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TS Escorts & Shemale Escorts in Chicago, IL

Chicago, IL Activities
Nearby locations:
Rosemont, IL (4) | Elmhurst, IL (2) | Oak Brook, IL (5) | Mt Prospect, IL (1) | Schaumburg, IL (1)

TS Escort Of The Day

AnnaTranny
Portland, OR
Hello, I’m Top Anna — 🌟100% me on Pictures🌟, FaceTime is an option to verify, an elegant, captivating trans companion offering sophisticated and unforgettable experiences. Whether you’re seeking a charming dinner date, engaging conversation, or simply a moment to unwind, I pride myself on creating a connection that’s uniquely tailored to your desires. I am: 🌟 5’8”, with a slender and skinny build 🌟 Confident, intelligent, and compassionate 🌟 Always impeccably dressed to suit any occasion Discretion and respect are my top priorities, and I value meaningful, mutually fulfilling encounters. My HOT 🥵 OnlyFans ➡️ https://onlyfans.com/selena_tranny ⬅️
View profile
AnnaTranny
Portland, OR
23 Jul, 22:56
Age
23 Y/O
I Am
Trans woman
Ethnicity
Caucasian
Reviews
1 Review
Videos
1 Video
Dallas
04 Aug - 11 Aug
Phoenix
11 Aug - 16 Aug

ts4rent exclusive

Karinasecret Tysons, VA
Available Now
laralovexxx Brooklyn, NY
23 Jul, 14:17
Rominna Tampa, FL
24 Jul, 20:43
ALEXIABLONDEXXL Baltimore, MD
24 Jul, 16:45
Marykate Naples, FL
Available Now
MARBELLA_SECRET Tysons, VA
9 hours ago

