Sheboygan, Wisconsin Shemale Dating Classifieds

Sheboygan, Wisconsin shemale dating classifieds. Meet local crossdressers, transexuals and shemales for romance, sex or just make new transgender friends. escorts, body rubs & sex service listings. Select your location below to find shemales near you. It's free to search or post your own ad!

Home / Shemale Dating /

Show Ads In: Appleton / Oshkosh | Duluth / Superior | Eau Claire | Green Bay | Janesville | Kenosha-Racine | La Crosse | Madison | Milwaukee | Sheboygan | Wausau

  • April 9th, 2025
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Sheboygan Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Sheboygan. 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 appreciates w...
  • TS m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Sheboygan 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...
  • Hot sexy shemale doll visiting Sheboygan now Hot sexy shemale doll visiting Sheboygan now Shemale Visiting Sheboygan Very hot sevy and curvy shemale chick with 8 inch lady stick. Message me on my profile page @TaylaShemale1. Seeking kind gentleman for romance and fun. Possible long term with the right man. ...
  • Having fun and Staying YoungHaving 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....
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! SheboyganYOUR EBONY SHEMALE - big boobs and a BIG COCK! Sheboygan Hot Hot Hot! Sinead, a black shemale in Sheboygan ready to make all of your  wildest fantasies come true! πŸ’‹πŸ”₯ My Pictures and Profile! -- You want to find a sexy ebony shemale in  Sheboyganto fulfill all your dreams? Then stop searching because I am ready to make  all of your d...
  • Sexy Shemale Sheboygan I know You Want to Play Sexy Shemale Sheboygan I know You Want to Play FEMININE AND SECURE SHEMALE  Hot and kinky shemale seeking a hot and fun guy who isn't scared of a beautiful and secure Trans Woman.. I'm located in Sheboygan; I am AlaneTS and  I am here to fulfill all your desires. If you are in the area or planning to be. and  looking for a hot an...
  • April 8th, 2025
  • TS Latina Bombshell Craving a Real Man to Handle Her πŸ‘πŸ”₯TS Latina Bombshell Craving a Real Man to Handle Her πŸ‘πŸ”₯  Hola, papi 😘 You are my TS Latina fantasy because I carry your weight in all  the right places and your softness in all the other places and my body is made for late nights  and louder moans. My skin is golden, my tongue is bilingual, and my hips don’t  lie... especiall...
  • Wisconson - Male Seeking Shemale for FUN!!Wisconson - Male Seeking Shemale for FUN!! I have always wanted to taste a shemale.. 🀫  Hi I'm Brad, I've been living in Sheboygan for about 2 years. I want to get out and try some new things.. With some new people. I want us to enjoy each other and have some fun. Freaky sex and maybe explore Wisconsin and see what fun and naughty t...
  • Superior Massage by gorgeous T-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Sheboygan 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: GayleT...
  • Spicy 🌢  Latina Shemale in Sheboygan Ready to Fill You πŸ˜‰πŸ˜‰ Spicy 🌢 Latina Shemale in Sheboygan Ready to Fill You πŸ˜‰πŸ˜‰ LATINA SHEMALE SEEKING πŸ”₯🌢  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Sheboygan.  Don't look any further, because I'm here to make all your wet dreams come true. My name is MARIA TS and I am a pre-op transgender woman who loves...
  • Beautiful Krystale 25 Sheboygan visiting nowBeautiful Krystale 25 Sheboygan visiting now Beautiful Shemale Visiting Sheboygan Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me.  Krystale25shemale Age: 25 Location: Sheboygan Sex: Shemale Seeking: Man ...
  • Hi Guys!! I am looking for someone fun!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! ...
  • THE RIGHT GUY FOR THE JOB!!!THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! πŸ˜‰ My name is Frank and I'm here to see if I can find any transgender ladies who wants a real man to treat them right.. I'm living in xxxx but I'm willing to travel. I have a great house we can have some fun in as well. I have a HOTTUB, arcade, th...
  • FtM seeking Princess Bride in SheboyganFtM seeking Princess Bride in Sheboygan FtM seeking Woman in Sheboygan Hi, I'm Andy, age 33, FtM transgender man living in Sheboygan. 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 @AndyF...
  • Erotic exotic Asian queen in Sheboygan now (25)Erotic exotic Asian queen in Sheboygan now (25) Asian Transexual in Sheboygan Stunning TS - Talia 25. 5' 8" 140lbs, non op, loves sex. Long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information....
