Sissy Milestones Checklist Sissification Milestone Tool The Complete List of Sissy Milestones Total Score: Panties Wear a pair of panties Own a pair of panties Own 10 pairs of panties Own 10 unique colors of panties Own 10 unique styles of panties Own a thong Own a g-string Own a bikini Own boyshorts Own ruffled panties Own hipsters Own cheeky panties Own pantaloons Own lacy panties Own panties with words on the bottom Own crotchless panties Own backless panties Own panties with a zipper Own pouch panties Own latex panties Bras Wear a bra Own a bra Own 5 bras Own a training bra Own a pushup bra Own a strapless bra Own a sports bra Own a bralette Own a T-shirt bra Own a lace cup bra Own a stick-on bra Own a bullet bra Own a matching bra set Hosiery Wear pantyhose Own a pair of pantyhose Own a pair of stockings Own a pair of knee highs Own a pair of ankle socks Own a pair of thigh highs Own fishnet stockings Own opaque tights Own white stockings Own patterned stockings Own leggings Own animal-print stockings Own lace-trimmed stockings Own 3 different deniers of hosiery Lingerie Own a garterbelt Own a fashion corset Own a steel-boned corset Own a petticoat Own a babydoll Own a panty-girdle Own a bodystocking Own a nightgown Own a teddy Own a chemise Own a bustier Own a camisole Own a peignoir Own a negligee Own a crinoline Shoes Wear a pair of heels Own a pair of women's shoes Own 5 pairs of women's shoes Own shoes with at least 3 inch heel Own shoes with at least 5 inch heel Own women's sandals Own women's booties Own high heeled wedges Own stilettos Own women's flats Own platform heels Own Mary Janes Own women's sneakers Own thigh-high boots Own lockable heels Body Accessories Make a pair of DIY breastforms Own breast forms Own a breast plate Own a chastity cage Own clip-on earrings Own earrings Own dangling earrings Own hoop earrings Pierce ears Pierce tongue Pierce nipples Pierce belly button Own fake nails Own hip pads Own a wig Own temporary tattoos Cosmetics Own Foundation Own Blush Own Lipstick Own Lipliner Own Eyeliner Own Mascara Own Eyeshadow Own Makeup remover Own Concealer Own Eyelash curlers Own Fake eyelashes Own Highlighter Own Bronzer Own makeup sponges Own makeup brushes Own eyebrow pencil Own a makeup holder Own setting spray Toys Own a butt plug Own butt plug training set Own vibrating plug Own a dildo Own a squirting dildo Own a ball gag Own a penis gag Own nipple clamps Own hobble chains Own arm/leg binders Own ballet heels Own fleshlight Own prostate massager Own a blindfold Own anal beads Own an anal hook Own a tail plug Lifestyle Own women's soap Own women's shampoo Own women's deodorant Own women's perfume Know women's clothing size (shoes, waist, hip, bust) Shave pubic hair Shave leg hair Shave arm hair Remove all body hair Reshape eyebrows Wear hair extensions Use home IPL hair removal Wear clear nail polish Wear colored finger nail polish Own colored toe nail polish Subscribe to a women's magazine Lose weight to become more feminine Grow out hair Pretend to have a menstrual cycle Throw out all male underwear Wear panties everyday Wear a bra everyday Wear women's hosiery everyday Outfits Own a maid outfit Own a sissy dress Own a school girl outfit Own a cheerleader outfit Own a secretary outfit Own a wedding dress Own a prom dress Own a little black dress Own a clubbing dress Own a bodycon dress Own a playboy bunny outfit Own a women's workout outfit Own a princess costume Own a gimp suit Own a women's cosplay costume Own a Stepford wife costume Training Remain in chastity for 1 week Remain in chastity for 1 month Remain in chastity for 1 year Wear a corset for 1-4 hours a day Wear a corset for 6-10 hours a day Wear butt plug for 1-4 hours Wear a butt plug for 4-8 hours Fit a small dildo anally Fit a medium dildo anally Fit a large dildo anally Fit a small dildo orally Fit a medium dildo orally Fit a large dildo orally Practice applying makeup Masturbation Masturbate in chastity Have a ruined orgasm Have a self-facial Eat your own cum Use a vibrator to masturbate Have a prostate orgasm Use a mechanical sex machine Watch sissy/feminization hypno Finger your anus Moan while masturbating Use an anal douche Have an anal enema Gape your ass Masturbate by stimulating your nipples Perform auto-fellatio Sex Experience a facial Get pegged Have a threesome Have anal sex Receive a creampie Give a blowjob Swallow someone else's cum Respond to a booty call Have anal sex immediately in the morning Have anal sex more than 4 times in one day Have anal sex while in chastity Have sex while dressed as a woman Get spitroasted Service a gloryhole Have an orgasm from anal sex Have anal sex without orgasming Experience a bukakke Participate in an orgy Participate in a gangbang as the center Have anal sex in 4 unique positions Deepthroat a penis Get spanked during sex Have anal sex without a condom Mental Give yourself a feminine name Write humiliating phrases on your body Keep a feminine diary Commit to a self-hypnosis schedule Cyber Have an online profile for your female persona Use a videochat service (Omegle/Chatroulette) as a woman Post pictures of yourself online dressed as a woman Post videos of yourself online dressed as a woman Have a female image of yourself captioned Receive a cum tribute toward your female persona Participate in online feminization training Complete online feminization tasks Receive a feminizing gift from someone Public Go for a walk in public Go to a shopping mall Go to a beauty/hair/nail salon Go to a restaurant Go out on a date Go to a lingerie shop Go to a movie theatre Go out fully dressed as a woman Go for a walk in public wearing female underwear Go to a shopping mall in full female attire Go to a beauty/hair/nail salon in full female attire Go to a restaurant fully dressed as a woman Go to a lingerie shop in full female attire Go to a movie theatre fully dressed as a woman Social Tell a friend you are interested in feminization Tell your significant other you are interested in feminization Be in a relationship where you spend a majority of your time in your female persona Book a session with a professional dominant Have a circle of friends where they primarily know you as your female persona Live as your female persona for 2 weeks Permanent Receive breast implants Receive butt implants Get a feminization themed tattoo Microblade your eyebrows Get lip brushing surgery Get a prince albert piercing Get tattooed eyeliner Get collage injections Take female hormones Have facial feminization surgery Have an orchiectomy Calculate Score Your Feminization Level: