Winnipeg, Manitoba Sex Ads and Adult Classifieds

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Show Ads In: Winnipeg | Brandon

  • January 28th, 2026
  • TS Sugar Baby 💎 Femme, Flirty & Looking for the Right Man in Winnipeg I’m a transgender sugar baby who loves femininity, attention, and being appreciated by a confident man who knows exactly what he wants.. Confidence speaks louder than words. Gentle touches matter more than grand gestures ever could. Let's Link Up Babe - Fond of the sugar dynamic. Getting pamp...
  • Help - Can't Afford a Masseuse in Winnipeg! Busy Girl Needs Body Rub in Winnipeg Mmmm... touch me baby! I'm DeeDee a waitress in a very busy restaurant here in Winnipeg. I work day shift when all the older crowd and construction workers come in and it's hard to meet guys my age. When I get off I'm soooo sore from carrying heavy trays and my ...
  • Nice Guy? Yep. Push-Over? Only When You’re Behind Me 😉💦 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. 💖 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...
  • Chubby Asian Sweetheart 💗 BBW Curves & Real Connection in Winnipeg I’m an Asian BBW, Comfort matters when dating - so does laughter and a spark now and then. Quiet by nature, yet full of self-assurance, I enjoy closeness without needing loud displays. At ease with who I am, I welcome warmth if it feels real. If rounded shapes or steady presence catch your eye...
  • Latina Mom Heat 🔥 Sweet Smile, Dangerous Curves in Winnipeg Latine Mother by day, freaky by night 😈 Living between duty and wanting more. During morning hours, tasks fall into place without effort. When darkness arrives, another version emerges - light on her feet, slight smile, just enough curiosity. 😌✨ MY LATINA MILF DATING PROFILE📩 Warmth flow...
  • Vibrant and Intense 26 year old wants to meet sexy dude Hi! My name is Angelina. My body is in great shape and I like to exercise and stay fit. I am fun-loving and down to earth. Would like to meet same in the perfect guy. I love swapping pictures and sext messages on mobile so don't be shy. I think swapping pics is the perfect way to set the tone for a ...
  • Help - I'm a Nymphomaniac AND an Insomniac - There is Only One Cure! I'm sort of a reverse Sleeping Beauty story. lol I need lovin to put me to sleep and give me those feel good endorfins. I want to find a sexy man to hookup with when the need strikes me. Of course you can let me know when the need hits you too. This isn't a one way street after all. I'm 29 years old...
  • Fit Swinging Couple in Winnipeg, New to the Swingers Lifestyle & Ready to Explore! Swinging Couple in the Winnipeg, Manitoba Area Hello sexy people! We are a swinging couple in the Winnipeg area. We are new to the swingers lifestyle but eager to learn and experience the passion! We assure we can give passion as well as we receive it! About Jeff Jeff is former military, stocky, ...
  • WE CAN HOST OR COME OVER 💥Winnipeg🌟😉 Hey there, I'm Shari from Winnipeg, and my husband and I are a fun-loving swinging couple looking to connect with like-minded individuals who share our passion for the swing lifestyle. We love the thrill of meeting new people, exploring new experiences, and indulging in our deepest desires together....
  • Chunky Monkey looking for Hunky Tomboy Chunky Monkey Fem for Hunky Tomboy I am nice and curvy but not heavily overweight. I am looking for a chick who is handsome and butch but with some feminine qualities. Like it's ok if you cry at a movie! lol. I am 21, work full time and drive my own vehicle. I am looking for the right gal to make m...
  • I’m a Sexy and Naughty T-Girl Here in Winnipeg. Winnipeg T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Winnipeg 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 and ...
  • January 27th, 2026
  • Sensual Dating Sensual Dating with Jen Wanting to date sensual caring man. I will do things the way you like. I like super open minded guys who show respect. Kink friendly!!!! Just pm or text please, no calls. My contact info is here SensualWinnipegJen Open minded Kinks welcome Femdom  420 frie...
  • Gay Russian Bear New to Winnipeg... My English is not so good yet. I am Vlad from Moscow, Russia and want to find gay young man for sex in Winnipeg. I am 34 years old, 6'2, 210 lbs, blue eyes, big size penis, not cut, stay in good shape and love good party.  I am here for 3 years, engineer and single, but still no car. If you ar...
  • Petite Winnipeg spinner girl for threesome... Little Bombshell in Winnipeg for Threeway Hi ladies and gents I'm Jamie and I'm looking for a FWB situation with a hot couple who lives in the Winnipeg area. (willing to travel) As the title implies I am petite; only 5'1 and about 100 pounds. I am 22 years old, Italian, hot blooded and love to ride...
