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Catskills, New York Transgender Casual Encounters

Looking for trans hookups in Catskills, New York? Spunkpage features the latest transgender sex ads, from shemales and T-girls to crossdressers and trans babes. Post or browse adult classifieds to meet locals who are down to play.

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Latest Catskills, New York Transgender Ads

56 active listings • Page 1 of 2
September 16th, 2026
Unleash Your Inner Dom: Kinky Trans Woman Seeks Bondage Play

Unleash Your Inner Dom: Kinky Trans Woman Seeks Bondage Play

I'm a kinky trans woman with a craving for some bondage play. I want to be tied up, teased, and pleased by a dominant man who knows how to take control. Let's explore our deepest desires together and push each other to n...

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Sexy ShemaleπŸ’Ž Ready to Rock Your World!

Sexy ShemaleπŸ’Ž Ready to Rock Your World!

If you would like to have some fun in your local area with a very lovely Transgender girl, then I am your TGirl! I like to meet with men who know there own minds, and will know pretty much what they are looking for in an...

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Tina πŸ’‹πŸ’‹Trans Beauty Ready to Meet in Catskills

Tina πŸ’‹πŸ’‹Trans Beauty Ready to Meet in Catskills

Hey babe, it's Tina. I'm in Catskills and would love to meet up with a nice and funny person. Would love to see you sometime. I'm feeling really playful and would love to catch up with someone. Let me know if that sounds...

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Shy Crossdresser Seeks Friend for Discreet Dressing, Possible Dates | Catskills, New York Area

Shy Crossdresser Seeks Friend for Discreet Dressing, Possible Dates | Catskills, New York Area

Hello. I'm a married crossdresser in the Catskills area. My fem name is Gloria. I'm 28 years old, clean and disease free. I am passable in appearance and voice but the problem is that my wife doesn't approve. She knows b...

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Mind-blowing Trans Woman Ready To Give You Pleasure Like Never Before

Mind-blowing Trans Woman Ready To Give You Pleasure Like Never Before

Hey everyone, I'm a trans woman looking to give some mind-blowing blowjobs. I may have a little extra something down below, but trust me, I know how to use it ?. If you're in the mood for a good time and want to experien...

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Trans Woman Seeks PNP Fun With Adventurous Guys For Wild Exploration.

Trans Woman Seeks PNP Fun With Adventurous Guys For Wild Exploration.

I'm a trans woman with a craving to PNP and looking for guys who are down to get wild. I want to feel your hands all over me as we explore each other's bodies. Let's forget about the world outside and just focus on havin...

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Unleash Your Desires: Discreet Head For Ultimate Satisfaction Guaranteed ?

Unleash Your Desires: Discreet Head For Ultimate Satisfaction Guaranteed ?

Looking to give anonymous head to guys who need some discreet release. I'll make sure you leave satisfied and wanting more. No strings attached, just pure pleasure for both of us. Let's meet up, have some fun, and go our...

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Powerful African-Queen Dominatrix in Catskills, New York

Powerful African-Queen Dominatrix in Catskills, New York

Professional Domme Desiree is interviewing subs. My Catskills dungeon is well equipped, as this is My life, not a hobby. I am a strong, powerful shemale who will take charge and maintain total control. Your obedience wil...

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Let's Get Kinky: Trans Woman Wants Dick Sucked By You

Let's Get Kinky: Trans Woman Wants Dick Sucked By You

I'm a trans woman looking to get my dick sucked by a willing guy. I'm clean, chill, and down for some fun ? Let's make each other feel good and enjoy ourselves. No strings attached, just a good time between two consentin...

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Throbbing Surprise: Trans Woman Seeks Horny Men For Wild, Anonymous Fun.

Throbbing Surprise: Trans Woman Seeks Horny Men For Wild, Anonymous Fun.

I'm a sexy transgender woman with a throbbing surprise down below, looking to anonymously fuck with some horny men. I'm not interested in small talk, just want to get straight to the point and have a wild time together. ...

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TS Sugar BabyπŸ’Ž Your Perfect Trans Fantasy

TS Sugar BabyπŸ’Ž Your Perfect Trans Fantasy

Trans girls in Catskills Want to meet sexy TGirls, transgender women or trans woman? Transdate is a great site to meet and connect with TGirls, as well as with sexy and open-minded men looking to date and flirt with them...

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September 15th, 2026
πŸ’Ž Playful Trans Beauty Seeking a Generous Gentleman

πŸ’Ž Playful Trans Beauty Seeking a Generous Gentleman

A little about me: Hi there! I’m a sweet, playful trans woman in my early 20s who loves good energy, great chemistry, and nights that turn into unforgettable memories. I’m a bit of a baby at heart 🍭 and I enj...

