Sissies Must Be Trained To Stay Limp

This evening Mistress allowed me the pleasure of riding my dildo with one condition. As soon as I get an erection I must immediately stop and be put back in chastity until she permits me to give it another try.

It goes without saying I am forbidden from touching my pathetic little clitty while doing so. She says this method will continue until I am able to dribble my sissy cream from pussy stimulation only like a properly trained sissy.

Below is a 10 second clip of my first attempt. Anyone want to make a guess at how long I lasted? Additional videos will be uploaded soon!




Advertisements

Introducing Miss Pansy Bouffant!

Miss Pansy Bouffant is a sissy dress with a petticoat far larger than the brain of the sissy wearing it.

The sissy was forced into her D cup breasts that were attached with medical grade adhesive to ensure the sissy is unable to remove them during her daily tasks.

Her heels jingle with each step so mistress doesn’t need to keep an eye on sissy to verify she is dutifully working through her long and arduous tasks around the house. The locking ankle restraints ensure small mincing steps to further exaggerated her ditsy walk.

The tag on her locking posture collar adorned with more bells reads “Pathetic Pansy”, announcing to everyone she may come into contact with her true self worth.

In the video below, sissy maid Sasha is practicing her curtsy for Mistress’ return from her weekend long trip later this evening.

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.

Punishments

  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!

The Sissy Housewife – Part 3

“Do a twirl for me.” Brad commanded as he sat in the corner of the bedroom. “Give me a tease of those frilly panties you’re wearing, sissy!” As Sasha spun in her high heels, her petticoat lifted itself off her body and provided Master the quick glimpse beneath her petticoat he requested.
“Mmmmm… that’s very nice, Sasha. I can tell you’ve been doing your daily posterior workouts. That ass is looking better every day! The Brazilian butt lift was an excellent choice too, don’t you think?” As he finished speaking Brad rose from his seat and began walking towards his prized possession. Sasha instinctively cast her gaze downward as she pulled her dress and petticoat out to each side, crossed her feet, and bent her knees to perform the picture perfect curtsy for her Master.


“Yes, Sir.” Sasha responded with her gaze fixated towards the ground before returning to her original position. “Don’t you think your sissy Sasha needs additional body enhancements?” She was required to always ask for more of whatever she was being complimented about. Not doing so would ensure a harsh punishment from both Master and Mistress.


Brad stood inches away from Sasha now, her fluffy petticoat compressed against her by his imposing figure. With a smirk on his face, Brad reached around and underneath the bouffant petticoat and grabbed a handful of her sculpted ass before giving it a firm squeeze. His other hand rested itself on her waist with a possessive grip. “Hmmm. Maybe that’s not such a bad idea… cunt.” Sasha took his insult just like she did everything else from him, with a smile on her feminized, cum soaked face and a “Thank you, Sir!”


“You’re very welcome, sissy. A good girl like you deserves to be spoiled every once in awhile.”


“Yes, Sir! Thank you, Sir!” Was the only response the slave could give in return.


“You are just so adorable, Sasha!” Grace once again joined the conversation after her quick shower. “Brad, those panties I purchased for our dear Sasha have a delightful surprise for you in the rear.”


“The rear?!” Sasha thought to herself. “What is she talking about???”


“Oh?” Brad said aloud as he quickly grabbed Sasha’s wrist and forcefully spun her around. As she twirled, Sasha lost her balance and landed bent over on the bed, her face lying in the sticky puddle of sex leftover from her owners love making just 30 minutes earlier.


With her in such a compromising position, Brad easily lifted the petticoat out of the way to get a good look at Grace’s gift. “Oh my, sissy! Grace really did get you some naughty panties!” He then ran his fingers along each thigh before tracing the outline of her panties. With a quick snap of her garter belt, Sasha let out a yelp as his other hand groped her clitty locked between her legs.


“Still wet as ever I see.”


