Southern MD, Maryland Shemale Dating Classifieds

Southern MD, Maryland 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!

Home / Shemale Dating /

Show Ads In: Annapolis | Baltimore | Eastern Shore | MD suburbs of DC | Southern MD | Western MD

June 3rd, 2025

Penny for your thoughts? Penny TS in Southern MD 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 ...

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 Southern MD 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 live...

Southern MD Addicted to shemales... Male Seeking TS  A handsome, fit and confident man, seeking a stunning TS girl to spend exciting nights and incredible  moments with. I have a thing for flirty conversations, passionate chemistry and playful antics- if you  are looking for a casual meet or if we can make this a more regular thing, I ...

Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Southern MD 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...

I love a confident, seductive TS woman—could you be the one? 💋  A handsome, intelligent and adventurous man, here looking to meet a gorgeous TS woman to have  excitement, chemistry and wild nights. I just love confident women who know what they want and I’m more  than ready to spoil, explore and indulge in pleasure together.  Handsome,...

👑 Chocolate Queen with Soft Curves & Naughty Desires 🔥  🔥| 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 ...

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

TS Latina Seductress – Thick, Wet & Ready to Be Used 💋🍑  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 Me M2F post-op in Southern MD 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 Nat...

M-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....

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...

Sassy CD Looking for a Real Man 😘🔥  A sweet, sexy and a little naughty crossdresser here, I like to play and  flirt, and I need a strong man who knows what he wants. I enjoy the process of dressing  up, teasing and bringing fantasies to life. If you are into sensual encounters and passionate fun then let me  and y...

👄 Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure  👑 I am the Queen of Your Fantasies – Come Worship Me! I am  a gorgeous, confident, ebony TS, with a body built for pleasure and a mind full of naughty  ideas. If you are looking for high class experience, filled with deep pleasure, seductive touches and  sensual moments...

INTERACTIVE MAP: Transexual Tracker in the Southern MD Area! Local Transexual Hookups Meet local transexuals in the Southern MD 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 Southern MD Trans Hookups Map ...

Tainted Love - Beyond Compare! Kinky Trans Woman in Southern MD Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Southern MD. 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 appreciat...

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 Southern MD area and are interested then drop me a line and introduce yourself. You ...

HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Southern MD! 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 Southern MD!  No strings - just great times, so join my page free for instant access! Shemale Gia's Southern MD Sexbook @ShemaleGia27 Photo...

British T-girl Seeking Classy Gentleman in Southern MD... 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 Southern MD and am financially independent and looking for a gentleman who is like-minded, equally solvent and has ex...

Local Crossdresser 😉😇 LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Southern MD View My Personal Pix - 🤫  A sexy Crossdresser from Southern MD, 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...

Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Southern MD 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 insert...

Well Endowed Shemale is beautiful Southern MD 32 Well Endowed Shemale in Southern MD 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!...

She-male looking for hot date to please. Asian Shemale in the Southern MD 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 c...

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

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 ...

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

Southern MD 😈🍆💦 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...

Flirty, Dirty, and Ready for Some Fun ❤️ Southern MD Shemale Seeking Male Local Shemale Seeks Man For Adventure!  TS Vixen, are you ready to play? Sweet, sultry and a little bit  wild, I am a trans goddess and I do enjoy my men to be as much as a wild  as I am. 😘I don’t want to talk – I want to try something a bit  more exciting. How ab...

Seeking a Stunning TS for Passion & Pleasure 😘🔥  I am a confident, strong and open minded man, who knows what I want from a woman  – a sexy, elegant and fun loving TS woman to share unforgettable moments with. I am here to  explore and enjoy every second of it, whether it is a casual hookup, a fun date or a  deep connect...

Let’s Play a Game—Winner Gets Me 😉 Southern MD 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 Shemale in Southern MD Ready to Fulfill Your Wildest Fantasies 👄💦🍆 I'm TS and Looking to Date in Southern MD My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Southern MD 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 a...

SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Southern MD Secret Crossdressing Hookups in Southern MD 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...

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

Email Local Shemales Now! 💌 Want to Hookup and Find Local 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'reinterested in 😉.. Do you want to meet local shemales who want to fuck and have some sex...

I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Southern MD I'm queen Delilah a trans woman here in Southern MD 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 ...

MALE SEEKING SHEMALE 🍆Southern MD 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 Southern MD  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 hear...

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...

Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Southern MD Look no further honey, I'm Franny an Ebony trans woman here in Southern MD 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 ...

June 2nd, 2025

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

Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Southern MD 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 ...

Sexy hung and big busted Hung and Busty Shemale in Southern MD 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....

THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! 😉 My name is Frank and I'm here to see if I can find any transgender ladies who wants a real man to treat them right.. I'm living in xxxx but I'm willing to travel. I have a great house we can have some fun in as well. I have a HOTTUB, arcade, th...

Looking for My TS Queen 👑💋 I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. 💕 I appreciate a woman who knows her worth and loves to be treated right. Whether it’s a romantic dinner, steamy nights, or spontaneous adventures,...

Erotic exotic Asian queen in Southern MD now (25) Asian Transexual in Southern MD Stunning TS - Talia 25. 5' 8" 140lbs, non op, loves sex. Long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information....

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  ...

Beautiful Krystale 25 Southern MD visiting now Beautiful Shemale Visiting Southern MD 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: Southern MD Sex: Shemale Seeking: Man ...

Ebony Shemale in Southern MD ❤️😘 Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies 💋 Are you looking for a hot and kinky black shemale in Southern MD? Look no further because I am here to satisfy all your desires. My name is StefanieBBC and I'm an Ebony Shemale..  I am a stunning transgender woman who loves to...

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Southern MD 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 Mess...

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

💦 Thick, Juicy & Kinky – Come Experience the Best 😏  🔥| 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 ...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Southern MD 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: Gayl...