Annapolis, Maryland Sex Ads and Adult Classifieds

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  • June 4th, 2026
  • Irresistible woman desiring to be wanted Hello, I am originally from Portugal and would love to meet a handsome, funny guy to do to movies and dinner with. I am new to this online dating scene but hopefully, you will be nice! Please message me @IberianLady1 Olá, sou natural de Portugal e adoraria conhecer um tipo bonito e engra&cce...
  • Tiffany Shelle - Your Annapolis Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Annapolis It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT ✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% function...
  • Flirty Fun, Endless Kisses & No Judgments 💋 Annapolis  The person I am today is a relaxed yet passionate man who balances his gentlemanly nature with  flirtatious tendencies by sending sweet messages during mornings and provocative messages at night. 😈 I enjoy tasty  food with slow kisses and unexpected plans that typically lead to in...
  • Come Join US!!!! SWINGERS DOWN FOR ANYTHING AT ALL! 😘🔥 Annapolis 💋 Hello babess... I'm Roxxxy and my Hubby's name is Johnny. We're from J. My hubby and I are a very sexy and adventuruous swinging couple who love to explore our  deepest and nastiest fantasies.. We MUST indulge in the thrill of wife swaps and threesomes. The swingers lifestyle has brought so muc...
  • King of your heart waiting for you in Annapolis Abe, 32, local in the Annapolis area, own my own business. I work hard and play hard. I am looking for a gentle guy who is understanding and kind. I love to laugh so you have to be funny, plz. Not all the time, but you need a good sense of humor. Life is too fun to be serious all the time. Message m...
  • Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Annapolis who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all in it...
  • Fun and Sexy Girl in Annapolis 💜 Sweet as HONEY 🍯 Bad as SIN 😈💋 FuN gIrL just arrived here and needing to get out 🥂🥳 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...
  • 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...
  • Bosnian Beauty looking for local chick Bosnian Beauty Looking for Woman in Annapolis Hello. I am Lulu and I am 27 years of age. I am fluent in English and I now live in Annapolis. I am able to travel within a reasonable distance to meet the woman of my dreams. Please send me a message @LuluLynn27 to swap photos and chat. I would li...
  • Naughty boys check me out... good thing I LOVE naughty boys! Kara here, I will make your fantasies come true in Annapolis! I have a bubbly personality, enjoy intimate dinners, shopping, and I love as much as I receive. I dress to impress, love to snuggle, STD free, classy, and ready to satisfy the needs of my man anytime. People who know me would say that I h...
  • Shy girl looking for first date Shy girl for lesbian hookup in Annapolis It is so hard to meet people at the moment and I am really wanting a date. No strings unless we hit if off. I am careful with socializing, so don't worry about me not being safe. I'm a lipstick lesbian femme, looking for fun chick to hang out with and see wh...
  • Thick Latina Looking for a Confident Man 🔥🌹 Hi guys, it's Camila. I am 22 years old, curvy and latina. I think that confidence is probably the most sexy quality a man can have. I'm really into confident men with a great sense of humor who know how to have fun and live life without over thinking things. My Pix - Message Me  I'm a very af...
  • 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 ...
  • Independent Woman in early 40's seeking independent guy Independent Woman 40's for Man in Annapolis I am in my early 40's and I am looking for a cheeky, intelligent man who can make me laugh. He should be in reasonably good physical condition and have a job. Contact me @LizzieBethK if you think you fit this description and we can arrange a date. An...
  • Sweet Guy, Dirty Mind, Zero Pressure 😇Annapolis😈  Hi beautiful. At twenty-nine years old I maintain my fitness while being humorous and charming yet slightly  mischievous. When I look at you my eyes show weakness while my laughter makes your stomach ache  😏 View My Dating Profile and Pictures - My approach to romance includes p...
  • DESPERATE SEEKING A REVENGE FUCK! 🥒🥯💦 Newly single Annapolis 22 y/o female needs a good fuck 💦 Hey there, I'm Trish from Annapolis. Let's get right down to it. My husband left me and I need to fuck to make me forget about his sorry ass. I'm tired of being neglected so I'm looking for a nice, attentive man to keep me warm tonight. I'...
