Milwaukee Transgender Sex Ads

Browse Milwaukee transgender sex ads to meet local transexuals, crossdressers and shemales for sex, dating or friendship. It's free to search the trans sex classifieds, or post your own adult ad!

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September 7th, 2025

Spark Up Some Chemistry with Anjela Hey there! I'm Anjela, a transgender woman from Milwaukee, Wisconsin. I may not fit society's standards of beauty, but I embrace my uniqueness and love every bit of myself. Being part of the LGBTQ community has brought so much joy and acceptance into my life, and I wouldn't have it any other way. ...

Hot Shemale Aubree Looking for a Milwaukee Man to Fuck and Suck All Night Long Are you ready for a wild night of passion with a sexy shemale like me? My name is Aubree, and I am looking for a local man in Milwaukee who can handle all of my naughty desires. I love being both a top and bottom, so we can switch things up and have some real fun together. Whether you want to suck...

Spark the Flame of Passion with Kylie from Milwaukee! Hey there! I'm Kylie, a fun-loving transgender gal from Milwaukee, Wisconsin. I may not fit society's norms, but that's what makes me unique and fabulous! I embrace my LGBTQ identity and love connecting with open-minded individuals who appreciate diversity. I enjoy exploring new places in Cream C...

Transgender Beauty Seeking Connection in Milwaukee! Hey there, lovely people of Milwaukee! My name is Ashleigh, and I'm a transgender individual who's ready to embrace life and find someone special to share it with. 💖 As a proud member of the LGBTQ community, I've come to appreciate the beauty of diversity and the strength that comes from being...

Hot Shemale Nicolle Looking for Naughty Fun in Milwaukee! I'm a sexy shemale named Nicolle who's on the hunt for a local man to have some wild and kinky fun with. I love being both top and bottom, so you can expect a truly versatile experience with me. Whether you want to suck my throbbing cock or ride me until we both explode with orgasms, I'm game for ...

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! Private Messag...

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!&...

Elegantly Confident Trans Beauty Ready for Romance Hey there, I'm Beverie from Milwaukee, Wisconsin. As a proud transgender woman, I embrace my uniqueness and love being part of the LGBTQ community. I enjoy exploring new places in the city like Lakefront Brewery, Bradford Beach, or even catching a show at The Pabst Theater. I'm looking for someo...

TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Milwaukee Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...

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...

SHEMALE HOOKUPS! Wanna Have a Great Time in Milwaukee, Wisconsin? HOT!  SHEMALE HOOKUPS  "The girl with a naughty little secret in her panties!" SIGNUP FREE: INSTANT ACCESS!  Shemale Profiles Browse Uncensored Photos, Swap Your Pics, Join Live Web Cams, Swap Private Messages, Sext & Hook Up! Join free for Instant Access to the Milw...

HMU for Sex in Milwaukee Newly Single and Ready to Mingle in Milwaukee Hi guys, my name is Barbie, age 28. My husband cheated for the last time. Now it's my time to have some fun! If you want to hook up for passion and hot sex in the Milwaukee, Wisconsin area then message me @BarbieSingle28.      ...

Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖 Preop Trans in Milwaukee Hi! I'm Brandi, new TS in the Milwaukee area. I'm MtF preop transexual woman. I pass as female very well so we can go to your business function or out for dinner followed by a night of forbidden fun that only we will know about! I am fully functional, 8" thick hiding in my ...

Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Milwaukee? Hey, I am Jasmin, 8" with a great body and busty. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for hot dates and see where it goes!  Hit me up @SweetJasminT...

Raunchy Shemale Seeking Local Man for Wild Fun Looking for a man who can handle a naughty shemale like me? Well, you're in luck! I'm Mariellen from Milwaukee, Wisconsin, and I'm ready to show you a good time. I love getting down and dirty with a guy who knows how to please me in all the right ways. From sucking and fucking to gagging and ridin...

Well Endowed Shemale for Man in Milwaukee Hung Shemale for Man in Milwaukee I am Blanca. I can provide top or bottom service. Bareback if you're clean. Love oral sex both giving and receiving. Say hello cause I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me privately at BlancaShemale32 for my latest uncen...

Naughty Shemale Tiffie Seeking Hot Milwaukee Man for Wild Fun Looking for a local guy who can handle a sexy shemale like me, Tiffie. I love getting down and dirty, so if you're into some raunchy action, I'm your girl... or should I say, shemale! 😈 I enjoy everything from deepthroating your throbbing cock to riding you like a wild stallion. Let's play wit...

Spark the Flame with Kelsy Hey there! I'm Kelsy, a fun-loving transgender gal from Milwaukee, Wisconsin. I may not fit into society's typical mold, but that's what makes me unique and special. I embrace my LGBTQ identity and all the beauty that comes with it. 💖 I'm looking for someone who is open-minded, adventurous, an...

