Sheboygan, Wisconsin Sex Ads and Adult Classifieds

Sheboygan, Wisconsin sex ads and adult classified listings. Select your location below to find adult dating hookups near you. Browse our listings of straight, gay and lesbian dating ads along with trans and swingers classifieds. Many advertisers desire no strings hookups. Others seek occasional or longer term dating arrangements. Search or post for free in BonePage sex classifieds!

Home / Dating

Show Ads In: Appleton / Oshkosh | Duluth / Superior | Eau Claire | Green Bay | Janesville | Kenosha-Racine | La Crosse | Madison | Milwaukee | Sheboygan | Wausau

  • June 7th, 2026
  • New to the Sheboygan area and lonesome! I am new here in this town and I would like to meet handsome gentleman to go to dinner and on date with. You are interested in me please send message to me. @RagazzaSexyX Sono nuovo qui a Sheboygan Sono nuovo qui in questa città e mi piacerebbe incontrare un bel gentiluomo per and...
  • Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Sheboygan and I got a BIG love gun to whip and pound you with until you scream! I'm def top and alpha and don't take no shit! Imma make you suck me first just for foreplay then I'll throw you back for some hard insertio...
  • British T-girl Seeking Classy Gentleman in Sheboygan... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Sheboygan and am financially independent and looking for a gentleman who is like-minded, equally solvent and has exce...
  • Blonde College Girl Looking for Fun ๐Ÿ˜‰w4m๐Ÿ“š Username: @SkylarOnBreak Dating Profile: Yes Pics Available: 11 Video Chat: Yes Messenger: Yes Message me directly if you’re real ๐Ÿ’ฌ I'm Skylar here in Sheboygan.. I'm a college girl with blonde hair and way too much school work to do. I like confident men that know how to please a gir...
  • Big Tits, Looking for Real Fun in Sheboygan Big Tits, Seeks Fun Guy in the Sheboygan Area I can entertain you and make you laugh! I have a bubbly personality, big tits that love to be touched and I like to show off. I just like to kick back and have fun. I am light hearted and fun, intelligent and also street smart. Would like to meet simil...
  • Looking for Kinky, Fun, BDSM Sex at Random Times, Must be Discrete!... S&M for Sissys in Sheboygan I am a gay male, bit of a thugish/bear into all sorts of BDSM, Fetish, Kink and some role play. I host and am seeking sissibois, twinks and queens for some extra sensual and painful fun. Your welcome, my pleasure! I have all the tools necessary in my Sheboygan dungeo...
  • Come Join US!!!! SWINGERS DOWN FOR ANYTHING AT ALL! ๐Ÿ˜˜๐Ÿ”ฅ Sheboygan ๐Ÿ’‹ Hello babess... I'm Roxxxy and my Hubby's name is Johnny. We're from J. My hubby and I are a very sexy and adventuruous swinging couple who love to explore our  deepest and nastiest fantasies.. We MUST indulge in the thrill of wife swaps and threesomes. The swingers lifestyle has brought so muc...
  • Calling all Swingers and Boobsters in Sheboygan Cali Needs Threesome in Sheboygan Hi I'm Cali a single girl 24 years old with extra large boobs here in Sheboygan looking for the right kinky couple who will love'em. You might be boobsters if you know what motorboating is. You might be boobsters if you know more that 7 words for breasts. You might...
  • Independent Woman in early 40's seeking independent guy Independent Woman 40's for Man in Sheboygan I am in my early 40's and I am looking for a cheeky, intelligent man who can make me laugh. He should be in reasonably good physical condition and have a job. Contact me @LizzieBethK if you think you fit this description and we can arrange a date. Sh...
  • My Husband and I are Into Cuckhold and Need a Bull in Sheboygan... We are professionals here in Sheboygan and are looking for a man who can rise to the occasion and fill me up while hubby watches from another adjoining room. We are easy-going and discreet and need you to be also. We should necessarily meet first to discuss some things and get to know each other fir...
  • Iโ€™m a Sexy and Naughty T-Girl Here in Sheboygan. Sheboygan T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Sheboygan area. Sweet, sexy, friendly and outgoing. I will definitely make you feel happy/sexy vibes and relaxed. I have an amazing body boys. I'm a pretty t-girl with a big present! So forget all your  worries an...
