Winston-Salem Transgender Sex Ads

Browse Winston-Salem transgender sex ads to meet local transexuals, crossdressers and shemales for sex, dating or friendship. It's free to search the trans sex classifieds, or post your own adult ad!

Home / Alternative Sex Ads / Transgender Sex Ads

Show Ads In: Asheville | Boone | Charlotte | Eastern NC | Fayetteville | Greensboro | Hickory / Lenoir | Outer Banks | Raleigh / Durham / CH | Wilmington | Winston-Salem

  • August 23rd, 2025
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Winston-Salem Looking for someone a little different from the average guy? Hey, I'm Barry, age 31, fit and healthy. I have a square jaw, sparkling eyes and short dark hair. I like to dress sharp. I am currently looking for a fun lady to spend time with. Possible longterm relations...
  • Raunchy Shemale in Winston-Salem Ready to PlayRaunchy Shemale in Winston-Salem Ready to Play I love getting down and dirty with a man who knows how to handle a shemale like me. My name is Diana, and I'm looking for a local guy who can keep up with my insatiable appetite for all things naughty. Whether you're into top or bottom fun, blowjobs, ass play, or just want to ride my tight shemal...
  • FtM seeking Princess Bride in Winston-SalemFtM seeking Princess Bride in Winston-Salem FtM seeking Woman in Winston-Salem Hi, I'm Andy, age 33, FtM transgender man living in Winston-Salem. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message&nbs...
  • Hot Shemale in Winston-Salem Looking to Play and FuckHot Shemale in Winston-Salem Looking to Play and Fuck I'm a sexy shemale named Chris who loves to have some naughty fun with local men. I'm looking for a guy who can handle all the kinky things I have in mind. I enjoy being both a top and bottom, so we can switch things up and see where the night takes us. I love giving blowjobs, getting my tight ass...
  • Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖 Preop Trans in Winston-Salem Hi! I'm Brandi, new TS in the Winston-Salem area. I'm MtF preop transexual woman. I pass as female very well so we can go to your business function or out for dinner followed by a night of forbidden fun that only we will know about! I am fully functional, 8" thick hidin...
  • TS Asian lady ready for upscale action (28)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...
  • 27 y/o Sexy Hung Crossdresser in Winston-Salem27 y/o Sexy Hung Crossdresser in Winston-Salem Hung Crossdresser for Male in Winston-Salem Hey, I go by Selena when I'm cross dressed. I love being feminine and servicing my man!, I'm age 27, well hung and so cute when I'm dressed up!! What more could you want in a gurl?!! View my pics and message me @Selena27femCD so we can talk and meet for a...
  • Sparkle with me under the North Carolina moon 🌙Sparkle with me under the North Carolina moon 🌙 Hey there! I'm Lesya, a transgender beauty from Winston-Salem looking for someone special to share some magical moments with. 💫 I love exploring new places around town like Bailey Park, Old Salem Museums & Gardens, and grabbing a bite to eat at Mozelle's Fresh Southern Bistro. 🌳🍽️ Bei...
  • Naughty Shemale Seeking Local Man for Wild FunNaughty Shemale Seeking Local Man for Wild Fun Hey guys, I'm Krissy, a hot and horny shemale from Winston-Salem looking for a man who can handle my insatiable appetite for pleasure. I love to suck cock, ride dick, and make you explode with pleasure. Whether you're into getting your ass pounded, giving or receiving a sloppy blowjob, or just want ...
  • INTERACTIVE MAP: Transexual Tracker in the Winston-Salem Area!INTERACTIVE MAP: Transexual Tracker in the Winston-Salem Area! Local Trans Hookups Interactive Mapping Meet Local transexuals in the Winston-Salem area for friendship or sex hookups. View member thumbnails on the interactive map below to meet local members who want to meet local transexuals or admirers. Click any member photo below to get started. Sign up free...
  • Shemale Nightclubs Near You in Winston-Salem, North CarolinaShemale Nightclubs Near You in Winston-Salem, North Carolina Shemale Nightclubs Near You in Winston-Salem, North Carolina Shemale Clubs Near You in Winston-Salem, North Carolina is a directory of trans-friendly nightclubs and bars. LGBTQ+ clubs come and go. We strive to keep this transgender clubs directory complete and rely on your input to help us do so....
