Windsor, Ontario Sex Ads and Adult Classifieds

Windsor, Ontario sex ads and adult classified listings. Select your location below to find adult dating hookups near you. Browse our listings of straight, gay and lesbian dating ads along with trans and swingers classifieds. Many advertisers desire no strings hookups. Others seek occasional or longer term dating arrangements. Search or post for free in BonePage sex classifieds!

Home / Dating

Show Ads In: Barrie | Brantford | Belleville | Chatham | Cornwall | Guelph | Hamilton | Kingston | Kitchener | London, Ont. | Niagara | Ottawa | Owen Sound | Peterborough | Sarnia | Sault Ste Marie | Sudbury | Thunder Bay | Windsor | Toronto

  • September 20th, 2025
  • Shy femme needs love from butch woman in Windsor Femme for Butch in Windsor Hello. I am Jemma and I am 24 and very shy. I work Tuesday through Saturday and so my weekends might not be the same as yours. I hope you can accommodate me. I would like to meet a butch lady who looks so handsome, has short hair and long fingers. Please send me a messag...
  • James is My Name and F#cking Your Brains Out is My Game! Don't underestimate this Italian/Lebanese twink from Queens. Well endowed top boy (and bottom) will make you tap out and take you to the limit tonight or any other night! I got the endurance to back up my claim and a whole lot of tricks up my sleeve for the right guy. I prefer older bears, but if yo...
  • Good girls don't, but I DO! Tania Needs Hot Man in Windsor You can call me a good girl all you want... but that won't change my horny ways. I need more! I need to be touched, I need to be filled, I need to be spanked! Any men in Windsor who feel me on this? Let's get together and see about some NSA tonight and if it works out...
  • I Need a Sexy Man to Tame Wild Willy! Hung Windsor Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Windsor with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks and see a ...
  • Looking for Kinky, Fun, BDSM Sex at Random Times, Must be Discrete!... S&M for Sissys in Windsor I am a gay male, bit of a thugish/bear into all sorts of BDSM, Fetish, Kink and some role play. I host and am seeking sissibois, twinks and queens for some extra sensual and painful fun. Your welcome, my pleasure! I have all the tools necessary in my Windsor dungeon to...
  • exciting black guy waiting for you Exciting black guy in Windsor I am Herman. I am an active and fit, age 32, black male and I am excited to meet you! Looking for lovely lady of any age but not too young to understand my humor and not too old to keep up ;) I am fit and fast to run with and muscular. Tall and attractive. Want to work...
  • Mark, 33 Love country music and driving my truck Hey, the name is Mark and I am a country boy now living in Windsor, age 33, a mechanic and I love to drive my truck out on the open roads. Sometimes I take a blanket and a beer and hang out at my favorite lake a few miles from my house in the Windsor area. I am self sufficient and I am wanting to me...
  • Lesbian horse lover wants to meet same Hello girls! I am Sammi and I love my horses. I have three equine companions that I love to ride on weekends and evenings. I enjoy sunset rides and one of my horses is waiting for a co-rider to come out with me. Are you my special lesbian cowgirl? Beginners welcome. πŸ˜‰ Send me a private messa...
  • Road Head Sally Drivin' Hard in Windsor Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Windsor. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or park...
  • Biker Looking for His Wild Child... Any biker chicks out there who love to ride? Are you more old school into rock, partying, having good times and traveling? If so, then take a look at my profile page and if you like what you see then I want to hear from you. A simple Hi could get this whole train a rollin'. If you live in or near th...
  • Super hot guy waiting for girl of my dreams Black Man for Romantic Woman in Windsor Dark chocolate man with romantic nature. My name is Dwayne and am 6 feet 3 and well built. I am into sports and I love watching football. Life is good and all but I want to meet a beautiful woman for passion and adventure. Check out my profile @DwayneSeekingR...
  • Tantalizing Tina with a HUGE W33NAH! Windsor Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Windsor 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 me: 2...
