Madison, Wisconsin Sex Ads and Adult Classifieds

Madison, 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

  • August 7th, 2025
  • Wife Swap! Let's Swing in Madison Attention Swingers in Madison! Adventurous, attractive, athletic swinging couple in the Madison area seeks swinger hookups for social activities and to explore the local swinging lifestyle. Let's go to the clubs and spend time socializing for fun and passionate sex. Kinks are welcome with us! He i...
  • A monster in the sheets, but a lady in the streets... Hello men, I'm Lilith a 27 year old sexy femme, fully functional, passible, sexy and hot to trot trans. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Madison area and are interested then drop me a line and introduce yourself. You can ...
  • Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Madison Area Hi, my fem name is Gloria. I'm a married crossdresser in the Madison area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but my wife doesn't approve. I REALLY need to let my fem side out to play! I'm seeking cross dressing...
  • I Need a Sexy Man to Tame Wild Willy! Hung Madison Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Madison 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 see a ...
  • I wanna be your friend and lover Mature black man in Madison Howdy, my name is Samuel and I am a mature gentleman looking for a lady who is smart, funny and outgoing. I am 52, widower after 28 years, no kids. I am into riding my bike, the gym, and fishing on weekends. There is just one thing missing - maybe it's you! Do you like d...
  • Italian single girl looking for love Ciao amore mio! Sono nel mercato per trovare un bell'uomo muscoloso e carino. Se sei carino e in forma mandami un testo per una data! (AngelicaXOXO) Hello, my love! I am in the market for finding a handsome man who is muscular and cute. If you are cute and fit send me a text for a date! (Angel...
  • I Need a STEAM ROLLER Baby!!! I want you to inject my soul with that sweet lover's pole till there ain't much of me left behind. I'm your whore so just F my brains out tonight. I'm a naughty trans looking for a top big boy to have his way with me. So it's heels and ass up and earth moving sex the hard way. That's the way I like ...
  • Shy 41 yr old guy Shy But Romantic in Madison 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...
  • Newly Out Looking for love Newly Out Lesbian in Madison I have only been out for a few months and I am totally new to the dating scene. I have no idea even what to say or where to start! I will tell you a little about me. I am a youth worker and I have a college education. I am 26 and sort of tomboyish but I do wear make up ...
  • Get Over Here Boy! Single and Sexy in Madison Baby! Hannah here in Madison looking for a friend with benefits. Hey just so you know I'm not just another piece of ass. That's not why I'm here, to just add to your body count. At the same time I will not tie you down in a relationship you don't want either. Let's be cas...
  • Tantalizing Tina with a HUGE W33NAH! Madison Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Madison men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  About me: 2...
  • MALE STUD FOR HOT ACTION - Madison Area 😈🔥👬 Get Ready for the Fuck of Your Life! 🍆 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. 🍆💦 I'm a kin...
  • Slovak woman lonely and looking for guy in Madison Dark, sultry and tall, very well built, Slovak woman is here to please and be pleased. I desire for long term friendship, fun and love. My English is getting better so send photos and message me here @TmavoZmyselná Tmavá, zmyselná a vysoká Slovenka   Tmav&eac...
  • Superb Shemale in Madison... T-Girl for NSA Encounters in Madison When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Madison. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck and ...
  • Fitness Freak has sporty body Hi, this is Teri! I love to work out. I run, I lift weights and I am fit. I am medium height and weight, toned and tan. I have brown eyes and blonde hair. I want a woman who is her own person and financially responsible. If you are a fun type who loves an athletic female partner, take a look at my o...
  • Latina Beauty needs love in Madison Hola señoras. Soy Juanita y soy local en esta zona. Tengo un trabajo y tengo mi propio auto. Puedo viajar para conocerte si quieres conocerte a mitad de camino. enviarme un mensaje @Juanita4love.  Hello ladies. I am Juanita and I am local in this area. I have a job and I have my ow...
  • Click here - Add to Cart. Madison Single Dad for Fun That's my mom in the pic with me BTW. I'm Jonah here in Madison 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...
