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  • April 28th, 2024
  • Widower seeking affection in ChicagoWidower seeking affection in Chicago Chicago Widower Seeking Affection Hello ladies, my name is Jonathan and I am seeking some female company for fun times and affectionate days. It has been a while and I have to face that I'm lonely. I am 52 and still look in my late thirties (I am told) and I am fit and healthy. I love riding horses...
  • PeeWeePeeWee's Looking for a BIG Adventure! Hi, I'm Herman, and me and my little friend are looking for some excitement in Chicago tonight. If you are up for an adventure we are too! We aren't too picky, just hope you like Tequila and dancing. Please be motherly and kind. Can you come out and play?. If so click here to come out and see u...
  • I Need a Chicago MILF WhoI Need a Chicago MILF Who's Got That Sexpertise! Chicago Man Needs Experienced Woman Hi all you hot mommas out there in Chicago. I'd love to meet someone to hookup with on a regular basis. FWB style. Young women my age seem to be sort of squirrely and awkward in bed. (just my experience) I picture a MILF as being more focused and educated on matt...
  • Click here - Add to Cart.Click here - Add to Cart. Chicago Single Dad for Fun That's my mom in the pic with me BTW. I'm Jonah here in Chicago a single working dad age 31 with a three legged cat and hope to find a woman for some NSA fun who has a big purse to get lots of snacks into the movie theatres. I'm not afraid to talk about Bruno, or yell Yab...
  • New to this place, Andrew, 36.New to this place, Andrew, 36. Man Seeks Woman in Chicago Ok, what do guys say on these things? I want a kind, friendly and fun lady to hang out with and maybe get to know each other a bit. I am tall and somewhat slim build with dark brown wavy hair and blue eyes. Send me a message @TallManChicago...
  • Mixed Race Male Seeks Sexy Female for FWB in Chicago...Mixed Race Male Seeks Sexy Female for FWB in Chicago... Hi there ladies I'm James new to Chicago and I want to meet you. I've been divorced for about a year now. Not really wanting to dive in too deep just yet, but you never know what will happen in the future. I need a sexy more mature woman who can relate to me in terms of life experiences and life les...
  • Biker Looking for His Wild Child...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...
  • Sugar Magnet Looking for His Sugarbaby in Chicago...Sugar Magnet Looking for His Sugarbaby in Chicago... Hi, I'm Matthew a semi-retired Real estate developer recently divorced seeking my sugarbaby for sexy good times and companionship. I have a yacht, penthouse and nice cars, but still something BIG is missing... YOU! I admit, I'm not the best looking guy, but you could do worse. Do you like to travel?...
  • I will never ghost you!I will never ghost you! I’m Tommy age 37 and am sort of a home body. But, I still like going out for dinners, drinks, movies and having fun now and then. I live in Chicago and my hobbies are: writing music and poetry, spontaneous trips, and playing my piano. I work in tech, so in this crazy world, let’s be craz...
  • II'm Sexy and I'm Noah!... Single Black Man 4 No Strings in Chicago Black male, 33, 5'11, 180 pounds, with a good education and positive attitude from Jamaica originally. I have lived here in Chicago for about 10 years and love it. There is always something to do. I am looking for an original woman. What I mean is some...
  • Chill Dude Needs His BBW Queen...Chill Dude Needs His BBW Queen... Hi ladies I'm Mike from here in Chicago, age 30, 6'0, 190 pounds, Italian, French, Norwegian mix, tatted, well endowed, muscular, journeyman plumber, who loves lots of curves and passion in his woman. I don't meet many women in my line of work and bar pickups are not usually the right way to find a ...
  • You want to date me, right?You want to date me, right? Man seeking Woman in Chicago This is Noel and I am here to let you know that you don't want to miss out on dating me. i am a joker but not a smoker but I love to laugh and make you laugh too. I am a music fan and I love going to live gigs. Shoot a message to me @Noel4Fun if you are on the same...
  • Super hot guy waiting for girl of my dreamsSuper hot guy waiting for girl of my dreams Black Man for Romantic Woman in Chicago Dark chocolate man with romantic nature. My name is Dwayne and am 6 feet 3 and well built. I am into sports and I love watching football. Life is good and all but I want to meet a beautiful woman for passion and adventure. Check out my profile @DwayneSeekingR...
