often more experienced, an in BDSM play, experience makes a huge difference. So I look at myself as a bit of leather evangelist, helping keep the leather tradition alive.

  66. My partner and I are in the best shapes of our lives and find we are attracting the late 20’s and thirtysomethings.
    At first we did turn some guys down because we felt we were too mature for them but then realized the age number has very little to do with it. It is all about the connection. We met one guy on MH that was 15 years younger in years but a perfect match for us in every way. We had a sexual plus relationship for 6 months and are still good friends. We learned from him and he from us.
    Older, younger it doesn’t matter–it is about the connection.
    As we move into our fifties we are finding fewer guys our age that take care of themselves and who are still excited about life. You have to be excited about life to be exciting in bed. Passion is passion.
    If you tap into the societal definition of age and stages you will be old before your time.
    There is nothing like hot sex –period. Having hot sex is not about age but about the connection.
    Sometimes we refrain from telling someone we have been together for 20 plus years because just like telling your age, that can freak someone out.
    The intensity and passion you get from two people who are in love and like to share themselves with a third on occasion is powerful. At least that’s the feed back we get from the guys we connect with–no matter the age.

    Thanks for dealing with this topic. It is important. We all make decisions on how to live our lives. we decided to live it being healthy, sexy and passionate.

  67. Older guys are always more interesting. The youth is wasted on the young. When it comes to sex I prefer guys older than me because I like men who know what they want. It’s a matter of being a student and not a teacher in bed when it comes to my preferences.

  68. I am sexually attracted to older, fit, hairy men, and prefer them for sexual encounters. Yet when I date, it tends to be around my own age. I think PART of the reason is that I WOULD care what fam/friends and the world thought if I dated someone twice my age.

    But also I find that we just arent interested in the same things. It’s not a question of maturity. I just cant relate to someone talking about buying another property and looking forward to retirement, whn I can barely afford to rent and still dont know what I want to do with my life. That’s a hard divide.

    That all said, the best sex I’ve had is always with older men, some twice my age, and I love it. 🙂

  69. It doesn’t matter when it comes to ages, if the chemistry is off the hook.
    I’m 20, and my boyfriend is 50, and we are almost about to celebrate our one-year annie

  70. Wow, I totally empathize with senseofplay. That’s pretty much been my experience. I’ve always had sex, mostly, with men twice my age. But ultimately, I can’t see myself in a LTR with them because we just wouldn’t be at the same stage in life…I would like to have a bf that is closer to my age and grow older together, but sadly, I haven’t found that person and I gravitate (mostly sexually) to the daddy types, which usually are very nice to me and I think that they appreciate me accepting their compliments and genuinely being attracted to them, since most young guys my age can be douchebags to older men.

  71. I am 68 and have a big 9 inch cock and I hook with younger guys all the time. as young as 18 and most 25 to 45… most come back again and again.. You have heard it before.. but age is just a number.

  72. When I was 28 I was dating a man who was 38. After a few months, he dumped me, saying I was too young for him. A month later I ran into him at a party, where I was introduced to his new boyfriend, who was EIGHTEEN. So much for me being too young for him. Ironically, I ran into his profile here on ManHunt a couple months ago, and the man who was 38 when I was 28 is now 42 while I am 48 (at least that’s what my birth certificate suggests). Sorry, but no amount of Miss Clairol Hair Color can shave 16 years off someone’s actual age, no matter how much one might want it to… Oh, and when I was 18 I dated a man who was 42, so I guess my answer to the question at hand would be yes.

  73. Im 23 and I have always loved older men. Not because of what they know and what they have. It’s when I see that salt&pepper hair my dick gets hard as a rock and my asshole puckers.

  74. after 90 hot banging sexy minutes with a very sweet guy, I thought he was in school he said. I enquired – what is your degree
    you’re going after?

    Degree?? Hey man I’m only 16 here on fake ID. I was 3 times his age. He chased me down in a bathhouse until he jumped in my room after 4 rejections. Slammed the door
    and fell to his knees and said – I want what I want, and you’ve gotta let me prove it.

    I thought 19 – 21, but 16. I had only to laugh. Only problem was he had only used 4 condoms in his life and didn’t like them.
    I was #5. Sadly – he’s 22 with HIV and i would still take his agressive chasing me down anyday. Yes – they are persistent.
    All you can do is fill their lil’ faces,
    and butts to keep ’em happy.

