#sissy maid training

[dollmaidcrystal]

Looking back at the 2022 Kinky Resolutions

Before we write 2023’s Kinky Resolutions, we’re going to look back at 2022’s list to see how we did.

Ugh. End of year reviews. Industry standard raise plus an extra percent. Done.

As always, Mistress Aspyce’s commentary is in italics.

Aspyce Gets into Shape

Ugh. Just… urrrggh.

I’d call it a success.

Losing 4 pounds is not a success. It’s depressing.

You had to give away a bunch of corsets that slide off you now.

Depressing and expensive!

Last year, your physical rehab barely had you walking without a cane. Now you’re at the gym 3 days a week and can run the scenes you were physically incapable of.

I don’t feel handicapped anymore, but I want to like my body again. I’ll lose this stomach if it kills me!

Crystal Improves Her Posture

Another resolution in the win column! Thanks to my new exercise routine, I can now stay at attention through evening service. Plus, I made strides in hoof boots AND ballet boots. (Pun totally intended.)

You don’t look like you’re developing scoliosis anymore, but…

It. Goes. In. The. Win. Column.

New Latex for Aspyce

Oops.

Wow. You went a full year without buying new rubber?

Nothing jumped out at me. When I did have time to go kink shopping, I was looking for replacement corsets, not latex.

You could still make good on your resolution if we start shopping now.

It is hot cocoa season. Do you know where I can get a…

LATEX SNUGGIES ARE A HARD LIMIT.

New Day Uniforms for Crystal

Oops.

How have you not worn holes in your old uniforms?

I mostly stopped using them.

Bad doll maid! You’re supposed to be a latex maid. In latex!

Mistress, you adopted a puppy last year. For the first half of the year, I worked wearing a catsuit under sweats so I could take him out at a moment’s notice. Then the COVID shutdown of Shenzhen happened, and the pipeline for cheap latex has been clogged since.

You’re still getting spankings for this. Now that Nonsense is older, you’re to be in uniform while working.

A Doll Display Box – FINALLY

Failure for three years in a row. How are we so bad at this?

I’m going to unfairly blame the dog. This is all your fault, Nonsense. And something something China, too.

Gord-style Scenes

We did that! We even had one where you were a pumpkin!

Custom built bondage devices, tight corsets, catsuits, vacbeds, pony training on a treadmill. Another win goes on the board!

The Gord-inspired scenes were fun to do! We should do more in the new year.

Enjoy Ourselves More

This was the main one, and it was a big ol’ success. We started traveling again.

You got featured in the Montreal Gazette. We’re officially international fetish icons!

Munches came back.

I found puppy-friendly wine tasting rooms.

I ran in my first ponygirl race. I won my first ponygirl race!

We went to the Sybian Joust championships.

The kinky Superbowl party.

The femdom Halloween party.

I got to be a pony. And a kitty. And a cow. And a pumpkin.

The sissies got to see Mozart’s most famous forced feminzation scene.

We got to meet some of our Fetlife friends!

And we have Nonsense. You can’t tell me that dog doesn’t make you smile.

2022 was a good year.

Good job, Year!

[goddesslovescosplay]

Still accepting and training sissy maids

[worldtosubmissive]

YOU SHOULD EXPECT

1) Discipline and Attention training

2) Slave rules and Positions training

3) Submission Training

4) Slave Contract

Sissy/slave/trans/household maid 😈😈

[sissy-tyler]

Mommy’s Blog #231: “Maid Days”

Wednesdays are always Maid Day for my widdle, sissy Tina. On Maid Days, Tina trades in her adorable baby dresses for a cute maid outfit and sets to work cleaning the whole house for me. She’s still diapered, of course, we can’t have Tina forgetting who wears the pants in the house (that she cleans), but she is expected to act much less like a little baby, and much more like a sweet, widdle servant.

When turning your husband/fiancé/boyfriend into a sissy, I can’t stress enough how important sissy-hypno tapes are. Not only do they keep your man cute and behaved; many of them also keep your sissy having the most adorable mannerisms. As you can see, whenever Tina stands still she can’t help but sway her hips and watch her widdle dress dance.

