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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

  • November 15th, 2025
  • 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...
  • Seeking Men For Anonymous Head - Pure Pleasure, No Strings Attached.Seeking Men For Anonymous Head - Pure Pleasure, No Strings Attached. I need to give some anonymous head to men who need it. ? No strings attached, just pure pleasure for both of us. I'll make sure you leave satisfied and wanting more. Let's meet up in a discreet spot and get down to business. I love the thrill of not knowing who you are, just feeling your excitement ...
  • Destroy My Ass And Dominate This Trans Woman Tonight, Boys!Destroy My Ass And Dominate This Trans Woman Tonight, Boys! I'm looking to get my ass destroyed by some horny guys who know how to handle a trans woman like me. I want you to pound me hard and make me scream with pleasure. I'm craving that feeling of being completely filled up and dominated by a group of men who aren't afraid to show me a good time. Let's ma...
  • 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...
  • Shy Crossdresser Seeks Friend for Discreet Dressing, Possible Dates | Winnipeg, Manitoba AreaShy Crossdresser Seeks Friend for Discreet Dressing, Possible Dates | Winnipeg, Manitoba Area Hello. I'm a married crossdresser in the Winnipeg area. My fem name is Gloria. I'm 28 years old, clean and disease free. I am passable in appearance and voice but the problem is that my wife doesn't approve. She knows but doesn't want anything to do with my crossdressing. I REALLY need to let my fem...
  • 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...
  • 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...
  • LetLet's Indulge In Mind-Blowing Oral Action Together, Satisfaction Guaranteed ?? I need a sexy lady who's down to let me feast on her sweet pussy. ? I wanna make you moan and squirm as I devour your dripping wetness. Let's explore each other's bodies and reach new heights of pleasure together. I promise to take my time and give you all the attention you deserve. No rush, just pu...
  • 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...
  • Let Me Be Your Obedient Sex Slave, Fulfilling All Fantasies.Let Me Be Your Obedient Sex Slave, Fulfilling All Fantasies. I need a dominant woman who knows how to take control in the bedroom. I want to be your obedient sex slave, fulfilling all of your wildest fantasies and desires. I crave being tied up, blindfolded, and teased until I beg for release. You can use me however you please, making me your personal playthi...
  • 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...
  • SHEMALE BEAUTY Ready to Eat Your Manhood Now! 🍆💦SHEMALE BEAUTY Ready to Eat Your Manhood Now! 🍆💦 Hey there! I am Blanca, a shemale beauty queen who can take top or bottom. I am ready to eat your manhood now.  🍆💦 We can do bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my partner. Give me a try and you may never go back. Message me @BlancaShema...
  • 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...
  • Lonely Winnipeg Female, Send Sext Messages & PicsLonely Winnipeg Female, Send Sext Messages & Pics I need a sexting buddy, maybe more! I am Cheryl, a friendly and outgoing 25 year old woman, new to Winnipeg. I'm not shy in the traditional sense but I find it hard to meet people these days. I enjoy all things fun and I love great, passionate sex. I take care of myself, I'm curvy, fit and clean, a...
  • Simon Hot Male for Male or Couples in Winnipeg. Call for a night of joy!Simon Hot Male for Male or Couples in Winnipeg. Call for a night of joy! Contact me for your dream night. Male for male or couples. I am Simon and I can do whatever you want to do. Top or bottom. Kinks and fetishes are fun to explore. Shy or just curious? That's my specialty! Let me introduce you to male on male sex the way it should always be. View my online profile and...
  • 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...
  • Hung Top Looking to Fuck an AssHung Top Looking to Fuck an Ass Are you a horny gay man looking for some hot male-on-male action? Look no further, because I'm Johann and I'm ready to rock your world. You can find me in the SpunkPage.com M4M profiles under username johann24880. I'm a dominant top who loves to pound a tight ass until it's begging for more. I enjo...
  • 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...
  • Anonymous Oral Pleasure: LetAnonymous Oral Pleasure: Let's Meet For Mind-Blowing Satisfaction ?? I need a stranger who's down for some anonymous head. ?? No strings attached, just pure pleasure. I'll make you feel like you're in heaven with my talented mouth and eager attitude. Let's meet up in a discreet location and get straight to business. Your identity will remain a mystery as I focus on g...
