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 9th, 2025
  • TS Latina Goddess – For Men Who Crave Passion, Fire & Pleasure πŸ”₯πŸ’‹TS Latina Goddess – For Men Who Crave Passion, Fire & Pleasure πŸ”₯πŸ’‹  Hello sweetheart 😘 The TS Latina bombshell body type defines me through my soft lips and thick  thighs and my hidden surprise under red lace. Your pleasure stands as my life purpose because I want to  satisfy your desires and make your body experience intense pleasure through my s...
  • 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  ...
  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Milwaukee Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Milwaukee 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...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Milwaukee. 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...
  • 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 Milwaukee tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer th...
  • 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 M...
  • 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....
  • DonDon'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...
  • Shemale 4 Men πŸ†πŸ’¦  Milwaukee Ready Now!! Shemale 4 Men πŸ†πŸ’¦ Milwaukee Ready Now!!  Come Closer, I Don’t Bite, Unless You Do Enjoy ItπŸ˜‰   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...
  • F/M seeking love and funF/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...
  • 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...
  • MALE SEEKING SHEMALE πŸ†Milwaukee Ready to Play and Fuck πŸ’¦MALE SEEKING SHEMALE πŸ†Milwaukee Ready to Play and Fuck πŸ’¦ 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 ...
  • Spicy and Hot T-Girl from ColombiaSpicy 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...
  • TS Latina Snack – Sweet Like Sugar, Dirty Like Tequila 😘🍹TS Latina Snack – Sweet Like Sugar, Dirty Like Tequila 😘🍹  You can find me at the bar where I serve drinks and flirt with customers while enjoying the  atmosphere. I’m your sexy little TS Latina snack — soft lips, juicy thighs, and a tongue that  doesn’t stop until you beg me to πŸ’‹ I’ll start off sweet, flirty, &nbs...
  • 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 Milwaukee area and are interested then drop me a line and introduce yourself. You ca...
  • Elisabeth waiting to be your QueenElisabeth 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! Private Messag...
  • DonDon'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...
  • 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 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 ...
  • Milwaukee, Wisconsin Area πŸ† Shemale Seeking MaleMilwaukee, Wisconsin Area πŸ† 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. πŸ™‚ More about me...  All kinds of sexual...
  • Superb Shemale in Milwaukee...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 ...
  • Sexy hung and big bustedSexy 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....
  • 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 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...
  • 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 Milwaukee area. Click here and come see me anytime!...
  • I’m a Sexy and Naughty T-Girl Here in Milwaukee.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...
  • 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...
  • TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘  Papi… I’ve been thinking about you 😘 View More Sexy TS PIX - My curvy figure and thick TS  Latina body has caramel skin while my filthy mind and mouth were made for you 😈. I become  submissive only when you want me to submit while I transform into a dominant forc...
  • New Body New MeNew 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...
  • II'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...
  • Local Crossdresser πŸ˜‰πŸ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser πŸ˜‰πŸ˜‡ 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...
  • 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...
  • 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 ...
  • πŸ’¦ Thick, Juicy & Kinky – Come Experience the Best πŸ˜πŸ’¦ Thick, Juicy & Kinky – Come Experience the Best 😏  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 ...
  • 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 Milwaukee area come see if you measure up! Click here for explicit photos. Look...
  • Hot Shemale in Milwaukee Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ†Hot Shemale in Milwaukee Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ† 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...
  • 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 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...
  • Seeking All TS Beauties in MilwaukeeSeeking All TS Beauties in Milwaukee  I am a masculine, dominant, and very passionate man, and I am looking for a sensual  and seductive TS woman to explore our deepest desires together. No matter whether you like to be the  boss or to be taken care of, I am all about creating electric chemistry and unforgettable moments...
  • INTERACTIVE MAP: Transexual Tracker in the Milwaukee Area!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 ...
  • Milwaukee πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Milwaukee πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking πŸ”₯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...
  • 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 Milwaukee 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...
  • Shy Transexual Escort inΒ MilwaukeeShy Transexual Escort inΒ 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 ...
  • Trans Man waiting for right date with hot beautyTrans 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!&...
  • Tainted Love - Beyond Compare!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...
  • TS m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Milwaukee 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...
  • 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....
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! MilwaukeeYOUR 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! πŸ’‹πŸ”₯ 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...
  • Sexy Shemale Milwaukee I know You Want to Play 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...
  • April 8th, 2025
  • 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...
  • 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 Milwaukee 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...
  • Superior Massage by gorgeous T-GirlSuperior 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...
  • Spicy 🌢  Latina Shemale in Milwaukee Ready to Fill You πŸ˜‰πŸ˜‰ Spicy 🌢 Latina Shemale in Milwaukee Ready to Fill You πŸ˜‰πŸ˜‰ LATINA SHEMALE SEEKING πŸ”₯🌢  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Milwaukee.  Don't look any further, because I'm here to make all your wet dreams come true. My name is MARIA TS and I am a pre-op transgender woman who loves...