Raunchy Shemale Seeking Hot Man for Wild Fun in Milwaukee I love getting down and dirty with a man who can handle all that I have to offer. My name is Sarajane, and I am a shemale looking for a local guy who wants to explore all of his wildest fantasies with me. From top to bottom, I'm ready to play and make you cum like never before. I enjoy giving sl...

Tempting Transgender looking for Love in Milwaukee Hey there, I'm Rubi from Milwaukee, Wisconsin. I'm a curvy Latina beauty who loves exploring the city and trying new things. As a transgender woman, I embrace my identity and love being part of the LGBTQ community. I enjoy long walks by Lake Michigan, sipping coffee at Colectivo Coffee, and danc...

Shemale Nightclubs Near You in Milwaukee, Wisconsin Shemale Nightclubs Near You in Milwaukee, Wisconsin Shemale Clubs Near You in Milwaukee, Wisconsin is a directory of trans-friendly nightclubs and bars. LGBTQ+ clubs come and go. We strive to keep this transgender clubs directory complete and rely on your input to help us do so. Please contact us...

INTERACTIVE MAP: Transexual Tracker in the Milwaukee Area! Local Trans Hookups Interactive Mapping Meet Local transexuals in the Milwaukee area for friendship or sex hookups. View member thumbnails on the interactive map below to meet local members who want to meet local transexuals or admirers. Click any member photo below to get started. Sign up free for...

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...

TS M2F Top in Milwaukee TS Top Seeking Man in Milwaukee I'm Sandi wants to meet hot guy for fun and hot sex. Age 28 with long blonde hair, smooth skin and a great body.  Non op functional, nice big ladystick for your pleasure! 😈  Love oral sex, anal sex and yummy kinks of all sorts. I love to explore kinks an...

September 6th, 2025

27 y/o Sexy Hung Crossdresser in Milwaukee Hung Crossdresser for Male in Milwaukee Hey, I go by Selena when I'm cross dressed. I love being feminine and servicing my man!, I'm age 27, well hung and so cute when I'm dressed up!! What more could you want in a gurl?!! View my pics and message me @Selena27femCD so we can talk and meet for a sex...

A Sensual Journey: Seeking Connection Hey there, I'm Sharl from Milwaukee, Wisconsin. I'm a curvy and confident transgender woman who loves exploring the vibrant LGBTQ community in our city. Whether it's grabbing a coffee at Colectivo Coffee, taking a stroll through Lake Park, or catching a show at the Pabst Theater, I'm always up for...

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 naughty f...

Gorgeous, Passable Trans in Milwaukee 😍 Gorgeous Passable Trans MtF for Man in Milwaukee 😍 I transitioned 6 years ago at age 18. I am pretty, with long light brown hair, a nice figure and long shapely legs. I have brown puppy dog eyes and kissable lips. Check my profile @TransFaye24 for pics and prepare to be stunned!  I'm ...

Hot Shemale in Milwaukee Looking to Fuck and Suck Are you looking for a shemale who knows how to have a good time? Look no further, because I'm Meg and I'm ready to play! I love being both top and bottom, giving blowjobs, getting my tight ass fucked, and making you cum hard. Whether you want a sloppy blowjob or a deep anal ride, I'm your girl. M...

Debonair Trans dude, looks like Bond F2M Trans Dude in Milwaukee 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....

Tempting Transgender in Milwaukee Hey there, I'm Riane from Milwaukee, Wisconsin. I'm a curvy Latina beauty who loves embracing my transgender identity. Being part of the LGBTQ community brings so much joy and excitement to my life. I enjoy exploring new places in the city like Lakefront Brewery, Bradford Beach, or even catching a...

A Night of Magic and Connection 💫 Hey there! I'm Lucina, a proud transgender woman from Milwaukee, Wisconsin. I may not fit society's norms, but I am confident in my own skin and love embracing my true self. Being part of the LGBTQ community has brought me so much joy and empowerment. I'm looking for someone who is open-minded, k...

Raunchy Shemale Seeking Local Man for Hot Encounters Are you ready to experience the wildest night of your life? I'm Sarena, a horny shemale from Milwaukee looking for a man who can handle all my desires. I love getting down and dirty, so if you're into some kinky fun, I'm your girl... or should I say, your shemale! I enjoy being both a top and a b...

Spark the Flame: Transgender Beauty in Milwaukee Hey there, I'm Leelah from Milwaukee, Wisconsin. I may not fit society's idea of "normal," but that's what makes me unique and beautiful. Being transgender allows me to explore different aspects of my identity and express myself in ways that feel authentic and true. 🌈 I'm looking for someone w...

