Winston-Salem Trans and Crossdressers Classifieds
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June 4th, 2025
Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Winston-Salem Area
Hi, my fem name is Gloria. I'm a married crossdresser in the Winston-Salem area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but wife doesn't approve. I really need to let my fem side out to play!
I'm seeking cross...
TS m/f switch 28 new here TS m/f Switch in Winston-Salem
Sandi wants to meet hot guy for fun and hot sex. Age 28, nice build, 7.5". Non op functional. Love oral sex, anal sex and kinks of all sorts. View my profile and message me here @SandiSwitchTS...
Selena Trans girl cute looking for love Hello boys. I am looking for love. You want meet me? I want meet you too. See my pictures and send message for date....
I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Winston-Salem ) Sexy Crossdresser Elissa Looking for Hot Fun in Winston-Salem๐
Do you like knowing I'm a man in womens clothes.. do I look sexy?? - VEW MY CD PICTURES
Are you wanting to satisfy your innermost desires with a sexy shemale such as myself? My name is Elissa and I ...
Superior Massage by gorgeous T-Girl T-Girl for Dating in Winston-Salem
I will help you unwind and create a cozy environment for you! I am 36DD, 7" and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl
Gayle <3
Transgender World Profile
Username: Ga...
Hi Guys!! I am looking for someone fun! This is Lara and I am 41 and transitioned when I was 24. I pass exceptionally well and you will be surprised at my hidden skills. Call me! ...
TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Winston-Salem
Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Winston-Salem
I'm queen Delilah a trans woman here in Winston-Salem searching for her king. You'll get the royal treatment when you're with me honey! Just grab hold of my magic scepter and his majesty can have anything he desires. Imagine the intrigue and scandal...
Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Winston-Salem
Beautiful Brandi. If you're attracted to the female form then you will want to message me @ BrandiTS27. I'm pre-op, tall, slim and beautiful with 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your...
Do you know the difference between a dick and a bucket of popcorn? You don't know? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Winston-Salem tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longe...
Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Winston-Salem area and want to make some new friends! I am a masseur, hot body and hung. If you want to get together, Send me a private message Crystal27trans <3 ...
Having fun and Staying Young Young trans fem looking for nice date with lady. I am kind and thoughtful and you will have a very good evening if I take you out. Let me know what you want to do or where you want to go. View profile and message me
xoxo, Sherry....
SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Winston-Salem Secret Crossdressing Hookups in Winston-Salem
Hey there. I'm Sam (Samantha when dressed up). If you're reading this ad you may be a crossdresser who needs to let your feminine side out to play. Me too! If you're in the closet or married, it's no problem. I live alone, have a nice, home with a priva...
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Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Winston-Salem
Look no further honey, I'm Franny an Ebony trans woman here in Winston-Salem to fulfill your wildest fantasies. Dreams really do come true when you are with Fabulous Franny. I'm all about the frills and the thrills baby! We can freak it and they do...
Winston, NC๐TRANSGENDER Sexy Transgender Lady Wantingsex in Raleigh, North Carolina! ๐
WINSTON-SALEM, NC - Trans Messanger
I'm a Transgender lady living in Winston -Salem, North Carolina. I was born a male..however I always known I am a pretty girl.I love meeting for sex in North Carolina
Winston - Sa...
Email Local Shemales Now! ๐ Want to Hookup and Find Local Shemales? RADE PIX - MESSAGE - BROWSE PROFILES
This Website Helps you find local shemales and TGirls meet local men. It's the perfect place to find what you'reinterested in ๐.. Do you want to meet local shemales who want to fuck and have some sex...
Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Winston-Salem
Hey! Thanks for looking at my ad. This is the first time I've done this so bear with me plz. I am Jared, FtM trans man. I transitioned at age 25 and I just turned 30. Come and meet me! Check my personal profile @FtMJared29 and say ...
