Annapolis, Maryland Sex Ads and Adult Classifieds

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

  • August 30th, 2026
  • Looks Innocent. Absolutely Isnโ€™t. ๐Ÿ˜‡๐Ÿ˜ˆ Sweet in Public, Unfiltered in Private A grin slips out, then comes the quiet reply - thank you, yes, and sweetness stays visible here ๐Ÿ’•Still, once the curtains shut, I refuse to trim who I am. Message Me Here ๐Ÿ’ฌ  Something about quiet sparks, long stares, one talk that grows soft then j...
  • Sports loving Female : Rare, grab me while you can! Hello! I am Colleen and I love baseball, soccer, football and pool. Yes, I am for real! I even play on a local team! You want to try and beat me at my own game, ha ha! I like to have fun and spend my weekends playing pool or watching sports. If you are into that go ahead and message me! Sporty_Coll...
  • Single Mom Seeking Adult Conversation ๐Ÿ’ฌ๐ŸŒน Mummy life is chaotic! Life is chaotic. And sometimes all I want to do is talk to an actual adult, have an adult conversation. Well that’s where you come in! I am 30 (ish) mom of 2 and I believe I am a lovely human being. Yes really. And I’m after a lovely man to share it all with. Messa...
  • Hot Girl Wants To Hang Out With Woman in Annapolis Are you cute and fun? I'm lonely and looking for good times with someone special. Just send me a message @HotGirl4XXXFun and I will send my recent pictures. ๐Ÿ”ฅ Please send your pics and contact number. Let's text and go from there. Local fem girl looking for local female friend (butch or fem) to ...
  • Mature Retail Manager looking for Serious Relationship Retail manager seeks serious relationship in Annapolis My lifestyle doesn't make it easy for me to meet people. I have recently moved here from Montana and I would love to meet someone who is light-hearted, fun, carefree but also responsible and intelligent. My name is Mandi. I'm 41 years old and ...
  • Athletic Guy Looking for a Fun Gym Buddy ๐Ÿ’ช๐Ÿ”ฅ A bit about me: I'm quite healthy and fitness oriented, I love working out. I'm 180cm tall and generally a pretty chilled person. I'd love to meet other men who like living healthy, confident and maybe even looking for similar things as me. Fitness enthusiasts, gym rats, and healthy eaters. I enjoy ...
  • Carmel skinned beauty waiting for you in Annapolis Woman seeking woman in Annapolis I am Brandi and I am busty and attractive. I am carmel colored from a mixed background and I am looking for the woman of my dreams. I am passionate and love sex. I'm seeking a fun-loving woman in the area who wants to enjoy the fun things in life. If you meet that ...
  • Older woman seeking mature gentleman for long term relationship Older Woman Seeks Mature Man Seeking gentle fun, soft cuddles and long walks in the park. I am a romantic at heart and love a good laugh. Prefer relationship. Go ahead, don't be shy, message me or call @OlderSexySuzie. We can enjoy life together! ...
  • 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 ...
  • Ebony Street King Looking for a Real One ๐Ÿ–ค๐Ÿ”ฅ About me Confident Black Man with street edge look. My friends say that initially everyone notices my looks and all that because of my height, muscles and deep voice but when you actually speak to me, you soon see that there is so much more to me. Friendly, open and the most honest person you could ...
  • Email Annapolis Shemalesโค๏ธโ€๐Ÿ”ฅ I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...
  • Love Giving Head!!! Hey all you hot men in Annapolis! I'm OralAimie the best at giving mind-blowing head because I love it so much. But then who doesn't love it right? (if we're being honest) Lots of girls say they don't love it, but they are liars! There is nothing like it and every one is different. Long ones, f...
  • Cute TS Sugar Baby With a Sweet Personality ๐ŸŒธ๐Ÿ’• Hi I’m a trans girl, looking for a nice and confident guy. I like to look pretty and be the centre of attention, so you would need to be confident and also respect women. I love going out with friends and love to be social and have fun and laugh. I also love to be romantic and to be hugged, ki...
  • Fun Loving Couple in Annapolis Seeks Female for Threesomes... Swingers in Annapolis Seeks Female Hi, we are Jordan and Riley, a sort of a younger swinger couple in Annapolis looking to explore threesomes with the right girl who is open to sex with a man and a woman at the same time. We look forward to experimenting with some wild fantasies we have and welcome...
  • Short and Sweet and New to the Area Hey guys! I will keep it short just like me! I am new in the Annapolis area and I am single and looking for some dating fun! Send me a message @ShortnSweetKellie if you want to know more! ...
  • ๐Ÿ’ช๐Ÿ† I'm All Tha Chocolate You Could Need ๐Ÿ’ช๐Ÿ† 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 ๐Ÿ† 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...
  • Annapolis - Letโ€™s Make Some Mischiefโ€ฆ And Maybe a Mess ๐Ÿ˜‰  Hey gorgeous ๐Ÿ˜ I’m a 35-year-old guy from Annapolis with a cheeky smile, strong  hands, and an even stronger craving for adventure — both in and out of bed. My intention is  to meet a woman who possesses confidence because I seek someone to flirt with and share laughte...
