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!

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

  • November 2nd, 2026
  • 💜 Cute TS Girl Looking for the Right Guy 😘 Just moved to Annapolis😊 Gorgeous, very sweet and easy to get to know. I am a trans girl seeking to meet men that are confident and know what they are looking for, yet are also looking for some friendship with a new person. I enjoy going out for cocktails and having a good time, flirting with the...
  • 27 Yr Old Columbian needs affection 27 Year Old Columbian Hottie Have you got what it takes to please me? I have what it takes to please you, and I know it! If you are serious about being serious and you want love and affection I am the girl for you. View my pics and contact info @Alejandra27...
  • Nikki Needs a Man Who Can Keep Up 😘🔥 Username: @NikkiAfterDark Dating Profile: Yes Pics Available: 14 Video Chat: Yes Messenger: Yes Message me directly if you’re serious 💬 I'm Nikki from Annapolis and I'm feeling a little bit spicy tonight. I don't really feel in the mood for chatting but I'd love to flirt with you, sed...
  • BIG n CUTE BBW for Male in Annapolis 🍑🔥 Brianna BBW for Annapolis Male Cute, flirty and playful BBW seeking a nice man in the Annapolis area. 🍑 I'm curvy in all the right places. I like to dress nice and I'm classy in public. But I love getting down and dirty in the bedroom! I'm a hot, naughty girl who wants it all. I love exploring s...
  • 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 ...
  • Late Night Wine & Trouble? 🍷😉 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 ...
  • Latina Mom Heat 🔥 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 PROFILE📩 Warmth flow...
  • Where's My Sexy Marlboro Man?!... To me a sexy man who smokes is hot AF. Hi, I'm Hannah living in the Annapolis area wanting to meet a single male smoker. I'm 24 years old, Auburn hair, 5'7, curvy with 36C boobs, blue eyes, smoker and want to smoke when you are eating me. You may have figured out that I have a fetish for smoking, be...
  • 🍑 Thick & Tempting 🍯 Seeking a King to Devour Me 👑🔥 Hey there! My name is  Chelsey and I'm a Curvy Cutie..  I am a 26 year old BBW thick girl looking to meet a hot man for some sexy hookups and dating 💋💋💋 If you are into bigger women like myself, then we might have something special. I enjoy being dominant in bed and taking c...
  • Chunky Monkey looking for Hunky Tomboy Chunky Monkey Fem for Hunky Tomboy I am nice and curvy but not heavily overweight. I am looking for a chick who is handsome and butch but with some feminine qualities. Like it's ok if you cry at a movie! lol. I am 21, work full time and drive my own vehicle. I am looking for the right gal to make m...
  • No Strings in Annapolis - Hot and Sultry, Looking for Affection Thanks for opening my ad. I've been neglected for far too long and am in need of affection. Things are complicated so no strings only please. That is likely to change at some point in the future. My hair goes down to my lower back and I have soft skin. My height is 5'8" and I am slender but curvy i...
  • ShopinRound38 outgoing, funny, and independent (Please only message me if you live within 50 miles of the Annapolis area) . I am winding my career down and am wanting to traveling more and work less. Looking for someone to share intimacy and good times with. It’s getting harder and harder to find someone the old fashion way, so though...
  • 💪🍆 I'm All Tha Chocolate You Could Need 💪🍆 Hey I'm new to dating sites but I'm ready to give it a try and see who might message me. I'm wanting to get out and have some fun. Yes I'm black and yes I have a thick 🍆 but I'm so much more than that. Also I want you to know that I love all shapes and sizes of men, I just want someone I can conn...
  • Don't Worry I Bite! Feisty redhead trans in Annapolis full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to control...
  • Joker and a Smoker... I'm a 30 year old, 6'1, 200 pound hardcore biker living in Annapolis and I go by the handle of Joker. Looking for my sexy road queen who preferably smokes too, or at least doesn't mind that I do. All this anti-smoking shit brings out the rebel in me, and if you're like me then we'll get along g...
  • New Body New Me M2F in Annapolis Hi, I'm Natasha, newly transitioned, exploring this beautiful new chapter in my life, and ready to date. Gorgeous non-op with slender legs and curvy body. Want to come and join me for a drink? I love sex in my new gender!!! Seeking a local area man who will enjoy sex and passion wi...
  • 💯REAL💯HANDSOME💯MANLY You ready for some manly gay sex here in Annapolis? I know I am, I made this ad to make a nice BF to fuck or fuck me.. We can even find some other sexy guys to have some sex with too.. I love partying✨ and having group sex. Do you like to take it or give it? I will give you something to suck on al...
