sissy billy’s Makeup Punishment for Mistress Rosemarie

Mistress Amber never forgets:

Out of the blue she noted that I had failed to complete and actually never started a punishment that Mistress Rosemarie assigned me for embarrassing her. My original punishment was for taking the sissy way out of accepting a punishment by saying that I could never wear clothespins on my nipples for more then 1/2 hour. I accepted the fact that I had ignored this punishment and accepted the punishment from Mistress Amber that I was now required to complete it. I accepted and started my punishment.

Day One:

Mistress Rosemarie intended for me to place clothespins on my nipples for just 1/2 hour on the first day. Since I was already wearing wrist and ankle cuffs per my Standing Training rules I put the cuffs on also. I also had lots of my panties to iron. I had not had clothespins attached to my nipples for several weeks now and I forgot how much they hurt. I did complete my half hour and felt good that I had done so. My nipples were already sore, but I knew the real punishment would be Day three and four.

There was one huge mistake I made. I did not tell Mistress Rosemarie that I was completing the assignment she had given me. She was so mad that I went and hid in my room. When I finally got up the courage to go back downstairs she had calmed down, I thought. All she said was that the conditions had changed and we would be starting again tomorrow. Then she sent me to my room to think about how much trouble I was in.


Day One ( Again )

I am standing here as I was two days ago and I am sorry that I did not tell Mistress Rosemarie that I had started my punishment for her. I will leave it up to your imagination how she made sure that I was sorry and that I would never do that again. I will not soon forget. I have my wrist and ankle cuffs on and clothespins are stuck on my nipples and they really hurt. Mistress Rosemarie’s addition today was my sissy clitty-cage and it is there under my heart shorts that she made me buy on my birthday and my 4″ High Heel shoes (She keeps threatening to buy me 6″ Heels which usually shuts me right up). She liked the way I looked in heart shorts and she says the red heels match my shorts. I also had to wash all my lingerie again and iron all my panties again. I kept the clothespins on my nipples for 1/2 hour as directed and completed my Day One (Again) assignment without mishap.


Day Two

Day two started with my wrist and ankle cuffs, sissy clitty-cage under my heart shorts, 4″ high heels and the clothespins stuck on my nipples. My nipples still hurt from my Day One punishment and now I had to keep them on for an hour. She also added my lace up corset which she so loves for me to wear. She helped me lace it up tightly and now I could hardly breath, which was her intent. My Nipples hurt so much and I was crying by the time my hour was up, but Mistress Rosemarie had little compassion and simply reminded me it was my fault. She then sent me off to bed even though it was much earlier then my normal bedtime. As I trudged up the stairs pouting and whining under my breath, she reminded me that the first half was easy and the hard part was to come and that if I did not change my attitude that I would regret it. I ran the rest of the way up the stairs and quickly got into bed.


Day Three

I woke up Saturday morning and when I was told I could play golf with my friends I thought she was finally going to be easy on me. As I left she reminded me that we also had a graduation party to go to for one of her friend’s kid. I don’t really like her friends, but playing golf was a good swap. We attended the party and on the way home I started whining, but stopped when she glared at me. I though better of trying to argue and shut my mouth.

When we got home she sent me to the bedroom to dress. I really was not looking forward to this and I made another mistake by starting off with a pout on my face and looking for sympathy. Mistress Rosemarie took one look at me and simply said “Strike One”. She led me to the bathroom and I quickly put my wrist and ankle cuffs, sissy clitty-cage, added panties and a bra which I was happy was not stuffed and then Mistress Rosemarie came back into the bathroom and laced up tighter then yesterday my lace up corset and then held up her clothespins with a smile. My nipples were so sore from the first two days that they still hurt to touch. Tears came immediately to my eyes and I begged her not to make me wear them again. She smiled, said “Strike Two”. She then put them on my nipples by letting them snap on and I cried out loud each time. She started the clock and set it for two hours. I was beside myself and did not know how I could do it. An hour later I could not stand it anymore. My nipples were throbbing and tears were running down my face. I started whining that it hurt too much and that I could not stand it any more. I begged for her to forgive me and stop my punishment. She really got mad then and shouted “Strike three”. She was really mad and now I was afraid and did not even feel my nipples.

