Exciting Casual Hookups in Madison, Wisconsin!

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Welcome to CasualMeetupz.com, your go-to site for finding casual hookups in Madison, Wisconsin! If you're tired of swipe culture and want to meet like-minded individuals for thrilling encounters, you've come to the right place. Madison is not only home to beautiful lakes and vibrant parks, but it also offers plenty of cozy spots to spark a connection. From the lively atmosphere at State Street bars to the romantic ambiance of the Olbrich Botanical Gardens, there are countless opportunities to meet sexy singles ready for some fun.

Imagine enjoying a drink at one of Madison's trendy breweries or attending a local music festival, all while being surrounded by potential hot contacts. Our platform makes it easy to find flirtatious conversations and spontaneous dates without the pressure of traditional dating apps. Whether you're looking for a casual fling or just some fun company, CasualMeetupz.com has got your back. Join now and start connecting with exciting people in the heart of Madison!

A selection of our members looking for casual hookups near Madison

Josiegurl69's profile picture

Josiegurl69, 47

Madison, Wisconsin, USA

I'm a tall CD TS woman. Love to be dressed sexy and be a gurl that enjoys to get with sexy TS or men. Willing to be rode and used.

I get wet when i am dressed slutty in feminine clothes with heels and nails done full make up with jewelry. I love to play with toys and have an anal plug keeping me wet. I'm happy when I am dolled up and getting rode hard like a sexy girl

Interests: Clubs, Parties & Socials, Lace, Underwear, Pantyhose, Cleavage Enhancement, Padding, Sissy, Roleplay, Discreet Meets, Hookups, Group Meets, Friends With Benefits, A Relationship, Friendship, BDSM, Lingerie, Drag Queen, Drag, Full Time, Transfan, Queer, Crossdress, Trans, Casual Dating, Transgender, Transexual, Anal, LGBTQIA+, Nylons, Open to Anything!

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shivand130's profile picture

shivand130, 43

Madison, Wisconsin, USA

Gaming part time father looking for the dessert after my dinner. 😉

Father of 3 part time. Just starting in cosplay for cons. I also collect and soon selling graded comics.

Interests: Adult Chat, Oral Sex, Roleplay, A Relationship, Fantasy, Cosplay, Console Gaming, Movies / Film, Comic Books

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LetsSeeWhatHappens12's profile picture

LetsSeeWhatHappens12, 55

Madison, Wisconsin, USA

Looking for a sexy female to join us from time to time.

We are a fun, down to earth couple. We work hard but enjoy our time off to relax or have fun. Love to have drinks in the summer hang out anywhere outside. We are busy at home & work but are making an effort to make time for us and enjoy this lifestyle. We are disease free and have been together for 22 years. No drama AT ALL please..

Interests: Oral Sex, Sex Toys, Sexual Massage, Full Swap, Threesomes, Couple fun, Erotic Fiction, FMF, Strip on webcam, Send naked pics, Video themselves, same room sex

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Lady Lovelee's profile picture

Lady Lovelee, 32

Madison, Wisconsin, USA

Baby Dom Ready to Please you i want to be in control

I'm 32 years old, living in the Madison region. I'm interested in meeting a man aged between 23 and 71. I'm Black / African

Interests: Bondage & Discipline, Roleplay, Spanking / Whipping, Dom, Friends With Benefits, Webcam, Online, Erotic Fiction, Beginner, Breast Play, Chasity, Wax Play, Findom

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Smiling Submissive's profile picture

Smiling Submissive, 59

Madison, Wisconsin, USA

I'm 59 years old, living in the Madison Wi

I'm 59 years old, living in the Madison Wi region. I'm interested in meeting a woman aged between 40 and 69.

Interests: Fisting, Dominatrix, Latex, Bondage & Discipline, Spanking / Whipping, Fetish, S&M, Sub, CBT, Medical Play, Dungeon Parties, A Relationship, BDSM, Foot Fetish, Breast Play, Chasity, Collaring, Electro-Play, Wax Play, gags

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Bhinz55's profile picture

Bhinz55, 52

Madison, Wisconsin, USA

I am a new want to be cuckold looking for a lady

45 single male looking for a bbw lady into cuckolding

Interests: Fetish, Sub, A Relationship

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Andy809's profile picture

Andy809, 40

Madison, Wisconsin, USA

Hey guys I’m Sonia looking for my soul mate

I'm looking for a man that I can love and cherished with all my whole being and heart and I pray to God almighty that he will provide me with that kind of a man someday in my life

Interests: Clubs, Parties & Socials, Sexual Massage, Sub, Exhibitionism, Hookups, Friends With Benefits, A Relationship, Online, Friendship, Couples, Mature, Casual Dating, Open to Anything!

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Fun Couple's profile picture

Fun Couple, 55

Madison, Wisconsin, USA

We are newcomers to this life style. Very fit professional couple looking for a discrete female unicorn (40 - 60, fit body type ) for friendship and more.

Hanging out, and talking. Socially drinking - especially with music, live music is the best. Gentle affection, spontaneous physical closeness. Looking for friendship first, then more -we are shy at first ...

Interests: Friends With Benefits, Friendship, Casual Dating

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FunRunner's profile picture

FunRunner, 40

Madison, Wisconsin, USA

I'm 40 years old, living in the Madison region.

I'm 40 years old, living in the Madison region. I'm interested in meeting a man aged between 48 and 93.

Interests: Sub

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jingleheimer99's profile picture

jingleheimer99, 58

Madison, Wisconsin, USA

Part time crossdresser seeking no strings

I'm interested in other CD's, trans or anybody else.