  • What songs make you dance?What songs make you dance? Are you the Stayin Alive type? the Twerker type? Currently looking for a Chicago 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 is...
  • I’m willing to lie about how we meet...I’m willing to lie about how we meet... I am a 32yr old half Hawaiian, Samoan, and half German. Born and raised right here in Chicago. I'm 5'11" 190 pounds and have brown hair and hazel eyes. I’m a Disney obsessed, official Netflix movie rater. I’m also a cereal connoisseur and to top it all off I'm an 80’s pop music Lov...
  • Ranch owner and lonely olRanch owner and lonely ol' guy Male Ranch Owner Seeking Woman in Chicago Ok, I ain't that old. Just turned 47 in July. I am a ranch owner with 40 acres and am looking for a gal who is adventurous, outdoorsy, fit and healthy enough to hike, bike and picnic on the trails. Enjoy travel and new experiences? Me too! Hit me up with a ...
  • Searching for My Sexy Care Free Biker Babe!...Searching for My Sexy Care Free Biker Babe!... Hi ladies I'm Tommy from right here in Chicago born and raised. I'm 32 years old, 6'1, 200 pounds, dark hair, blue eyes, Fire Department/EMT, take good care of myself, but do love to party once in a while. I'm a pretty good cook I'm told by the guys, so if you're not no biggie.  I get quite a ...
  • Fun Loving Couple in Chicago Seeks Female for Threesomes...Fun Loving Couple in Chicago Seeks Female for Threesomes... Hi, we are Jordan and Riley, a sort of a younger swinger couple in Chicago looking to explore threesomes with the right girl who is open to sex with a man and a woman at the same time. We look forward to experimenting with some wild fantasies we have and welcome any thoughts you might have to spice ...
  • Blue Eyed BDE...Blue Eyed BDE... Some say I should be in porn, but I have a profession that doesn't mesh with that, (EMT) plus I wouldn't want my future kids to ever see it. Hi ladies I'm Chad, 31 years old, not too serious, blonde hair, blue eyes, 6'0, 190 pounds, size 11" real uncut thick burrito type, I'm very oral both giving a...
  • Shy 41 yr old guy Shy 41 yr old guy Shy But Romantic in Chicago Hey ladies, I am Bryan, 41 and I am a little shy when it comes to meeting women. I am romantic and thoughtful and looking for a kind hearted woman. If you would like to swap photos and contact info just message me @ShyRomanticBryan and I will respond as soon as...
  • Cunning Linguist...Cunning Linguist... Oral Expert Seeks Woman in Chicago Hi, I'm Calvin a single male in Chicago looking for a single woman who is funloving and passionate. I am orally gifted and speak fluent English and have an accent. My greatest oral talent however is in my long tongue - my whiskers are soft and tickly, but not...
  • I wanna be your friend and loverI wanna be your friend and lover Mature black man in Chicago Howdy, the name is Samuel and I am a mature gentleman looking for a lady who is smart, funny and outgoing. I am 52, divorced, no kids and I am into riding my bike and fishing on weekends. There is just one thing missing - maybe it's you! How about you message me and...
  • Chicago Gamer Seeks Female Gamer for Dating and Fun...Chicago Gamer Seeks Female Gamer for Dating and Fun... Hey let's join forces and level up together. I'm a bit of a nerd and have an outgoing personality. (very social) I'm Denny, 23 years old, 6'0, 200 pounds, blonde hair, blue eyes, love gaming and my cat Sam. About my girl: She should be from Chicago, love gaming or at least be okay with it, be smart,...
  • Englishman Without His Butler...Englishman Without His Butler... It's a hard life for an Englishman not to have his butler in America, but I have learned to adjust. The really hard adjustment is not having a good woman and best friend. Moved here to Chicago about 3 years ago from London to work in the tech industry and do rather well despite the sky-high prices a...