  • 🍻🔥 Wild Nights With Mason What the poster wants you to know: Take a break from the stress of everyday life… and come enjoy fun, flirtation, laughter, and unforgettable chemistry with a confident guy who knows how to enjoy the moment 😏✨ 😍😍 Mason here… athletic build, charming smile, and always down ...
  • 💎 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...
  • Age 47 Regular Guy with a Lot to Offer!! Man Seeking Woman for Dates in Annapolis Hey, Richard here. I just want to say hi to you and hope you might check out my profile and see if you want to go out for a date. I am just a regular guy looking for a regular gal. I've been single too long. I keep busy and have a great life but It's time to...
  • I'm the Girl Your Mother Warned You About!... Ok, but I'm not All bad! What? Just because I want some fun and sexy playtime riding the weenie? Well then just spank me already and give it to me hard and teach me a lesson I'll never forget! Punish me and pound me like you mean it. Is it hot in here, or is it just me? Your mother was right and I n...
  • 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 ...
  • 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 ...
  • Flawlessly gorgeous trans bombshell in Annapolis Trans MtF for Man in Annapolis I transitioned 6 years ago at the age of 18. I'm still fully functional but live 24/7 as a female. I pass flawlessly so let's go out on the town! I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedroom...
  • 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 ...
  • Hey, any SteamPunkers out there in Annapolis?... Hi, I'm Brad T. from Annapolis born and raised. I love everything SteamPunk and am searching for a local woman who appreciates the romanticism of the late Victorian era. I'm 30 years old, love sci-fi, SteamPunk, conventions and events, travel and work. I have a dynamite job working with younger auti...
  • Fabulous Filipina woman wants wonderful man Filipina Woman Seeking Passionate Man Hey guys, my name is Amina and I am full Filipina, just moved here to Annapolis. I want to meet a kind and passionate man so please only message me if you are serious and fun and want pleasure! I am open minded. Hit me up @Amina4Passion to chat online and ...
  • A monster in the sheets, but a lady in the streets... Hello men, I'm Lilith a 27 year old sexy femme, fully functional, passible, sexy and hot to trot trans. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Annapolis area and are interested then drop me a line and introduce yourself. You ca...
  • Annapolis Latina beauty wants love Buscando a un hombre que sepa lo que quiere La gente dice que estoy caliente. Buscando a un hombre que sepa lo que quiere y no tenga miedo de conseguirlo. Escríbeme @ belleza_latina...
  • Intense, vibrant and dark haired beauty, WLTM handsome fun guy Intense Dark Haired Beauty in Annapolis Hey, I'm Janey and I'm still looking. I'm kind of bored and need new friends and maybe some romance. I have dark hair, soft skin, sultry eyes and a great smile to make you happy. How about you? Why not call and let's see where things go? Message me now ...
  • 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...
  • Goth Girl With a Soft Side 🖤🌙 I suppose people think that my dark clothing and makeup is scary. But in reality, I am a very shy girl. I just love music, candles and the weird and bizarre. ( View My Pix and Message Me ) My name is Luna and I am searching for some kind of brain or soul mate. Open to individuality and not really b...
  • Swingers - Estella Wants Threesome - Live La Vida Loca! Hi Annapolis Swingers I am Estella looking for some real fun - Estoy Muy Caliente muchachos y muchachas! I have a need only you two can fill. You don't have to be super models or anything just come with a sexy attitude and that makes it all good in my book.  I prefer a hispanic or white couple...
  • Help - I'm a Nymphomaniac AND an Insomniac - There is Only One Cure! I'm sort of a reverse Sleeping Beauty story. lol I need lovin to put me to sleep and give me those feel good endorfins. I want to find a sexy man to hookup with when the need strikes me. Of course you can let me know when the need hits you too. This isn't a one way street after all. I'm 29 years old...
