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!

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  • June 4th, 2026
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  • 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...
  • 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...
  • 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...
  • 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...
  • 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 ...
  • 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...
  • Sparkle with me under the North Carolina moon πŸŒ™Sparkle with me under the North Carolina moon πŸŒ™ Hey there! I'm Lesya, a transgender beauty from Winston-Salem looking for someone special to share some magical moments with. πŸ’« 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...
  • 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...
  • 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 ...
  • Tempting Transgender Tiana Looking for LoveTempting Transgender Tiana Looking for Love Hey there! I'm Tiana, a fun-loving transgender babe from Winston-Salem, North Carolina. I may not fit society's norms, but I embrace my uniqueness and love being part of the LGBTQ community. If you're into exploring new adventures and sharing some laughs along the way, then I'm your girl! I enjo...
  • Transgender Temptation in Winston-SalemTransgender Temptation in Winston-Salem Hey there, I'm Debbra from Winston-Salem, North Carolina. I'm a curvy and confident transgender woman who loves embracing my true self. Being part of the LGBTQ community has brought so much joy and acceptance into my life. If you're looking for someone who is genuine, fun-loving, and open-minded, ...
  • 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...
  • 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...
  • 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. πŸ’– 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...
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  • 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...
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  • 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...
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  • 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.    ...
  • 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...
  • Looking for Love and Adventure! <br>Looking for Love and Adventure!
    Hey there! My name is Kailey and I'm a transgender woman living in Winston-Salem, North Carolina. 🌈 I wanted to put myself out there and see if I can find someone special who appreciates me for who I am. πŸ’• I'm a free-spirited individual with a zest for life, always up for new experiences an...
  • 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 ...
  • 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!  ...
  • 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....
  • Hot Shemale in Winston-Salem Ready to Play and FuckHot Shemale in Winston-Salem Ready to Play and Fuck I'm a sexy shemale named Paulina looking for a local man who can handle my tight, throbbing cock. I love giving sloppy blowjobs and getting my ass pounded hard. I want to make you cum over and over until we both collapse in ecstasy. I enjoy being both a top and a bottom, so we can switch it up a...
  • 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 M2F Preop Trans, Lovely Surprise Waiting in my Panties πŸ’–πŸ’–Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties πŸ’–πŸ’– 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...
  • Sexy Shemale Allene Seeking Hot Fun in Winston-SalemSexy Shemale Allene Seeking Hot Fun in Winston-Salem Looking for a man who can handle all my shemale 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 bodies and make each other cum over and over again. I have a tight ass that loves to be played with, so ...
  • June 3rd, 2026
  • 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...
  • 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 ...
  • 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...
  • 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...
  • Euphoria Awaits: Transgender Beauty Seeking ConnectionEuphoria Awaits: Transgender Beauty Seeking Connection Hey there! I'm Lyndsie, a transgender woman from Winston-Salem, North Carolina. I may not fit society's mold, but that's what makes me unique and special. I love embracing my true self and being a part of the LGBTQ communityβ€”it's like finding a second family who understands and supports me. πŸ’–...
  • Raunchy Shemale Nanette Seeking Local Man for Wild FunRaunchy Shemale Nanette Seeking Local Man for Wild Fun Hey boys, I'm Nanette, a hot and horny shemale from Winston-Salem looking for a man who can handle all my dirty desires. When it comes to getting down and dirty, I love it all. From deepthroating your cock until you gag, to riding you hard while you spank my tight ass, I'm up for anything that will ...
  • 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...
  • Elegantly Transgender Seeking Connection in Winston-SalemElegantly Transgender Seeking Connection in Winston-Salem Hey there! I'm Tammy, a transgender woman living in Winston-Salem, North Carolina. I may not fit society's mold of what a woman should look like, but I embrace my unique body type and ethnicity with pride. Being LGBTQ has allowed me to explore different aspects of my identity and connect with othe...
  • 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 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...
  • 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...
  • Elegantly Transcending BoundariesElegantly Transcending Boundaries Hey there, I'm Netti from Winston-Salem, North Carolina. I may not fit society's mold, but that's what makes me unique! As a transgender individual, I embrace my true self and love connecting with others who appreciate authenticity. Whether you're LGBTQ+ or an ally, let's chat over a cup of coffee...
  • 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...
  • Transgender Temptation in Winston-SalemTransgender Temptation in Winston-Salem Hey there, I'm Clarette from Winston-Salem, North Carolina. I may not fit into society's traditional boxes, but that's what makes me unique and fabulous! Being transgender has allowed me to truly embrace my authentic self and connect with others in a deeper way. I love exploring LGBTQ+ events and ...
  • 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. ...
  • Looking for Love and Adventure in Winston-Salem!Looking for Love and Adventure in Winston-Salem! Hey there! My name is Sayre, and I'm a transgender person living in the beautiful city of Winston-Salem, North Carolina. πŸ’œ I might not fit into society's traditional mold, but that's what makes me unique! I believe that being trans is a beautiful journey of self-discovery and authenticity. πŸŒ...
  • June 2nd, 2026
  • 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...