Winnipeg, Manitoba Sex Ads and Adult Classifieds

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Show Ads In: Winnipeg | Brandon

  • October 28th, 2026
  • I Need a Body Rub Followed by a Naughty Rub! Hey gents I'm Lauren, 24, hard worker, large boobs, brown hair, blue eyes and 5'5, and I want a full body massage if you live in the Winnipeg area. About me: Sucker for a good long massage, a major turn on! About you: sensual stong hands, stamina, know the female anatomy and be a quick learner of to...
  • 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...
  • Handsome, tall and tanned guy wants to meet shy woman Shy Guy for Shy Gal in Winnipeg Male, 34 looking for gal, 26+ age. I'm a bit on the shy side so if you are also, that's a plus. I warm up once I start to feel comfortable. I have many interests and like new experiences. I want to meet a mature woman for fun, laughter and more. Check out my profile ...
  • Hot Brunette Mature Woman Hot Brunette Woman in Winnipeg Hi, I'm Angel. I'm seeking hot man who knows his way around the female body. I enjoy dinner, dancing and fun and frolics in the bed. Send me a secure message! BrunetteAngel41XX...
  • Thick Latina Looking for a Confident Man 🔥🌹 Hi guys, it's Camila. I am 22 years old, curvy and latina. I think that confidence is probably the most sexy quality a man can have. I'm really into confident men with a great sense of humor who know how to have fun and live life without over thinking things. My Pix - Message Me  I'm a very af...
  • Hot Angel brand new to Winnipeg and web dating. Outdoorsy girl. I can be your hottest fishing buddy! Ok, I guess I am doing this right and I am hoping someone sees this! I am 28 and want to meet a cool guy who likes outdoorsy activities like hiking and (unbelievably) fishing! Yes, I can even hook a worm! Want to meet and hang out with me?  ...
  • Lithuanian Lady Likes Lady Love Seeking a beautiful woman to be with. You must be kind and funny and like any kind of music. Tatts and piercings are a turn-on! I love to sit and watch movies and I love music, exploring the Winnipeg area and eating out. Messsage or text @Natalia4LadyLove xoxo, Natalia Username: @Natalia4Lady...
  • Shy girl looking for first date Shy girl for lesbian hookup in Winnipeg It is so hard to meet people at the moment and I am really wanting a date. No strings unless we hit if off. I am careful with socializing, so don't worry about me not being safe. I'm a lipstick lesbian femme, looking for fun chick to hang out with and see whe...
  • Ebony W4W - 🌙 Movie Night or Makeout Session? You Decide 😘 📍 Winnipeg Ebony Lesbian Seeks her Queen, or Princess 👸😉 A soft playful cutie like me is looking for a girl to play with tonight. Netflix and  chill? More like kiss and thrill👄 .  I can meet up with you to watch a late night  movie, buy some extra snacks and maybe sneak so...
  • ⭕❌⭕24 hour❌⭕❌new girl❌❌best massage❌⭕❌ Winnipeg 😘🔥 💯💯New🔄 sexy ,if no young , No pay🔄 New Feeling🔄💯💯 🏮🏮🏮Waiting For You, 🌊Let you enjoy different treatments🌊 and 🌊feelings🏮🏮🏮 🌸🌸🌸Four hand massage 💆🏻💆🏻💆🏻 👙👙👙You will never disappointed 👌👌👌 📣📣📣 table s...
  • Secret Lovers ...💍❤️😘 Shhh Don't tell my husband My Husband doesn't like to get wild like I do. I want to have super sexy fun!! 🤩🤩 Discreet Messages - Private Message 💌 I want to do all the things I'm missing out on with you.. I need to have fun and I need to feel a real man again. Want us to make porn together, meet women ...
  • 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...
  • No Strings in Winnipeg - Hot and Sultry, Looking for Affection Thanks for opening my ad. I've been neglected for far too long and am in need of affection. Things are complicated so no strings only please. That is likely to change at some point in the future. My hair goes down to my lower back and I have soft skin. My height is 5'8" and I am slender but curvy i...