  • Girls on The Goth Side Get My Blood Pumping...Girls on The Goth Side Get My Blood Pumping... Hi I'm Derek, 24 years old, 5'11, 180 pounds, black hair, hazel eyes, as it stands, I'm a bit anti-social. I have broad sexual tastes ranging from the vanilla to BDSM and enjoy fantasy play and trying new things. I need a dark Chicago girl who knows what the Goth scene is all about. Bloodsuckas...
  • Cuckhold Bull in Chicago Available for Couples...Cuckhold Bull in Chicago Available for Couples... Hello, I'm Ryan and live in Chicago offering my unique service as a Cuckhold bull. I have the physical credentials and am attractive. I stand 6'0, good shape, 9"+ inches, thick and uncut, single, black hair, blue eyes and I am a very easy going guy.  Respect and attentiveness are my watchwords...
  • Nascar fan looking for lady to have fun withNascar fan looking for lady to have fun with Nascar Fan for Lady in Chicago If you like watching Nascar or motor racing, hit me up for a date. I am a down to earth guy who likes to chill on weekends and do fun stuff. You must have a good sense of humor because I do like to laugh! There is nothing more sexy than a woman who can make me laugh. ...
  • Nigel 56, Chicago new hereNigel 56, Chicago new here Male 56 seeks woman in Chicago Howdy gals, I am Nigel and I am back on the market after a dailed buy out with an ex. lol. That's life. I am lighthearted and friendly and I love to laugh and be made to laugh. If you want to know more, just out my bio page @FunNigel56. ...
  • Handsome, tall and tanned guy wants to meet shy womanHandsome, tall and tanned guy wants to meet shy woman Shy Guy for Shy Gal in Chicago 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. Want a mature woman for fun, laughter and more. Message @TallEric34m in Chicago....
  • Need My Big Phat Booty Princess...Need My Big Phat Booty Princess... I love big butts and I cannot lie! I'm a red blooded black man, 29 years, 6'0, stays in shape, lives in Chicago and who loves him some bubble butts. More cushion for the pushin baby! If you are a woman living in Chicagoland with an exceptional sexy ass then don't hesitate to get hold of me and show ...
  • Looking for the bride of my dreamsLooking for the bride of my dreams Chicago Contractor Seeks Wife This is Erik and I am a local resident and own a contracting business. I am looking for a bright intelligent woman who can make me smile. When not working, I love the outdoors and I am an avid hiker and biker. Send me a message @ErikBachman. ...
  • Shiny blue eyes and 34 years old.Shiny blue eyes and 34 years old. Man for Woman Dating in Chicago Hi, I am Brandon and I am 34. I am excited to meet a loyal and loving woman who can complete my world. If you would like to say hi, come and see my proflie and message me for pics and contact info @BRANDON34M....
  • I will always laugh at screaming goats...I will always laugh at screaming goats... Chicago Man Seeks FWB I’m George age 40 here in Chicago and am a bit of a shut-in. I still like going out for drinks and having fun but I find more peace and have more fun just kicking back at home. I love the beach, movies, Disneyland, writing music and poetry, spontaneous trips, and playing...
  • Playful Cub Searching for Cougar in Chicago...Playful Cub Searching for Cougar in Chicago... I love mature women and appreciate the skills they've developed over the years. I'm Dana 22 years old, have my own car and apartment and good job, so I'm not looking for a sugar momma situation. I just want a sexy cougar to play with and get to know even if it's for a short time. I would be so grate...
  • II'm a Chubby Chaser in Search of My BBW Queen... I'm Charles a black man about 6'0, 200 pounds, in good shape, 26 years old, in college and am an admirer of large women. I'm open to any race and any size be it BBW or SSBBW. I love a phat booty and big boobs. If you live in Chicago and have large assets then I'm your man! Hoping for more than a ho...
  • Breast Obsessed Little Boob Boy...Breast Obsessed Little Boob Boy... Need Mezmerizing Mammaries in Chicago Controlled by Cleavage, nipples, areolas, breasts, boobies, tits, hypno, highly suggestible, kinks, fetishes all types. I'm Lenny a 5'9, about 160 pounds, 22 year old single male in Chicago here for magic milk bag fantasies. If you have boobies I'm interested! ...
