Gay College Student ISO Mature Man

I am a 22 year-old film student looking to meet a mature top man over 50 who knows what he’s doing. Is that you? I am a bottom and I’m open to new experiences.


Last fall, when I was starting my graduate studies at NYU film school, I found myself sexually frustrated and unhappy with the guys I was meeting. The sex was OK, but nothing really special. I think that’s kind of understandable because, after all, we were mostly all in our early 20s and not very experienced. Plus, if I was to be really honest, the guys I met (and I include myself here) were kind of immature and unworldly. We barely knew who we were, let alone capable of thoughtful, meaningful and satisfying sexual relationships.

I guess that’s why I have always found myself sexually drawn to older men. I had never been with someone more than a few years older than me. But older guys seemed attractive to me. I’m not sure why, but I was really curious about what it would be like to be with an older man. I don’t mean ancient, of course, but I think there is something incredibly magnetic about a mature handsome man who is in his 50s. A guy of that age would be down to earth, mature and sexually knowledgeable, right? They would have so much experience, would know who they are, and would be beyond the petty insecurities that young guys like me are all so much about. I mean, really, so many of guys my age don’t seem to know who they are. They don’t know what real intimacy is all about and, fuck, they can’t even have a conversation. And really, let’s admit it, sex lasts about 10 minutes. There must be something better out there.

I was about to leave New York for a semester abroad at a London film school, but wanted to work through this confusion. I knew I was curious about older men, so I decided to explore maybe finding someone like that I could talk to and maybe go from there. And I wanted to do this before I went to London because, maybe, I would have the confidence to explore older guys there, too.

From the safety of my phone, I changed the age setting in my Manhunt membership so that I would only see profiles of guys over 50. Usually, I had excluded guys that old, thinking they were trolls. Previously, older guys on Manhunt would chat me up which would kinda freak me out. I would block them and be rid of them. But now, I purposely restricted my search so that I would only see older men. Maybe there was someone cool and mature worth talking to. I had nothing to lose. Besides, if it got strange I could block them and close the app. And if nothing happened or even if something disastrous occurred, I would scurry off to London and get away.

Manhunt works pretty well for searching–well, hunting!–because it lets you set a lot of search preferences to zero in on exactly what you’re looking for. I set the target age between 50 and 60. Now don’t get me wrong—I don’t necessarily think that anyone over 60 is too old, but I kind of had in mind someone a tad younger than that. I set body preference to be average or better. I didn’t set any specific ethnicity–hey, I’m open to all types. As for sexual preference, I chose top. I wanted to find a true and total top who knew what he was doing in bed, who was confident in who he was, and who was searching for me: a solid handsome young bottom.

Here’s how I updated my profile:

Profile Headline: JonJ Profile Text: I am a 22 year-old film student looking to meet a mature top man over 50 who knows what he’s doing. Is that you? I am a bottom and I’m open to new experiences, fun and safe hotness. Please be DDF and cool. Don’t be lame. Position: Bottom Build: Slim Ethnicity: White Hair: Brown Eyes: Brown Height: 5′ 8″ Cock: 6 (cut) HIV Status: Negative Place: Host or Travel Availability: Ask Me Intos: 1 on 1, Dad/Son, Friends, Fuck Buddy, Kissing, No PNP, No strings, Role playing, Safer only, Straight/bi, Sucking

I tried to make myself sound confident and not juvenile. I didn’t want guys thinking I was stupid. I posted a picture of myself that was purposefully a bit blurry and vague. I wanted to discourage guys who steal pics. I’m not sure what I expected. Mostly, it was kind of like play acting. I mean I was sitting on my couch from the safety of my apartment. I had no worries. I could chat all I wanted with guys, and at any time I could simply turn it off and disappear from cyberspace. I was safe, protected from predators and liars and strange guys with diseases. But what the hell . . . I was horny and curious and thinking more and more about it.

As soon as I updated my profile and narrowed my search for the age and kind of guy I was looking for, my screen refreshed and I was greeted by a dozen thumbnail pictures of older men. This was a turn off. They looked old! I mean really old. They all had to be lying about their ages. They looked out of shape and appeared to be meth addicts. Some we’re showing of their cocks and armpits. A real turnoff. This was a mistake. I scrolled down the screen. There had to be someone who was halfway decent. But, no. I was glad I was cruising Manhunt anonymously. After a while I got discouraged and turned it off.

I made myself some dinner and started to feel sorry for myself. All I wanted was someone I could talk to, someone real and true that would listen to me and, hopefully, set me straight and make me satisfied by fucking my brains out in a way that showed they actually cared if I got off. I watched an old movie, which was a class assignment, and wrote a one-page summary on it. It was getting late. I smoked a small bowl got in bed, and was about to crash. But first, just for the hell of it, I checked Manhunt again and saw that I had a message!

