Eastern Shore, Maryland Alternative Sex Ads - BDSM, Trans & Swingers

Browse Eastern Shore, Maryland 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!

Home / Alternative Sex Ads /

Show Ads In: Annapolis | Baltimore | Eastern Shore | MD suburbs of DC | Southern MD | Western MD

November 18th, 2025

Naughty Shemale Looking for Hot Fun in Eastern Shore Are you a horny guy looking for a wild time with a sexy shemale? Look no further, because I'm Naoma and I'm ready to rock your world! I'm a kinky shemale from Eastern Shore, Maryland, seeking a local man for some steamy encounters. I love all kinds of naughty fun, from giving sloppy blowjobs to ...

Explore Your Wildest Desires with Eddi from Eastern Shore Hey there! I'm Eddi, a girl from Eastern Shore who has a unique fetish that I absolutely love. I won't reveal what it is just yet, but trust me, it's something you've never experienced before. I'm friendly, open-minded, and always up for exploring new kinks and fetishes. One thing that really int...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Ash, a submissive male from Eastern Shore, Maryland, looking for a Dominant Female Mistress or Dominatrix to force me into submission and teach me how to please a Mistress properly. I enjoy whippings, domination, roleplay, spankings, age play, crossdressing, and humiliation. I am eager to expl...

Passionate Swingers Seeking Playmates on Eastern Shore, Maryland Hey there, I'm Jenn from the beautiful Eastern Shore of Maryland. My husband and I are fun-loving, open-minded, and kink friendly swingers looking to spice things up in the bedroom. We enjoy exploring our deepest desires and fantasies with like-minded individuals who share our passion for the life...

Looking for Love and Adventure on the Eastern Shore! Hey there! My name is Alyce, and I'm a transgender woman living in beautiful Eastern Shore, Maryland. 💖 I may not fit society's typical mold, but that's what makes me unique! I have a body that tells my own story, one of strength and resilience. Being transgender has taught me to embrace my tr...

Unleash Your Desires with Kenn from Eastern Shore, Maryland! Hey there! My name is Kenn, and I have a unique fetish that I absolutely adore. 🌟 As a submissive male, I find immense pleasure in exploring the world of domination with a strong and confident woman. It's like diving into an ocean of thrilling sensations! What do I love about my fetish? Well, ...

Passionate Swingers Seeking Playmates on Eastern Shore Hey there, I'm Mechelle from Eastern Shore, Maryland. 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 fantasies and indulging in our wildest desires. 💋 If you're looking for a couple who knows how to have...

Elegantly Transcendent Charisse Seeks Connection Hey there! I'm Charisse, a transgender beauty from Eastern Shore, Maryland. I may not fit society's mold, but that's what makes me unique and fabulous. 💃 I love exploring my city and checking out local spots like the Chesapeake Bay Maritime Museum or grabbing a bite at the Fisherman's Inn. �...

Kinky Mistress Seeking Submissives for BDSM Fun I've always been drawn to the world of kink and fetish, exploring different aspects of domination and submission. My name is Karol, and I'm a dominant woman from Eastern Shore, Maryland who loves to take control in the bedroom. I enjoy a wide range of kinks, from whippings to roleplay to age pla...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Gregor from Eastern Shore, Maryland, and I'm a submissive male looking for a Dominant Female Mistress or Dominatrix to take control and force me into submission. I want to learn how to please a Mistress properly and explore all kinds of kinky fetishes and roleplay scenarios. I enjoy being spa...

Explore Your Wildest Desires with Zeke from Eastern Shore Hey there, I'm Zeke from Eastern Shore, Maryland. I have a unique fetish that I absolutely love - I am into role-playing as a naughty schoolboy. There's something about being submissive and letting go of control that really excites me. I'm looking for a Dominant woman who can take charge and show ...

Passionate Swingers Seeking Playmates in Eastern Shore, Maryland Hello there, I'm Anetta from Eastern Shore, Maryland. 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 adventures and sharing our passion with like-minded individuals who are not afraid to let loose and have a...

Naughty Shemale Looking for Hot Fun in Eastern Shore, Maryland I'm a horny shemale named Enya looking for a local man to have some wild fun with. I love getting down and dirty, and I want to explore all of your deepest fantasies. I'm a top who loves to dominate and take control, but I also enjoy being a submissive bottom if that's what you're into. Whether yo...

A Sensual Journey of Self-Discovery Hey there, I'm Minna from Eastern Shore, Maryland. As a transgender woman, I embrace my journey of self-discovery and love every moment of it. I find beauty in authenticity and courage in vulnerability. I enjoy exploring new places and trying out different cuisines. How about we meet up for a co...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Eastern Shore I will help you unwind and create a cozy environment for you! I am 36DD, 7" and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl Gayle <3    Transgender World Profile Username: Ga...