  • II'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...
  • 47, 647, 6' 2 Man Seeking Woman for Dates in Chicago Hey, Richard here. I just want to say hi to you and hope you might check out my profile and see if you want to date me. I am just a regular guy looking for a regular gal. I've been single too long. It's time to meet someone special to enjoy the fun things in l...
  • exciting black guy waiting for youexciting black guy waiting for you Exciting black guy in Chicago I am Herman. I am an active and fit, age 32, black male and I am excited to meet you! Looking for lovely lady of any age but not too old to keep up ;) I am fit and fast to run with and muscular. Tall at 6 feet 3. Want to work out? Travel? Coffee and lets see where it g...
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  • Hey, any SteamPunkers out there in Chicago?...Hey, any SteamPunkers out there in Chicago?... Hi, I'm Brad T. from Chicago born and raised. I love everything SteamPunk and am searching for a local woman who appreciates the romanticism of the late Victorian era. I'm 30 years old, love sci-fi, SteamPunk, conventions and events, travel and work. I have a dynamite job working with younger autist...
  • April 27th, 2024
  • Looking for a 420 Friendly Girl Tonight...Looking for a 420 Friendly Girl Tonight... Come on over and smoke my blunt baby! This will be an NSA boobies for doobies exchange. If things go right we could be steady smoke buds. I got the weed if you got the need. I'm Mario a Latino man, 25 years old, great shape, love the bud and women. This works out for the both of us. If you're jonesi...
  • Daniel 28, Plumber, recently new to areaDaniel 28, Plumber, recently new to area UK Man New to the Chicago Area For Dating I am from the UK and I am plumber by trade. I am looking for new people to meet in the Chicago area and I would love to meet a nice lady I can talk to and listen to and maybe more. If you would like to say hello send me a message @PipeManLee....
  • Want a Strong 💪💲 Successful Man? Want a Strong 💪💲 Successful Man? Strong💪Sexy😏Wealthy🤑  Man Looking For Fun!! (M4F)😉 Hi I am a Single 35 years old straight man looking for a hot woman to be my eye candy and trophy woman. Let me pamper you and take you out. - My Profile- My Pictures  I love lots of foreplay, kissing , giving and recei...
  • I want to worship your sexy sweet feet...I want to worship your sexy sweet feet... I'm a passionate Italian man looking for sexy feet to pamper in Chicago. Just the sight of a pair of angel feet leaves me breathless. I can't even go near a beach for the over-stimulation it brings. I do like it in the spring when women start wearing strapped sandals though because it usually leaves...
  • II'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 Chicago, because I did a long distance relationship once and...
  • Joker and a Smoker...Joker and a Smoker... I'm a 30 year old, 6'1, 200 pound hardcore biker living in Chicago and I go by the handle of Joker. Looking for my sexy road queen who preferably smokes too, or at least doesn't mind that I do. All this anti-smoking shit brings out the rebel in me, and if you're like me then we'll get along gre...
  • ChicagoChicago's Sex Ninja Has Come to Your Rescue... Single Guy 4 FWB in Chicago Hi I'm Carl, and maybe the part about being a ninja isn't quite true, but I do have a yellow belt in Karate or was it Judo? Anyhow, I'm living in Chicago and am looking for something more long term with the right lady. Me, I'm a black male, 31 years old, 5'10, 180 p...
  • George, 31, long beard to tickle you withGeorge, 31, long beard to tickle you with Bearded Man for Non-Bearded Lady in Chicago Hey ladies, I am George and I am 31. I have been growing my beard for 3 years and it is nice and long. If you like bearded dude let me know and send me a private message @BeardedGeorge. I'm fun loving, athletic, Alpha type guy but gentle and passionate in...
  • Hey ladies, I am Roger, 49 and looking for real loveHey ladies, I am Roger, 49 and looking for real love Man Seeking Woman for Dating in Chicago Hi, my name is Roger. I'm here seeking a woman for dating and friendship - hopefully a lot more! I am 49 with no kids and I own my home. I am local to this area and have lived here for 22 years. I want to meet a kind a funny lady for fun times. Come and say h...