Chicago, IL TS Escorts, Shemale & Trans escorts

  • Platinum Boost
    Sabrina_Xoxo
    Chicago, IL
    Available Now
    Sabrina_Xoxo
    Sabrina❤ Beautiful 🌹brown eyes, nice pretty face with long hair that Hangs down to the middle of my back Gorgeous 😘girl here soft skin😊& right now I love to have a great time with you Anything is possible💋. 8’ff 🍭 VERS ✨
  • Platinum Boost
    bellaxxlove
    Chicago, IL
    8 hours ago
    bellaxxlove
    Hi Cutie! I’m , a sexy trans girl searching for a daddy who’s ready to make me their personal little slut 💦💦🙈. I’m playful, young, and always eager to explore. I’ve got a talent for fulfilling fantasies and bringing kinks to life, and I’m always down to try something at least once.😜 I’m in town and
  • Platinum Boost
    LillyOfTheValley
    Chicago, IL
    9 hours ago
    LillyOfTheValley
    Providing discretion, safety, professionalism, and an experience you have never gotten from anyone before. I'm an incredibly sensitive, sensual, and caring person in all areas of life. I appreciate men who know what they like and can express those desires to me clearly. I’m a woman who genuinely
  • Platinum Boost
    TsArianaangel
    Chicago, IL
    Today, 00:09
    TsArianaangel
    Hii I’m Ariana welcome to my page 🥰 23 year old, big booty trans girl . I look exactly the same in person or better some would argue 🥰 Let me fulfill your fantasies and take away from your worries. I would love to captivate your mind and tingle your senses, I will make you feel in your body and s
  • Platinum Boost
    TsOliviaSkye
    Chicago, IL
    Today, 00:07
    TsOliviaSkye
    hii i’m olivia skye 🥰 welcome to my page! https://onlyfans.com/tsoliviaskye/c20 21 y/o petite brunette trans girl with a naughty side i’m dying to show you 😘 i’m sweet, shy at first… but once you get to know me, i get real bad real fast 😈💋 whether you wanna be teased, spoiled, or completely wrecke
  • Platinum Boost
    GingerAnastasia
    Chicago, IL
    24 Jul, 22:45
    GingerAnastasia
    Tall Slavic redhead with a fully functional💦 model body ready to make your fantasies come true 😉 While discretion is always a top priority it is appreciated if you can send a picture of yourself. I am nda experienced and open to signing. I look exactly like my pictures and am available for FaceTi
  • Platinum Boost
    princesskit
    Chicago, IL
    5 hours ago
    princesskit
    Kit’s something fun and different: she’s a pretty girl tomboy with a naturally feminine and addicting physique that is 100% all real. I’m a sweetheart with a nasty mind. Take me out and savor me. Nothing I like more than a guy who knows what he’s got and how to enjoy it. I’m a playful princess, an
  • Platinum Boost
    Vvictoria
    Chicago, IL
    9 hours ago
    Vvictoria
    Hey there, Treat yourself to the most pleasurable fantasy that your body and mind could ever imagine. Our time together is never rushed. It will always be comfortable and discreet. I certainly look forward to meeting you,...
  • GoddesBunny
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  • Dark_Lovely
    Chicago, IL
    Available Now
    I am a beautiful 27-year-old international model based in Los Angeles, New York. I'm your typical girl next-door with a great sense of style, beautiful chocolate skin, and impeccable hygiene. I smell absolutely amazing and prioritize cleanliness. I enjoy serving men who appreciate the finer things i...
  • jaydeswrld
    Chicago, IL
    Available Now
    All-American White TS Dream 🇺🇸 | Curvy, Sultry & Fully Functional 💋 Contact me on OnlyFans for advance/priority bookings: https://onlyfans.com/jaydeswrld/c28 Looking for a truly unforgettable experience? I’m a gorgeous, curvy TS companion with that irresistible porn star body and a passion for ple
  • Krysten
    Chicago, IL
    Available Now
    Beautiful Latin TS Kristen ✨ HELLO GENTLEMEN ! 🌹 My Name is Kristen I'm a Very Passable Latin Gurl 30 y.o. 5'8” tall, 158 lbs, 7”FF tool hard as rock! I’m not on hormones. "I CAN GIVE YOU THE BEST NICE & RELAXING BODY RUB" First Timers, Straight, Bi, Curious and Mature Gentlemen are Welcome! Cal
  • CaliforniaCutey
    Chicago, IL
    Available Now
