Annapolis, Maryland Sex Ads and Adult Classifieds

Annapolis, Maryland 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: Annapolis | Baltimore | Eastern Shore | MD suburbs of DC | Southern MD | Western MD

  • September 2nd, 2026
  • Not exactly out yet. Need discreet NSA... Mixed mexican/white male 29yrs, professional divorced with two kids. I am looking to explore my bi-sexual curiousity in the Annapolis area with the right man and see if there is anything there. If you can be discreet and are interested then please come see me by clicking here....
  • 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...
  • EXPLORE YOUR KINKS WITH THE STRAP-ON QUEEN!!! Annapolis Boys Deeply Love My Strap On Fetish Your gonna meet BigBen my favorite strap on! (shown in the pic attached) I'm Sandra a bi-sexual fetish friendly hot bitch who definitely wants to do it freaky and rough to men, women and couples in Annapolis tonight. I specialize in strap on, pegging, B...
  • INSTANT BANG BUDDIES - Free - Anonymous - Verified Pics INSTANT BANG BUDDIES! Get Your Freak On with Local Bang Buddies   Local Pics / Upload Your Pics SPECIAL: JOIN FREE FOR INSTANT ACCESS! Upload Your Hot Pics Browse Local Hotties Hookup with local bang buddies Signup Free Instant Access! How Many Bang Buddies Are Available In...
  • Widower seeking affection in Annapolis Annapolis Widower Seeking Affection Hello ladies, my name is Jonathan and I am seeking some female company for fun times and affectionate days. It has been a while and I have to face that I'm lonely. I am 52 and still look in my late thirties (I am told) and I am fit and healthy. I love riding hors...
  • Attractive, Dark haired and Slender - Brunette28XAnnapolis Hi, thanks for checking out my classified! I am tall, slender with dark hair and deep brown eyes. My interests include running, hiking, biking and horse riding. I am an account manager and I have just moved here. I am looking for local friends with a view to dating and possibly more. I will add mor...
  • Shania Needs Some Sexy Masculine Energy in Annapolis! Want a Real Man in Annapolis! Shania here and I'm looking for a certain type of energy to make me feel like a woman. I'm old school in many ways and love to be feminine and treated like a lady. But I'm a lady with needs like anyother and only you can satisfy those needs.  I live here in Annap...
  • George, 31, long beard to tickle you with Bearded Man for Non-Bearded Lady in Annapolis Hey ladies, I am George and I am 31. I have been growing my beard for 3 years and it is nice and long. If you like bearded dude let me know and send me a private message @BeardedGeorge. I'm fun loving, athletic, Alpha type guy, comfortable in my skin, a...
  • BBW - Itchy, Twitchy and Getting Kinda Bitchy in Annapolis Single Female w an Itch in Annapolis Juanita here in Annapolis looking for a man to scratch my itch. You scratch mine and I'll scratch yours kinda deal. Not talking about a full-blown relationship, but more of a friendly-friend to come to my rescue when it gets urgent. (know what I mean? πŸ˜‰) I'm ...
  • European Lady seeks sensual gentleman European Lady in Annapolis My name is Karena and would like to meet a kind gentleman for dinner and dating. I am mature and I originate from Europe and moved here recently. Serious callers only and I am willing to please you.  Check my website pics and contact info KarenaXX86...
  • I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Annapolis I'm queen Delilah a trans woman here in Annapolis searching for her king. You'll get the royal treatment when you're with me honey! Just grab hold of my magic scepter and his majesty can have anything he desires. Imagine the intrigue and scandalous posi...
  • I Need a Body Rub Followed by a Naughty Rub! Hey gents I'm Lauren, 24, hard worker, large boobs, brown hair, blue eyes and 5'5, and I want a full body massage if you live in the Annapolis area. About me: Sucker for a good long massage, a major turn on! About you: sensual stong hands, stamina, know the female anatomy and be a quick learner of t...