It’s making your sissy uncontrollably perform mannerisms like this, that lets them know you hold all the power. Well, the mannerisms and the chastity of course. In one of my upcoming blogs I’ll actually share which hypno tapes I used to train Tina to LOVE her chastity. She actually hates being out of it and begs me to keep her in only the smallest, girliest cages.

I’m also thinking of starting an OnlyFans for Tina! Me and a couple of the mommies of Tina’s sissy friends have thought it could be quite lucrative to have our sissies whoring themselves out online, I guess there’s a pretty big market for it!

Anyways, thank you so much, as always, for joining in on Tina and I’s blog. It’s been so fun documenting Tina’s journey from “big, stwong man” to “helpwess, widdle sissy”. Tina always loves reading the degrading comments that get left for her. But, until next time, keep your sissies diapered, caged, and ready to serve!

Find more, exclusive captions on my Patreon!

[sissyfaggotwhiteboi]

Guide for Black Doms to make white sissy

Found this Guide on another unrelated site;  it describes how to make white bois into sissies for use by Superior Black Masters, and would willingly submit to have this done to me!

This is a guide for Superior Black Men that want to usurp their rights over crossdressing white boys. I will tell you the weaknesses and inner desires of white boys, so that you may more easily enslave and own them. If you want an obedient and addicted white boy, read on.

Submissive WHITE Sissy Faggots Are Eager To Serve As Sissy Maids And Cum Receptacles For SUPERIOR BLACK MEN –  REGISTER HERE TO BE USED BY A SUPERIOR BLACK GOD

1) Getting a real meeting with a boy is the most crucial part of beginning the white boy emasculation.

The rest comes easy and naturally for the sissy boy. Most fantasize about being forced into it. They like the risks and are completely aware that it is a slippery slope. Blackmail and Domination is part of what they want. On some level, they want and feel they deserve to lose their identity as a man and to serve Superior Men. More than anything in the world. Any kind of resistance is just part of what the fantasy; white sissy boys have a desire to be freed from their choice. Younger and not married are more desirable.

Submissive WHITE Sissy Faggots Are Eager To Serve As Sissy Maids And Cum Receptacles For SUPERIOR BLACK MEN –  REGISTER HERE TO BE USED BY A SUPERIOR BLACK GOD

Degrade and humiliate him in your emails. Ask him how small his little pee pee is. Tell him how you will slap his face with Your Superior Cock. You will put him on a leash. Sissy ’s like to hear confirmation they are not real men. Call them a girl. Tell him he has a girly ass. Or if he is skinny, call him petite and effeminate. Ask him if he likes looking at a picture of Your Cock. Give him a female name as a reminder. On the reverse, make him call you Daddy (this is the absolute most humiliating name you can use, but Sir or Master work well too). If he doesn’t, tell him you will punish him. Try and get a phone number or address before he can back out. Always push to meet sooner.

2) Establishing follow up sessions. This is where most sissy boys get away. My greatest advice here is to ask the sissy if you can record and take pictures of him for your personal collection. In the moment, they will tend to say yes and do it. A simple picture of him on his knees sucking your cock could well be the key to his entire enslavement. You only need suggestively say you like the picture and want to send it to his friends if he is reluctant to meet. Record him every time after.

Submissive WHITE Sissy Faggots Are Eager To Serve As Sissy Maids And Cum Receptacles For SUPERIOR BLACK MEN –  REGISTER HERE TO BE USED BY A SUPERIOR BLACK GOD

Chastity is another way. This is better long term and for training. Just like other males, white sissy faggots have that moment of wake-up and sometimes regret when they finally cum. They will do anything before that moment, but can feel like they went to far once cum. Not allowing them to cum will keep them submissive, turned on, and obedient. You can do whatever you want for however long you want. They on some level, even like the denial. They feel trapped and needy to be nice to you.

If they are resistant to this initially, you can keep pushing it, and just put it on them if you can convince them to be tied up. Forgiveness over permission. Use a device that cannot be removed without a key.

During the first meeting, make them cum, be verbal, make them tell you what a bitch they are. Make them promise they will be your sextoym. Make them give you their word they will suck you next week.