Flirty & Feminine CD Ready for Some Fun ๐๐ I’m a sexy, smooth, and playful crossdresser who enjoys the attention, desiring to be treated like a lady. Seeking for a man who can appreciate a well dressed CD for a casual fun night or even something ongoing. I am a pleaser and I want to be pleased. ๐
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I Need a STEAM ROLLER Baby!!! I want you to inject my soul with that sweet lover's pole till there ain't much of me left behind. I'm your whore so just F my brains out tonight. I'm a naughty trans looking for a top big boy to have his way with me. So it's heels and ass up and earth moving sex the hard way. That's the way I like ...
Superb Shemale in Winston-Salem... T-Girl for NSA Encounters in Winston-Salem
When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Winston-Salem. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondl...
F/M seeking love and fun Female to Male Trans Man in Winston-Salem
My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and other times I let ...June 3rd, 2025
Your Flirty CD Sweetheart Awaits ๐๐ Winston-Salem I am a hot, cool and confident crossdresser who enjoys the feeling of being wanted, loved and taken care of like a lady. Whether you are looking for some hot action, a nice relationship or even a friend with benefits, I am here to make it unforgettable. ๐ ๐ Feminine, fun and ...
Penny for your thoughts? Penny TS in Winston-Salem
Hey, I am Penny! I am recently new here and I am non op switch with a pretty nice pair, both top and bottom! Send me a message online!!
I'm looking for a nice man who will enjoy being with me. Let's enjoy hot dates and explore sexuality together. If that sounds interestin...
I'm the Girl Mother Never Warned You About!... But then, how could your mother have known? I'm Dirty Diana corrupting good decent honest men like yourself here in Winston-Salem for many moons. I got a big secret and it's show and tell time baby! It's easier to show you than to tell you. I'm fully functional and passible. I need a sexy man who li...
Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Winston-Salem?
Hey, I am Jasmin, 8" with a great body and busty. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for hot dates and see where it goes!
Hit me up @SweetJasminT...
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Iโm a Sexy and Naughty T-Girl Here in Winston-Salem. Winston-Salem T-Girl 4 NSA
Fabulous Fanny here boys! I'm a trans woman living in the Winston-Salem area. Sweet, sexy, friendly and outgoing. I will definitely make you feel happy/sexy vibes and relaxed. I have an amazing body boys. I'm a pretty t-girl with a big present! So forget all your wo...
Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Winston-Salem boos out there. I'm a sexy trans woman currently living in large and lovin' every second of it. Hit me up cause I Wanna ROCK too! I'll show you what a real woman can do and everything you don't know now. I...
Transgender๐ขTINA TS๐๐ Ready to play with a TGirl Tonight?
Hi babe, I'm Tina ๐ I'm in Winston-Salem and ready to meeup and hookup in LA tonight.. Let's hang out and have some super sexy fun!! I really need to get out and have some fun. Come check out MY PROFILE, browse my pix, videos and send me a message no...
Winston-Salem's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Winston-Salem
Hi you sexy man! I'm Toni a trans woman from here in Winston-Salem. Looking forward to a fun, sexy evening with you tonight. Let's make some memories that we'll never forget! I'm a 28 year old redhead tgirl who's passionate, warm, funny, hung, function...
Sexy hung and big busted Hung and Busty Shemale in Winston-Salem
Tammy, 39, 38DD, 9" and so cute!! What more could you want in a gurl?!! How about you message me @Tammy38DD and we can talk and meet! Send your recent pic for mine....
I Need a Sexy Man to Tame Wild Willy! Hung Winston-Salem Trans Woman
Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Winston-Salem with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbuck...
New Body New Me M2F post-op in Winston-Salem
Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head with slender legs and curvy body. Want to come and join me for a drink? I love sex in my new gender!!! Seeking a local area man who will enjoy sex and passion with me. Message me online N...
M-F trans woman wants a date I want someone understanding and kind. Please check out my profile and rate me. I am 36, 5 feet 6 and elegant! My name is Lyssa....
