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  • June 18th, 2025
  • Chicago - Letโ€™s Make Some Mischiefโ€ฆ And Maybe a Mess ๐Ÿ˜‰Chicago - Letโ€™s Make Some Mischiefโ€ฆ And Maybe a Mess ๐Ÿ˜‰  Hey gorgeous ๐Ÿ˜ I’m a 35-year-old guy from Chicago with a cheeky smile, strong  hands, and an even stronger craving for adventure — both in and out of bed. My intention is  to meet a woman who possesses confidence because I seek someone to flirt with and share laughter ...
  • 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...
  • Nice Guy? Yep. Push-Over? Only When Youโ€™re Behind Me ๐Ÿ˜‰๐Ÿ’ฆNice Guy? Yep. Push-Over? Only When Youโ€™re Behind Me ๐Ÿ˜‰๐Ÿ’ฆ 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. ๐Ÿ’– 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...
  • 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...
  • ๐ŸŒŸ Handsome JOHN Seeking a Spark ๐ŸŒŸ LET๐ŸŒŸ Handsome JOHN Seeking a Spark ๐ŸŒŸ LET'S PLAY SOME Hello there, lovely ladies of Chicago! My name is Johann and I am on the lookout for that special someone who can ignite a fire in my heart. ๐Ÿ’–Swap pics & contact info I have a passion for exploring the great outdoors, whether it's hiking through the mountains or relaxing by the lake. ๐Ÿ...
  • 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,...
  • 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, comfortable in my skin, ass...
  • How do I look? / M4W in ChicagoHow do I look? / M4W in Chicago Man for Woman in Chicago Check out my profile and tell me how I look. I am Sam. I'm a model, age 32 and told I am darn hot looking. Hit me up and check out my profile @SamChicago. Send your pics for mine. I'm available evenings and weekends.  Sorry guys, no men or couples. I appreci...
  • 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...
  • 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...
  • 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...
  • Tom, 42, wants single minded womanTom, 42, wants single minded woman Hello ladies, I am Tom, age 42 in Chicago. I have a good job, a new truck and I own my house. Life is pretty good and I'm ready to take the next step toward finding love. Could you be who I'm looking for? We'll never know unless you message me.  I am not looking for someone who is going to giv...
  • 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 ...
  • June 17th, 2025
  • Chivalry Isnโ€™t Deadโ€”But I Might Be After One Good Ride ๐Ÿ˜๐Ÿ‘Chivalry Isnโ€™t Deadโ€”But I Might Be After One Good Ride ๐Ÿ˜๐Ÿ‘ an looking for a hot woman to be my eye candy and trophy woman. Let me pamper you and take you out. I love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very into oral and eating that kitty. I'm a damn good lover and know how to use my cock! I want us both to use each o...
  • 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...
  • 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...
  • 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...
  • 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...
  • Tall & Peggable ๐Ÿ˜ˆ๐Ÿ’‹ Looking for My Boss BabeTall & Peggable ๐Ÿ˜ˆ๐Ÿ’‹ Looking for My Boss Babe Hi I am a Single 32 years old straight white male.I'm in Chicago and I would love to meet and amazing woman who wants to feel a real man! ๐Ÿ˜‰ I love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very oral i love to give as much as receive. I love to make her cum all ov...
  • You want to date me, right?You want to date me, right? Man seeking Woman in Chicago Hey, thanks for checking out my ad. I am Noel and I am here to let you know that you don't want to miss out on dating me. I am a joker and I love to laugh and make you laugh too. I am a music fan and I love going to live gigs. Who are your favorite musicians? I have ecl...
  • 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...
  • 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 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...
  • Age 47 Regular Guy with a Lot to Offer!!Age 47 Regular Guy with a Lot to Offer!! 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 go out for a date. I am just a regular guy looking for a regular gal. I've been single too long. I keep busy and have a great life but It's time to m...
  • Sailing nut wants to meet lady sailorSailing nut wants to meet lady sailor Male for Female Date Wanted in Chicago Do you like going out on boats and sailing into the sunset? If you do, give me a call and we can check out the water together. My name is Lewis and I love the water. I do have lots of other interests including coffee shops, microbrews, dining out, music, worki...
