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!

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  • April 30th, 2026
  • Cuckhold Bull in Windsor Available for Couples... Hello, I'm Ryan and live in Windsor offering my unique service as a Cuckhold bull. I have the physical credentials and am attractive. I stand 6'0, good shape, 9"+ inches, thick and uncut, single, black hair, blue eyes and I am a very easy going guy.  Respect and attentiveness are my watchwords...
  • Age 47 Regular Guy with a Lot to Offer!! Man Seeking Woman for Dates in Windsor Hey, Richard here. I just want to say hi to you and hope you might check out my profile and see if you want to go out for a date. I am just a regular guy looking for a regular gal. I've been single too long. I keep busy and have a great life but It's time to m...
  • Chill Bearded Guy Looking for a Fun Connection ๐Ÿป๐Ÿ˜‰ I'm a relaxed 30 something. Fair amount of face hair, cheeky sense of humour and love to laugh at the most unexpected moments. By day, I'm a working parent and by night, I love to socialise. Let's plan something fun and go out! Im a pretty chill girl who just loves to hang out and talk. Im a respon...
  • 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...
  • DIVORCED๐Ÿ‘ฉMOTHER-MILF?? I am available Every day. Make me CUM and this could be a regular thing. If you want test me in SLIM mom try today now anyone.100% real and legit ๐ŸšซNO GAMES ๐ŸšซTIME WASTERS ๐ŸšซNO DRAM Respect me and I will respect you! I just need some oral hookup all day/night .I can host or come to your p...
  • Intoxicating-Stacked Blonde Beauty in Windsor... Hello men, I am Korina a single woman seeking a single sexy man for NSA relations in Windsor. About me: Russian born, 25 years old, 5'7, 130 pounds, 38D cups have been here for 10 years and have a small business. Do you live in Windsor? I try different places for finding attractive sexy men, but not...
  • Do you know the difference between a dick and a bucket of popcorn? You don't know? 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 Windsor tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than...
  • Karaoke queen loves singing with her Knight-ess Carmel Karaoke Queen in Windsor You love to sing karaoke? Good!! Me too!! My name is Carmel and I adore singing. I am not shamed to say I am probably not so good but after a drink or two you probably won't care! I love singing modern pop, 60's and 70's disco, and even some modern rap. Message me wi...
  • OLDER BABES for YOUNGER MEN!! Older Women for Younger Men Sexy older babes show younger men how to truly please a woman! Women Join Free | Men Join Free | View Photos  1. Join Free for instant access 2. Chat or sext with members 3. Arrange local hook ups! More&nbs...
  • Angelic and single with big tits that love attention! Hi guys, my name is Trisha and I am 24 and wanting to meet a cool guy who likes live music and hiking. My breasts are one of my best features so I hope you like them! I'm pretty cute to look at too. You must have a good sense of fun and be intelligent and responsible. My measurements are 38-26-36! ...
  • Naughty & Nice Rubs... She's Naughty and I'm Nice! Windsor Massage Girls Here in the Windsor area we have formed a team to please even the most demanding men of taste. We are Naughty and Nice or Carine and Inga. Sort of like the good cop/bad cop routine except we are here to make you feel good. We apperciate how life can wear on you guys and so we ...
  • Island Girl With a Playful Smile ๐ŸŒบ๐Ÿ˜‰ Hi! My name is Leilani. Well, I am very relaxed, very island and I love to laugh. I love to have fun in the sun. I like to meet confident guys. Open to good energy and a laid back vibe. Friendly, curious and here to get to know you! I'm new to Windsor from the island and I want to get out and have s...
  • Email Windsor Shemalesโค๏ธโ€๐Ÿ”ฅ I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...
  • Smokin' Hot and ready for a date! Ok, so maybe Smokin' hot is something you need to decide, buy hey, I have a sense of humor! Seriously though, I do think I am quite attractive and I have certainly been complimented often. My hair, especially, gets a lot of attention because it goes way down my back and I sit on it! It is long and s...
