Winnipeg, Manitoba Sex Ads and Adult Classifieds

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Show Ads In: Winnipeg | Brandon

  • November 1st, 2026
  • Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Winnipeg for Man Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will be p...
  • Irresistible woman desiring to be wanted Hello, I am originally from Portugal and would love to meet a handsome, funny guy to do to movies and dinner with. I am new to this online dating scene but hopefully, you will be nice! Please message me @IberianLady1 Olá, sou natural de Portugal e adoraria conhecer um tipo bonito e engra&cce...
  • 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...
  • !!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Winnipeg Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Winnipeg to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Online Chat ...
  • I'm Troy in Winnipeg - Bi-Curious Looking to Experiment... Bi-curious in Winnipeg Hi guys, I'm Troy here in Winnipeg divorced after 10 years and am entertaining the idea that I might like the gay lifestyle. So, here I am on this site looking for a special kind of man who isn't going to go too fast with me. (is patient) Woman say I'm well hung, bu...
  • Wanting slightly older gentleman Hello. My name is Sylvia, age 24 and I am pretty done with young guys who mess around. I want a guy who is mature and kind and likes to travel. Please contact me so I can learn more about you!  Send your recent pics for mine. I just took some naughty pics with my girlfriend Brianna. I think yo...
  • Short and Sweet and New to the Area Hey guys! I will keep it short just like me! I am new in the Winnipeg area and I am single and looking for some dating fun! Send me a message @ShortnSweetKellie if you want to know more! ...
  • 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...
  • 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 ...
  • I am Caroline and I am lonely Caroline Seeks Female in Winnipeg  Hey ladies, I'm Caroline. I have only been living in the Winnipeg area a couple months and as you can imagine I have not had much chance to meet other women. If you are lesbian, bisexual or bi-curious and want to meet me please send me a message and see ...
  • Tattooed Sexy brunette, new in town & craving some fun ๐Ÿ”ฅWinnipeg  ๐Ÿ“Winnipeg GIRLIE SEEKING MALE ATTENTION!!ABOUT ME: A 20-year-old brunette woman who has multiple tattoos across my sexy body... wanting to find someone in Winnipeg to spend time with a special someone while I'm in college. I'm currently studying to be a teacher.. I recently arrived here fro...
  • VirginAss88, Never Been With a Man... I like having fun. I'm very honest perosn, very brave and interilligent. Love it here in Winnipeg and all the possibilities it offers for a guy like me. don't like the idea of bar pickups and would rather ease into this thing. Must be descreet and honest. Message me here. VirginAss88...
  • 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...
  • 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...
  • Chocolate D'Light Body Rubs in Winnipeg... Winnipeg's Black Lesbian Masseuse Hi ladies I'm Lola an ebony masseuse in Winnipeg 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...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Winnipeg Secret Crossdressing Hookups in Winnipeg 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 ga...
  • Hey Ya'll Its a 3-Way Booty Call! Try an Ebony Threesome With Me! Vera here in Winnipeg looking for a few good swingers! Or, at least one good couple. LOL  If you like hot chocolate and a big booty here I am. I got some hefty hooters too that will make your mouth water and hypnotize you so I can take advantage of you. Hit it a...
  • 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...
  • โœ…๐ŸŒˆPretty Sweet GIRL Seeking Men๐ŸŒˆbbfs๐ŸŒˆanal๐ŸŒˆall holes๐ŸŒˆ Hey there, I'm Cally, and I'm looking for someone who's not afraid to explore their fantasies with me. I love getting adventurous in the bedroom and trying out new things. Whether it's a steamy session in the missionary position or getting wild in doggy style, I'm always up for a good time.Swap Pics...
  • MAKEOUT FETISH๐Ÿ’„ Soft Lips, Slow Kisses ๐Ÿ’‹ W4M Makeout Queen Seeking Real Chemistry Do you ever wonder how it feels to kiss someone? The smiles draw me in. A deep kiss sometimes says more than words.  I am a woman. I want to meet a man. I like deep kisses. I want dates where we make out. I hope to feel close to someone. If you want W4...