  • Flirty Fun, Endless Kisses & No Judgments ๐Ÿ’‹ ChicagoFlirty Fun, Endless Kisses & No Judgments ๐Ÿ’‹ Chicago  The person I am today is a relaxed yet passionate man who balances his gentlemanly nature with  flirtatious tendencies by sending sweet messages during mornings and provocative messages at night. ๐Ÿ˜ˆ I enjoy tasty  food with slow kisses and unexpected plans that typically lead to in...
  • 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...
  • 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, a professional with no kids and no personal entanglements. I am local to this area and have lived here for 22 years. I would love to meet a kind a funny ...
  • FtM seeking Princess Bride in ChicagoFtM seeking Princess Bride in Chicago FtM seeking Woman in Chicago Hi, I'm Andy, age 33, FtM mixed-race transgender man living in Chicago. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message...
  • 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...
  • Sweet Guy with a Naughty Side ๐Ÿ˜‡โžก๏ธ๐Ÿ˜ˆ Searching for My Queen ChicagoSweet Guy with a Naughty Side ๐Ÿ˜‡โžก๏ธ๐Ÿ˜ˆ Searching for My Queen Chicago Hey there, lovely ladies of Chicago! My name is Romeo and I'm on the hunt for my very own Juliet. Are you ready to be swept off your feet by a modern-day romantic? Look no further because I'm right here waiting for you. Swap pics & contact info ChicagoI may not have a balcony to profess my ...
  • Exotic and Erotic Orlando From Tuscany Italy...Exotic and Erotic Orlando From Tuscany Italy... For More Than Just a Hookup Ladies I am Orlando visiting in Chicago. Let me take you on an erotic journey of passion and delight tonight. I know how to treat a woman and bring out the sensual romantic in you. Just let yourself go and forget all about your cares for the evening. You will be in good ...
  • ๐ŸŒŸ Looking for my Queen of Hearts ๐ŸŒŸ Chicago๐ŸŒŸ Looking for my Queen of Hearts ๐ŸŒŸ Chicago Hey there, lovely ladies of Chicago! My name is Maury and I am on the hunt for that special someone who can make my heart skip a beat. ๐Ÿ’“ You can find me in the dating profiles at Swap pics & contact info , so don't be shy to reach out and say hello! I'm a hopeless romantic at heart...
  • 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...
  • 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. They tell me I'm handsome. I'll let you be the judge of that. what I do know is that I like to have fun and I'd love to mee...
  • June 16th, 2025
  • Iโ€™m willing to lie about how we meet...Iโ€™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...
  • 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...
  • 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...
  • 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...
  • 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...
  • 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...
  • Ken, 42, lonely for youKen, 42, lonely for you Male for Female Chicago Hi there! My name is Ken and I am 42 and looking for a real nice woman in the Chicago area. Send me a message and check my profile @Ken42seeksWoman for my recent pictures and contact info. Let me know about you. I enjoy skiing, hiking, boating, travel, gaming and reading. Ac...
  • 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...
  • Letโ€™s Flip the Scriptโ€”You Lead, Iโ€™ll Moan ๐Ÿ˜๐ŸŽ€ChicagoLetโ€™s Flip the Scriptโ€”You Lead, Iโ€™ll Moan ๐Ÿ˜๐ŸŽ€Chicago Hey there, lovely ladies of Chicago, My name is Wells and I'm on the hunt for someone special to explore this beautiful town with. ๐Ÿ’ซSwap pics & contact info  I'm a thrill-seeker at heart, always on the lookout for my next adventure. Whether it's hitting the slopes together or enjoyi...
  • Daniel 28, Plumber, recently new to areaDaniel 28, Plumber, recently new to area 28 y/o Man New to the Chicago Area For Dating I am fairly a 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. What do you enjoy doing? I like trying new things so don't be shy. I like camping, d...
  • Sweet Guy, Dirty Mind, Zero Pressure ๐Ÿ˜‡Chicago๐Ÿ˜ˆSweet Guy, Dirty Mind, Zero Pressure ๐Ÿ˜‡Chicago๐Ÿ˜ˆ  Hi beautiful. At twenty-nine years old I maintain my fitness while being humorous and charming yet slightly  mischievous. When I look at you my eyes show weakness while my laughter makes your stomach ache  ๐Ÿ˜ View My Dating Profile and Pictures - My approach to romance includes p...
  • 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 love distressed property rehab and I'm always looking for rehab projects. 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 ...
  • 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...
  • 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 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...