  • Older woman seeking mature gentleman for long term relationship Older Woman Seeks Mature Man Seeking gentle fun, soft cuddles and long walks in the park. I am a romantic at heart and love a good laugh. Prefer relationship. Go ahead, don't be shy, message me or call @OlderSexySuzie. We can enjoy life together! ...
  • BIG n CUTE BBW for Male in Winnipeg 🍑🔥 Brianna BBW for Winnipeg Male Cute, flirty and playful BBW seeking a nice man in the Winnipeg area. 🍑 I'm curvy in all the right places. I like to dress nice and I'm classy in public. But I love getting down and dirty in the bedroom! I'm a hot, naughty girl who wants it all. I love exploring sex...
  • Fun Redhead With Freckles Seeking Trouble 🔥😉 My name is Emily, and I am a very mischievous, freckled redhead with an unmistakable grin. And the fact that I’m rather good with a certain breed of handsome man only makes things worse. Visit My profile and See My Pix I love to have fun. Funny guys and unexpected moments turn me on. Whether ...
  • Fabulous Filipina woman wants wonderful man Filipina Woman Seeking Passionate Man Hey guys, my name is Amina and I am full Filipina, just moved here to Winnipeg. I want to meet a kind and passionate man so please only message me if you are serious and fun and want pleasure! I am open minded. Hit me up @Amina4Passion to chat online and a...
  • Cute TS Sugar Baby Seeking Male💎Aria Username: @AriaSweet Trans Friendly: Yes Private Meetups: Yes Phone Chat: Yes Pics Available: 18 Message me if you like feminine Transsexual 💬 Hello, I am AriaTS here in Winnipeg. A very sweet and very feminine trans-girl that loves to be your sugary little sugar-baby, accompanied by a man ...
  • Road Head Sally Drivin' Hard in Winnipeg Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Winnipeg. 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 par...
  • 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...
  • I want to be a whore I am a transexual very hot. Good with my mouth and my ass. Comment on my photos. I would appreciate it if you downloaded my photos and share me with other men in the Winnipeg area. Click here and come see me anytime!...
  • What songs make you dance? Are you the Stayin Alive type? the Twerker type? Currently looking for a Winnipeg girl and I love a girl with rythm and groove who knows how to get down. I am not the shy type and some would say extroverted. I love a good time as much as anyone, but also enjoy chillin and bein with my boo. If this i...
  • College Blonde Looking for Some Fun 🎓😉 My name is Paige. I go to school and I'm a future teacher. I just wanna spice up my life and meet some new people. I'd love to meet a confident guy that could make me laugh. Want to party??  I’m pretty social, quite playful and quite adventurous – depending on my mood. Fun times ha...
  • I wanna be your friend and lover Mature black man in Winnipeg Howdy, my name is Samuel and I am a mature gentleman looking for a lady who is smart, funny and outgoing. I am 52, widower after 28 years, no kids. I am into riding my bike, the gym, and fishing on weekends. There is just one thing missing - maybe it's you! Do you like ...
  • Smokin' Hot Lesbian in Winnipeg... I'm Kat, 27yrs old, 140 pounds, black hair, brown eyes, dirty minded, tatted, love to smoke and I don't care what they say about smoking here in Winnipeg or anywhere. If you are a single lesbian or bisexual OK with smoking or are a smoker yourself then maybe we should chat. I love sex and smoking, a...
  • Irish eyes are smiling in Winnipeg 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 Winnipeg 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 gentlem...
  • Looking for Mr. Goodbar... Just out, and just out of the Marines, now a college student and 22 years old gay male living in Winnipeg Looking for experienced well endowed older man to give it to me. I'm 5'11, 180 pounds, blue eyes, brown hair, 7in cut, and in great shape. This is a little awkward, I'm new so be patient with me...
