Annapolis, Maryland Shemale Sex Service Providers

Annapolis, Maryland shemale sex service providers. Find local crossdressers, transexuals and shemale sex providers including shemale escorts, body rubs, strippers, dom & fetish and more. Select your location below to find shemale sex providers near you. It's free to search or post your own ad!

Home / Shemale Sex Services /

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

  • December 16th, 2025
  • Annapolis Come See a Local Ebony Tranny Dance on The PholeAnnapolis Come See a Local Ebony Tranny Dance on The Phole  Ebony TS Goddess Seeks a VIP Date! 💵💰💎  Hey boys, I'm an Ebony Transsexual in Annapolis and I'm dancing tonight. Come hang out.. Let's have a few shows and maybe a dance. If you say you found me from this ad, I'll give you a SPECIAL DANCE!!! 👸💦 You like curves, confid...
  • TULA TGIRL - TS EscortsTULA TGIRL - TS Escorts Tula sexy top Ts ready for good time I love love sub bottoms and I love tops! kinky passionate discreet fun loving hot tranny wants to have some fun today so if you're looking for a hottie let this tranny have some fun with you and fulfill your fantasies I'm Ashley Merree call or text me.. Vie...
  • ❤️😍 TS Tease Ready to Please—Meet Me Tonight!😍❤️ ❤️😍 TS Tease Ready to Please—Meet Me Tonight!😍❤️  Sassy & Classy in AnnapolisCome Play with Me!  😍  Hey there sexy! 💋 I am your favorite trans bombshell dancing your fantasies of your  dreams. Get a private show for free at the club here in Annapolis, I’ll be there turning up the  heat. Of course, drinks a...
  • Looking for THE hottest drag queen in Annapolis?Looking for THE hottest drag queen in Annapolis? Drag Queen Escort Ready to go to the real drag races sexy? Of course you are! Why else would you be scopin' out my Annapolis trans escort listing? I'll take you to the races tonight and we'll run a few laps and get you to the finishing line for the BIG WIN BABY!!! The checkered flags are up an...
  • SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now!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 Black Sh...
  • Online Now 🟢 Ready to Play and Possibly Meet IRLOnline Now 🟢 Ready to Play and Possibly Meet IRL  A transsexual woman from Annapolis seeks someone to chat and flirt with potentially leading to  relationship formation. Your search for a passionate trans encounter ends here. I am currently transitioning and use  She/Her pronouns while enjoying hot moments especially when I am on ca...
  • SO PASSABLE YOU CAN TAKE ME HOME TO MOM AND DAD😇SO PASSABLE YOU CAN TAKE ME HOME TO MOM AND DAD😇 Shemale Escort in Annapolis Elegant and alluring I will bring your desires to life 💖🔥💫    Are you searching for an alluring Shemale Goddess to hookup with in Annapolis? That's right!! I'm a sexy escort and I'm here to please you DADDY.  You've come to the place as I'm ...
  • Hot Natural Tgirl in AnnapolisHot Natural Tgirl in Annapolis Hot Natural TGirl Companion I'm a 33 y.o shemale/trans girl looking to provide a great time for a fun, good man. I am versatile, very sensual and full of fun. I like to kiss as well...;) Feel free to inquire on further details. 420 friendly You will like what you see. Clean and safe play Visit me...
  • 24 y/o Crossdresser 🍭 seeks Man for Dates in Annapolis24 y/o Crossdresser 🍭 seeks Man for Dates in Annapolis Crossdresser Escort in Annapolis Girly crossdresser Ashley here for to service a men and I do know what you like! I'm always fun and flirty and clean and very feminine. No drama or rudeness ever. Incall/outcalls available. Contact me for same day appointment. I have a clean, safe place or you name ...
  • December 15th, 2025
  • Your Naughty Little Secret Awaits…AnnapolisYour Naughty Little Secret Awaits…Annapolis Want a dance with a shemale stripper??  Some secrets are too good to keep… I’m one of them baby, and I’m  trans. 😘 I’m the trans bombshell you’ve been dreaming about, they said, sexy,  confident, and always ready to play. Escape with me to a world of...