It said: “Hi. You’re handsome. And nice profile. Check out mine and let me know if you’re interested. We should grab a drink sometime. If not, no worries.”

I clicked on the photo next to his message and it brought me to his full profile:

Profile Headline: BradDad Profile Text: I’m an experienced and aggressive bi top looking for a cool younger guy who likes men my age. You should be 21-28 years old, in shape, a bottom, know what you want, and not into games. Safe NSA play only. I visit NYC often so this could be a regular thing. Chat me up. Age: 55 Position: Top Build: Average Ethnicity: White Hair: Salt & Pepper Eyes: Brown Height: 5′ 9″ Cock: 7.5 (cut) HIV Status: Negative Place: Host Availability: Ask Me Intos: 1 on 1, Dad/Son, Friends, Fuck Buddy, Kissing, No PNP, No strings, Role playing, Safer only, Straight/bi, Sucking

He was pretty decent and good looking. Not an Adonis or anything like that. Mostly, he just looked like a normal man. His profile was solid, informative, and normal. He sounded comfortable in preferring younger guys. There was nothing flashy about him, and his profile didn’t have the usual smell of lying about it. He had two other public photos of himself in his profile, and they were pretty cool and average, too. One was of him standing outside somewhere, I think a park. And the other one was him with his shirt off. He had a decent body, though it didn’t look gym built. He looked a little younger than 55. The most amazing thing that got my attention is that our “intos” were identical. Damn!

Mostly, his profile and message didn’t make me feel threatened. I didn’t have the usual alarms going off in my head that told me to keep away. He just seemed like a regular normal guy. Nothing particularly special. Nothing weird. He didn’t seem to be sugar coating who he was. A cool average guy. I liked that his message didn’t say “Let’s fuck” or something like that. His casual invitation (at least I read it that way) to “grab a drink” was non-threatening. He didn’t seem to be looking to just jump in the sack. That he wanted to have a drink with me said a lot. He wasn’t clearly wasn’t a let’s-fuck-and-never-see-each-other-again kind of guy. He had my attention.

What the hell. There was nothing to worry about. Just me and my phone. I could always ignore or block him at any time.

I clicked reply and wrote him back: “Hi. Thanks for writing. You sound pretty chill. What’s up?” I looked at his photos again and pictured what it would be like to be with someone who was pretty much as old as my dad. I stared at his eyes and tried to get a sense of him.

In like 10 seconds the app showed that I had another message. It was from him! I wrote him back and then he wrote me back and it went on for a while. Here’s the message exchange:

Him: Hey, thanks for writing back! Nice of you. Me: No prob. Doesn’t take energy to be polite, right? Him: That’s true, but not everyone on Manhunt is nice. Glad you are. Me: Thanks. What’s up? Him: Checking out the scene to see if there any cool guys worth meeting. Me: You mean other than me? LOL Him: You seem worth meeting. Me: I bet you say that to all the guys! Him: Actually, no. Manhunt kind of sucks. Just a bunch of liars on here. Me: That’s true. Him: Do you ever get lucky here? Me: Rarely. Him: I like your profile. I don’t see many young guys here that are open to meeting older guys. Me: I am open to it. Him: Is that what you prefer? Older guys, I mean? Me: I don’t know what I prefer, to be honest. I’ve just been thinking about it a lot lately. Him: Why? Me: I don’t know exactly. Him: That’s cool. I don’t mean to pry. Me: No worries. Him: I’m Brad. Me: Jon. Him: Nice to meet you, Jon. Real name? Me: Yeah. Convenient, huh? Him: Brad’s not my real name. Gotta be careful. Me: What is your real name? Him: I’ll tell you if we get to know each better. Is that OK? Me: I guess so. Him: Whew, OK. So I guess you are cool with my profile. About me liking younger guys. Me: Yeah. I’m curious about it too. Him: What are you curious about? Me: I don’t know. Maybe what it would be like. Him: Do you have a boyfriend? Me: No. Him: Surprising. You seem really nice and are incredibly handsome. Me: Thanks! Flattery will get you everywhere. LOL Him: Just saying. Me: What part of town do you live in? Him: You mean New York City? I don’t live there. Me: Where? Him: New Mexico Me: Are you here now? Him: No. But I will be in NYC next week. I am there about three or four days every month. Me: OK. That’s cool. Why are you here so often? Him: Business. And meet cool guys like you. 🙂 Me: Good answer. Ha! Him: Tell me more about yourself. Maybe I should go first. Me: OK. Why? Him: Get this out of the way–I’m married. Me: To a man or a woman? Him: To a woman. Me: Oh Him: We can stop sending messages now if you want. Me: No, that’s OK. Just hadn’t figured that. Does your wife know? Him: No. Go on–you can ask me anything you want. Me: Do you have kids? Him: Yes, four. Me: Wow! Him: I’m not a terrible person or a bad husband or a bad father. I just like being with guys now and then. I’m very careful. Very discreet. Me: OK. I can deal with that. Him: Really? Tell me now before we keep talking here. Me: We can keep talking. Him: Thanks. So that’s what I wanted to be up front about. Tell me about you. Me: What do you want to know? Him: Stuff that’s not in your profile. Can you unlock your private pictures, BTW? Me: I will, as long as you do the same. Him: Of course! Me: OK cool. So what else do you want to know? Him: Why are you interested in older guys? Ever been with one? Me: Not yet. But very curious about it for some reason. Him: What reason would that be? Me: I’m not sure, to be honest. Guys my age don’t seem very smart or sexually interesting. Him: You may be right. I’m very experienced, as you might imagine. Me: Yeah, that’s definitely a turn on. Him: Is your dick hard right now? Me: Yes. Him: That’s a good sign. I have to sign off. Are you interested in meeting me when I’m in NYC next week? Me: I think so. Him: I’ll take that as a yes, for now. We’ll chat more here but I have to go. I’ll unlock my photos. Me: Thanks, me too. Him: It’s been really nice talking with you. You seem like a really cool and normal guy. Me: You, too.