πŸ”’ Contact info available to members only. Membership is free!
TS Sugar Baby πŸ’Ž Femme

TS Sugar Baby πŸ’Ž Femme

A little bit about me. I’m a trans sugar baby and have a huge love for anything feminine. I love to be told how beautiful I look and how much you appreciate me. So, I’m looking for a confident man who knows w...

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Sexy hung and big busted Catskills shemale πŸ†πŸ’¦

Sexy hung and big busted Catskills shemale πŸ†πŸ’¦

Hung and Busty Shemale in Catskills Hey, I'm Tammy, age 33, 38DD, well endowed lady stick, and so cute!! What more could you want in a gurl?πŸ†πŸ’¦Send your pics for mine and check my profile @Tammy38DD so we can talk and mee...

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Hung Guys Wanted To Plow This Trans Woman - Satisfaction Guaranteed!

Hung Guys Wanted To Plow This Trans Woman - Satisfaction Guaranteed!

Looking to get plowed by some hung guys who know how to handle a trans woman like me. I'm craving some rough and intense pounding that will leave me begging for more. Let's make each other moan and sweat as we explore ou...

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SHEMALE BEAUTY Ready to Eat Your Manhood Now! πŸ†πŸ’¦

SHEMALE BEAUTY Ready to Eat Your Manhood Now! πŸ†πŸ’¦

Hey there! I am Blanca, a shemale beauty queen who can take top or bottom. I am ready to eat your manhood now.  πŸ†πŸ’¦ We can do bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my...

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Let's Get Naughty: Anonymous Head For Your Pleasure Only!

Let's Get Naughty: Anonymous Head For Your Pleasure Only!

I need to give some anonymous head to guys who need it. I'm all about keeping things discreet and drama-free, just looking to have a good time and satisfy your needs. ?? Whether you're curious, straight, or bi, I'm here ...

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Gloryhole Fun: Let Me Worship Your Cock With No Strings Attached ?

Gloryhole Fun: Let Me Worship Your Cock With No Strings Attached ?

I'm looking to give head in my private gloryhole. Come over and let me take care of you ? I'll make sure you leave satisfied and drained. No strings attached, just pure pleasure for both of us. Slide your cock through th...

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Shemale Fantasy? Let Me Take Care of That.

Shemale Fantasy? Let Me Take Care of That.

"Experience your shemale fantasy in real life!"  Hi, I'm Gia, a shemale who loves introducing male trans admirers to the sexy world of shemale sex. I'm available to hook up with you in Catskills! No strings and no d...

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⚠️ Warning: This Ebony TS Beauty Is Hard to Forget

⚠️ Warning: This Ebony TS Beauty Is Hard to Forget

A little warning… I tend to leave a lasting impression. πŸ˜‰View My Ebony TS Profile Here I’m more than just a pretty face. I’m a confident Ebony TS woman who enjoys playful teasing, captivating attention...

πŸ”’ Contact info available to members only. Membership is free!
Ravage My Ass And Make Me Scream With Pleasure Now

Ravage My Ass And Make Me Scream With Pleasure Now

I'm a trans woman with a hunger for getting my ass destroyed by men who know how to handle themselves in the bedroom. I want you to pound me hard and make me scream with pleasure. I'm not looking for anything serious, ju...

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Seeking Men For Anonymous Head - Pure Pleasure, No Strings Attached.

Seeking Men For Anonymous Head - Pure Pleasure, No Strings Attached.

I need to give some anonymous head to men who need it. ? No strings attached, just pure pleasure for both of us. I'll make sure you leave satisfied and wanting more. Let's meet up in a discreet spot and get down to busin...

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Trans Woman Seeks Hung Men To Destroy Her Ass, No Small Talk.

Trans Woman Seeks Hung Men To Destroy Her Ass, No Small Talk.

I'm a transgender woman with a craving to get my ass destroyed by some well-hung men. I want you to pound me hard and make me scream with pleasure. I'm looking for guys who know how to handle a girl like me and can give ...

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Throbbing Trans Woman Seeks Man For Deep Anal Exploration ?

Throbbing Trans Woman Seeks Man For Deep Anal Exploration ?

I'm a transgender woman with a throbbing desire to fuck a man's ass. I'm looking for someone who craves the feeling of being drilled deep and hard. Let's explore our wildest fantasies together and make each other moan in...

πŸ”’ Contact info available to members only. Membership is free!
πŸ’‹ Sweet Looks, Wild Energy – TS Beauty Waiting

πŸ’‹ Sweet Looks, Wild Energy – TS Beauty Waiting

Sweet on the surface… a little wicked underneath. πŸ˜‰View My Trans Dating Profile Here  TS Beauty seeking fun beauty for times when beauty is needed. Imagine a pair of stockings, a pair of high heels, a body hu...