  • F/M seeking love and funF/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 ...
  • Jasmin T-girl Ready to make friendsJasmin 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...
  • Gorgeous, Passable Trans in Winston-Salem 😍Gorgeous, Passable Trans in Winston-Salem 😍 Gorgeous Passable Trans MtF for Man in Winston-Salem 😍 I transitioned 6 years ago at age 18. I am pretty, with long light brown hair, a nice figure and long shapely legs. I have brown puppy dog eyes and kissable lips. Check my profile @TransFaye24 for pics and prepare to be stunned!  ...
  • August 22nd, 2025
  • Superior Massage by gorgeous T-GirlSuperior 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...
  • Meet North Carolina Transexuals Online: Live Chat, Member Profiles, Photo Swaps & Local Trans ClubsMeet North Carolina Transexuals Online: Live Chat, Member Profiles, Photo Swaps & Local Trans Clubs Meet North Carolina Transexuals Online!  Meet North Carolina transexuals online at AmericanTransexuals.com. Our web development team includes transexual women and male trans admirers, so we have a unique understanding of transgender attraction. We have created an online community where you can...
  • Local Shemale Looking for Hot Fun in Winston-SalemLocal Shemale Looking for Hot Fun in Winston-Salem I love to get down and dirty with a man who knows how to handle a sexy shemale like me. My name is Marjory, and I'm looking for someone local who can satisfy all my desires. When it comes to sex, I'm into everything naughty and taboo. I love giving blowjobs, getting my tight ass pounded, and feel...
  • Erotic Temptation: Seeking a ConnectionErotic Temptation: Seeking a Connection Hey there, I'm Deni from Winston-Salem, North Carolina. I'm a curvy transgender woman of Hispanic descent who loves embracing my LGBTQ identity. You can check out my pics at my personal profile page @deniwi56078. I'm looking for someone who enjoys exploring local spots like Krankies Coffee or Old...
  • Spark the Flame: Transgender Beauty in Winston-SalemSpark the Flame: Transgender Beauty in Winston-Salem Hey there! I'm Dorette, a proud transgender woman from Winston-Salem, North Carolina. I may not fit society's standards of beauty, but my confidence shines through in every step I take. Being part of the LGBTQ community has taught me to embrace my true self and live authentically. I love explorin...
  • Elegant Transgender Beauty Seeking ConnectionElegant Transgender Beauty Seeking Connection Hey there, I'm Caresa from Winston-Salem, North Carolina. I may not fit the mold of traditional beauty, but my unique body type and ethnicity make me stand out in a crowd. I embrace my transgender identity and love being a part of the LGBTQ community because it allows me to be my authentic self wi...
  • HMU for Sex in Winston-SalemHMU for Sex in Winston-Salem Newly Single and Ready to Mingle in Winston-Salem Hi guys, my name is Barbie, age 28. My husband cheated for the last time. Now it's my time to have some fun! If you want to hook up for passion and hot sex in the Winston-Salem, North Carolina area then message me @BarbieSingle28.    ...
  • Well Endowed Shemale for Man in Winston-SalemWell Endowed Shemale for Man in Winston-Salem Hung Shemale for Man in Winston-Salem I am Blanca. I can provide top or bottom service. Bareback if you're clean. Love oral sex both giving and receiving. Say hello cause I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me privately at BlancaShemale32 for my latest u...
  • Local Shemale Seeking Man for Wild Fun in Winston-SalemLocal Shemale Seeking Man for Wild Fun in Winston-Salem Hey sexy, looking for a hot shemale to fulfill all your wildest fantasies? Well, look no further because I'm Carlee and I'm here to give you the time of your life. I'm a kinky shemale who loves it all - from being a top to a bottom, giving blowjobs, getting my ass pounded, sucking cock, and making...
  • Erotic Enchantment Awaits YouErotic Enchantment Awaits You Hey there! I'm Sharlene, a transgender beauty from Winston-Salem, North Carolina. I love being part of the LGBTQ community because it allows me to express my true self without any judgment. If you're looking for a fun and adventurous date, then look no further! I enjoy exploring local spots like ...
  • Elisabeth waiting to be your QueenElisabeth 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...