  • 🍒🍑💦sexy girl🍒💋🍓🍆Annapolis🔥🔥👌nuru💦 b2b🍌🍆 I enjoy getting down and dirty in the bedroom, trying out different positions like doggy style or reverse cowgirl. I have a kinky side too, so if you're into some light bondage or role-playing, count me in! 😈Swap Pics & HMU - LET'S HOOKUPIf you're looking for a no strings attached encounter f...
  • Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Annapolis Hey! Thanks for looking at my ad. This is the first time I've done this so bear with me plz. I am Jared, FtM trans man. I transitioned at age 25 and I just turned 30. Come and meet me!  Check my personal profile @FtMJared29 and say hi!&...
  • Nice Guy? Yep. Push-Over? Only When You’re Behind Me 😉💦 I'm a hopeless romantic at heart, always looking for ways to show my affection and make you feel like the queen that you are. 💖 I believe in chivalry and treating a lady right, so get ready for some old-fashioned charm mixed with a modern twist. Swap pics & contact infoSo if you're ready...
  • 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...
  • Looks Innocent. Absolutely Isn’t. 😇😈 Sweet in Public, Unfiltered in Private A grin slips out, then comes the quiet reply - thank you, yes, and sweetness stays visible here 💕Still, once the curtains shut, I refuse to trim who I am. Message Me Here 💬  Something about quiet sparks, long stares, one talk that grows soft then j...
  • 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...
  • Successful Sex Genius! Clever Lesbian in Annapolis Inventor of the Hindlick Manuever, Jodi here in Annapolis. I have impressive credentials such as a sexy vibe, perky tits, great complexion, 24 yrs old, blonde hair, blue eyes, 5'6, 120 pounds, dirty mind, love oral and toys, love kink and fetish, and open minded. Yo...
  • Super hot guy waiting for girl of my dreams Black Man for Romantic Woman in Annapolis Dark chocolate man with romantic nature. My name is Dwayne and am 6 feet 3 and well built. I am into sports and I love watching football. Life is good and all but I want to meet a beautiful woman for passion and adventure. Check out my profile @DwayneSeekin...
  • June 3rd, 2026
  • OKAY I Admit It! I'm Feeling a Little Frisky in Annapolis Where's My Boy Toy in Annapolis Ramona, 22 years old here in Annapolis and in need of some male company. I have an itch that only you can scratch. Hmmm, what do I want cause you guys come in all kinds of flavors and sizes. It's like being a kid in a big candy store. I know, why don't you tell me wh...
  • 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...
  • 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...
  • Sofia es Nueva en Annapolis y sola Nueva en Annapolis y sola Nuevo en la ciudad y solo. Me gustaría conocer y salir con alguien que me plazca. Envíame un mensaje @SofíaSexy28  Mujeres solo por diversión o relación a largo plazo. Username: @SofíaSexy28Location: Annapolis, Maryland...
  • Hot Latina looking for love Latina caliente buscando amor. En la música de fiesta, jugar, acampar en la puerta y todo tipo de diversión física. Me Text para una cita! @latinacaliente27 Hot Latina looking for love. Into party music, playing, out door camping and all kinds of physical fun. Text me for ...
  • Beach Lover Looking for a Chill Guy 🌊☀️ Hi, I’m Kayla. If you love the water like I do, you will probably get to know me pretty well. I am a very easy going person who loves to live a sun filled drama free life.. I am quite a down to earth, fun loving person. I love to chat and I enjoy a conversation that may go in many different di...
  • 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...
  • Don't ever play leap frog with unicorns! Hi I'm Claire, a cougar here in Annapolis to show young men that with age comes wisdom like in the headline above. lol I am willing to share my acquired knowledge with eager cubs who want to be shown a better way. Of course most of the knowledge I have would be sexual in nature since that is why I'm...
  • Butch tomboy looking for beautiful femme Butch Tomboy for Femme in Annapolis My name is Toni and I am tall with short hair in a sort of spike and I work out regular. I love running and hiking and biking and photography. Dog lover, mom to 2 bulldogs, Smiley and Ranger. When I go out into nature I find myself at peace and I want a partner w...