  • 9 Inch TOP Only Trying To Blow My Load.9 Inch TOP Only Trying To Blow My Load. Are you a horny gay man looking for some hot male-on-male action? Look no further! I'm Lawrence, and I'm a hung top who loves to dominate and pound a tight ass. I can be rough or gentle, depending on your preference. I enjoy deepthroating, rimming, and using toys like dildos to enhance the experienc...
  • Seeking Sexy Stranger For Anonymous Head In Discreet Location. Pure Pleasure Guaranteed!Seeking Sexy Stranger For Anonymous Head In Discreet Location. Pure Pleasure Guaranteed! Hey, I need a sexy stranger who's down for some anonymous head. No strings attached, just pure pleasure ?? Let's meet up in a discreet location and get straight to business. I'm craving the thrill of giving mind-blowing oral without knowing each other's names. If you're into keeping things mysteriou...
  • 38 yr old Lonely Woman Seeks Female Passion in Winnipeg38 yr old Lonely Woman Seeks Female Passion in Winnipeg Successful Business Woman Seeking Female in Winnipeg Hello, I am Julia, age 30. I own my business and have a flexible schedule so I've decided it is time to begin dating again after a long time being single and focused on work. I have my own money so I won't need anything but your time and affectio...
  • 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. ...
  • Fuck Me Hard and Make Me CumFuck Me Hard and Make Me Cum I'm a horny gay man looking for some hot male-on-male action. My name is Gerold, and I'm seeking other gay, bisexual, or bi-curious guys who want to have a good time with me. You can find me in the SpunkPage.com M4M profiles under username geroldnew98743. I love getting my cock sucked and giving sl...
  • Sexy Young Woman for First Lesbian Experience in Winnipeg 🥰Sexy Young Woman for First Lesbian Experience in Winnipeg 🥰 Hi I'm Melodie! I am 19 and looking for my first lesbian experience. 🍑 My family has been cool and supportive. My mom suggested I put an ad out online so here I am. Wait a minute... how does my mom know this site?!! 😬 hahah, anyway, here goes.   I am into clubbing but also like quie...
  • Seeking Sexy Lady For Anonymous Encounter - Pure Pleasure Awaits!Seeking Sexy Lady For Anonymous Encounter - Pure Pleasure Awaits! I need a sexy lady who's down to fuck anonymously. ? No names, no small talk, just pure pleasure. Let's meet up, get naked, and explore each other's bodies in the dark. I want to feel your hands all over me as we both moan with delight. ? Whether you're experienced or new to this, I'll make sure you...
  • I Tried to Be Good But These Huge Tits Deserve a Big Cock! I Tried to Be Good But These Huge Tits Deserve a Big Cock! Big Tits, Seeks Hung Guy in Winnipeg I am Destiny. Not my real name but I'll let you know in time. I can entertain you and make you laugh but I don't take myself too seriously! I have a bubbly personality, big tits that love to be touched and I love to have a good time. I just like to kick back an...
  • Anonymous Fuck Buddies: Deep, Raw Pleasure In Discreet Location.Anonymous Fuck Buddies: Deep, Raw Pleasure In Discreet Location. I'm craving to get fucked anonymously. ? I want to feel you deep inside me, pounding away until we both explode. ? No need for names or small talk, just pure raw pleasure. Let's meet up in a discreet location and satisfy our primal urges. ? Your hands on my body, your breath on my neck, driving me w...
  • Private Gloryhole Fun - Let Me Satisfy Your Deepest Desires ??Private Gloryhole Fun - Let Me Satisfy Your Deepest Desires ?? I'm looking to give head in my private gloryhole for men who need some discreet fun. I love to feel you throbbing in my mouth, ready to explode ?? No need for small talk, just come over and let me take care of you. I'll make sure you leave satisfied and drained. I'm here to fulfill your deepest desi...
  • Seeking Dominant Woman To Fulfill BDSM Fantasies - Your Sex SlaveSeeking Dominant Woman To Fulfill BDSM Fantasies - Your Sex Slave I need a dominant woman who can handle me as her sex slave. I want to be at your beck and call, ready to fulfill all your wildest desires. I crave the feeling of being controlled by you, letting you take charge and show me who's boss. ?️ Whether it's being tied up, blindfolded, or spanked, I'm ea...
  • 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 ...
  • 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....
  • Seeking Hot Stranger For Anonymous, No-Strings-Attached Pleasure ??Seeking Hot Stranger For Anonymous, No-Strings-Attached Pleasure ?? I need a hot stranger who's down to pound me senseless. I want to feel your hard cock deep inside me, no questions asked. ? Let's make this encounter all about pure lust and pleasure. I'm craving that anonymous thrill of getting fucked by someone I don't even know. ? If you're up for some discreet f...