  75. Over the years I have come 2 learn that sometimes it’s worth just taken a chance when we allow something good 2 pass us by we usually look back on it with regret , Love is a special thing and when it is true love everything else should be 2ND nature .It is often said that age is just a number ( not that I subscribe 2 that notion ) but LOVE is so much more than that it can be uplifting, spiritual,rewarding and the very foundation 4 which we build the rest of our lives on . So if U R fortunate enough 2 be truly blessed with a wonderful love that brings 4TH longevity & happiness rather there is a age difference or not is irrelevant 4 as long 2 of U have a wonderful life 2 ENJOY !!!

  76. My boyfriend is 46, and I’m 20. We’ve been together for almost two years now, happily together still.

  77. I remember when I was like 20 I hooked up with this really hot muscular Greek guy that was 50. That is the oldest. Taught me how to be a good Top. Was some good fucking.
    But whenever I see pictures in porn of hot young guys with old silver haired guys or unattractive older guys period..it honestly makes me sad. And I feel sorry for them. I’m just sayin

  78. My personal preference isn’t a man so much older than me. Then again not all men age the same. Take Johnny Depp, Hugh Jackman, & Brad Pitt for example. All are over 40, yet all put most 20 year olds to shame in the looks department. It all depends on the man and if I find him attractive. As the late Aaliyah once said, Age ain’t nothing but a number. However the older man in these pics is not my cup of tea. However he is for somebody and that’s what makes the world go round.

  79. I don’t believe age has anything to do with a relationship, at least for me. It is the maturity level and how the two people feel when they are together.

    I have been dating my man, who is 11 years older than I am, and we are loving every moment of it

  80. I’m 20 and i only find older gentlemen attractive. The youngest I’ve found myself with was 43 and the oldest being 60 (Go go 3x my age 😉 ) To me gray hair is extremely sexy, the experience factor is also a huge turn on. People my own age don’t do anything for me and i have no desire to persue one.

  81. My first experience was with a guy 3 times my age – I was 14 and he was 42. Clearly he was a pedo but I thought he was incredibly sexy and i had fantasies about him before anything happened. We only had a couple of mutual jerk off and suck sessions but the fantasy was definitely fulfilled.

  82. I’m 42, and in the last year I’ve had sex with a guy that was 62 (my old college advisor) and a guy that was 19 (who had dated two of my employees). I liked the older guy’s experience, and the younger guy’s body… Currently with a 34-year old and I got the best of both worlds.

  83. I 19 now and while I don’t mind guys my age it can be awkward. I started having sex at 13, in hindsight that was WAY too young to start fucking a 27 year old. I know that lots of guys will say that I was preyed on and I probably was but at the time I thought he was caring and I felt empowered. Now I am jaded and think that guys that are my father’s age are a bit much (my father is 42). Mind you I hate having to teach boys my age how to kiss or how to top or bottom (I’m Vers). Plus when a guy hits mid to late 20’s he is at his peak and knows what he is doing. I guess as most people say it is about maturity.

  84. Tim – I’m your age and my partner is 24. Initially I had those thoughts about what happens when (fill in the blank with a fear). That is why I found different people to counsel with to make sure my head was on straight before I jumped in. I finally was able to just accept that this is the right person for my life. All we have for our life is a progressive series of NOW moments. Why not be with someone who fulfills us?

  85. I’m 18 Dating a guy that’s older than me (41). That’s how I see it, just older. He asked to hang out, I went over his house, and fell in love. We get pushed into label’s and norms, forgetting that it’s only a label if you choose to wear it. I’m not sleeping around, I hope it last, but if it doesn’t I’ll know that I tried and he gave me a chance, and I gave him one.

  86. Yes, and somed of them have had better bodies than guys i’ve fucked my age!! One wqas a total bottom who played squash and was so fit and he was 52 at the time (i’m 21).

