Sheboygan, Wisconsin Alternative Sex Ads - BDSM, Trans & Swingers

Browse Sheboygan, Wisconsin alternative sex ads to meet kinky locals looking for BDSM, domination & fetish, transgender sex, or swingers & threesomes hookups near you. It's free to search these alternative classifieds, or post your own ad!

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July 8th, 2025

Explore the Thrilling World of Gregory's Fetish Hey there, Sheboygan folks! It's me, Gregory, and I've got something exciting to share with you all. Brace yourselves for a unique adventure into the world of my fetish. Now, before we dive in, let me tell you a little about myself. I'm a friendly guy from this charming Wisconsin town who loves t...

Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Sheboygan Hey! Thanks for looking at my ad. This is the first time I've done this so bear with me plz. I am Jared, FtM trans man. I transitioned at age 25 and I just turned 30. Come and meet me!  Check my personal profile @FtMJared29 and say hi!&...

MISTRESS KIM IS HERE TO DOMINATE YOU.... Seeking new worthy, generous submissive Mistress Kim Sheboygan Dominatrix Message Me Online: MistressKim4subSheboygan Flogging...prostate...nipple play...force by... paddling...dress up play..humiliate... strap on...must obedience......

Spicy Hot 🌶 Tranny Girl from Colombia Latina Tranny Girl in Sheboygan Hey guys, I am Gabriella and I am looking for a longterm relationship with a gentleman who love sex as much as I do! I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery except breasts. I am smooth and clean, very femini...

Unleash Your Wildest Desires with Brittany from Sheboygan! Hey there, curious souls of Sheboygan! I'm Brittany, and together with my amazing husband, we're here to take your fantasies to new heights. Brace yourself for an unforgettable journey into the world of pleasure and exploration. We're a friendly and open-minded couple who thrive on pushing bounda...

Mistress Leila, Mature Mistress for sub in Sheboygan Mistress Leila Sheboygan Female Domination Mistress Leila is a strict and sensual FemDom with a decided taste for the extreme! I am accepting submissive male and female applicants. I enjoy foot worship, slave training, strap-ons and total control. See all the possibilities and lots more pics on my ...

Submissive Male Seeks Dominatrix for Kinky Roleplay I'm Louie from Sheboygan, Wisconsin, and I'm a submissive male looking for a Dominant Female Mistress or Dominatrix to force me into submission. I want to learn how to please a Mistress properly and explore all kinds of kinky fetishes and desires. You can find me on FreeSexAds.com Alt profiles und...

Transgender Temptation in Sheboygan Hey there, I'm Arlee and I'm a transgender woman living in Sheboygan, Wisconsin. I love embracing my true self and being a part of the LGBTQ community. It's all about authenticity and acceptance, am I right? If you're looking for someone who's confident in their own skin and loves to have a good t...

Join Marylou for a Swinging Adventure in Sheboygan! Hey there, I'm Marylou from Sheboygan, Wisconsin! My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. We're always up for new experiences and meeting like-minded individuals who share our interests. You can find us in the swingers dating pro...

Raunchy Shemale Seeking Local Man for Wild Fun in Sheboygan I'm a sexy shemale named Gail who is looking for a man in Sheboygan, Wisconsin who can handle all my naughty desires. I love to be on top and take control, but I also enjoy getting down on my knees and giving mind-blowing blowjobs. I have a tight ass that loves to be pounded hard, and I can ride y...

Passionate Swingers Seeking Playmates in Sheboygan Hello there, I'm Celesta from Sheboygan, Wisconsin. My husband and I are fun-loving, open-minded, and kink friendly. We are always looking to add a little spice to our already hot sex life. You can find us on FreeSexAds.com Swingers Lifestyle Profiles under username celestasheb50429. We are a cou...

