Maryland Transgender Classifieds

Browse Maryland transgender classifieds to meet local transexuals, crossdressers and shemales for sex, dating or friendship. Contact any of these trans advertisers to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all trans classifieds, or post your own adult ad!

Home / Dating / Transgender

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

April 5th, 2025

Ebony TS Playmate for Men Who Know What They Want 🖤🍆  If you are the type of person who does not want to waste time with games or small  talk… we are already off to a good start 😘 I am a sexy, curvy TS  babe who loves attention, loves giving pleasure, and lives to be desired. I will come looking like  a dream and be read...

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

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

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...

Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Maryland Area Hi, my fem name is Gloria. I'm a married crossdresser in the Maryland area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but wife doesn't approve. I really need to let my fem side out to play! I'm seeking cross dressing ...

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...

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 ...

Well Endowed Shemale is beautiful Maryland 32 Well Endowed Shemale in Maryland 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!&nb...

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...

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...

Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Maryland 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!&n...

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

April 4th, 2025

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...

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 ...

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...

Debonair Trans dude, looks like Bond F2M Trans Dude in Maryland 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.&...

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....

HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Maryland! 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 Maryland!  No strings - just great times, so join my page free for instant access! Shemale Gia's Maryland Sexbook @ShemaleGia27 Photos: 42 ...

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

Black/Ebony Transsexual - Your New Addiction – One Taste and You’ll Beg for More 🍑💋  Warning: I’m addictive 😘 View My Ebony TS Profile here - I possess more than attractive features. I am a complete  TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and  thick thighs and soft lips and a hidden secret th...

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...

Email Maryland Shemales❤️‍🔥 I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...

Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Maryland? Hey, I am Jasmin, 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...

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...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Maryland I will help you unwind and create a cozy environment for you! I am hot and sweet and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl Gayle 😍 Transgender World Profile Username: GayleTGirl Locat...

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

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...

Road Head Sally Drivin' Hard in Maryland Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Maryland. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or par...

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...

Brandi 27 tall slim hot trans chick fully functional 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 big functioning ladyclit for top or bottom. I love oral sex!! Kink friendly, have toys to explore all y...

TS Temptress Ready to Ruin You (In the Best Way) 😈💦 Maryland  Hey lover 😘 I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...

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

Latina TS Dirty Girl Looking for a Gentleman's Dark Side 🔥👠  Sweet on the surface. Filthy underneath. View My Trassexual Dating Profile Here - As a TS darling I present like a dream while  playing like a fantasy. Stockings. Heels. A tight dress. Soft skin. And a  throbbing surprise you’ll love exploring 😘 I need you to undress me gr...

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...

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...

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Maryland 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 Message...

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 ...

April 3rd, 2025

Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Maryland for Man Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will be p...

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....

Hot trans chick with nice boobs Hot trans chick in Maryland. 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...

Having 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....

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 ...

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...

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....

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

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  ...

New Body New Me M2F post-op in Maryland 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 Natash...

Strict Shemale Dominatrix in Maryland - @DesireeTransDomme Powerful African-Queen Dominatrix in Maryland I am full-time professional Domme Desiree. My Maryland area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will learn ...

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...

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!...