Milwaukee, Wisconsin Shemale Dating Classifieds

Milwaukee, 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!

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April 5th, 2025

Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Milwaukee 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 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your nau...

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...

Shy Transexual Escort in Milwaukee Shy transexual Camille here to tease you with my long functioning lady stick. Age 24, slim, healthy and physically fit. I love sex! I do top or bottom, special attention to your needs. Kink friendly so let me know what you like. I love it all. Explore your passion for trans women discreetly with an ...

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...

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...

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Latina TS Playmate – Sweet Accent, Dirty Thoughts 💃💋  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...

Shemale 4 Men 🍆💦 Milwaukee Ready Now!!  Come Closer, I Don’t Bite, Unless You Do Enjoy It😉   View My Private Pictures -  If you’re looking  to mess around… I don’t know, maybe in a way that’s a bit spicy for the  two of us? I’m a trans beauty with a dirty mind and I love...

Your Shemale Addiction 😈🥵 Starts Now Shemale Seeking Male.. Your Fantasy Starts Here 24yr old Transsexual/Shemale in Milwaukee 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...

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 at BlancaShemale32 for my latest pictures and proof of my size!&n...

Milwaukee 😈🍆💦 Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking 🔥Ready to Fulfill Your Wildest Fantasies  My Spicy Latina Shemale Pix! -Are you looking for a sexy shemale to play with? I'm a bit of a drama queen. I love dressing pretty and getting my nails done. I will also dress sexy in lingerie for you. Do you want to have a hoo...

I Need a Sexy Man to Tame Wild Willy! Hung Milwaukee Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Milwaukee 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...

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 masseur, hot body and hung. If you want to get together, Send me a private message Crystal27trans <3 ...

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! ...

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...

Local Crossdresser 😉😇 LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Milwaukee View My Personal Pix - 🤫  A sexy Crossdresser from Milwaukee, here, and her name is  KaralynnCD. I am pre-op but that has not stopped me from enjoying all the benefits that come with being  a Crossdressing Trans woman. If you like dirty gam...

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...

I'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 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 Shemale in Milwaukee Ready to Fulfill Your Wildest Fantasies 👄💦🍆 I'm TS and Looking to Date in Milwaukee My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Milwaukee who knows how to have a good time? Look no further, because I'm here to make all your dreams come true. I'm really excited about possibly meeting some like minded people and h...

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!&...

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...

Milwaukee, Wisconsin Area 🍆 Shemale Seeking Male  Hot and kinky shemales available in Wisconsin; I am Alane and  I am here to fulfill all your desires. If you are in Milwaukee, Wisconsin and  looking for a hot and kinky shemale to fulfill all your desires, then look no further for me. 🙂 More about me...  All kinds of sexual...

Milwaukee's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Milwaukee Hi you sexy man! I'm Toni a trans woman from here in Milwaukee. 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...

She-male looking for hot date to please. Asian Shemale in the Milwaukee 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...

INTERACTIVE MAP: Transexual Tracker in the Milwaukee Area! Local Transexual Hookups Meet local transexuals in the Milwaukee area. View our interactive map below to meet local trans hookup members who are seeking dating or sex hook ups. Click any thumbnail below to begin your search. Interactive Milwaukee Trans Hookups Map ...

YOUR EBONY SHEMALE - big boobs and a BIG COCK! Milwaukee Hot Hot Hot! Sinead, a black shemale in Milwaukee ready to make all of your  wildest fantasies come true! 💋🔥 My Pictures and Profile! -- You want to find a sexy ebony shemale in  Milwaukeeto fulfill all your dreams? Then stop searching because I am ready to make  all of your d...

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...

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...

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...

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 ...

💖 Discreet, Naughty & Waiting for a Man Who Can Handle Me  🔥 I’m an exotic ebony TS bombshell in Milwaukee 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...

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 and send message for date....

BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK 🍆😉 BBC SHEMALE - BLACK TRANS💎 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...

Sexy Shemale Milwaukee 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 Milwaukee; 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...

New Body New Me M2F post-op in Milwaukee 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...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Milwaukee 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...

Tantalizing Tina with a HUGE W33NAH! Milwaukee Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Milwaukee 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...

TS Beauties—Let’s Have Some REAL Fun! 😏🔥  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. 💋 Must  have confidence, charm...

Dr 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 Milwaukee 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? 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...

Sexy hung and big busted Hung and Busty Shemale in Milwaukee 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....

I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Milwaukee ) Sexy Crossdresser Elissa Looking for Hot Fun in Milwaukee💋    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...

I 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 Milwaukee area. Click here and come see me anytime!...

MALE SEEKING SHEMALE 🍆Milwaukee Ready to Play and Fuck 💦 I have a secret.. 🤫 I've always want to see what it's like to play with a shemale!!  Hi I'm John, I'm in Milwaukee  and I love to be free and have fun.. Are you looking for a man who really knows how to treat you?? I really want to show you what I got sweetie. I have a good heart ...

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...

F/M seeking love and fun Female to Male Trans Man in Milwaukee 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...

Flawlessly gorgeous trans bombshell in Milwaukee Trans MtF for Man in Milwaukee 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 5 feet 7 and have deep blue eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned! Send your...

TS Beauties—Let’s Make Some Memories 💖✨  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...

TS Latina Fantasy Girl – Let Me Rock Your World 💋🔥  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...