Annapolis Transgender Sex Ads

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  • April 2nd, 2025
  • Superior Massage by gorgeous T-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Annapolis 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...
  • 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...
  • A Sensual Journey of Self-DiscoveryA Sensual Journey of Self-Discovery Hey there, I'm Alanna, a transgender woman from Annapolis, Maryland. I may not fit society's norms, but that's what makes me unique and beautiful. Embracing my true self has been the most empowering journey of my life. I love connecting with others who appreciate authenticity and diversity. I enj...
  • Gorgeous, Passable Trans in Annapolis 😍Gorgeous, Passable Trans in Annapolis 😍 Gorgeous Passable Trans MtF for Man in Annapolis 😍 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 ...
  • Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖 Preop Trans in Annapolis Hi! I'm Brandi, new TS in the Annapolis 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 ...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Are you ready to get down and dirty with a sexy shemale named Mimi? I'm looking for a man in Annapolis who can handle all my naughty desires. I love being both top and bottom, giving mind-blowing blowjobs, getting my tight ass pounded, and riding a throbbing cock until we both explode in ecstasy. ...
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Annapolis 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 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!&...
  • Spark Up Some Magic with MinaSpark Up Some Magic with Mina Hey there! I'm Mina, a proud transgender woman from Annapolis, Maryland. I may not fit society's standards of beauty, but my confidence shines through in everything I do. You can check out my pics at my personal profile page @minaa13258. I love being part of the LGBTQ community because it allows ...
  • Meet Maryland Transexuals Online: Live Chat, Member Profiles, Photo Swaps & Local Trans ClubsMeet Maryland Transexuals Online: Live Chat, Member Profiles, Photo Swaps & Local Trans Clubs Meet Maryland Transexuals Online!  Meet Maryland transexuals online at AmericanTransexuals.com. Our web development team includes transexual women and male trans admirers, so we have a unique understanding of transgender attraction. We have created an online community where you can meet Maryla...
  • Seeking a Connection in AnnapolisSeeking a Connection in Annapolis Hey there, I'm Cayla, a fun-loving transgender gal from Annapolis, Maryland. I may not fit society's standards of beauty, but I embrace my unique body type and love being part of the LGBTQ community. If you're looking for someone who is confident in their own skin and loves to explore new places, ...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Hey there, I'm a sexy shemale named Maxie looking for a hot guy in Annapolis who can handle all my dirty desires. If you're ready to get down and dirty, then I'm the one for you. I love getting down and dirty with a man who knows how to please me in all the right ways. I'm into everything from pass...
  • 27 y/o Sexy Hung Crossdresser in Annapolis27 y/o Sexy Hung Crossdresser in Annapolis Hung Crossdresser for Male in Annapolis 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...
  • 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...
  • SHEMALE HOOKUPS! Wanna Have a Great Time in Annapolis, Maryland? SHEMALE HOOKUPS! Wanna Have a Great Time in Annapolis, Maryland? 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 Anna...
  • INTERACTIVE MAP: Transexual Tracker in the Annapolis Area!INTERACTIVE MAP: Transexual Tracker in the Annapolis Area! Local Trans Hookups Interactive Mapping Meet Local transexuals in the Annapolis 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...
  • April 1st, 2025
  • Hot Shemale in Annapolis Ready to Play and FuckHot Shemale in Annapolis Ready to Play and Fuck I'm a horny shemale looking for a local man who can handle all my desires. My name is Alice, and I love nothing more than getting down and dirty with a sexy guy who knows how to please me. If you're into wild nights filled with pleasure, then I'm the one for you. I enjoy being both top and bottom...
  • Spark up some magic with me, Didi!Spark up some magic with me, Didi! Hey there, I'm Didi from Annapolis, Maryland. I'm a fun-loving transgender gal who enjoys exploring new places and meeting new people. I love being part of the LGBTQ community because it allows me to be my authentic self without any judgment. If you're looking for someone who is open-minded and fu...
  • Raunchy Shemale Looking for Hot Fun in AnnapolisRaunchy Shemale Looking for Hot Fun in Annapolis Are you ready to have the time of your life with a sexy shemale like me, Celeste? I'm looking for a local man who knows how to handle a tranny like me. I love getting down and dirty, so if you're into that too, we'll get along just fine. I'm into all sorts of kinky stuff, from giving sloppy blow...
  • Well Endowed Shemale for Man in AnnapolisWell Endowed Shemale for Man in Annapolis Hung Shemale for Man in Annapolis 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...
