Winter Park FL
Age 18-100

Sponsored

Log in to enable the Gallery view Login

Log in to use the Filtering feature Login

Straight Men for Gay Encounters in Winter Park FL – Real Ads — Page 3

Hey! Please review DL:

Mar 13, 2026

Hook up with an Older Man Tonight! Sponsored

Sissy in chastity to serve - femdom or couple (Colonial) 54

Mar 12, 2026

I find trans women incredibly hot! (Winter Park) 43

Mar 09, 2026

Looking for now (first time) off main lane (Ridley at main) 24

Mar 07, 2026

Classy ts woman ready for di** (Orlando) 29

Mar 04, 2026

New here so please pick me lol (fashion square mall area) 43

Mar 03, 2026

Nice guy looking for ongoing (Winter park) 59 Verified

Mar 02, 2026

Bored and by the winter park area (by winter park) 24

Feb 28, 2026

Classy ts woman ready for di** (Orlando) 30

Feb 23, 2026

Seeking cd for discreet fun (Orlando) 48 Verified Premium

Looking for cd ts fem downtown (Downtown) 27

Down for fun (neighborhood trans) 25

Feb 22, 2026

Looking for a mutual oral fwb (Orlando area) 33

Let's connect now (Nearby) 27

Feb 18, 2026

Looking for a passable cd that can host now. (Avalon Park) 38

Feb 17, 2026

Classy ts woman ready for di** (Orlando) 30

Feb 16, 2026

Young fit top looking for sissy cd host (Downtown) 28

Let’s have fun (neighborhood trans) 28

Feb 15, 2026

I'm looking to have some nsa fun (Casselberry) 42

Feb 11, 2026

Looking for str8 curious guys (Rio Pinar) 36

Sexy ts looking for fun (Conley St) 25

Blue collar, linemen, construction, country guys low-key, discreet relief (Orlando / Maitland) 36 Verified Premium

Gl black straight iso cd or trans (Universal) 35

Feb 10, 2026

Fwb daytime fun with trans woman. (Altamonte springs) 38

Feb 08, 2026

Classy ts woman ready for di** (orlando) 30

Feb 06, 2026

Blue collar , country, linemen, construction workers!and rednecks - hmu for discreet relief (Orlando / Maitland) 36 Verified Premium

Feb 05, 2026

Just here for fun (Orlando) 28

Classy ts woman ready for di** (Orlando) 28

Feb 01, 2026

Blue collar, country, linemen, construction workers!and rednecks all the front ! discreet relief (/ Maitland) 36 Verified Premium

Jan 17, 2026

Straight for fem (Winter Springs) 35

Young tall handsome college guy looking (Winter Park) 21

Jan 16, 2026

Ts looking for fun (neighborhood trans) 28

Jan 04, 2026

Searching for a fem or ts (Oviedo) 19 Verified Premium

Jan 01, 2026

I’m trans lady available for fun (South) 25

Bbc in need of a big booty chubby bottom (Woodsprings Hotel near Rosemont) 28

Dec 29, 2025

Sexy ts or cd ? (Dr Phillips) 35

Chair & sheet fun (Dr phillips) 33

Dec 28, 2025

Str8 curious looking for a dominant top (Northdale) 50 Verified

Dec 23, 2025

Looking for versatile (Orlando) 64

Dec 22, 2025

24 m no strings attached (Altamonte springs) 24

Dec 15, 2025

Lf smooth cd or trans (Winter Park) 40

Dec 11, 2025

Looking for one time usage (Baldwin park) 26

Dec 04, 2025

I need to be released (East orlando) 39

Dec 01, 2025

Looking to get bred (Kissimmee) 45

Nov 29, 2025

Tonight let’s see (Conway) 28

Nov 19, 2025

Masc dl discreet btm jock here (orlando) 34

Nov 18, 2025

W available for guys (downtown) 26

Nov 09, 2025

Bbc to play with asap (Orlando) 29

Nov 05, 2025

Hey looking for clean hung (Airport) 25

Oct 21, 2025

I am woman — sweet mischief in motion (Orlando) 26

Oct 20, 2025

Let’s have fun (Nearby) 28

Oct 19, 2025

Ex d1 football player hosting straight/married men this morning at ac downtown (Downtown) 42 Verified

