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Loser PeeWee gets punished again

  • Posted on October 8, 2011 at 8:15 pm

Loser PeeWee has been panty peeking again. In addition to making him wear his loser briefs I made him say “Men’s underpants are a waste on me” over and over for fifteen minutes straight.

Afterward he was out of breath and quite repentant.

Chastity keys

  • Posted on March 28, 2011 at 1:39 pm

A submissive recently locked his cock into a chastity cage and sent me the keys to begin training with me. Here they are:

chastity-keys

I have both keys so he’s locked into the device until I send them back. When will I send them back? Oh…not for awhile!

PeeWee’s punishment list

  • Posted on March 27, 2011 at 11:12 pm

Loser PeeWee’s punishments can always be worse. To show him this we came up with ten ways his last enema punishment could have been worse. Here’s the list:

1-drink a 1/2 gallon of water before enema
2-take 3 enemas back to back
3-stand on toes while holding enema
4-keep hands on head
5-keep nose in corner
6-take the enema in the garage
7-do the enema outside
8-chain himself to the punishment pole while holding enema
9-after dumping sit down in diaper
10-kneel while holding enema

Terms of respect

  • Posted on February 16, 2011 at 2:19 am

Loser PeeWee had to come up with ten phrases of respect for me. Here’s his list:

1-Ma’am
2-Domina
3-Mistress
4-Princess
5-Queen
6-Superior
7-Sublime Mistress
8-My Boss
9-My Humiliator
10-My Dominator

Submissive Michelle

  • Posted on November 4, 2010 at 12:05 am

One of my submissives wrote me a letter that she’d like me to share with my blog readers.

“My name is Michelle. I am a 61 year old ambiguous person-whatever that means. Gender identity issues have been a part of my life since I was quite young. When I was ten or eleven years old an employee of my family caught me in the bathroom wearing one of my sister’s bathing suits. To say it was embarrassing is a total understatement.

For a good part of my life I thought and acted like the man which I definitely am. In reality though I have a very honest female side and a not quite as honest male side. Anyway that’s all for now and if you have any thoughts or questions please let Twilight know. She’s my Mistress and she takes good care of me body and soul.

Yours truly, Michelle”

Loser PeeWee needs tightey whiteys

  • Posted on October 7, 2010 at 10:30 pm

Loser PeeWee has been panty peeking again and needs to be punished. Normally he wears tightey whiteys. But I’ve decided he needs a punishment that is very humiliating. I’m having submissives send me their old tightey whiteys to send onto PeeWee.

I’ll make sure PeeWee wears every single pair I get.

New York Panty Sissy

  • Posted on July 16, 2010 at 2:32 am

I’m talking to a panty boy sissy slave right now. He has several panties with him.

Panties
purple
white
black
blue
beige
brown

Madam Cynthia gave him some of these panties which he loves to wear. Sometimes Madam Cynthia and I dominate this slave together. We have such fun with him.

Right now New York Panty Sissy is wearing the white panties and blue panties. He’s also wearing black thigh highs. He wants everyone to know that he loves panties and that he has to follow all of my direct orders.

Slave Cindy’s new shoes

  • Posted on June 16, 2010 at 12:24 am

Speaking of shoes, Slave Cindy got some new slut heels.

cindy-2

Cindy is a very happy slut now.

Loser PeeWee’s new collar

  • Posted on May 8, 2010 at 2:56 am

Loser PeeWee has been pantie peeking again. Obviously, he needed more punishment and humiliation. This new collar is his:

loser-peewee-dog-tag-3

What’s the tag say? It tells whoever sees that PeeWee is a panty peeker

loser-peewee-dog-tag-1

and that he belongs to me.

loser-peewee-dog-tag-2

Slave Cindy

  • Posted on May 4, 2010 at 6:55 pm

Slave Cindy likes to wear slut heels and panties while we talk. Today he took a picture of himself for my blog.

cindy-1

You’re a good girl Cindy.