Casual Hookups in Boston: Meet Hot Contacts for Fun!

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Welcome to CasualMeetupz.com, your premier destination for casual hookups in the vibrant city of Boston, Massachusetts. Whether you're exploring the lively streets of Beacon Hill or soaking up the sun along the Charles River, meeting new people for sexy fun has never been easier. Our site connects you with attractive singles who are ready for spontaneous adventures. Forget Tinder and dive into a world where flirting and excitement await you at every corner!

Boston is not just rich in history but is also a hub for socializing and connecting. Picture yourself enjoying a drink at a trendy bar in the Seaport District or taking a stroll through the Boston Common. With so many lively venues, you'll find the perfect spot to meet hot contacts who share your desire for casual encounters. Don't wait any longer; explore your options today and make unforgettable connections with like-minded individuals right here in Boston!

A selection of our members looking for casual hookups near Boston

Top2Bottom2's profile picture

Top2Bottom2, 55

Boston, Massachusetts, USA

Looking forward like minded to play DRESS-UP and play, top & bottom IDEALLY, long dress-sex sessions, body worshipping after dressing, small to mid- size penis or straps, like nighty/negligee types also sharp dressers, must be bald , love weekendbest

As you seen, I enjoy sex but also, if passable, as a man, I also enjoy dating, going out, enjoying life, staying in and snuggling, watching a movie, I LOVE DRESSING UP AND COOKING YOU A MEAL OR CLEANING YOUR HOUSE WHILE YOU LUST ME, BIG ON THAT, I LOVE TOP AND BOTTOM BUT IF YOU JUST NEED A MAN, I CAN DO THAT TO. IF THATS ALL YOU WANT, IT WILL BE HARD BUT I WILL TRY MY BEST TO ACCOMMODATE ALL YOUR FANTASIES. I AM FLEXIBLE AND IF YOU HAVE VERY PASSABLE FRIENDS AND JUST WANT ME DRESSED SO YOU GURLS CAN ALL HAVE ME AT ONCE, CUM ON! FILL ALL MY HOLES, YOU MUST HAVE CLOTHES FOR ME AS I CANNOT KEEP ANY WHERE I LIVE. ONLY VERY FEMININANT NEED APPLY, NOT INTO MEN OR BODY HAIR OF ANY KIND EXCEPT WIGS OR NATURAL FEMININE HAIRSTYLE. SORRY! IF YOU ARE PASSABLE, I ALSO ENJOY FISHING, CAMPING, LONG ROMANTIC WALKS, KISSING, HOLDING HANDS, SOME OUTDOOR PLAY, I. EXTREMELY ENJOY VERY BEAUTIFUL CDS THAT CAN DRESS CASUALLY SEXY, LIKE TIGHT JEANS AND HIGH HEEL TYPES, I ENJOY CLUBS , TS, TV, nightclubs, okay

Interests: Clubs, Parties & Socials, Latex, Lace, Satin, Pantyhose, Cleavage Enhancement, Sissy, Petticoating Roleplay, Roleplay, Exhibitionism, Discreet Meets, Hookups, Group Meets, Friends With Benefits, A Relationship, Friendship, BDSM, Lingerie, Part Time, Admirer, en Femme, Full Time, Stealth, Transfan, Crossdress, Trans, Casual Dating, Anal, Bondage, Leather / Latex, LGBTQIA+, Nylons, Open to Anything!

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EngagingVolunteeribhcjj's profile picture

EngagingVolunteeribhcjj, 23

Boston, Massachusetts, USA

I am a dominant mistress looking for a submissive person to explore into Bdsm lifestyle

I am a Dominant mistress looking for a serious, submissive and committed to serve me adore me and treat me as his goddess

Interests: Sex Toys, Fisting, Latex, Cuckold, Bondage & Discipline, Roleplay, Spanking / Whipping, Fetish, S&M, Dom, CBT, Medical Play, Dungeon Parties, BDSM, Erotic Fiction, Foot Fetish, Trampling, Pony Play, Breast Play, Chasity, Collaring, Contract, Electro-Play, Wax Play, gags, suspenders, Pegging, Findom

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CoupleLookin4third's profile picture

CoupleLookin4third, 48

Boston, Massachusetts, USA

Fun Loving ENM Couple Seeking a Fun Loving Female

Husband (48- straight) and wife (50- bi). We love having great conversations with a nice glass of wine in our hands.