  • 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 ...
  • 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...
  • Bi Swinger Vibes ๐Ÿ˜ Open to Couples Who Play Together in Windsor My Bi-Curiosity drives me toward men and couples who truly enjoy each other's SEXY company. Bold by nature, I lean into depth when exploring how love plays freely. Confidence matters here - especially willingness to engage without hesitation. Attention flows best when shared without holding back. Th...
  • New to the Windsor area and lonesome! I am new here in this town and I would like to meet handsome gentleman to go to dinner and on date with. You are interested in me please send message to me. @RagazzaSexyX Sono nuovo qui a Windsor Sono nuovo qui in questa città e mi piacerebbe incontrare un bel gentiluomo per andar...
  • I'LL DO ANYTHING YOU WANT ME TO...๐Ÿ˜ˆ๐Ÿ˜ˆ๐Ÿ˜ˆ Hey babe, I'm Julie and I'm new here. I need a fun man to have some naughty fun with. I love to ๐ŸŽ‰ PARTY ๐ŸŽ‰.. maybe drink and more ๐Ÿ˜‰ Then while we're having fun partying, we should fuck and fantasize. I love dressing up ๐Ÿ‘—๐Ÿ’„ I love pretending to be whatever you want me to be. I want us to...
  • Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Windsor? Hey, I am Jasmin, with a great body and busty. Hit me up @SweetJasminT. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for a fun date and see where it goes! I'm preop and functional, very sex positive and love all sorts ...
  • Hungarian Beauty seeks fun and friendship and more Hungarian Woman for Fun and Friendship Új vagyok ebben a városban, és magányos vagyok. Szeretnék találkozni és randizni valakivel, aki szórakoztató. Küldj egy üzenetet, ha el tudod olvasni ezt. Beszélek angolul. I am n...
  • Mature Wealthy Man Looking for Twink Boy Toy... Hello boys I'm Tony 48 years old and been out for 10 years now and take good care of myself. I'm from Cleveland originally, but moved to Windsor to start over again after my divorce. I don't really have any baggage with the kids being grown up and off to college. I plan to retire very soon and want ...
  • Tattooed Alt Girl Seeking a Chill Guy ๐Ÿ–ค๐ŸŽถ Well I've got black hair, loads of tattoos and I LOVE music. So i suppose you could say that my lifestyle is quite alternative. My name is Raven and I'm a chill, alternative, down to earth, honest and true girl. I'm all for just taking it easy and having fun. Sometimes I just want to have a good nig...
  • Keep Calm And Have A Threesome in Windsor! Swinger Couple in Windsor I'm Daily and my hubby is Don, we are in our 30's, live here in the Windsor area and are swingers looking for a sexy man and or woman. We love role play as you can probably tell from our pics. We can be a little kinky I suppose, but mostly we are into adult role play and N...
  • Let's indulge ourselves in something extraordinary... Hello there boys I'm Tawana a 24 year old ebony female seeking a sexy man for some hot NSA in Windsor. I'm actually from here and prefer a man who lives here instead of a long distance thing. Mostly because when I'm hot and ready and I need you I'm gonna need you now, and not whenever you can get he...
  • Looking 4 a Man 4 Sex ๐Ÿ†๐Ÿ’ฆ & Fun๐Ÿ˜๐Ÿคฉ I really need to get out and have some fun, maybe a drink, smoke.. Sex -  Message Meโค๏ธ I've been really horny and just stuck at home. I have a few GF's who might want to join us and play too, if you're down Or I'm willing to go out and have fun just us. Will you help me get out and have so...
  • Fetish Swingers W an Appetite in Windsor - And YOU are on The Menu! Fetish Fantasy in Windsor Let us introduce ourselves, we are Gale and Ronan, swingers and fetishistas here in Windsor. We are def looking for a single guy or girl to join us in some adult fun. We are into threesomes, foursomes, kink, fetish, bondage and other assorted kinds of BDSM. The degree to ...
