Home > Madison, Wisconsin > Casual Encounters


Madison, Wisconsin Casual Encounters

Find Madison, Wisconsin casual sex ads for spontaneous hookups, friends-with-benefits, or wild one-night stands. These casual encounter listings are posted by real people seeking no-strings sex in Madison, Wisconsin. Join now and explore your local adult scene - totally free.

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

  • February 4th, 2026
  • Kinky Trans Woman Seeks Bondage Play Partners For Naughty Fun.Kinky Trans Woman Seeks Bondage Play Partners For Naughty Fun. I'm a kinky transgender woman with a craving for bondage play. I'm looking to explore my wild side and have some fun with men who are into the same. ? Let's get creative with ropes, cuffs, and all things naughty. I want to feel your hands on me, taking control and showing me who's boss. ? Don't be s...
  • Wild Lesbian Group Fun - LetWild Lesbian Group Fun - Let's Get Down And Dirty! I'm on the lookout for a wild time with a group of sexy ladies who are down to fuck. I want to feel your bodies pressed against mine, exploring every inch with eager hands and hungry mouths. Let's satisfy each other's cravings and make all our wildest fantasies come true. No need to be shy - I'm all...
  • Lusty Hottie for Lesbian, Bisexual or Bicurious Woman in MadisonLusty Hottie for Lesbian, Bisexual or Bicurious Woman in Madison My name is Allison and I am medium height and weight, and fit with more than ample breasts that love female attention! So, like I am 22 and I am new here since December. I like dancing and movies. I'm sexually adventurous and kink friendly, also party friendly but no hard drugs plz. You want to talk...
  • Heyyy! 😍 ItHeyyy! 😍 It's Crystal 27 y/o Hot Trans Fem | Madison, Wisconsin Heyyy there! Thanks for checking my ad. I'm Crystal and I am 27. I'm fairly new to the Madison area and want to get to out explore the area. I'd love make some new friends and maybe find romance! I am a masseuse with great hands, hot body, in great shape, and well hung and totally functioning. If yo...
  • Master looking to add a couple of new boysMaster looking to add a couple of new boys 10 years experience as a Dom. I have my own home with a well equipped basement dungeon. Fully sterilized and all equipment is top grade. I have my own sterilizing units and you will not find one germ in my room. STD free and require the same.  I want a weekend boy who can serve Me. If you have...
  • Shemale Fantasy? Let Me Take Care of That. Shemale Fantasy? Let Me Take Care of That. "Experience your shemale fantasy in real life!"  Hi, I'm Gia, a shemale who loves introducing male trans admirers to the sexy world of shemale sex. I'm available to hook up with you in Madison! No strings and no drama - just great times, so join my page free for instant access! Shemale Gia'...
  • LetLet's Make Your Anal Fantasies A Reality Tonight ??? I need a guy who's down to pound my backdoor ??. I've been craving some anal action lately and I need a man who can handle it. I want someone who knows how to take control and give it to me hard. No holding back, just pure pleasure and ecstasy. If you think you're up for the challenge, hit me up. Le...
  • LetLet's Get Wet And Wild: Seeking Piss Play Partner ???? I need a guy who's into piss play ?. There's something about letting loose and getting wet that really gets me going ?. I want to explore this kinky side of me with someone who's just as eager to dive in. No holding back, no shame, just pure uninhibited fun ?. Let's push boundaries and see where our...
  • Shy Guy Wants To Meet Shy Gal In MadisonShy Guy Wants To Meet Shy Gal In Madison Hello, I'm Eric, a male, age 34, tall and fit, looking for gal, 26+ age. I'm a bit reserved and on the shy side so if you are also, that's a plus. I warm up once I start to feel comfortable. I will be patient and you can feel free to take as much time getting to know me as you want. I have a lot of ...
  • I Tried to Be Good But These Huge Tits Deserve a Big Cock! I Tried to Be Good But These Huge Tits Deserve a Big Cock! Big Tits, Seeks Hung Guy in Madison I am Destiny. Not my real name but I'll let you know in time. I can entertain you and make you laugh but I don't take myself too seriously! I have a bubbly personality, big tits that love to be touched and I love to have a good time. I just like to kick back and...
