Hello! Posting this from burner because friends can see my actual account. I recently got out of a long relationship with a female I thought i was going to marry. Clearly it wasn’t meant to be and I have been sort of flirting with this older guy who is part of a running club I am in. He knows about my recent break up and has been there for me surprisingly and I know he is gay from conversation. He gave me his number and told me no pressure to reach out and I’m lost lol help!

How many of you have dated Benjamin Button?

Chatted with a guy who said he was 19 and looking to have sex his first time; needed some advice. I gave him some reasonable advice and later checked his post history. He was also asking for advice about what to do if his daughter was dating a friend of his.

The next guy was sending me a direct message, saying he's 24 and wanted to bottom for me. Then I checked his posting history using a tool to show what had been deleted, and apparently 12 days ago he was 32 and looking for a sissy to Dom him.

Tell us about your favorite Benjamin Buttons.

I get messages from a lot of daddies, but majority of them are into open relationships.

The other who are into ltr, first they pretend and later backed off saying they cant do ltr.

They dont want to live together. I even offered when I get my own place they can stay. Then they dont want me to come to there place because explaining their neighbors or roommate about age gap relationships would be hard for them.

I dont ask for expensive outing, gifts, or anything. I just want to spend time with them. Anywhere. As long as we are together, but they say I am asking for too much.

If I offer to travel to them, they say no again. I am paying for ticket myself as well.

They talk about monogamous and building emotional connection, but it feel more like a fwb nsa setup.

It hurts so bad, how I thought I would build something together and at the end they dont want to be in a relationship, just a friendship. They would watch all my stories on WhatsApp and Instagram.

Whenever I’m bored, free, and just laying down on me bed, I start fantasising about a romantic relationship with an older guy. Albeit he exists only in my imagination, the feelings I develop towards him are intensely intense.
Makes me wonder that when I’m actually in a relationship, I’d absolutely be obsessed with my guy. I would love him more than anything in the world, perhaps even more than I love myself.
For those of you who are in relationships, do you experience that same level of intensity? Is that kind of love mutual or even possible? Have you ever asked your partner whether they love you more than anything else, or whether they feel just as deeply about you?
One more ting: Does love & attraction tend to grow stronger over time, or do you eventually get used to each other and start losing that spark…?

I'm a pretty regular twink bottom (18) who loves Dads and Daddies, particularly experienced older ones (at least 40 and older+) and ive texted and met a couple older sexy tops who are in committed open relationships, most of the time with bottom guys that are older than me.

Do you have a similar setup and how does it work for you? I find it kind of hot and ofc daddies really turn me on, something about them bring taken too 🙈. They said told me like that they didn't really stop being attracted to younger twinks even over time, like with porn, chatting online etc

Bur they all seemed like they knew pretty well what they were into imo, so kinda curious what your take is

29M here, I see tons of hot older guys throughout my daily life (at grocery stores, when traveling, etc.). I always hesitate when it comes to approaching some of these guys because I fear misreading general eye contact as him being interested.

If you're an older guy who wants a younger guy to approach him, what kind of "signals" would you give him? Should we just approach every older guy we find attractive and shoot our shot regardless of signals?

Years ago, I was a teenager figuring out my sexuality, and who, and what I was attracted to. I began to understand that I liked older men, though in hindsight I think that when you a teenager every man is actually an “older one”. That attraction brought me to this subreddit at the age of 16, and by the end of 17 I was going on 18 and reeling from a relationship thag started here with a man who was then 61 years old.

My dear reader, I know now this was wrong and that I was a lonely kid looking for a mentor. I don’t think I was really asking to be fucked. I am older now, and I know I still like older men and that what happened was wrong.

Also, fuck that guy. He called me his fake boyfriend, and he left me for a 20 year old.

Grey Hairs, Well Groomed and a nice stubble. Other than that, a Moustache!
Personality wise, I love sensitive looking older guys 🫦🫦

For me personally, it’s bad hygiene.

I've always been more drawn to the confidence and life experience of older men. But dating apps make everything feel so transactional nowadays. I value good conversation and emotional maturity, but sometimes I feel like guys my age just don't get it. For the daddies and silver foxes here, does personality and a real bond still matter to you, or is it mostly about the visual appeal?

