Winnipeg Men Seeking Men Classifieds

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Show Ads In: Winnipeg | Brandon

  • September 25th, 2026
  • 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...
  • Gay Body Rubs - Need Sexual Relief? - Yeah, You Need SAL!... Sal here in Winnipeg to melt your stress away and relieve that pent up sexual tension like no other. I host and offer full amenities and services to my gay clients. All men are welcome as well as couples who need to unwind and spice up the day the right way. I serve gay, bixsexual and bi-c...
  • ๐Ÿป Fresh Out of a Relationship.. Just Want a Fun Night Username: @RyanOutTonight Private Meetups: YesPhone Chat: YesVideo Chat: YesPics Available: 16 ๐Ÿ’ฌI'm ready for a night out๐Ÿ˜‰HMU Hi.. My name is Ryan and I'm from Winnipeg. Recently come out of a relationship and I'm not looking for anything too serious. I need to get out and about, get some e...
  • Henry your Puerto Rican Stud for Local Man Puerto Rican male for male in Winnipeg I am Henry, from Puerto Rico and I am living local and wish to meet you. I am friendly, sexy with a big dick that is sure to please. I'm easy going and like to have fun. I'm very much sexually adventurous so I can please you much. Check my profile @RicoHe...
  • Discreet meet only in the Winnipeg area!!! I am Jamali here in Winnipeg for a while doing some work for a tech company so I can't get too involved with anyone. I'd like to get out and experience this town, the party vibe and the men in it. I'll be going home in a few months. If you are iinterested in an Asian-Indian man then come check me ou...
  • ๐Ÿ”ฅGay Hookups โ€“ Bedroom Eyes & No Bullsh*t Vibes ๐Ÿ’‹๐Ÿ†  Your mama warned you about me yet your dad would secretly appreciate my nature ๐Ÿ˜ˆ 34,  toned, tattooed, and nasty in the best way possible. I seek a genuine male partner who  understands my body type through strong hand usage and dominant presence and filthy sexual thoughts. Your ...
  • SUGAR DADDY ๐Ÿญ๐Ÿ‘จโ€๐Ÿฆฐ ๐Ÿ’ฆLooking 4 Play Boy M4M Hey there babe, I'm a 25 year old male who is searching for another guy to play with and spoil. I'm strong and muscular, I drive a beautiful car, I can take you to do things you've always desired ๐Ÿค‘ It turns me on so damn much to find a cute little man to play with and take care of. Let me be D*dd...
  • 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...
  • ๐Ÿ’ฏREAL๐Ÿ’ฏHANDSOME๐Ÿ’ฏMANLY You ready for some manly gay sex here in Winnipeg? I know I am, I made this ad to make a nice BF to fuck or fuck me.. We can even find some other sexy guys to have some sex with too.. I love partyingโœจ and having group sex. Do you like to take it or give it? I will give you something to suck on alr...
  • Athletic Guy Looking for a Fun Gym Buddy ๐Ÿ’ช๐Ÿ”ฅ A bit about me: I'm quite healthy and fitness oriented, I love working out. I'm 180cm tall and generally a pretty chilled person. I'd love to meet other men who like living healthy, confident and maybe even looking for similar things as me. Fitness enthusiasts, gym rats, and healthy eaters. I enjoy ...
  • 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...
  • September 24th, 2026
  • SciFi lovin' guy getting lonely in Winnipeg I love SciFi TV and movies. I am Will. I am 31, tall and muscular with light brown hair, grey eyes and tan skin. I work and I have a nice home and car. I never seem to have time to get out and mingle. I need a friend with benefits! Send me a private message to @WillSciFiFan if you want to swap ...
  • 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 ...
  • MALE STUD FOR HOT ACTION - Winnipeg Area ๐Ÿ˜ˆ๐Ÿ”ฅ๐Ÿ‘ฌ Get Ready for the Fuck of Your Life! ๐Ÿ† Hi there! I'm Mason and I'm ready to get down and dirty with you. I am only into top. I love it all - pounding your ass, playing with sex toys, kink play, and watching you gagging on my throbbing dick until my cum explodes in your mouth. ๐Ÿ†๐Ÿ’ฆ I'm a kin...
  • ๐Ÿ’Ž Adorable Sugar Baby ๐Ÿ’Ž Seeking his Generous King ๐Ÿ‘‘ ๐Ÿ“  Location: Winnipeg    Seeking: A kind/dominant daddy๐Ÿ‘‘  A Little about Me: Hello everyone! I am a sweet, fit blonde with a flirty nature  and an appreciation for the good things in life. I enjoy being pampered, looked after and treated  like a king. If you ...
  • Hung Black Male Winnipeg for male action Wants hot male for male sex in Winnipeg. All races welcome. Want some hot male-on-male action? Well, look no further because DeAndre is here to satisfy all your dirty desires. Private message me @DeAndreXXX24. I love hot dates with hot guys, any race. Pretty much top because I prefer being in charg...
  • Professional Wants to Settle down in Winnipeg... Gay Man for Commited Relationship Hi, I'm Hal a nurse practitioner ultimately looking for gay marriage in Winnipeg. I'm not too particular about race, religion or political bent really. As long as you are a loving and caring person. If you have a hot temper do not contact. I'm over that crap! Willi...
  • I am a hot lil sissy living in Winnipeg - HMU!... Black Sissy Boi in Winnipeg Checking this out online, never been at this before. I'm Charles a black male, 155, five foot 5, w long and skinny as you can see in my hot profile pics. Just looking for a little sexy adventure here in the Winnipeg vicinity. Click here for more of me......
  • September 23rd, 2026
  • 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...
  • ๐Ÿ’ฆMale for Male โ€“ NSFW Only: You Dom, I Submit. Period. ๐Ÿ˜ˆ๐Ÿ–ค  The advertisement is not intended for casual greetings. This is: You top. I bottom. You  take. I give. You tell me what to do. I do it. Simple. Dirty.  Hot. View My Gay Dating Profile Here - โค๏ธโœจ I completely submit to all things kinky while being body-positive and ready to sur...