Annapolis, Maryland Sex Ads and Adult Classifieds

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  • August 12th, 2025
  • 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...
  • HEY BOY - Tap into THIS Phat Booty! I ain't playin, I need a man to plunge into my juicy juice and give it to me hard! I got a phat booty and cannot lie cause we need a real man, and only a real man will do. I'm Natalie, 5'6, mixed race, 36D cup, 42 hips and a phat ass baby! If you live in Annapolis and need a booty call like I do the...
  • 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...
  • Naughty but nice girl next door Naughty Girl Next Door I want you! At least I want someone like you...I want love, and friendship and fun dates and mystery drives. Please don't be shy. Come and say hello! Send me a message @NaughtyGirlTrish69  I'm a naughty girl of many interests. Internet junkie, social mediaholic, pa...
  • exciting black guy waiting for you Exciting black guy in Annapolis I am Herman. I am an active and fit, age 32, black male and I am excited to meet you! Looking for lovely lady of any age but not too young to understand my humor and not too old to keep up ;) I am fit and fast to run with and muscular. Tall and attractive. Want to wo...
  • Beauty Queen from India looking for love My name is Manju and I came from India in 2002. I am a college graduate and I work in retail. I am looking for someone who is exciting and fun, but honest and trustworthy. If that is you please message me Manju in Annapolis so we can get together. I look forward to meeting you!...
  • Lets Go Playah! Annapolis Boys Come Out and Play! Mindy here in Annapolis ready to play with a man who has skills. This game ain't for sissies or mommas boys. I know what I want and you know what you want so this whole thing should be uncomplicated and simple. You know the game, it's straight forward and goes as f...
  • Hey Ya'll Its a 3-Way Booty Call! Try an Ebony Threesome With Me! Vera here in Annapolis looking for a few good swingers! Or, at least one good couple. LOL  If you like hot chocolate and a big booty here I am. I got some hefty hooters too that will make your mouth water and hypnotize you so I can take advantage of you. Hit it ...
  • 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...
  • 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 ...
  • Genuine, yoga and jogging woman seeks limber man Woman Enjoys Yoga and Jogging, Seeks Man I am Joy. I really am! It's my real name and I love meeting new people. I am currently single and looking for a real chill guy to hang with and have fun. Send me a Private Message! @ItsPureJoy31 Include your pics for mine. ...
  • 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...
  • Wanting slightly older gentleman Hello. My name is Sylvia, age 24 and I am pretty done with young guys who mess around. I want a guy who is mature and kind and likes to travel. Please contact me so I can learn more about you!  Send your recent pics for mine. I just took some naughty pics with my girlfriend Brianna. I think yo...
  • Busty curvy 38DD wants to date gorgeous guy Busty, Curvy 38DD W4M Fun, busty, sexy woman looking for an equally sexy guy to make me happy, both physically and spiritually. Discretion assured. Please be fun. I will be your dream girl! Text message me (BustyKateX) for a date....
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Annapolis! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Annapolis!  No strings - just great times, so join my page free for instant access! Shemale Gia's Annapolis Sexbook @ShemaleGia27 Photos: 4...
  • Any Irishmen Here in Annapolis? Well, step right up then gentlemen I'm from Ireland and live here in Annapolis for two years now. I am awaiting my naturalization papers to go through so I can become a US citizen. Currently I work in catering mostly for weddings. It's a good enough job, but I'm not here to tell you all about my lif...
  • Hey, fella: Not getting your needs met? Me neither. Let's get together. I want to date someone who is equal and wants to please and be pleased. Let's feel the passion again. Sorry, no strings at the moment because my situation is complicated. Within 10 miles of Annapolis area please. I have a somewhat flexible schedule but an out-of-town hookup just isn't in the cards.&...
  • Cerco signore americano di lingua italiana a Annapolis Bellezza italiana Cerco uomo di lingua italiana a Annapolis Mi chiamo Erina e vengo da Roma. Se si può nder stand questo si prega di testo me così possiamo incontrare. Voglio un gentiluomo americano di lingua italiana per amore a lungo termine. Sono nuovo a questo, quindi per favore s...
  • 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...
  • 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 ...
  • I Need a Sexy Man to Tame Wild Willy! Hung Annapolis Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Annapolis with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks and se...
  • 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...
  • Hey Sexy I'm Gonna Add YOU to My Cart! Shopping Hard in Annapolis Hi there I'm Roseanne about 22 years, about 5'5 and brunette with big brown eyes here in Annapolis. You know girls love to shop online and I'm no different. I'll just add you to my cart and check you out. Now how long until delivery? Huh? I don't do snail mail, so make it...
  • Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Annapolis AREA Hi baby! I am waiting to meet you. I can host or travel to you. Down to earth preop transexual woman seeking an understanding man who can appreciate my uniqueness. I am a great cook and great fun! Let your hair down and allow me to pamper you and show you wh...
  • 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...
  • Italian sweetie looking to taste your fruit Woman seeking woman in Annapolis Amante dolce in attesa di assaggiare la vostra pelle. Riesci a leggerlo? Parli italiano? Voglio parlare con te. Inviami un messaggio @DolceAmante. I speak English too! Sweet lover waiting to taste your skin. I want to talk with you. Send me a message @DolceAmante. ...
  • Annapolis Cougars and Cubs Cougars and Cubs in Annapolis Browse thousands of cougars profiles and join free! ...