I signed off and immediately started jacking. I wasn’t quite sure why I was so turned on, but I was. I was hard as a rock and totally ready to blow. I pumped by bone furiously, thinking about Brad and what it would be like to be with him, which seemed somehow obtainable. Our conversation via message was nice, easy, not perverted or anything like that. We hadn’t even talked sex. Here was a normal secure guy who didn’t seem in any rush to convince me of anything. He seemed real, human and, I don’t know, just normal. That he was married and had kids really turned me on for some reason. It meant he was a true man who had obviously had a lot of sex and he liked to fuck. I bet he had a really awesome masculine technique, an average American masculine man. If I ever met him, I wondered how he would fuck me. I kept thinking of him as I pumped my cock and blew a huge load.

Exhausted and excited, I went to bed thinking of him.

Over the next several days I received more messages from Brad, or whatever his name would turn out to be. I never felt he was pushy. He was sexually curious, but nothing overtly creepy. Mostly, I felt he took an interest in me, that he was actually sort of listening. After quite a few exchanges he again asked if I was interested in meeting him when he came to town. He said he was busy during days, but that it would “cool to have a drink at a bar down the street” after a business dinner he had Thursday. He said, “Let’s check each other out in a safe public kind a way and we can go from there. Let’s keep it loose.” I could relate to that because that’s exactly what I wanted. I wanted safety and protection from something that could be potentially dangerous, let’s admit it. Meeting up with random guys in a hotel room or something like that was a set up for just about anything. NSAs like that could result in the guy having a gun or a large scary friend with him. Or he could turn out to be nothing like his profile and picture, like maybe a fat 85-year-old. Scary. But meeting him casually in a nonthreatening environment? I was game.

So, on Thursday, I met him at the Monkey Bar, a hopping bar on east 54th. I would be dishonest if I didn’t admit to being nervous. I mean really nervous, even though I was meeting him in a safe way.

I was a little late because I didn’t know what to expect but wanted to be ready for whatever happened. I didn’t get the impression he was a let’s-fuck-now kind of guy, but on the chance that it could go that way I wanted to be perfect for him. Better to be prepared, right? So I took a long shower and really scrubbed well. I shaved my cock and ass extra smooth, and I gave myself two lightly soapy enemas to make myself especially clean. I got dressed and undressed twice and still wasn’t sure I was dressed right. I wanted to be sharp but still casual.

All this made me a bit late. I got to the bar at 10:15. I saw him immediately when I walked in. He was in a booth toward the back. He waved and I made my way to him. As I walked toward him I saw right away that he was much better looking than his photos. It was gratifying that he hadn’t lied about himself in his profile. He was just as tall as he’d said he was, about 5′ 9″ I think. True, he wasn’t a giant, but he wasn’t a shrimp either. He looked pretty fit, although he did look a little soft in the belly. He wasn’t overweight; he was just a man. His hair was lightly greying. He was definitely a handsome man, with large eyes and vibrant sexy presence about him. I was immediately attracted to him.

He stood up as I approached the table and extended his hand. He said, “Jon, so great to meet you. I’ve been looking forward to this all day.”

“Me, too,” I said and shook his hand.