Unleash Your Wildest Desires with Trish from Eastern Shore, Maryland! Hey there, fellow thrill-seekers! I'm Trish, a vivacious female swinger hailing from the mesmerizing Eastern Shore of Maryland. Together with my amazing husband, we're here to take you on an unforgettable journey into the world of pleasure and exploration. Open-mindedness is our middle name! We b...

Swinging Couple in Eastern Shore, New to the Lifestyle Swinging Couple in Eastern Shore We are a swinging couple in Eastern Shore, Maryland. 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...

Passionate Swingers Seeking Playmates on the Eastern Shore Hello there, I'm Rosalind from Eastern Shore, Maryland. My husband and I are fun-loving, open-minded, and kink friendly swingers looking to connect with like-minded individuals for some adult fun. We believe in exploring our desires and embracing our sexuality to the fullest. You can find us in t...

HMU for Sex in Eastern Shore Newly Single and Ready to Mingle in Eastern Shore Hi guys, my name is Barbie, age 28. My husband cheated for the last time. Now it's my time to have some fun! If you want to hook up for passion and hot sex in the Eastern Shore, Maryland area then message me @BarbieSingle28.     &nb...

Passionate Swingers Looking to Play Hello there, I'm Clarette from Eastern Shore, Maryland. My husband and I are fun-loving, open-minded, and kink friendly swingers who are always up for a good time. We believe in exploring our desires and living life to the fullest. You can find us on FreeSexAds.com Swingers Lifestyle Profiles unde...

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

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Eastern Shore 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 Me...

MISTRESS KIM IS HERE TO DOMINATE YOU.... Seeking new worthy, generous submissive Mistress Kim Eastern Shore Dominatrix Message Me Online: MistressKim4subEastern Shore Flogging...prostate...nipple play...force by... paddling...dress up play..humiliate... strap on...must obedience......

Kinky Fetish Fun with Calypso from Eastern Shore, Maryland Hey there! My name is Calypso and I'm a naughty little vixen from the Eastern Shore of Maryland. I have some wild kinks and fetishes that I love exploring, and I'm always looking to try new things. You can find me on FreeSexAds.com Alt profiles under username calypsoeas66704. I absolutely adore B...

Seeking Connection in Eastern Shore Hey there, I'm Scarlet from Eastern Shore, Maryland. I'm a curvy and confident transgender woman who loves exploring my LGBTQ identity. I find joy in embracing my true self and connecting with others who appreciate authenticity. Whether it's a cozy coffee date at Rise Up Coffee Roasters or a sceni...

Tempting Adventures Await with Noreen from Eastern Shore, Maryland! Hey there, fellow thrill-seekers! I'm Noreen, and together with my amazing husband, we're on a journey to explore the depths of pleasure and push boundaries like never before. If you're ready to embark on an unforgettable adventure into the world of swinging, then look no further! We hail from th...

Kinky Mistress Seeking Submissives for BDSM Fun I'm Kirstyn from Eastern Shore, Maryland, and I'm on the hunt for some naughty playmates who share my love for all things kinky. Whether you're into whippings, domination, submission, roleplay, spankings, age play, crossdressing, or humiliation, I'm your girl. I thrive on exploring new fetishes an...

Kinky Fetish Fun with Acacia from Eastern Shore, Maryland I'm Acacia and I'm all about exploring kinky fetishes and pushing boundaries. I love indulging in BDSM play, especially as a Dominatrix taking control of my submissives. Whippings, domination, submission - you name it, I enjoy it all. But I'm also open to trying new things like roleplay, age play...

Passionate Swingers Looking for Playmates Hello there, I'm Terra from Eastern Shore, Maryland. My husband and I are fun-loving, open-minded, and kink friendly. We are always up for new adventures in the swinging lifestyle. You can find us in the FreeSexAds.com Swingers Lifestyle Profiles under username terraeas11779. We love to indulge i...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Benjamen, a submissive male from Eastern Shore, Maryland. I'm on the hunt for a Dominant Female Mistress or Dominatrix who can force me into submission and teach me how to properly please a Mistress. You can find me in the Alt profiles under username benjamene49652. I have a variety of submis...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Paulo, a submissive male from Eastern Shore, Maryland, seeking 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 pauloea25461. I enjoy various kinky fetishes such as...

Looking for Love and Adventure on the Eastern Shore! Hey there, lovely people of Maryland! 💖 My name is Petra, and I'm a transgender woman living on the beautiful Eastern Shore. I wanted to put myself out there and see if I can find that special connection with someone who appreciates me for who I am. So here goes! I'm a free-spirited soul who e...

Gorgeous, Passable Trans in Eastern Shore 😍 Gorgeous Passable Trans MtF for Man in Eastern Shore 😍 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!  ...

Mistress seeks Eastern Shore male sub for BDSM and training Mistress seeking male sub in Eastern Shore I am Mistress Velvet Sky. I use a variety of toys on My boys. You will be My submissive boy toy. I have a contract that We/we will mutually agree to in writing. We/we can hash this out if we decide to enter a Dom/sub relationship. I am not a game player, s...