Oct 17, 2025

Looking for a discreet mature serious daddies to meet to play (Dr) 26

Oct 16, 2025

Looking for a trans girlfriend (Orlando) 30

Very new to this (Altamonte Springs) 31

Latino looking for fwb cd/trans (Casselberry) 63

Oct 11, 2025

Gh or cd reply (Colonial) 25

8 inch thick wide uncut downtown for ts (Downtown) 45 Verified

Women for guys (downtown) 26

Oct 10, 2025

Woman for guys (downtown) 26

Woman available for guys its weekend shoot me (downtown) 26

Oct 09, 2025

Looking for fun & connection - sensual trans woman available (Orlando) 30

Oct 08, 2025

Blk male looking for chub bottoms (Narcoossee) 35

Oct 06, 2025

First time (winter springs) 35

Oct 04, 2025

Trans Girls Looking to Hook Up - Register & Browse Profiles Sponsored

Looking for jo friend (Union Park) 37 Verified

Sep 30, 2025

I am ready and available for sexual encounters, your sexual fantasies are my hobbies. (Orlando) 28

Sep 26, 2025

Looking for fem type cd/ts (Casselberry/Winter park/Wintersprings & longwood) 46

Sep 25, 2025

Come show me your skills (Orlando) 32

Hosting in my hotel for cd femboys trans (INTERNATIONAL DR) 30 Verified Premium

Sep 24, 2025

Private discreet glory h o l e for straight bi men (Orlando Orlando) 18 Verified Premium

MCOGloryhole

Sep 23, 2025

Private discreet glory h o l e for straight bi men (Orlando Orlando Orlando) 18 Verified Premium

MCOGloryhole

Seeking fem type /cd/ casselberry and nearby (Casselberry /Altamonte/Maitland/Longwood/) 46

Sep 22, 2025

02/17 35 straight male top looking for ts (Orlando) 35

Sep 19, 2025

Where's daddy (Three one six nine zero zero five zero nine six) 20

Sep 09, 2025

I can host or travel (Near universal studios) 30

Sep 08, 2025

Looking for a sexy cd or ts (Winter park) 30

Sep 06, 2025

Let’s relax? (Orlando) 32

Aug 27, 2025

Top looking for trans or cd bottom (Narcoossee) 40

Gh open! east side (East Orlando) 32

Aug 25, 2025

Looking for a beautiful sexy passable tranny that likes to party (South Orlando) 50

Looking for a party partner for a few hours man or woman or bith (Oakridge) 54

Aug 23, 2025

Let’s have fun (Nearby) 28

Female for guys (downtown) 26

Aug 21, 2025

Cd looking for hot str8 guy for fun and chill (Sexy Cd hosting looking for sexy guys) 29 Verified

Aug 20, 2025

Iso/fem type (Casselberry /winter park/altamonte) 45

Aug 18, 2025

Straight lookin to nut (Metro) 25

Aug 17, 2025

Available for first time meet up (Orlando) 30

Consistent gh to use (Altamonte springs) 28

Aug 16, 2025

Looking for fem type cd/ts (Casselberry) 46

Aug 14, 2025

Trans looking for (Orlando) 26

Aug 12, 2025

Mwm looking for cd/ts (Altamonte Springs) 50

Aug 11, 2025

Top looking (Millenia) 18

Aug 08, 2025

Trans here (Orlando) 32

Aug 02, 2025

Hot curvy lady looking to meet (Orlando) 28

Aug 01, 2025

Sexy cd and her cuckold seek bbc (Orlando) 37

Jul 26, 2025

Cool, fun, smart and classy (Brevard) 31

Jul 24, 2025

Looking for tranny fun (Orlando) 28

Jul 22, 2025

Downtown orlando (Downtown orlando) 41

Jul 21, 2025

Would like to be seduced by a sissy (Altamonte) 31

Jul 18, 2025

Bear looking for twink, cd or fem (Casselberry) 55

Willingly to explore more kinks (Central Business District) 33

Don't see what you're looking for?
Post here