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6
Tracking my milestones:
Post Body

The Complete List of Sissy Milestones

Hello, here is my comprehensive list of sissy/feminization milestones. These milestones can also be interpreted as individual tasks or assignments for trainers/trainees to follow for inspiration. The goals are separated into different categories. There is a total of 256 items in this post. How many have you done? You can share your category breakdown by copy and pasting the table of contents.

I'd be interested to see how people compare and comment if you have any suggestions for things to add.

Categories

  • Panties [13/20]
  • Bras [5/13]
  • Hosiery [10/14]
  • Lingerie [3/15]
  • Shoes [6/15]
  • Body Accessories [3/16]
  • Cosmetics [0/18]
  • Toys [8/17]
  • Lifestyle [5/23]
  • Outfits [2/16]
  • Training [7/14]
  • Masturbation [13/15]
  • Sex [0/23]
  • Mental [3/4]
  • Cyber [4/9]
  • Public [5/14]
  • Social [0/6]
  • Permanent [0/11]
  • Total [77/256]

Panties [20]

✅- 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]

✅- 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]

✅- 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]

✅- 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]

✅- 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]

  • 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]

  • 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]

✅- 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 [23]

  • 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]

✅- 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]

✅- 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]

✅- 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]

  • 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]

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

Cyber [9]

✅- 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 tasks can be done twice, once while with female underwear and once while fully dressed as a woman.

✅- 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.

Social [6]

  • 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]

  • 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.

Two people with the same score may have very different point breakdowns. That makes it very difficult to accurately describe what kind of sissy a person might be based on their point totals. But I did it anyway just for fun.

Scoring

  • 0-30 : Beginner.
  • 30-60 : Feeling Girly.
  • 60-90 : Exploring Femininity.
  • 90-120 : Crossdresser.
  • 120-150 : Getting Kinky With it.
  • 150-180 : Loud and Proud.
  • 180-210 : Full-Blown Female Persona.
  • 210-240 : Practically Female.
  • 256 - Permanent Sissy

Bonus Achievements

  • Completionist : Complete all tasks in any category.
  • Lingerie Lover : Own all items in Panties, Bras, and Lingerie categories.
  • Fashionista : Own all items in Outfits and Shoes categories.
  • Female Training : Complete all tasks in Lifestyle and Training categories.
  • Sex Positive : Complete all tasks in Masturbation and Sex categories.
  • Experimentalist : Have at least one task completed in every single category.
  • Attention Whore : Complete all tasks in Cyber, Public, and Social categories.

Author
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Account Age
1 year
Verified Email
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Total Karma
709
Link Karma
664
Comment Karma
45
Profile updated: 3 days ago
Posts updated: 23 hours ago

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Posted
3 months ago