This is my first post on Reddit, and I’m new here. I’m 47 years old, and 26 years ago, I had my first experience with a man. I remember it like it was yesterday. I’m bisexual, but I usually prefer very feminine guys. I’m a top, masculine, and I’ve always been on that side of things. But my first experience was the opposite, and maybe that’s why it’s stuck in my memory so clearly.

At the time, I was living in the southeast of France. I’d moved there to study History, but honestly, it was more about getting out of my family’s nest and tasting freedom for the first time. The place was like something out of a postcard—old streets full of history, little coffee shops where beautiful women sat drinking, smoking, and laughing, and, of course, tanned, handsome men everywhere. It was incredible.

The only problem was that I had a roommate (an ugly one for the ones who wonder), so I couldn’t just invite whoever I wanted over without him knowing. Back then, I didn’t have any real experience with men. I’d played around online a bit, but I wasn’t ready to take things into real life. Still, the thought of it was always there, lingering in my mind—when I touched myself at night or when a guy smiled at me on the street. I was young, confident, and maybe a little naive, but I wasn’t shy about giving a smile back.

For months, life just carried on. I even got a girlfriend—a gorgeous Latina with the kind of curves that made heads turn. She was really horny, but that’s a story for another time (and probably a different subreddit). Then something changed that unlocked everything.

My roommate got a job in a small town nearby and started staying there during the week, only coming back on weekends. Around the same time, my girlfriend had to go back to her country for a few weeks. Suddenly, I had the flat all to myself during the week.

I’d been chatting online with this married guy for a while. He was in his 40s, really kind, funny, and never pushy—unlike most of the guys I talked to back then. We got along really well, and the fact that he was married made me feel like my secret was safe with him.

On my first morning alone in the flat, I logged into MSN (yeah, back in those days!), and there he was. We’d played around online before, and I thought he was so sexy. I couldn’t stop watching his hands as he stroked himself. And the fact that he kept his wedding ring on? That turned me on so much—it was like the forbidden cherry on top.

I was so hard and so horny. Out of the blue, I told him I was alone that day and that I wanted to meet. It’s funny because I think he was completely caught off guard—he didn’t expect that at all. Actually, I’m pretty sure he hadn’t met many men in real life before, either. I saw him hesitate for a few seconds, and honestly, that hesitation turned me on even more. It gave me this strange sense of power, like I was in control for once. It also gave me a little boost of confidence, which I really needed at that moment.

Of course, I was nervous—anxious and excited all at once. My heart was pounding so hard I could feel it in my chest. And as I’m writing this now, I can feel my heart racing just thinking about it. Call it destiny, but his wife wasn’t home that day either. She had taken the kids to visit her parents for a few days. It was like the stars had aligned.

He hesitated a little longer and then asked where I wanted to meet him. Maybe he thought I’d suggest a coffee shop or some neutral public place. But without even thinking, I said he could come straight to my place. No hesitation, just straight-up confidence that even surprised me.

I remember his reaction so clearly—he smiled. It wasn’t a big smile, just this subtle, knowing look. And that was it. He said, “Okay,” and told me he was on his way. Just like that.

Time seemed to pass so slowly after that. I looked around and realized the flat was a complete mess. I panicked and started cleaning as fast as I could. Then I jumped in the shower and shaved my cock—I remember telling myself to take it slow so I wouldn’t cut myself. He’d mentioned in one of our chats that he liked it clean and shaved, so I made sure to do it right.

About an hour later, the doorbell rang. My heart was racing. I opened the door, and there he was—he looked even sexier in person. I think I blushed because I remember him smiling again. I welcomed him in. He was wearing a crisp white shirt, blue jeans, leather shoes, and aviator sunglasses. Meanwhile, I was in shorts with no underwear (I’ve never liked wearing underwear), and the feeling of my shaved cock against the fabric was… let’s just say, so yummy. I also had on a simple T-shirt.

I tried to play it cool, acting like I was completely comfortable with the situation, even though I wasn’t. Maybe he was pretending to be calm too, but I couldn’t tell. We sat down on the sofa, and I asked if he wanted something to drink. I desperately needed one—definitely not coffee; that would’ve made things worse. I poured us both a glass of bad whisky from a bottle leftover from the last party and handed it to him.

We started talking—the usual stuff at first, like our lives and interests, but then the conversation shifted to more personal topics. At some point, he reached over and touched my leg. His hand was so soft. He looked me in the eyes and asked, “Do you like this?” I closed my eyes, and before I knew it, his hand slid inside my shorts. He barely touched the tip of my cock with his finger, and I let out a small moan. I couldn’t help it. My heart felt like it was going to burst out of my chest, and my cock was so hard it was straining against my shorts.

He stopped and handed me my glass, telling me to finish it. Then he leaned back and asked me to open his trousers. I couldn’t believe this was happening, but I complied. He wasn’t wearing underwear either, and his cock was rock hard. I was dying to taste it. I remember teasing him, brushing the head of his cock against my lips and lightly touching it with the tip of my tongue, like I was tasting it. He laughed at that.

Then I took him into my mouth. He smelled so good, tasted even better. I sucked him slowly, nervous that I might hurt him with my teeth. His hands started exploring my body—grabbing my balls, touching my ass—and he let out soft moans. Hearing him moan because of me was an incredible feeling. He asked if I wanted to move to the bed, and I said yes, but I led him to my roommate’s room instead. I didn’t tell him it wasn’t mine.

We stripped completely naked. He looked amazing—tanned all over, like he’d been sunbathing nude, maybe at one of the nearby nudist beaches. He touched my balls, looked me straight in the eyes, and asked if I liked it. Obviously, I did. He lay on the bed and suggested we do a 69. I didn’t hesitate. I went back to sucking him, and he started licking my balls and my ass. I felt his finger gently exploring me, and it was incredible.

Then I felt him grab something from his pants on the bed—probably oil or Vaseline—and his finger slid inside me. It was cool at first but felt so good. I was in heaven, and I couldn’t focus on anything else. I stopped sucking him because the sensation was overwhelming. Before I knew it, I came on his stomach. I was embarrassed and started apologizing, but he just smiled and told me to clean him up.

I grabbed a towel and came back to find him standing, my cum dripping down his stomach toward his cock. He looked at me and said he wanted to fuck me. He asked if I was okay with it. I said no. To this day, I regret not saying yes.

Instead, he asked me to suck him again, saying he wanted to finish. This time, I dropped to my knees, and he gently fucked my mouth until he came. I swallowed every drop.

Afterward, he got dressed, and I put my shirt back on. I thought he’d leave right away, like guys who disappear as soon as they’re done. But he stayed a little longer, finished his whisky, and told me it was really good. He said he’d love to see me again, and I told him I felt the same.

We did meet again a few days later, but that’s a story for another time.

People literally broke up over lack of sex or difference in lifestyles, 20 years sound like there could be major differences?

Hi everyone,

Earlier this month, I was visiting Palm Springs for Pride, and on my last day, I met this older guy. We hit it off immediately and have been in touch ever since.

We really connected—he shares my sense of humor and energy, which is rare for me to find. I love being silly and witty, and it’s amazing to meet someone who matches that vibe.

Since we started talking, it feels like we’re getting closer every day, which is exciting but also a little scary. I don’t want to move too fast because it has been a long time since I felt this way about someone and I want to make sure he's the right person.

One thing I’m unsure about is how to approach the fact that he enjoys going to expensive restaurants. I’m currently on a tight budget, and I want to make sure I communicate that with him without it being awkward or coming off the wrong way. I’d love advice on how to handle this and what kinds of activities we could do instead that won’t put a strain on my finances.

I’m planning to fly to PS again soon just to see him, and I’d love to hear any advice on how to make this work without messing it up.

Thanks in advance! 😊

I am 25(M) who had never been with a guy before, only girls. I started talking to a 51 year old at the start of August. We matched over tinder, talked every single day for 3 weeks, exchanging photos, videos, and phone calls. He knew that I was brand new to this and made me feel very comfortable to the point where he ended up flying me down to see him. I stayed with him for 3 days and had the best time of my life. He made me feel super comfortable in person and respected me. He was treating me like a boyfriend, bringing me coffee in bed, paying for meals. We even made a blanket fort and watched movies the second night. I instantly fell for him cause I get attached way too easily. I end up going home, and we still remained in contact. He always claimed he was “super busy” and he genuinely was, he had a bunch of travel plans he made before we ever talked. But it’s been 4 months now and we still haven’t hung out again. We still talk every day, but at times I notice he is very dry with me, and doesn’t put in any effort to make plans because he is “so busy”. Or something will come up out of no where. Other days he will be texting me every 30 seconds, and we have a great conversations all day. I’ve questioned him about it before but he promises me that there is no one else in the picture, and that we have a “connection”, and how much he misses me. But I notice that he’ll follow new younger guys on instagram, like their photos, and will be active on apps without responding to me. He’s even gone to the extent of saying “I don’t have time for multiple boyfriends, you are my only one”. Obviously he can tell I like him, but I don’t want to seem crazy and keep calling him out after he will swear that I’m the only one. But I feel like I am 99% sure I am just another boy on his roster, which isn’t cool with me. To give you more context he is retired, and extremely wealthy. He has multiple homes, one being in my state (for the summer) and the other in a warmer area for winter. Give me any advice! Or similar situations please. Cause I feel like I’m driving myself insane over this.

I was 18 when I had my first boyfriend. He was 57. I remember taking the train from Den Haag to Amsterdam, and he pointed out the building he used to work in, and in Amsterdam, after dinner, we walked to the house he used to live in as a young man. It had other tenants now, as the lights were on, so we walked away.

On the way home, I said to René that I could not comprehend that he had such a long life before I was born. He said that someday, I'd have a whole life of my own, too, and he wouldn't know anything about it either. I felt my stomach drop because there and then was a sense of an ending. We tried to stay together for another year, but then he... faded away. The truth still lingers on as he was right; I had been doomed to roam this earth, knowing that I could have shared my destiny with another and not the others. You never forget your first, I believe.

I thought he'd be the only older man I'd ever date. But, cut to now, of course that wasn't true. I went on to become a blogger for a good number of years with hundreds of followers around the world. I was hated but ultimately loved for trying to sanitize age-gap relationships among gay men while decentering casual sex and abuse of all kinds. Furthermore, I was called pederastic and a liar. Ultimately, it mapped out my network on the globe, so it was a fertile effort. I can't recall, but some of the better things I wrote were that got a lot of interactions were: 'Do older men hurt the same?' and 'Time and space.'

I had forgotten of all my greatest hits, but when commiserating with Mr. Rodney over the impending death of my father, I said to Rodney that he had lived through the pain, and now he had returned to tell me what it all meant. In a sense, older men are time travelers and this was the essence of my essay, 'Time and Space.'

'Time and Space' was a meditation that explored a lot of my peripheral thoughts and feelings, a lot of them being romantic. Was I born too late, or were the men I loved born too early? If we grew up in the same city, would be just as distant or a little bit closer? Mr. Daryl, a reader from New Zealand, wrote back to me, and he said that I was indeed born too early, and that was something to cherish, and not to mourn over! Daryl stressed that I had done so much in my twenties that by the time I become an older man myself, I'd be somewhat prepared. Daryl said that I had so much love from different men in my life and that could only mean that nothing was too late, nor too early, and everything happened in its own time. He said that I had made him cry because I kept raising so many questions. He wrote, "Just how incredible is the fact that you had it at all?"

It's been a couple of years since the blog was shut down. Starting again after the pandemic wasn't easy. There were some bright spots, like I finally got to meet my pandemic pen pal, John Eric. John and I had a tumultuous relationship— one that required a lot of forgiveness— and he once said to me in a confident tone that one day, when I'd be an old man myself, I'd also be wise, and not just clever. And I wept. I said to him that when that happens, then I wouldn't be able to prove it to him. He'd be gone, along with everyone I loved. He smiled, and reassured me that I wouldn't need to prove to him anything because he was already sure of it.

Soon, it'd be a decade since I had my first boyfriend. Sometimes I think back on us, walking hand-in-hand at a Christmas market somewhere in Holland, and just how young and beautiful I was. And how I have outlived his ex-boyfriend, whom he grieved so much over. I met a wonderful friend, Marc, who introduced me to a running club full of gay men. They are friendly and diverse, and they save most conversations for the night, spoken behind closed doors, for some things are easier to confess in the dark. A very old enemy, Mr. Texas, was very surprised when I mentioned Marc and Rodney. He said to me that I once said, "I only have partners and all my friends are my exes." Shocking, but it wouldn't be out of character at a certain point in my life.

I grew up in a small town believing love wasn't real for gay men, and in my adulthood, I thought life wasn't real without love. I spent my youth pursuing it. Now I keep my hair short and dark to cover up the fact that my hairline is softening, and I wear makeup a little differently to hide the hollowing of my face. Recently, I had the pleasure to meet a very old friend. In just several years, I feel like he had aged so much faster than I have. Now he takes longer to rearrange his features every time he bursts into laughter, or rather, wheezes through the tube in his face. He likes stories, too, and he said I was an elf, burdened with a long life and many goodbyes. I told him I thought I'd never see thirty, and he reached out his hand to caress my face. He said he barely recognized me anymore, and I laughed because I still felt the same every time I looked too closely in the mirror. Pressing his palm into my face, I asked if he still believed it when he had said that one day, I'd make a man very happy.

"You've made me happy," >!redacted!< said. "Are you happy?"

Then we sat there in silence for a long time while the caregivers walked past his bed, and the surrounding machines beeped and blinked.

Hey everyone, I’m 25, and as the description suggests, I’d describe myself as a fem bottom. Most of my past dating and sexual experiences have been with older, top men, which I’ve come to realize was influenced by my relationship with my father ( daddy issues you could say ) something I’ve worked through in therapy.

While I’m now open to dating older men without the same baggage, I’ve been trying to explore dating guys my own age. Unfortunately, it often doesn’t click for one reason or another. Recently, I’ve noticed more younger guys approaching me and while I’ve connected with them on a much deeper level than guys my own age, I can’t shake the thought that I’m the older one.

I’ve met someone I really get on with but he’s 22 and his age keeps nagging at me. Any advice on overcoming this mental block?

Hello, to understand how I feel I guess you need some of my story. I’m 24 years old I started with Mark when I was 21 and he was 37. During a while being with Mark was amazing but then we got to know each other a lot more and I realised he drank a lot, probably back then it would have been every 2 days, which it worried me it wasn’t like drinking a glass of wine during the night and that was all, he used to drink many drinks a night. Anyways we moved together after 1 year of relationship and while we were living together I could see all this, there was so many arguments too, normally cause he was drunk and started them and I just couldn’t put up with this behaviour so I used to answer back. So after a couple of months I decided to leave because I was exhausted of this, I was feeling like shit in that house and used to cry everyday. This meant we broke up too. As he was contacting me every now and then and making me feel worse for the decision I took I blocked him on everything, not that I hated him I just wasn’t comfortable with the conversation we used to have.

After a month he reach out to me through email, we met up again and came back together with the condition he would stop drinking for a while to prove he didn’t need the alcohol and after that the relationship with the alcohol would change as I couldn’t put up with it. For a while he said he didn’t drink, I believe he was honest but I wasn’t with him all the time every day of the week. After that he went back to drinking but not as much as he used to, there still was a weird atmosphere if we went out he normally said things that will trigger me to argue but I just didn’t answer back to be able to save the argument.

Then the drinking started to get worse again, it was more and more days every week… I tried to be fine with it but I just couldn’t maybe is cause my mom is an alcoholic and even if she doesn’t drink anymore I didn’t want to re experience all that trauma.

For a time skip we go now to our 3 year anniversary almost a month ago, one of Mark’s friend was over so we were spending time with him. I booked off from work to be able to go on holidays with mark for our anniversary but even when I tried to plan things everything seemed negative so at the end we stayed home. I got loads of time free and his friend too so we used to meet up, he realised Mark was drinking so much almost every night, and coming back really late home, during all this time Mark told me he didn’t have any problem with the alcohol, it is different cultures and in my country people doesn’t drink as much. But his friend was from the same place and he thought it was worrying too, so for the first time I felt validated.

The day after our anniversary the 3 of us went together for a couple of drinks, me and his friend were leaving after 2 drinks cause we didn’t fancy staying until late, Mark walked out to the door with us and argued with a guy, got into a fight and when his friend tried to calm him down Mark punched his friend. I tried to go and do the same but he punched me and put me on the floor bleeding from my nose. After this I left him on the bar and came back home with his friend. Picked up everything I remember that was in his house and wait until he came back to leave ( I wanted to make sure he made it home safe cause he was really drunk, I feel so stupid I still care to be honest )

Next day he asked me what happened as he didn’t remember, he apologised but really didn’t apologise much if I’m honest, it was more like “ I’m sorry I didn’t mean to hurt you, it’s not an excuse I was drunk “ he didn’t even suggested trying to overcome this in the relationship… well he told me he recognised he had a problem with his relationship with the alcohol too.

Since then I haven’t met up with Mark, we have texted mainly to ask how each other was but never into a long conversation or anything. He normally says he is fine he doesn’t really tell me how does he really feel, I’m honest when he asks and tell him I feel bad cause I don’t there’s any point lying and saying I’m fine when I’m obviously not.

And last night I got a message from a person we both know sending me a screenshot of his tinder profile. Got really hurted, even when I know we are both single so he can do anything he wants. But still hurted me I can’t even go through the day without thinking about him and feeling bad and he is already in dating apps trying to meet up new people, I try to think he cared for those last 3 years with me and he is just trying to fill the gap I left quickly. I just don’t want to feel I tried that much to be with someone and help that person and he doesn’t even care. Which I don’t believe it’s the case, or at least I don’t want to believe it.

So I guess the advice that I want is, is there anything I can do to get through this in a better way? I’m trying to make me meet friends even when I don’t feel in the mood, I try to keep my mind busy when I feel so bad to not get crazy.

Do you think I did well leaving? Sometimes I feel like I gave up but I don’t think I could handle much more and that night it really scalated up…

I was just reminiscing about this hilariously awkward encounter with an older top. We’d both had a few drinks and were heading back to his hotel room. I told him I needed to use the restroom in the lobby first and would meet him upstairs. But, of course, I got completely lost trying to find the room. Embarrassed, I went to the front desk and asked which room was under his name. The receptionist called him up and said, "I believe your son's lost."Absolutely mortifying.

Hi all, a bit of a weird question and I appreciate the majority of people here aren’t in to older guys because of daddy issues (/vice versa, so did not mean to be offensive.

I only recently started seeing guys (4-6 months ago) and am only in to significantly older guys. I had a really bad relationship with my dad and am really only in to guys that aren’t respectful to me at all (facefucking, slapping, mean words, really rough sex etc). Just all round quite degrading.

I feel on one hand it’s okay because it’s the only thing that really attracts me sexually and I think it makes me happy in the moment. But also a bit messed up and after sex I feel a bit worthless sometimes which makes me sad. Really not sure how to deal with this, any advice welcome!

Im 21 now and when I was 18 when I. met this 45 y old man on the apps. He was by far the best I’ve ever met. He was confident and comfortable in his skin. Attractive and so kind. I was deeply in love with him. I was obsessed and I admired him a lot. The sex was amazing and our relationship grew stronger every day. We’d say things to each other and our time together went beyond labels, beyond just sex. We’d eat dinner together. Hang out and watch movies. I’ve never experienced this level of attention from anyone else in my life. No ones has to this day treated me the same. I don’t think I’ll be able to go back to ever being the same, he’s permanently changed me, and now I can’t stop thinking about him.

Blonde blue eyes slim and fit younger, I had no problem finding good tops and they were older for the most part. Now that I am older, yet still blonde blue eyes fit but muscular, I am still a bottom but because I am now older, it is expected that I be a top. I've tried to switch and top because it was then easier to meet but I just couldn't. And I guess the opposite is also true: that it is expected that younger be bottom?

When I (M30) was growing up as a young gay man, there was a floating comment that went around my community which went to the tune of ‘make sure you’re with someone by the time you’re 30, that’s gay death!’

Gay death! What a novel yet dangerous thought. Part of me had been dreading my 30th since hearing those words, even though I have a wonderful partner (M24).

I just wondered if there are any other experiences like this that you guys had growing up, and also what do you guys perceive as being ‘old’ as a gay person?

Now that the birthday has passed, I’m looking forward to my 30s as a sober, happy and exciting time, but gosh knows I had that imbedded apprehension to age!

I was 18 yo and still living at home, and I was looking for a part time job. I received a message from my school that there was a weekend job opportunity. I called the phone number and spoke to an older gentleman. He had a home that needed landscaping and painting done. He lived an hour away and I had no car. We lived in India at the time, and I really couldn’t afford to pay for transportation. He was a Desi businessman in his mid 50’s, and his office was closer to my house so it was agreed that he would pick me up on Fridays after work and he would bring me back on Monday mornings when he drove back to work. (I later found out that he had a friend on staff at my school counselor’s office and his friend had recommended me for the job because he thought I might be gay).

I had never had sex before, but I already had been having thoughts that I might be gay and that I was attracted to men. When he arrived, he was a Daddy type with a heavy mustache and was wearing a nice. suit. He was a little overweight but I still found him attractive. I went to get in his car, and he told me to sit up front with him. As we were driving, he loosened his tie and I could see he had a hairy body. He was easy to talk to for being a perfect stranger, which surprised me because I was a shy kid. I could also see the outline of his boner in his pants, which looked pretty big and he often touched himself. I didn’t say anything, but I liked thinking about his hairy chest and big cock! I did mostly yard work at his house that weekend. Nothing else happened that first weekend other than that he would sometimes walk around the house shirtless and he wore loose boxers that showed the top of his very hairy bush and a big cock bulge. There were a few other signs that happened that weekend. When he dropped me off at home, he asked me if I still wanted to come back to work at his house the following weekend. By me saying yes, I was pretty sure he knew that I was OK was everything.

The next Friday he came and picked me up and he was much more forward in showing what he wanted. On the drive to his house he reached over and started holding my hand. I remember feeling really close to him when he did that and feeling attracted to him. He eventually put my hand on the boner that was showing in his pants and he asked me if I liked it? I was really turned on and he knew it. When we walked into his house, he told me how beautiful I was, he hugged me and kissed me, and I could feel his hard cock pressing against my stomach and his hands were grabbing my ass.

I was really nervous but horny at the same time. I trusted him and he was always very kind to me so I was happy he was going to be my first sexual experience. He asked me to pull his pants down for him and I did. I had never seen a grown man’s hard cock before. He was really big and he signaled for me to put his warm stiff cock in my hand. He asked me to suck it and he gave me some directions. He then told me to stop and asked if he could pull my pants off so he could see my cock. When he pulled down my pants I was embarrassed that my underwear was so wet with pre-cum. He said he loved it and he started sucking my cum soaked briefs and my cock at the same time. It felt amazing! By the time he put my dick in his warm mouth I pretty much shot my load immediately while his fingers were fucking my hole!

He asked me to start sucking him again. He then told me to stop because he was getting close to cumming. He started licking my hole and fingering me again. He took me to his bed, and I laid on my back as he played with my hole again and he got me relaxed enough to enjoy several of his fingers inside of me! He then says, I think you’re ready, as I feel the head of his big cock pressing against my hole. He told me to just relax, and he kept kissing me as he kept pushing his cock slowly and carefully inside of me. He would pull out and add more lotion to his cock and he kept sliding back in until I felt his stomach against my ass and his whole cock was inside of me! It felt amazing, he kept saying it felt so good, breathing heavily and his moaning made me so horny! I shot another load, and then his body trembled and I could feel him shooting loads of his warm cum inside of me at the same time!

This was the first of many weekends that I spent with him.

Ive always been attracted to younger light skinned guys, but everytime i meet one is like they either fetishize my size or they just want a one night stand and ive never hooked up. Why is it so hard finding someone? Do i really have to lower my standards? Ive been alone for 3 years, last relationship lasted 14 years and it was with woman. Never really had a relationship with a man but i have always wanted to. Maybe too much!

I'm a younger guy and have a particular fetish. I have always had a thing for older men in capes and long robes. Especially Dracula. Even from an early age I can remember being drawn to Bela Lugosi and other older men like that. Today, I know I have a fetish/kink for a dracula-esque type gentleman.

I'd love for an older men to slowly seduce me, lead me to bed, and cover my naked body in his cape. I'd love for him to suck on me (no blood or hard bites) and tell me how he wants me to become his. It would be awesome for it to be sensual, him exploring my body (I have a athletic build w/ a smooth body). I'd even love to top him or have him top me with his cape on (and it could only be his cape on draped over his body).

I have met one older man who let me live this out, where he wrapped me up in his cape and gave me hickeys across my lower neck, and sucked me with the cape on until I exploded in his mouth. Any other man I've mentioned this too seems a bit weirded out by it, so I'm wondering if you would be too.

I 28 yrs old, I'm going to meet an older guy 50's but he is side, I have never dated a side dude before. What should I expect concerning the bedroom drama? I give oral but I don't really like receiving it. I like it deep and hard inside of me but this guy doesn't do anal which means he will not bend me over.

I'm 39 and I've always liked older men but when I was younger they were probably closer to their '40s to '60s . Ever since I turned about, 21 I've had this intense attraction to senior men. I tried to make it work with someone, but he was already past an age where he really wanted to have a relationship. We dated for years but he never actually wanted to be married. He ended up being my best friend and died at the age of 79 in 2019.

Then when I was in my my mid to late twenties, I met a friend who was a deacon who was very sexy and the last time we did it he was probably in his late '70s.

My general attraction range tends to be about 20 years older than me and that works currently for me, but I still have this attraction that almost seems to just be a fetish.

I haven't done anything with someone that age in a couple of years, but anytime I see somebody that age online or on YouTube, it makes me really horny.

How many others feel this way?