  87. I was always much more mentally mature than my classmates growing up…I had lots of older relatives and generally preferred talking to them than people my own age…I have always been attracted to older men, both physically and mentally…the day after I turned 25 I met a man who would become my first pover/partner…a few months later he turned 50…heck, he had a lesbian daughter one year older than I and a son one year younger…I was never interested in younger guys, even when I was younger…now that I am in my mid 40’s (46), I at least can enjoy guys closer to my own age…but I very rarely will date or go out with a guy younger…all of my partners have been at least a year older…I have only met one younger man who caught my attention completely…sadly, geography was a problem and he eventually found love with another man in his area (sad for me…I am very happy for him and his partner for finding each other)…in the past few years many younger men have tried to hook up with me…I can see why they would…when I was their age I would have found me attractive…so I understand it…but I have no interest in them…older men have always done it for me and probably always will…and it has nothing to do with Top/bottom or “Sugar Daddy” status…

  88. I loooove sleeping with older guys… VERY HOT.. I probably wouldn’t date someone any older than 15 years my senior but have definitely slept with guys older than that!! YUMM

  89. Well, sounds like I’m a dissenting voice at least on this latest page of comments.

    My first “boyfriend” was 29 and I was 17. He was Mexican and had that frustrating Latino “I’ll always look younger than I am” thing going on. Anyways, I’d barely started accepting my sexuality and a friend introduced us; he was pretty dominant and while I felt like it was what I wanted, it didn’t take long to realize it wasn’t a healthy relationship.

    I definitely envy the 18-20 year-olds on here who’re older than their years. Of nearly all of the guys that age I’ve met, even my age, when they express or extol their maturity all I’ve ever determined is that they haven’t experienced enough of life to know how little they actually know. It would have been nice back then to know what I actually thought I knew.

    Since ending the first relationship, the guys I’ve connected with have been within a few years of my age. The significantly older guys I’ve hooked up with always seem to have a desperate quality that just makes me uncomfortable, an unnatural kind of hunger. The only guys significantly younger than me that I’ve been stricken with just happen to be attractive enough that I’m star struck. Even then though they’re only 3-4 years younger at most.

  90. to paraphrase madelaine khan from blazing saddles, “is it twue what they say bout men of youw age?…(zippp)…oh! it’s twue! it’s twue!”

    this thread could also be called, “have you ever slept with a man 1/2 your age?”
    and yes, twinks chase relentlessly.

    as a 55y.o. who recently rediscovered the pleasures of getting fucked, what choice do i have? my generation was decimated by aids and of those of us who survived, most have physically gone to hell while the rest are “looking for younger”.

  91. No, but I’ve slept with several half my age. At 44, I have a hot little 22-year-old ****buddy who comes over and slips it to me about once a week.

  92. Yes…I love older guys. Had one year when I was 19 that I slept with 3 48-year old guys…and they are still some of the best sexual experiences I’ve ever had.

    And I’m one of the ones who gets turned down for being too young! Had a guy last week tell me no because I was younger than one of his kids…I mean…yeah that’s true. But isn’t that part of what makes sleeping with guys a generation older/younger than you so hot? Because it’s so taboo? But seriously. What older guy really doesn’t want to tap an 18-24 year old hottie? We have awesome stamina.

  93. I am 26 and my partner is nearly 60. I never been with a guy around my age and dont feel attracted to them at all. If theyr arent older they arent for me as simple as that!!!

  94. I’m currently 23, and usually go for 30+. Last boyfriend was 48, and while most older men I’ve had sex with are better there’s been some that it hasn’t been. For example, my48 yr old ex-bf hadn’t come out of the closet or slept with any guys (or anyone) until about 6 years ago, so he didn’t have much bedroom experience when we met 4 years ago. To say the least, his hole was tight as hell though! :3 Another guy, he definitely knew what he was doing, but when it came to topping him, I felt like I might need to stick a toy in there to keep from falling in!

  95. In my early twenties I had several encounters with a handsome man in his early fifties.  I appreciated his wisdom and experience… and that he was comfortable with himself.  That’s when I learned age is just a number.  Now that I’ve reached his age I am very lucky to have a twink lover who has learned the same.  It’s about compatibility and love, not age.

  96. Yep i was 21, he was 48, unknown to me. His manhunt profile said 38 but according to facebook hes 48

  97. I actually prefer men who are much older than I am, because they don’t have the same drama and issues as young guys do. Of course, older guys are not as hard, not as big, and may not have quite the same stamina. But hard and big are not always desirable – especially when they come with drama.

  98. when I was 22, I had a one night stand with a guy who was 3 times my age. He was really HOT. Very muscular

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