  • Asian Lilly ๐Ÿ‘ฉโ€โค๏ธโ€๐Ÿ‘จ I'm Horny Tonight Looking for a genuine sexual relationship with a like-minded asian lady? ( Do you want to view my personal profile and my sexy pictures? ) Look no further! As an Asian woman, I value deep sexy connection and meaningful fantasies.. I'm seeking a man who shares those same values and is open to explori...
  • Looking for the bride of my dreams Sheboygan 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 avi...
  • YOUNGER COUPLE ( 18+) LOOKING 4 SOME EXTRA FUN ๐Ÿ”ฅ๐Ÿฅต๐Ÿ˜‰ Hey there, I'm CONNIE from Sheboygan. My hubby and I are a swinging couple who love to explore our sickest fantasies.. Do you want to hear more about what we're down to do? I want to make love with like minded individuals and fuck hard!! The thrill of wife swaps, threesomes, and the swing lifestyle ...
  • Latina Chica New in town New in Sheboygan age 28 Latina Chica just moved here. Wants to meet sexy chick for dating and fun. I've never done this before but new location, new me!! I would love some experienced woman to teach me how things work with lesbian and bisexual women. Don't worry, I am a fast learner and I already ha...
  • I WANT TO CHEAT-ONLINE NOW ๐ŸŸข I'm tired of my husband. He just doesn't make me happy anymore. I really want to get out and see what kind of sneaky fun I can have. Do youlike the idea of us getting out together and not telling anyone? I know I do, I'm wet right now even just writing this. I want us to have som...
  • 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 Sheboygan 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 cr...
  • ๐ŸŒบEbony Godess๐Ÿ”ฅTIME TO PLAY! I am affectionate, classy, mature, independent 420 friendly, Super Cute๐Ÿ’‹ Ebony Woman seeking. I love Kissing and Making out.๐Ÿ”น♦๐Ÿ”น Nice and Sloppy. I want a secret Fuck. I can host or come to your place thats your choice!Age & Size doesn't matter ๐Ÿ’‹๐Ÿ’‹๐Ÿ’‹My Profile and Pix Here ๏ฟฝ...
  • Tattooed Student ๐Ÿ˜ˆ Who Dates Older Men Inked. Curious. Not Into Boys. ๐Ÿ–คโœ๏ธ   Yes, I’m a student. Yes, I’m tattooed.And no, I’m not into guys my age. ( MESSAGE ME NOWโœ‰๏ธ_) I like men who are settled, confident, and don’t get weird about ambition or ink. Experience is attractive. Calm is sexy. Tryin...
  • Couple of Kinky Girls Looking for fun!! ๐Ÿ˜˜๐Ÿ”ฅSheboygan Hey there, I'm Noelyn from Sheboygan and my husband and I are a sexy swinging couple looking to add some spice to our already steamy relationship. We love the thrill of meeting new people, exploring new fantasies, and indulging in all the pleasures that the swinging lifestyle has to offer. ๐Ÿ“ฉSwap ...
  • Not exactly out yet. Need discreet NSA... Mixed mexican/white male 29yrs, professional divorced with two kids. I am looking to explore my bi-sexual curiousity in the Sheboygan area with the right man and see if there is anything there. If you can be discreet and are interested then please come see me by clicking here....
  • Curvy Babe Needs a Naughty Massage in Sheboygan!... Can't afford a masseuse, and they don't exactly do what I really need anyways. I'm Brenda a 29 year old white female in Sheboygan w thick thighs and playful big tits that need a sexy man's touch. (sorry, only a man will do for this sort of thing) I work long hard hours, and at the end of my shift at...
  • I Need a Sexy Man to Tame Wild Willy! Hung Sheboygan Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Sheboygan with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks and se...
  • Hot trans chick with nice boobs Hot trans chick in Sheboygan. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Want ...
  • Free Wisconsin Transexuals Guide Wisconsin Transexuals Guide The Wisconsin Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free Wisconsin Transexuals Guide online.  Where to Meet Transexuals in W...
  • Sexy Asian Girl Sayo for American Guy in Sheboygan Hello. I am Sayo. I am a hot and sexy Asian girl. I would like to meet an American guy for relationship and dating. I am a great cook so why not get your appetite up and come for dinner? I give good massages and like romance. Send me your pictures for mine also. Message me @SayoYung to chat or for a...