  • Horny Trans Woman Ready To Fulfill Your Wildest Desires ??Horny Trans Woman Ready To Fulfill Your Wildest Desires ?? I'm a horny trans woman with a hard cock looking to NSA fuck. I want to feel your hands all over me, exploring every inch of my body. Let's get lost in the moment and fulfill each other's desires. I'm open-minded and ready for some wild fun. No strings attached, just pure pleasure. ?? If you're up f...
  • 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...
  • 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 ...
  • 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...
  • LetLet's Get Kinky: Looking For A Man To Plow Me I'm looking to get plowed by a man who knows how to handle me in the bedroom. I want someone who can go all night long and leave me begging for more. I need a guy who isn't afraid to take control and show me who's boss. Let's explore our wildest fantasies together and make each other scream with ple...
  • Naughty Girl Looking for Some Fun!Naughty Girl Looking for Some Fun! Are you ready to get down and dirty with a wild girl who knows how to have a good time? Well, look no further because I'm right here waiting for you! My name is Arlana, and I love to explore all kinds of naughty pleasures in the bedroom. When it comes to sex, I'm not shy about what I like. I enjoy ...
  • Seeking Sexy Lady For Anonymous, No Strings Attached Pleasure Sessions.Seeking Sexy Lady For Anonymous, No Strings Attached Pleasure Sessions. I need a sexy lady who's down to anonymously fuck. No strings attached, just pure pleasure and satisfaction. I want to explore every inch of your body, tease you until you can't take it anymore, and then pound you into oblivion. Let's indulge in our wildest fantasies together and make each other scr...
  • 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...
  • Winnipeg King Looking for my Queen of Hearts 💖Winnipeg King Looking for my Queen of Hearts 💖 Hey there, sexy ladies of Winnipeg! My name is Christian and I am searching for that special lady who is ready for fun and maybe you'll be swept off your feet!  Swap pics & contact info @ChrisF34106. Don't be shy to reach out and say hello! 💬I'm a hopeless romantic at heart, always ready...
  • Regular Winnipeg Guy, Age 47 with a Lot to Offer!!Regular Winnipeg Guy, Age 47 with a Lot to Offer!! Richard here, hoping to meet someone nice to spend time with. 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 a regular guy looking for a regular gal for extraordinary fun! I keep busy and have a great life but I've been single too ...
  • Throbbing Surprise: Trans Woman Seeks Horny Men For Wild, Anonymous Fun.Throbbing Surprise: Trans Woman Seeks Horny Men For Wild, Anonymous Fun. I'm a sexy transgender woman with a throbbing surprise down below, looking to anonymously fuck with some horny men. I'm not interested in small talk, just want to get straight to the point and have a wild time together. Let's explore each other's bodies and fulfill our deepest desires without any st...
  • LetLet's Get Wild: Seeking A Man To Satisfy My Desires I'm looking to get fucked by a man who knows how to handle me in the bedroom. I want someone who can make me scream with pleasure and leave me begging for more. I need a guy who isn't afraid to take control and show me a good time. If you think you have what it takes to satisfy my needs, then hit me...
  • Kinky Sex Slave Seeks Dominant Woman For Wild, Intense Pleasure.Kinky Sex Slave Seeks Dominant Woman For Wild, Intense Pleasure. I need to be your willing sex slave. I crave to be dominated by a strong and confident woman who knows exactly what she wants in the bedroom. I want to explore all of our deepest desires and fantasies together, pushing boundaries and experiencing intense pleasure like never before. ?️ I long to f...
  • 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 ...
  • 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 ...
  • II'm Your Eager Sex Slave, Ready To Fulfill Your Fantasies. I'm aching to be your sex slave, to fulfill all your wildest desires and fantasies. I crave the feeling of being completely dominated and controlled by a powerful woman like yourself. I want to worship every inch of your body, obeying your every command without question. Let me be your willing serva...
  • Anonymously Explore Pure Pleasure With Me - No Strings Attached Fun!Anonymously Explore Pure Pleasure With Me - No Strings Attached Fun! I'm looking to fuck anonymously with a woman who's down for some no-strings-attached fun. I want to feel your body pressed against mine, exploring every inch of you as we lose ourselves in pure pleasure. Let's make it all about satisfying our desires and indulging in the raw, primal passion that com...

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