New Haven, Connecticut Shemale Dating Classifieds

New Haven, Connecticut shemale dating classifieds. Meet local crossdressers, transexuals and shemales for romance, sex or just make new transgender friends. escorts, body rubs & sex service listings. Select your location below to find shemales near you. It's free to search or post your own ad!

Home / Shemale Dating /

Show Ads In: Eastern CT | Hartford | Northwest CT | New Haven

June 22nd, 2026

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

Flawlessly gorgeous trans bombshell in New Haven Trans MtF for Man in New Haven 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 New Haven. New Haven T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the New Haven 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...

Tiffany Shelle - Your New Haven Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in New Haven 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% function...

Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in New Haven 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 nau...

New Haven Addicted to shemales... Male Seeking TS  A handsome, fit and confident man, seeking a stunning TS girl to spend exciting nights and incredible  moments with. I have a thing for flirty conversations, passionate chemistry and playful antics- if you  are looking for a casual meet or if we can make this a more regular thing, I ...

TS Beauties—Let’s Have Some REAL Fun! 😏🔥  I am a tall, fit, and successful man and I have a taste for gorgeous TS women  who love to be adored, desired and pleasured. Whether you are looking for a wild  night, a passionate escape or something ongoing, I know how to treat a woman right. 💋 Must  have confidence, charm...

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

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

THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! 😉 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...

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

Superior Massage by gorgeous T-Girl T-Girl for Dating in New Haven 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...

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

Erotic exotic Asian queen in New Haven now (25) Asian Transexual in New Haven 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 New Haven 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 New Haven 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...

TS Latina Dream Girl – Ride Me Like a Telenovela 😈📺  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...

👠 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 New Haven 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 New Haven 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...

SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in New Haven Secret Crossdressing Hookups in New Haven 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 g...

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE New Haven 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...

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

Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in New Haven 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.. ...

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 New Haven Hi I'm tgirl Trisha to show you boys a different kind of kinky love in New Haven. 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 w...

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

👑 Chocolate Queen with Soft Curves & Naughty Desires 🔥  🔥| 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 ...

👄 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...

TS Bombshell Looking for a Man Who Can Keep Up! 💋 New Haven  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...

Let’s Get a Drink… and See Where It Leads 😘  One Night, No Limits...  New HavenShemale 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 s...

FtM seeking Princess Bride in New Haven FtM seeking Woman in New Haven Hi, I'm Andy, age 33, FtM transgender man living in New Haven. 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...

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,...

Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in New Haven Area Hi, my fem name is Gloria. I'm a married crossdresser in the New Haven 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...

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...

Penny for your thoughts? Penny TS in New Haven 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 hi...

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...

I'm a Horny Shemale 😈💋 Looking For Sex Tonight!! Sexy Shemale💎 Ready to Rock Your World! Local Transsexual - TGIRL Sext App 📲 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...

Flirty & Feminine CD Ready for Some Fun 💕😈  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.  💋 💎 Bath g...

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

June 21st, 2026

Looking for My TS Queen 👑💋 I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. 💕 I appreciate a woman who knows her worth and loves to be treated right. Whether it’s a romantic dinner, steamy nights, or spontaneous adventures,...

HOT SHEMALE GIA will Satisfy Your Tranny Fantasy New Haven! 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 New Haven!  No strings - just great times, so join my page free for instant access! Shemale Gia's New Haven Sexbook @ShemaleGia27 Photos: 4...

Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in New Haven 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!&...

Seeking All TS Beauties in New Haven  I am a masculine, dominant, and very passionate man, and I am looking for a sensual  and seductive TS woman to explore our deepest desires together. No matter whether you like to be the  boss or to be taken care of, I am all about creating electric chemistry and unforgettable moments...

🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘 💖 Hey, Handsome! I’m a sultry, curvy ebony TS  here in New Haven... 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...

Free Connecticut Transexuals Guide Connecticut Transexuals Guide The Connecticut 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 Connecticut Transexuals Guide online.  Where to Meet Transexual...

Spicy and Hot T-Girl from Colombia Latina T-Girl in New Haven Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...

Your Shemale Addiction 😈🥵 Starts Now Shemale Seeking Male.. Your Fantasy Starts Here 24yr old Transsexual/Shemale in New Haven seeking some fun and campanionship. I would like hookups and I'm also wanting love. I think we should play some plans and see what we can come up with.. I'm open minded and ready!! Take a min to View my P...