  • Anonymous Pounding Wanted. Come Over, Fuck Hard, Leave Silently. No Strings.Anonymous Pounding Wanted. Come Over, Fuck Hard, Leave Silently. No Strings. I'm looking to get fucked anonymously. I want someone to come over, pound me hard, and leave without saying a word. No names, no small talk, just pure pleasure. I'll be waiting for you with my ass up and ready to be used. Let's make this a quick and dirty encounter that we both won't forget. Discret...
  • Dive Into The Forbidden World Of Pleasure With Me Tonight!Dive Into The Forbidden World Of Pleasure With Me Tonight! I'm looking to anonymously fuck with a man who can handle my wild side. No strings attached, just pure pleasure. I want to explore all of our deepest desires and make each other scream with ecstasy. Let's push each other to the limit and leave nothing to the imagination. I crave the thrill of the un...
  • LetLet's Explore BDSM Together - Seeking Kinky Partner For Wild Fun I need a kinky partner who's down to explore some BDSM play with me. I'm all about pushing boundaries and trying new things in the bedroom. ?️ Whether you're into being dominated or taking control, I'm game for it all. Let's unleash our wild sides and fulfill each other's fantasies. ? Safety and c...
  • Seeking Experienced Dom For Kinky BDSM Play, LetSeeking Experienced Dom For Kinky BDSM Play, Let's Explore Together. I'm craving some BDSM play with a man who can handle my wild side. I want to explore all the kinky fantasies we both have ?. Let's push each other's boundaries and see where it takes us. I need someone who isn't afraid to take control and dominate me in the bedroom ?. Safety and consent are key, but...
  • LetLet's Get Kinky: Trans Woman Wants Dick Sucked By You I'm a trans woman looking to get my dick sucked by a willing guy. I'm clean, chill, and down for some fun ? Let's make each other feel good and enjoy ourselves. No strings attached, just a good time between two consenting adults. I'm open to all types of guys, so don't be shy! Hit me up if you're in...
  • Naughty Girl Wanted For Hard Pounding And Wild Fantasies Fulfilled.Naughty Girl Wanted For Hard Pounding And Wild Fantasies Fulfilled. I need a naughty girl who's craving to be fucked until she can't take it anymore. I want to pound your pussy hard and deep, making you scream with pleasure. Let's explore each other's wildest fantasies and make them a reality. I'll make sure you're satisfied in every way possible ?. No need to hold ...
  • Wild Night Of Passion With Multiple Ladies, Exploring Deepest Desires.Wild Night Of Passion With Multiple Ladies, Exploring Deepest Desires. I need a wild night of passion with multiple ladies at once. I want to feel every inch of your bodies pressed against mine, exploring each other's deepest desires. Let's lose ourselves in the heat of the moment as we fuck each other senseless. I crave the taste of your skin, the sound of your moans ...
  • Sensual Trans Woman Gives Mind-blowing Blowjobs - Satisfaction Guaranteed!Sensual Trans Woman Gives Mind-blowing Blowjobs - Satisfaction Guaranteed! Hey, I'm a trans woman with a little extra something down below, looking to give mind-blowing blowjobs to men who appreciate it. I love the feeling of being on my knees and making you feel good. ? Let me show you what I can do with my mouth and tongue - you won't be disappointed! Whether you're stra...
  • Just Trying To Get Pounded OutJust Trying To Get Pounded Out Looking for a hot gay man to satisfy all my dirty desires. I'm Kendrick, a horny guy seeking some male-on-male fun with other gay, bisexual or bi-curious guys. You can find me in the SpunkPage.com M4M profiles under username kendrickal64499. I love getting my cock sucked and balls licked while I mo...
  • Seeking Men For Anonymous Head - Pure Pleasure, No Strings Attached.Seeking Men For Anonymous Head - Pure Pleasure, No Strings Attached. I need to give some anonymous head to men who need it. ? No strings attached, just pure pleasure for both of us. I'll make sure you leave satisfied and wanting more. Let's meet up in a discreet spot and get down to business. I love the thrill of not knowing who you are, just feeling your excitement ...