It was at this time she also heard the unmistakable sound of a zipper and the cool breeze tickle her fanny. Sir eagerly ran his hand inside her panties and teased her pussy with his fingers. Her clitty instinctively clenched itself as the foreign object teased its walls.


“Sasha, my dear sissy” zzziiiiiiiiiip “I hope you’ve been doing your daily stretching exercises as well… If you haven’t, then consider this part of your punishment…”


To be continued.

The Sissy Housewife – Part 2

Sasha wasn’t given the opportunity to speak as her Mistress lowered her engorged cunt into position onto her face. The putrid smell of her owners sex coated Graces mound in a viscus mixture destined for her sissies consumption.


“Come on now, Sasha. Do just as we’ve practiced all those previous times. Don’t force Brad to get out the Hypno Cloud for poor performance. I know you still remember the last time you were forced to wear it.” Sasha did remember her week with the Hypno Cloud, it was seven day’s she would never forget or want to experience again, and all three of them knew that.
Before she could dwell on it though, her mind kicked into gear as Grace’s mound seated itself on her face. Sasha stuck out her tongue as a drop of cum oozed from her vagina. As she sucked down her first taste of Brad, Grace grasped a fistful of her hair in each hand and pulled her in closer, cutting her breathing short as her nose was pushed firmly into Graces groin. Sasha explored the recesses of her ex-lovers warm pussy in the only way she was now permitted. Grace’s once sweet taste of yesteryear was defiled and corrupted by another man’s cum she was now forced to consume as her reward for their love.


Grace bucked her hips up and down her sissies face as Sasha’s tongue eagerly scooped out the seed implanted within Mistress. Her head raced and breath grew short as Sasha pressed all the right buttons for Mistress’ pleasure alone. Months of punishments and practice have turned her into a masterful cunnilingus sex machine. Sasha had no problems bringing Grace to multiple orgasms with her expertly trained tongue, each one supplying yet another mouthful to swallow.


“Live vicariously through me.” Grace’s words from training reverberated inside her head. “Accept my orgasm as your own.” As Grace came again, their mixture of fluids were deposited into Sasha’s eagerly waiting mouth for immediate consumption. The lewd sucking and slurping sounds that filled the voids between Grace’s moans were suddenly interrupted when Brad tapped the cage adorning her button of a clitty.


“That’s enough for now you two.” He interjected before continuing to speak again. “Sasha is creating quite the mess between her legs, Grace. We wouldn’t want our little girl to have an accident, would we Sasha?” His imposing figure towered over her petite and weak body as she laid underneath Grace on the bed. Growing impatient for her response, he raised his brows and stared deep into her eyes for an answer.


“But Sir…” she gazed back at him with her best puppy dog eyes. “…you said I had been a good girl for the past year and would be allowed cummies. I…” Sasha stopped herself from continuing as the realization of what had just transpired occurred to her small mind. She had been allowed the cummies she was promised, they just weren’t hers. It was at this point she understood the true meaning of Grace’s words.


“Live vicariously through me. Accept my orgasm as your own.”


To be continued…

The Sissy Housewife – Part 1

*jingle jingle jingle*

Sasha minced her way across the house to the sound of her calling bell originating from her bedroom.  By the time she made it in her 6” heels she was greeted to an empty room with a piece of lingerie and note waiting for her.  Her pathetic clitty strained in its cage as a drop of precum leaked from the tip and stained the petticoat currently tied around her waist.  It has been so long since she was allowed cummies, and her tiny clitty was desperate to spurt its minuscule load; the outfit on her bed left no doubt that her hard work around the house was about to be rewarded.

“Put on your gift and wait outside our bedroom door.  We’ll let you know when to enter.”  — Brad

She eagerly stripped out of her maids outfit and slipped into the pink teddy.  The thin satin fabric sent her into sissy heaven as it slid across her body.  Its feminine lace tickled her thighs while her permanently erect nipples strained against the fabric, one of the many body enhancements ‘given’ to her by Master.