  • Annapolis TRANNY, needs❤️🍆Annapolis TRANNY, needs❤️🍆 HOT Transgender Lady WantingSex in Annapolis 💋 TONIGHT!!  Annapolis - Transgender Messanger  I'm a Transgender lady living in Annapolisor somewhere near by... I'm Born male,however I always known I am a pretty girl.I love meeting guys for sex and having fun. View My Tr...
  • Independent Shemale Escort Top or Bottom in AnnapolisIndependent Shemale Escort Top or Bottom in Annapolis Top or Bottom Shemale Escort in Annapolis Hey guys. I'm Maya Grace (@MayaGrace31). I am a sexy and sweet, but also naughty shemale in the Annapolis area. I'm friendly and outgoing, a total flirt and a tease. I will definitely make you feel proud to be with me. I will leave you happy & relaxed e...
  • Do you know the difference between a dick and a bucket of popcorn?Do you know the difference between a dick and a bucket of popcorn? Annapolis T-Girl Escort You don't know the difference? 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 Annapolis tranny escort tonight. Save your appetite boy! Me: trans, 30yr...
  • Trans Hookups in Annapolis, Maryland -- FREE PROFILE SEARCH -- Meet Local Trans Online!Trans Hookups in Annapolis, Maryland -- FREE PROFILE SEARCH -- Meet Local Trans Online! Trans Hookups in Annapolis, Maryland LocalTransHookups.com has teamed with TSDates to provide a free membership with instant access to all Maryland trans dating profiles. Meeting Annapolis transexuals isn’t quite as simple as meeting regular woman. Many transexuals feel uneasy about coming...
  • Trans Beauty Craving Connection – Let’s Get Intimate on Cam 🔥Trans Beauty Craving Connection – Let’s Get Intimate on Cam 🔥  Hey you 😘 I’m a transsexual woman who’s sweet, sexy, and ready to  build something exciting — whether it’s playful chatting, hot cam sessions, or something more meaningful. View My Profile and Message Me — I’m  waiting. I  identify as She/...
  • Come Play with BRITx – a TS Beauty in Annapolis 💃Come Play with BRITx – a TS Beauty in Annapolis 💃 BackRoom with BRITX – TS Beauty in Annapolis 💃 My Stripper Pix - Profile✅  Hello there! I'm Laryssa. I enjoy embracing fun and excitement in life while cherishing the moments of joy and fulfillment with others, around me too. Tonight you can find me at the club having a time dancin...
  • Your Trans Fantasy Starts Here – Let’s Cam First 💦Your Trans Fantasy Starts Here – Let’s Cam First 💦  Looking for a sexy, open-minded transgender woman in Annapolis? That’s me! I  love connecting on cam—it’s the perfect way to get to know each other before possibly meeting up.  She/Her, sensual, spontaneous, and ready to play. Click the link, view my  profile, ...
  • TS Temptress Online – Let’s Flirt, Cam & Maybe Fall in Lust 😈💋TS Temptress Online – Let’s Flirt, Cam & Maybe Fall in Lust 😈💋  As a sensual trans woman I seek someone to connect with through flirting to discover potential deep connections.  My pronouns are She/Her and I am currently in the process of transitioning while fully embracing all  the changes my body experiences  💋 Check out My Profile then...
  • Join Me on a Trans-Tastic Voyage Baby!Join Me on a Trans-Tastic Voyage Baby! Upscale Trans Escort in Annapolis Hey gents I'm Adriana a trans escort here in Annapolis to temp you into going on an adventure, a voyage into my sexual fantasy land. I'm upscale, professional, discreet, functional, fully passible, feminine, fabulous and will seduce you with my sexy flirtaciou...
  • EBONY🍆TS - incall and outcall💦EBONY🍆TS - incall and outcall💦 Ebony Shemale With BBC🍭do you like pretty black TS? My Personal Profile - View Here Name: PARIS EBONY TS 🍆 Ethnicity: Black - Ebony Age: 23 years old Height: 5'5"  Weight: 134lbs Location: Local, Willing to travel Op: Pre-Op 🐈 ( Still have my Cock) Services: B...