  • Handsome, tall and tanned guy wants to meet shy woman Shy Guy for Shy Gal in Madison 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. I have many interests and like new experiences. I want to meet a mature woman for fun, laughter and more. Check out my profile f...
  • CRYPTO GIRL WILL FUCK YOU TO THE MOON! 🤑💦 Crypto Girl for Crypto Guy in the Madison Area Hello crypto lover! 🤑 I am Jeanette. I'm good at sex and very creative. I'm into trying different positions and locations. Love exploring kinks of all types. Nothing is off limits! Some of my fav kinky stuff is BDSM, strap-ons, anal sex, role play, ...
  • Curvy Babe Needs a Naughty Massage in Madison!... 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 Madison 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 t...
  • Intense, vibrant and dark haired beauty, WLTM handsome fun guy Intense Dark Haired Beauty in Madison Hey, I'm Janey and I'm still looking. I'm kind of bored and need new friends and maybe some romance. I have dark hair, soft skin, sultry eyes and a great smile to make you happy. How about you? Why not call and let's see where things go? Message me now #J...
  • August 6th, 2025
  • Madison Cougars and Cubs Cougars and Cubs in Madison Browse thousands of cougars profiles and join free! ...
  • Carmel skinned beauty waiting for you in Madison Woman seeking woman in Madison I am Brandi and I am busty and attractive. I am carmel colored from a mixed background and I am looking for the woman of my dreams. I am passionate and love sex. I'm seeking a fun-loving woman in the area who wants to enjoy the fun things in life. If you meet that de...
  • I BREAK TWINKS and turn them into MY SEX PUPPETS! Big top bone thug gonna wreck you and make you twinks tap out! Looking for sissie boi to use and abuse here in the Madison area. All is fair and shit as they say. Needless to say I'm the dominant and controlling type in any situation. Your gonna get the big one rough and deep honey! No screamers ple...
  • Nice but Naughty 30 year old seeking affection and a good time I am half Latina and half European and have moved here recently. I am lonely, trying to assimilate and I would like to meet a very nice man who wants to play and enjoy life together. Text me for a date! (Naughty30luv) I'm naughty but nice, love a good time, party friendly, have recent pics to share...
  • Sweet new girl in town Sweet and Kind in Madison I am sweet and kind and I want to meet a kind hearted man. I am part Asian and I have long sensual hair and a good set of curves. Send me a message @NewGirlEve if you would like to meet. xoxo  Eve 👄...
  • Even Good Girls Need to be Spanked! (sometimes) Hey boys I'm Cheyenne here in Madison looking for a guy who's fun in bed. (and out) Didn't you get the memo? Good girls need to be spanked too! Yes, it's true - believe it or not! We love you to pull our hair, bite our lip, slap our hanging titties and spank our ass before, during and after sex. Act...
  • Lets Go Playah! Madison Boys Come Out and Play! Mindy here in Madison ready to play with a man who has skills. This game ain't for sissies or mommas boys. I know what I want and you know what you want so this whole thing should be uncomplicated and simple. You know the game, it's straight forward and goes as follo...
  • Hey Ya'll Its a 3-Way Booty Call! Try an Ebony Threesome With Me! Vera here in Madison looking for a few good swingers! Or, at least one good couple. LOL  If you like hot chocolate and a big booty here I am. I got some hefty hooters too that will make your mouth water and hypnotize you so I can take advantage of you. Hit it an...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Madison! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Madison!  No strings - just great times, so join my page free for instant access! Shemale Gia's Madison Sexbook @ShemaleGia27 Photos: 42 V...
  • Keep Calm And Have A Threesome in Madison! Swinger Couple in Madison I'm Daily and my hubby is Don, we are in our 30's, live here in the Madison area and are swingers looking for a sexy man and or woman. We love role play as you can probably tell from our pics. We can be a little kinky I suppose, but mostly we are into adult role play and N...
