Sheboygan, Wisconsin Shemale Dating Classifieds

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  • July 15th, 2025
  • Superb Shemale in Sheboygan...Superb Shemale in Sheboygan... T-Girl for NSA Encounters in Sheboygan When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Sheboygan. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck ...
  • SheboyganSheboygan's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Sheboygan Hi you sexy man! I'm Toni a trans woman from here in Sheboygan. 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, functional and l...
  • 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...
  • 🍫 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...
  • 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...
  • I love a confident, seductive TS womanβ€”could you be the one? πŸ’‹I love a confident, seductive TS womanβ€”could you be the one? πŸ’‹  A handsome, intelligent and adventurous man, here looking to meet a gorgeous TS woman to have  excitement, chemistry and wild nights. I just love confident women who know what they want and I’m more  than ready to spoil, explore and indulge in pleasure together.  Handsome,...
  • 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 - 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...
  • 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...
  • I Need a STEAM ROLLER Baby!!!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 ...
  • July 14th, 2025
  • πŸ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & PleasureπŸ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure  πŸ‘‘ I am the Queen of Your Fantasies – Come Worship Me! I am  a gorgeous, confident, ebony TS, with a body built for pleasure and a mind full of naughty  ideas. If you are looking for high class experience, filled with deep pleasure, seductive touches and  sensual moments...
  • New Body New MeNew Body New Me M2F post-op in Sheboygan 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 Natas...
  • TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨  I am a dominant, attractive, and confident man looking for a beautiful transgender woman who enjoys being  admired, spoiled, and pleasured.  I am down for mutual attraction, passionate flames and unforgettable  moments. Whether it is a one time or if it is something on going I a...
  • 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...
  • 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....
  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Sheboygan Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Sheboygan Seeking!! Seduction Starts with One Look…Once I have your attention, baby, I don’t let go. 😏 I’m the trans woman you’ve been dreaming about—sexy, confident, and oh-so-willing to turn up the heat. Let’s start slow… a few drinks, a little teasing, some whispers abo...
  • Selena Trans girl cute looking for loveSelena 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....
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in SheboyganSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Sheboygan Secret Crossdressing Hookups in Sheboygan 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 private g...
  • 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...
  • 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...
  • πŸ‘ Your Secret Ebony Fantasy Is Just One Message Away πŸ˜œπŸ‘ Your Secret Ebony Fantasy Is Just One Message Away 😜  πŸ‘„ I am going to make your wildest dreams come true. I am a classy  yet freaky ebony trans beauty that loves to explore deep desires and steamy fantasies. If you are  a man that appreciates soft skin, full lips and a body made for pleasure then we need to  talk. If you are loo...
  • 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,...
  • Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹  You want flavor? Spice? A woman who can dance for you, then ride you like she  owns you? That’s me, papi 😘 I’m a curvy, high-femme  TS Latina with a pretty face, wild hips, and a very naughty surprise underneath. View My Latina TS Pictures - I love to  tease, fl...
  • Latina TS Firestarter – I Don’t Do β€œMild” πŸ”₯πŸ‘ Latina TS Firestarter – I Don’t Do β€œMild” πŸ”₯πŸ‘  I’m your next obsession, papi 😘 View More Pictures of Mine! TS. Latina. Voluptuous. Insatiable. And craving a man who can handle my curves, my tongue, and my need for deep, sweaty pleasure 😈 You’ll taste my perfume before I even touch you… and feel my body long after I lea...
  • 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...
  • II'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 Sheboygan 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 lives ...
  • 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...
  • 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 ...
  • I’m a Sexy and Naughty T-Girl Here in Sheboygan.I’m a Sexy and Naughty T-Girl Here in Sheboygan. Sheboygan T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Sheboygan 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  worries an...
  • 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...
  • 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...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Sheboygan 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 it g...
  • TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯  I am a tall, fit, and successful man and I have a taste for gorgeous TS women  who love to be adored, desired and pleasured. Whether you are looking for a wild  night, a passionate escape or something ongoing, I know how to treat a woman right. πŸ’‹ Must  have confidence, charm...
  • 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...
  • 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....
  • 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...
  • 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...
  • 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 ...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Sheboygan 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....
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Sheboygan 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 Messag...
  • 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...
  • 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...
  • Do you know the difference between a dick and a bucket of popcorn?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 Sheboygan tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer th...
  • πŸ’– Discreet, Naughty & Waiting for a Man Who Can Handle MeπŸ’– Discreet, Naughty & Waiting for a Man Who Can Handle Me  πŸ”₯ I’m an exotic ebony TS bombshell in Sheboygan with a love for steamy nights,  deep connections and uninhibited pleasure, keep it hot and wild and unforgettable! Whether you are looking for  an exciting adventure, a sensual night of passion or just something you’ve ne...
  • 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! ...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Sheboygan I'm queen Delilah a trans woman here in Sheboygan 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 scandalous posi...
  • Sheboygan Addicted to shemales... Male Seeking TSSheboygan Addicted to shemales... Male Seeking TS  A handsome, fit and confident man, seeking a stunning TS girl to spend exciting nights and incredible  moments with. I have a thing for flirty conversations, passionate chemistry and playful antics- if you  are looking for a casual meet or if we can make this a more regular thing, I ...
  • 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...
  • 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...
  • Twisted Sister - Loves to Ride.... and be Ridden!Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Sheboygan 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'm s...