  • Needed: Single Men and Women For Sexy Swinger Couples in Winnipeg!... Meet Local Swingers and Get Naughty! Thanks to you Winnipeg swingers can spice things up by having a sexy woman, a hot man or even an amazing couple join them in the bedroom for adult fun. Instant Access - Biggest  Selection - Widest Variety Meet and hookup for the best sex ever! ...
  • 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...
  • Goth Girl With a Soft Side ๐Ÿ–ค๐ŸŒ™ I suppose people think that my dark clothing and makeup is scary. But in reality, I am a very shy girl. I just love music, candles and the weird and bizarre. ( View My Pix and Message Me ) My name is Luna and I am searching for some kind of brain or soul mate. Open to individuality and not really b...
  • I'm a Steamroller Baby! Hi ladies, James here nice to meet you! Let's hop on my bike, put our knees to the breeze and do whatever the hell we please! I'm good with my hands, still a bit of an outlaw at heart, 35 years old, lived here most of my life, blonde hair, blue eyes, 6'1, around 220 pounds, muscular, love women, hug...
  • Sweet Guy with a Naughty Side ๐Ÿ˜‡โžก๏ธ๐Ÿ˜ˆ Searching for My Queen Winnipeg Hey there, lovely ladies of Winnipeg! 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 WinnipegI may not have a balcony to profess m...
  • ๐Ÿฅต๐Ÿ†SHEMALE COUPLE SEEKING SOMEONE FOR SEX๐Ÿ†๐Ÿฅต Hello men and women. We're a TRANS couple seeking someone or multiple sex partners to join us. We have cock and tits.. Does this turn you on? We're willing to let you hop in our bed, or we will come to your place. I really love sharing my partner and being fucked in front of her.. OMG I"M GETTING HA...
  • Any Sexy Couples in Winnipeg Want to Hookup? - Asking for a Friend ๐Ÿ˜„ Inquiring on Threesome in Winnipeg I'm really horny, I mean I'm really Hannah here in Winnipeg 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...
  • Jaw Dropping Hot Lesbian Hot Lesbian Seeking a Female Lover in Winnipeg Did that get your attention? I hope so because I am looking for my perfect female partner. Someone fun attractive and intelligent. She should be easy to talk to, fun loving, laid back and attentive to her partner, just as I am. I'm looking forward to h...
  • Exotic TS Beauty Seeking a Generous Gentleman ๐Ÿ”ฅ๐Ÿ’Ž Hello lovely, I’m a beautiful trans girl with lots of curves. I’m a confident woman with a beautiful personality. Here I want to meet with the more successful men. Men who can understand that the beauty is also of the feminine kind. Intelligent men, that can realize that we trans girls a...
  • October 31st, 2026
  • DESPERATE SEEKING A REVENGE FUCK! ๐Ÿฅ’๐Ÿฅฏ๐Ÿ’ฆ Newly single Winnipeg 22 y/o female needs a good fuck ๐Ÿ’ฆ 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 ...
  • Winnipeg๐Ÿ’– Sweet & Seductive GFE Seeking a Real Man Are you looking for that spark that feels real? I am a GFE woman looking for a man that would like to take things slow and get to know each other. Perhaps you are looking for some W4M dating or a Girlfriend Experience. Or maybe you are looking for a local MILF that is looking to get intimate with so...
  • Bryan for Hot Male-on-Male Action in Winnipeg Bryan M4M in Winnipeg Hey guys! I'm Bryan, looking for some hot male-on-male action. I want to meet a guy in the Winnipeg area who is ready to get down and dirty with me. See my pics and contact info @Bryan24m4mX.I'm primarily top but can switch for the right guy. I love getting my big thick cock s...