  • Cute and Angelic European Lady seeking class and handsomeness I am Amelia (@AngelicLace) and I am European. I am financially independent and looking for a gentleman who is like-minded, equally solvent and has exceptional taste in food, wine and likes to have a very good time. Contact me @AngelicLace! ๐Ÿฅฐ...
  • Cunning Linguist... Oral Expert Seeks Woman in Annapolis Hi, I'm Calvin a single male in Annapolis looking for a single woman who is funloving and passionate. I am orally gifted and speak fluent English and have an accent. My greatest oral talent however is in my long tongue - my whiskers are soft and tickly, but...
  • I'VE GOT A GLORY HOLE FETISH - CUM 'N GO! Annapolis Glory Hole! Hi all you sexy guys in Annapolis I'm Riley, and the other girl here is Harper a neighbor who likes to join in the glory hole fun sometimes. We have a club house that has a glory hole set up that's pretty nice actually. Our boyfriends like to watch, but you'll never see them. ...
  • Earth Momma - Strict Vagitarian... Hi I'm Orla, 29 years old, sort of a new age type lesbian in Annapolis looking for a compatible woman who I can share nature's bounty and goodness with. If I start boring you with my star charts, crystals, palm reading or alien theories just shove something yummy and lickable in my mouth. That alway...
  • Sexy young lesbo wanting to date same Hi I'm Melodie! I am 19 and have been out to my family for 3 years. They are so cool and don't care as long as I am happy. My mom suggested I put an ad out online so here goes. Wait a minute... how does my mom know this site?!! hahah, anyway, here goes.  I am into clubbing but also like peace ...
  • ๐ŸŽฎ๐Ÿ“ธ Gamer / Streamer Girl Seeking Chill Vibes & Creative Fun ๐Ÿ’‹ Hey there ๐Ÿ˜˜ I am a gamer chick in Annapolis who streams content while enjoying smoke sessions and late-night activities and good energy vibes ๐Ÿ”ฅ๐Ÿ’จ. My free time consists of watching movies and cuddling with others and developing fresh content concepts ๐ŸŽงโœจ. - MY GAMING PROFILE AND PIX...
  • How do I look? / M4W in Annapolis Man for Woman in Annapolis Check out my profile and tell me how I look. I am Sam. I'm a model, age 32 and told I am darn hot looking. Hit me up and check out my profile @SamAnnapolis. Send your pics for mine. I'm available evenings and weekends.  Sorry guys, no men or couples. I app...
  • Scads of Ads Here, But I'm SPECIAL - That's What Momma ALWAYS Tells Me... Single and Special in Annapolis I'm Rhianna still a bit of a goth at heart and trouble always seems to find me somehow. For now I still call Annapolis home, but would like to see more of the world and find a hot guy. A guy who is SPECIAL just like me ๐Ÿ˜Š If you are a fun lovin rebel in need of a s...
  • 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...
  • ๐Ÿ–ค Fetish Ad: Soft Control & Worship Energy Quiet Confidence. Intentional Attention. ๐Ÿ‘ ๐Ÿ–ค Fascinated by small things. What others pass by fast.Stillness between breaths. A hand reaching just to settle. Things said quietly, without rushing ahead. HMU FIRST, I'LL REPLY๐Ÿ˜ˆ๐Ÿ˜ˆ Confidence shows best when quiet, while focus lands better if ...
  • Mark, 33 Love country music and driving my truck Hey, the name is Mark and I am a country boy now living in Annapolis, age 33, a mechanic and I love to drive my truck out on the open roads. Sometimes I take a blanket and a beer and hang out at my favorite lake a few miles from my house in the Annapolis area. I am self sufficient and I am wanting t...
  • Genuine, yoga loving woman looking for physically fit man Busty Vixen in Annapolis Area Busty vixen with a love for yoga and running. I am active and stay in good shape.  Serious guys only please. Text now @BustyVixenCarole Let's go out on the town, have some drinks, have dinner, whatever you like. I can have fun doing most anything. I like hav...
  • Latina chick looking for the love of my life. Isabel Para Mujero Por favor, dime que estás ahí fuera. Me llamo Isabel y soy una lesbiana solitaria que busca su amor. Ven a buscarme. Sabes que te estoy esperando. Hablo bien inglés, pero necesito mejorar un poco más. Ayúdame a que te ayude. Envíame un mensaje a IsabelParaMu...
  • Sexy and Flirty Terina Ready to Play ๐Ÿ˜˜ Annapolisย ๐Ÿ’‹ Hey there, I'm Terina from Annapolis.. I'm a playful and adventurous woman who loves exploring all kinds of fantasies. When it comes to sex, I enjoy trying out different positions like doggy style and cowgirl - the thrill of new experiences always gets me going. ๐Ÿ˜‰Swap Pics & HMU @terina61947 ...
  • 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...