I'm a 19 year old trans man, who's very naive. I'm aware of this. I'm looking into getting on the dating apps. I've always been into older men, as long as I can remember and as such, have waited until now to start dating. I have had a few relationships in the past, but, not real connections. How do I watch out for red flags?

I have been seeing an older guy for a couple of months now, under the pretense of us being FWBs. However. we're currently facing some issues managing our expectations for one another in this relationship.

For background, I (28m) have recently gotten out of an extremely toxic 3 1/2 relationship with another older guy. That broke down due to him being an serial cheater and liar. Because of this, I don't have a desire to be in a committed relationship with anyone right now (and from being partially jaded by older men being incapable of communicating what they actually want). However, I'm not opposed to trying again if the right guy comes along.

For my friend (50m), he was married to his husband for several decades now. Due to sexual incompatibility, they opened their marriage. During the first couple of months of us seeing each other, we've gotten closer together and opened up more as time past. However, about 2 months ago, my friends husband unfortunately passed away. He's been going through a lot of other things prior to this happening, so I expressed my desire to be there for him whenever he needed someone to be with or talk to.

The main issue with us, that has been present since the beginning, is that our expectations for one another is misaligned. Prior to his husband's passing, I handled this relationship very cautiously. I wasn't going to be investing too much time and energy into it as he already has someone else that he can rely on for emotional security. There also was a theoretical ceiling on what our relationship can grow into as I'm not competing with his husband of 25+ years. In my mind, It was mainly for the sexual connection we had. Anything else that he was comfortable with, and that he initiated on his end was a bonus. He also voiced concerns with sexting over messenger, and spending more than what seemed like an hour at my place whenever we meetup; in an attempt to not disrespect his partner. This would make you think that he also isn't looking for a strong emotional connection with me. Completely understandable in my eyes.

However, he simultaneously thought that I was too distant, that he thought he liked me more than I liked him, that I don't text him back fast enough and didn't respect him (albeit I'm not the most responsive texter in the world). To me, this sentiment doesn't make a lot of sense. Does he want a FWB, a fuck bud, or some poly-relationship? Not sure exactly what he wanted at this stage which caused a lot of confusion and misunderstandings between us.

Things obviously changed a bit between us after recent events. We've definitely opened up to each other more than before. He's visiting more often, and we're doing a lot more 'Netflix and chill' type activities now compared to just a quick hooking up after work. We're texting more often as well and I'm making more of an effort, compared to before, to be there for him due to the recent chaos in his life. I'm also very aware that he is going through a lot at the moment, and might just be looking for a distraction from it all, so I'm not suddenly expecting us to get in a relationship now. I don't think I want that right now either.

However, we got into an argument recently when I asked if we could spend more time together, and if he would like to spend the night over sometime. Me asking this seemed to indicate to him that I wanted more out of this relationship, so he stated that he's not looking for one, that he urges me to keep my options open and see other people to find happiness, and that we fundamentally wouldn't be good partners as I'm more introverted and he's not. This mind fucked me a bit for a couple of days as I thought he was seeking this type of emotional connection throughout the entire time we were seeing each other. And I made no comments on wanting something more exclusive the last time we were together.

The argument led to me telling him to explain to me exactly what the fuck he actually wanted and was looking for. My patience for guys not communicating clearly to me was already thin already, so I wasn't entertaining whatever we were doing anymore until he was clear with me. He recently sent over the below points in an email. Now I'm just wondering if all of this is too much to expect from a FWB or whatever our current dynamic is. I was fine going with the flow but now I'm getting a bit exhausted with this.

• Stress free, relaxing, and pleasurable time with someone I trust, enjoy, and feel a connection with
• Someone I can learn from, be stimulated by (intellectually and physically) by expanding rather than just mirroring my own experience
• A two-way, mutual sexual energy and connection that is grounded in honesty, equanimity, and shared attraction, physical chemistry, and expression
• Compassion, support, and understanding of my stage of grieving, pain, and transition
• Emotional connection and ease when together
• Being fully present in the shared pleasure of the moment, and a shared commitment and valuing of lack of pressure, guilt, or stress about where or how the relationship will evolve
• Mutual reassurance of each other's worth and compassionate support and understanding of each other's individual needs, desires, fears, inhibitions, hindrances, and emotional history that could impact the pleasure of being together or each other's personal experience
• Validation of my self worth and desirability - and opportunity to mirror back the same
• Genuine trust and acceptance of one another - in the moment (not past or future)

He is a very sweet, empathetic, smart and handsome guy, something I didn't highlight earlier in this thread. This also is all coming from my perspective alone. In his email, he highlighted things on my side, that I'll be addressing with him separately. But I do want things to work out between us. Any advise for me or him on this matter would be much appreciated.

Where the love shows through in their videos

My BF cheated on me a week before my birthday!

Hello guys! I'm in my 20's and my BF is in his 50's now. We've been together for 5 years and it is a Long distance relationship, I love him so much like he's the first guy I fell in love with coz I'm attracted to older/mature guys. He's an aussie btw and I'm asian, We met a few times and supposedly this year I will process my visa to be with him, however a week before my birthday I discovered he visited his ex in thailand and they went to taiwan with his ex's family without even telling me, He said that he is sick for a few days but then I felt something is off - It's like my intuition kicks in and tells me check his social media and right there I checked that he got tagged by his ex's mom and yeah I confirmed that they were together.