  • Mature sexy nurse seeking to share fun times with Handsome fella Mature Nurse Seeks Fun Times in Annapolis I am a nurse and work long hours but I need to relax and spend time with a sexy, fun playmate. I am looking for a guy who is available to date and has patience and is kind. SeXXXyNurse See my profile and send a PM. Any race Any age (18+) Clean and...
  • Catch Me if You Can Butches! Yo, all you Annapolis butches! U looking for some hot chocolate tonight? I am Lola a black fem lesbian and just love me some confident, assertive sexy butches who know how to treat a woman in and out of the bedroom. Please be between say 20 and 40 years old and live in the Annapolis area. Contact me...
  • DoobieSisters Looking for Smoke Buds... DoobieSisters we are hot, sexy and are here seeking generous gentlemen with weed for girls in need. You won't need anyone else to smoke your blunt from now on ;) Come check out our new improved Annapolis profile and lets cut out the middleman if you know what we mean! Click here to introduce yoursel...
  • Quirky Fun Loving Lesbian Couple in Annapolis... Lesbian Couple Seeks Equal Partner Hi out there in Annapolis we are Tori and Joni a lesbian couple looking for a third to join us for some sexy fun and antics. This is a proposal for a long term relationship with an open minded couple who can't resist the idea of bringing in another woman for extra...
  • I'm a Steamroller Baby! Hi ladies, James here nice to meet you! Let's hop on my bike, put our knees to the breeze and do whatever the hell we please! I'm good with my hands, still a bit of an outlaw at heart, 35 years old, lived here most of my life, blonde hair, blue eyes, 6'1, around 220 pounds, muscular, love women, hug...
  • Chubby Chick looking for guy who can handle me! So, I am a little heavy but more just curvy. I have 44DD boobs and I love, love, love to laugh! You gotta be funny if you are going to date me. Why not text me your favorite joke and we can see how we get along!  Lisa44DDAnnapolis...
  • Angelic and single with big tits that love attention! Hi guys, my name is Trisha and I am 24 and wanting to meet a cool guy who likes live music and hiking. My breasts are one of my best features so I hope you like them! I'm pretty cute to look at too. You must have a good sense of fun and be intelligent and responsible. My measurements are 38-26-36! ...
  • Smoke and Leather! Smoke and leather go together. I'm Toby, 32yrs, 6'0, 200 pounds, extra large, living in the Annapolis area, a hairy thug, def top gay man wanting to pound gay, bisexual and bi-curious men. Just be ready to pleasure me while I chain smoke. I don't care if you smoke or not just be damned grateful that...
  • Macho, Macho Man... Are you one of the Village People? I'm a 40 year old macho man looking for bottom man in Annapolis. Be ready to be rode hard and deep. I'm 6'2, muscular, hairy, blue eyes, black hair, full 8in, and full of fire. I'm gonna make you tap out boy! I'll pick you up on my Harley and take you for a ride yo...
  • Tiffany Shelle - Your Annapolis Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Annapolis It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGIT βœ¨πŸ’ž SKILLED, Exotic and Erotic πŸ’¦ πŸ₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% function...
  • Needed: Single Men and Women For Sexy Swinger Couples in Annapolis!... Meet Local Swingers and Get Naughty! Thanks to you Annapolis swingers can spice things up by having a sexy woman, a hot man or even an amazing couple join them in the bedroom for adult fun. Instant Access - Biggest  Selection - Widest Variety Meet and hookup for the best sex ever!...
  • Swingers Seek Sexy Man or Woman for Menage a Trois in Annapolis How About a Threesome in Annapolis? Funloving couple in Annapolis would love to meet open minded men and women for casual hookup. We are Dana (26 years old) and Rita (25 years old) and have just about one year in the swinger lifestyle and are having a blast. We have tried wife swapping and foursome...
  • Daniel 28, Plumber, recently new to area 28 y/o Man New to the Annapolis Area For Dating I am fairly a plumber by trade. I am looking for new people to meet in the Annapolis 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 campin...
  • Asian Lilly πŸ‘©β€β€οΈβ€πŸ‘¨ I'm Horny Tonight Looking for a genuine sexual relationship with a like-minded asian lady? ( Do you want to view my personal profile and my sexy pictures? ) Look no further! As an Asian woman, I value deep sexy connection and meaningful fantasies.. I'm seeking a man who shares those same values and is open to explori...
