r/OlderManPersonals

I am in the SGV and OC, and I would love to find someone local who just needs to be pampered. Are you a pillow princess? Please say hello. I don't care about your relationship status or the color of your skin. I'm not into playing games, just providing pleasure. Laid-back, respectful, intelligent guy here. Hope to hear from you! Have fun and stay safe.

​

Hey - I’m a tall (6'1"), educated, and successful guy who just got out of a marriage and is looking to have some fun with a younger woman. I’m very young at heart, travel a lot and am very active, so I am and looking for someone who would like to have casual, fun and intense sex with an experienced guy when our schedules allow.

As mentioned, I’m looking for a younger woman (18-22 preferably, but under 30 is ok too) for a consistent FWB situation where we actually click. I’m open to all races and body types; I’m just looking for someone clean, drama-free, and ready to have fun.

I get the most enjoyment out of pleasing you. I love breast play, going deep and taking care of your whole body. If you’re looking for an experienced guy who prioritizes you actually finishing, we’ll get along just fine.

I’m 6'1", 175lbs, 7” thick BWC, hazel eyes, dark hair. I’m HWP, DDF, and vaccinated. I’m in Southern Maryland, so hoping for someone close. Hope to hear from you.

I'll be right up front: I'm lonely. As cliche and overused as it may seem, 'looking for a connection' is what it's about. I need someone I can talk to, joke with, have serious conversations with and have fun with.

I consider myself to be witty and intelligent, and I’m attracted to the same. I enjoy reading, movies and binging favorite tv shows. I’m a musician; I’ve played guitar for over thirty years, and have played everything from classical to country to metal.

Very far left-leaning, and have lost all sympathy and patience for the Right. If that's your persuasion we definitely won't get along

Full disclosure: I’m married but needing something that’s missing. Real life always happens but I have plenty of time I can carve out for the right person.

If you're interested, feel free to send a chat and introduce yourself and let's talk. Open to 18+

Hello ladies…I hope this message finds you well.

I am a 47 M, educated, confident, charming man who would love to find a fellow open minded amazing woman to connect with.

Building a friendship in which we could allow to grow together, and explore would be ideal, connection and trust being the solid foundation of all.

I believe in open and honest communication, and expect your message to have a little bit of context ( aka no ☺️“hey“ or one word sentences or responses without verb ) after my effort in writing this post.

Open to a number of possibilities, scenarios and circumstances…reasonably of course and distances as long as an in real life relationship is realistic.

I know what I want and my worth, but you directly get Bonus points if your response paints a vivid picture of who you are and what you want.

About me…

I am attractive (yes, really), fit (work out regularly but not obsessed about it! Enjoying life is also important!), 5’10”, and very easy on the eyes ( lots of people seem to think I have an Italian/Spanish vibe to me), positive and laid back with a bit of a nerdy side.

I have brown eyes and darker features and a slight Midwestern accent when I’m comfortable.

I love cooking, reading, movies, animals, history, DIY projects, and music is a big part of my life as well.

Anyway…Send me your virtual carrier pigeon, I’ll take good care of it before sending it back!

Hugs and positive energy…

T

As you walk apprehensively down the road, you can hardly believe you’re really going through with this. Your heart is pounding, and you’re trembling uncontrollably with a mixture of nerves and excitement. Part of you wants to back out, but the thought of how proud you’ll feel afterwards for overcoming your trepidation and fulfilling such a naughty fantasy keeps you walking until you reach my front door.

Summoning up every last drop of courage, you knock tentatively, and after what feels like an interminable wait, the door opens. A mumbled "hi" catches in your throat as you hurry inside, head down, too shy even to meet my gaze.

I close the door gently behind you, show you into the front room, and make myself comfortable on the sofa while you stand awkwardly, taking in your surroundings and wondering how you ended up in this situation. Our eyes meet for the first time, and I nod gently at the floor space in front of me. You know exactly what's expected of you and, without a word, you take a deep breath and drop to your knees. The realisation that you’re already past the point of no return gives you a sudden feeling of liberation, so, gazing up at me and biting your lip, you start unbuckling my belt…

Within seconds my jeans are round my ankles and there’s a noticeable bulge in my boxer shorts. You murmur in appreciation as you impatiently yank them down, springing my rapidly-stiffening cock free. A couple of strokes with your hands ensures that it’s rock hard as you take it into your wet mouth.

It sudden dawns on you that you’re finally really doing it - giving a complete stranger a blowjob. The blood courses through your veins and your nipples harden as you warm to your task, slipping my cock in and out of your mouth, polishing the end with your tongue as you wank the shaft like in those videos you watch. You’re determined to seize the opportunity to showcase all your talents, and you undo a few more of the buttons on your blouse so that I can see your bra and flushed chest.

Before long your skills begin to have the desired effect on me, and you can feel my cock and balls start to pulse. You take my cock out of your mouth and look up at me, smiling, as you prepare for the inevitable, hoping that you’ve succeeded in summoning up a big load…

As you walk back down the street afterwards, you’re almost skipping with the thrill of knowing what you’ve just done. What would your friends, family and colleagues say if they found out? But you know that this is your slutty little secret.

=====

Thanks to Reddit I've met up with a few girls for this over the last few years, so I know it does happen!

All levels of experience welcome - I don't mind whether you're an experienced cocksucker who enjoys showing off her skills, or a relative newbie (or first-timer) looking to learn or improve.

I'm white, 47, 6'1", average build (gym-goer), clean, discreet, easy-going and respectful. I'm a pretty heavy cummer, and I absolutely love giving facials if you're into that.

I have my own place in Nottingham (West Bridgford), so I can host, or I'd he happy to drive a reasonable distance (Derby, Leicester, Sheffield, Northampton, etc.) to make this happen.

If you're reading this and like the sound of it, but aren't sure whether you'd be brave enough to go through with it, you should DEFINITELY contact me.

Seeking a playful, passionate connection

I need to add something extra to my life. I want to feel desired and desire someone back in return. Seeking a connection with a curious and fun female. Let’s send flirty messages and share amazing moments together. I work in Manhattan and live in North Jersey. Hoping to roll onto Spring with some more excitement and spice in my life.

42-year-old married guy here in Miami with an itch for some no-strings-attached fun. She does not know I'm posting this, so discretion is an absolute must.

A little about me: I'm about 5'11" and kinda dad bod I guess, but I've been trying to hit the gym at least a couple times a week. I'm clean, cut, shaved, and most importantly, DDF. I'm easygoing and looking for someone who can keep things light, fun, and completely confidential.

If you're a F looking for the same, send me a DM with a bit about you and perhaps a pic if you're comfortable. Let's see if we click. May be open to a hotwife or couple where the guy watches, but no male on male contact.

Can occasionally host midweek during the day or can travel and open to car and/or semi-public play if the situation is right. Generally prefer around my age or younger but 18+ of course.

​

For some reason it won't let me use Maryland as my location

I could use your help with a little test. I may be getting back together with my ex. We've been having sex and it's good, although I have difficulty cumming. I'm wondering if this is just part of getting old or would a sexy, pretty, young women have a different effect. Would you help an older man figure out if it might be getting close to the time where he needs to throw in the sexual towel.

I’m seeking my captive. You’ll be mine before you understand why.

I’ll admit something up front — there’s a particular kind of story I’ve always been drawn to. The kind of dark, pulpy fiction found in forgotten paperbacks and low-budget films: a sweet, seemingly innocent girl taken by a cold, controlling man who, somewhere between the cruelty and command, reveals a reluctant heart. Misunderstood power dynamics masquerading as romance, where trust is twisted into something strange and intimate. It’s flawed, often problematic, and easy to mock for how ridiculous it is. And yet — I understand the pull.

I don’t want to recreate that story exactly. I want to rewrite it. Intentionally. Consciously. With consent and care built into the bones of it. A dynamic that begins at the end — where ownership comes swiftly, and the emotional bond is something we build in reverse. A dangerous story done safely, with structure and clarity, and the kind of trust that has to be earned and held delicately.

Here’s how it works in my world.

You’ll message. We’ll talk — not for weeks, not even for days, but long enough to know we’re both real, sane, grounded adults with enough chemistry to light the first spark. We’ll establish the language of consent — clear boundaries, safe words, regular check-ins. And then, if we agree, we’ll begin. Quickly. Completely.

You’ll find yourself under new rules. Not suggested — enforced. You’ll be claimed, body and mind. Freedoms, privileges, choices — restructured or removed. Your speech, your service, your rituals — reshaped in my image. You will be made to obey, to defer, to submit in word and action. You will be stripped of performance and taught to kneel in truth. Your identity will be reshaped within the container we build together — not to erase you, but to carve out something deeper and more honest. Something elemental.

And make no mistake — you’ll be used. You’ll be owned. You’ll be shaped through discipline and ritual, through exposure and denial, through control that both unsettles and anchors. You’ll be trained, corrected, watched. But not discarded. Never discarded.