  • Cam-2-Cam Fun w/ a Trans Vixen in Annapolis 💕Cam-2-Cam Fun w/ a Trans Vixen in Annapolis 💕  I am online and ready to chat, flirt, and maybe even meet someone who knows how to  treat a trans goddess. 😇 I am She/Her, currently transitioning, and love naughty cam  sessions. Want to see where this could go? I’m good for a hookup if the vibe is  right. Come say hi ...
  • T-Girl with a big surprise - Your gonna fucking love every inch of it!T-Girl with a big surprise - Your gonna fucking love every inch of it! Annapolis's Fabulous Trans Escort Hi boys I'm Mona a trans escort here in the Annapolis area with a special treat. I'm fully functional, passible and extra large (10 thick inches uncut) Top or bottom and very kinky for all you sexy pervs out there who want to get the most out of Mona tonight. Tell ...
  • First timer, or simply curious, youFirst timer, or simply curious, you'll feel completely comfortable with me. I'm very discrete I am 25 year old fully-functional TS girl.  Let's get the physical stuff out the way first - I'm completely passable transexual (and then some). I have an amazingly sensuous model's body - toned and smooth, educated and classy. My measurements are 36D-29-34. I have a 9.5 inch thick, 100% fully...
  • Email Shemales💎AnnapolisEmail Shemales💎Annapolis Message Local Shemales and Transsexuals RADE PIX - MESSAGE - BROWSE PROFILES Meet Shemales, Transsexuals and TGirls for sex 😍 Hookups and fun tonight!! this app connects you locally with sexy SHEMALES who are online and party to play now ☑️ Check out what this site has to offe...
  • Seductive Roselia is excited to make your wildest dreams 💦 true AnnapolisSeductive Roselia is excited to make your wildest dreams 💦 true Annapolis SHEMALE BODY RUBS AND MASSAGE Located in Annapolis - Stop on in! 👄😻    Looking for a Sexy and Sensual Massage from a TS/Shemale, in Annapolis? Well search more! I'm Roselia ( SHE/HER ). I'm here to make sure you have a time with me ✨  As a transgender woman I love what ...
  • Vietnamese Trans Escort Serving the Annapolis Area...Vietnamese Trans Escort Serving the Annapolis Area... kawaiiTranX is back on demand in Annapolis for all loyal admirers. I a fully passible and functional trans female escort who can take care of you like no body else can. I make you wonder how you ever got along without kawaiiTranX before. Incall, outcall OK, no women, underage or police! Come se...
  • TATTOOED TRANSSEXUAL 🔥💥 HERE FOR SEX AND FUN!!TATTOOED TRANSSEXUAL 🔥💥 HERE FOR SEX AND FUN!! LOCAL SHEMALE ESCORT LISTINGI reside in {City} and I'm always ready! I have photos, with feedback from satisfied customers .. I will always satisfy and make you feel like the AMAZING MAN you are!! I also have been verified through P411 ✅💍 and you can also find me on OF, Want to see more pictur...
  • ❤️I❤️I'm Ts Love Bunny🐇Annapolis❤️ Your SHEMALE MASSAGE THERAPIST DO YOU WANT A LOCAL SHEMALEMASSAGE/ NURU THERAPIST? 💦💦   Hey babe, I'm here in Annapolis and I'm a college student. I'm really good with my hands and body so I'm doing this MASSAGE stuff as a way to make money on the side. Honestly I love it so much, I think I will always want to do thi...
  • Twisted Sister - Loves to Ride.... and be Ridden!Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Annapolis boos out there. I'm an independent trans escort serving the Annapolis area. 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 sexy, hung and fun. Y...
  • 🖤 Touch Me, Tease Me, Take Me Annapolis Shemale Rubs🖤 Touch Me, Tease Me, Take Me Annapolis Shemale Rubs  Are you aching for real connection? Come touch me. Our bodies will merge as I position  myself above you to share my fantasies while our skin dissolves into each other. View My Profile and Pictures - I’m a TS  goddess who loves kissing, sucking, licking, teasing, and intense ...