    📱Available Now (818)-491-6111 📱 Hello, my name is Cali. I'm the Tall, Blonde, White and Curvy TS goddess you've been dreaming about! I'm fun, frisky and know how to please;) I have naturally smooth skin, long gorgeous legs, large breast implants and a perfect bubble butt. Nails are always manicure
  • solLove
    Chicago, IL
    Available Now
    Available now Novi MI🌹 💋♥️🌹💋♥️ don't miss out guy's kisses XOXO LIMITED TIME HI GUYS SolLove 2025 from Chicago ❌❌ ❌IF YOU ARE MEMBER YOU CAN SEE MY NEW resend PIC AND VIDEOS I AM BACK BY POPULAR DEMAND I am a start traveling again , ATHLETIC, HOT, SEXY,JUST FABULOUS SolLove 2024 ❌❌❌❌✈️✈️✈️
  • CocoHung
    Chicago, IL
    Private
    See my porn videos below; www.onlyfans.com/cocoyummyy www.twitter.com/cocoyummyy ** highly selective & real. Trusted by many from businessmen to professional athletes and everyone in between as a seductive TS playmate & fun friend. Discretion Assured
  • LunaaTS
    Chicago, IL
    Available Now
    hii, I’m Lunnaaa 💖 The softest 18yo t-girl you'll ever meet, i’m still discovering everything i can do with my body… and maybe with you? 🫣 I study full-time so I’m not always available I only see respectful clients who vibe well with me message me on OF to book (it’s totally free) : onlyfans.com/
  • AlejandraFoxTS
    Chicago, IL
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    𝐇𝐞𝐲 𝐛𝐚𝐛𝐞, 𝐈'𝐦 Alejandra 💋, 𝐲𝐨𝐮𝐫 𝐬𝐞𝐜𝐫𝐞𝐭 𝐠𝐢𝐫𝐥 𝐟𝐨𝐫 𝐭𝐨𝐧𝐢𝐠𝐡𝐭 🔥 𝗦𝗹𝗶𝗺 𝘄𝗮𝗶𝘀𝘁, 𝗷𝘂𝗶𝗰𝘆 𝗯𝘂𝗯𝗯𝗹𝗲 𝗯𝘂𝘁𝘁 🍑 & 𝟳.𝟱" 🍆 𝗖𝗮𝘁𝗰𝗵 𝗺𝗲 𝗼𝗻 𝗧𝗢𝗨𝗥 𝗶𝗻 𝘁𝗵𝗲 𝗨𝗦𝗔 🇺🇸 — 𝗼𝗻𝗹𝘆 𝗳𝗼𝗿 𝗮 𝗹𝗶𝗺𝗶𝘁𝗲𝗱 𝘁𝗶𝗺𝗲... 𝗖𝗼𝗺𝗲 𝗹𝗶𝘃𝗲 𝗼𝘂𝘁 𝘆𝗼𝘂𝗿 𝗻𝗮𝘂𝗴𝗵𝘁𝗶𝗲𝘀𝘁 𝗱𝗿𝗲𝗮𝗺𝘀 𝘄𝗶𝘁𝗵 𝗺𝗲 💦 ▶ 𝗘𝘅𝗰𝗹𝘂𝘀𝗶𝘃𝗲 𝗵𝗼𝘁 𝗰𝗹𝗶𝗽𝘀 𝘄𝗶𝘁𝗵 𝗿𝗲𝗮𝗹 𝗰𝗹𝗶𝗲𝗻𝘁𝘀 𝗼𝗻 𝗢𝗡𝗟𝗬𝗙𝗔𝗡𝗦 (𝐅𝐑𝐄𝐄): ▶ onlyfans.com/waifuealejandra/
  • BlondieTS
    Chicago, IL
    Available Now
    𝐇𝐞𝐲 𝐛𝐚𝐛𝐞, 𝐈'𝐦 𝐀𝐥𝐞𝐣𝐚𝐧𝐝𝐫𝐚 💋 𝐲𝐨𝐮𝐫 𝐛𝐥𝐨𝐧𝐝𝐞 𝐝𝐨𝐥𝐥 𝐟𝐨𝐫 𝐭𝐡𝐞 𝐧𝐢𝐠𝐡𝐭 💛 𝐓𝐢𝐠𝐡𝐭 𝐰𝐚𝐢𝐬𝐭, 𝐣𝐮𝐢𝐜𝐲 🍑, 𝐛𝐢𝐠 𝐫𝐨𝐮𝐧𝐝 🍒 𝐚𝐧𝐝... 𝟕.𝟓" 🍆 𝐎𝐍 𝐓𝐎𝐔𝐑 𝐍𝐎𝐖 𝐢𝐧 🇺🇸 𝐟𝐨𝐫 𝐚 𝐥𝐢𝐦𝐢𝐭𝐞𝐝 𝐭𝐢𝐦𝐞 🚨 📹 𝐇𝐨𝐭 𝐜𝐥𝐢𝐩𝐬 𝐰𝐢𝐭𝐡 𝐫𝐞𝐚𝐥 𝐜𝐥𝐢𝐞𝐧𝐭𝐬 𝐨𝐧 𝐎𝐍𝐋𝐘𝐅𝐀𝐍𝐒 (𝐅𝐑𝐄𝐄): https://onlyfans.com/alejfox.ts/c81 💋 𝐇𝐢𝐠𝐡 𝐜𝐥𝐚𝐬𝐬, 𝐚𝐥𝐰𝐚𝐲𝐬 𝐜𝐥𝐞𝐚𝐧, 𝐚𝐧𝐝 𝐝𝐫𝐞𝐬𝐬𝐞𝐝 𝐭𝐨 𝐢𝐦𝐩𝐫𝐞𝐬𝐬 👑 𝐎𝐩𝐞𝐧-𝐦𝐢𝐧𝐝𝐞𝐝
  • Jasmine_li
    Chicago, IL
    3 hours ago
    Confident Young Lady who is sweet , and Fun to be around. * Only available for gentlemen who know's how to respect , has good hygiene and knows how to treat a girl like me. *Upon contacting me , give a little introduction of yourself and a photo attached to it I screen all of my future dates no...
  • Alexalatina
    Chicago, IL
    Available Now
    JUST VISITING ✈️ Hello, My name is Alexa . I’m a sexy Hispanic ready to please your great desires. I would love to accompany you for long or short term engagements, dinner dates, drinks, shows, overnights, travels or in simplicity and it be in private evenings of relaxation My ultimate goal as a T
  • Angelina_XXL
    Chicago, IL
    Available Now
    𝐁𝐄𝐋𝐋𝐀 𝐀𝐍𝐆𝐄𝐋🏆🥇💋 BIGGEST TS COCK IN TOWN, PRETTIEST TS GIRL REAL 9 INCHES🍼 YOUR ULTIMATE TS FANTASY Top Elite Model Genuinely Hot, Feminine, Super fit and Hung 🔥 Welcome FIRST-TIMERS | GFE and MISTRESS Experiences | BDSM | COUPLES M/F | VIDEOCALL ★ Brazilian /Italian model 🇧🇷🇮🇹 Based in Londo
  • Rozlyn
    Chicago, IL
    Available Now
    I’m a fun loving girl open minded and ready for new adventures I’m now available for FaceTime sessions call https://www.instagram.com/Rozlynrepublic/
  • NoirSwan
    Chicago, IL
    5 hours ago
    Your intimate, taboo fantasies are celebrated here! *my blurred face pics are my pre-surgery* I am masked at all times in real life My expertise is being a Dominant Kinky Girlfriend Mistress, there is nothing I adore more than being worshipped, pampered, and being around submissive lovers and sl...
  • TSCristal
    Chicago, IL
    6 hours ago
    HELLO 👩🏼 🌹 My Name is Cristal, I'm a Very Passable Latin Gurl, 24 years Old, 5'3 ft 130 lbs 7" in FF Versatile. 🍆💦 "I CAN GIVE YOU THE BEST NICE & RELAXING ***" 💆🏻‍♂️ Love First Timers, Straight & Mature Men Welcome! Call or TEXT For a Faster Response!! ->> ☎️ 773-426-1145💋💋💋💋💋
  • AsianTsRaven
    Chicago, IL
    Available Now
    Hi guys! My name is Raven and I'm a Filipina Transwoman. Dont miss your chance to meet me and make your fantasy into reality! Feed your fantasies and satisfy your senses.