  • LetLet's Get Wild: Anonymous Lesbian Encounter, No Strings Attached Satisfaction. I'm craving some anonymous fun with another woman who's down to fuck without any strings attached. I want to feel your body pressed against mine, exploring each other's desires and fulfilling our wildest fantasies. Let's lose ourselves in the heat of the moment, letting passion take over as we explo...
  • Seeking Anonymous Stranger For Wild, No-strings-attached Pleasure Tonight ?Seeking Anonymous Stranger For Wild, No-strings-attached Pleasure Tonight ? I need a stranger to anonymously fuck. No names, no strings attached - just pure, unadulterated pleasure. I want to feel your hands exploring every inch of my body, driving me wild with desire. Let's lose ourselves in the moment, letting our primal instincts take over. I crave the excitement of a fo...
  • Ready For Anonymous Head? No Strings Attached, Just Pure Pleasure.Ready For Anonymous Head? No Strings Attached, Just Pure Pleasure. I need for some no-strings-attached fun. I'm looking to give anonymous head to a guy who's down for a good time. ?? Let's meet up somewhere private, get straight to business, and part ways without any questions asked. I don't need to know your name or anything about you - just looking to satisfy eac...
  • Mind-blowing Blowjob Specialist Ready To Make You Throb With Pleasure!Mind-blowing Blowjob Specialist Ready To Make You Throb With Pleasure! I'm in the mood to give a mind-blowing blowjob ?. I've been craving to feel you throb in my mouth and hear you moan with pleasure ?. Let me show you my skills and make you beg for more. I'll take my time and work every inch of you until you explode with ecstasy ??. No need to rush, just sit back, re...
  • Shy Crossdresser Seeks Friend for Discreet Dressing, Possible Dates | Madison, Wisconsin AreaShy Crossdresser Seeks Friend for Discreet Dressing, Possible Dates | Madison, Wisconsin Area Hello. I'm a married crossdresser in the Madison area. My fem name is Gloria. I'm 28 years old, clean and disease free. I am passable in appearance and voice but the problem is that my wife doesn't approve. She knows but doesn't want anything to do with my crossdressing. I REALLY need to let my fem ...
  • Madison Lesbian, Bisexual & Bi-curious Women! JOIN FREE Madison Lesbian, Bisexual & Bi-curious Women! JOIN FREE FEMALE ON FEMALE PASSION! Local Lesbians, Bisexuals & Bi-Curious Women!  SIGNUP FREE: INSTANT W4W ACCESS! Uncensored Photos Swap Your Pics Live Web Cams Private Messages Sext & Hook Up! View Females | Upload & Swap Pics | Sext Messages "Be...
  • Craving Pussy Pleasure: LetCraving Pussy Pleasure: Let's Explore Fantasies And Make Each Other Moan. I'm craving to have my pussy eaten by a sexy woman who knows how to make me squirm with pleasure. ? I want to feel your tongue teasing and tasting every inch of me until I can't take it anymore. Let's explore each other's bodies and fulfill our wildest fantasies together. No judgment, just pure blis...
  • Fuck Me Hard and Deep - PrenticeFuck Me Hard and Deep - Prentice Are you a horny gay man looking for some hot and steamy action? Look no further, because I'm here to fulfill all your wildest fantasies. My name is Prentice, and I'm a gay man seeking other gay, bisexual or bi-curious guys for some mind-blowing male-on-male fun. I love getting my tight ass pounded ...
  • Hung Man for Male Action in Madison!Hung Man for Male Action in Madison! Nasty As u Want!  Hey, I'm Mark. I'm clean and discreet. Always Wild, Fun, Fetish Friendly and Erotic. I'll be waiting to please! Single guys or male couples. Cucks and fetish always welcome. I love all kinds of sex and kinks so don't be shy.  Hot Stress free zone. My pics are 1...