3) Training will transform the white sissy into a total, obedient slut. You should not let them cum more than once a week. Suggest tying them up when you let them cum and you take off the device, so they have no say if it comes back on. Prolonging how long they cum will make it more intense and they will have much less chance of regret. You can anally train them to cum without stimulation from their little white penis and eventually to cum without being hard. Google sissy gasm. Teasing around their butt with your fingers will help. The goal is to have them only cum from anal stimulation. If you have to, make them wait another week if they can’t do it without touching their tiny pee pee. Stroke them from behind like a bitch so their cock is pulled behind their legs. If they’re really are unable to cum after two weeks. Also suggest stroking like this the first time you meet them until they cum.

Submissive WHITE Sissy Faggots Are Eager To Serve As Sissy Maids And Cum Receptacles For SUPERIOR BLACK MEN –  REGISTER HERE TO BE USED BY A SUPERIOR BLACK GOD

4) After some time, you may introduce more changes to the white sissy. Changes that cross the “point of no return” will keep a white boy as a sissy longer than anything else. They may resist to these ideas, but you can keep pushing it on them, and on some level they want it more than anything in the world. Ultimately, it is their choice.

Shaving smooth will make a huge difference in how girly the sissy looks. If you are keeping the sissy shaved,, You could eventually encourage the sissy to get laser hair removal.

Another suggestion would be a tramp stamp or other tattoos. Perhaps “sissy slut”, “Emily”, “BBC Owned”. You could have her do a trial with a Henna tattoo or just go all the way. Permanent makeup is another humiliating way to feminize the white sissy.

The final step is the one white sissy boys think about the most. They feel it is their destiny and that is a final step to submitting and giving up their ego for humiliation. Hormones. Two types, anti-androgen and estrogen. Estrogen will have the most effects, such as face breasts, and submissive tendency. Anti androgen will make them more petite, less muscle, and make their tiny pee pees even smaller. You can find more online about it. Whatever you want of them, tell them they need to look pretty and pleasurable for Men. And that they are better off this way. Affirm it is who they are on the inside.

5) Enslaving the sissy is the goal. Establish Dominance and always push the little white boys to say they are inferior. Treat them like a sextoy. Text them you want blowjobs on random days. White sissies should be your on-call fuck toy. Punish them when they are bad. Use chastity to control their rewards. You can do whatever you like, turn them into a live-in maid if you like or a discreet obedient sex slave.

Submissive WHITE Sissy Faggots Are Eager To Serve As Sissy Maids And Cum Receptacles For SUPERIOR BLACK MEN –  REGISTER HERE TO BE USED BY A SUPERIOR BLACK GOD

[starsandhughes]

How did sissy and Trevor find out about the twins?? And how did they tell their families?

sissy has had a pregnancy scare before a few years back, but this time around she actively was feeling symptoms. so when she was almost a week late, she decided to take a test

she took so many because she could not believe it, and after each one she got happier and happier!

she knew she wanted to tell her and Trevor's families in a really special way, so she couldn't do it over the phone. she also wanted to put something cute together to tell Trevkr, and he was at a rink anyways, but she was BURSTING to tell somebody

so what does she do? she called Taryn Tkachuk, one of her only girl friends, her maid of honor (yes, Cole is her man of honor, but Taryn will be the maid) and somewhat like a little sister to her.

Taryn SCREAMED when she answered the facetime and saw (one of) a positive pregnancy tests on the bathroom counter! and just like Sissy, she got more and more excited when sissy told her that she had four more positive ones. they immediately started planning how to tell Trevor and their families. Sissy had to quickly tell Trevor hello (and had him wave to Taryn) and that she loves him when he came home before running off to their bedroom and locking the door for "girl time."

Sissy and Taryn spent almost an hour on pinterest and tik tok and articles for ideas of how to tell your husband (fiancé in Sissy's case) that you're pregnant, but she didn't want to do anything too basic. Taryn eventually found a picture of something not too basic with the perfect touch of Sissy's humor:

Sissy told Trevor that she was going to pick up some snacks for the house and left at the same time that he was heading to the gym. she did do that, but she also picked up a mini chalkboard and some chalk since they already had a baby yoda.

she was sitting on top of their kitchen island right next to her set up when he came home. Trevor noticed it immediately and picked her up off the counter, spinning her around in a hug. she didn't even notice that Jamie (who happened to be in california with them at the time before he went back to toronto) was behind him, but she was really glad that he was because he was smart enough to remember how much she loves pictures of everything and he was able to take some pictures of them.