Flawlessly gorgeous trans bombshell in Winston-Salem Trans MtF for Man in Winston-Salem
I transitioned 6 years ago at the age of 18. I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am 5 feet 7 and have deep blue eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned!
Send ...
Dr Freakin'furter - Mine's Bigger Than Yours! White T-girl here and I'd bet mine is bigger than yours. We'll just let it be our little intimate surprise when the time comes. No one needs to know our business, Let's just keep it discreet. If you live in the Winston-Salem area come see if you measure up! Click here for explicit photos. ...
I'm a Horny Shemale ๐๐ Looking For Sex Tonight!! Sexy Shemale๐ Ready to Rock Your World!
Local Transsexual - TGIRL Sext App ๐ฒ
I'm a Transgender and I'm looking for a naughty man with a nice cock here in near me.. Who is wanting to share some sexy fun with me. I've been really horny and hard!! I love taking cock and giving it, what are...
Sassy CD Looking for a Real Man ๐๐ฅ A sweet, sexy and a little naughty crossdresser here, I like to play and flirt, and I need a strong man who knows what he wants. I enjoy the process of dressing up, teasing and bringing fantasies to life. If you are into sensual encounters and passionate fun then let me and y...
Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Winston-Salem who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all i...
INTERACTIVE MAP: Transexual Tracker in the Winston-Salem Area! Local Transexual Hookups
Meet local transexuals in the Winston-Salem area. View our interactive map below to meet local trans hookup members who are seeking dating or sex hook ups. Click any thumbnail below to begin your search.
Interactive Winston-Salem Trans Hookups Map
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Tainted Love - Beyond Compare! Kinky Trans Woman in Winston-Salem
Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Winston-Salem. What kind of kink? You'll have to contact me to find out. I'm open to all sorts of fetish play if you are. I need a hookup with an open minded man. The sort of man who appre...
Partners in crime, or? Sexy, Slytherin, Aries, ISTP and more, if that gives you a hint about my personality traits. So, I’m a sexy, sensual, tender, animal loving, bookworm. I am a bit of a flirty whore, who loves mystical magical movies and stories, so let’s get that out in the open. If you live in the W...
Don't Worry I Bite! Feisty redhead trans in Winston-Salem full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to con...
A monster in the sheets, but a lady in the streets... Hello men, I'm Lilith a 27 year old sexy femme, fully functional, passible, sexy and hot to trot trans. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Winston-Salem area and are interested then drop me a line and introduce yourself. Yo...
HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Winston-Salem! LET'S TAKE CARE OF THAT TRANNY FANTASY!
"Experience your secret tranny desires in real life!"
Hot shemale Gia wants to hook up with you in Winston-Salem! No strings - just great times, so join my page free for instant access!
Shemale Gia's Winston-Salem Sexbook @ShemaleGia27
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British T-girl Seeking Classy Gentleman in Winston-Salem... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Winston-Salem and am financially independent and looking for a gentleman who is like-minded, equally solvent and has ...
Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Winston-Salem AREA
Hi baby! I am waiting to meet you. I can host or travel to you. Down to earth preop transexual woman seeking an understanding man who can appreciate my uniqueness. I am a great cook and great fun! Let your hair down and allow me to pamper you! Private Me...
Trans Playmate Sex Kitten... Ebony trans woman in Winston-Salem wants to be your sex kitten and playmate so let's make a playdate! I love all men so any race or body type or political side is fine with me. I can get along with anyone and we're gonna have a great time. I do all men, gay, bisexual, bicurious, swingers and groups....
Local Crossdresser ๐๐ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Winston-Salem
View My Personal Pix - ๐คซ A sexy Crossdresser from Winston-Salem, here, and her name is KaralynnCD. I am pre-op but that has not stopped me from enjoying all the benefits that come with being a Crossdressing Trans woman. If you like d...