  • Daniel 28, Plumber, recently new to area 28 y/o Man New to the Madison Area For Dating I am fairly a plumber by trade. I am looking for new people to meet in the Madison 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...
  • Let's Play Cock, Paper, Scissors!... Gay Man Looking for Fun in Madison Now that I got your attention. Hi I'm Graham, a gay man here in Madison and I'm looking for a man who likes to play sexually charged games. I'm 28 years old, black hair, brown eyes, 6'0, well endowed, (8+inches) hispanic, single, love to party, no pets, ...
  • Do you know the difference between a dick and a bucket of popcorn? You don't know? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Madison tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than...
  • I just want to enjoy life and practice safe sex Hot Woman for Great Sex @KaycieMaine Check my profile KaycieMaine I am a very good woman and I just want a man who can hold down a good conversation and make me laugh. I have integrity and I am looking for true, real love, passion, transparency and honesty. Please respond only if you are look...
  • Lithuanian Lady Likes Lady Love Seeking a beautiful woman to be with. You must be kind and funny and like any kind of music. Tatts and piercings are a turn-on! I love to sit and watch movies and I love music, exploring the Madison area and eating out. Messsage or text @Natalia4LadyLove xoxo, Natalia Username: @Natalia4LadyL...
  • BBW Lesbian in Madison Sucker for love BBW Lesbian in Madison Hey ladies, My name is Joanne and I suck at love! Ok, what I mean is, I love to suck. Definitely a 'boob' woman and if you got em I like em. Big, small or medium, it doesn't matter. I'm ready to spoil your body! Message me @JoanneBBWfem. Serious dates only please. Send y...
  • Latina Chica New in town New in Madison 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 have...
  • Cutiecumber is looking for her fineapple Me, I'm 33 years old, independent, profession is banking, recently out and wanting to take things to the next level with the right sort of understanding girl. Not exactly looking for serious right away. I'm testing the waters here in Madison so to speak. I don't date co-workers so meeting other lesb...
  • 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...
  • Latina chick looking for the love of my life. Isabel Para Mujero Por favor, dime que estás ahí fuera. Me llamo Isabel y soy una lesbiana solitaria que busca su amor. Ven a buscarme. Sabes que te estoy esperando. Hablo bien inglés, pero necesito mejorar un poco más. Ayúdame a que te ayude. Envíame un mensaje a IsabelParaMu...
  • Any Irishmen Here in Madison? Well, step right up then gentlemen I'm from Ireland and live here in Madison for two years now. I am awaiting my naturalization papers to go through so I can become a US citizen. Currently I work in catering mostly for weddings. It's a good enough job, but I'm not here to tell you all about my life ...
  • Don't ever play leap frog with unicorns! Hi I'm Claire, a cougar here in Madison to show young men that with age comes wisdom like in the headline above. lol I am willing to share my acquired knowledge with eager cubs who want to be shown a better way. Of course most of the knowledge I have would be sexual in nature since that is why I'm h...
  • Gay Russian Bear New to Madison... My English is not so good yet. I am Vlad from Moscow, Russia and want to find gay young man for sex in Madison. 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 are...
  • I want to be a whore I am a transexual very hot. Good with my mouth and my ass. Comment on my photos. I would appreciate it if you downloaded my photos and share me with other men in the Madison area. Click here and come see me anytime!...
  • BLAZED HOOKUPS - Party Friendly in Madison Where's the Party in Madison? I'm Marijane @MarijaneBlazed26 and I'm looking for a smoking hot encounter here in the Madison area. I love getting lit up and then down and dirty with a generous man - nothing turns me on more than a good old-fashioned fuck when I'm high. Whether you want to explore a...
  • 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! @Rendezvous29Madison Send me yo...
  • 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 Madison 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 ne...
  • Keep Calm and Pet the Kitty... Angie here in Madison 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 si...
  • FtM seeking Princess Bride in Madison FtM seeking Woman in Madison Hi, I'm Andy, age 33, FtM mixed-race transgender man living in Madison. 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...