  • Hot and kinky MILF looking for some fun in Winnipeg Winnipeg MILF For Kinky Hookup! Hi all you sexy Winnipeg guys, I Georgia and I am an slightly off beat working professional mom of two. MILF. Just looking for some sexy fun and to explore my (and yours?) kinks and fantasies, FWB. I am into men, but possibly women or even a hot couple depending...
  • Love Giving Head!!! Hey all you hot men in Winnipeg! 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, fa...
  • Nascar fan looking for lady to have fun with Nascar Fan for Lady in Winnipeg If you are looking for someone legit, hit me up for a date. I am a down to earth guy who likes to chill on weekends and do fun stuff. I enjoy dining out, concerts, live theater, strolls at the park, hiking, movies, sports and much more. I hope you have a good sense o...
  • I Need a Sexy Man to Tame Wild Willy! Hung Winnipeg Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Winnipeg 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 ...
  • Penny for your thoughts? Penny TS in Winnipeg 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 @PennyTSswitch!! I'm a mixed race sweetheart, looking for a nice man who will enjoy being with me. Let's enjoy having some fun, hot dates and e...
  • Hot Latina looking for love Latina caliente buscando amor. En la música de fiesta, jugar, acampar en la puerta y todo tipo de diversión física. Me Text para una cita! @latinacaliente27 Hot Latina looking for love. Into party music, playing, out door camping and all kinds of physical fun. Text me for ...
  • Submissive and Need a Dominant Sir in Winnipeg Our Little Kinky Secret in Winnipeg Allow me to introduce myself, I am Chelsea here in Winnipeg looking for a Master to give me what a real woman needs. I am into domination, humiliation, bondage, roleplay, gags, whips, toys and am still exploring my fetishes. I'm a professional woman working in th...
  • Hot chick needs female distraction Will you be my much needed distraction? Hello! I am Lucy and I am so wanting to get out and meet someone who can take my mind off things! Are you caring and a good listener and a good kisser? If you are, hit me up with recent pics and a message @JuicyLucyX I look forward to talking with y...
  • Calling all Swingers and Boobsters in Winnipeg Cali Needs Threesome in Winnipeg Hi I'm Cali a single girl 24 years old with extra large boobs here in Winnipeg looking for the right kinky couple who will love'em. You might be boobsters if you know what motorboating is. You might be boobsters if you know more that 7 words for breasts. You might b...
  • Winnipeg Lipstick Lesbian, Hot 'n' Ready for Butch Woman Lipstick Lesbian for Butch Woman in Winnipeg Lipstick lesbian wants to meet an awesome butch woman to share love and laughs. I am 25 and definitely femme. Long strawberry blonde hair, on the shorter side, fit and curves in the right places, but not overweight.  Come and Private send me a...
  • Inviting eyes and seductive thighs wanting to find loving guy in Winnipeg I advertised here in the past and thought I found my true love. Well, I guess not so here I am again.  I recently moved, so I am new in Winnipeg and have no local friends to hang out with. I would love to meet fun, down to earth guy to explore passion and hot sex. I just need to have some fun a...
  • Divorcee looking for exclusive arrangement with generous gentleman Divorcee Seeks Exclusive Arrangement with Sugar Daddy Hi, I'm a recent divorcee seeking an exclusive arrangement with a Winnipeg sugar daddy! I am am 26 years old, love sex and pleasing my partner. I am looking for someone open to all types of fun and adventure! I'm classy enough to take to a busin...
  • 🍁 TS Treat in Winnipeg, Manitoba 🇨🇦 – Prairie Heat with a Wild Side 😘🌾  Hey cutie 💋 As a confident trans girl from Winnipeg I will bring you hot unforgettable fun  during your cold nights. My name is 33 and I have a caramel complexion with juicy thighs and  a playful personality that understands when to behave and when not to behave 😈. My TS FuckBo...
  • Winnipeg Cougar Could be a Cubs Delight Tonight!... Cougar on the Prowl in Winnipeg Hi there you sexy cubs I'm Joan and I'm gonna spoil you tonight! My den or yours, let's get wild in the sheets till I've had my fill. If you are a cub between 18 and 30 and live in the Winnipeg area then I've got something for you. Maybe you thought school was ...
  • Oh, Cumsy Me! Winnipeg Petite Girl 4 NSA I'm Victoria here in Winnipeg and was just sitting here thinking naughty things about you and accidentally had an orgasm and squirted all over the place! Now I have to clean up so I can get dirty again. I'll be ready for you when you get here. Don't you worry about t...
  • F/M seeking love and fun Female to Male Trans Man in Winnipeg My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. This feels right and I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and ot...