  • The Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Annapolis Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexu...
  • Help! Single and Got That Tingle! Itchy in Annapolis Hey there boys I'm Natalie here in Annapolis looking for a handy man to take care of some of my feminine needs. Are you talented enough to scratch my itch? Must be skilled, but might take on the right apprentice who has potential. I'll have to keep you on call, because a girl nev...
  • New to the Annapolis area and lonesome! I am new here in this town and I would like to meet handsome gentleman to go to dinner and on date with. You are interested in me please send message to me. @RagazzaSexyX Sono nuovo qui a Annapolis Sono nuovo qui in questa città e mi piacerebbe incontrare un bel gentiluomo per and...
  • hippy_nomad Loves antiques, rescuing stray animals, 420... Must be 420 friendly. Currently living in Annapolis I am an honest, hardworking and caring woman who is looking for the same. Let’s face it we’re not getting any younger so who wants to play games- NOT ME! I also like going to flea markets, dancing and most of all vacationing! So if you ...
  • Wanna touch my amazing?... Hi, LadyV living here in Annapolis and I have need for a hot woman who appreciates my particular anatomy. I have a large butterfly and a BIG button if you know what I mean. I would love to have someone play with them all night and bring me again and again. My record in one session is 21 full O's, I ...
  • Lesbian horse lover wants to meet same Hello girls! I am Sammi and I love my horses. I have three equine companions that I love to ride on weekends and evenings. I enjoy sunset rides and one of my horses is waiting for a co-rider to come out with me. Are you my special lesbian cowgirl? Beginners welcome. πŸ˜‰ Send me a private messa...
  • Achin' for the Bacon in Annapolis Let's Start Makin' Bacon! Hi all, Sheila here in Annapolis, single, a bit old fashioned, a little rowdy, love to ham it up, (sorry about the bad pun) 5'5, 140 pounds, 24 years old, big chested, blonde, blue eyes, love dancing, love beer, smoke but not 420, love animals, have a dually pickup and am ...
  • Wife Swap! Let's Swing in Annapolis Attention Swingers in Annapolis! Adventurous, attractive, athletic swinging couple in the Annapolis 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! ...
  • Minnie the Muff Diver... Annapolis's Minnie Loves Oral I'm Minnie a petite lesbian single girl living here in Annapolis. Wanting to find a woman who is either lesbian, bisexual, or bi-curious for a steady hookup. Preferably a woman who loves oral since I love oral. (giving and recieving) I'm 21 years old, 4'11, 100 pounds ...
  • Late Night Wine & Trouble? πŸ·πŸ˜‰ Looking for a Fun Guy Tonight Annapolis Girlie Seeking Man or couple.. let's go have fun! Sometimes nights can be so quiet. I'm 28yo girlie and love to live life, be fun, flirt and always be up for a laugh. I want chemistry, lots of fun, excitement and lots of conversation with playing involved. Love the initial spark and lust ...
  • Luxury Ebony TS Sugar Baby With Style πŸ‘ πŸ’Ž Hello handsome… I am a ebony trans sugar baby, a beautiful, classy and elegant young lady. I look for confident men that are also very kind to women and who like to spoil a gorgeous lady. Fashion, food and especially great chemistry are my top priorities. let's plan our play date. I love peo...
  • Ebony W4W - πŸŒ™ Movie Night or Makeout Session? You Decide 😘 πŸ“ Annapolis Ebony Lesbian Seeks her Queen, or Princess πŸ‘ΈπŸ˜‰ A soft playful cutie like me is looking for a girl to play with tonight. Netflix and  chill? More like kiss and thrillπŸ‘„ .  I can meet up with you to watch a late night  movie, buy some extra snacks and maybe sneak s...
  • Ebony Mom Energy πŸ”₯ Soft Curves, Grown-Woman Confidence in Annapolis Ebony Mother Seeking some sexy fun, shaped by everyday life - this is who I am. Confidence flows through me like sunlight after rain. When work fades, something quiet and warm stirs beneath the surface. Needs meet longing, balance finds pleasure. Enjoyment matters, yet calm rules above chaos. 😌�...