Unleash Your Desires with Carlton from Eastern Shore Hey there, I'm Carlton and I have a unique fetish that I just can't get enough of. I love being tickled until I can't take it anymore! It's such a thrilling sensation that drives me wild. I'm a submissive guy who would love to meet a Dominant woman who can indulge my desires. I'm friendly, open-m...

Unleash Your Wildest Desires with Kassie from Eastern Shore! Hey there, fellow adventurers! My name is Kassie, and I'm here to invite you on a tantalizing journey through pleasure and passion. Together with my amazing hubby, we're ready to explore the thrilling world of swinging in Eastern Shore, Maryland. Now, let me paint a picture for you. Picture a wom...

Want to Fuck My Wife? Let's Swap in Eastern Shore Wife Swaps in Eastern Shore Attractive, adventurous and athletic couple in the Eastern Shore area seeks swinger hookups for social activities and the explore the local swinging lifestyle. He is Thomas, age 29, a self-employed graphic artist. Fit and trim, loves sex!  She is Heather, age 27, ...

Kinky Fetish Fun with Enya from Eastern Shore, Maryland I never thought I'd be the type to explore my deepest desires, but here I am, ready to dive into the world of fetish and kink. My name is Enya, and I'm looking for someone who can match my adventurous spirit. From BDSM to roleplay, I'm open to trying new things and pushing boundaries. I enjoy be...

SHEMALE HOOKUPS! Wanna Have a Great Time in Eastern Shore, Maryland? HOT!  SHEMALE HOOKUPS  "The girl with a naughty little secret in her panties!" SIGNUP FREE: INSTANT ACCESS!  Shemale Profiles Browse Uncensored Photos, Swap Your Pics, Join Live Web Cams, Swap Private Messages, Sext & Hook Up! Join free for Instant Access to the East...

Spark a Connection with Renee from Eastern Shore Hey there! I'm Renee, a fun-loving transgender woman from the Eastern Shore area of Maryland. I may not fit society's typical mold, but that's what makes me unique and special. I embrace my LGBTQ identity and love connecting with others who appreciate authenticity. I enjoy exploring new places li...

Explore Kinks and Fetishes with Libbi from Eastern Shore Hey there, I'm Libbi from Eastern Shore, Maryland. My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. We believe in creating a safe and respectful space for everyone to indulge in their deepest desires. Whether you're new to the lifestyle o...

Explore Kinks and Fetishes with Marlene from Eastern Shore Hello there! My name is Marlene, and I am a female swinger from Eastern Shore, Maryland. My husband and I are friendly, open-minded individuals who love to explore all kinds of kinks and fetishes. We believe in creating a safe and comfortable space for like-minded individuals to come together and ...

Passionate Swingers Seeking Playmates Hello there, I'm Maurene from Eastern Shore, Maryland. My husband and I are fun-loving, open-minded, and kink friendly. We are always looking to spice things up in the bedroom and explore new adventures with like-minded individuals. You can find us in the FreeSexAds.com Swingers Lifestyle Profile...

Passionate Swingers Seeking Playmates in Eastern Shore, Maryland Hello there, I'm Ronda from the Eastern Shore of Maryland, and my husband and I are on the hunt for some naughty fun with like-minded individuals. We are a fun-loving couple who enjoy exploring our wild side in the swingers lifestyle. We are open-minded, kink-friendly, and always up for new adve...

Debonair Trans dude, looks like Bond F2M Trans Dude in Eastern Shore Looking for someone a little different from the average guy? Hey, I'm Barry, age 31, fit and healthy. I have a square jaw, sparkling eyes and short dark hair. I like to dress sharp. I am currently looking for a fun lady to spend time with. Possible longterm relations...

Passion Seekers in Eastern Shore, Maryland Hello there, I'm Regine from the beautiful Eastern Shore of Maryland. My husband and I are a fun-loving, open-minded couple who enjoy exploring our kinks and fantasies with like-minded individuals. We are active members of the swinging lifestyle community and always looking for new friends to join...

Mistress Savannah in Eastern Shore // Domme seeking new sub Strict Mistress for sub in Eastern Shore 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 ...

Explore Kinks and Fetishes with Remy from Eastern Shore Hey there, I'm Remy from Eastern Shore, Maryland. My husband and I are friendly, open-minded swingers who love to explore all kinds of kinks and fetishes. We believe in creating a safe and welcoming space for like-minded individuals to come together and indulge in their deepest desires. You can f...

Exploring Love and Adventure as a Transgender on the Eastern Shore Hey there! My name is Britni, and I'm thrilled to be putting myself out there in the dating world. 💕 As a transgender woman living on the beautiful Eastern Shore of Maryland, I'm excited to meet someone special who appreciates me for who I am. Being trans has taught me so much about self-accep...

Well Endowed Shemale for Man in Eastern Shore Hung Shemale for Man in Eastern Shore 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 u...