  • Winnipeg - Let’s Make Some Mischief… And Maybe a Mess 😉  Hey gorgeous 😏 I’m a 35-year-old guy from Winnipeg with a cheeky smile, strong  hands, and an even stronger craving for adventure — both in and out of bed. My intention is  to meet a woman who possesses confidence because I seek someone to flirt with and share laughter...
  • Tom, 42, wants single minded woman Hello ladies, I am Tom, age 42 in Winnipeg. I have a good job, a new truck and I own my house. Life is pretty good and I'm ready to take the next step toward finding love. Could you be who I'm looking for? We'll never know unless you message me.  I am not looking for someone who is going to gi...
  • I BREAK TWINKS and turn them into MY SEX PUPPETS! Big top bone thug gonna wreck you and make you twinks tap out! Looking for sissie boi to use and abuse here in the Winnipeg area. All is fair and shit as they say. Needless to say I'm the dominant and controlling type in any situation. Your gonna get the big one rough and deep honey! No screamers pl...
  • I'm Danish... Eat ME! Been dating most of my life and nothing too serious, but now I'm ready to settle down with the right person. I'm looking for a woman who will complement me. Where I have weaknesses she will have strengths. She must be local in or near Winnipeg, because I did a long distance relationship once an...
  • Widower seeking affection in Winnipeg Winnipeg Widower Seeking Affection Hello ladies, my name is Jonathan and I am seeking some female company for fun times and affectionate days. It has been a while and I have to face that I'm lonely. I am 52 and still look in my late thirties (I am told) and I am fit and healthy. I love riding horse...
  • DESPERATE SEEKING A REVENGE FUCK! 🥒🥯💦 Newly single Winnipeg 22 y/o female needs a good fuck 💦 Hey there, I'm Trish from Winnipeg. Let's get right down to it. My husband left me and I need to fuck to make me forget about his sorry ass. I'm tired of being neglected so I'm looking for a nice, attentive man to keep me warm tonight. I'm ...
  • Tiffany Shelle - Your Winnipeg Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Winnipeg 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% functioni...
  • Get Over Here Boy! Single and Sexy in Winnipeg Baby! Hannah here in Winnipeg looking for a friend with benefits. Hey just so you know I'm not just another piece of ass. That's not why I'm here, to just add to your body count. At the same time I will not tie you down in a relationship you don't want either. Let's be c...
  • Shy femme needs love from butch woman in Winnipeg Femme for Butch in Winnipeg 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 messa...
  • 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...
  • Black man, 31 needs good boyfriend Black Daddy in Winnipeg area Man, I don't know what I am supposed to say here lol....I am Frank and I am 31, clean, fit and single. I am just recently out of a long term relationship with my ex boyfriend. I won't go into detail but we just drifted apart. Anyway, I'm ready to mingle! Locals only in ...
  • hippy_nomad Loves antiques, rescuing stray animals, 420... Must be 420 friendly. Currently living in Winnipeg I am an honest, hardworking and caring woman who is looking for the same. Let’s face it we’re not getting any younger so who wants to play games- NOT ME! I also like going to flea markets, dancing and most of all vacationing! So if you t...
  • A monster in the sheets, but a lady in the streets... Hello men, I'm Lilith a 27 year old sexy femme, fully functional, passible, sexy and hot to trot trans. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Winnipeg area and are interested then drop me a line and introduce yourself. You can...
  • GAMER GIRL TO TAKE CONTROL OF YOUR JOYSTICK 💋🍆💦 Gamer Girl for Winnipeg Guy I'm Sofie, and I'm a naughty gaming girl looking for some hot and steamy gaming fun in the Winnipeg area. When it comes to gaming I am very competitive. I enjoy WOW, Elden Ring, Hogwarts Legacy, Minecraft, Visions of Mana and more!  When it comes to sex, I love gett...
  • Bring a toy for Kitty (w/batteries) on our first date!... I'm a bit of a goth and have recently discovered the magic of toys. Bring your favorite toy on our first date and I'll bring mine. This could be our Toy Story. Lesbian in Winnipeg seeks female companion for erotic encounters and possibly long term relationship. I'm Katzzy and am 33 years old, 5'7, 1...
  • Winnipeg💕 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 Winnipeg 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...
  • 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! ...
  • Normal But Kinky Couple 😘🔥Winnipeg Hey there, I'm Noelyn from Winnipeg 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. 📩Swap P...
  • New in Winnipeg. 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...
  • 💖 Sweet, Seductive & Craving Her – Ebony Babe Looking for a Good Time 😘 Winnipeg Ebony Lesbian Lover Seeking Woman!!😉 I am a thick, chocolate colour 🎂🤎  , in my mid-20s, with soft curves and  smooth skin, and a wicked little smile. I am playful, affectionate and very into women,  especially if they know how to tease and please.  It should be...