  • M-F trans woman wants a dateM-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....
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Sheboygan 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 in it...
  • Email Local Shemales Now! πŸ’ŒEmail Local Shemales Now! πŸ’Œ 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 πŸ˜‰.. Do you want to meet local shemales who want to fuck and have some sex...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Sheboygan Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Sheboygan to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Online Cha...
  • She-male looking for hot date to please. She-male looking for hot date to please. Asian Shemale in the Sheboygan Area Hot Asian shemale wants to date and please you in the art of erotic passion. I'm non op, fully functional, lovely and funny. Please to contact me @CarmelShemaleXXX. My name is Carmel. I'm 33 years old. I like to explore your sexual fantasies! Let's make them com...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Sheboygan )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Sheboygan ) Sexy Crossdresser Elissa Looking for Hot Fun in SheboyganπŸ’‹    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 am a...
  • BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK πŸ†πŸ˜‰BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK πŸ†πŸ˜‰ BBC SHEMALE - BLACK TRANSπŸ’Ž let's play with each others cocks! Hey there boo thang, I know you're going to like what you see. Shiit, I have something for you baby. I love being feminine and sexy. I do still have my penis and I love to use it. I want to see your mouth on it infact.. Would you...
  • One Night, No Rules, Just Pleasure… One Night, No Rules, Just Pleasure… Sheboygan I'm Having a Night to Myself No Strings, just fun.. TS Seeking...🀫  A man who knows what he wants, but also a man who can be tempted, that’s  what I like.  We should begin with eye contact, a slow touch, and perhaps truth or  dare while drinking cocktails...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Sheboygan 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 ...
  • Well Endowed Shemale is beautiful Sheboygan 32Well Endowed Shemale is beautiful Sheboygan 32 Well Endowed Shemale in Sheboygan I am Blanca. I am ready to eat your manhood now. Top or bottom. Bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me at BlancaShemale32 for my latest pictures and proof of my size!&n...
  • TS Bombshell Looking for a Man Who Can Keep Up! πŸ’‹ SheboyganTS Bombshell Looking for a Man Who Can Keep Up! πŸ’‹ Sheboygan  Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun! View More of My Pictures πŸ“Έ Are you the sort of man who enjoys  just a touch of danger, a touch of excitement, and a lot of passion? I’m the  trans beauty you’ve been dreaming of — sexy...
  • I Need a Sexy Man to Tame Wild Willy!I Need a Sexy Man to Tame Wild Willy! Hung Sheboygan Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Sheboygan 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 Starbucks and se...
  • TS Latina Fantasy Girl – Let Me Rock Your World πŸ’‹πŸ”₯TS Latina Fantasy Girl – Let Me Rock Your World πŸ’‹πŸ”₯  Mira, papi… I’m not just sexy — I’m dangerous 😘 ( View My Dating Pictures Here ) My  TS Latina body features silky skin and long hair and full lips and a tight and juicy physique. I  dress to kill. My moans produce musical sounds. My movements flow throug...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Sheboygan 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 relationship....
  • πŸ‘‘ Chocolate Queen with Soft Curves & Naughty Desires πŸ”₯πŸ‘‘ Chocolate Queen with Soft Curves & Naughty Desires πŸ”₯  πŸ”₯| Do you feel that you want something new and exciting and that you want to  remember for a long time? I am a hot, all natural ebony TS with all the right amount  of curves and a naughty and adventurous spirit. I don’t just know how to tease, please and  make you want ...
  • Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯  I am a confident, strong and open minded man, who knows what I want from a woman  – a sexy, elegant and fun loving TS woman to share unforgettable moments with. I am here to  explore and enjoy every second of it, whether it is a casual hookup, a fun date or a  deep connect...
  • Ebony Shemale in Sheboygan ❀️😘 Seeking Male for Naughty Fun!Ebony Shemale in Sheboygan ❀️😘 Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies πŸ’‹ Are you looking for a hot and kinky black shemale in Sheboygan? Look no further because I am here to satisfy all your desires. My name is StefanieBBC and I'm an Ebony Shemale..  I am a stunning transgender woman who loves to p...