  • FEELING H0RNY? I'm Your Dirty Little Secret 😈 CAM SEX BUDDY! 👁️‍🗨️💦 I'm horny and bored 😈 so I set up my sex cam 👁️‍🗨️💦 I specialize in kinky fetishes. Seriously, I like vanilla sex but I also like to taste all the flavors too! 😈 Join my cam (online now) and tell me your kinky secrets and deepest sexual desires and I'll share mine with you. T...
  • Nervous and new to this! It's my first time posting an ad of this sort. Not even sure what you want to know. I can start with my name, which is Rose. I love to travel and have been all over the place! I have a wall in my home which is dedicated to all the postcards I have sent myself from all the places I have been to. Una...
  • New in Annapolis. Lesbian Bondage Anyone? My name is Michelle and I am ready to meet the girl of my dreams to explore the world of bondage and light BDSM in a safe and erotic setting. Send me a private message if you would like to swap pictures, chat and meet up. Attractive, fun, slim build, light hair. Let's see where this leads us!! Us...
  • Latina Beauty needs love in Annapolis Hola señoras. Soy Juanita y soy local en esta zona. Tengo un trabajo y tengo mi propio auto. Puedo viajar para conocerte si quieres conocerte a mitad de camino. enviarme un mensaje @Juanita4love.  Hello ladies. I am Juanita and I am local in this area. I have a job and I have my ow...
  • 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...
  • Looking for Mr. Goodbar... Just out, and just out of the Marines, now a college student and 22 years old gay male living in Annapolis Looking for experienced well endowed older man to give it to me. I'm 5'11, 180 pounds, blue eyes, brown hair, 7in cut, and in great shape. This is a little awkward, I'm new so be patient with m...
  • Blonde College Girl Looking for Fun 😉w4m📚 Username: @SkylarOnBreak Dating Profile: Yes Pics Available: 11 Video Chat: Yes Messenger: Yes Message me directly if you’re real 💬 I'm Skylar here in Annapolis.. I'm a college girl with blonde hair and way too much school work to do. I like confident men that know how to please a gir...
  • Hot stuff hoping for her sugar daddy Hot Stuff for Sugar Daddy in Annapolis Hello gentlemen, I'm Kayte. I’m sexy, flirtatious, sweet & fun loving with a very wild edge. I am 5'4" with silky black hair. I am your ultimate hot girl next door, but with a very down to earth vibe. Let me spoil and mesmerize you!  Exclusive ...
  • Divorced College Lecturer Looking for Excitement! College professor and divorcee, age 42, looking for someone loving, intelligent and fun. I live in the Annapolis area and I am happy to meet at a neutral place or entertain at my place. I own my own home and I am not expecting you to pay for everything. Looking for someone who loves history and book...
  • Hot and kinky MILF looking for some fun in Annapolis Annapolis MILF For Kinky Hookup! Hi all you sexy Annapolis guys, I Georgia and I am an slightly off beat working professional mom of two. MILF. Just looking for some sexy fun and to explore my (and yours?) kinks and fantasies, FWB. I am into men, but possibly women or even a hot couple dependi...
  • 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...
  • Tired of Fakes and Game players? Want hot juicy and tight? Real Annapolis Girl, Hot, Juicy & Tight 100% real Annapolis girl and very skilled! My tantalizing curves and sexy eyes will have you mesmerized in seconds.  Enjoy my silky skin, luscious legs and sensual breasts.  I love to tend to your needs. I promise a safe, sexy and secure e...
  • Your Ultimate Erotic Experience!! Don't Miss Out!! I am very honest, sweet, and loving young woman, I am a Christian, that is my background, religious and I believe in real love, I am here looking for real love and a man that I believe I deserve, I love cooking, dancing, cleaning, watching movies, I am down to earth outgoing woman. I have been in an...
  • Wanna play threesome in Annapolis? Swinger Couple 4 Threesome Me and hubby have been together for fifteen years now and are happily married. We live here in Annapolis and are adventurous as well as fetish friendly. We want to find a third man or woman to come play with us for some adult fun. Of course we will have to meet to make su...
  • 🎶 Concert Vibes & Bedside Rides - Annapolis  Cute Lesbian Girl in Annapolis seeks her lovely playmate!! Oh beautiful 💖 I would love to meet at a local show, dance a little too close  and make out in the parking lot like teenagers? In reply I'm 28, femme leaning switch  and I like high energy chemistry. It's about time someon...
  • Ohhh Yeah! I'm PHAT AS HELL BABY!!! BBW Wants FWB in Annapolis LustyPhatty (Susan) here livin' large in Annapolis. I know you are cravin' my curves and big playful funbags, and I got a few cravin's of my own. I want you to play with and massage my huge titties all night. (heaven) I'm a BBW 34, 5'3, 42EE cup, and will tell you th...
  • 💕 Late Nights With Scarlett... ✨ Newly single. Looking for the sexy version of the right guy. Another single female looking for a single male to mess around with. My name is Scarlett😘. I'm a flirty 20-something year old (slightly irresponsible for my age, I know). I'm looking to meet someone who is fun, spontaneous, slightl...