Hot Shemale in Sheboygan Looking for Some Naughty Fun Are you a man who craves the touch of a sexy shemale? Look no further, because I'm Brea, your ultimate fantasy come to life. I'm a horny shemale seeking a local man for some mind-blowing sex and unforgettable fun. 💋 I love nothing more than getting down and dirty with a guy who knows how to ha...

Kinky Fetish Fun in Sheboygan, Wisconsin I'm Darcy, and I'm a kinky girl from Sheboygan looking for some wild and adventurous playmates. I have a few fetishes that really get me going, like BDSM, domination, and roleplay. I love taking control and being a Mistress to my willing submissives. Whippings, spankings, and humiliation are all o...

Shemale Nightclubs Near You in Sheboygan, Wisconsin Shemale Nightclubs Near You in Sheboygan, Wisconsin Shemale Clubs Near You in Sheboygan, Wisconsin is a directory of trans-friendly nightclubs and bars. LGBTQ+ clubs come and go. We strive to keep this transgender clubs directory complete and rely on your input to help us do so. Please contact us...

Looking for Love and Adventure in Sheboygan! Hey there! I'm Daisey, a fun-loving transgender gal from Sheboygan, Wisconsin. 🌈 I wanted to put myself out there and see if love is waiting just around the corner. So here I am, writing this ad in hopes of finding someone special. Now, let me tell you a bit about myself. I have a bubbly perso...

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! Private Messag...

Kinky Fetish Fun with Gypsy Hey there, I'm Gypsy from Sheboygan, Wisconsin. If you're looking for some wild and adventurous fetish play, then I'm your girl! I love exploring all kinds of kinks and fetishes, from BDSM to roleplay to domination and submission. You can find me on FreeSexAds.com under the username gypsysh87067. I...

Euphoric Connections Await with Kelcey Hey there! I'm Kelcey, a proud transgender woman from Sheboygan, Wisconsin. I may not fit society's typical mold, but that's what makes me unique and fabulous. 🌈 I love embracing my true self and connecting with others who appreciate authenticity. Whether we grab coffee at Paradigm Coffee & Mu...

Raunchy Shemale Seeking Local Man for Wild Encounters Hey there, I'm a sexy shemale named Angelina looking for a hot man in Sheboygan, Wisconsin to have some steamy fun with. You can find me on FreeSexAds.com Shemale Profiles at angelinash26630. I love getting down and dirty with a guy who knows how to handle a tranny like me. I'm into everything from...

Mistress Savannah in Sheboygan // Domme seeking new sub Strict Mistress for sub in Sheboygan I am a strict Mistress, currently accepting applications for subs. My time is precious to Me and I won't waste it on people who are not serious about this. I am tall, slender and have long silky hair. My calm demeanor doesn't give away My desire to strongly puni...

TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Sheboygan Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...

Tantalizing Temptress in Sheboygan Hey there, I'm Larina from Sheboygan, and I have a unique fetish that drives me wild. I adore wearing latex from head to toe - the feeling of it against my skin is so exhilarating! It makes me feel powerful and sexy in a way that nothing else does. I'm a friendly and open-minded person who loves...

Experience Female Domination with Mistress Garnette in Sheboygan, WI Are you ready to submit to a powerful and seductive Femdom like myself? My name is Mistress Garnette, and I am here to fulfill all of your deepest desires and fantasies. From strap-ons to whippings, spankings to sissification, I will take control and lead you on a journey of ultimate submission. ...

Kinky Dominatrix seeks puppy to train DOMINATRIX SEEKS PUPPY TO TRAIN  Are you the submissive little puppy I have been looking for? I am A Power Domme looking for the one to meet my needs. I am on this site, because I know too often you seek an escape... with someone you can relinquish your power to. I know there's a lot of pressu...

Passion Seekers Looking for Playmates in Sheboygan! Hey there, I'm Bernadette from Sheboygan, Wisconsin. My husband and I are fun-loving, open-minded, and kink friendly swingers who love to explore our deepest desires. We are always looking for new playmates to join us in our sexy adventures. You can find us on FreeSexAds.com Swingers Lifestyle Pr...