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Hung and Big Busted Tranny Babe with Added Surprise! πŸ‘πŸ‘πŸ†

Hung and Big Busted Tranny Babe with Added Surprise! πŸ‘πŸ‘πŸ†

Tammy non-op tranny, age 39, big yummy tits!! πŸ‘πŸ‘ Well hung πŸ† just waiting to be discovered in my panties (also yum!). Everything works, clean and so cute!! What more could you want in a gurl?!! Let's swap pics and number...

πŸ”’ Contact info available to members only. Membership is free!
Ass-destroying Man Wanted To Pound Me Hard And Deep Tonight ?

Ass-destroying Man Wanted To Pound Me Hard And Deep Tonight ?

I'm looking to get my ass destroyed. I want a man who can pound me like there's no tomorrow. I'm a transgender woman with a hunger for some rough action. Let's make this an unforgettable experience ?. I'm ready to be dri...

πŸ”’ Contact info available to members only. Membership is free!
Hard Cocked Trans Woman Seeks Tight Asses For Pounding Pleasure.

Hard Cocked Trans Woman Seeks Tight Asses For Pounding Pleasure.

I'm a trans woman with a hard cock, and I need to plow some tight asses. ? If you're a guy who's craving a good pounding, then look no further! I'm all about giving and receiving pleasure, so let's make each other moan w...

πŸ”’ Contact info available to members only. Membership is free!
CatskillsπŸ’‹Your Playful TS Dream Girl

CatskillsπŸ’‹Your Playful TS Dream Girl

Hey sexy… it’s Tina, your sweet and seductive TS dream girl ready to connect and share some exciting energy. 😘πŸ”₯ Let's Get to Know Eachother!! I’m playful, confident, and love meeting men who know how t...

πŸ”’ Contact info available to members only. Membership is free!
Let's Push Boundaries And Explore BDSM Together, Dominate Me Tonight

Let's Push Boundaries And Explore BDSM Together, Dominate Me Tonight

I'm looking to BDSM play with men who are into exploring their dominant side. I love being tied up, spanked, and teased until I beg for more. I want someone who can take control and show me who's boss in the bedroom. Let...

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Penny Non-Op TS Bottom or Top | Catskills, New York

Penny Non-Op TS Bottom or Top | Catskills, New York

Hey, I am Penny, a non-op TS who can switch top or bottom for your pleasure, and I aim to please! I am recently new here and I am pretty nicely endowed! Send me a message online @PennyTSswitch!! I'm a mixed race trans sw...

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September 14th, 2026
Gorgeous Preop Shemale Krystale Visiting Catskills

Gorgeous Preop Shemale Krystale Visiting Catskills

I am Krystale, a preop shemale, not really planning on going any further with transition because I love being a functional shemale. It is truly the best of both worlds! I am visiting and lonely here in this new place. Wo...

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Destroy My Ass And Dominate Me - Trans Woman Seeks Hung Studs.

Destroy My Ass And Dominate Me - Trans Woman Seeks Hung Studs.

I'm looking to get my ass destroyed by some hung guys who know how to handle a trans woman like me. I want you to pound me hard and make me scream with pleasure. I'm craving that feeling of being completely filled up and...

πŸ”’ Contact info available to members only. Membership is free!
Mind-blowing Blowjobs For Guys Who Can Handle It, Satisfaction Guaranteed!

Mind-blowing Blowjobs For Guys Who Can Handle It, Satisfaction Guaranteed!

I need to give some mind-blowing blowjobs to guys who can handle it. My lips are ready to work their magic and make you feel like you're in heaven. I'll take my time, savor every moment, and leave you begging for more. ?...

πŸ”’ Contact info available to members only. Membership is free!
Exotic Asian Queen in Catskills Now

Exotic Asian Queen in Catskills Now

Asian Transexual visiting Catskills  Stunning Asian TS Queen - Talia, age 25. Non op, functional, loves sex and is an unselfish satisfier. Nice build with long slender legs to wrap around you. Message me @Talia...

πŸ”’ Contact info available to members only. Membership is free!
Heyyy! 😍 It's Crystal 27 y/o Hot Trans Fem | Catskills, New York

Heyyy! 😍 It's Crystal 27 y/o Hot Trans Fem | Catskills, New York

Heyyy there! Thanks for checking my ad. I'm Crystal and I am 27. I'm fairly new to the Catskills area and want to get to out explore the area. I'd love make some new friends and maybe find romance! I am a masseuse with g...

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Kinky Trans Woman Seeking Mind-Blowing Blowjob - Let's Explore Together!

Kinky Trans Woman Seeking Mind-Blowing Blowjob - Let's Explore Together!

I'm a transgender woman with a throbbing desire for a mind-blowing blowjob.?? I'm looking for a guy who knows how to handle my package with care and enthusiasm. Let's make each other feel amazing as we explore our deepes...