And Immediately I messaged him if he's in Australia coz he mentioned to me that he's sick and he never responded to me. I tried to call, text, chat him in all of his social media account even facetime him but he never picked it up but he saw all of my messages on WhatsApp and messenger, He just ignored me and it hurts so bad coz we already plan everything like our future together.

He said after my birthday I need to process my visa to be with him and we planned it for 5 years and I never thought it will be gone in just one snap - I gave him everything coz we've been together for 5 years and he's the only guy I slept with. I've been very faithful and loyal to him even we have a huge age gap because I thought he's mature and he doesn't want any drama, I thought when you are with someone who's in their 50's you are secure that he will never hurt you but I was wrong and I was crying so bad for weeks because I loved him so much - The feeling of getting ignored and being dumped after of years together it sucks and I never thought I will come to a point where I beg him to respond to my chat!😢 Like I step down in that level, Beg him for attention or atleast call me or message me when he's free to talked about it and save our relationship but he never did - until now he still ignoring me, But I hope he's okay and I still wish him a good luck and a genuine happiness even though I don't have any idea if he's with his ex by now.

I'm mad YES but I already forgive him for what he did, Life is too short for me to cry on one guy! I still have faith that maybe someday, one day I will find a mature guy that will love me sincerely even though to be honest, I'm afraid! I'm so afraid to trust again but I'm pretty sure there's a lot of mature guys out there who are sincere and not a cheater!

I'm sorry guys it's a long story for me, I just really need to let it out! Always be kind and spread love and positivity in this world! Love you guys!

21m was on sniffles looking when a older guy messaged me 55m. I typically don’t respond to older guy but he lives super close to me so I responded. We hit it off right away. We sent pictures back in forth. I’m pretty average cock size but he was probably 8inch and thick. He invited me over sometime on the next few days to hookup and he would top me.

I’ve never hookup up with an older guy or bottomed so any advice or tips.

My BF(49) after being together for a few years has been cheating on me for about a year now.

I know I should have left when he had so many red flags but I chose to stay on and I’m just dumb founded. To a certain extend I felt like I deserve it for ignoring all red flags.

I’m just here to rant, needed an outlet. I lost my job , fell ill and now found out he has been cheating for a year now. I’m exhausted, disappointed , angry and given up. I have no motivation to move on.

Thanks

Hey guys,

I was wondering if anyone had any advice or stories similar to my situation.

My partner (70) of 7 years and I live together but we don't have sex. We're still intimate but it's very much me driving every single thing regarding physical or emotional outreach. This in isolation is and has been manageable. Still in love so I can handle being the instigator.

But lately I'm feeling like I need to reconnect with my family and that I'm wasting some vital years and experiences witout them. We live a large distance from each other. They are a couple years younger than my partner. I see them like twice a year and I don't want that to continue... Id like to make effort to relocate closer to them.

I just feel like I'm in this relationship where I'm responsible for the emotional functioning and I'm getting a bit tired of that and would really like to spend some time closer to home. My partner doesn't want to move at all and is comfortable here which is totally fair.

I really miss just seeing my parents for a coffee or calling in when coming home from work. Instead I come home to my partner (who I love dearly) and just feel a bit resentful that I have to provide twice as much emotional and physical presence AND also miss my family who are great emotional supports.

Has anyone ever had this dilemma of personal relationship vs aging parents? I feel like I'm in a tough spot as my partner and parents both age.

I hear this place is somewhat like a gay Mecca, with lots of older “Daddy” types there as well. I’ve never been to New England but I’d love to visit. What would the vibe be like for a Black youngish-looking guy? I want to go alone but I don’t want to look misplaced for going to a place that I think caters mostly to older men.

I’m 31 and been on a look out for daddies (chubby daddy bears to be specific). I get called ‘boy’ and it seems to be the norm in the leather community to indicate that this is a sub role and not necessarily the ‘younger partner’. I’m flexible with that being vers and typically like to switch positions with a daddy.

But I like to be called ‘son’ more than ‘boy’ because to me that is more intimate and endearing to the point where it gets me aroused.

I sometimes feel like they are hesitant to use ‘son’ as an endearment (which I LOVE btw) in a conversation because maybe I am too old to be called one. I’m not even sure if it’s the age or it’s the look because I’m a bear and have been called ‘daddy’ by the younger folks. It’s nice to hear but I’m almost never interested in guys my age or younger.

I think the question lies here for the daddies of this sub:

1. Do you feel the same kind of endearment to call your younger partner ‘son’ in bed?

2. I can understand that a strictly dom daddy would feel more empowered to call a partner ‘boy’ than a ‘son’ but are there things/traits that make you avoid calling them a ‘son’?

I live in a college town where a majority of the college students are toned and all seem to be over 5’9. I am chubby and 29. Not exactly college age anymore lol so it’s TOUGH trying to even make friends here and gets very lonely. I met this 59 year old guy recently though and we really hit it off!

We planned to meet and go for a walk and get lunch. We met for the walk and we were both nervous. I saw his pics before meeting bur he was still nervous that I would reject him. I was all over him and enjoyed what I saw. He looked like a taller, slightly balder Rick Moranis from Honey, I Shrunk the Kids. I have a real soft spot for nerdy looking dad types. The walk was great, lunch was great and then he asked me what I wanted to do or if I wanted to leave. I asked if we could go to his house to watch tv together and he agreed. When we got to his house I was full of nervous excitement and he asked if I wanted to cuddle and watch tv in bed and I agreed. He walked in front of me and I was getting more excited so I began to undress on the way to his bedroom. By the time I was at his bed I was down to just my underwear. He saw and didn’t say anything but instead took his clothes off and the tv never came on.

