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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  • December 13th, 2025
  • Wife Swap! Let's Swing in Annapolis Attention Swingers in Annapolis! Adventurous, attractive, athletic swinging couple in the Annapolis area seeks swinger hookups for social activities and to explore the local swinging lifestyle. Let's go to the clubs and spend time socializing for fun and passionate sex. Kinks are welcome with us! ...
  • 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...
  • 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...
  • 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! ...
  • 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 ...
  • KINKY KENNY FOR HOT MALE-ON-MALE 😈 Horny Man Wanted in Annapolis 😈 I'm Kenny, a horny gay man from Annapolis who is on the hunt for some wild and kinky adventures with a local area guy. I love getting down and dirty, exploring all kinds of sexual acts and fetishes. I enjoy giving and receiving blowjobs, rimming, playing with dild...
  • 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 ...
  • SEPARATED MOM 🧸 Seeking NSA Hookups in Annapolis Separated mom for sex hookup in the Annapolis area This is my first time trying adult classifieds. I'm pretty shy at first but I open up quickly after getting to know someone. I have an active imagination and fantasy life. I'm a kinky, naughty girl 😈 looking for some hot fun to let off this sexu...
  • Calling all Swingers and Boobsters in Annapolis Cali Needs Threesome in Annapolis Hi I'm Cali a single girl 24 years old with extra large boobs here in Annapolis looking for the right kinky couple who will love'em. You might be boobsters if you know what motorboating is. You might be boobsters if you know more that 7 words for breasts. You might...
  • 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...
  • Hung Black Male Annapolis for male action Wants hot male for male sex in Annapolis. All races welcome. Want some hot male-on-male action? Well, look no further because DeAndre is here to satisfy all your dirty desires. Private message me @DeAndreXXX24. I love hot dates with hot guys, any race. Pretty much top because I prefer being in char...
  • SWINGERS SEX NETWORK Locals Join Free! LOCAL SWINGERS FORUM Swingers, Swaps, Threesomes, Groups & Sex Clubs! Local Swingers | Pic Exchange | Sext with Members  1. Signup Free for instant access2. Chat up hot locals & swap pics 3. Arrange local swing hookups!   KenNKat:&...
  • Breast Obsessed Little Booby Boy... Need Mezmerizing Mammaries in Annapolis Controlled by Cleavage, nipples, areolas, breasts, boobies, tits, hypno, highly suggestible, kinks, fetishes all types. I'm Lenny a 5'9, about 160 pounds, 22 year old single male in Annapolis here for magic milk bag fantasies. If you have boobies I'm interest...
  • 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...
  • Sensual Dating Sensual Dating with Jen Wanting to date sensual caring man. I will do things the way you like. I like super open minded guys who show respect. Kink friendly!!!! Just pm or text please, no calls. My contact info is here SensualAnnapolisJen Open minded Kinks welcome Femdom  420 fri...
  • 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....
  • George, 31, long beard to tickle you with Bearded Man for Non-Bearded Lady in Annapolis Hey ladies, I am George and I am 31. I have been growing my beard for 3 years and it is nice and long. If you like bearded dude let me know and send me a private message @BeardedGeorge. I'm fun loving, athletic, Alpha type guy, comfortable in my skin, a...
  • I am Caroline and I am lonely Caroline Seeks Female in Annapolis  Hey ladies, I'm Caroline. I have only been living in the Annapolis area a couple months and as you can imagine I have not had much chance to meet other women. If you are lesbian, bisexual or bi-curious and want to meet me please send me a message and se...
  • I Need a STEAM ROLLER Baby!!! I want you to inject my soul with that sweet lover's pole till there ain't much of me left behind. I'm your whore so just F my brains out tonight. I'm a naughty trans looking for a top big boy to have his way with me. So it's heels and ass up and earth moving sex the hard way. That's the way I like ...
  • Amazing kisser looking for lips to practice on Lipstick Lesbian Loves Kissing Do you love kissing? I do! I love it!! It is such a turn on! My favorite parts to kiss are my neck and my face and my lips and my whole body! I am Kimberley, 22 and a part time waitress. I'm eager to meet you!! Send me a private message to @LipstickLesbianKim User...
  • 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 ...
  • Are You Uber Horny? I AM - Maybe We Can Work This Whole Thing Out Together!... Nympho Seeking NSA in Annapolis I am Tory, a 24 year old, brunette living in the Annapolis area, 5'5, medium build, told that I'm fun, easy to be around, a good conversationalist and have a sexy relaxed vibe. Do you live here locally, find me attractive and love big playful titties? Then I mig...