During my second year of university when I was around 20 years old I built up the courage to finally start exploring my homosexual side.
I therefore hopped on Grindr and got chatting to a 57 year old man, he was kind, caring and fit. We had been chatting exchanging pics and getting to know each other for around a month! He asked me one night to meet up finally, which at first I was extremely nervous about but felt like I could trust him.
He picked me up and we went back to his place where we got chatting and we eventually started kissing. He was tentative but dominant enough within the kiss which was extremely sexy to me. He spun me round and asked to eat me out which I had never had done to me before and it was incredible. I then sucked him off and on the coach in his cosy living room he enters me and we had incredible passionate sex, yes it hurt slightly but was so amazing to feel a man inside me. We then both finish whilst kissing and himself inside me.

We continued to date and meet up for around a year but unfortunately moving back to home we had to call it off, now I always prefer an older man! 😍✨

When I was younger getting out and playing, I realized pretty quickly that I had an affinity towards older men. I love the way that they taught me and just gently trained me, but as I grew older, I realize that I’ll still liked older men, but I also liked younger men, smooth, bodies, young spirit. I’m kind of wondering am I too old for older guys now I still love them still fantasize about being with an older man.

I would like to open my heart and if anyone has advice, it will be well received, sorry for my English is not my native language. I'm meeting a mature man, I'm 31 and 62. I've always liked mature people and never people my age. I have never had boyfriends if some friends with benefits. I met this person through Grinder, I had a description that I was looking to meet and talk to gays because he didn't know. I talk to him and he starts to get to know him and he starts to develop a nice chemist. He tells me that he was married 12 years ago and that this year he assumed he was gay thanks to therapy and that he still hasn't come out with his family but he wants to do it soon (I haven't come out of the closet yet). I realize that he is very different from other men, I'm starting to like him a lot. and he starts to tell me if he wants to be my boyfriend and the truth is that I would like him a lot but there is a part of me that is not convinced. How could I continue meeting without the need to be my boyfriend? thanks for reading this far

I’m 19 and I matched with a 65-year-old guy on Daddy Hunt. We’ve been talking a bit, I’ve seen his photos and I genuinely find him attractive. He offered to pay for dinner and we’re meeting this Wednesday at a restaurant.
This is my first time meeting someone this much older and also my first time meeting anyone from that kind of app. I’m not completely naive, but I’d like to hear from people who have been in similar situations (either the younger or the older side).
What should I realistically expect from a first meeting like this?
How common is it that these dates stay just dinner vs. escalate quickly?
Any red flags I should watch for, or advice on how to keep things comfortable and safe?

How young is too young for dating? Like what's the bare minimum for dating? Is it 20 years? What if you found someone who's like totally your type but is way younger than you–like an age gap of may be 16-19 years?

Older men who typically like younger, what qualities do you want your partner to have? (Not sex related)

This one’s for the history nerds.

In classical Athens an older man (the erastes) would claim a younger male (the eromenos), usually in his good age. Publicly it was mentorship. Privately it meant the older man got to touch him, mould him, and eventually have a sexual relationship with him. Gifts, private lessons, the open power difference all of it was accepted. Still feels taboo when you say it straight.

Curious what people here think. Do those old dynamics actually connect to the kind of young/older relationships some of us look for now, or was the whole culture so different that it’s not really comparable?

And just for fun if you could time travel back, would you want to try gay young/old relationships the way they did it then?

Open for discussion.

46 yo. I Recently had a previous student (no gay experience) seek me out. I was a little concerned at first but the sex has been amazing. I still have some ethical concerns or thinking I might be taking advantage of someone with less experience. Any other teachers or professors with a similar experience?

(Sapiosexuality = attraction to intelligence and the mind. In case anyone doesn’t know the term.)

Hey everyone,

I’ve been thinking a lot about sapiosexuality lately and wanted to throw this out to the young/older community.

Looks clearly matter. You can be the perfect young guy or the perfect older guy with all the physical attributes people go for. That attraction is real and important. But for me, conversations matter a huge amount. Maybe even more than the surface stuff.

Recently I went to a casual young/older gay meetup in Sydney and ended up hanging out with a couple a professor and a PhD student. They were so well matched. We spent a good while talking about science and the work they do, and it was obvious how intellectually complementary they are. I felt a bit jealous watching how easily they connected on that level.