  • Spanish Speaking Handsome Guy Hola a mis chicos. Estoy buscando a un hombre que esté en forma y musculoso que le guste jugar y comer. Me encanta cocinar. ¿Quieres que te prepare la cena? ¡Lo haré! Golpéame. @ChicoGuapo32 Hello my guys. I am looking for a man who is fit and muscular who likes to...
  • Down to earth mamma with dirty sense of humor Ok, so this is my first time doing this. Yeah I know, everyone has to have a first time, so here goes: My name is Sue and I love movies, food from around the world and traveling. I have only be living here in the Windsor area for 3 months and have not had a chance to meet many people yet. I want to ...
  • DON'T MASTURBATE ALONE! Let Me Get You Off! LET'S GO CAM-TO-CAM! Don't Masturbate Alone... Get Off With Me! Want to chat live cam to cam before you hook up? Talk about anything. Share your wildest fantasy! Ask me anything. Me and my girlfriends are home alone and we enjoy getting naughty on cam. Join My Cam Free! Avai...
  • Irish eyes are smiling in Windsor Hey guys, I am Sean, 27, fit, fun, and freshly landed in town with a cheeky grin. I'm a fun fella, moved here to the Windsor area recently and looking for fun lifestyle and fit guys to hang out with. Go ahead and message me and check out my profile @IrishSean27.  I’m a laid-back gentlema...
  • Don't Worry I Bite! Feisty redhead trans in Windsor 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 m...
  • Latina Beauty needs love in Windsor Hola señoras. Soy Juanita y soy local en esta zona. Tengo un trabajo y tengo mi propio auto. Puedo viajar para conocerte si quieres conocerte a mitad de camino. enviarme un mensaje @Juanita4love.  Hello ladies. I am Juanita and I am local in this area. I have a job and I have my ow...
  • Joker and a Smoker... I'm a 30 year old, 6'1, 200 pound hardcore biker living in Windsor and I go by the handle of Joker. Looking for my sexy road queen who preferably smokes too, or at least doesn't mind that I do. All this anti-smoking shit brings out the rebel in me, and if you're like me then we'll get along gre...
  • Lookin' for a Playmate? Let's Make a Playdate!... Sexy Windsor Hottie For NSA Busy student wants a hot and sexy man (preferably a little older and mature) to spend some quality time with in Windsor. I'm a 22 year old white female college student studying hospitality management and love to get out and find a release once in a while with more mature...
  • Aimee in Windsor... I'm bisexual but I love women... Aimee here in Windsor looking for a lesbian who is Fun loving ,caring, sexy ,freaky, lovergirl like me. I'm always up for an adventure if it's sexual, travel, food or you name it. I"m 30 years old, brunette, blue eyes, high sex drive, employed and have a cat. I will be happy to answer any questions ...
  • Ebony Queen New Here in Windsor Hello, my name is Andrea and I am half ebony and half Texan by birth! I am lonely and new here in Windsor and I would love to meet someone who can show me around and give me a tour. I'm always down for a good time! Please message me (AndreaEbonyQueen) for a meeting....
  • Superb Shemale in Windsor... T-Girl for NSA Encounters in Windsor When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Windsor. 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 and ...
  • Lesbian, Bisexual & Bi-curious W4W Heat! JOIN FREE FEMALE ON FEMALE HEAT! Local Lesbians, Bisexuals & Bi-Curious Women!  SIGNUP FREE: INSTANT W4W ACCESS! Uncensored PicsSwap Your PhotosLive Web CamsPrivate MessagesSext & Hook Up! View Females | Upload & Swap Pics | Sext Messages "Because sometimes onl...
  • Mature Retail Manager looking for Serious Relationship Retail manager seeks serious relationship in Windsor My lifestyle doesn't make it easy for me to meet people. I have recently moved here from Montana and I would love to meet someone who is light-hearted, fun, carefree but also responsible and intelligent. My name is Mandi. I'm 41 years old and I ...