Domme looking for male sub who wants to be owned Domme for male sub in Sheboygan I am Mistress Danielle. FemDom is My lifestyle, not something I do merely for fun. I have an opening in My dungeon for a submissive male. Send your photo along with an explanation of your kinks and fetishes and how you believe you can serve Me.  This is a serio...

Gorgeous, Passable Trans in Sheboygan 😍 Gorgeous Passable Trans MtF for Man in Sheboygan 😍 I transitioned 6 years ago at age 18. I am pretty, with long light brown hair, a nice figure and long shapely legs. I have brown puppy dog eyes and kissable lips. Check my profile @TransFaye24 for pics and prepare to be stunned!  I'm ...

Unveiling My True Self: Shirley's Transgender Dating Ad Hey there, I'm Shirley, a confident and proud transgender woman from Sheboygan, Wisconsin. I love embracing my true identity and being a part of the LGBTQ community. 🏳️‍🌈 I'm looking for someone who is open-minded, kind-hearted, and ready to explore life's adventures with me. Let's grab...

Hot Shemale in Sheboygan Ready to Play Are you looking for a wild time with a sexy shemale? Look no further, because I'm Lesya and I'm ready to show you a good time. I'm a horny tranny seeking a local man for some hot and steamy fun. If you're into getting down and dirty, then I'm the girl for you. I love giving blowjobs, getting fuck...

Sexy Transgender Seeks Connection in Sheboygan Hey there! I'm Marlane, a proud transgender woman from Sheboygan, Wisconsin. I love embracing my true self and being part of the LGBTQ community. I enjoy exploring new places in town like Blue Harbor Resort or taking a stroll along Lake Michigan. If you're looking for someone who is fun, open-mind...

Tempting Offer: Explore Your Fetishes with Robbyn from Sheboygan Hey there! I'm Robbyn, a friendly and open-minded gal from Sheboygan who loves to explore all sorts of kinks and fetishes. One of my favorite fetishes is foot worship - there's just something so sensual and exciting about having my feet pampered and adored. I'm always up for trying new things, s...

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Passionate Swingers Looking for Playmates in Sheboygan Hello there, I'm Fran from Sheboygan, Wisconsin. My husband and I are fun-loving, open-minded, and kink friendly swingers looking to spice things up in the bedroom. We love exploring new experiences and pushing our boundaries to new heights of pleasure. You can find us on FreeSexAds.com Swingers...

Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Sheboygan Beautiful Brandi. If you're attracted to the female form then you will want to message me @ BrandiTS27. I'm pre-op, tall, slim and beautiful with 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your naughty f...

Hot Shemale Audra in Sheboygan Ready to Play and Fulfill Your Wildest Fantasies! 🔥🍆💦 Are you looking for a naughty shemale who knows how to have a good time? Look no further, because I'm Audra, a sexy trans woman in Sheboygan who is ready to rock your world. Whether you're into a top or bottom, I can fulfill all your desires and more. 💋👠 I love getting down and dirty with a...

Hot Shemale in Sheboygan Looking for Some Naughty Fun Are you a man in Sheboygan looking for a sexy shemale to play with? Well, look no further because I'm here to fulfill all your wildest fantasies. My name is Louisa and I am ready to show you a good time. Whether you're into getting your cock sucked, fucking my tight ass, or exploring new kinks, I'...

27 y/o Sexy Hung Crossdresser in Sheboygan Hung Crossdresser for Male in Sheboygan Hey, I go by Selena when I'm cross dressed. I love being feminine and servicing my man!, I'm age 27, well hung and so cute when I'm dressed up!! What more could you want in a gurl?!! View my pics and message me @Selena27femCD so we can talk and meet for a sex...

