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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  • April 15th, 2025
  • 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...
  • 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...
  • 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, Iโ€™m a sexy, sensual, tender, animal loving, bookworm. I am a bit of a flirty whore, who loves mystical magical movies and stories, so letโ€™s get that out in the open. If you live in the S...
  • 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...
  • 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...
  • 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...
  • Tiffany Shelle - Your Sheboygan Tranny Girlfriend! ๐Ÿ’žTiffany Shelle - Your Sheboygan Tranny Girlfriend! ๐Ÿ’ž Tranny Escort - Top/Bottom/GFE in Sheboygan Itโ€™s Tiffany Shelle your perfect tranny girlfriend ๐Ÿฅฐ ๐Ÿ’• SAFE๐Ÿ’• ๐Ÿ’ฏ LEGIT โœจ๐Ÿ’ž SKILLED, Exotic and Erotic ๐Ÿ’ฆ ๐Ÿฅฐ Iโ€™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 ...
  • 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 ...
  • 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...
  • April 14th, 2025
  • 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...
  • 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...
  • 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...
  • 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...
  • 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 ...
  • 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...
  • 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...
  • Dr FreakinDr Freakin'furter - Mine's Bigger Than Yours! White T-girl here and I'd bet mine is bigger than yours. We'll just let it be our little intimate surprise when the time comes. No one needs to know our business, Let's just keep it discreet. If you live in the Sheboygan area come see if you measure up! Click here for explicit photos. Look...
  • 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...
  • 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 hot and sweet and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl Gayle ๐Ÿ˜ Transgender World Profile Username: GayleTGirl Loca...
  • 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...
  • 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. Message me on my profile page @TaylaShemale1. Seeking kind gentleman for romance and fun. Possible long term with the right 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...
  • Ebony TS Playmate for Men Who Know What They Want ๐Ÿ–ค๐Ÿ†Ebony TS Playmate for Men Who Know What They Want ๐Ÿ–ค๐Ÿ†  If you are the type of person who does not want to waste time with games or small  talkโ€ฆ we are already off to a good start ๐Ÿ˜˜ I am a sexy, curvy TS  babe who loves attention, loves giving pleasure, and lives to be desired. I will come looking like  a dream and be read...
  • 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 youโ€™ll love exploring ๐Ÿ˜˜ I need you to undress me gr...
  • 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...
  • 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....
  • 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!&...
  • Letha Aims to Fill YOU With Her Love Gun!!!Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Sheboygan and I got a BIG love gun to whip and pound you with until you scream! I'm def top and alpha and don't take no shit! Imma make you suck me first just for foreplay then I'll throw you back for some hard insertio...
  • TS Sugar Baby๐Ÿ’Ž Your Perfect Trans Fantasy โ€“ Letโ€™s Make It a Reality ๐Ÿ’‹TS Sugar Baby๐Ÿ’Ž Your Perfect Trans Fantasy โ€“ Letโ€™s Make It a Reality ๐Ÿ’‹  ๐Ÿ“ Location: Sheboygan ๐Ÿ’– Seeking: Fun, Exciting, &  Discreet Connections Some about me.. Trans SugarBaby: Hey there! I belive I'm a stunning, sweet, and playful trans beauty who loves good  vibes, great chemistry, and unforgettable nights.. I'm in my early 20's and I...
  • April 13th, 2025
  • 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...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Sheboygan. Sheila wants to meet you. Hey all, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, top or bottom, love oral sex. Want to explore kinks? Me too!! Want to meet me? Send me a message @HotTransChick...
  • 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...
  • 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 ...
  • 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: Iโ€™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...
  • 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....
  • 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...
  • 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 am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedroom eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned! Sen...
  • 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!...
  • DonDon't Worry I Bite! Feisty redhead trans in Sheboygan full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to control...
  • 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....
  • 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...
  • 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...
  • 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 ...
  • 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....
  • April 12th, 2025
  • 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˜˜ Iโ€™m a high-femme TS bombshell โ€” curves for days, lips  made for kissing (and more), and a hunger that doesnโ€™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...
  • 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 Shemale Profiles  ...
  • 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.. ...
  • Brandi 27 tall slim hot trans chick fully functionalBrandi 27 tall slim hot trans chick fully functional Pre-op TS, fully functional in Sheboygan 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 big functioning ladyclit for top or bottom. I love oral sex!! Kink friendly, have toys to explore all ...
  • 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...