  • Young, Free and Single but I want to be with Mr. Right. You have got be out there somewhere! I am lonely and I would love to find a funny and happy-go-lucky guy who can be my best friend and lover. I'm hoping you look good in a cowboy hat and jeans! Send me a text to @LonelyinSheboygan so we can get familiar!  LonelyinSheboygan...
  • Tattooed Sexy brunette, new in town & craving some fun ๐Ÿ”ฅSheboygan  ๐Ÿ“Sheboygan GIRLIE SEEKING MALE ATTENTION!!ABOUT ME: A 20-year-old brunette woman who has multiple tattoos across my sexy body... wanting to find someone in Sheboygan to spend time with a special someone while I'm in college. I'm currently studying to be a teacher.. I recently arrived here f...
  • Young Female in Sheboygan is Curious... Sheboygan Bi-curious Babe I'm Darlene, 26 living here in Sheboygan all my life and am finding myself bi-curious. I've always wondered what it must be like to be with a woman. I see women who are hot all the time and have certain sexual feelings for them, but I never acted on it. Except maybe a few ...
  • DIVORCED๐Ÿ‘ฉMOM/MILF Hey Love I am an older cute girl Horny for sex ,& I love to kiss and suck your dick. Bareback, Anal, Greek, GFe ,bbjs, kiss I love getting my pussy licked while I suck cock. I can host, but, willing to travel. ๐Ÿ˜˜ I have nasty videos for sell๐Ÿ’‹ I'm 42 Years ๐Ÿ…ณ๐Ÿ…ธ๐Ÿ†…๏ฟฝ...
  • Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Sheboygan AREA Hi baby! I am waiting to meet you. I can host or travel to you. Down to earth preop transexual woman seeking an understanding man who can appreciate my uniqueness. I am a great cook and great fun! Let your hair down and allow me to pamper you and show you wh...
  • Karaoke queen loves singing with her Knight-ess Carmel Karaoke Queen in Sheboygan You love to sing karaoke? Good!! Me too!! My name is Carmel and I adore singing. I am not shamed to say I am probably not so good but after a drink or two you probably won't care! I love singing modern pop, 60's and 70's disco, and even some modern rap. Message me ...
  • Latina Therapist to help you Latina Sex Therapist in Sheboygan Rest and relax under my gentle hands and feel the tensions leave your body. Latina woman, a caring sex therapist, seeking genuine adult conversation and romance.  Text or message me online! TherapybyMaria   Sexy Therapy by Maria Send your photo...
  • Sheboygan ๐Ÿ’“full service+bbj, european girl ๐Ÿ“ฒHMU Swap Pics & HMU and Check Out My Profile ๐Ÿ’Ž NEW GFE & PSE Open-minded BBJ 69 DFK CIM COF DATY  ๐Ÿ’Ž Nuru Massage ๐Ÿ’œ Body to body ๐Ÿ’œ Shower Together ๐Ÿ’œ aim to please ๐Ÿ’ŽFun Playful warm and cheerful with pure body. ๐Ÿ’ŽI provide a very erotic, sensual massage session. ...
  • Hello guys, looking for a boy friend So, my name is Talia from the Sheboygan area and I am completely new to this online hookup stuff. I have never put an ad in a website before so I hope I am doing this right! If you would like to speak with me or arrange a date you can check out my profile @Talia4bf here and let's swap some sexy...
  • ๐Ÿฅต๐Ÿ†SHEMALE COUPLE SEEKING SOMEONE FOR SEX๐Ÿ†๐Ÿฅต Hello men and women. We're a TRANS couple seeking someone or multiple sex partners to join us. We have cock and tits.. Does this turn you on? We're willing to let you hop in our bed, or we will come to your place. I really love sharing my partner and being fucked in front of her.. OMG I"M GETTING HA...
  • I'm the Girl Your Mum Never Warned You About!... But then, how could your mother have known? I'm Dirty Diana corrupting good decent honest men like yourself here in Sheboygan for many moons. I got a big secret and it's show and tell time baby! It's easier to show you than to tell you. I'm fully functional and passible. I need a sexy man who lives ...