Interests: Hookups, Friends With Benefits, Outdoor Fun

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FriendlyChef27f9bd's profile picture

FriendlyChef27f9bd, 58

Boston, Massachusetts, USA

I'm going to please you whenever you want

I'm 57 easy going but again eat p**** is very good

Interests: Sex Toys, Fetish, S&M, Contract

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AdamEve's profile picture

AdamEve, 35

Boston, Massachusetts, USA

Married couple looking for one girl who wants to explore a fun experience together

we love to cook for each other and going out to eat any chance we have we like to dance and just have fun and not take life too seriously we like adrenaline and have both gone sky diving together we just want to have a fun night

Interests: Anal Sex, Sex Toys, Threesomes, FMF

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prestonmicl2001's profile picture

prestonmicl2001, 56

Boston, Massachusetts, USA

I'm 52 years old, living in the Boston region. I'm interested in meeting a woman aged between 30 and 59.

I'm 52 years old, living in the Boston region. I'm interested in meeting a woman aged between 30 and 59. Preston is my first name Michael is the second the year is 2001 and my favorite drink has always been chocolate milk which is a website also Hope your good at doing puzzles because I would love to hear from you. Oh and I’m 6ft tall with average body shape. I drink socially I don't smoke

Interests: Threesomes, Discreet Meets, MILF, Lingerie, Mature

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tsjessy's profile picture

tsjessy, 34

Boston, Massachusetts, USA

Your fav trans girl Based in boston massachusetts

A honest girl and trustworthy Likes to travel Content creator

Interests: Sex Toys, Hookups

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EllaKimberly's profile picture

EllaKimberly, 38

Boston, Massachusetts, USA

Skilled and experienced dom seeking a long term relationship with one loyal and obedient man.

I will bring out the best in my partner, help him find himself, his self esteem and his own satisfaction and pleasure.

Interests: Sex Toys, Latex, Cuckold, Bondage & Discipline, Roleplay, Spanking / Whipping, Fetish, S&M, Dom, CBT, Medical Play, Dungeon Parties, BDSM, Erotic Fiction, Trampling, Chasity, Collaring, Pegging

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ElegantHeartthrobicaehc's profile picture

ElegantHeartthrobicaehc, 36

Boston, Massachusetts, USA

im a gentle warm hearted person by nature, fun and very accommodating with transparency. you'll always cherish every moment we spend together .

honest caring, communication and funny gist,no play no game.

Interests: Sex Toys, Voyeurism, Sexual Massage, Lace, Threesomes, Cuckold, Roleplay, Fetish, BBW / BHM, Discreet Meets, Webcam, BDSM, Outdoor Fun, Erotic Fiction, Lingerie, en Femme, Full Time, Dairy Queen, en Homme, M2F, TS-Friendly, Pegging, Anal, Leather / Latex, LGBTQIA+, Oral

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Aleya's profile picture

Aleya, 28

Boston, Massachusetts, USA

Mixed asian/American looking for fun

Generous gifts that will make me submit and happy to do whatever he wants

Interests: Sex Toys, Roleplay, Fetish, Sub, BDSM

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Honeymoon's profile picture

Honeymoon, 51

Boston, Massachusetts, USA

Awesome fun couple looking to add to the fun with the right girl

Both divorced recently and enjoying fun relationship. Happy and mature looking for discretion and a blast.

Interests: Clubs, Parties & Socials, Threesomes, Hookups, Friends With Benefits, Swinging, Open to Anything!

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SpiritualBeautycaajhb's profile picture

SpiritualBeautycaajhb, 58

Boston, Massachusetts, USA

Just looking for anything within the local area

I'm 58 years old, living in the Boston region. I'm interested in meeting a woman aged between 31 and 69.

