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Winnipeg, Manitoba Casual Encounters

Find Winnipeg, Manitoba casual sex ads for spontaneous hookups, friends-with-benefits, or wild one-night stands. These casual encounter listings are posted by real people seeking no-strings sex in Winnipeg, Manitoba. Join now and explore your local adult scene - totally free.

Show Ads In: Winnipeg | Brandon

  • October 26th, 2025
  • Kinky Trans Woman Seeks Bondage-Loving Men For Wild Playful FunKinky Trans Woman Seeks Bondage-Loving Men For Wild Playful Fun I'm a kinky transgender woman who loves bondage play and I'm looking for men who are into the same. I want to be tied up, teased, and pleased until we both can't take it anymore. Let's explore our wildest fantasies together and make each other scream with pleasure. ? If you're into being dominant an...
  • Throbbing Cock Looking to Fuck a Tight AssThrobbing Cock Looking to Fuck a Tight Ass Are you a horny gay man looking for some hot male-on-male action? Well, look no further because I'm Kraig and I'm here to satisfy all your dirty desires. You can find me on SpunkPage.com M4M profiles under username kraigm73957. I'm a hung top who loves to pound a tight ass until it's begging for mor...
  • Anonymous Head Hunter: No Strings Attached, Just Show Up And Suck Me Dry.Anonymous Head Hunter: No Strings Attached, Just Show Up And Suck Me Dry. I need for some anonymous head. Just looking to get my rocks off without any strings attached. I need a willing mouth to take care of business, no questions asked. Let's keep it simple and straight to the point. I'm not interested in small talk or getting to know each other. Just show up, suck me dr...
  • Hot Stud Wanted For Anonymous Pounding - No Names, Just Pleasure.Hot Stud Wanted For Anonymous Pounding - No Names, Just Pleasure. I need a hot stud who's down to pound me anonymously. I want you to come over, slide your hard cock deep inside me, and give it to me good. No need for names or small talk - just pure, unadulterated pleasure. ?? Let's make this a night to remember as we lose ourselves in the heat of the moment. Whet...
  • Penny Non-Op TS Bottom or Top | Winnipeg, ManitobaPenny Non-Op TS Bottom or Top | Winnipeg, Manitoba Hey, I am Penny, a non-op TS who can switch top or bottom for your pleasure, and I aim to please! I am recently new here and I am pretty nicely endowed! Send me a message online @PennyTSswitch!! I'm a mixed race trans sweetheart, looking for a nice gentleman who will enjoy being with me. I'm tired ...
  • "Trans Woman With A Surprise Looking For Guys To Play ??""Trans Woman With A Surprise Looking For Guys To Play ??" I need for some guys who can handle a real woman with a little extra something down below. I'm a transgender woman packing heat and ready to destroy some ass. If you're into getting pounded by a girl like me, hit me up. I love feeling my dick deep inside a tight hole, making you moan and beg for mor...
  • Seeking Dominate Man For Bondage Play - LetSeeking Dominate Man For Bondage Play - Let's Explore Fantasies! I'm in the mood for some bondage play and I need a man who can handle me. I want to be tied up, teased, and pleased until I can't take it anymore. ? If you think you have what it takes to dominate me in the bedroom, then I want to hear from you. Let's explore our wildest fantasies together and push ...
  • Eager Sex Slave Seeks Dominant Woman To Fulfill Deepest DesiresEager Sex Slave Seeks Dominant Woman To Fulfill Deepest Desires I'm eager to be your obedient sex slave, ready to fulfill all your wildest desires. I crave to be dominated by a strong, confident woman who knows what she wants in the bedroom. Let me worship every inch of your body and submit to your every command. I long to be tied up, teased, and pleased until I...
  • Wild Lesbian Orgy: Explore, Moan, And Fulfill Fantasies With MeWild Lesbian Orgy: Explore, Moan, And Fulfill Fantasies With Me I need a wild time with multiple ladies at once. I want to feel your bodies pressed against mine, exploring every inch of each other until we're all moaning in ecstasy. Let's get lost in the moment together, letting our desires run free as we fulfill each other's fantasies. Whether you're experience...
