Day 3 – Diapers Diapers And More Diapers

I don’t have a big update today due to my busy schedule. I went through three diapers today and flooded the one I wore to work on the drive home! I’m just glad it didn’t happen a few minutes earlier!

I have already come to love the naughty feeling of relieving myself while at work. I wonder what my coworkers would think if they knew about the dirty little secret under the professional facade I show at work…

For bedtime I’m wearing another Little For Big onesie with cute animal prints and white tights for the cute and innocent looking baby. Onesies really are a lifesaver to keep a diaper from sagging and getting unruly.


Day 1 In Diapers With The Isabella Sissy Dress

Hello! So far my first day wearing diapers has gone without a hitch. I’m currently on my second diaper for the day after drinking quite a lot this morning.

After getting myself cleaned up this morning I was told to wear the Isabella Sissy Dress you see in the pictures below. This dress is accompanied by a petticoat, pinafore, five inch heels, pink gloves, a plastic diaper cover with bows and jingling bells, and white tights! The dress and heels have been locked on with adorable silver heart locks to prevent me from removing them until Mistress says so.

The bells on the diaper cover ensure I cannot sneak up on Mistress and announce every move I make. She says it’s so she can know where her little girl is at all times.

I’ll Be Spending A Full Week In Diapers

Starting Saturday, February 2nd at 8 AM I will begin spending a full seven days, or more, in diapers.  It’s a fantasy I have wanted to try for quite some time now, and after building up the courage to ask it’s finally going to happen! 

I have been fortunate to have a girlfriend, who is also my Mistress when she wants to be, that is incredibly compassionate and understanding when it comes to the lifestyle I wish to indulge in.  When I asked her if she would help me live out a fantasy of mine to wear diapers for a week she happily agreed to help.

Before starting, we put together a list of agreed upon rules I would follow.

Sissy Sasha shall follow the agreed upon rules below:

  1. Sissy Sasha will wear diapers for no less than seven days.  Mistress will decide when Sissy Sasha can use the big girl toilet again.
  2. Must obey Mistress at all times
  3.  Refer to her Mistress as Mami
  4.  Prohibited from using toilet to pee.  My diaper is my toilet.
  5. Prohibited from touching my diaper unless permission is given
  6. Prohibited from masturbating in any way, shape, or form
  7. Diaper is never to be removed without permission
  8. Is not allowed to ask to be changed or to complain about the state of my diaper.  Mistress decides when I need a diaper change.
  9. If a pacifier is put in my mouth I am not allowed to remove it or speak.
  10. Required to ask to go number two.  Diaper must be replaced immediately after. If request is denied it must be held or use diaper
  11. All electronics use will be monitored.  Mistress can prohibit use at any time for as long as she wishes
  12. While at home pants, shorts or anything that covers my diaper, unless instructed otherwise, is prohibited. I must change out of “grown-up costume” as soon as I’m through the door. Baby/child/sissy clothes such as plastic pants, onesies, shortalls, footed pajamas, dresses, etc. are allowed.
  13. I must confess to any broken rules immediately.  Failure to do so will result in strict and severe punishment
  14. After 9 pm I may only crawl while at home.  Walking is forbidden.


  1. Enema
  2. Laxative
  3. Suppositories
  4. Castor oil
  5. Butt plug
  6. Chastity
  7. Spanking
  8. Required to go number two in diaper
  9. Must only wear diaper.  All other clothing prohibited.
  10. Double+ diaper and remain unchanged for long length of time
  11. Must drink from bottle and only allowed formula/ensure
  12. Kneel in corner with nose touching floor and padded butt in air
  13. Only allowed to drink from a baby bottle and eat baby food until Mistress decides otherwise
  14. Write out sentence multiple times.  Example: I’m sorry I was a bad baby
  15. Wear an outfit and are not allowed to change or adjust it in any way without permission
  16. Must say out loud and intelligibly when I need to use my diaper, even in public. Regular checks will be performed, any unannounced wetting will be punished.

Because I work in an office I am allowed to change my diaper at work, but only before asking Mistress if I can do so.  Because of this, I’ll be wearing a stuffer or two with the diapers I wear to work.  This should hopefully help prevent the need to change until I can make it home.  In order to remain discreet and professional, I’ll be allowed to change my diaper without first asking at work only if I believe I am about to leak or if I am unfortunate enough to do so.  However, I will be punished once I return home.

I’m going to do my best to provide a daily update for the next seven days, or more, for all of you to follow along on my new and exciting adventure!

If there are any ideas, words of wisdom, or encouragement you have for myself or Mistress please let us know here!

Naughty Sissy Sasha

After Mistress caught Sasha trying to rub her clitty she pulled out all the stops to punish her.  For 48 hours Sasha was forced to wear three diapers, three stuffers, plastic foam diaper cover, and the bondage mitts shown below.  

To add insult to her predicament, Mistress removed her chastity cage and told her she would allow her cummies all week if she could manage to get herself off just one time in 48 hours.  

“Since you like to rub yourself so much I’ll give you all weekend to do so.  If you can’t manage, then keeping you locked for the next six months only sounds appropriate, don’t you think?”

47 hours later and Sasha hasn’t even managed to give herself a stiffy yet.  With tears running down her face Mistress walks into her room as Sasha frantically rubbed herself.

“It looks like you’ll be needing this shortly, darling.”  She says as her chastity cage is placed on her bedside table.  As Sasha glances over she weeps at the realization that her previous cage has been replaced with a newer model that’s one inch smaller.

After giving Sasha a kiss on the forehead, Mistress leans over the railing of the crib and gives her a kiss on the forehead.  “I’ll be back shortly to put it on you, baby girl.” 

Mistress grinned as she left the room.  The frustrated, desperate, and frantic jingle of her baby’s mitts echoing through the halls of her house.

Links to items worn below.

Diapered In Pink

Links to items worn below.

Entering The Sissy ABDL Scene

Here is a sneak peek at one of the new outfits I purchased of the ABDL theme. Better pictures coming soon!

Below are links to the items being worn.