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

• October 31st, 2026
• Bryan for Hot Male-on-Male Action in Annapolis Bryan M4M in Annapolis Hey guys! I'm Bryan, looking for some hot male-on-male action. I want to meet a guy in the Annapolis area who is ready to get down and dirty with me. See my pics and contact info @Bryan24m4mX.I'm primarily top but can switch for the right guy. I love getting my big thick cock...
• Let’s Flip the Script—You Lead, I’ll Moan 😍🎀Annapolis Hey there, lovely ladies of Annapolis, My name is Wells and I'm on the hunt for someone special to explore this beautiful town with. 💫Swap pics & contact info  I'm a thrill-seeker at heart, always on the lookout for my next adventure. Whether it's hitting the slopes together or enjo...
• DIVORCED👩MOM/MILF Hey Love I am an older cute girl Horny for sex ,& I love to kiss and suck your dick. Bareback, Anal, Greek, GFe ,bbjs, kiss I love getting my pussy licked while I suck cock. I can host, but, willing to travel. 😘 I have nasty videos for sell💋 I'm 42 Years 🅳🅸🆅�...
• Wife Swap in Annapolis Anyone? Swingers Seek Sexy Swap in Annapolis Hi we are Dave and Lisette here in Annapolis. Admittedly we are pretty new to the swinger lifestyle and don't want to cross any boundaries, but we would really like to find a couple around our age to swap partners with. You don't have to be married like us, just...
• Gay Russian Bear New to Annapolis... My English is not so good yet. I am Vlad from Moscow, Russia and want to find gay young man for sex in Annapolis. I am 34 years old, 6'2, 210 lbs, blue eyes, big size penis, not cut, stay in good shape and love good party.  I am here for 3 years, engineer and single, but still no car. If you a...
• Annapolis Cougar Could be a Cubs Delight Tonight!... Cougar on the Prowl in Annapolis Hi there you sexy cubs I'm Joan and I'm gonna spoil you tonight! My den or yours, let's get wild in the sheets till I've had my fill. If you are a cub between 18 and 30 and live in the Annapolis area then I've got something for you. Maybe you thought school wa...
• Local Librarian wants to let her hair down Woman seeking woman in Annapolis Hey, I'm Josephine and I am a 32 year old librarian. Even though I am not a typical looking librarian I am pretty good at what I do and I love working around books as well as digital media. I am an avid reader and I would love to read you a bed time story. I must co...
• Hello! My name is Alexis in Annapolis Sex Hookup in Annapolis If you are looking for someone to entertain you and be your ultimate fantasy girl, that is me. I am hot and sexy and want to hook up with someone with warm feelings and a bright personality.  Send your pic for mine.  AlexisXoXoXo If this ad is online then I'm avai...
• 𝔹𝔹𝔹𝕁 𝔾𝔽𝔼🌮💦 LATINA🌮100% new girl🌈🔞LATINA💖 Annapolis Hey there, I'm Rene from  Annapolis . I'm a fun-loving girl who's always up for trying new things in the bedroom. I love to explore my fantasies and play with different kinks. Are you ready to join me on a wild ride of pleasure and excitement? 😉 When it comes to sex, I enjoy getting a l...
• Nerdy Guy Seeking a Cute Dude 🤓💬 A bit of background I'm usually quite pretty much invisible, but I'll be a bit more noticeable once I'm awake. Tech kind of person among a few other things. Self-proclaimed self-styled pop culture geek and obsessive love of cinema and video games. Wide awake at late hours of the night having empty c...
• Petite TS Doll Looking for a Fun Sugar Daddy 🍬💋 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...
• Nerdy Tech Guy With a Fun Side 🤓💬 The first time you meet me, I think you would describe me as the smart quiet guy until the playful man comes out. I work in the tech industry and am a huge movie and game fanatic. I love to have long conversations in the dead of night about everything from travel to the most useless piece of trivia ...
• Inviting eyes and seductive thighs wanting to find loving guy in Annapolis I advertised here in the past and thought I found my true love. Well, I guess not so here I am again.  I recently moved, so I am new in Annapolis and have no local friends to hang out with. I would love to meet fun, down to earth guy to explore passion and hot sex. I just need to have some fun ...
• Mature Wealthy Man Looking for Twink Boy Toy... Hello boys I'm Tony 48 years old and been out for 10 years now and take good care of myself. I'm from Cleveland originally, but moved to Annapolis to start over again after my divorce. I don't really have any baggage with the kids being grown up and off to college. I plan to retire very soon and wan...
• 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...
• I'm Danish... Eat ME! Been dating most of my life and nothing too serious, but now I'm ready to settle down with the right person. I'm looking for a woman who will complement me. Where I have weaknesses she will have strengths. She must be local in or near Annapolis, because I did a long distance relationship once a...