"we're gonna be parents," Trevor said with the biggest smile, cupping her face with both hands and smashing his lips onto hers.

"we're gonna be parents!" she echoed.

---

as for their families and friends, they had lucked out that training camps (for those signed) hadn't started yet, so she was able to get all of her friends and family in one place at the same time. they would fly to Trevor's home town to see his family next.

they're big on game nights, and Sissy had convinced all of them to play pictionary. she waited a couple rounds before she decided to tell them. her plan involved pieces being put together, but she knew that at least her mom, Ellen, would be able to put it together for the rest of them.

"it's a friends episode title!" she announced to the room.

the minute timer had started and Sissy began to draw terrible sketches of Rachel in a hospital bed, Ross in a different hospital bed with his legs in the stirrups, and then all six of the friends gathered around Rachel and her baby.

Sissy kept writing even after Alex had yelled "THE ONE WHERE RACHEL HAS A BABY" for the fourth time. over Rachel she wrote an 's,' over Ross she wrote a 't,' she wrote a q, j, l and a c over the remaining friends, and added in an extra stick figure to write an 'a' on top of them.

she turned when she finished, facing the group with her hands linked in front of her as if she was a school girl waiting for her good job prize.

it was Luke that connected the dots the quickest. everyone else quickly followed after he breathed out a surprised "holy shit!"

Luke got off the couch and ran to her, hugging her tightly before stepping back as his hands trailed down his sister's arms and took her hands in his, "I'm gonna be an uncle?"

"Yeah, Lukey Moosey, you are," she said.

Ellen started crying, and even Jim looked like he was tearing up.

"you're— you— and him—" Jack couldn't get out a full sentence he was so excited and shocked. All she could do is nod at him with the biggest smile on her face.

Jack and Quinn ran over to Sissy and got on either side of her, both hugging her as tight as Luke did, and brought Luke back into the hug.

"Dibs on being their godfather!" Cole exclaimed as he took his window to hug Sissy.

"You can't do that!" Alex shouted. "Z and Girly Hughes decide who's the baby's godfather! And I've known Z the longest!"

"Don't pull that card, man!" Trevor laughed. "There's a lot of people that we have to consider!"

Sissy stepped away from her brothers, her friends, and Trevor to go over to her real parents. The ones that took her in. The ones that taught her everything.

"I don't know anything about babies," she half heartedly laughed to cover up the slight fear that was creeping into her excitement as she hugged them.

"We know enough," Ellen assured her. "And I know you, and I know that you're going to be an amazing mom."

"I learned from the best."

[prissytutu]

Maybe her obedience training had gone a bit too far…he really believed he was her sissy maid now. Oh well!

[sissy-tyler]

Hello, mommies, and welcome back to another episode of our “Sissy Re-education and Training” series, brought to you by the Sissy-corp! I’m your resident mommy, Yvonne, and the lovely girl next to me is Little Sissy Tiffany. Say “hello” little Tiffy.

“Hewwo evwybody!”

Little Tiffy is in our care at the Sissy-corp facilities because she just couldn’t make it as a man, or as a loving husband. Infidelity; being rude to his wife; always leaving messes for her to clean up; expecting her to cook every meal for him; the list goes on. He was much less of a man, and much more-so an overgrown baby. So he, or should I say, SHE’S been enrolled in our sissy-maid program.

In this program Tiffy’s been learning how to cook, clean, serve, and effectively pleasure her former wife, now mommy, and any lovers her mommy chooses to have. More importantly, though, Little Tiffy has been learning the ins-and-outs of how to be the bestest, widdle, baby gurwl a mommy could ever ask for! Isn’t that wight, widdle Tiffy?

“I wuv being a good gurwl fow my mommy!”

