Sheboygan Transgender Classifieds

Browse Sheboygan transgender classifieds to meet local transexuals, crossdressers and shemales for sex, dating or friendship. Contact any of these trans advertisers to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all trans classifieds, or post your own adult ad!

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  • June 15th, 2025
  • 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...
  • 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...
  • Spicy and Hot T-Girl from ColombiaSpicy and Hot T-Girl from Colombia Latina T-Girl in Sheboygan Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...
  • 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 ...
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Sheboygan 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. I a...
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Sheboygan Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Sheboygan men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  About m...
  • Tiffany Shelle - Your Sheboygan Tranny Girlfriend! ๐Ÿ’žTiffany Shelle - Your Sheboygan Tranny Girlfriend! ๐Ÿ’ž Tranny Escort - Top/Bottom/GFE in Sheboygan It’s Tiffany Shelle your perfect tranny girlfriend ๐Ÿฅฐ ๐Ÿ’• SAFE๐Ÿ’• ๐Ÿ’ฏ LEGIT โœจ๐Ÿ’ž SKILLED, Exotic and Erotic ๐Ÿ’ฆ ๐Ÿฅฐ I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% function...
  • 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 @PennyTSswitch!! I'm a mixed race sweetheart, looking for a nice man who will enjoy being with me. Let's enjoy having some fun, hot dates and ...
  • British T-girl Seeking Classy Gentleman in Sheboygan...British T-girl Seeking Classy Gentleman in Sheboygan... 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 Sheboygan and am financially independent and looking for a gentleman who is like-minded, equally solvent and has exce...
  • June 14th, 2025
  • I want to be a whoreI want to be a whore I am a transexual very hot. Good with my mouth and my ass. Comment on my photos. I would appreciate it if you downloaded my photos and share me with other men in the Sheboygan area. Click here and come see me anytime!...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Sheboygan. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Want ...
  • 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...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Sheboygan? Hey, I am Jasmin, with a great body and busty. Hit me up @SweetJasminT. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for a fun date and see where it goes! I'm preop and functional, very sex positive and love all sort...
  • Beautiful Krystale 25 Sheboygan visiting nowBeautiful Krystale 25 Sheboygan visiting now Beautiful Preop 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.  Krystale25shemale Username: @Krystale25shemale Age: 25 Location: Sheboygan, Wisconsin Sex: MtF Trans Seeking: Man...
  • Iโ€™m a Sexy and Naughty T-Girl Here in Sheboygan.Iโ€™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...
  • Having fun and Staying YoungHaving fun and Staying Young Young-ish 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 @SherryTransFem33 and message me. Send your pics for mine. I'm hoping to find real chemistry an...
  • Flawlessly gorgeous trans bombshell in SheboyganFlawlessly gorgeous trans bombshell in Sheboygan Trans MtF for Man in Sheboygan I transitioned 6 years ago at the age of 18. I'm still fully functional but live 24/7 as a female. I pass flawlessly so let's go out on the town! I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedroom...
  • SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now!SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now! HOT!  SHEMALE HOOKUPS  "The girl with a naughty little secret in her panties!" SIGNUP FREE: INSTANT ACCESS! Shemale Profiles Uncensored Photos Swap Your Pics Live Web Cams Private Messages Sext & Hook Up! Join free for Instant Access to the Trans Profiles  &...
  • II'm the Girl Your Mum 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 ...
  • !!!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...
  • Black/Ebony Transsexual - Your New  Addiction โ€“ One Taste and Youโ€™ll Beg for More ๐Ÿ‘๐Ÿ’‹Black/Ebony Transsexual - Your New Addiction โ€“ One Taste and Youโ€™ll Beg for More ๐Ÿ‘๐Ÿ’‹  Warning: I’m addictive ๐Ÿ˜˜ View My Ebony TS Profile here - I possess more than attractive features. I am a complete  TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and  thick thighs and soft lips and a hidden secret th...
  • Strict Shemale Dominatrix in Sheboygan - @DesireeTransDommeStrict Shemale Dominatrix in Sheboygan - @DesireeTransDomme Powerful African-Queen Dominatrix in Sheboygan I am full-time professional Domme Desiree. My Sheboygan area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will lear...
  • TS Temptress Ready to Ruin You (In the Best Way) ๐Ÿ˜ˆ๐Ÿ’ฆ SheboyganTS Temptress Ready to Ruin You (In the Best Way) ๐Ÿ˜ˆ๐Ÿ’ฆ Sheboygan  Hey lover ๐Ÿ˜˜ I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...
  • Email Sheboygan Shemalesโค๏ธโ€๐Ÿ”ฅEmail Sheboygan Shemalesโค๏ธโ€๐Ÿ”ฅ 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...
  • Hi Guys!! 32 y/o Trans looking for someone fun!Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Sheboygan for Man Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will be ...
