Milwaukee Transgender Classifieds

Browse Milwaukee 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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February 1st, 2026
I’m a Sexy and Naughty T-Girl Here in Milwaukee. Milwaukee T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Milwaukee 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...
Trans Playmate Sex Kitten... Ebony trans woman in Milwaukee 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...
Transgender Goddess for Late-Night Escapes & Filthy Fun 🌙💋  It’s late. You’re restless. And you’re craving something… different 😏 - 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...
Milwaukee💋 TS Tina – Your Naughty Escape, Anytime, Anywhere 🌎🔥 Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world 😘 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...
Hot trans chick with nice boobs Hot trans chick in Milwaukee. 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 ...
Free 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...
TS Sugar Baby 💎 Femme, Flirty & Looking for the Right Man in Milwaukee I’m a transgender sugar baby who loves femininity, attention, and being appreciated by a confident man who knows exactly what he wants.. Confidence speaks louder than words. Gentle touches matter more than grand gestures ever could. Let's Link Up Babe - Fond of the sugar dynamic. Getting pamp...
I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Milwaukee I'm queen Delilah a trans woman here in Milwaukee 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...
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 ...
Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Milwaukee 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...
SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Milwaukee Secret Crossdressing Hookups in Milwaukee 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...
Latina TS Dirty Girl Looking for a Gentleman's Dark Side 🔥👠  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 😘 I need you to undress me gr...
Strict Shemale Dominatrix in Milwaukee - @DesireeTransDomme Powerful African-Queen Dominatrix in Milwaukee I am full-time professional Domme Desiree. My Milwaukee 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...
Superb Shemale in Milwaukee... T-Girl for NSA Encounters in Milwaukee When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Milwaukee. 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 ...
The Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Milwaukee 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...
January 31st, 2026
Having 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...
I'm a Horny Shemale 😈💋 Looking For Sex Tonight!! Sexy Shemale💎 Ready to Rock Your World! Local Transsexual - TGIRL Sext App 📲 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...
I'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 Milwaukee 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 sexy shemale doll visiting Milwaukee now Shemale Visiting Milwaukee 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...
Tiffany Shelle - Your Milwaukee Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Milwaukee It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT ✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% function...
Road Head Sally Drivin' Hard in Milwaukee Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Milwaukee. 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...
Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Milwaukee 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...
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 Milwaukee tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer th...
Tainted Love - Beyond Compare! Kinky Trans Woman in Milwaukee Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Milwaukee. 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...
Spicy and Hot T-Girl from Colombia Latina T-Girl in Milwaukee 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...
💕 Milwaukee Trans Sugar Baby Seeking Chemistry, Comfort & Consistency Hey Milwaukee 💋Feminine in feel, confident in who I am - a transmasculine sugar baby who prefers loose bonds, quiet encounters. Dinner under soft streetlights near the Third Ward draws me in, just as much as spinning turns by the lake after dark, or still evenings when traffic fades. Smooth manne...
HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Milwaukee! 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 Milwaukee!  No strings - just great times, so join my page free for instant access! Shemale Gia's Milwaukee Sexbook @ShemaleGia27 Photos: 4...
Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Milwaukee Look no further honey, I'm Franny an Ebony trans woman here in Milwaukee 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...
Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Milwaukee 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...
January 30th, 2026
Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Milwaukee Area Hi, my fem name is Gloria. I'm a married crossdresser in the Milwaukee 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...
Well Endowed Shemale is beautiful Milwaukee 32 Well Endowed Shemale in Milwaukee 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 @BlancaShemale32 with your recent pic or selfie for my latest pictures and ...
Don't Worry I Bite! Feisty redhead trans in Milwaukee 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...
Email Milwaukee Shemales Now! 💌 Want to Hookup and Find Milwaukee 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 😉.. Do you want to meet local shemales who want to fuck and have some sexy fun? I d...
Email Milwaukee Shemales❤️‍🔥 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...
Flawlessly gorgeous trans bombshell in Milwaukee Trans MtF for Man in Milwaukee 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...
Penny for your thoughts? Penny TS in Milwaukee 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 ...
Ebony TS Playmate for Men Who Know What They Want 🖤🍆  If you are the type of person who does not want to waste time with games or small  talk… we are already off to a good start 😘 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...
Low-Key TS Sugar Baby 🌙 Soft Vibes, Selective Energy in Milwaukee I’m a TS sugar baby who keeps things calm, classy, and intentional. Evenings without noise, talks that flow naturally - these mean something to me. Confidence shows in stillness, not noise. Soft in manner, sharp in choices. Comfortable standing out, never trying too hard. 😌💄Let's Link Up...
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 Milwaukee area and are interested then drop me a line and introduce yourself. You ca...
Black/Ebony Transsexual - Your New Addiction – One Taste and You’ll Beg for More 🍑💋  Warning: I’m addictive 😘 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...
Selena 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 ...
Erotic exotic Asian queen in Milwaukee now (25) Asian Transexual in Milwaukee 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...
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 M...
!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Milwaukee Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Milwaukee 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...
SuperFabulistic Shawna in Milwaukee... Tgirl Shawna here in Milwaukee tryna meet some hot guy for a hookup. I'm a freaky ebony hottie down for some serious booty call. Imma make you holla baby! I got a big treat gonna be right up your alley. So, come get you some of this superfabulistic Shawna - you know you WANNA! And come by here and s...
British T-girl Seeking Classy Gentleman in Milwaukee... 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 Milwaukee and am financially independent and looking for a gentleman who is like-minded, equally solvent and has exce...
TS Temptress Ready to Ruin You (In the Best Way) 😈💦 Milwaukee  Hey lover 😘 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...
Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Milwaukee 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!&...
January 29th, 2026
Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Milwaukee 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: Milwaukee, WisconsinA...
New Body New Me M2F in Milwaukee 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...

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