  • 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...
  • Superb Shemale in Annapolis... T-Girl for NSA Encounters in Annapolis When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Annapolis. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck ...
  • Bite Me Butches! Annapolis Lesbian for Butches Deena here in Annapolis daring all you bad butches to come get me! I'm fiesty and kitty has claws. You aint gonna get this easy like you think. Yeah sure, I'm a little sarcastic, brutally honest and sexually hostile, but that sort of foreplay leads to explosive sex and...
  • Amazonian Warrior princess looking for her Xena Tall Woman for Woman in Annapolis I'm a soft butch bisexual/pansexual woman. I enjoy cosplay and RPG. You wanna role play with me? My name is Terri and I am 5' 11", medium/athletic build and I have long dark hair. I am fit and muscular from working out regularly. I'm interested in all types of wome...
  • Alex's Huge Throbbing Cock in Annapolis πŸ’¦πŸ’¦ New to the scene, willing to try anything! Thanks for checking my ad. I'm new to this. My name is Alex (hmu @AlexThrobbingCock4u) and I love fucking and getting my huge throbbing cock stroked and sucked to completion. I'm single but not totally out yet so please be discreet. At the same time, I'm a...
  • Shy femme needs love from butch woman in Annapolis Femme for Butch in Annapolis Hello. I am Jemma and I am 24 and very shy. I work Tuesday through Saturday and so my weekends might not be the same as yours. I hope you can accommodate me. I would like to meet a butch lady who looks so handsome, has short hair and long fingers. Please send me a mess...
  • August 11th, 2025
  • Good girls don't, but I DO! Tania Needs Hot Man in Annapolis You can call me a good girl all you want... but that won't change my horny ways. I need more! I need to be touched, I need to be filled, I need to be spanked! Any men in Annapolis who feel me on this? Let's get together and see about some NSA tonight and if it works...
  • Hey ladies, I am Roger, 49 and looking for real love Man Seeking Woman for Dating in Annapolis Hi, my name is Roger. I'm here seeking a woman for dating and friendship - hopefully a lot more! I am 49, a professional with no kids and no personal entanglements. I am local to this area and have lived here for 22 years. I would love to meet a kind a funn...
  • Tall, fit Butch... Butch for Femme in Annapolis Not sure about how this is supposed to go, so here I am just saying I am looking for a date. I am romantic and thoughtful and I will bring you your favorite flowers and take you on picnics. I have a nice home, own my car and I have a good job. I don't need anything but ...
  • 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...
  • 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...
  • Nigel 56, Annapolis new here Male 56 seeks woman in Annapolis Howdy gals, I am Nigel and I am back on the market after a settlement with an ex and my subsequent relocation. lol. That's life. Now, to find my true one and only love. I am lighthearted and friendly and I love to laugh and be made to laugh. I've been single over a ...
  • I will always laugh at screaming goats... Annapolis Man Seeks FWB I’m George age 40 here in Annapolis and am a bit of a shut-in. I still like going out for drinks and having fun but I find more peace and have more fun just kicking back at home. I love the beach, movies, Disneyland, writing music and poetry, spontaneous trips, and pla...
  • Flirty Fun, Endless Kisses & No Judgments πŸ’‹ 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...
  • Annapolis - Let’s Make Some Mischief… And Maybe a Mess πŸ˜‰  Hey gorgeous 😏 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...
  • Lesbians in Annapolis Message Me πŸ˜»πŸ’¦πŸ‘… (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.  ...
  • πŸ’– Sweet, Seductive & Craving Her – Ebony Babe Looking for a Good Time 😘 Annapolis Ebony Lesbian Lover Seeking Woman!!πŸ˜‰ I am a thick, chocolate colour πŸŽ‚πŸ€Ž  , in my mid-20s, with soft curves and  smooth skin, and a wicked little smile. I am playful, affectionate and very into women,  especially if they know how to tease and please.  It should b...
  • 🌺Ebony GodessπŸ”₯TIME TO PLAY! I am affectionate, classy, mature, independent 420 friendly, Super CuteπŸ’‹ Ebony Woman seeking. I love Kissing and Making out.πŸ”Ή♦πŸ”Ή Nice and Sloppy. I want a secret Fuck. I can host or come to your place thats your choice!Age & Size doesn't matter πŸ’‹πŸ’‹πŸ’‹My Profile and Pix Here οΏ½...
  • Tall & Peggable πŸ˜ˆπŸ’‹ 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! πŸ˜‰ 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 ...
  • Let’s Flip the Scriptβ€”You Lead, I’ll Moan πŸ˜πŸŽ€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. πŸ’«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...
  • πŸ‘ Thick & Tempting 🍯 Seeking a King to Devour Me πŸ‘‘πŸ”₯ 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 πŸ’‹πŸ’‹πŸ’‹ If you are into bigger women like myself, then we might have something special. I enjoy being dominant in bed and taking c...
  • Looking 4 a Man 4 Sex πŸ†πŸ’¦ & 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...
  • πŸ‘ Curvy, Confident & Craving Connection – BBW Babe Ready for Fun πŸ’–  A thick, soft, and totally kissable BBW SEEKING WOMAN, I'm in my late 20s here and  I am looking for a sweet (or spicy) girl to spend the evening with. I'm  playful, romantic and always good for a chat (or something a little naughtier) 😈 if  I am in the mood. Get to know me m...