  • Young, Free and Single but I want to be with Mr. Right. You have got be out there somewhere! I am lonely and I would love to find a funny and happy-go-lucky guy who can be my best friend and lover. I'm hoping you look good in a cowboy hat and jeans! Send me a text to @LonelyinAnnapolis so we can get familiar!  LonelyinAnnapolis...
  • 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...
  • Tall & Peggable ๐Ÿ˜ˆ๐Ÿ’‹ 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! ๐Ÿ˜‰ 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 ...
  • Annapolis โค๏ธโ€๐Ÿ”ฅ Sexy Ebony with Tattoos & Zero Patience for Weak Vibes  ๐Ÿ“Annapolis Dominant Ebony Lady - Seeking Man ABOUT ME: I'm a bit sassy, I have tattooes, I'm in my 20's and I'm looking for some sexy fun. That's why I made this w4m ad in the first place. I work as an event planner. So I know where all the good parties and events are.. ๐ŸŽ‰๐Ÿพ WANT ...
  • Fun Redhead With Freckles Seeking Trouble ๐Ÿ”ฅ๐Ÿ˜‰ My name is Emily, and I am a very mischievous, freckled redhead with an unmistakable grin. And the fact that I’m rather good with a certain breed of handsome man only makes things worse. Visit My profile and See My Pix I love to have fun. Funny guys and unexpected moments turn me on. Whether ...
  • Nice but Naughty 30 year old seeking affection and a good time I am half Latina and half European and have moved here recently. I am lonely, trying to assimilate and I would like to meet a very nice man who wants to play and enjoy life together. Text me for a date! (Naughty30luv) I'm naughty but nice, love a good time, party friendly, have recent pics to share...
  • 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...
  • I Need a Annapolis MILF Who's Got That Sexpertise! Annapolis Man Needs Experienced Woman Hi all you hot mommas out there in Annapolis. I'd love to meet someone to hookup with on a regular basis. FWB style. Young women my age seem to be sort of squirrely and awkward in bed. (just my experience) I picture a MILF as being more focused and educated on ...
  • your place or ours? ๐Ÿ  SWINGERS SEEKING SEX PARTNERS in Annapolis๐Ÿ˜˜ Hey there, I'm Judie from Annapolis. My husband and I are a fun-loving swinging couple who love to explore our fantasies and indulge in the playful side of life. We adore the thrill of wife swaps, threesomes, and all the excitement that comes with the swing lifestyle. View our nudes!What I love...
  • Southern belle new to Annapolis out for a good time A truly southern belle, born and raised with all the charm and grace a lady should have. I love cooking, pleasing my man and music. I'm open to most anything fun. I am open minded, beautiful, and I have a lovely twang! Ya'll wanna meet me for some fun and good food? Please say yes! Contact me! @Sout...
  • Blonde College Girl Looking for Fun ๐Ÿ˜‰w4m๐Ÿ“š Username: @SkylarOnBreak Dating Profile: Yes Pics Available: 11 Video Chat: Yes Messenger: Yes Message me directly if you’re real ๐Ÿ’ฌ 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...
  • 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...
  • So Easy A Cave Man Could Do It! Must Have NSA In Annapolis! Hi I'm Lynn (CaveGurl) here in the Annapolis area looking for her sexy cave man. Simply click the blue link thing down below and take a look at my naughty profile pics and let your primitive instincts take over. No need to re-invent the wheel in your quest for fire....
  • Tattooed Sexy brunette, new in town & craving some fun ๐Ÿ”ฅAnnapolis  ๐Ÿ“Annapolis GIRLIE SEEKING MALE ATTENTION!!ABOUT ME: A 20-year-old brunette woman who has multiple tattoos across my sexy body... wanting to find someone in Annapolis to spend time with a special someone while I'm in college. I'm currently studying to be a teacher.. I recently arrived here f...
  • August 29th, 2026
  • Annapolis๐Ÿ’‹ TS Tina โ€“ Your Naughty Escape, Anytime, Anywhere ๐ŸŒŽ๐Ÿ”ฅ Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world ๐Ÿ˜˜ I possess the right amount of softness while maintaining the perfect playful demeanor and I always welcome men who understand how to treat a genuine wild wom...
  • 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...
  • Redwingz Looking for Princess Charming Annapolis Lesbian For Fun Hi I'm Lucy (Redwingz) here in Annapolis looking for a sexy partner who isn't scared to have a little fun. I like the outdoors, walks in the park, the beach, camping, fishing, DIY projects, motorcycle rides and lots of affection. Open to trying new things. To get hold of m...
  • Secret Lovers ...๐Ÿ’โค๏ธ๐Ÿ˜˜ Shhh Don't tell my husband My Husband doesn't like to get wild like I do. I want to have super sexy fun!! ๐Ÿคฉ๐Ÿคฉ Discreet Messages - Private Message ๐Ÿ’Œ I want to do all the things I'm missing out on with you.. I need to have fun and I need to feel a real man again. Want us to make porn together, meet women ...