  • Horny Trans Cutie Online in Annapolis – Let’s Chat First 🟢Horny Trans Cutie Online in Annapolis – Let’s Chat First 🟢  Looking to meet someone real? I am a flirty, wild trans girl who is ready to  chat and see where things go. I get off on naughty cam convos and love to tease before  we take it further. Let’s heat things up and maybe plan a hot little meetup. Message  me, view my profile, ...
  • TS Girl Seeking Vibes, Cam Fun & Maybe Something Real 💖📲TS Girl Seeking Vibes, Cam Fun & Maybe Something Real 💖📲  Do you find attractive confident curvy trans girls who display a naughty smile and soft voice? You  already have my full attention 😘 The process of transitioning brings me great joy as I experience all  its wonderful aspects. She/Her stands as my preferred pronouns while I seek g...
  • PRE-OP HOTTIE READY TO PARTY AND PLAY!PRE-OP HOTTIE READY TO PARTY AND PLAY! Pre-Op Trans Hottie for Local Hookup Annapolis PreOp Hottie. My name is Angela but you can call me Angie. I am 5’8 tall 139 lbs, pre-op, versatile, AVAILABLE NOW MESSAGE ME WHEN YOU ARE READY TO MEET 420, PARTY FRIENDLY, GFE, NUDE SHOWER, KINKS!! xoxo Live Chat and Contact @AngieP...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Escort in Annapolis Hi I'm trans escort Trisha here to show you boys a different kind of kinky love in Annapolis. 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. This is for a kinky open minded man sort of man who appreciat...
  • S Beauty for Cam, Chemistry & Midnight Conversations 🌙📱S Beauty for Cam, Chemistry & Midnight Conversations 🌙📱  Hey handsome 😘 You will find me attractive because I am a trans woman who combines sweetness with  sensuality and playful nature. During my transition I use She/Her pronouns because I seek authentic  connections between two people. View My Profile and Message  Me – I&rs...
  • VIDEO✅VERIFY🍆Big Transgender Cock💦VIDEO✅VERIFY🍆Big Transgender Cock💦 PARTY TRANSSEXUAL GIRL 🎱☘️🎉💨IM VISITING & VERIFIED 💥 SEXY SHEMALE IN Annapolis lOOKING FOR SOMEACTION AND PLAY TONIGHT.. are you down? I have a sexy body and an amazing cock for you. 5 STAR⭐️ EXPERIENCE  * NDA’s ACCEPTED  / A+LIST  clients ...
  • SHEMALE INTO KINK 🔥 I WILL DOMINATE YOUSHEMALE INTO KINK 🔥 I WILL DOMINATE YOU Sexy Shemale DOMINATRIX Maryjo let's explore our kinks together!😈 My Name in Maryjo and I'm located in Annapolis.. I'm a very Kinky and horny shemale to play with your body and mind!💦  I want to own you and make you cry out in pleasure and pain. I will do unspeakable things to you a...
  • Welcome to the Land of Neons and Nylons Baby!Welcome to the Land of Neons and Nylons Baby! Big City Kitty here to share the glamour that is Annapolis with a sexy man tonight. You can take me anywhere, I'm a fully passable t-girl, functional and always in the mood for some hot sexy fun. Incall, outcall, travel, events, parties or anything you have in mind. I like it flashy and trashy! If y...
  • WhoWho's Your Tranny!!! Damn right I am! I know how to treat a man and please him, and I also know what I bring to the game. I give more than I recieve so don't be shy and message me if you live in the Annapolis area. I do incall, outcall, travel and all events. I'm passible, fully functional, and in the sheets I'm wild as...
  • AnnapolisAnnapolis's Own Trans Escort FABULOUS FRANCIS - I'm a Born Diva Honey!... T-Girl Escort in Annapolis I'm Fabulous Francis a trans escort here in Annapolis serving all you sexy guys with my sexy womanly wiles. I'm all the F-words baby! Fabulous, fun, fantastic, functional, friendly, flambouyant and very f#ckable! I do top or bottom and am extra large=well equipped. Let's ...