  • Seeking Anonymous Stranger For Wild, No-strings-attached Pleasure Tonight ?Seeking Anonymous Stranger For Wild, No-strings-attached Pleasure Tonight ? I need a stranger to anonymously fuck. No names, no strings attached - just pure, unadulterated pleasure. I want to feel your hands exploring every inch of my body, driving me wild with desire. Let's lose ourselves in the moment, letting our primal instincts take over. I crave the excitement of a fo...
  • Hung Guy Wanted To Plow Me Hard And Deep Tonight ?.Hung Guy Wanted To Plow Me Hard And Deep Tonight ?. I'm looking to get plowed hard and deep by a hung guy who knows how to work it ?. I want you to pound me like there's no tomorrow, making me beg for more ?. Let's fuck, exploring each other's bodies until we both explode ?. I'm open to trying new things and pushing boundaries, so don't be shy about ...
  • Italian Stallion For Male Companionship in AuburnItalian Stallion For Male Companionship in Auburn Hey Guys! I'm a tall, long hung Italian stallion with great tongue that loves to explore. You want pleasing? I can please! Message @Mario4malefun and have the night of your life. I'm young, virile and well hung. I've got what you want! I'm looking for casual M4M dates or Sugar Daddy arrangement...
  • Hard Cocked Trans Woman Seeking Man For Wild Ass Pounding Fun.Hard Cocked Trans Woman Seeking Man For Wild Ass Pounding Fun. Hey, I'm a trans woman with a hard cock looking to pound a man's tight ass. I'm not into small talk, just want to get straight to the action. Let's have some fun together and explore our wildest fantasies. I'm open-minded and down for anything you're into. Whether you're experienced or curious, I'll...
  • Wild Gangbang: Pound Me Until I CanWild Gangbang: Pound Me Until I Can't Take It Anymore. So, here's the deal - I need a group of guys who are down to fuck me all at once. I want to feel every inch of you pounding into me until I can't take it anymore. It's going to be wild, intense, and oh so satisfying. ?? I'm not looking for anything serious, just a good time with some hot and horny ...
  • Trans Woman Seeks PNP Fun With Adventurous Guys For Wild Exploration.Trans Woman Seeks PNP Fun With Adventurous Guys For Wild Exploration. I'm a trans woman with a craving to PNP and looking for guys who are down to get wild. I want to feel your hands all over me as we explore each other's bodies. Let's forget about the world outside and just focus on having a good time together. I'm open-minded and ready to try new things, so don't be...
  • Pound My Ass Like TherePound My Ass Like There's No Tomorrow, Let's Make Fireworks! I need a guy who's down to pound my ass like there's no tomorrow. ? I want you to take me from behind and show me what you're made of. Let's make some fireworks explode in the bedroom together. ? I'm not shy about what I want, and I hope you aren't either. If you think you can handle giving me the a...
  • LetLet's Get Wild: Seeking A Woman To Fuck My Pussy I'm looking to have my pussy fucked with a woman who knows how to please. I want someone who can take control and make me scream with pleasure. I'm not interested in anything vanilla - I want someone who is willing to explore their wild side with me. Let's push each other's boundaries and see where ...
  • Ebony Beauty Seeks Winnipeg Princess Ebony Beauty Seeks Winnipeg Princess Hello gorgeous ladies! My name is Cheryl and this is my first time ever posting a dating ad. You can't imagine how nervous I am but here I am, putting myself out there! Go easy on me. It's terrifying! lol.... but here goes. I am medium height and build. I have great perky tits so if that's your thi...
  • Lusty Hottie for Lesbian, Bisexual or Bicurious Woman in WinnipegLusty Hottie for Lesbian, Bisexual or Bicurious Woman in Winnipeg My name is Allison and I am medium height and weight, and fit with more than ample breasts that love female attention! So, like I am 22 and I am new here since December. I like dancing and movies. I'm sexually adventurous and kink friendly, also party friendly but no hard drugs plz. You want to talk...