  • Transgender Temptation in Winston-SalemTransgender Temptation in Winston-Salem Hey there, I'm Casey from Winston-Salem, North Carolina. I may not fit into society's typical mold, but that's what makes me unique and special. I love embracing my true self as a transgender individual and being part of the LGBTQ community. If you're looking for someone who is genuine, fun-loving...
  • Looking for Love and Adventure! 🌈Looking for Love and Adventure! 🌈 Hey there, lovely people of Winston-Salem! My name is Raye, and I'm a proud transgender individual who's ready to embrace life and find someone special to share it with. 💖 I may not have the typical body type you'd expect, but trust me when I say that my heart is overflowing with love and kind...
  • Tempting Transgender in Winston-SalemTempting Transgender in Winston-Salem Hey there! I'm Cathryn, a transgender woman from Winston-Salem, North Carolina. I may not be your typical girl, but that's what makes me unique and special. I love embracing my true self and being a part of the LGBTQ community. It's all about love and acceptance, right? 😊 I'm looking for someo...
  • Trans Man waiting for right date with hot beautyTrans 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 ...
  • Discover Love and Adventure with Krista, the Transgender Beauty of Winston-Salem!Discover Love and Adventure with Krista, the Transgender Beauty of Winston-Salem! Hey there! 💖 My name is Krista, and I'm a vivacious transgender woman living in the charming city of Winston-Salem, North Carolina. If you're looking for a genuine connection filled with laughter, excitement, and understanding, then look no further! So, let me tell you a little about myself. I...
  • Brandi 27 tall slim hot trans chick 8.5 inchBrandi 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 naugh...
  • Spark up some magic with Ashli in Winston-Salem!Spark up some magic with Ashli in Winston-Salem! Hey there! I'm Ashli, a fun-loving transgender gal from Winston-Salem, North Carolina. I love exploring the local scene and trying out new restaurants like Mozelle's Fresh Southern Bistro or grabbing a coffee at Camino Bakery. I enjoy being part of the LGBTQ community because it allows me to exp...
  • Raunchy Shemale Seeking Local Man for Hot Encounters!Raunchy Shemale Seeking Local Man for Hot Encounters! Are you ready to have the time of your life with a sexy shemale like me, Janessa? I'm looking for a man in Winston-Salem who can handle all the naughty fun I have in store. I love being both a top and a bottom, so we can switch things up and explore all kinds of pleasures together. Whether you wan...
  • Sexy Shemale Vicki Looking for Hot Fun in Winston-Salem!Sexy Shemale Vicki Looking for Hot Fun in Winston-Salem! Hey there, I'm Vicki, a hot shemale from Winston-Salem looking for a local man to have some wild and raunchy fun with. I love getting down and dirty, so if you're into that too, then we'll definitely hit it off! I'm a top shemale who loves giving blowjobs and getting my tight ass pounded hard. I en...
  • Hot Shemale in Winston-Salem Ready to Play and Ride Your Huge CockHot Shemale in Winston-Salem Ready to Play and Ride Your Huge Cock Hey there, I'm Jenette, a sexy shemale in Winston-Salem looking for a local man to have some wild fun with. I love getting down and dirty, so if you're into it too, we'll be a perfect match! I enjoy giving sloppy blowjobs, riding your throbbing cock, and gagging on your huge dick until you explode w...
  • Sultry Transgender seeking Connection in Winston-SalemSultry Transgender seeking Connection in Winston-Salem Hey there! I'm Dedie, a proud transgender woman from North Carolina. I love embracing my true self and being part of the LGBTQ community. If you're looking for someone who's confident, fun-loving, and open-minded, then I might just be the one for you. I enjoy exploring new places in Winston-Salem...
  • Transgender Temptation in Winston-SalemTransgender Temptation in Winston-Salem Hey there, I'm Lyndell from Winston-Salem, North Carolina. I'm a curvy Latina beauty who loves embracing my true self as a transgender individual. Being part of the LGBTQ community brings so much joy and authenticity to my life. If you're looking for a fun and open-minded date, look no further! I...
  • Sexy Shemale Sofia Seeking Hot Man for Wild FunSexy Shemale Sofia Seeking Hot Man for Wild Fun Hey sexy studs, I'm Sofia, a raunchy shemale from Winston-Salem looking for a local man to play with. I love getting down and dirty, exploring all kinds of naughty pleasures. If you're into a wild time, I'm your girl!Come meet me for some steamy action at Club Cabaret or The Treasure Club. We can ge...