  • Simon Hot Male for Male or Couples in Madison. Call for a night of joy!Simon Hot Male for Male or Couples in Madison. Call for a night of joy! Contact me for your dream night. Male for male or couples. I am Simon and I can do whatever you want to do. Top or bottom. Kinks and fetishes are fun to explore. Shy or just curious? That's my specialty! Let me introduce you to male on male sex the way it should always be. View my online profile and...
  • Throbbing Surprise: Trans Woman Seeks Horny Men For Wild, Anonymous Fun.Throbbing Surprise: Trans Woman Seeks Horny Men For Wild, Anonymous Fun. I'm a sexy transgender woman with a throbbing surprise down below, looking to anonymously fuck with some horny men. I'm not interested in small talk, just want to get straight to the point and have a wild time together. Let's explore each other's bodies and fulfill our deepest desires without any st...
  • Fuck me hard and make me squirt, IFuck me hard and make me squirt, I'm Roz When it comes to getting down and dirty, I'm your girl. I love nothing more than a good, hard fuck that leaves me begging for more. Whether it's on my back, bent over, or riding you like a wild cowgirl, I guarantee you won't be disappointed. I have a few kinks up my sleeve as well. I love being dom...
  • Lipstick Lesbian 💋 Ready for Butch WomanLipstick Lesbian 💋 Ready for Butch Woman Lipstick Lesbian seeks Butch Woman 💋 Lipstick lesbian wants to meet an awesome Madison area butch woman to share passion and fun. I am 25 and definitely femme. Long strawberry blonde hair, on the shorter side, fit and curves in the right places, but not overweight. You are preferably butch or le...
  • Powerful African-Queen Dominatrix in Madison, WisconsinPowerful African-Queen Dominatrix in Madison, Wisconsin Professional Domme Desiree is interviewing subs. My Madison dungeon is well equipped, as this is My life, not a hobby. I am a strong, powerful shemale who will take charge and maintain total control. Your obedience will be required at all times and you will learn to serve Me. I am the top and well e...
  • Craving Woman Wanted: Let Me Eat Your Pussy Like Never Before.Craving Woman Wanted: Let Me Eat Your Pussy Like Never Before. I need a woman who's craving to have her pussy eaten like never before. I want to make you squirm with pleasure as my tongue works its magic on you. Let me show you just how good I am at making you moan and writhe in ecstasy. ?? I promise to take my time and savor every delicious moment, teasing an...
  • Anonymously Explore Pure Pleasure With Me - No Strings Attached Fun!Anonymously Explore Pure Pleasure With Me - No Strings Attached Fun! I'm looking to fuck anonymously with a woman who's down for some no-strings-attached fun. I want to feel your body pressed against mine, exploring every inch of you as we lose ourselves in pure pleasure. Let's make it all about satisfying our desires and indulging in the raw, primal passion that com...
  • Kinky Bondage Play: Explore Your Limits And Surrender To PleasureKinky Bondage Play: Explore Your Limits And Surrender To Pleasure I'm looking to bondage play with a woman who's into exploring their kinky side. I want someone who's willing to be tied up, blindfolded, and teased until they can't take it anymore. ? We can use ropes, handcuffs, or whatever else gets you going. I'll make sure to respect your limits and boundaries w...
  • Hot Female for Great Sex @KellieAsheHot Female for Great Sex @KellieAshe Check my profile KellieAshe  Send your recent pics for mine.  I can't believe I'm back in these ads but here we both are... Is it fate? About me: I am a very good woman and I would love to meet a fun man who can enjoy a good conversation, have some fun and make me laugh. I have integ...
  • LetLet's Get Naughty: Anonymous Head For Your Pleasure Only! I need to give some anonymous head to guys who need it. I'm all about keeping things discreet and drama-free, just looking to have a good time and satisfy your needs. ?? Whether you're curious, straight, or bi, I'm here to help you out. No strings attached, just pure pleasure for both of us. Let's m...
  • LetLet's Dive Into Ecstasy Together, Fulfilling Your Wildest Desires Now. I need a sexy lady who's down to let me feast on her sweet pussy. ? I want to taste every inch of you and make you moan with pleasure. Let's explore each other's bodies and get lost in the moment together. I promise to make you cum like never before. ? No need for small talk, just pure passion and d...