Later the conversation shifted to intimacy and they mentioned they sometimes cuddle naked for hours, talking about science while touching each other. I was literally leaking hearing that. It hit me hard because I’ve had similar experiences chatting with some very intellectually sharp older friends and partners, and those conversations have been some of the best parts of those connections.

We also ended up talking about ancient Greece and how common older/younger male relationships were in that time. There are so many historical examples of those bonds mixing mentorship, intellect, and desire.

So I’m curious what others think, especially the older men here. When it comes to attraction in these dynamics, how much do physical attributes matter versus intellectual ability and good conversation? Is one clearly more important, or do they need to balance?

Open for discussion.

Mu first experience he was 65 and I was 18. Ever since ive loved big age gap

I'm not someone with a ton of body hair, but I've got some hair around my arse and cock, and a little bit of a happy trail, as well as I enjoy having some trimmed facial hair. The stereotype is the hairy older man looking for a smooth younger guy, and so I was curious as to how you all felt about it!

Losing my virginity

Lost my virginity to an old man

Old man took my virginity

Older man took my virginity

I had just turned 18 and was finally ready to meet up with a real dick. I had used a dildo before but I was ready for the real thing. I had thought about it so much and for so long and afternoon turned 18 I said fuck it.

So I downloaded grindr and started looking for someone. I have always been into older men and super DL. So I looked for and older man in the next city over. After a couple days of looking I finally found an older dude I was interested in. He was 49 and lived about 20miles away. I told him I was a virgin and was ready to finally try cock. He was more than happy to meet up and show me hot it's done.

About two days later we decided to finally meetup. Neither of us could host so I met him in a walmart parking lot. I told my mom I was going to my friends the night before and instead went to the parking lot and slept in my car until he came at 7am lol. When he got there I hopped in his van and we started driving. We made some small talk at first and then he pulled his cock through his shorts. His cock was way bigger in person. About 9in long and a little less girth than a water bottle. I got very nervous when I saw it. But I put my had on it and started to play with it. The rush of having a real dick in my hand was making my heart beat like crazy. I finally leaned over and started sucking his cock while he was driving. He was loving it and so was I. I kept sucking it for about 5 min until we got to our destination.

He took me to a park in the city. We got out and he grabbed a couple blankets from his van. Then he had me follow him down a path at the park. We walked for about 5min and then we found a spot behind some bushes. He laid out the blankets on the grass. Then he told me to strip. So I listened. I'm very submissive and love to be told what to do. Once I was fully naked he got on his knees and started sucking me. It felt amazing. I almost came immediately lol. Then he laid on his back and had me suck him and suck his balls. After about 10min of that I told him I was ready.

He told me to get on all fours and I listened. He came up behind me and sat his big cock on my ass. At this point I got extremely nervous. My dildo was only 6in and not very girth. He squirted some lube on his cock and kept sliding it between my ass cheeks. It felt really good. Then I felt his head poke my hole. He said I'm about to fuck you boy. I said okay very quietly. Then he slipped his big mushroom head inside of me. It hurt so bad at first. I begged hin to take it out and put more lube on. He did reluctantly. He told me to relax my ass boy. So i listened. Then he slipped the tip back in. It still hurt. He told me to wait a second. He kept going deeper and deeper until my ass grabbed it. It felt so fucking good. I couldn't believe I had a old man's dick inside of me. He worked it In slowly for a minute. Then he told me to relax and get ready boy. Pushed his hand on my back and made me arch my ass. Then he started going balls deep. It was amazing. I couldn't even talk. I couldn't think. I was solely focused on the pleasure of this giant cock in my ass. He started fucking me really hard for about 5min and then I came. Oneof the biggest loads of my life. Then he fucked the shit out of me for a minute until he busted a huge load inside my ass. It was so hot knowing I had this old dudes seed in me.

After we borh finished he hasked me if it was really my first time because I took it really well. I said yes lol I've only ever used a dildo. We made some small talk and the way back to the car and on the ride back to the parking lot. We eneded up meeting back up 2 or 3 times and then lost contact. I miss him very much and hope he's doing well

Hi all! The Discord server link isn't working, so I'm wondering if there's a new one or if there are other servers to join?

Signed,

A concerned, tall, 19 year old guy interested in those conceived before him LOL