  • Sexy Trans Woman With Throbbing Surprise Seeks NSA Fun With Men.Sexy Trans Woman With Throbbing Surprise Seeks NSA Fun With Men. I'm a sexy trans woman with a throbbing surprise between my legs, looking to NSA fuck with horny guys who can handle it all. I'm not here for games or drama, just pure adult fun. ?? If you're into exploring new things and living out your wildest fantasies, then I'm your girl. Let's get straight to t...
  • Male college stud for upscale gentleman in Winnipeg areaMale college stud for upscale gentleman in Winnipeg area Hey, I am a broke college student right now and I have to pay for everything.  I may not be rich but I am a stud. I only do top, so if you are into that kind of thing let me know. Let's chat first, swap pics and get to know each other. Private message me! Username: @XXSTUDTonyPhotos: 41Vi...
  • LetLet's Get Wild And Naughty Together - No Strings Attached Fun I need a sexy lady who's down to get wild and naughty with me. I want to feel your body pressed against mine, exploring every inch of each other in the heat of the moment. Let's lose ourselves in pure ecstasy as we fuck each other senseless, fulfilling our deepest desires without any strings attache...
  • Winnipeg Contractor Seeks Female Partner in Crime! Winnipeg Contractor Seeks Female Partner in Crime! Hello, this is Erik. I own a contracting business in the area. I enjoy distressed property rehab and I'm always looking for rehab projects. I do some new construction and commercial projects as well. I am looking for an intelligent woman who can make me smile. When not working, I love the outdoors i...
  • LetLet's Get Wild And Loose - NSA Pounding Session Fun I'm looking to NSA fuck. Just a casual, no-strings-attached pounding session with a guy who's down for some fun. I'm all about getting wild and letting loose, so if you're into that too, we'll definitely vibe. Whether you're experienced or new to this, I'm open to exploring together. Let's make each...
  • Exciting black guy in WinnipegExciting black guy in Winnipeg Herman, black male, active and fit, age 32. I am excited to get to meet you! I'm looking for lovely lady of any age but not too young to understand my humor nor not too old to keep up ;) Hahaha! I am fit and fast and muscular. If you're into sports or working out, I'm your guy! Let's get coffee or d...
  • Seeking Wild, No-strings-attached Lesbian Pleasure With A Sexy Stranger ?Seeking Wild, No-strings-attached Lesbian Pleasure With A Sexy Stranger ? I'm looking to have some anonymous fun with another woman. No need for names or small talk, just pure pleasure ? Let's explore each other's bodies and fulfill our wildest fantasies together. I want to feel your touch and taste your desire as we lose ourselves in the moment. Whether it's a one-time t...
  • Kinky Submissive Man Seeks Dominant Woman For Wild, Erotic Adventures.Kinky Submissive Man Seeks Dominant Woman For Wild, Erotic Adventures. I need a dominant woman who knows how to take control in the bedroom. I want to be your willing and obedient sex slave, ready to fulfill all of your desires. I crave being tied up, teased, and pleased until I can't take it anymore. ?️ I want you to use me however you please, exploring every inch o...
  • Private Gloryhole Available For No-Strings-Attached Sucking Satisfaction ??Private Gloryhole Available For No-Strings-Attached Sucking Satisfaction ?? I'm here to offer up my private gloryhole for some no-strings-attached fun. ?? If you're in need of a good suck, look no further. I'll make sure to take care of your needs and leave you satisfied. Just slide through my discreet setup, stick it in, and let me work my magic. No questions asked, just p...
  • Let Me Devour You, Make You Squirm, And Moan In Ecstasy.Let Me Devour You, Make You Squirm, And Moan In Ecstasy. I need a tasty treat to devour ? I want to bury my face between your thighs and make you squirm with pleasure. Let me show you just how good I am with my tongue ? I crave the taste of your sweet juices as you moan in ecstasy. No need for small talk, let's get straight to the main event. Trust me, yo...
  • LetLet's Get Wet And Wild: Piss Play Partners Wanted Now! I'm looking to piss play with men who are into getting wet and wild. I want to explore our kinks and have some naughty fun together. Let's let it all flow and enjoy the sensation of warm piss cascading over us. I'm open-minded and ready to experiment, so don't be shy about your desires. Whether you ...
