The Complete List of Sissy Milestones: A Guide to Feminization and Sissification

Are you interested in exploring the world of sissification and feminization? Whether you’re a trainer, a trainee, or simply curious, this comprehensive list of sissy milestones is the perfect place to start. With 256 items separated into different categories, this guide will provide you with inspiration and ideas for your feminization journey.

Panties (20)

Panties are an essential part of any sissy’s wardrobe. Here are 20 milestones to help you build your collection:

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 (13)

Bras are another important aspect of feminization. Here are 13 milestones to help you build your bra collection:

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 (14)

Hosiery can add a feminine touch to any outfit. Here are 14 milestones:

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 (15)

Lingerie is a great way to feel feminine and sexy.

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 (15)

Shoes can make or break an outfit. Here are 15 milestones to help you build your shoe collection:

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 stilletos.
Own women’s flats.
Own platform heels.
Own Mary Janes.
Own women’s sneakers.
Own thigh-high boots.
Own lockeable heels.

Body Accessories (16)

Body accessories can enhance your feminine appearance.

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 (18)

Cosmetics can help you achieve a more feminine look. Here are 18 milestones to help you build your makeup collection:

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 (17)

Toys can help you explore your sexuality and enhance your pleasure. checkout These 17 milestones to help you build your toy collection

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. ( Checkout My Favourite Anal Beads)
Own an anal hook.
Own a tail plug.

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Lifestyle (23)

Lifestyle changes can help you embrace your femininity. Here are 23 milestones to help you make those changes:

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 (16)

Outfits can help you express your femininity. Here are 16 milestones to help you build your wardrobe:

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 (14)

Training can help you achieve your feminization goals. Here are 14 milestones to help you with your 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 (15)

Masturbation can help you explore your sexuality and enhance your pleasure. Here are 15 milestones to help you with your masturbation:

Masturbate in chastity.
Have a ruined orgasm.
Have a self-facial.
Eat your own cum.
Use a vibrator to masturbate.
Have a protate 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 (23)

Sex can be a fun and exciting part of your feminization journey. Here are 23 milestones to help you explore your sexuality:

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 (4)

Mental milestones can help you embrace your femininity. Here are 4 mental milestones to help you on your journey:

Give yourself a feminine name.
Write humiliating phrases on your body.
Keep a feminine diary.
Commit to a self-hypnosis schedule.

Cyber (9)

Cyber milestones can help you explore your femininity online. Here are 9 cyber milestones to help you on your journey:

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 (14)

Public milestones can help you embrace your femininity in public. Here are 14 public milestones to help you on your journey:

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 to a bar.
Go to a club.
Go to a party.
Go to a museum.
Go to a library.
Go to a park.
Go to a beach.

Social milestones can help you embrace your femininity in social situations. Here are 6 social milestones to help you on your journey:

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 (11)

Permanent milestones can help you achieve your feminization goals permanently. Here are 11 permanent milestones to help you on your journey:

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.

Conclusion

This comprehensive list of sissy milestones is the perfect guide for anyone interested in sissification and feminization. With 256 items separated into different categories, this guide will provide you with inspiration and ideas for your feminization journey. Whether you’re a beginner or an experienced sissy, there’s something for everyone on this list. So what are you waiting for? Start exploring your femininity today!

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