54 [M4A] Clearwater Masculine Daddy needs his first bottoming experience!

54 [M4A] Clearwater Masculine Daddy needs his first bottoming experience!

Let's try this again. Only this time I'll be more specific about what I'm looking for. It may be a pipe dream but here goes...

First about me... I'm a professional, tall, handsome and masculine guy. I'm not a hairless twink. I'm DDF and expect you to be. I'm usually the dominant type in most situations but I'm really wanting to bottom for the first time so I'm willing to be submissive. I have some experience with guys but mostly mutual oral and I've topped once. I've been playing with toys for years so I can't take a pretty good size cock.

What I'm looking for is a clean, good looking, at least HWP or fit guy that takes care of himself. I'm also totally open to a MF couple with bi male. No drugs or smokers need apply. I'd prefer someone with at least 6" and preferably more. I'm not one to sleep around and my health is very important to me to safe play is a must. Ideally I'd like to find one guy for regular play that's on the DL like me. I know this is a lot to ask but it's what I'm looking for and hopefully will resonate with the right guy.

If this sound like you please DM me. I'm happy to chat and share pics after we verify.

u/pegmepleez11 — 2 days ago
▲ 25 r/StPeteFL_GW+6 crossposts

49 [M4A] Clearwater Handsome and Fit Daddy Seeking Hung Top

Hi 49 yo WM here. I'm good looking, hwp, DDF. I'm looking to have some fun with a Hung guy or Trans woman to show me what it's like to bottom. Want to be the first to stretch me out? You don't have to be a hard body but I do prefer hwp. Hmu with something about you and your experience. I'm also open to couples.

u/pegmepleez11 — 6 days ago

49[M4F] Handsome and Orally Fixated Looking to Eat Your Pussy..No Reciprocation Necessary

Hi. I'm a good looking professional gentleman. I'm tall, handsome and fit. I'm looking for a woman that needs her pussy eaten by a man that thoroughly enjoys giving pleasure. No reciprocation needed, seeing you cum over and over again is enough for me. I'm local to north Pinellas but will travel for the right woman. DM's open so send me a message and say hi.

u/pegmepleez11 — 10 days ago

M4F Handsome Orally Fixated Man Looking to Eat Your Pussy.. No Reciprocation Necessary

Hi. I'm a good looking older professional gentleman. I'm tall, handsome and fit. I'm looking for a woman that needs her pussy eaten by a man that thoroughly enjoys giving pleasure. No reciprocation needed, seeing you cum over and over again is enough for me. I'm local to north Pinellas but will travel for the right woman. DM's open so send me a message and say hi.

reddit.com
u/pegmepleez11 — 10 days ago

M4F Orally Fixated Handsome Gentleman Looking to Eat Your Pussy Today..No Reciprocation Necessary

Hi. I'm a good looking older professional gentleman. I'm tall, handsome and fit. I'm looking for a woman that needs her pussy eaten by a man that thoroughly enjoys giving pleasure. No reciprocation needed, seeing you cum over and over again is enough for me. I'm local to north Pinellas but will travel for the right woman. DM's open so send me a message and say hi.

reddit.com
u/pegmepleez11 — 10 days ago

Orally fixated handsome guy looking to eat some pussy today..

Hi. I'm a good looking older professional gentleman. I'm tall, handsome and fit. I'm looking for a woman that needs her pussy eaten by a man that thoroughly enjoys giving pleasure. No reciprocation needed, seeing you cum over and over again is enough for me. I'm local to north Pinellas but will travel for the right woman. DM's open so send me a message and say hi.

reddit.com
u/pegmepleez11 — 10 days ago
▲ 8 r/Florida_FWB2+4 crossposts

Looking for a Woman into Pegging and assplay...

Hi. I'm a professional, handsome and fit gentleman looking for a woman who’s into pegging or curious to explore it with someone experienced and easygoing. I care more about chemistry and communication than anything else — happy to talk logistics, boundaries, whatever you need to feel comfortable. Located in Clearwater, open to chatting first before anything else. DM's are open so please say hi.

u/pegmepleez11 — 12 days ago

M4MF Handsome Bi Guy Seeking Couple

Hi. I'm a quite tall, handsome and fit man in his early 50's searching for a like minded couple to play with on a regular basis. I'm in northern pinellas but can travel within a reasonable distance. I work out and take care of myself. I'm a masculine man with body hair so if you're into the smooth hairless type I'm not your guy. I'm not perfect though and I don't expect you to be.

I guess I'm what you'd call heteroflexible in that I love women but also like to play with men. I enjoy giving and receiving head and have topped before. I'd also like to try bottoming. I'm around average where it counts but never had any complaints and am a very giving and skilled lover. I tend to be more on the dominant side but can also be submissive. I do require discretion and will respect yours as well. I'm happy to share pictures once we verify as I know mutual attraction is important. I don't sleep around and my health is very important to me. So I'm really looking for something ongoing rather than a one time thing.

If I've peaked your interest please send a DM and tell me about you, what you're into and what you're looking for. I look forward to hearing from you!

reddit.com
u/pegmepleez11 — 20 days ago

6'4" Tall but only 6.5"x4.5" Thoughts?

I feel like it's so small on my frame. What I wouldn't give for another inch of girth!

u/pegmepleez11 — 23 days ago

Mature, Handsome and Respectful man looking for Bi couple

Hi. I'm looking for a bi couple to play with on a regular basis. I'm not into bed hopping as my health and discretion are important to me. I'm a talented lover and very giving. I enjoy both women and men and have a strong appetite for sex. I'm around average down below but have never had any complaints. Shoot me a message if you're interested and let's chat.

u/pegmepleez11 — 26 days ago

M4M Any Hung Tops want to be a married Masc Daddy's first?

I'm a good looking and fit older daddy that's looking for an experienced top to be the first to top me. I've topped myself but yet to be topped. I'm 54 but look much younger and am fairly fit and muscular. I'm masculine and have body hair. I'd prefer someone younger than me no older than 40. Must be DDF and be willing to play safe. Condoms a must. DM me if you're interested with a little about yourself and your experience.

reddit.com
u/pegmepleez11 — 1 month ago

Any Ladies into Pegging?

Not new to this, know what I like and how to communicate about it. Looking for a woman who’s already into pegging or curious to explore it with someone experienced and easygoing. I care more about chemistry and communication than anything else — happy to talk logistics, boundaries, whatever you need to feel comfortable. Located in Clearwater, open to chatting first before anything else.

reddit.com
u/pegmepleez11 — 1 month ago

49 M4F Any Ladies into Pegging?

Not new to this, know what I like and how to communicate about it. Looking for a woman who’s already into pegging or curious to explore it with someone experienced and easygoing. I care more about chemistry and communication than anything else — happy to talk logistics, boundaries, whatever you need to feel comfortable. Located in Clearwater, open to chatting first before anything else.

reddit.com
u/pegmepleez11 — 1 month ago

49 M4F Any ladies into Pegging? Clearwater

Not new to this, know what I like and how to communicate about it. Looking for a woman who’s already into pegging or curious to explore it with someone experienced and easygoing. I care more about chemistry and communication than anything else — happy to talk logistics, boundaries, whatever you need to feel comfortable. Located in Clearwater, open to chatting first before anything else.

reddit.com
u/pegmepleez11 — 1 month ago

Any Ladies into Pegging?

Not new to this, know what I like and how to communicate about it. Looking for a woman who’s already into pegging or curious to explore it with someone experienced and easygoing. I care more about chemistry and communication than anything else — happy to talk logistics, boundaries, whatever you need to feel comfortable. Located in Clearwater, open to chatting first before anything else.

reddit.com
u/pegmepleez11 — 1 month ago

Any ladies into pegging?

Not new to this, know what I like and how to communicate about it. Looking for a woman who’s already into pegging or curious to explore it with someone experienced and easygoing. I care more about chemistry and communication than anything else — happy to talk logistics, boundaries, whatever you need to feel comfortable. Located in Clearwater, open to chatting first before anything else.

reddit.com
u/pegmepleez11 — 1 month ago

49 (M4FM) Handsome, fit, bi masculine daddy looking for couple to play with

I'm a handsome, tall, fit, masculine daddy looking for a fwb couple. Something ongoing is ideal. I'm a chill guy and love to please. I'm average where it counts but never had any complaints. Not into drugs or smokers. Must be clean and discreet. Hmu if you're interested and want to see if we're a good fit.

reddit.com
u/pegmepleez11 — 2 months ago

52 MFS Handsome, Masculine, Fit Daddy seeking sissy #Pinellas #Hillsborough

I'm a handsome, tall, fit, masculine daddy looking for a hung younger attractive sissy, either single or a couple. Something ongoing is ideal. Not into drugs or smokers. Must be clean and discreet. Hmu if you're interested and want to see if we're a good fit.

reddit.com
u/pegmepleez11 — 2 months ago

52wm M4M M4MF Handsome bi man for Hung guy or couple

I'm a handsome, tall, fit, masculine daddy looking for a Hung guy, either single or a couple. Something ongoing is ideal. Not into drugs or smokers. Must be clean and discreet. Hmu if you're interested and want to see if we're a good fit.

reddit.com
u/pegmepleez11 — 2 months ago