  • Hung and Big Busted Tranny Babe with Added Surprise! πŸ‘πŸ‘πŸ†Hung and Big Busted Tranny Babe with Added Surprise! πŸ‘πŸ‘πŸ† Tammy non-op tranny, age 39, big yummy tits!! πŸ‘πŸ‘ Well hung πŸ† just waiting to be discovered in my panties (also yum!). Everything works, clean and so cute!! What more could you want in a gurl?!! Let's swap pics and numbers. Message me @Tammy39T and we can talk and meet! Send your recent...
  • Worship Me Between Your Thighs As I Devour You Whole.Worship Me Between Your Thighs As I Devour You Whole. I need a woman who wants to be worshipped between her thighs. I have an insatiable craving to eat pussy until you're begging for more. There's nothing that gets me going like feeling your body quiver with pleasure as my tongue works its magic. Let's explore every inch of each other's bodies and lose...
  • LetLet's Make Your Anal Fantasies A Reality Tonight ??? I need a guy who's down to pound my backdoor ??. I've been craving some anal action lately and I need a man who can handle it. I want someone who knows how to take control and give it to me hard. No holding back, just pure pleasure and ecstasy. If you think you're up for the challenge, hit me up. Le...
  • Big Titties, Love To Be Tit Fucked!Big Titties, Love To Be Tit Fucked! Looking for a wild time? Well, look no further because you've found me, Jammie! I love to get down and dirty in the bedroom, exploring all kinds of naughty fantasies. Whether you're into blowjobs, anal play, or just some good old-fashioned fucking, I'm your girl. When it comes to sex positions, I'm...
  • LetLet's Explore Your Backdoor Together - Satisfaction Guaranteed! ?? I need a woman who's down to let me explore her backdoor ?? I've got a craving that only anal sex can satisfy, and I need someone who's ready to take it like a champ. If you're into getting pounded hard and deep, then I'm your guy. Let's make some magic happen together and see just how wild we can g...
  • LetLet's Get Wet And Wild: Seeking Piss Play Partner ???? I need a guy who's into piss play ?. There's something about letting loose and getting wet that really gets me going ?. I want to explore this kinky side of me with someone who's just as eager to dive in. No holding back, no shame, just pure uninhibited fun ?. Let's push boundaries and see where our...
  • Looking to have my asshole destroyed. Come get some of this POWER BOTTOMLooking to have my asshole destroyed. Come get some of this POWER BOTTOM I'm a horny gay man looking for some hot male-on-male action. My name is Waring and I'm seeking gay, bisexual, or bi-curious guys who are down for some wild fun. I love sucking cock, getting my tight ass pounded, and playing with dildos. I also enjoy giving sloppy blowjobs, riding a huge throbbing ...
  • Lesbian Bondage Anyone? ILesbian Bondage Anyone? I'm New in Winnipeg. I believe in experiencing life to its fullest. Does that sound like you? My name is Michelle, age 27. I am ready to meet a hot local girl to explore the world of bondage and BDSM in a safe, erotic setting. Send me a private message if you would like to swap pictures, chat and meet up. Attractive, fu...
  • Mind-blowing Blowjobs For Guys Who Can Handle It, Satisfaction Guaranteed!Mind-blowing Blowjobs For Guys Who Can Handle It, Satisfaction Guaranteed! I need to give some mind-blowing blowjobs to guys who can handle it. My lips are ready to work their magic and make you feel like you're in heaven. I'll take my time, savor every moment, and leave you begging for more. ?? So if you're looking for a good time without any strings attached, hit me up. ...
  • Lonely young man just out in WinnipegLonely young man just out in Winnipeg Lonely young man just out in Winnipeg. I served a 2 year stint in prison for a nonviolent offense. During my stay, I learned what I've been missing. I am a gay man! Actually, I'm probably bisexual but I am monogamous and definitely prefer a man's company. I just came out about 6 months ago and I am ...