Mistress Rosemarie then said she had an idea how to take my mind of my nipples. I actually had not even thought about them for the five minutes she yelled at me. She grabbed my hand and told me a good walk would take my mind off the nipples as she dragged me down the stairs from the bedroom. I was terrified that she was taking me outside for a walk and cried and begged for forgiveness. Thank goodness she did not mean to take me outside. She dragged me downstairs to the basement and started the treadmill. For the next hour I had to walk on the treadmill. It was so difficult in high heels that I almost forgot about the pain in my nipples. Finally after two hours my punishment for today was done. I was allowed to sit in the chair finally and Mistress Rosemarie left me to myself as I cried. After a short while she returned and told me that my punishment would be twice as hard the next day.


Day Four

As soon as we got up in the Morning, I was told of my added punishment for my insolence and whining. I would walk for the entire two hours, but would have an option of writing a punishment sentence ( “sissy billy is very sorry that she did not do as Mistress Rosemarie told her to do. She will listen to all the Mistresses from now on and perform their punishments immediately without whining” ) when I got tired of walking and that as I was writing the sentence I would either have a bar of wet-ted Pink Camay Soap or my penis gag stuffed in my mouth. It was my option. So that she could keep track I was to put an S or P next to the sentence so she would know which option I chose. Since I was to wear a diaper and rubber diaper cover it was appropriate that she made sure that I did have an accident and wet my diaper. I was not to go to the bathroom for two hours before we began and that I would drink 64 oz’s of Gatorade before we started. She already had out the balloons for my big bra. I now had all morning and afternoon to think about it before we started.

I was not allowed to do anything but sit at the dining room table for the entire afternoon. I worried all afternoon until I was to start my final punishment at night. I was dressed in everything as noted above and then led to the basement to start.

I was tired from worrying before I started. Mistress Rosemarie started the treadmill and then put the pins on my nipples. By now my nipples were so sore that they immediately started to throb and burn. I started to walk and the pain in my nipples seem to double with each step as the balloons bounced in my big bra constantly moving the pins attached to my nipples. After about fifteen minutes I could not take the bouncing bra and pinching pins and I asked to rest and write a punishment sentence. I wrote three sentences with the Pink Camay Soap stuffed in my mouth and then gagged as the soap dripped down my throat. I almost threw up. I took the soap out an asked to walk again.

This time I had to play a game on the Treadmill. I was to make believe I had to take the bus to work. I started out on the treadmill slowly and it was easy to keep up even though my feet were already hurting. Then after 5 minutes I was late for the bus and had to walk faster for three minutes. Then the bus was coming and I had to move the speed up another notch to reach the bus stop on time. I could hardly keep up. I had never thought about running in high heels and had to take little steps with the high heels. I was getting really tired and then I had to cross the street and I had to make the treadmill faster. Finally I could stop and I could rest, but would have to write another punishment sentence. I stuffed the penis gag in my mouth. This went on for the whole two hours and because the Pink Camay and penis gag were so bad, I tried to walk as much as I could.

It was a blur of walking and soap and gag, but I had to complete this last day or risk starting all over again. When the two hours where up I fell into the chair with exhaustion and cried and told myself I never wanted to do that again.






Day Five

I slept like a baby through the night. I was so glad to go back to work, but the pain of the punishment is still there. My nipples hurt everytime I move and my shirt rubs over my nipples. My legs are so sore they are throbbing. I imagine it will be a few days before the pain goes away, but this punishment will stick in my mind for a long time.


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I am sorry too as I tried to push Mistress into showing Herself by my namecalling and defiance to the stated punishment. Every Woman that I meet I wonder,, “Is it Her?”
In a way I get the answer is “YES” as All Women are my Superiors.
Thank You Mademoiselle and good night.

That sounds awful. Mistress Katzenburg told me that I am to wear clothes pins anytime I am mailing her or reading posts. Which is hard because they hurt after a while but I can’t stop reading because the posts are so interesting. but I know now how bad those pins can hurt now.

I find that clothespin i wear can be a pain, however i am hppy if i have no choice of the wearing and hope to have some supervision .

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