God, she’s just too adorable. Our training session today is about how to effectively reward your sissy while reinforcing her baby-ish behavior. Tiffany, here, was without a doubt one of our hardest cases to break, thus far, especially when it came to making her use her diapers. But, thanks to our patented “Rewards and Reinforcement” program. Even a stickler, sissy like Tiffany can be turned into the most dutiful, diaper dumper.

When rewarding your sissy, you first want to start off with a reward routine. For Tiffany, we had her on a schedule of getting a reward every 5 messy diapers she made. We kept her on this routine for three weeks, then the fourth week we changed her routine to a reward every 10 messy diapers. Week number 5; we upped it to every 15, then on week 6, every 20. After week 6, her rewards were then shifted to mommy’s discretion, meaning her rewards were completely randomized. This kept Tiffany always wanting to fill her diapers in hopes of the next reward. Tiffy, how many messy diapers have you made since your last reward?

“One….One hundwed and twendy nine.”

Such a good girl, Tiffy, I’m amazed you can even count that high! Now, even though Tiffany’s reward system may seem a little extreme, we do recommend you keep your sissies on very similar regiments. Now, onto how you properly reward your sissy.

To properly reward your sissy, you’ll want to make sure she’s in her Official, “Sissy-corp clitty cage”, and has some form of a buttplug in, the larger, the better. Then, before you’ve put your sissy in her diaper, you’ll want to make sure you’ve attached the electrodes of your “Sissy-Corp Rewards Device” to both her cage and her booty-plug.

Before I start the machine I always love making my sissies get on their hands and knees. I feel it really enforces that submissive mentality, but you can put your sissy in whatever position you feel is best. Then, I start the machine in 3…2…1….aaaaand watch how quickly Tiffany melts!

“UNGH! MOMMY! UNGH! IT FEEWS SO GOOOOOOOOOD!”

Now, at this point, I love grabbing and pulling Tiffany’s hair. Her wife told me she always used to be too rough in the bedroom, so I love returning the favor. Always remember to make your sissy tell you why they’re getting rewarded! Tiffy, why are you getting buzzies today?

“Ungh! B-because I made poopies in my diapuurr wike a g-g-good widdle guuurrll!”

You always wanna make sure you’re reinforcing to your sissy WHY they are getting to make spurties in their diapies. Always remind them, as well, that they are getting to make rewardies INSIDE of their diaper, just like the little baby they are. Speaking of rewardies, Tiffany is due to blow any second here!

“UNGH! MOMMY I MAKING GOO GOO’S! It feews so so goooood!”

Wow, Tiffany, I think that was 45 seconds, a new record for you! I forgot to mention, little Tiffy, here, is also a premature ejaculator. Once again, I’d like to thank you so much for tuning into our Sissy-Corp training session, and I look forward to seeing you again when we show you how to dress your sissy for going out in public. Tiffy has an upcoming date with her mommy to go see….

“Da new Bawbie Movie!”

Find more, exclusive captions at my Patreon!

[dollmaidcrystal]

Ways Our Lifestyle Doesn't Match Sissy Tropes

I don't want to be a girl. I don't want to go back to being a boy either. Gender binaries are stupid, and I don't care as long as I get to be pretty.

Mistress isn't particularly sadistic to her sissies. Her goal is to be able to lounge in luxury while a staff of beautiful, devoted sissies take care of her every whim. She can't have that unless she takes the time to turn a trainee into a beautiful doll first.

I'm not a tiny, cute twink. I'm too tall and too old to fit that stereotype anymore.

Mistress does not like sissies in chastity. Why would she put so much effort into training sissy sex slaves if she wasn't a fan of sissy cock?

I don't get any thrill from being cuckolded, shameful or otherwise. All I want is for Mistress to be happy, and if she enjoys having a sidepiece, so be it.

Mistress does get jealous every time she loans a sissy out, and frets constantly about if they'll be back. She still does it because it's an extremely effective form of training.

Neither of us get instantly horny from wearing latex. We wear rubber constantly around the house, so we feel at home in rubber more than anything else.

Mistress does invite other femdoms over for parties where they're served by sissy maids. These very rarely end in any kind of orgy. Usually, the parties consist of a couch full of drunken dommes watching Disney+, while the maids handle snacks.