  • Powerful African-Queen Dominatrix in Winnipeg, ManitobaPowerful African-Queen Dominatrix in Winnipeg, Manitoba Professional Domme Desiree is interviewing subs. My Winnipeg dungeon is well equipped, as this is My life, not a hobby. I am a strong, powerful shemale who will take charge and maintain total control. Your obedience will be required at all times and you will learn to serve Me. I am the top and well ...
  • Wild Woman Wanted For Intense Pounding. LetWild Woman Wanted For Intense Pounding. Let's Explore Our Bodies Together. I need a wild woman who's craving a good pounding. I want to fuck pussy until we both can't take it anymore. Let's explore each other's bodies and indulge in some naughty fun together. I'm not looking for anything serious, just some no-strings-attached pleasure. If you're up for a steamy encounter f...
  • Sexy Man Wanted To Eat My Pussy And Drive Me Wild.Sexy Man Wanted To Eat My Pussy And Drive Me Wild. I'm looking to have my pussy eaten by a man who knows how to please a woman. I want someone who can make me moan with pleasure and leave me begging for more. I love feeling a talented tongue explore every inch of me, driving me wild with desire. ? If you think you have what it takes to satisfy my cr...
  • Sexy hung and big busted Winnipeg shemale πŸ†πŸ’¦Sexy hung and big busted Winnipeg shemale πŸ†πŸ’¦ Hung and Busty Shemale in Winnipeg Hey, I'm Tammy, age 33, 38DD, well endowed lady stick, and so cute!! What more could you want in a gurl?πŸ†πŸ’¦Send your pics for mine and check my profile @Tammy38DD so we can talk and meet! Send your recent pic for mine. Long term arrangements are possible with...
  • Kinky Trans Woman Seeks Skilled Guy For Hot Blowjob FunKinky Trans Woman Seeks Skilled Guy For Hot Blowjob Fun I'm a transgender woman looking to get a blowjob from a guy who knows how to handle what I've got. I'm not here to waste time, just looking for some good old-fashioned fun. ? If you're into giving head and can make me feel good, hit me up. Let's keep it casual and discreet, no strings attached. Just...
  • Daniel 28, Plumber, new to the Winnipeg areaDaniel 28, Plumber, new to the Winnipeg area 28 y/o Man New to the Winnipeg Area I  am Lee, age 28, fit and active. I am a plumber by trade. I work days but I love the nightlife. I'm looking for new people to meet in the Winnipeg area and I would love to meet a nice lady I can talk to and listen to and maybe more if we feel the vibe. If ...
  • Anonymous Head Wanted: Hot Mouth Needed For Discreet Satisfaction.Anonymous Head Wanted: Hot Mouth Needed For Discreet Satisfaction. I need for some anonymous head. I need a hot mouth to swallow me whole and leave me satisfied. No strings attached, just pure pleasure. Let's meet up in a discreet spot and make this happen. I want you to worship my cock like it's the only thing that matters. ?? Don't hold back, show me what you can...
  • Noel, age 29, seeking Woman in WinnipegNoel, age 29, seeking Woman in Winnipeg Hey, I am Noel. Thanks for checking out my ad. You don't want to miss out on dating me!!! I am a natural comedian and I love to laugh and make you laugh too. I am a music fan and I love going to live gigs. I play a little guitar too. Who are your favorite performers? I have eclectic musical tastes. ...
  • Seeking Adventurous Woman For Deep Backdoor Fun. LetSeeking Adventurous Woman For Deep Backdoor Fun. Let's Explore Together! I need a woman who's up for some backdoor fun. ? I can't get enough of that tight feeling when I slide in deep. Let's explore new heights of pleasure together. No need to be shy, I'll make sure you're comfortable every step of the way. Just imagine how good it will feel when I pound you from behind....
  • HOT Male for Male in WinnipegHOT Male for Male in Winnipeg Hey guys, I'm Jeff. I will visit you or you can visit me. Age 29. Tall and fit. I'm working my way through college but I manage some free time. I need to spend time with local guys. I love the male form and appreciate all types of men and love to explore all body types. No judgment, kink friendly wi...

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