For the next hour and a half we cuddled, made out, he topped me a little bit and we just played around. His closet doors are mirrored and reflect the bed and seeing this man more than a foot taller than me all over on top of me was really turning me on and when it came time, I came REALLY REALLY hard. My head was still throbbing for a little while after kinda hard. He came hard too and then we cuddled some more until I fell asleep and began drooling on his chest. He woke me up and I apologized and he told me he really liked that and it made him happy but that he needed to meal prep for the week. I left and we ended up making plans to have lunch today! I’m excited.

So long story short, we have the same kinks. I've only met with him in person a couple times as we are long distance. But after our last meet (we had two nights together) I kinda am getting some red flags from him. Like, I have basically discovered that our values don't line up.

I think he's most likely racist and misogynistic, but avoided having a discussion with him there and then (I have a tenancy to avoid conflict). We were also drinking together, and when he was getting more drunk he started brining up his ex-wife and pretty much how hard of a time he had with her.

We're apart again, I can't help but feel bad that I'll be hurting him if I open up a discussion about my concerns. I do have feelings for him which makes it all that much harder. I also shared some personal things with him which I think opened up wounds a bit so I'm feeling particularly vulnerable.

I'm wondering if anyone else has found themselves in a similar position, and if so, how did you resolve it? Resulting in either breaking it off or reconciling. However I don't think values like that are easily turned around at all.

Heads up, this isn't anything deep or too interesting, more for me to remember details as I want to remember them in the future :)

So, I was cruising on scruff as usual, I've been using it on and (mostly) off for the past 3 years (I'm 21 now). I'm not confident in my physique at all, so I always psyched myself out so I never met up with anyone. Finally, I matched with one of the hottest men I've seen, who also shared interest in me. He was muscular (under a layer of fat, perfect body preference for me), perfect age range for me (late 50s), nice and complimented me, and very respectful of my comfort zone. His texts were dry as shit, but I figured it was just how you gen Xers type (dad types the same way). I almost thought it was too good to be true, but I'm very glad I went though with the plan.

Met up at a bar, my god he was gorgeous. I feel we made decent conversation, its difficult talking to someone 2 generations of separation, but we made do. Talked about school/job/background etc.. Nearing about 30 minutes in, weight came into the conversation and I mentioned how he had 50 pounds on me (most of it muscle), and 1 drink was enough. Popped an instant boner, just thinking about him on top of me with his bodyweight. I popped out of my conversation coma and figured he is probably waiting for me to make the move (later I've read on this sub that you older gents don't want to look like a creep, and wait for the younger to make moves). He confirmed as long as I am comfortable with meeting up (YES, of COURSE) and we left the bar.

Outside the bar he mentioned something and I got the vibe he was expecting me to make a run for it, and I thought "That's funny, I've never wanted to not run away more than now."

We got to his place, and began with kissing. I am obviously completely new, made clear in our texts I've never even kissed before, never had any want to really. Turns out, I LOVE kissing now.

Got on the bed, undressed, he sucked me off first, then I tried sucking him (terrible at it of course, but was very enjoyable). Told him how I'd never even touched another man romantically, got to "pet" him, he pet me, jerked him off, he topped me, and kissed the whole time between and during moves. I asked him to flex, and got to squeeze his muscles, pinch his nipples, he felt me as well. It was euphoric! He kept mentioning how hot I was, and I would always remember I should also probably be vocalizing how hot I thought he was. At one point he wanted or I asked to top him, but I was just too soft from nerves/excitement, but he was understanding. We just kept kissing and exploring each other. He told me he didn't like his belly, I playfully got defensive and told him it just makes him hotter. I finished cowboy straddling with him inside me, he finished jerking off. After, we spooned for what seemed like 30 minutes, turns out it was like 2 hours :D

I unfortunately had already made plans with a friend early the next day, and didn't want to bother waking him up early in the morning, so I excused myself and told him I would be excited and VERY down to meet up with him again. I hope he didn't take it the wrong way, but I don't have much of a way to know.

I texted him a few times later, asked him if he wanted to meet up again, he reciprocated it but I left the ball in his hands and hasn't responded :(

Things I learned

What I did was stupid (unprotected, no condom. prep etc.) I've gotten my blood done and I'm clear, but it was a stupid mistake and nobody should ever do that on a hookup. Granted, he was tested and negative on his profile, but people lie about that shit.

I wish I was more patient with myself, such as when I trying to top, sucking him off, taking the whole experience slower

I like frottage and kissing way more than I knew before

I need to vocalize my thoughts and feelings more during sex

Notice when to make the first move, as I said earlier.

I can't expect someone who I've had sex with to want it again

The whole experience motivated me to become a better man. I've started to work out, eat more (I'm a twink, no muscle definition), and I'm trying to make myself a better sex partner (or partner, in the future). If I am having sex with 10/10's who take care of their bodies, I should also be taking care of myself, otherwise its not fair in my eyes.

Ill add more if I think of them!