  • A monster in the sheets, but a lady in the streets...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 Sheboygan area and are interested then drop me a line and introduce yourself. You ca...
  • 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 my wife doesn't approve. I REALLY need to let my fem side out to play! I'm seeking cross dres...
  • 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...
  • Latina TS Dirty Girl Looking for a GentlemanLatina TS Dirty Girl Looking for a Gentleman's Dark Side ๐Ÿ”ฅ๐Ÿ‘   Sweet on the surface. Filthy underneath. View My Trassexual Dating Profile Here - As a TS darling I present like a dream while  playing like a fantasy. Stockings. Heels. A tight dress. Soft skin. And a  throbbing surprise you’ll love exploring ๐Ÿ˜˜ I need you to undress me gr...
  • Partners in crime, or?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 S...
  • ๐Ÿ†๐Ÿ’ฆWisconsin Shemale Needing Sex๐Ÿ†๐Ÿ’ฆ๐Ÿ†๐Ÿ’ฆWisconsin Shemale Needing Sex๐Ÿ†๐Ÿ’ฆ Sexy Shemale  ๐Ÿ‘„๐Ÿ‘„Needing sex  in Wisconsin Wisconsin ๐Ÿ“ฒ  Dating App  I'm new to Wisconsin but I know how to use my nice cock and make you cum with it. I'm a transsexual or sometimes reffered to as a Shemale and I still have my nice cock and nice big boobies. Would y...
  • 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...
  • 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 @SelenaIsTrans and send me a message to set up a date. I like going out for food or drinks, having a great time and I especially like great sex! I am preop and can do top or bottom though I kind of prefer top ...
  • June 13th, 2025
  • Transgender Goddess for Late-Night Escapes & Filthy Fun ๐ŸŒ™๐Ÿ’‹Transgender Goddess for Late-Night Escapes & Filthy Fun ๐ŸŒ™๐Ÿ’‹  It’s late. You’re restless. And you’re craving something… different ๐Ÿ˜ - View My Transsexual Dating Profile - As  your TS fantasy girl I offer sultry and smooth vibes while delivering experiences beyond what your ex could have  imagined. My secret between...
  • Road Head Sally DrivinRoad Head Sally Drivin' Hard in Sheboygan Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Sheboygan. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or pa...
  • 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 big delicious lady stick, fully functions for top or bottom. Message me on my profile page @TaylaShemale1. Seeking a kind gentleman for romance and fun. I adore introducing men who are new to shemale sex. HMU! Possible long...
  • 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 masseuse, hot body, in great shape, and well hung. If you want to get together, Send me a private message Crystal27trans <3  Username: @Crystal27transLocation: Sheboygan, WisconsinA...
  • 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 and show you wh...
  • 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 ...
  • June 12th, 2025
  • The Trevor Project Saves Young LGBTQ+ LivesThe Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Sheboygan Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexu...
  • Email Sheboygan Shemales Now! ๐Ÿ’ŒEmail Sheboygan Shemales Now! ๐Ÿ’Œ Want to Hookup and Find Sheboygan 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're interested in ๐Ÿ˜‰.. Do you want to meet local shemales who want to fuck and have some sexy fun? I d...
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Sheboygan Look no further honey, I'm Franny an Ebony trans woman here in Sheboygan 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 don't have...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Sheboygan Tammy, 39, big tits!! Well hung, everything works, clean and so cute!! What more could you want in a gurl?!! How about you message me @Tammy39T and we can talk and meet! Send your recent pic for mine. Username: @Tammy39TLocation: Sheboygan, WisconsinAg...
  • Sheboygan๐Ÿ’‹ TS Tina โ€“ Your Naughty Escape, Anytime, Anywhere ๐ŸŒŽ๐Ÿ”ฅSheboygan๐Ÿ’‹ TS Tina โ€“ Your Naughty Escape, Anytime, Anywhere ๐ŸŒŽ๐Ÿ”ฅ Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world ๐Ÿ˜˜ I possess the right amount of softness while maintaining the perfect playful demeanor and I always welcome men who understand how to treat a genuine wild wom...
  • Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina ๐Ÿ’‹ I'm in Sheboygan 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 now.. ...
  • 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...
  • Erotic exotic Asian queen in Sheboygan now (25)Erotic exotic Asian queen in Sheboygan now (25) Asian Transexual in Sheboygan Stunning TS - Talia 25. Asian mixed race, non op, loves sex. Nice build with long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information. Classy in public but trashy in the bedroom. Versatile and attentive to your needs. Long...
  • June 11th, 2025
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Sheboygan 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 hi!&...
  • New Body New MeNew Body New Me M2F in Sheboygan Hi, I'm Natasha, newly transitioned, exploring this beautiful new chapter in my life, and ready to date. Gorgeous non-op 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 wi...