[sissy-maid-jasmine]

Some users have asked me why my clitty isnt locked when im wearing my shiny pink sissy maids uniform with open crotch. Its not by choice!I really want to lock it tightly in a tiny cage, but my gf forbids me to do it. She thinks it would be much more uncomfortable for me to not be locked up when dressed up in my shiny pink maids uniform. And she was right! I had to do all the chores in the house and pleasr my girlfriend whenever she called for me. But i wasnt allowed to ever touch my clitty or any region between my legs...

It felt supersubmissive to have to serve and please without being locked, especially when touching my clitty balls or butt meant instant punishment..

When she called for me to lick her on the bed, i accidentally touched her leg with my clitty. It felt so good to touch a womans body with my clitty, but i knew i was in big trouble... She told me to get on my hands and knees, after which she went to get a humbler. She grabbed my balls and clitty v... ery violently, squeezing her nails in my flesh. Then she let go of my clitty and pulled hard on my balls. While i was squirming into the matress, she put my balls in the humbler and screwed it super tight. And she she made me get of the bed.

I carefully moved myself of the bed without pulling to hard on my balls. When i was on all fours on the ground, she tiewrapped each one of my anklecuffs to each side of the humbler! It hurt so bad to keep my balance on my knees and hands...

She laughed at me and told me to remember that my cock is her cock. And that im never allowed to touch it when she is in control. She explained that she really enjoys a real dick in her pussy. And that my clitty will be trained to only please her. And that i am just a convenient way of getting her a real dick.

Im getting better at thinking of my clitty as hers. It feels super humiliating to be commanded to fuck her in my pink sissy maids uniform. She makes me hard by making me worship her ass. She shows me her butt and wants me to imagine that i am allowed to thrust my tongue in her asshole. Its so humiliating that i get hard instantly, afterwhich she gets to have her hard cock where ever she puts it. Slowly i am getting better at not enjoying the penetration at all, as it isnt for my pleasure.

Slowly im embrasing it as the ultimate sexual abuse...

[nekotaylor]

The Complete List of Sissy Milestones

link

Categories

Panties [/20]

Bras [/13]

Hosiery [/14]

Lingerie [/15]

Shoes [/15]

Body Accessories [/16]

Cosmetics [/18]

Toys [/17]

Lifestyle [/23]

Outfits [/16]

Training [/14]

Masturbation [/15]

Sex [/23]

Mental [/4]

Cyber [/9]

Public [/14]

Social [/6]

Permanent [/11]

Total [/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.

[crybabytoy59]

A window in time…..pt6.

Naughty crybabies do not Ever swear In front of her caregivers ! 

Thwack !

Thwack !!….

My rear was on fire as the both paddled my bare bottom relentlessly as I squealed into my wet pissy gagging… 

Suddenly they stopped as I strained in the Punishment bench, Auntie Lottie rubbed my stinging rear as she spoke..

“Are you sorry Crybaby? (I nodded rapidly £ Well am sure you are but lest just make sure little one !”

I heard the ripping of tape as Nanny pulled my right belt marked rear out to the side, followed by Auntie taping the skin out wide ! 

My left cheek got the same treatment as Auntie Lottie patted my fuck hole now stretched open wide ! 

She lifted a small rubber flogger then whipped my hole ! 

Over and over she whipped me there using various items she finished with a small bendy steel rod ! 

This was amazingly painful and I started crying again openly in front of them both ! 

Nanny had lifted my headie as I was given my punishment to talk to me..

“Clever Baby crying is a part of your journey into babyhood towards us princess, so Nanny help you as Auntie Lottie puts your new special pluggie up that naughty ass of yours !”

She took my center panel of the maids dress down as it had a zipper around the frilly chest heart… Nanny took my nipples teasing them …

“ You’re such a clever girlie crying these lovely tears for us… Infact they are so cute let’s have lot and lots of them !”

Nanny lifted a syringe with white fluid in it !…

The needle looked quite thick and was around 3” long  ! 

“Look at Nanny !”