• Loves hairy men Annapolis Sally Seeks Hairy Man in Annapolis I love hairy men and I would love to meet a genuine and hairy guy with love to give back! I like the feel of hair on my skin and it has been difficult to meet men who are hairy for some reason. No need to shave for me. I love me a manly man!! Visit my profile pag...
• Latina TS Dirty Girl Looking for a Gentleman's Dark Side 🔥👠  Sweet on the surface. Filthy underneath. View My Trassexual Dating Profile Here - As a TS darling I present like a dream while  playing like a fantasy. Stockings. Heels. A tight dress. Soft skin. And a  throbbing surprise you’ll love exploring 😘 I need you to undress me gr...
• Blue Collar Guy Who Loves Curves 🔧🔥 I am an average guy with fairly average values. I believe in hard work and the simple things in life. Like to expect the same from others. Very frank and honest. Looking for the same in a woman - a woman who can look after herself, but is also comfortable in her own skin. I'm around if you want to c...
• Sweet & Sinful – Submissive Babe Seeking a Domme to Take Control 💦 Annapolis - W4W BDSM/KINK Seeking Slave, or maybe you are a switch like me? I’m a soft femme, in my  20s, curvy, obedient when I want to be and very much wanting to try something  filthy, fun and consensually intense. WANT TO LEARN MORE ABOUT ME?  How about a drink first, perha...
• BBW Lesbian in Annapolis Sucker for love BBW Lesbian in Annapolis Hey ladies, My name is Joanne and I suck at love! Ok, what I mean is, I love to suck. Definitely a 'boob' woman and if you got em I like em. Big, small or medium, it doesn't matter. I'm ready to spoil your body! Message me @JoanneBBWfem. Serious dates only please. Send...
• Strict Shemale Dominatrix in Annapolis - @DesireeTransDomme Powerful African-Queen Dominatrix in Annapolis I am full-time professional Domme Desiree. My Annapolis area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will lear...
• MASSAGE/BJ/NURU - VERIFIED✅ I'm JENNY LOVE ❤️, an exotic & rare bombshell that is the perfect mixture of sweet and sassy. I have stunning long legs, soft glowing skin & seductively mesmerizing eyes. You will love my petite body and nice smooth skin. Let me Massage you and make you cum! 👉If yo...
• Tall, Dark, Handsome Lesbian My name is Selena and I am tall, dark haired, in my 40s and still in my sexual prime! I have Latin heritage and I am fiery but kind. I do not have a bad temper but I am passionate. Age doesn't matter as much as personality and spirit. Any race, any height/weight. I love all body types as long as you...
• 💌DISCREET AFFAIR💌 I'm in Annapolis  and I just really need to get out and have some sex. I am married, so I need to be discreet. I'm willing to travel and even play in the backseat of the car.. I love giving bjs. Let's cheat together babe. 😉  View Profile - Browse Pix CHEATING WIFE - AFFAIR ...
• Do you know the difference between a dick and a bucket of popcorn? You don't know? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Annapolis tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer th...
• Looking 4 a Man 4 Sex 🍆💦 & Fun😍🤩 I really need to get out and have some fun, maybe a drink, smoke.. Sex -  Message Me❤️ I've been really horny and just stuck at home. I have a few GF's who might want to join us and play too, if you're down Or I'm willing to go out and have fun just us. Will you help me get out and have so...
• You want to date me, right? Man seeking Woman in Annapolis Hey, thanks for checking out my ad. I am Noel and I am here to let you know that you don't want to miss out on dating me. I am a joker and I love to laugh and make you laugh too. I am a music fan and I love going to live gigs. Who are your favorite musicians? I have e...
• F/M seeking love and fun Female to Male Trans Man in Annapolis My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. This feels right and I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and o...
• 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. 😉 Send me a private messa...
• Annapolis Fetish Lover seeking hot, kinky fun! Annapolis Fetish Lover for Hot, Kinky Fun! I am a seriously fun woman who has a naughty side. I have never put an advert on here before, so I hope I am doing this right. I just turned 28 and I am about 5' 6" with a curvy body and slender legs that go on forever and look great in stockings. I love ...
• Erotic exotic Asian queen in Annapolis now (25) Asian Transexual in Annapolis Stunning TS - Talia 25. Asian mixed race, non op, loves sex. Nice build with long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information. Classy in public but trashy in the bedroom. Versatile and attentive to your needs. Long...
• 29 Year old lady seeking secret rendezvous I am presently separated but I need to keep things discreet. If you don't mind, we should keep things secret and naughty. I like fantasy play and will try fetish stuff. I haven't put an ad on here before, but, hey, if you don't try, you never know! Send me a message! @Rendezvous29Annapolis Send me ...