Because here’s what I also promise: I will check in. I will listen. I will hold the weight of what this requires with care. I will give you the tools to grow stronger, even as I strip you down. I will never forget that my first task as a Dominant is to protect, to nurture, and to keep what’s entrusted to me in good condition. You are not a fantasy to me — you are a responsibility. And I take that seriously.

This is a relationship built backwards — but not hollow. If it works, what grows between us will be solid: not just Dominant and submissive, but companions, confidants, collaborators. Through the act of service, we’ll find trust. Through surrender, we’ll find something sacred. Something worth keeping.

I know this concept isn’t for everyone. It demands trust, courage, and the willingness to leap. But if you’ve been waiting for a structure strong enough to hold you, if you long for the sharp thrill of being taken and the quiet peace of being kept — you might find what you’re looking for here.

If you’re the one, you won’t stay free for long.

I’m a very easy going, polite, respectful older male seeking an open minded, sweet, affectionate woman to have a discreet emotional affair with. I am married and don’t want to change that, but we have been sexless for many years and I’m dying inside. I long for intimacy and to give and receive affection.

I understand that having an affair isn’t universally accepted, but I don’t do this without having done a lot of internal soul searching and evaluation first and I’m comfortable with my decision. I also understand that affairs are not easy. I have a very limited time frame to physically meet in person. But with that being said, we can talk daily. Share our thoughts and experiences via email, text, or messenger. And when we are able to meet, it will make it that much more special.

I am in Salem. I work in a professional position. I work from an office 5 days a week. I’m available between 11:30 AM and 1:00 PM most days for a long lunch. I’m in my 60’s but look younger. I’ve been told I’m handsome, I shower daily, and don’t smoke, drink alcohol, or do drugs. I’m 6’ tall, have a stocky build with a dad bod, bald head, gray beard. I’m clean, healthy, and very well endowed. I’m also very liberal and have strong opinions on our current administration.

Ideally I would love to find someone who lives in Salem and could potentially meet at least a couple times a week for lunch, a walk, or just to sit and talk. If you are single and have your own place I will consider myself extremely lucky to have found you. However, I am completely okay if you are in the same situation as me and need an outlet. Like I said, I’m in my 60’s but am not hung up at all regarding age or nationality. As long as you are open minded and can be discreet I will be happy.

Please message me if you would like to talk and see if we click.

Thank you!

I'm married and I have a cheating kink and breeding kink I'm looking to finally make a reality. I'm in a dead bedroom so i have a lot of pent up energy. I'm into younger girls (18+) especially sexy college girls. Let me stuff you with my married cock and fill you up with my married cum. Do you get turned on knowing you're denying my wife of my cum? And that i crave you over her? Do you love just knowing you're getting fucked by a married cock that you shouldn't be? I'm looking for a girl with a very high sex drive and insatiable sexual appetite. Even better if you love cum.

Let’s keep this simple. You have needs. I have needs. I have a good feeling our needs are similar.

I’m looking for a younger (or older) woman that would appreciate the attention of an older man.

I have my own desires and I’d like to find a woman with similar needs.

I’m interested in connecting with a nearby willing younger or older woman.

I’m a laid-back, mature man (74), living south of Boston — grounded, calm, and very aware that real connection is special and worth finding in this crazy world.

I’m not in a rush, and I’m not here to complicate your life. Are you still with me?

What you do with your own time is entirely up to you — but I’m interested in some time with you and I’m more interested in slow burns. But I want to know what excites you.

A real conversation. Growing anticipation. Feeling the connection growing. Letting some tensions build.

My focus is discovering what you’re curious about.

If any of this speaks to something you’ve been quietly hoping for… maybe now’s the time.

Married, single or in a relationship, if you’re reading this far, I like to chat with you…

55yr old professional male from London, looking for a playful chat partner, one who is ideally searching for something longer term, where we can get to know each other. Online to begin with but potential for IRL should things go in that direction.

I'm 5'11", mediterranean look, (think tall, dark & handsome), gym-toned. discreet, educated, respectful & confident.

I mostly work from home at the moment, and so would love to have a naughty distraction ;)

If you are interested, shoot me a message with a short introduction about yourself.

I am a 47 year old man in SF looking for something consistent, fun, and real—good conversation, genuine chemistry, and someone I look forward to seeing.

If you like a man who plans things, follows through, and naturally takes the lead, you’ll probably feel a good fit here.