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Let's Make Magic Happen Behind Closed Doors - Satisfaction Guaranteed!

Let's Make Magic Happen Behind Closed Doors - Satisfaction Guaranteed!

I need a man who's craving a good pounding. I've got the equipment to make your wildest fantasies come true. Let's explore each other's bodies and experience pure ecstasy together. ?? Don't be shy, I know exactly what I ...

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Trans Woman Seeking Hot, Horny Men To Pound Me Hard.

Trans Woman Seeking Hot, Horny Men To Pound Me Hard.

I'm a transgender woman with a craving to get plowed by some hot, horny men. I want you to pound me like there's no tomorrow and make me scream with pleasure. Let's have a wild time together and explore our deepest desir...

πŸ”’ Contact info available to members only. Membership is free!
Anonymous Head For Guys Who Need It. No Strings Attached Pleasure.

Anonymous Head For Guys Who Need It. No Strings Attached Pleasure.

I'm looking to give anonymous head to guys who need it. No strings attached, just a good time for both of us. I love the thrill of not knowing who you are, just feeling you in my mouth. Let's meet up, get off, and go our...

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πŸ’‹ Late Night TGirl Fantasy Awaits

πŸ’‹ Late Night TGirl Fantasy Awaits

It’s late. You’re still awake. Something about the night has you craving a little excitement… something different. 😏- View My TGIRL Dating Profile -  I’m the kind of TS fantasy girl who brin...

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September 13th, 2026
Seeking Anonymous Head? Let's Fulfill Your Wildest Fantasies Tonight ?

Seeking Anonymous Head? Let's Fulfill Your Wildest Fantasies Tonight ?

I need for some fun, looking to give anonymous head to guys who need a good time. No strings attached, just pure pleasure. I'm discreet and down to get you off in any way you desire. Let's make this a night to remember ?...

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Sexy Trans Woman With Throbbing Surprise Seeks NSA Fun With Men.

Sexy Trans Woman With Throbbing Surprise Seeks NSA Fun With Men.

I'm a sexy trans woman with a throbbing surprise between my legs, looking to NSA fuck with horny guys who can handle it all. I'm not here for games or drama, just pure adult fun. ?? If you're into exploring new things an...

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Trans Woman Seeking Men To Fulfill Ass Destruction Fantasies Together.

Trans Woman Seeking Men To Fulfill Ass Destruction Fantasies Together.

I'm a transgender woman with a craving to destroy ass. I'm looking for men who can handle my throbbing desire to pound them into oblivion. I want to feel your body quiver as I take you to new heights of ecstasy. Let's ex...

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Seductive Trans Woman Ready To Plow - Let's Get Wild!

Seductive Trans Woman Ready To Plow - Let's Get Wild!

I'm a transgender woman with a craving to plow some ass. I'm looking for men who are down for a good time and ready to get pounded. I want to feel you squirm beneath me as I take control and give you the ride of your lif...

πŸ”’ Contact info available to members only. Membership is free!
Horny Trans Woman Ready To Fulfill Your Wildest Desires ??

Horny Trans Woman Ready To Fulfill Your Wildest Desires ??

I'm a horny trans woman with a hard cock looking to NSA fuck. I want to feel your hands all over me, exploring every inch of my body. Let's get lost in the moment and fulfill each other's desires. I'm open-minded and rea...

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Destroy My Trans Ass And Make Me Scream With Pleasure!

Destroy My Trans Ass And Make Me Scream With Pleasure!

I'm a trans woman with a craving to get my ass destroyed by some horny guys. I want you to pound me hard and make me scream with pleasure. Let's have a wild time together and fulfill all our dirty fantasies. I'm open to ...

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πŸ’Ž Confident Ebony TS Beauty Seeking a Bold Man

πŸ’Ž Confident Ebony TS Beauty Seeking a Bold Man

If you’re someone who prefers real connection over endless small talk, then we’re already on the right track. πŸ˜‰I’m a curvy Ebony TS woman who loves attention, enjoys playful chemistry, and knows how to ...

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Sexy Trans Woman Offering Private Gloryhole Fun For Discreet Men

Sexy Trans Woman Offering Private Gloryhole Fun For Discreet Men

Hey, I'm a sexy transgender woman with a craving to give head in my private gloryhole. ?? If you're a man who needs some discreet and no-strings-attached fun, then I'm your girl! Come over and let me take care of you lik...

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Trans Woman Seeking Skilled Guy For Blowjob Fun, No Small Talk.

Trans Woman Seeking Skilled Guy For Blowjob Fun, No Small Talk.

Looking to get a blowjob from a guy who knows how to handle what I'm packing. I'm a transgender woman with a little something extra down below, ready to be pleased. Let's have some fun together and make each other feel g...

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