Annapolis, Maryland Shemale Dating Classifieds

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  • September 20th, 2026
  • II'm a Horny Shemale πŸ˜ˆπŸ’‹ Looking For Sex Tonight!! Sexy ShemaleπŸ’Ž Ready to Rock Your World! Local Transsexual - TGIRL Sext App πŸ“² I'm a Transgender and I'm looking for a naughty man with a nice cock here in near me.. Who is wanting to share some sexy fun with me. I've been really horny and hard!! I love taking cock and giving it, what are...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Annapolis 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...
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! AnnapolisYOUR EBONY SHEMALE - big boobs and a BIG COCK! Annapolis Hot Hot Hot! Sinead, a black shemale in Annapolis 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  Annapolisto fulfill all your dreams? Then stop searching because I am ready to make  all of your d...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Annapolis 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....
  • FtM seeking Princess Bride in AnnapolisFtM seeking Princess Bride in Annapolis FtM seeking Woman in Annapolis Hi, I'm Andy, age 33, FtM transgender man living in Annapolis. 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...
  • 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 Fantasy Girl – Let Me Rock Your World πŸ’‹πŸ”₯TS Latina Fantasy Girl – Let Me Rock Your World πŸ’‹πŸ”₯  Mira, papi… I’m not just sexy — I’m dangerous 😘 ( View My Dating Pictures Here ) My  TS Latina body features silky skin and long hair and full lips and a tight and juicy physique. I  dress to kill. My moans produce musical sounds. My movements flow throug...
  • 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 Annapolis area come see if you measure up! Click here for explicit photos. Look...
  • I’m a Sexy and Naughty T-Girl Here in Annapolis.I’m a Sexy and Naughty T-Girl Here in Annapolis. Annapolis T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Annapolis 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...
  • Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯  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...
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  • She-male looking for hot date to please. She-male looking for hot date to please. Asian Shemale in the Annapolis 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 com...
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Annapolis Look no further honey, I'm Franny an Ebony trans woman here in Annapolis 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...
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  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Annapolis Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Annapolis 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...
  • Sassy CD Looking for a Real Man 😘πŸ”₯Sassy CD Looking for a Real Man 😘πŸ”₯  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...
  • 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 ...
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Annapolis who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all in it...
  • Free Maryland Transexuals GuideFree Maryland Transexuals Guide Maryland Transexuals Guide The Maryland Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free Maryland Transexuals Guide online.  Where to Meet Transexuals in Mary...
  • Flirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆFlirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆ  I’m a sexy, smooth, and playful crossdresser who enjoys the attention, desiring  to be treated like a lady. Seeking for a man who can appreciate a well dressed CD for a  casual fun night or even something ongoing. I am a pleaser and I want to be pleased.  πŸ’‹ πŸ’Ž Bath g...
  • THE RIGHT GUY FOR THE JOB!!!THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! πŸ˜‰ 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...
  • 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....
  • Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹  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...
  • Let’s Get a Drink… and See Where It Leads 😘Let’s Get a Drink… and See Where It Leads 😘  One Night, No Limits...  AnnapolisShemale Seeking Man for sexπŸ’¦ View More of My Pix - βœ… 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 s...
  • 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 Annapolis 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...
  • Superb Shemale in Annapolis...Superb Shemale in Annapolis... T-Girl for NSA Encounters in Annapolis When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Annapolis. 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 ...
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Annapolis Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Annapolis 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 m...
  • 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 Annapolis 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...
  • September 19th, 2026
  • Flirty, Dirty, and Ready for Some Fun ❀️ Annapolis Shemale Seeking Male Flirty, Dirty, and Ready for Some Fun ❀️ Annapolis 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...
  • TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘  Hola, mi amor 😘 The fiery, curvaceous TS Latina body I possess was  made for lust while my soul demands intense passionate nights. Your dream woman has arrived because I possess caramel  skin and thick thighs and long hair and soft lips and a throbbing surprise between my legs th...