Interests: Lace, Pantyhose, Cleavage Enhancement, Female Masking, Sissy, Petticoating Roleplay, Roleplay, Exhibitionism, Discreet Meets, Hookups, Friends With Benefits, BDSM, Lingerie, Crossdress, Anal, Bondage, Nylons, Sex Talk

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Nakedfamous11's profile picture

Nakedfamous11, 42

Madison, Wisconsin, USA

Looking for unicorn. We would like to find someone who is close enough.

Very happy in life just looking for fun and someone to get to know.

Interests: Anal Sex, Social Events, Soft Swap, Full Swap, Threesomes, Discreet Meets, Hookups, Friends With Benefits, A Relationship, Friendship, Outdoor Fun, Casual Dating

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Keoki88's profile picture

Keoki88, 59

Madison, Wisconsin, USA

Laid back and easy going. Ready for som summer riding. Dont want anything serious just some sexual fun.

Getting out on my bike and seeing new things meeting new people. Family and friends

Interests: Sex Toys, Sexual Massage, Roleplay, S&M, MILF, Hookups, Friends With Benefits, Lingerie, Casual Dating, Anal, Bondage, Oral

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InspiringJester79d5c8's profile picture

InspiringJester79d5c8, 39

Madison, Wisconsin, USA

New, transitioning, and learning

I am transitioning MTF and am learning as I go. I’m happy to be a part of your happiness too.

Interests: Sex Toys, Roleplay, BDSM, Switch, Chasity

Join Casual Meetupz to message InspiringJester79d5c8

abriana's profile picture

abriana, 28

Madison, Wisconsin, USA

I'm 28 years old, living in the Tampa region.

I'm 28 years old, living in the Tampa region. I'm interested in meeting a man aged between 28 and 90.

Interests: Masturbation, Sex Toys, Group Sex, Clubs, Parties & Socials, Sexual Massage, Lace, Threesomes, Cuckold, Roleplay, Fetish, Dom, Sub, BBW / BHM, Discreet Meets, MILF, Hookups, BDSM, Outdoor Fun, Erotic Fiction, Lingerie, Crossdress, Casual Dating, Pegging, Anal, ASMR, Body Hair, Bondage, Curves, Dirty Talk, Edging, Electro Play, Feet, Impact Play, Leather / Latex, LGBTQIA+, Nylons, Oral, Petite, Sex Games, Tickle Play

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Fukmerghtnow's profile picture

Fukmerghtnow, 43

Madison, Wisconsin, USA

I want to meet up and have some hot sex!

I'm clean handsome and want to be adventurous come see what you can get into with me!

Interests: Sex Toys, Sexual Massage, Lace, MILF, Hookups, Outdoor Fun, Lingerie, Mature, Curves

Join Casual Meetupz to message Fukmerghtnow

Bryan's profile picture

Bryan, 30

Madison, Wisconsin, USA

We are couples married 10 years, looking for fun!

Full swap, soft swap, single woman who wants to have fun.

Interests: Social Events, Clubs, Parties & Socials, Soft Swap, Full Swap, Parties, Threesomes, Cuckold, Hookups, Group Meets, Friends With Benefits, Couples, Swinging

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EagerJetsetter's profile picture

EagerJetsetter, 34

Madison, Wisconsin, USA

Available 24/7 for love

I'm 34 years old, living in the Madison region. I'm interested in meeting a man aged between 25 and 62. Would really love us to get more communication with each other. I promise to respond back to all messages.

Interests: Sex Toys, Latex, Bondage & Discipline, Spanking / Whipping, S&M, Dom, Sub, CBT, Medical Play, Dungeon Parties, BDSM, Erotic Fiction, Foot Fetish, Switch, Trampling, Pony Play, Breast Play, Chasity, Contract, gags, suspenders

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Kinkycouple69's profile picture

Kinkycouple69, 45

Madison, Wisconsin, USA

Kinky pair who would like to add a female player to our kinky adventures!

Mid 40s pair living in the Madison region. interested in meeting a woman aged between 27 and 70 to add to our adventures. Prefer a female who can take the reigns and handle female in front of male player.

Interests: Clubs, Parties & Socials, Clubs, Parties, Threesomes, Cuckold, Hookups, Friends With Benefits, Friendship, BDSM, Outdoor Fun, Open to Anything!

Join Casual Meetupz to message Kinkycouple69

Cecil's profile picture

Cecil, 54

Madison, Wisconsin, USA

Experienced master, mentor for the curious, less experienced. I believe in safe, sane consensual in all my dealings with newbies/rookies .

I’m a strict Master yet who thrives on guiding willing submissives into their full potential through discipline, trust and play.

Interests: Sex Toys, Latex, Cuckold, Roleplay, Spanking / Whipping, Dom, CBT, BDSM, Chasity, Collaring, Contract, gags, Pegging

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 Josiegurl 's profile picture

Josiegurl , 47

Madison, Wisconsin, USA

I'm tall sexy crossdresser. I'm working on transitioning to a transgender woman. I love to dress up like a sexy woman and have fun. Love to be a woman. Dresses heels makeup nails jewelry hair done to be sexy.

Being a transgender woman makes me feel so beautiful. Love toys and pleasing my lover every day.

Interests: Clubs, Parties & Socials, Lace, Underwear, Pantyhose, Cleavage Enhancement, Female Masking, Sissy, Discreet Meets, Hookups, Group Meets, Friends With Benefits, A Relationship, Friendship, Lingerie, Part Time, Drag Queen, Drag, Full Time, Transfan, Queer, Crossdress, Trans, Casual Dating, Transgender, Transexual, Intersexual, Intergender, Leather / Latex, Open to Anything!

Join Casual Meetupz to message Josiegurl

Related Locations near USA, Wisconsin

Hookup in other towns near Madison such as Middleton , Janesville , Wisconsin Dells , Rockford , Loves Park , Elm Grove , Butler , Greendale , Milwaukee , Sturtevant today!

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