  • Achin' for the Bacon in Windsor Let's Start Makin' Bacon! Hi all, Sheila here in Windsor, single, a bit old fashioned, a little rowdy, love to ham it up, (sorry about the bad pun) 5'5, 140 pounds, 24 years old, big chested, blonde, blue eyes, love dancing, love beer, smoke but not 420, love animals, have a dually pickup and am a ...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Windsor Secret Crossdressing Hookups in Windsor 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 gar...
  • Latina Therapist to help you Latina Sex Therapist in Windsor Rest and relax under my gentle hands and feel the tensions leave your body. Latina woman, a caring sex therapist, seeking genuine adult conversation and romance.  Text or message me online! TherapybyMaria   Sexy Therapy by Maria Send your photos ...
  • Not exactly out yet. Need discreet NSA... Mixed mexican/white male 29yrs, professional divorced with two kids. I am looking to explore my bi-sexual curiousity in the Windsor area with the right man and see if there is anything there. If you can be discreet and are interested then please come see me by clicking here....
  • SciFi lovin' guy getting lonely in Windsor I love SciFi TV and movies. I am Will. I am 31, tall and muscular with light brown hair, grey eyes and tan skin. I work and I have a nice home and car. I never seem to have time to get out and mingle. I need a friend with benefits! Send me a private message to @WillSciFiFan if you want to swap ...
  • Hot stuff hoping for her sugar daddy Hot Stuff for Sugar Daddy in Windsor Hello gentlemen, I'm Kayte. I’m sexy, flirtatious, sweet & fun loving with a very wild edge. I am 5'4" with silky black hair. I am your ultimate hot girl next door, but with a very down to earth vibe. Let me spoil and mesmerize you!  Exclusive su...
  • I usually root for villains... BadBetty big boobs here in Windsor with a sailors mouth and a dirty mind to match. I'm a lesbian female 32 years old, mixed races, 38D cup, big nipples, brown hair and eyes, 5'7, 150 pounds, little salty and horny AF. I want you to swab the deck tonight and then do it again till everything is ship-s...
  • Want to touch my amazing... Wookie? Me, black gay male seeking local men to date, hang with and have some good times. Up for pretty much anything. (love body rubs) 5'10, green/blue eyes, 30 yrs old, well endowed and always ready if you know what I mean.  lived in Windsor for most of my life. I am a city worker so a l...
  • Newly Out Looking for love Newly Out Lesbian in Windsor I have only been out for a few months and I am totally new to the dating scene. I have no idea even what to say or where to start! I will tell you a little about me. I am a youth worker and I have a college education. I am 26 and sort of tomboyish but I do wear make up ...
  • My name is Shey and I am a goddess of love Black Woman for Sex in Windsor I am an African American with a hot body and a clear and quick mind. I want to meet a man who has a quick wit, an intelligent demeanor and a smart mouth. Go ahead and chat with me @EbonyQueenX to see if we hit it off....
  • Partners in crime, or? Sexy, Slytherin, Aries, ISTP and more, if that gives you a hint about my personality traits. So, I’m a sexy, sensual, tender, animal loving, bookworm. I am a bit of a flirty whore, who loves mystical magical movies and stories, so let’s get that out in the open. If you live in the W...
  • Oil Me Up and Rub Me Down Baby! Desperate - Need Massage in Windsor! Cindy here in the Windsor area waiting anxiously for your next shippment of oil to arrive so I can come over for a body rub. Hope you ordered enough to get us through the night! Well, that's ok cause I ordered some of my own for insurance. lol I have a few probl...
  • Any Sexy Couples in Windsor Want to Hookup? - Asking for a Friend πŸ˜„ Inquiring on Threesome in Windsor I'm really horny, I mean I'm really Hannah here in Windsor and you see there's this very close little friend of mine who is bored and lonesome. She wants to know if there are any hot swinging couples around that might be kind enough to service her once in a while. ...
  • Hello! My name is Alexis in Windsor Sex Hookup in Windsor If you are looking for someone to entertain you and be your ultimate fantasy girl, that is me. I am hot and sexy and want to hook up with someone with warm feelings and a bright personality.  Send your pic for mine.  AlexisXoXoXo If this ad is online then I'm availa...