A Unique Fetish Experience Awaits with Van from Sheboygan! Hey there, I'm Van from Sheboygan, Wisconsin, and I have a unique fetish that I absolutely love! I enjoy being a foot worshipper, finding pleasure in pampering and adoring my partner's feet. It's a special kind of intimacy that brings me joy and fulfillment. I'm a submissive guy who would love to...

Well Endowed Shemale for Man in Sheboygan Hung Shemale for Man in Sheboygan I am Blanca. I can provide top or bottom service. Bareback if you're clean. Love oral sex both giving and receiving. Say hello cause I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me privately at BlancaShemale32 for my latest uncen...

Seeking Local Man for Shemale Fun in Sheboygan Are you looking for a hot shemale to fulfill all your wildest fantasies? Well, look no further because I'm Katti, a sexy shemale from Sheboygan who is ready to have some naughty fun with a local man like you. When it comes to sex, I love it all. From being a top and dominating you to being a bott...

Passionate Swingers Ready to Play in Sheboygan, WI Hey there, I'm Jamie, a seductive and adventurous swinger from Sheboygan, Wisconsin. My husband and I are fun-loving, open-minded, and kink friendly. We love exploring our deepest desires with other like-minded couples who share our passion for the swinging lifestyle. You can find us in the FreeSe...

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Submissive Male Seeks Dominatrix for Kinky Fun Hey there, my name is Darryl from Sheboygan, Wisconsin. I am a submissive male looking for a Dominant Female Mistress or Dominatrix to force me into submission and teach me how to please a Mistress properly. I can be found on FreeSexAds.com Alt profiles under username darryl82144. I enjoy various s...

Join Jessamine for a Sensual Adventure in Sheboygan! Hello there! I'm Jessamine, a fun-loving swinger from Sheboygan, Wisconsin. My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. We enjoy meeting new people who share our passion for excitement and adventure. You can find us in the swingers d...

Passion Seekers in Sheboygan - Carmelita's Swinging Adventures Hello there, I'm Carmelita from Sheboygan, Wisconsin. My husband and I are fun-loving, open-minded, and kink-friendly swingers looking to spice things up in the bedroom. We are always on the lookout for new playmates who share our passion for the lifestyle. You can find us on FreeSexAds.com Swing...

Swinging Couple in Sheboygan, New to the Lifestyle Swinging Couple in Sheboygan We are a swinging couple in Sheboygan, Wisconsin. New to the lifestyle but eager to learn and explore the swingers world! About Him He is Jeff, a former military, larger, fit, age 29. He works out daily, loves trucks, camping, hunting, fishing and all the usual guy th...

Passionate Swingers Looking for Playmates in Sheboygan Hello there, I'm Marjory from Sheboygan, Wisconsin. My husband and I are a fun-loving, open-minded couple who love to explore our kinks and fantasies with like-minded individuals. We believe that life is too short to not indulge in the pleasures of the flesh, so we're always on the lookout for new...

Explore Your Wildest Desires with Marjory Hey there! I'm Marjory from Sheboygan, Wisconsin, and I have a unique fetish that I absolutely adore. I love indulging in role-playing scenarios where I can take charge and be in control. It's such a thrill for me to explore power dynamics and push boundaries in a safe and consensual way. I'm a f...

DOMME AVAILABLE for private Femdom and DISCIPLINE Experienced Dominatrix for Sheboygan Submissive Experienced Dominatrix seeks submissive, ready and willing to learn discipline from a loving but strict Mistress. Contact me @ SheboyganDommeX if you are available and willing to serve my needs. Available For: Discipline  Corporal Punishment...

Sweet and Sensual Transgender Beauty Looking for Love in Sheboygan! Hey there! I'm Kati, a transgender woman living in Sheboygan, Wisconsin. I may not be your typical girl, but that's what makes me unique and special. I love embracing my true self and being a part of the LGBTQ community. 💖 I'm looking for someone who is open-minded, kind-hearted, and ready to ...