  • Bi-curious and Want to Try it Out... Hi, I'm Gary, 42 years old, divorced, curious but cautious, well endowed, (I'm told) medium build, 5'10, 180 pounds, ex Navy and need to keep this discreet for now. If you live in Annapolis, are patient and know the in's and out's so to speak then I'd like to hear from you.  I don't know why I...
  • Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Annapolis and I got a BIG love gun to whip and pound you with until you scream! I'm def top and alpha and don't take no shit! Imma make you suck me first just for foreplay then I'll throw you back for some hard insertio...
  • 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...
  • Fit Swinging Couple in Annapolis, New to the Swingers Lifestyle & Ready to Explore! Swinging Couple in the Annapolis, Maryland Area Hello sexy people! We are a swinging couple in the Annapolis area. We are new to the swingers lifestyle but eager to learn and experience the passion! We assure we can give passion as well as we receive it! About Jeff Jeff is former military, stocky...
  • 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'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...
  • Annapolis Grandma Loves Breast Play! Hi ladies I'm Millie looking for a special woman in Annapolis. I need a lesbian to take me to heaven and play with my huge titties (bigger than my head) all night long! I'm kind of kinky, so maybe some torture, bondage, slapping and of course massage for the girls. Of course we can't forget about ki...
  • Young Female in Annapolis is Curious... Annapolis Bi-curious Babe I'm Darlene, 26 living here in Annapolis all my life and am finding myself bi-curious. I've always wondered what it must be like to be with a woman. I see women who are hot all the time and have certain sexual feelings for them, but I never acted on it. Except maybe a few ...
  • 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...
  • DON'T MASTURBATE ALONE! Let Me Get You Off! LET'S GO CAM-TO-CAM! Don't Masturbate Alone... Get Off With Me! Want to chat live cam to cam before you hook up? Talk about anything. Share your wildest fantasy! Ask me anything. Me and my girlfriends are home alone and we enjoy getting naughty on cam. Join My Cam Free! Avai...
  • Super Hot Barbie for Annapolis Male Hello!! My name is Phoebe and my intelligence and charming personality is sure to make you feel comfortable! I am just looking for a cool guy I can date around here and have some fun together! You want to meet me? Send me a message with your pics and number! @HotBarbieAnnapolis...
  • Nascar fan looking for lady to have fun with Nascar Fan for Lady in Annapolis If you are looking for someone legit, hit me up for a date. I am a down to earth guy who likes to chill on weekends and do fun stuff. I enjoy dining out, concerts, live theater, strolls at the park, hiking, movies, sports and much more. I hope you have a good sense ...
  • 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 ...
  • Sexy hung and big busted Hung and Busty Shemale in Annapolis Tammy, 39, big tits!! Well hung, everything works, clean and so cute!! What more could you want in a gurl?!! How about you message me @Tammy39T and we can talk and meet! Send your recent pic for mine. Username: @Tammy39TLocation: Annapolis, MarylandAge...
  • 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...
  • Mature Latvian lady seeking mature fun gentleman 🐈🐈 Mature Latvian Lady in Annapolis Hello there. I am Rada and I am a sexy mature woman from Latvia, now in Annapolis. I am very independent and charming and looking for a guy I can talk with and laugh with and just hang out with on weekends. Please contact me online or text....
  • 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...
  • 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...
  • TS Temptress Ready to Ruin You (In the Best Way) 😈💦 Annapolis  Hey lover 😘 I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...
  • 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 🅳🅸🆅�...
  • 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...
  • 🥵🍆SHEMALE COUPLE SEEKING SOMEONE FOR SEX🍆🥵 Hello men and women. We're a TRANS couple seeking someone or multiple sex partners to join us. We have cock and tits.. Does this turn you on? We're willing to let you hop in our bed, or we will come to your place. I really love sharing my partner and being fucked in front of her.. OMG I"M GETTING HA...
  • DIVORCED👩MOTHER-MILF?? I am available Every day. Make me CUM and this could be a regular thing. If you want test me in SLIM mom try today now anyone.100% real and legit 🚫NO GAMES 🚫TIME WASTERS 🚫NO DRAM Respect me and I will respect you! I just need some oral hookup all day/night .I can host or come to your p...
  • Dinner, Drinks… and You in the Driver’s Seat? 🍷💋🍑 Annapolis Hey there, lovely ladies of Annapolis! My name is Baily and I'm on the lookout for that special someone to light up my world. 💫Swap pics & contact info I may not be a prince charming, but I can promise you plenty of laughs, good times, and maybe even a little bit of romance along the way...
  • 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 ...
  • 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.  ...
  • Sexy and Flirty Terina Ready to Play 😘 Annapolis 💋 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. 😉Swap Pics & HMU @terina61947 ...
  • Annapolis - Let’s Make Some Mischief… And Maybe a Mess 😉  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...