  • Amazing kisser looking for lips to practice on Lipstick Lesbian Loves Kissing Do you love kissing? I do! I love it!! It is such a turn on! My favorite parts to kiss are my neck and my face and my lips and my whole body! I am Kimberley, 22 and a part time waitress. I'm eager to meet you!! Send me a private message to @LipstickLesbianKim User...
  • 🍁 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...
  • BBW's - Heavy Hotties With Huge Sexual Appetites!... BBW's for Men in Winnipeg There are thousands of local chubby cherubs looking for men just like you in the Winnipeg area. They want fun, romance and want to meet you. Come check out their naughty pics and profiles. Click Here for More!       Other Sites of Interest: BBW's...
  • Don't Worry I Bite! Feisty redhead trans in Winnipeg 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 ...
  • 💪🍆 I'm All Tha Chocolate You Could Need 💪🍆 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 🍆 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...
  • Caught My Boyfriend Cheating... Now it's MY TURN! Looking for some hot NSA revenge sex with the right guy in Winnipeg. Must be STD free and have your own place or arrange for a room. I will not give you my real name or address here. I'm a 24 year old, 5'7, slender, blonde haired, blue eyed female seeking a sexy man. We'll have to chat first and mee...
  • Beach Lover Looking for a Chill Guy 🌊☀️ Hi, I’m Kayla. If you love the water like I do, you will probably get to know me pretty well. I am a very easy going person who loves to live a sun filled drama free life.. I am quite a down to earth, fun loving person. I love to chat and I enjoy a conversation that may go in many different di...
  • 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, ...
  • 🔥 Confident Woman Into Pegging 🔥 W4M Dominant Dating Energy 😈 Are strong women a turn on? Good. I’m a pegging-friendly dominant woman seeking man who wants to experience role reversal, trust and playful submission. If you’re looking for some W4M fetish dating, female led relationship, pegging curious man, dominant w...
  • October 27th, 2026
  • Help! Single and Got That Tingle! Itchy in Winnipeg Hey there boys I'm Natalie here in Winnipeg 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...
  • I'm Top Bitch! Get a Taste of Femdom! I'm Mistress TopBitch here in Winnipeg, and I'm going to pound and drain your worthless asses of all self-respect, and you're going to fucking love every damn second of it! Strap-ons and pegging lesbians are my speciality. (among other things) If you are all filled with fear ...
  • Hot trans chick with nice boobs Hot trans chick in Winnipeg. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Want t...
  • 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...
  • Young, Free and Single but I want to be with Mr. Right. You have got be out there somewhere! I am lonely and I would love to find a funny and happy-go-lucky guy who can be my best friend and lover. I'm hoping you look good in a cowboy hat and jeans! Send me a text to @LonelyinWinnipeg so we can get familiar!  LonelyinWinnipeg...
  • 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 ...
  • 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 👄 AikoFemme Username: @Aik...
  • British T-girl Seeking Classy Gentleman in Winnipeg... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Winnipeg and am financially independent and looking for a gentleman who is like-minded, equally solvent and has excep...
  • Looking for someone fun & exciting! Angela26Winnipeg 💋 Looking for a very exciting man in the Winnipeg area who can make me laugh and who enjoys long walks and romantic dinners. I know it sounds cliche but I do love long walks in the park!  💋 Send me a message and if you want to go for a walk with me, let me know. (Angela26Winnipeg)...
  • I'm the Girl Your Mother Warned You About!... Ok, but I'm not All bad! What? Just because I want some fun and sexy playtime riding the weenie? Well then just spank me already and give it to me hard and teach me a lesson I'll never forget! Punish me and pound me like you mean it. Is it hot in here, or is it just me? Your mother was right and I n...
  • Single Female Wants to Explore Fetishes... I'm Dani, a sexually adventurous woman who is looking for a fetish playmate in Winnipeg who is able and willing to go with me on this kinky journey. In past non-kinky relationships I have always played a more dominant role (for some reason) however I have changed my mind and I am keen to switch to m...
  • 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...
  • 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...
  • Island Girl With a Playful Smile 🌺😉 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 Winnipeg from the island and I want to get out and have ...