  • Elegantly Transgender in AnnapolisElegantly Transgender in Annapolis Hey there! I'm Verna, a proud transgender woman living in Annapolis, Maryland. I love being part of the LGBTQ community because it allows me to be my authentic self and connect with amazing people like you. If you're looking for someone who is genuine, kind-hearted, and loves to laugh, then I'm yo...
  • Elegant Enigma Seeking ConnectionElegant Enigma Seeking Connection Hey there! I'm Elizabet, a transgender woman from Annapolis, Maryland. I may not fit society's standards of beauty, but I embrace my unique body type and ethnicity with pride. Being LGBTQ has opened up a whole new world of experiences and connections for me, and I'm excited to see where this journ...
  • Transgender Cutie Seeking Connection in Annapolis!Transgender Cutie Seeking Connection in Annapolis! Hey there! I'm Lia, a fun-loving transgender woman from Annapolis, Maryland. 💃🏻✨ I may be petite, with a contagious smile that can light up any room. 🌟 My heritage is diverse, reflecting the beautiful melting pot of our nation. 🌈 You know what's great about being trans? It's embraci...
  • Erotic Temptation: Seeking Connection in AnnapolisErotic Temptation: Seeking Connection in Annapolis Hey there! I'm Mandy, a transgender woman from Annapolis, Maryland. I love embracing my true self and being part of the LGBTQ community. It's empowering to live authentically and connect with others who appreciate me for who I am. I'm looking for someone special to share fun times and meaningful ...
  • Eager to Explore: Transgender Trudi Seeks ConnectionEager to Explore: Transgender Trudi Seeks Connection Hey there! I'm Trudi, a transgender woman living in Annapolis, Maryland. I love embracing my true self and being part of the LGBTQ community. It's empowering to live authentically and connect with others who appreciate me for who I am. If you're open-minded, kind-hearted, and looking for a meaning...
  • 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....
  • Shemale Nightclubs Near You in Annapolis, MarylandShemale Nightclubs Near You in Annapolis, Maryland Shemale Nightclubs Near You in Annapolis, Maryland Shemale Clubs Near You in Annapolis, Maryland 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 i...
  • Hot Shemale in Annapolis Looking for a Wild Time!Hot Shemale in Annapolis Looking for a Wild Time! Hey there, I'm Audie, a sexy shemale in Annapolis looking for a local man who can handle all my desires. I love to be on top, bottom, give blowjobs, get my ass played with, and ride a throbbing cock until we both explode with orgasms. I'm into sloppy gagging and cum play too - the dirtier, the bette...
  • 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...
  • Looking for Love and Adventure!Looking for Love and Adventure! Hey there! My name is Cher, and I'm a transgender woman living in beautiful Annapolis, Maryland. 🌸 I may not have the body type of a supermodel, but I embrace my own unique curves and feel confident in my own skin. 💃🏻 As for my ethnicity and nationality, let's just say I'm a delightful m...
  • LetLet's Dance Under the Stars Together Hey there, I'm Lila from Annapolis, Maryland. I'm a curvy Latina beauty who loves embracing my transgender identity. Being part of the LGBTQ community brings so much joy and authenticity to my life. I enjoy exploring new places, trying different cuisines, and dancing the night away. I'm looking f...
  • Brandi 27 tall slim hot trans chick 8.5 inchBrandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Annapolis 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...
  • Sexy Shemale Looking for Hot Fun in Annapolis!Sexy Shemale Looking for Hot Fun in Annapolis! Are you ready to get down and dirty with a horny shemale? I'm Jorrie, a sexy tranny from Annapolis looking for a local man who can handle all my naughty desires. I love to be on top, bottom, give blowjobs, get my ass played with, suck dick, have intense orgasms, role play, ride cock, feel a huge t...
  • Elegantly Transgender Joana Looking for Love in AnnapolisElegantly Transgender Joana Looking for Love in Annapolis Hey there! I'm Joana, a transgender woman living in Annapolis, Maryland. I may not fit society's norms, but I embrace my uniqueness and love being part of the LGBTQ community. I enjoy exploring my city and trying out new restaurants like Iron Rooster or Vin 909 Wine Cafe. I'm looking for someone...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Hey boys, I'm Suzette, a hot shemale from Annapolis looking for a man who can handle all my naughty desires. I love getting down and dirty, so if you're into some kinky action, I'm your girl... err, shemale!When it comes to sex, I'm a total freak in the sheets. I love giving sloppy blowjobs, getting...