His handshake was firm and sensual. He held on to me for a long moment and looked me straight in the eye as he said, “Damn you are a good looking man.” After what felt like an eternity I didn’t want to end, he said, “Sit, please. I hope you don’t mind I got started without you, but I ordered you a drink.”

I sat across from him and saw that, sure enough, a drink was ready for me.

“It’s a dry gin martini,” he said.

“That’s my drink,” I said, impressed. “How’d you know?”

“Just guessed, but in our chats I kinda figured you were a martini guy. I like figuring guys out. If I was wrong, I would have enjoyed turning you on to it. Either way, I couldn’t lose.”

He took a sip of his drink, which looked to be the same as mine. I did the same. “Thanks,” I said.

“You’re nervous, aren’t you?” he asked.

“Sorta,” I said.

“Yeah, me too,” he said, although he didn’t seem it. He had a very casual and comfortable way about him that didn’t seem the slightest bit nervous. “Any time I meet someone like you for the first time I get very anxious.”

“You do this a lot then, I guess?”

“Not at all,” he said. “I’m careful as hell. I have to be, if you know what I mean. I have to be very discreet.”

“‘Cause you’re married,” I said.

“Yes,” he said. “I’m open about it. I told you right away the first time we chatted, right? You think I’m a terrible person?”

“Not at all. I’m curious about it, is all. You don’t get enough sex at home?”

“Actually, my wife and I have a lot of sex,” he said. “Amazing, really. Even after all this time. But every now and then I like the excitement of a man. I can’t help it.”

“I get it,” I said, and took another drink. The martini tasted great.

“So do you think I’m too old for you?”

I didn’t hesitate. “No.”

“Does being here with me excite you?”


“Why? Why are you interested in an old man like me? I’m old enough to easily be your father.”

“I don’t think 55 is old. It’s what I have wanted for a long time.”

“Why? Sexually, I mean, what turns you on about it?”

“Something about being with a very experienced guy. And that you’re married, and have kids like you say, you must be really good in bed.”

He smiled at me and took a drink. “More than good,” he said, the he asked, “Does that turn you on?”

I felt my cock growing in my pants. “Definitely.”

He leaned over closer to me and said, “I like being with younger guys like you. I’m not a pedophile or anything like that. When I do this, I only meet guys who are over 21. Young hot guys like you taste good. They taste good everywhere, their lips, their cock, their skin, their hole. If we see each other in private I will make you hornier than you’ve ever been before. But we both need to go into this with eyes open, if you know what I mean. Right?”

I felt warm all over. Maybe it was the martini. Or maybe it was his directness. “Right,” I said, trying to sound nonchalant.

He said, “I have a very hard time finding handsome young men like you who are open to older guys, and I’m very picky. Very choosy. You must have a lot of boyfriends.”

“I don’t,” I said.

“No way,” he said. “You are so good looking.”

“Thanks,” I said.

I felt his foot touch my leg. “Is this OK,” he asked. “Does this make you nervous?” His foot caressed my leg on the side of my calf, gently touching me, as if it was his hand.

I closed my eyes for a moment and said, “It feels good.”

“Listen,” he said, “if you’re up for it, we can go back to my hotel room right now. It’s just across the street. No pressure, Jon, really, but I would really like it.”

I heard myself say, “Me, too.”

He paid the bill and I followed him out of the bar and across the street, just as he said, to his very nice hotel. As we walked through the lobby I felt as if everyone was looking at us, as if they knew we were going to his room to have sex, that they judged us for our ages and thought very terrible things about us. I trailed behind him and started to feel really crummy.

He must have sensed my worry, because he stopped and put his arm over my shoulder. “Don’t worry,” he said. “They just think you’re my son.” He was right. No one was paying us any mind.

We walked down a quiet hallway to the bank of elevators. He pushed the up button. As we waited, he put his mouth to my ear and whispered, “Are you sure this is what you want? You can leave right now. I want you to stay, but it’s important that you want it, too. You need to want it more than I do, even. Because beyond this point you’ll be my boy and I’ll take you places you’ve never imagined. Tell me that’s what you want. Tell me you want this. I want to hear you say it out loud. Say it.”

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2 thoughts on “Gay College Student ISO Mature Man

  1. Willwig says:

    I can’t imagine why this post isn’t 5 stars. If your travels bring you to the center point between Charlotte and Atlanta, (GSP) please hit me up. Younger is my specialty and my handsome 47 y.o. hubby is on board. Experience here isn’t lost on any handsome guy here young or old because of our dynamic. Too much about us. We hope this story has a few more episodes with many happy endings and a happy ever after. Thank you for getting me so hot, My young hubby is going to sleep well tonight!

  2. Walter Kallenback says:

    Going to try the rope around my nut sack as I fuck, sound so amazing, the dog had the patience of a saint, I would have cum several times at least

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