She pulled my nipple away painfully from my body the skin now taught Nanny pushed the whole needle into my skin behind my nipple then pushed the contents slowly into my chest ! 

The nipping pain was instant as I renewed my struggle in the punishment bench ! 

Auntie Lottie laughed “Have you hit gold Nanny !”

Auntie Lottie put a finger each side of my Fuck hole then pushed the large black intruder slowly home to more struggling from the bondage bench ! 

As Nanny pulled on the other nipple she counted 1….2….3 in we go ! 

They both pushe at the same time as I nearly passed out ! 

They both clapped as I slumped bawling my eyes out ! 

Auntie Lottie pushed the Center of the rubber plug as the four inner “Wings parted  holding the plug firmly home ! 

“Clever Crybaby are you ever going to use naughty language In front of us again….

The room filled with my genuine wish to serve them both as an Obedient little toddler void of any Big thoughts or words”

I had waited Years to be in this space and genuinely wanted nothing else in life at that moment in time but to bawl my eyes out ..

Few would understand what had just happened in their Dominant care outside.

But here strapped tightly to the punishment bench they both knew the gift that was being exchanged….

“I do hope so Crybaby… now Nanny and I have a nice gift for you princess  !”

Auntie Lottie  held up a training bra ! ! 

It was lined with lots of little rubber nipples! 

That would constantly tease my now Very sensitive nipples due to Nanny’s injections…

They tugged this onto me as the tight pink rubber training bra pushed out from my sissy chest !

Auntie Lottie zipped up the pink frilly chest panel I found this was stretchy, with my new little titties poking out from the frilly chest line …

Again Nanny took pictures…as Auntie got another item a large cotton bud ? ….

“Can you hold her cute headie Nanny nice and tightly please…as someone is going to want to struggle!”

She had a wee jar that she was rolling each end of the bud in ?

Lifting a steel nose hook she removed the rebreather mask, then fed the rubber laces to my face harness pulling them down Auntie pushed the hook up my nostrils wedging them up like a baby piglet ! 

“Ok here we go Crybaby take lovely Deep breaths six in total ! Then hold your breath !”..

At six I held my breath as Auntie Lottie coated inside each nostril pinching my nose to ensure the green slime spread evenly…

They both stood back to watch the spectacle unfold !! 

I pulled at my bonds trying not to breath as it stung my nasal passages! My eyes instantly started streaming as my mouth watered profusely and I choked on the mustard fumes ! … 

Nanny was taking more pictures…

“Now that’s much better Tears Crybaby  ! Look at you being the perfect Potty Toy !”…

[sissybetawimp7]

Oh Daddy, after 3 months of chastity you’re ready to do anything I say? Well for starters you can hang a Black Lives Matter flag on our front porch. Then I’m gonna call my black boyfriend to come over with his friends from the football team to run a train on me. You will greet them with respect and a smile in your sissy maid outfit. We’re gonna be so progressive in this house and neighborhood!!

[maidsidney]

hi there! just came across your blog and it really speaks to me. i'm very excited to see that there is another sissy like me who is dedicated to proper maid training and lifestyle. i was wondering if you had any advice for someone who wanted to gently nudge their partner/wife/husband towards this sort of relationship/agreement (to the point where it's more of an employer/employee relationship)

Hello and thank you for your kind words, I am happy that you enjoy my blog. In response to your question I will tell you my first marrage ended in disaster and one of the reasons was gentle nudges towards crossdressing, BDSM, and other suchs interest. My advice is that you simply sit your partner down and tell them what you want. Theuy will either understand or they won't. If they don't, move on and go find what you are looking for and be up front about it going in. For a sissy that is a hard road that may lead to lonelyness. Be careful what you wish for as the reality of being a sissy maid is mush differant than the fantasy and is more sacrifice than satisfaction. If you are married or in a relationstion that you want to move in this direction always remember that the superior also makes a huge sacriface. They sacrifice a the traditional relationship they thought they were in and the relationship they always wanted. Ownin a sissy maid does not replace those things and if those things are still wanted they will eventually seek them. When that happens they will either leave you or you as the maid will be forced to watch from the sidelines as you serve. The romantice feeling you have for your superior do not go away when you become thier sissy maid.