  • TS Latina Dream Girl – Ride Me Like a Telenovela πŸ˜ˆπŸ“ΊTS Latina Dream Girl – Ride Me Like a Telenovela πŸ˜ˆπŸ“Ί  Have you ever imagined a sensual Latina woman with large thighs and a narrow waist and a hidden sexual  secret? That’s me, papi 😘 I’m your spicy TS novela — dramatic,  passionate, and unforgettable in the bedroom. Message me here babe - I want your hands on my h...
  • πŸ‘  Classy on the Streets, Naughty in the Sheets – Let’s Play πŸ’‹πŸ‘  Classy on the Streets, Naughty in the Sheets – Let’s Play πŸ’‹  πŸ’– Just one taste and you’ll be addicted! I am a beautiful, funny TS,  a queen of color with a nice curvy body, beautiful eyes, and a touch that will drive  you crazy. I know what a man needs and how to make him satisfied and craving for more.  I am looking for a confide...
  • Your Shemale Addiction 😈πŸ₯΅ Starts NowYour Shemale Addiction 😈πŸ₯΅ Starts Now Shemale Seeking Male.. Your Fantasy Starts Here 24yr old Transsexual/Shemale in Sheboygan seeking some fun and campanionship. I would like hookups and I'm also wanting love. I think we should play some plans and see what we can come up with.. I'm open minded and ready!! Take a min to View my P...
  • Flirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆFlirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆ  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.  πŸ’‹ πŸ’Ž Bath g...
  • Looking for My TS Queen πŸ‘‘πŸ’‹Looking for My TS Queen πŸ‘‘πŸ’‹ I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. πŸ’• I appreciate a woman who knows her worth and loves to be treated right. Whether it’s a romantic dinner, steamy nights, or spontaneous adventures,...
  • Email Sheboygan Shemales❀️‍πŸ”₯Email Sheboygan Shemales❀️‍πŸ”₯ I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...
  • Sassy CD Looking for a Real Man 😘πŸ”₯Sassy CD Looking for a Real Man 😘πŸ”₯  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...
  • πŸ–€ Ebony TS Playmate with a Curvy Body & a Wild Side 😘 SheboyganπŸ–€ Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Sheboygan πŸ‘ Thick thighs, soft lips, and a wild side—what more could you want? I’m a sensual, passionate ebony TS beauty who knows how to make a man feel special, desired, and completely satisfied. Whether we take it slow and intimate or dive into a steamy, no-strings-attached night of passion,...
  • Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates.Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Sheboygan Area Hi, my fem name is Gloria. I'm a married crossdresser in the Sheboygan 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 dressin...
  • Free Wisconsin Transexuals GuideFree Wisconsin Transexuals Guide Wisconsin Transexuals Guide The Wisconsin Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free Wisconsin Transexuals Guide online.  Where to Meet Transexuals in W...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Sheboygan 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 interesting hi...
  • Flirty, Dirty, and Ready for Some Fun ❀️ Sheboygan Shemale Seeking Male Flirty, Dirty, and Ready for Some Fun ❀️ Sheboygan Shemale Seeking Male Local Shemale Seeks Man For Adventure!  TS Vixen, are you ready to play? Sweet, sultry and a little bit  wild, I am a trans goddess and I do enjoy my men to be as much as a wild  as I am. 😘I don’t want to talk – I want to try something a bit  more exciting. How ab...
  • 🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘 πŸ’– Hey, Handsome! I’m a sultry, curvy ebony TS  here in Sheboygan... I'm Pre Op, ready to play, with a body made for pleasure and a heart full of passion. Discreet, sensual, and looking for a man who knows how to handle me. Let’s make tonight unforgettable! 😘 I'm writing this t...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Sheboygan Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • Tiffany Shelle - Your Sheboygan Tranny Girlfriend! πŸ’žTiffany Shelle - Your Sheboygan Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Sheboygan It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGIT βœ¨πŸ’ž SKILLED, Exotic and Erotic πŸ’¦ πŸ₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% function...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy \ Sheboygan!HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Sheboygan! 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 Sheboygan!  No strings - just great times, so join my page free for instant access! Shemale Gia's Sheboygan Sexbook @ShemaleGia27 Photos: 4...
  • Your Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ SheboyganYour Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ Sheboygan 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. πŸ’‹ πŸ‘  Feminine, fun and ...
  • II'm a Horny Shemale πŸ˜ˆπŸ’‹ Looking For Sex Tonight!! Sexy ShemaleπŸ’Ž Ready to Rock Your World! Local Transsexual - TGIRL Sext App πŸ“² 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...