  • Selena Trans girl cute looking for love Hello boys. I am looking for love. You want meet me? I want meet you too! See my pictures @SelenaIsTrans and send me a message to set up a date. I like going out for food or drinks, having a great time and I especially like great sex! I am preop and can do top or bottom though I kind of prefer top ...
  • πŸ–€ Inked Emo Girl Seeking Man πŸ”₯ πŸ–€πŸ–€EMO Girlie in AnnapolisπŸ–€πŸ–€ Dark circles under my eyes from being woken up at the last minute to try and get my eyeliner on point, lipstick that gets wiped away to the bottom of my chin and a mind that never ever switches off. The constant juggle to keep my mouth closed and my mouth off....
  • Fun and Sexy Girl in Annapolis πŸ’œ Sweet as HONEY 🍯 Bad as SIN πŸ˜ˆπŸ’‹ FuN gIrL just arrived here and needing to get out πŸ₯‚πŸ₯³ So I’m currently in a new city and looking to meet a nice guy to maybe hang out and see where the night goes. I LOVE to talk, have fun, drinks, etc. As long as you have a nice face, a beautiful smile and maybe a bit of a cheeky persona...
  • Free Maryland Transexuals Guide Maryland Transexuals Guide The Maryland 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 Maryland Transexuals Guide online.  Where to Meet Transexuals in Mary...
  • Breast Obsessed Little Booby Boy... Need Mezmerizing Mammaries in Annapolis Controlled by Cleavage, nipples, areolas, breasts, boobies, tits, hypno, highly suggestible, kinks, fetishes all types. I'm Lenny a 5'9, about 160 pounds, 22 year old single male in Annapolis here for magic milk bag fantasies. If you have boobies I'm interest...
  • Flirty thirty-something Lesbian wants party goer Flirty Feminine Lesbian to Party in Annapolis Ok, maybe not always partying but I do love dancing so much. I can dance for you if you like! My name is Selina and I am half Spanish. I speak both English and Español and love to travel when possible! I work from home and my schedule is flexible...
  • MAKEOUT FETISHπŸ’„ Soft Lips, Slow Kisses πŸ’‹ W4M Makeout Queen Seeking Real Chemistry Do you ever wonder how it feels to kiss someone? The smiles draw me in. A deep kiss sometimes says more than words.  I am a woman. I want to meet a man. I like deep kisses. I want dates where we make out. I hope to feel close to someone. If you want W4...
  • Swingers Clubs Directory U.S. Swingers Clubs Directory at BonePage.com Related Link: Meet Local Swingers U.S. Swingers Clubs Directory listings are free for swingers clubs. Are you looking for a sex club in your area? You’re in the right place! Browse our handy list to jump-start your search for great sex and new sw...
  • I'm Troy in Annapolis - Bi-Curious Looking to Experiment... Bi-curious in Annapolis Hi guys, I'm Troy here in Annapolis divorced after 10 years and am entertaining the idea that I might like the gay lifestyle. So, here I am on this site looking for a special kind of man who isn't going to go too fast with me. (is patient) Woman say I'm well hung, ...
  • Latina Mom Heat πŸ”₯ Sweet Smile, Dangerous Curves in Annapolis Latina Mother by day, freaky by night 😈 Living between duty and wanting more. During morning hours, tasks fall into place without effort. When darkness arrives, another version emerges - light on her feet, slight smile, just enough curiosity. 😌✨ MY LATINA MILF DATING PROFILEπŸ“© Warmth flow...
  • Petite TS Doll Looking for a Fun Sugar Daddy πŸ¬πŸ’‹ Hi babe... I'm a tiny trans girl, very sexy and feminine. I love to have fun and I'm a very loving girl, I have a lovely sweet smile. I love to be worshiped and pampered by a dominant confident man, who always takes care of his girl, and knows how to please her. HMU HERE BABE!! I am pretty affectio...