  • Englishman Without His Butler... It's a hard life for an Englishman not to have his butler in America, but I have learned to adjust. The really hard adjustment is not having a good woman and best friend. Moved here to Windsor about 3 years ago from London to work in the tech industry and do rather well despite the sky-high prices a...
  • Click here - Add to Cart. Windsor Single Dad for Fun That's my mom in the pic with me BTW. I'm Jonah here in Windsor a single working dad age 31 with a three legged cat and hope to find a woman for some NSA fun who has a big purse to get lots of snacks into the movie theatres. I'm not afraid to talk about Bruno, or yell Yab...
  • Wild and Crazy Girls Looking for Some Man Meat in Windsor Bi Girls Want Threesome in Windsor Hello boys we are two bi girls (Linda and Emmy) looking for a sexy man in Windsor to join us in some hot fun. We tend to be a little kinky so you'll have to get to know us a bit first. You check us out, and we check you out sort of thing. Come on, it'll ...
  • Are You Uber Horny? I AM - Maybe We Can Work This Whole Thing Out Together!... Nympho Seeking NSA in Windsor I am Tory, a 24 year old, brunette living in the Windsor area, 5'5, medium build, told that I'm fun, easy to be around, a good conversationalist and have a sexy relaxed vibe. Do you live here locally, find me attractive and love big playful titties? Then I might b...
  • Chocolate D'Light Body Rubs in Windsor... Windsor's Black Lesbian Masseuse Hi ladies I'm Lola an ebony masseuse in Windsor offering both erotic and theraputic body rubs for women. Just tell me which one you want, happy ending or not. I'll be pleased to go either way. I want you to be satisfied and come back for more. I host and have f...
  • Young, Fun, Perfect body and 36DD looking for nice gent to date Young, Fun, Perfect Body and 36DD 26 yr old looking for fine looking man, with fit physique. Must enjoy sex! I like being active and enjoying life. I'm giving online dating another try. My Pics and Contact Info 36DDblonde Send your photos and mobile# for mine. Tell me a little about yourself...
  • BBW Lesbian in Windsor Sucker for love BBW Lesbian in Windsor Hey ladies, My name is Joanne and I suck at love! Ok, what I mean is, I love to suck. Definitely a 'boob' woman and if you got em I like em. Big, small or medium, it doesn't matter. I'm ready to spoil your body! Message me @JoanneBBWfem. Serious dates only please. Send y...
  • Tattooed Student ๐Ÿ˜ˆ Who Dates Older Men Inked. Curious. Not Into Boys. ๐Ÿ–คโœ๏ธ   Yes, I’m a student. Yes, I’m tattooed.And no, I’m not into guys my age. ( MESSAGE ME NOWโœ‰๏ธ_) I like men who are settled, confident, and don’t get weird about ambition or ink. Experience is attractive. Calm is sexy. Tryin...
  • Amazonian Warrior princess looking for her Xena Tall Woman for Woman in Windsor I'm a soft butch bisexual/pansexual woman. I enjoy cosplay and RPG. You wanna role play with me? My name is Terri and I am 5' 11", medium/athletic build and I have long dark hair. I am fit and muscular from working out regularly. I'm interested in all types of women ...
  • Asian Beauty likes a nice massage My name is Aiko and I am from Japan. I like to meet a girl who likes massage to give and receive. I am attractive and sensual. I want to meet you. I am shy at first but very willing. Please message me online for my photos and more information.  Kisses ๐Ÿ‘„ AikoFemme Username: @Aik...
  • Slovak woman lonely and looking for guy in Windsor Dark, sultry and tall, very well built, Slovak woman is here to please and be pleased. I desire for long term friendship, fun and love. My English is getting better so send photos and message me here @TmavoZmyselná Tmavá, zmyselná a vysoká Slovenka   Tmav&eac...