**About me:**

I’m successful, take care of myself, and have a full life I enjoy. Fit, active, and told I look younger than I am.

Grounded, easygoing, and fun to be around. I like live music, Warriors games, Formula 1, working out, dive bars, and long walks around the city with my dog.

Calm, confident, and intentional. I tend to take the lead in a way that just feels easy.

**What I’m looking for:**

Someone feminine, playful, and easy to talk to. You take care of yourself, enjoy good chemistry, and appreciate a man who leads without overcomplicating things.

Local to SF preferred, but open minded if the connection is there

I’m looking for something consistent and enjoyable with someone I genuinely like spending time with—not just physical, but good conversation and energy too.

Not looking to rush into anthing serious, but open if it naturally builds.

If this sounds like your kind of dynamic, send a message with a bit about you (age, location, physical description, vibe).

Are you that special person for me, loyal, caring, affectionate? I'm looking for a meaningful connection, nothing superficial. Let's talk about our history, present, but also thoughts about the future whether its personal or general. Let's learn from each other, because I feel that with an age gap both can benefit from that.

So, are you:

• 18+
• Living in or close to The Netherlands, or coming to live here soon
• Interested into an older man
• Open-minded
• a non-smoker
• Able to meet

You'll get:

• A 48yo man with plenty of life experience
• Plenty of time even on weekdays to meet
• Someone a bit shy at times, but can be quite talkative with the right person

There's plenty of things to do together. Keep in mind that the intention is to meet, so we could:

• Talk about anything and everything
• Visit the theatre, attend a concert, go to the movies
• Listen to vinyl records
• Watch movies at home
• Go out for walks
• Go visiting different places, cities
• Have a day on a boat
• Visit thrift shops
• And more of course!

This is initially meant for a SFW friendship, but depending on both our feelings and consent this could eventually evolve into having intimate moments too.

One thing is important though and I know this is not for everyone: I'm married and have a child. Actually my wife endorses and even encourages me to post on Reddit. Feel free to ask about this.

PS. Here are some more interests and activities to do together in emoji form 😄

🐈 🌳 🛥️ 🛤️ 🚗 🌅 🏞️ 🎵 🥾 🎹 🎞️ ⌨️ 📖 💠 🥴🌀✨ 🚶‍♂️ 🌌 📀 [◉°] 🏰 🏙️

Let me introduce myself, I'm 32 years old, located in the eastern timezone. I have about 10 years of experience being a dominant both in person as well as online. I'm smart, well read, educated, career driven and athletic as well, perhaps I can be described as an athletic nerd with a slight dad bod.

What I am looking for is a submissive that is eager to serve and eager to learn, ideally this would be online via the usual messaging apps. Age, location and looks are unimportant as long as you are over the age of 18. Experience isn't an issue either as I have experience showing the ropes to beginners as well as working with ladies with much more experience. I'd like to communicate daily, but I am a fairly busy man with a full time career.

As a dom I am strict but caring, selfish yet considerate. Nothing turns me on more than a submissive who gets pleasure from fulfilling my needs. I have various kinks that include, but not limited to: free use, control, obedience, bondage, spanking, choking, anal play, orgasm control/denial, pussy play, pussy stretching, watersports etc.

I am not a fan of major degradation or humiliation, I like to cherish my sub and encourage her when she fulfils the tasks I ask from her. Other kinks and interests can be discussed as well and limits will certainly be respected.

6ft tall, 240lbs, single, drug/disease free, don't smoke, drink on occasion, no children Dominant black male looking for a single submissive woman with a nice rack (C cups or bigger) and a sense of humor to mold into my image of the perfect submissive or deeper for a long term relationship. So if that's you then reply back so we can talk.

I love a woman that's intelligent, ambitious and knows fully well they can live and survive without a man but still has a deep need to be submissive to one

Be between the ages of 24-34

Single women only   Have a sense of humor   be drug free, disease free and have no kids

Reply by telling me your cup size and sending a pic. (Whether it's shirt cleavage,bra or bare, i'll leave that up to you)

I’m looking for a younger woman who fantasizes about being with an experienced older man. Maybe you just want an older man to guide you sexually. Maybe you get off on giving a married man what he doesn't get at home. Maybe you just want to be used like a sex toy. Regardless of your reason, we can make it happen. I’m open to any and all. Whatever your race, age, or size, you should hit me up to at least chat. You don't know if you don't try. Trust me when I say, I absolutely want you if you're reading this.

I'm attractive, in decent shape, recently tested(as of last month), and ready to make this happen asap. I look forward to hearing from you.