  • ๐Ÿ”ฅ Confident Woman Into Pegging ๐Ÿ”ฅ W4M Dominant Dating Energy ๐Ÿ˜ˆ Are strong women a turn on? Good. I’m a pegging-friendly dominant woman seeking man who wants to experience role reversal, trust and playful submission. If you’re looking for some W4M fetish dating, female led relationship, pegging curious man, dominant w...
  • BBW -W4W ๐Ÿ” Burgers & Backseat Kisses? Count Me In BBW Lesbian ( w4w in Sheboygan ) seeking a cute, sweet and open minded woman ๐Ÿง .. I hope you love a beautiful woman who has a lot more to give๐Ÿ˜‰๐Ÿฐ .. I love any kind of woman, I just want you to accept me for me and play naughty with me ( VIEW MY PIX - MESSAGE ME )   Not all dates ...
  • Penny for your thoughts? Penny TS in Sheboygan Hey, I am Penny! I am recently new here and I am non op switch with a pretty nice pair, both top and bottom! Send me a message online @PennyTSswitch!! I'm a mixed race sweetheart, looking for a nice man who will enjoy being with me. Let's enjoy having some fun, hot dates and ...
  • 29 Year old lady seeking secret rendezvous I am presently separated but I need to keep things discreet. If you don't mind, we should keep things secret and naughty. I like fantasy play and will try fetish stuff. I haven't put an ad on here before, but, hey, if you don't try, you never know! Send me a message! @Rendezvous29Sheboygan Send me ...
  • I'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...
  • Mature Latvian lady seeking mature fun gentleman ๐Ÿˆ๐Ÿˆ Mature Latvian Lady in Sheboygan Hello there. I am Rada and I am a sexy mature woman from Latvia, now in Sheboygan. I am very independent and charming and looking for a guy I can talk with and laugh with and just hang out with on weekends. Please contact me online or text....
  • TS Temptress Ready to Ruin You (In the Best Way) ๐Ÿ˜ˆ๐Ÿ’ฆ Sheboygan  Hey lover ๐Ÿ˜˜ I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...
  • College Blonde Looking for Some Fun ๐ŸŽ“๐Ÿ˜‰ My name is Paige. I go to school and I'm a future teacher. I just wanna spice up my life and meet some new people. I'd love to meet a confident guy that could make me laugh. Want to party??  I’m pretty social, quite playful and quite adventurous – depending on my mood. Fun times ha...
  • Super sexy busty woman looking for love and appreciation Super Sexy, Busty Woman in Sheboygan Hello. My name is Lyla. I am new to this area and looking forward to exploring more. Would like to date genuine, honorable and funny man. I love sexy and being sexy and being admired by a gentleman. View my profile pics BustyLylaX...
  • Lesbians in Sheboygan Message Me ๐Ÿ˜ป๐Ÿ’ฆ๐Ÿ‘… (W4W) Ladies whowant lesbian sex NO MEN Please.. Looking for a sexy lady to play with tonight, W4W Women only please, I'm strickly lesbian. I love pussy. i'm local and ready to play.. So if you're a lady who wants to play with another sexy lady, hit me up.  ...
  • Hey Swingers - Come Give Granny Some Sugar!... Try This Hot Granny For A Threesome! Hi I'm Eva looking for a younger couple for a threesome in Sheboygan. As they say age is just a number and I'm a young at heart sexy granny still in her sexual prime. I'm Eva, 63, 5'5, 130 pounds, 36D cup, strawberry blonde hair, blue eyes and rarin' to go honey...
  • Keep Calm and Pet the Kitty... Angie here in Sheboygan with a special pubic service announcement to keep calm and pet the kitty should you have an emergency. Come closer and listen to her purr... closer now... closer now! Ahhh that's it right there, kiss the nice kitty! That's how we stay safe at night around here. Safety minded ...
  • June 6th, 2026
  • Confident Femme Dom ๐Ÿ˜ˆ Strap-On Friendly | Sheboygan I’m a DOM woman who enjoys leading, setting the tone, and exploring power dynamics with men who are curious, respectful, and open-minded. Direction cuts through noise because assertiveness holds nothing back. Leading feels natural here, especially during moments when roles shift smoothly....