  • I Melt for Men Who Lead ๐Ÿ–ค Windsor A woman who really needs to be dominated and disciplined!! I move and do whatever you want, I aim to please and do whatever it is that I'm told (NOTHING IS OFF LIMITS FOR YOU). What holds my attention? Peaceful firmness, lively drive, even just the quiet sense that choices slip into place without ef...
  • Handsome Butch looking for Fem Beauty Butch Lesbian for Fem Beauty in Windsor My name is Mikayla but my buddies call me Mikey. I am 28, soft butch woman, working full time and love to ride my motorcycle. I am interested in meeting a beautiful soul who likes to feel the cool breeze in her hair from the seat of a motorcycle heading down ...
  • Sexy hung and big busted Hung and Busty Shemale in Windsor Tammy, 39, big tits!! Well hung, everything works, clean and so cute!! What more could you want in a gurl?!! How about you message me @Tammy39T and we can talk and meet! Send your recent pic for mine. Username: @Tammy39TLocation: Windsor, OntarioAge: 39G...
  • Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Windsor 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 and show you what...
  • Windsor's Sex Ninja Has Come to Your Rescue... Single Guy 4 FWB in Windsor Hi I'm Carl, and maybe the part about being a ninja isn't quite true, but I do have a yellow belt in Karate or was it Judo? Anyhow, I'm living in Windsor and am looking for something more long term with the right lady. Me, I'm a black male, 31 years old, 5'10, 180 p...
  • Alex's Huge Throbbing Cock in Windsor ๐Ÿ’ฆ๐Ÿ’ฆ New to the scene, willing to try anything! Thanks for checking my ad. I'm new to this. My name is Alex (hmu @AlexThrobbingCock4u) and I love fucking and getting my huge throbbing cock stroked and sucked to completion. I'm single but not totally out yet so please be discreet. At the same time, I'm a...
  • Help! Single and Got That Tingle! Itchy in Windsor Hey there boys I'm Natalie here in Windsor looking for a handy man to take care of some of my feminine needs. Are you talented enough to scratch my itch? Must be skilled, but might take on the right apprentice who has potential. I'll have to keep you on call, because a girl never k...
  • Couple of Kinky Girls Looking for fun!! ๐Ÿ˜˜๐Ÿ”ฅWindsor Hey there, I'm Noelyn from Windsor and my husband and I are a sexy swinging couple looking to add some spice to our already steamy relationship. We love the thrill of meeting new people, exploring new fantasies, and indulging in all the pleasures that the swinging lifestyle has to offer. ๐Ÿ“ฉSwap Pi...
  • looknsee - BBW - Brings a Lot to the Table in Windsor... BBW For Hookup in Windsor Hola in Windsor, I am Emma sunshine mixed with hurricane, the type of woman that works and plays hard. I enjoy every second of my free-time. That usually entails being around the people I enjoy, playing with babies, dinner, and drinks, and lively conversation. That&rs...
  • Tall & Peggable ๐Ÿ˜ˆ๐Ÿ’‹ Looking for My Boss Babe Hi I am a Single 32 years old straight white male.I'm in Windsor and I would love to meet and amazing woman who wants to feel a real man! ๐Ÿ˜‰ I love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very oral i love to give as much as receive. I love to make her cum all ov...
  • Cute TS Sugar Baby Seeking Male๐Ÿ’ŽAria Username: @AriaSweet Trans Friendly: Yes Private Meetups: Yes Phone Chat: Yes Pics Available: 18 Message me if you like feminine Transsexual ๐Ÿ’ฌ Hello, I am AriaTS here in Windsor. A very sweet and very feminine trans-girl that loves to be your sugary little sugar-baby, accompanied by a man t...
  • New in Windsor. Lesbian Bondage Anyone? My name is Michelle and I am ready to meet the girl of my dreams to explore the world of bondage and light BDSM in a safe and erotic setting. Send me a private message if you would like to swap pictures, chat and meet up. Attractive, fun, slim build, light hair. Let's see where this leads us!! Us...