  • Love Giving Head!!! Hey all you hot men in Windsor! I'm OralAimie the best at giving mind-blowing head because I love it so much. But then who doesn't love it right? (if we're being honest) Lots of girls say they don't love it, but they are liars! There is nothing like it and every one is different. Long ones, fat...
  • Ebony TS Playmate for Men Who Know What They Want πŸ–€πŸ†  If you are the type of person who does not want to waste time with games or small  talk… we are already off to a good start 😘 I am a sexy, curvy TS  babe who loves attention, loves giving pleasure, and lives to be desired. I will come looking like  a dream and be read...
  • Sweet Guy with a Naughty Side πŸ˜‡βž‘οΈπŸ˜ˆ Searching for My Queen Windsor Hey there, lovely ladies of Windsor! My name is Romeo and I'm on the hunt for my very own Juliet. Are you ready to be swept off your feet by a modern-day romantic? Look no further because I'm right here waiting for you. Swap pics & contact info WindsorI may not have a balcony to profess my ...
  • Lesbians in Windsor Message Me πŸ˜»πŸ’¦πŸ‘… (W4W) Ladies whowant lesbian sex NO MEN Please.. Looking for a sexy lady to play with tonight, W4W Women only please, I'm strickly lesbian. I love pussy. i'm local and ready to play.. So if you're a lady who wants to play with another sexy lady, hit me up.  ...
  • I WANT TO CHEAT-ONLINE NOW 🟒 I'm tired of my husband. He just doesn't make me happy anymore. I really want to get out and see what kind of sneaky fun I can have. Do youlike the idea of us getting out together and not telling anyone? I know I do, I'm wet right now even just writing this. I want us to have som...
  • WindsorπŸ’• Let’s Grab Drinks & See Where the Night Takes Us  Lesbian Lady here, seeking a fun and outgoing lady!!... Oh hey babe, I’m a sweet little flirt, I'm from Windsor and I like cute cocktails, deep convo and  making out in the back seat secretly. So I think we should meet at a cozy lounge or rooftop  bar and get a strong drink or ...
  • 🧁 🍰 Thick BBW: Naughty, & Ready to Please 🍭 🍬 Let’s Make This Fun! Heya babe do you seek the embrace of a bbw goddess in Windsor? Look no further! With my irresistible curves and insatiable appetite for pleasure, I'll fulfill your deepest desires. Picture running your hands along my soft, chubby frame, reveling in the warmth and sensuality. Let's escape reality tog...
  • WindsorπŸ’‹ TS Tina – Your Naughty Escape, Anytime, Anywhere 🌎πŸ”₯ Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world 😘 I possess the right amount of softness while maintaining the perfect playful demeanor and I always welcome men who understand how to treat a genuine wild wom...
  • Nice Guy? Yep. Push-Over? Only When You’re Behind Me πŸ˜‰πŸ’¦ I'm a hopeless romantic at heart, always looking for ways to show my affection and make you feel like the queen that you are. πŸ’– I believe in chivalry and treating a lady right, so get ready for some old-fashioned charm mixed with a modern twist. Swap pics & contact infoSo if you're ready...
  • πŸ†πŸ’¦ Canada Shemale I Need to Date a Sexy ManπŸ†πŸ’¦ Canada Shemale ReadyNeeding sex here in Canada Canada πŸ“²  Transsexual Dating App  I'm new to Canada from America, but I need a sexy man to date and have some sexy fun..  I'm a transsexual or sometimes reffered to as a Shemale and I have a nice big cock for you.. Would you like to ...
  • πŸ’ͺπŸ† I'm All Tha Chocolate You Could Need πŸ’ͺπŸ† Hey I'm new to dating sites but I'm ready to give it a try and see who might message me. I'm wanting to get out and have some fun. Yes I'm black and yes I have a thick πŸ† but I'm so much more than that. Also I want you to know that I love all shapes and sizes of men, I just want someone I can conn...