  • Trans Woman Seeks Hung Men To Destroy Her Ass, No Small Talk.Trans Woman Seeks Hung Men To Destroy Her Ass, No Small Talk. I'm a transgender woman with a craving to get my ass destroyed by some well-hung men. I want you to pound me hard and make me scream with pleasure. I'm looking for guys who know how to handle a girl like me and can give it to me rough. No need for small talk, just come over and let's get down to bus...
  • Sexy Young Woman for First Lesbian Experience in Madison 🥰Sexy Young Woman for First Lesbian Experience in Madison 🥰 Hi I'm Melodie! I am 19 and looking for my first lesbian experience. 🍑 My family has been cool and supportive. My mom suggested I put an ad out online so here I am. Wait a minute... how does my mom know this site?!! 😬 hahah, anyway, here goes.   I am into clubbing but also like quie...
  • Fuck my Tight Ass OswellFuck my Tight Ass Oswell Are you a horny gay man looking for some hot male-on-male action? Look no further because I'm your guy! My name is Oswell and I'm ready to get down and dirty with you. You can find me in the SpunkPage.com M4M profiles under username oswellman33545. I'm a bottom looking to have my ass fucked hard by...
  • Jaw Dropping Hot Lesbian for Female Lover in MadisonJaw Dropping Hot Lesbian for Female Lover in Madison Did my pic get your attention? I hope so because I am looking for my perfect female partner. Someone who is fun, attractive and smart. She should be easy to talk to, fun-loving, laid back and passionately attentive to her partner, just as I will be for you. Want to take a road trip? Settle in for so...
  • Big Titties, Love To Be Tit Fucked!Big Titties, Love To Be Tit Fucked! Looking for a wild time? Well, look no further because you've found me, Jammie! I love to get down and dirty in the bedroom, exploring all kinds of naughty fantasies. Whether you're into blowjobs, anal play, or just some good old-fashioned fucking, I'm your girl. When it comes to sex positions, I'm...
  • II'm a Dirty Little Slut Looking to Ride Your Hard Cock Are you looking for a wild time with a naughty girl who loves to get down and dirty? Look no further because I'm Rosalinda, and I'm here to fulfill all your wildest fantasies. I love to suck on a big, throbbing cock until it explodes in my mouth. The feeling of warm cum dripping down my chin gets me...
  • I Want to Ride Your Huge Cock and Make You Cum Hard, BabyI Want to Ride Your Huge Cock and Make You Cum Hard, Baby Are you looking for a wild time with a naughty girl who loves to play? Well, look no further because I'm Erika and I'm ready to rock your world. I have a tight pussy that's just begging to be fucked hard. I love giving sloppy blowjobs and feeling your huge cock deep in my throat. Let's make each oth...
  • Seeking Hot Sex and Fun for Allison27Madison 💋Seeking Hot Sex and Fun for Allison27Madison 💋 Hey, my name is Allison. I am looking for no strings sex and fun with an exciting man in the Madison area who can make me laugh and who enjoys walks in the park, romantic dinners and hot sex! I know it sounds cliché, but I am a lady on the streets and a tramp in the sheets!  💋 S...
  • 9 Inch TOP Only Trying To Blow My Load.9 Inch TOP Only Trying To Blow My Load. Are you a horny gay man looking for some hot male-on-male action? Look no further! I'm Lawrence, and I'm a hung top who loves to dominate and pound a tight ass. I can be rough or gentle, depending on your preference. I enjoy deepthroating, rimming, and using toys like dildos to enhance the experienc...
  • LetLet's Make Sparks Fly And Fulfill Our Wildest Fantasies Together I'm looking to have my pussy fucked with a woman who knows how to handle me just right. I want someone who can make me scream with pleasure and leave me begging for more. I'm not interested in any games or drama, just pure, unadulterated fun. If you think you can handle me, then let's make it happen...

  • Home > Madison, Wisconsin > Casual Encounters