  • Looking for a TS Woman Who Loves to Be Desired πŸ’¦πŸ”₯ AnnapolisLooking for a TS Woman Who Loves to Be Desired πŸ’¦πŸ”₯ Annapolis  Male Seeking Transsexual for fun and whatever else!! I am a charming, confident and masculine guy and I have a special interest in beautiful TS  women. I would be happy to meet anyone who wants to have fun, enjoy and indulge in the  process. πŸ’‹ I would love to meet a shemale or tra...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy \ Annapolis!HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Annapolis! 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 Annapolis!  No strings - just great times, so join my page free for instant access! Shemale Gia's Annapolis Sexbook @ShemaleGia27 Photos: 4...
  • πŸ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & PleasureπŸ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure  πŸ‘‘ 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...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Annapolis Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • Marina TS πŸ† Visiting and ReadyMarina TS πŸ† Visiting and Ready Visitng Houston, Texas - Your TGirl Escort Hi guys Marina TS visiting your city …. We can start a sexy friendship, but if you are generous, it would not be bad. Please call me and text me when you are ready....MESSAGE ME HERE. Sexy, latina, femenine and beatiful TS woman here. English/e...
  • 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...
  • Hot TS Latina with Curves, Sass, and a Thirst for You 😘🍷Hot TS Latina with Curves, Sass, and a Thirst for You 😘🍷  You are not the typical girl who lives in the next house… You are the woman who occupies  your thoughts when you are with the woman who lives next door.  Message me here!! I’m a TS Latina goddess —  I have the shape of a coke bottle, the lips of sin, and a t...
  • Ebony Shemale in Annapolis ❀️😘 Seeking Male for Naughty Fun!Ebony Shemale in Annapolis ❀️😘 Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies πŸ’‹ Are you looking for a hot and kinky black shemale in Annapolis? 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 p...
  • Your Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ AnnapolisYour Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ Annapolis I am a  hot, cool and confident crossdresser who enjoys the feeling of being wanted, loved and taken care  of like a lady. Whether you are looking for some hot action, a nice relationship or even a  friend with benefits, I am here to make it unforgettable. πŸ’‹ πŸ‘  Feminine, fun and ...
  • πŸ‘  Classy on the Streets, Naughty in the Sheets – Let’s Play πŸ’‹πŸ‘  Classy on the Streets, Naughty in the Sheets – Let’s Play πŸ’‹  πŸ’– 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...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Annapolis? 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...
  • 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....
  • Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates.Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Annapolis Area Hi, my fem name is Gloria. I'm a married crossdresser in the Annapolis 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 dressin...
  • 🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘 πŸ’– Hey, Handsome! I’m a sultry, curvy ebony TS  here in Annapolis... I'm Pre Op, ready to play, with a body made for pleasure and a heart full of passion. Discreet, sensual, and looking for a man who knows how to handle me. Let’s make tonight unforgettable! 😘 I'm writing this t...
  • Beautiful Krystale 25 Annapolis visiting nowBeautiful Krystale 25 Annapolis visiting now Beautiful Shemale Visiting Annapolis 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: Annapolis Sex: Shemale Seeking: Man ...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Annapolis 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!&...
  • 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...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Annapolis 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....
  • One Night, No Rules, Just Pleasure… One Night, No Rules, Just Pleasure… Annapolis I'm Having a Night to Myself No Strings, just fun.. TS Seeking...🀫  A man who knows what he wants, but also a man who can be tempted, that’s  what I like.  We should begin with eye contact, a slow touch, and perhaps truth or  dare while drinking cocktails...
  • TS Latina Dream Girl – Ride Me Like a Telenovela πŸ˜ˆπŸ“ΊTS Latina Dream Girl – Ride Me Like a Telenovela πŸ˜ˆπŸ“Ί  Have you ever imagined a sensual Latina woman with large thighs and a narrow waist and a hidden sexual  secret? That’s me, papi 😘 I’m your spicy TS novela — dramatic,  passionate, and unforgettable in the bedroom. Message me here babe - I want your hands on my h...