• I'm Sexy and I'm Noah!... Single Black Man 4 No Strings in Annapolis Black male, 33, 5'11, 180 pounds, with a good education and positive attitude from Jamaica originally. I have lived here in Annapolis for about 10 years and love it. There is always something to do. I am looking for an original woman. What I mean is ...
• Lesbians in Annapolis Message Me 😻💦👅 (W4W) Ladies whowant lesbian sex NO MEN Please.. Looking for a sexy lady to play with tonight, W4W Women only please, I'm strickly lesbian. I love pussy. i'm local and ready to play.. So if you're a lady who wants to play with another sexy lady, hit me up.  ...
• Looking for my sexy ride or die man Hi gents, Gina here I'm a tatted 26 year old biker chick at heart who is into more mature men, and I live by the biker's code. I am loyal, love the feel and freedom of riding and always give my road king the sex, affection, attention and space he needs. Take me for a ride sometime? A good ride alway...
• Join Me for an Episode of The Hung and The Restless! Endowed Annapolis Gay Man Seeks Hookup I'm a gay man living in the Annapolis area with 10+ thick inches of uncut restless pleasure. I'm Matt 28 years old, 6'0, 200 pounds, muscular, black hair, brown eyes and take care of myself. I'm top, but can be versatile depending on you. You will find me warm...
• Single Female Wants to Explore Fetishes... I'm Dani, a sexually adventurous woman who is looking for a fetish playmate in Annapolis who is able and willing to go with me on this kinky journey. In past non-kinky relationships I have always played a more dominant role (for some reason) however I have changed my mind and I am keen to switch to ...
• Roses are Red, Violets are BOOBS! Woman Seeking Boob Man in Annapolis I'm Violet! Just a girl living here in Annapolis all my life except for a short time in Tucson, AZ. I'm 23 years old, big natural titties, redish hair, blue eyes, big sexual appetite and love to have a man treat me to a long blissful booby rub. That gets me ...
• 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! ...
• 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....
• I'm the Girl Your Mum Never Warned You About!... But then, how could your mother have known? I'm Dirty Diana corrupting good decent honest men like yourself here in Annapolis for many moons. I got a big secret and it's show and tell time baby! It's easier to show you than to tell you. I'm fully functional and passible. I need a sexy man who lives ...
• 💎 Adorable Sugar Baby 💎 Seeking his Generous King 👑 📍  Location: Annapolis    Seeking: A kind/dominant daddy👑  A Little about Me: Hello everyone! I am a sweet, fit blonde with a flirty nature  and an appreciation for the good things in life. I enjoy being pampered, looked after and treated  like a king. If you...
• I've Been Naughty and Need a Spanking!... If you are a sexy disciplinarian man in the Annapolis area and have a strong hand I NEED a spanking to get my juices flowing. (oops! I meant to say to pay for the bad things I've done!)  I'm an Italian/French girl 22 years old w medium build, and an appetite for punishment and erotic NSA encoun...
• 💦Male for Male – NSFW Only: You Dom, I Submit. Period. 😈🖤  The advertisement is not intended for casual greetings. This is: You top. I bottom. You  take. I give. You tell me what to do. I do it. Simple. Dirty.  Hot. View My Gay Dating Profile Here - ❤️✨ I completely submit to all things kinky while being body-positive and ready to sur...
• looknsee - BBW - Brings a Lot to the Table in Annapolis... BBW For Hookup in Annapolis Hola in Annapolis, I am Emma sunshine mixed with hurricane, the type of woman that works and plays hard. I enjoy every second of my free-time. That usually entails being around the people I enjoy, playing with babies, dinner, and drinks, and lively conversation. Tha...
• Sugar Magnet Looking for His Sugarbaby in Annapolis... Hi, I'm Matthew a semi-retired Real estate developer recently divorced seeking my sugarbaby for sexy good times and companionship. I have a yacht, penthouse and nice cars, but still something BIG is missing... YOU! I admit, I'm not the best looking guy, but you could do worse. Do you like to travel?...
• Italian hot woman looking for love Adriana Hot Italian Woman i guys!  my name is Adriana and I am from originally from Italy. I moved here recently and want to meet a nice friendly, fun guy. I own my own private cozy place. I am friendly and a fun girl. Message me. See you soon! ~ Adriana in Annapolis...
• Black/Ebony Transsexual - Your New Addiction – One Taste and You’ll Beg for More 🍑💋  Warning: I’m addictive 😘 View My Ebony TS Profile here - I possess more than attractive features. I am a complete  TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and  thick thighs and soft lips and a hidden secret th...
• Sweet Southern Girl Missing a Gentleman 🍑🌙 Hi there… I’m Savannah. I’m a native Southern belle through and through, so I truly believe in all the old-fashioned values of being a kind, courteous, and chivalrous person, while also always looking and feeling beautiful. Message Me and Let's Plan!!  I am a friendly, lovin...