  • Having fun and Staying Young Young-ish trans fem looking for nice date with lady. I am kind and thoughtful and you will have a very good evening if I take you out. Let me know what you want to do or where you want to go. View profile @SherryTransFem33 and message me. Send your pics for mine. I'm hoping to find real chemistry an...
  • November 1st, 2026
  • Petite Annapolis spinner girl for threesome... Little Bombshell in Annapolis for Threeway Hi ladies and gents I'm Jamie and I'm looking for a FWB situation with a hot couple who lives in the Annapolis area. (willing to travel) As the title implies I am petite; only 5'1 and about 100 pounds. I am 22 years old, Italian, hot blooded and love to ri...
  • Prefer a Man Who Lives Here in Annapolis... Hi guys I'm Shirl here in Annapolis looking for my local prince to put a little pep in my love life. I'm a romantic, but not expecting a long term relationship off the bat. If that's where things lead us then great! If not then that's ok too. It has to be right, know what I mean? There has to be che...
  • 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...
  • Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Annapolis boos out there. I'm a sexy trans woman currently living in large and lovin' every second of it. Hit me up cause I Wanna ROCK too! I'll show you what a real woman can do and everything you don't know now. I'm s...
  • Single Mom wants to Date Funny Guy Single Mom in Annapolis I'm a single mom. I am 31 and ready to mingle and have some fun. I want a guy I can be friends with and enjoy running and fitness with. Being funny is a must! Message me! @Mommykins I love being physically active and especially enjoy romance and sex. Send me a message ...
  • Fit Gym Girl Seeking a Workout Partner 💪😉 I spend most of my free time at the gym. Ashley: athlete, people person and the bubbliest person you will ever meet. Very energetic person. Confidence, health and a good attitude are a few of my favorite things. So if you're a confident, healthy and happy man looking for a good friend then lets giv...
  • Glamorous TS Sugar Baby Ready to Be Spoiled 💎💋 Hi handsome… I’m a beautiful trans sugar baby that loves the luxuries in life and I’m searching for a confident man who will treat me like the queen I am. I am very soft and feminine with a playful edge and you will always have a smile on your face when we talk. View My TS Sugar B...
  • INSTA ACCOUNT LOCKED 30 DAYS for TOS violations. Wanna Swap Pics Insta Account Locked for TOS Violations I guess they don't like nude pics anymore or maybe my pics are just too hot for Instagram. Don't worry, the show and free pictures are still going on. What's wrong with nudity and sex anyway All I want is to hear whether you like what I post or not. It helps ...
  • Single Mom 👗 With One Free Night a Week Being a Mother takes up most of my hours.Yet on one evening each week, it belongs to her. ( MESSAGE ME NOW✉️_) What draws me isn’t noise or mess. A quiet kind of power does - effortless banter, sparks that grow without effort, calm excitement that simply happens What counts is judgment. W...
  • Cutiecumber is looking for her fineapple Me, I'm 33 years old, independent, profession is banking, recently out and wanting to take things to the next level with the right sort of understanding girl. Not exactly looking for serious right away. I'm testing the waters here in Annapolis so to speak. I don't date co-workers so meeting other le...
  • I’m willing to lie about how we meet... I am a 32yr old half Hawaiian, Samoan, and half German. Born and raised right here in Annapolis. I'm 5'11" 190 pounds and have brown hair and hazel eyes. I’m a Disney obsessed, official Netflix movie rater. I’m also a cereal connoisseur and to top it all off I'm an 80’s pop music L...
  • Professional Wants to Settle down in Annapolis... Gay Man for Commited Relationship Hi, I'm Hal a nurse practitioner ultimately looking for gay marriage in Annapolis. I'm not too particular about race, religion or political bent really. As long as you are a loving and caring person. If you have a hot temper do not contact. I'm over that crap! Will...
  • Let's indulge ourselves in something extraordinary... Hello there boys I'm Tawana a 24 year old ebony female seeking a sexy man for some hot NSA in Annapolis. I'm actually from here and prefer a man who lives here instead of a long distance thing. Mostly because when I'm hot and ready and I need you I'm gonna need you now, and not whenever you can get ...
  • Tall & Peggable 😈💋 Looking for My Boss Babe Hi I am a Single 32 years old straight white male.I'm in Annapolis and I would love to meet and amazing woman who wants to feel a real man! 😉 I love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very oral i love to give as much as receive. I love to make her cum all ...
  • 🍆👅always ready for fun!! Hey sweetheart,🥰 Just text & call me 👻 Hello dear ✅ I am availableI am an independent ,sexy girl ✅ I am always ready to play 💋🚘 I can host or go to your place/home/hotel/casino/anywhere.💕 Message me here or text me ...