  • INTERACTIVE MAP: Transexual Tracker in the Annapolis Area!INTERACTIVE MAP: Transexual Tracker in the Annapolis Area! Local Trans Hookups Meet local transexuals in the Annapolis area for friendship or sex hookups. View our interactive map below to meet local trans members who want to meet local transexuals or admirers. Click a thumbnail to get started now! Interactive Annapolis Trans Hookups Map ...
  • Dr FreakinDr Freakin'Furter - Mine's Bigger Than Yours! White, 32 year old T-girl escort Freakin'Furter here in Annapolis, 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 meas...
  • ON STAGE TONIGHT!!  Shemale Laryssa 💋 Annapolis ON STAGE TONIGHT!! Shemale Laryssa 💋 Annapolis Sexy Shemale Laryssa Ready to Fulfill Your Wildest Fantasies 💋 Hey there, handsome! I'll be at the club tonight.. I will treat you extra special in the back room, if you know what I mean 💦👄 Are you looking for a sexy shemale in Annapolis  who knows how to have a good time? Look no fur...
  • OnebitchinOnebitchin' Babe in Annapolis Im a Funloving Person... You must live in the Annapolis area I am a Trans escort and will sex you up hard because I'm ALL the woman you need tonight baby! Tell me how you want it, you must be honest 100% No Bullsh#t. No games. No cops, no minors or lowballers PLEASE!! Sex isn't mandatory but, you must please be clean, respe...
  • Local Trans Dancers! 🥵🥰 Local Trans Dancers! 🥵🥰 TS Angel with a Devilish Side…😈Come see me at the club tonight!  By looks of things I am an innocent girl but oh baby don’t let that sweet face fool  you I know how to play dirty. I can never get enough of a man who knows how to  have fun and the only thing I enjoy mo...
  • Naughty boys check me out - Good thing I love naughty boys - Your wildest fantasies will come trueNaughty boys check me out - Good thing I love naughty boys - Your wildest fantasies will come true Tara here, I live to make your fantasies come true in Annapolis! I have a bubbly personality, enjoy intimate dinners, shopping, and I love as much as I receive. Fully passable, I dress to impress, STD free, classy, and ready to satisfy your needs and fetishes on short notice. I’m known for my ...
  • Annapolis Transsexual Body Rubs 💋 Kiss & Slide SessionAnnapolis Transsexual Body Rubs 💋 Kiss & Slide Session  Do you crave closeness? I’m the TS goddess who gives more than just a massage—I  give connection, fantasy, and deep release. I will touch you with warm oil and soft skin while  my body is pressed against yours from chest to chest with our mouths together and our hips and...
  • Trans Temptation Online – Let’s Cam, Laugh & Get Close 😘🎥Trans Temptation Online – Let’s Cam, Laugh & Get Close 😘🎥  Hey you 💋 As a TS beauty I have a flirty personality and playful thinking.  I’m transitioning, using She/Her pronouns, and I love making genuine connections that start with laughs  and lead to long, late-night cam sessions 😈View My Profile and Message Me – I’v...
  • TRANNY PORNSTAR, ELITE, Fun & Freaky down to earth transsexual. Im 100% Real (Guaranteed)TRANNY PORNSTAR, ELITE, Fun & Freaky down to earth transsexual. Im 100% Real (Guaranteed) Tranny Pornstar in Annapolis   A Very ELITE, Fun & Freaky down to earth transsexual. Im 100% Real (Guaranteed) & I've been seen all over the NET. Im completely versatile Top or Bottom, Aggressive or Submissive! I have beautiful natural 36D breasts.   I am a ts woman of many int...
  • Best big surprise you ever had baby!Best big surprise you ever had baby! Annapolis Ebony Tgirl Escort! I am a very sensual and sexual black transexual escort here in Annapolis. Love both bottom and top. Comment on and like my pics. I want you to share my pics and share me like you mean it with other men. Gay men, straight men, couples welcome, cis women welcome, curious...