Spark Up Your Life with Rani! Hey there! I'm Rani, a transgender cutie from Milwaukee, Wisconsin. I may not fit society's standards of beauty, but my confidence and charm will sweep you off your feet. 💃🏽 I love being part of the LGBTQ community because it's a place where I can truly be myself without any judgment. 🏳�...

Seeking Connection in Brew City Hey there, I'm Deanna from Milwaukee, Wisconsin. I'm a proud transgender woman who loves embracing my true self and being part of the LGBTQ community. I enjoy exploring new places in the city, trying out different cuisines at spots like Odd Duck or Comet Cafe, and taking long walks along Lake Mich...

A Sparkling Connection Awaits You 💫 Hey there! I'm Cristal, a fun-loving transgender gal from Milwaukee, Wisconsin. I may not fit society's mold, but that's what makes me unique and fabulous! 🌈 I enjoy exploring the city and checking out local spots like Lakefront Brewery, Bradford Beach, or even catching a game at Miller Park. ...

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...

Looking for Love and Adventure! Hey there! My name is Margaret, and I'm a transgender woman living in beautiful Milwaukee, Wisconsin. 🌆 I wanted to take a moment to tell you a bit about myself and what I'm looking for. Physically, I have a curvy figure that's just right for cuddling up with on those chilly Wisconsin nights. ...

Elegantly Transgender Seeking Connection Hey there, I'm Delores from Milwaukee, Wisconsin. I may not fit society's mold of what a transgender person should look like, but that's what makes me unique. I love being part of the LGBTQ community because it allows me to express my true self without fear of judgment. I'm looking for someone w...

FtM seeking Princess Bride in Milwaukee FtM seeking Woman in Milwaukee Hi, I'm Andy, age 33, FtM transgender man living in Milwaukee. 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...

Let's Dance Under the Milwaukee Moonlight Hey there, I'm Joyan, a fun-loving transgender woman from Milwaukee, Wisconsin. I may not fit society's norms, but that's what makes me unique! Being part of the LGBTQ community has taught me to embrace my true self and live authentically. I love exploring new places in Milwaukee like Lake Park,...

Seeking Connection in Brew City Hey there! I'm Paule, a fun-loving transgender gal from Milwaukee, Wisconsin. I may not fit society's norms, but that's what makes me unique and fabulous! 🌈 I love exploring the city and checking out local spots like Lakefront Brewery or the Milwaukee Art Museum. Let's grab a drink at Good City...

Elegantly Transcending Boundaries Hey there, I'm Carlena from Milwaukee, Wisconsin. I may not fit society's typical mold, but that's what makes me uniquely me. I enjoy embracing my transgender identity and being part of the LGBTQ community because it allows me to express myself authentically without fear of judgment. If you're someo...

Sexy Shemale Inna Looking for Hot Fun in Milwaukee I love getting down and dirty with a man who knows how to handle a hot shemale like me. My name is Inna, and I'm looking for a local guy who can keep up with my insatiable appetite for sex. Whether you're into wild role play, deepthroating blowjobs, or rough anal play, I'm ready to make all your f...

Transgender in Milwaukee seeks connection Hey there! My name is Marin and I'm a transgender person living in the wonderful city of Milwaukee, Wisconsin. 🌆 I wanted to take a moment to write this ad and put myself out there, hoping to find someone special who can appreciate me for who I am. Physically, I have a body that's curvy and v...

Hot Shemale Britte Looking for Local Man to Play With Are you looking for a naughty shemale to fulfill all your wildest fantasies? Look no further, because I'm here to make all your dreams come true. My name is Britte and I'm a sexy shemale from Milwaukee, Wisconsin seeking a local man for some hot and steamy fun. I love getting down and dirty with ...

Elegantly Transcendent Iris Seeks Connection in Milwaukee Hey there! I'm Iris, a proud transgender woman from Milwaukee, Wisconsin. I may not fit society's mold of what a woman should look like, but that's what makes me unique and beautiful. Being part of the LGBTQ community has allowed me to embrace my true self and live authentically. I love explorin...

Raunchy Shemale Looking for Fun in Milwaukee I love getting down and dirty with a man who knows how to handle a shemale like me. My name is Elmira, and I'm looking for a local guy who can keep up with my insatiable appetite for sex. I want someone who isn't afraid to explore all of my kinks and fantasies. From blowjobs to anal play, I'm game...

Spicy Hot 🌶 Tranny Girl from Colombia Latina Tranny Girl in Milwaukee Hey guys, I am Gabriella and I am looking for a longterm relationship with a gentleman who love sex as much as I do! I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery except breasts. I am smooth and clean, very femini...