Interests: Sex Toys, Hookups, A Relationship, Mature, Anal, Curves, Oral, Petite, Sex Games, Sex Talk

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Luisa 's profile picture

Luisa , 25

Boston, Massachusetts, USA

Playing it and living it, is all part of the lifestyle and I enjoy it

. "Exploring the world through my lens" . "Sharing smiles and adventures" . "Capturing moments that matter" . "Embracing the beauty of everyday life"

Interests: Sex Toys, Fisting, Latex, Cuckold, Bondage & Discipline, Roleplay, Spanking / Whipping, Fetish, S&M, Dom, CBT, Medical Play, Dungeon Parties, BDSM, Erotic Fiction, Foot Fetish, Trampling, Pony Play, Breast Play, Chasity, Collaring, Contract, Electro-Play, Wax Play, gags, suspenders, Pegging, Findom

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ExcitingListener6b967's profile picture

ExcitingListener6b967, 59

Boston, Massachusetts, USA

Dominance rooted in trust, control shaped by connection

I’m a calm, confident Dom. Control comes naturally, but respect is always first. I believe in structure, trust, and deep connection. I lead with intention, not ego. Soft when needed, firm when it counts. Not here to rush only to build something real

Interests: Dom, Hookups, A Relationship, BDSM

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RyNicoXXX's profile picture

RyNicoXXX, 35

Boston, Massachusetts, USA

"Couple man/women " looking for a sexy woman to join us

Husband and wife looking for a beautiful women to enjoy together. While we aren't looking to add a partner to our relationship romantically, we'd ideally like to find a sexy, funny, beautiful women to meet up with regularly. Communication and boundaries are key and not only is it important for ours to be respected but yours as well. Nico (wife) is Bi and lovess women Ry (Husband ) is straight. Looking to for a gorgeous women to spoil in the bedroom together. Hope to hear from you soon

Interests: Oral Sex, Anal Sex, Sex Toys, Threesomes, Hookups, Friends With Benefits, Casual Dating

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Luvly77's profile picture

Luvly77, 45

Boston, Massachusetts, USA

Good Evening.. I’m new to this site I would like to have fun

I'm 44 years old, living in the Kansas City region. I'm interested in meeting a man aged between 46 and 90.

Interests: Sex Toys, Fisting, Latex, Bondage & Discipline, Roleplay, Spanking / Whipping, Fetish, S&M, Dom, Medical Play, Dungeon Parties, Erotic Fiction, Foot Fetish, Breast Play, Collaring, Contract, Wax Play, suspenders, Findom

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Snoopy's profile picture

Snoopy, 20

Boston, Massachusetts, USA

My gf and I are looking for a 🦄 to have some fun with

I like all shapes and sizes I’m not really sure what to put here

Interests: Hookups, Friends With Benefits

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DynamicCreator93's profile picture

DynamicCreator93, 35

Boston, Massachusetts, USA

Let’s Netflix and Chill :-) ..

I’m not big talking about myself but just get to know me and I’ll get to know you.

Interests: Clubs, Parties & Socials, Threesomes, MILF, Friends With Benefits, Friendship, Casual Dating, Petite, Open to Anything!

Join Casual Meetupz to message DynamicCreator93

Katerina's profile picture

Katerina, 32

Boston, Massachusetts, USA

Hey, I'm down to meet up!

To me, a man is described by his actions, not his words.

Interests: Masturbation, Hookups, Erotic Fiction, Anal, Feet, Sex Talk

Join Casual Meetupz to message Katerina

FlirtyRunnergirl's profile picture

FlirtyRunnergirl, 37

Boston, Massachusetts, USA

My Expertise Shapes the Future. As a renowned expert, I leverage my knowledge to drive progress. My insights illuminate new pathways, and my strategic guidance enables organizations to seize opportunities.

Fueling Growth, being responsible and ensuring responsibility

Interests: Fisting, Roleplay, Fetish, S&M, Dom, CBT, BDSM, Erotic Fiction, Foot Fetish, Chasity, Contract, suspenders, Pegging, Findom

Join Casual Meetupz to message FlirtyRunnergirl

Related Locations near USA, Massachusetts

Hookup in other towns near Boston such as North Waltham , East Boston , Jamaica Plain , Mattapan , Lynn , Hanscom Afb , Brockton , Lowell , Bridgewater , Nashua today!

Looking for something a bit different?

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Trans and crossdressing fun in Boston at Red Hot Trans

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