  • SHEMALE HOOKUPS! Wanna Have a Great Time in Winston-Salem, North Carolina? SHEMALE HOOKUPS! Wanna Have a Great Time in Winston-Salem, North Carolina? HOT!  SHEMALE HOOKUPS  "The girl with a naughty little secret in her panties!" SIGNUP FREE: INSTANT ACCESS!  Shemale Profiles Browse Uncensored Photos, Swap Your Pics, Join Live Web Cams, Swap Private Messages, Sext & Hook Up! Join free for Instant Access to the Wins...
  • Hot Shemale in Winston-Salem Ready to Play and FuckHot Shemale in Winston-Salem Ready to Play and Fuck Hey there, I'm Elaine, a sexy shemale in Winston-Salem looking for a local man who can handle all my dirty desires. I love being both a top and a bottom, giving and receiving blowjobs, getting my tight ass pounded hard, sucking on throbbing cocks, and making sure we both reach mind-blowing orgasms. ...
  • Spicy Hot 🌶 Tranny Girl from Colombia Spicy Hot 🌶 Tranny Girl from Colombia Latina Tranny Girl in Winston-Salem Hey guys, I am Gabriella and I am looking for a longterm relationship with a gentleman who love sex as much as I do! I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery except breasts. I am smooth and clean, very fe...
  • Hot Shemale Nance Looking for Local Man to Play and FuckHot Shemale Nance Looking for Local Man to Play and Fuck Are you ready to experience the wildest night of your life? I'm Nance, a sexy shemale from Winston-Salem, North Carolina, looking for a man who can handle all of my desires. I love being both a top and a bottom, so get ready for some intense action. I enjoy giving sloppy blowjobs and having my t...
  • TS M2F Top in Winston-SalemTS M2F Top in Winston-Salem TS Top Seeking Man in Winston-Salem I'm Sandi wants to meet hot guy for fun and hot sex. Age 28 with long blonde hair, smooth skin and a great body.  Non op functional, nice big ladystick for your pleasure! 😈  Love oral sex, anal sex and yummy kinks of all sorts. I love to explore kink...
  • Sexy Shemale Looking for Hot Fun in Winston-SalemSexy Shemale Looking for Hot Fun in Winston-Salem Are you ready to have the time of your life with a kinky shemale like me? My name is Rebe and I'm looking for a local man who can handle all my dirty desires. I love being on top and taking control, but I also enjoy getting down on my knees and giving sloppy blowjobs. Let's explore each other's bo...
  • August 21st, 2025
  • Come Dance with Me Under the Stars TonightCome Dance with Me Under the Stars Tonight Hey there! I'm Cinderella from Winston-Salem, North Carolina. I may not have a fairy godmother, but I do have a magical spirit that shines bright. Being transgender has allowed me to embrace my true self and connect with others who understand the journey of LGBTQ+ community. I love exploring new ...
  • Spark up some magic with me!Spark up some magic with me! Hey there! I'm Eveline, a proud transgender woman from Winston-Salem, North Carolina. I may not fit into society's typical norms, but that's what makes me unique and special. I love embracing my true self and connecting with others who appreciate authenticity. I enjoy exploring new places in the ...
  • Hot Shemale in Winston-Salem Ready to Play!Hot Shemale in Winston-Salem Ready to Play! I love being a shemale and I'm always looking for a man who can handle all that I have to offer. My name is Faye and I'm seeking a local man for some wild and raunchy fun. I enjoy everything from deepthroating your cock to riding you until we both explode with pleasure. I love giving sloppy blow...
  • New Body New MeNew 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...
  • Looking for Love and AdventureLooking for Love and Adventure Hey there! My name is Agnella, and I'm a transgender woman living in Winston-Salem, North Carolina. 🌈 I wanted to write this ad to put myself out there and hopefully find someone special who appreciates me for who I am. So, let me tell you a bit about myself. Physically, I have a curvy body ty...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Hey there, I'm a naughty shemale named Rhiamon from Winston-Salem, North Carolina. I'm on the hunt for a man who can handle all my dirty desires. I love to be on top, dominating you with my huge throbbing cock. I'll make you gag on it until you're begging for more.I also enjoy getting down and dirty...