As she kneeled in front of the bedroom door she could hear the muffled sounds of rough passionate sex occurring just beyond her reach.  Sasha took this time to reminisce about his previous life with his wife.  The euphoric and beastly feeling of filling his wife with sperm was nothing more than a dream for her now.  She had left him for a real man years ago, the same man currently filling her pussy on the other side of the door.

“Come in Sasha!” Brad’s voice finally rang out.  She must have waited on her knees over an hour as she eagerly opened the door and curtseyed before crawling to the edge of her Master’s bed.

“Don’t be shy, come on up here with us!”  His ex-wife commanded.  Sasha looked at both of them with a puzzled and nervous look on her face.  She had never been allowed onto their bed before. Doing so would have been met with extreme punishment, something she had no interest in after years of strict training. 

“Aww… don’t be shy, baby girl!  I promise it’s okay just this once!”  Grace continued as she patted the bed with her hand. 

Sasha nervously made her way onto the bed.  As she did, Brad’s hands groped her large tits and ass, both gifts ‘given’ to her by him just six months earlier.  “I think it’s about time for your second round of upgrades!” Brad chuckled as his hand slapped her jiggling derriere.

“Lay down, Sasha.  We have a surprise for you tonight!  The next few hours are going to be all about you!” Grace giggled as Sasha laid her back on their bed.  As she finished getting into position, Grace repositioned herself so that her pussy, filled to the brim with Master’s seed, was resting just above her face. 

“One year ago you were told we would give you cummies if you perform your duties without complaint.  I’m so happy to inform you that Brad has agreed the time for you has finally come!  Now drink up and clean Brad’s cummies out very thoroughly, sweetheart. If you don’t, there’s a good chance we’ll have a baby for you to care for in nine months! Haha!”

To be continued…

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.

https://thesissystore.com/adult-baby/sissy-baby-bunting

https://thesissystore.com/adult-baby/satin-abdl-luxury-bondage-mitts

https://thesissystore.com/shoes-and-boots/trainer-t-bar-mary-jane-shoes

https://thesissystore.com/stockings/sissy-long-socks

https://thesissystore.com/panties/plastic-kiss-sissy-foam-panties

Diapered In Pink

Links to items worn below.

https://thesissystore.com/adult-baby/sissy-baby-bunting

https://thesissystore.com/adult-baby/satin-abdl-luxury-bondage-mitts

https://thesissystore.com/shoes-and-boots/trainer-t-bar-mary-jane-shoes

https://thesissystore.com/stockings/sissy-long-socks

https://thesissystore.com/panties/plastic-kiss-sissy-foam-panties

Humiliating The Sissy

A short caption of a scenario I can only dream about. 

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.

https://thesissystore.com/panties/plastic-kiss-sissy-foam-panties

https://thesissystore.com/adult-baby/satin-baby-sleepysuit

https://thesissystore.com/adult-baby/sissy-baby-playsuit

The Jewel of Epicene

After just one month at the FEM Academy, Alex, now Sasha, is ready to return home to his wife.  Little does he know, his journey into feminine submission has only just begun.

This is the beginning of a story I’m starting to write.  I’ll continue to post updates here and at CleverSissy.tumblr.com as I progress.

The Miss Prisella Sissy Dress

The Miss Prisella Sissy Dress is the one that jump started my Tumblr blog and started to draw the most attention.  It’s made of primarily pretty pink satin and complimented with blue bows throughout.  I ordered this dress with a matching panties, garter belt, stockings, and blue petticoat.  

Below are all the photos from my Tumblr blog in higher quality.  Please stay tuned as I’ll be posting new dresses in some very compromising positions the very near future!

If you have any requests on what I should do in my pictures, gifs, or videos please leave a comment below!

You can view and purchase this dress at the link below.

https://thesissystore.com/sissy-dresses/miss-prisella-satin-sissy-dress