  • Letโ€™s Flip the Scriptโ€”You Lead, Iโ€™ll Moan ๐Ÿ˜๐ŸŽ€Winnipeg Hey there, lovely ladies of Winnipeg, My name is Wells and I'm on the hunt for someone special to explore this beautiful town with. ๐Ÿ’ซSwap pics & contact info  I'm a thrill-seeker at heart, always on the lookout for my next adventure. Whether it's hitting the slopes together or enjoy...
  • Wife Swap in Winnipeg Anyone? Swingers Seek Sexy Swap in Winnipeg Hi we are Dave and Lisette here in Winnipeg. Admittedly we are pretty new to the swinger lifestyle and don't want to cross any boundaries, but we would really like to find a couple around our age to swap partners with. You don't have to be married like us, just i...
  • 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...
  • 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 ...
  • Local Librarian wants to let her hair down Woman seeking woman in Winnipeg Hey, I'm Josephine and I am a 32 year old librarian. Even though I am not a typical looking librarian I am pretty good at what I do and I love working around books as well as digital media. I am an avid reader and I would love to read you a bed time story. I must con...
  • Hello! My name is Alexis in Winnipeg Sex Hookup in Winnipeg 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 avail...
  • Nerdy Guy Seeking a Cute Dude ๐Ÿค“๐Ÿ’ฌ A bit of background I'm usually quite pretty much invisible, but I'll be a bit more noticeable once I'm awake. Tech kind of person among a few other things. Self-proclaimed self-styled pop culture geek and obsessive love of cinema and video games. Wide awake at late hours of the night having empty c...
  • 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 Winnipeg 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...
  • 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...
  • Loves hairy men Winnipeg Sally Seeks Hairy Man in Winnipeg I love hairy men and I would love to meet a genuine and hairy guy with love to give back! I like the feel of hair on my skin and it has been difficult to meet men who are hairy for some reason. No need to shave for me. I love me a manly man!! Visit my profile page...
  • Latina TS Dirty Girl Looking for a Gentleman's Dark Side ๐Ÿ”ฅ๐Ÿ‘   Sweet on the surface. Filthy underneath. View My Trassexual Dating Profile Here - As a TS darling I present like a dream while  playing like a fantasy. Stockings. Heels. A tight dress. Soft skin. And a  throbbing surprise you’ll love exploring ๐Ÿ˜˜ I need you to undress me gr...
  • Blue Collar Guy Who Loves Curves ๐Ÿ”ง๐Ÿ”ฅ I am an average guy with fairly average values. I believe in hard work and the simple things in life. Like to expect the same from others. Very frank and honest. Looking for the same in a woman - a woman who can look after herself, but is also comfortable in her own skin. I'm around if you want to c...
  • Sweet & Sinful โ€“ Submissive Babe Seeking a Domme to Take Control ๐Ÿ’ฆ Winnipeg - W4W BDSM/KINK Seeking Slave, or maybe you are a switch like me? I’m a soft femme, in my  20s, curvy, obedient when I want to be and very much wanting to try something  filthy, fun and consensually intense. WANT TO LEARN MORE ABOUT ME?  How about a drink first, perhap...
  • ๐Ÿ’ŒDISCREET AFFAIR๐Ÿ’Œ I'm in Winnipeg  and I just really need to get out and have some sex. I am married, so I need to be discreet. I'm willing to travel and even play in the backseat of the car.. I love giving bjs. Let's cheat together babe. ๐Ÿ˜‰  View Profile - Browse Pix CHEATING WIFE - AFFAIR  ...
  • 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 Winnipeg tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer tha...
  • You want to date me, right? Man seeking Woman in Winnipeg Hey, thanks for checking out my ad. I am Noel and I am here to let you know that you don't want to miss out on dating me. I am a joker and I love to laugh and make you laugh too. I am a music fan and I love going to live gigs. Who are your favorite musicians? I have ec...
  • 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...
  • 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. ๐Ÿ˜‰ Send me a private messa...