  • Looking for Love and Adventure!Looking for Love and Adventure! Hey there, lovely folks of Annapolis! I'm Trudey, a proud transgender woman who's ready to dive into the exciting world of dating. 💕 Living in this charming city by the Chesapeake Bay has been such a joy, but now I'm eager to share my adventures with someone special. As for me, well, I come in...
  • HMU for Sex in AnnapolisHMU for Sex in Annapolis Newly Single and Ready to Mingle in Annapolis 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 Annapolis, Maryland area then message me @BarbieSingle28.      ...
  • Hot Shemale in Annapolis Ready to Play and FuckHot Shemale in Annapolis Ready to Play and Fuck I'm a sexy shemale named Norry who's looking for a local man in Annapolis to have some wild and steamy fun with. I love getting down and dirty, so if you're into a good time, then I'm your girl... err, shemale! When it comes to sex, I'm not shy about what I like. I enjoy giving blowjobs and takin...
  • A Sensual Journey: Seeking Connection in AnnapolisA Sensual Journey: Seeking Connection in Annapolis Hey there! I'm Sascha, a transgender dating from Annapolis, Maryland. I may not fit society's norms, but that's what makes me unique and special. I love embracing my true self and being part of the LGBTQ community. I'm looking for someone who appreciates authenticity and is open-minded. Let's gra...
  • Raunchy Shemale Seeking Local Man for Hot Encounters in AnnapolisRaunchy Shemale Seeking Local Man for Hot Encounters in Annapolis Are you looking for a wild time with a sexy shemale in Annapolis, Maryland? Well, look no further because I'm Teena and I'm ready to fulfill all your dirty fantasies. I love getting down and dirty with a man who knows how to please me in all the right ways. From deepthroating your cock to riding y...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Are you looking for a hot shemale to fulfill all your wildest fantasies? Look no further, because I'm here to make all your dreams come true. My name is Susi and I'm a sexy shemale from Annapolis, Maryland who loves to play dirty. If you're into wild and kinky sex, then I'm the perfect match for y...
  • March 31st, 2025
  • Transgender Beauty Looking for Love in AnnapolisTransgender Beauty Looking for Love in Annapolis Hey there, I'm Mela, a proud transgender woman living in Annapolis, Maryland. I may not fit society's standards of beauty, but I rock my own unique body type and style. I love embracing my LGBTQ identity and all the strength and resilience that comes with it. I'm looking for someone who can appr...
  • New Body New MeNew Body New Me M2F post-op in Annapolis 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...
  • 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...
  • LetLet's Dance Under the Annapolis Stars Together Hey there! I'm Julianna, a confident and fun-loving transgender woman from Annapolis, Maryland. I love exploring the local art scene, trying out new restaurants, and taking long walks by the waterfront. Being part of the LGBTQ community has brought so much joy and acceptance into my life, and I wo...
  • TS M2F Top in AnnapolisTS M2F Top in Annapolis TS Top Seeking Man in Annapolis 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...
  • A Sensual Journey with LynnellA Sensual Journey with Lynnell Hey there! I'm Lynnell, a transgender woman from Annapolis, Maryland. I may not fit society's norms, but I embrace my uniqueness and love being part of the LGBTQ community. If you're looking for someone who is confident in their skin and loves to explore new adventures, then look no further! I en...
  • Sexy Shemale Darya Looking for Hot Fun in AnnapolisSexy Shemale Darya Looking for Hot Fun in Annapolis Are you ready to experience the ultimate pleasure with a naughty shemale like me? I'm Darya, a kinky tranny from Annapolis who loves to get down and dirty with a local man. If you're into wild and raunchy sex, then I'm the perfect match for you. I enjoy everything from deepthroating your cock to ...
  • A Night Under the Stars with AlizaA Night Under the Stars with Aliza Hey there! I'm Aliza, a fun-loving transgender gal from Annapolis, Maryland. I may not fit into society's traditional norms, but that's what makes me unique and special. I embrace my LGBTQ identity and love exploring new experiences.Whether it's grabbing a cup of coffee at City Dock Cafe, taking a s...
  • Wild Shemale Erika Ready to Play in Annapolis!Wild Shemale Erika Ready to Play in Annapolis! Looking for a hot man who can handle all my shemale desires. I'm Erika, a kinky tranny from Annapolis craving some wild fun. You can find me on FreeSexAds.com Shemale Profiles at erikaanna30617. I love getting down and dirty with a guy who knows how to please a shemale like me. I'm into everythin...