Maryland Shemale Dating Classifieds

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

June 22nd, 2026

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...

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 💋 I’ll start off sweet, flirty, &nbs...

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

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 Maryland area. Click here and come see me anytime!...

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 Maryland 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 n...

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

Flawlessly gorgeous trans bombshell in Maryland Trans MtF for Man in Maryland 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 ...

I’m a Sexy and Naughty T-Girl Here in Maryland. Maryland T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Maryland 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 and ...

Tiffany Shelle - Your Maryland Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Maryland 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% functioni...

Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Maryland 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 naug...

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

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

Transgender🍆Hookup in Maryland TRANSSEXUAL HOOKUPSin Maryland🍆 message me Check My Profile and and Dm MeI'm a tgirl and I live in  Maryland.. I'm willing to travel for sex. As longas you love TRANSGENDERS and want to have some fun and sexy sex. I would loveto connect and see what you're into!!Have you ever hook...

Superb Shemale in Maryland... T-Girl for NSA Encounters in Maryland When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Maryland. 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 an...

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

Erotic exotic Asian queen in Maryland now (25) Asian Transexual in Maryland 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....

Don't Worry I Bite! Feisty redhead trans in Maryland 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 ...

💦 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 ...

TS m/f switch 28 new here TS m/f Switch in Maryland 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...

👠 Classy on the Streets, Naughty in the Sheets – Let’s Play 💋  💖 Just one taste and you’ll be addicted! I am a beautiful, funny TS,  a queen of color with a nice curvy body, beautiful eyes, and a touch that will drive  you crazy. I know what a man needs and how to make him satisfied and craving for more.  I am looking for a confide...

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

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

SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Maryland Secret Crossdressing Hookups in Maryland 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 ga...

Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Maryland and ready to meeup and hookup in LA tonight.. Let's hang out and have some super sexy fun!! I really need to get out and have some fun. Come check out MY PROFILE, browse my pix, videos and send me a message now.. L...

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....

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

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

👄 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...

Hot Shemale in Maryland Ready to Fulfill Your Wildest Fantasies 👄💦🍆 I'm TS and Looking to Date in Maryland My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Maryland 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 hav...

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

TS Bombshell Looking for a Man Who Can Keep Up! 💋 Maryland  Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun! View More of My Pictures 📸 Are you the sort of man who enjoys  just a touch of danger, a touch of excitement, and a lot of passion? I’m the  trans beauty you’ve been dreaming of — sexy...

Trans Playmate Sex Kitten... Ebony trans woman in Maryland 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 am...

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! ...

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....

Shemale 4 Men 🍆💦 Maryland 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...

Let’s Get a Drink… and See Where It Leads 😘  One Night, No Limits...  MarylandShemale Seeking Man for sex💦 View More of My Pix - ✅ Some nights are for breaking rules, for letting go, and  for indulging in pure pleasure.  I am a trans goddess with a wild side, and I  am looking for a man who wants to play. We sh...

Bet I Can Make You Say DAAYUM!... Wassup all my Baltimore boos! I'm Sharise an ebony trans woman gonna make you say Daayum over and over again baby! I got the skills honey if you got the time. I'm 5'8, 160 pounds, black t-girl, big package, functional, passible and gonna make you forget all your problems tonight. Looking for a regul...

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

Maryland 😈🍆💦 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 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,...

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 Maryland area come see if you measure up! Click here for explicit photos. Look ...

TS Latina Bombshell Craving a Real Man to Handle Her 🍑🔥  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...

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

MALE SEEKING SHEMALE 🍆Maryland 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 Maryland  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 a...

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 Maryland tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer tha...

Penny for your thoughts? Penny TS in Maryland 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 hit...

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 Maryland area and are interested then drop me a line and introduce yourself. You can...

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...

TS Latina Goddess – For Men Who Crave Passion, Fire & Pleasure 🔥💋  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...