My Experience with Princess Shimmy’s Chastity Hell Week

Sunday, July 6th, 2014

Below is a journal of the experience that I had with the beautiful and powerful Princess Shimmy while completing several of her Niteflirt PTV assignments, including Chastity Exposure, Chastity Hell Week Part 1, Chastity Hell Week Part 2, and Chastity Hell Week Part 3.

It all started on a Tuesday in late October when I completed Princess Shimmy’s Chastity Exposure assignment.  I’m not exaggerating when I say that Princess Shimmy has an amazing imagination and creates the very best assignments you will ever find.  This particular task was to expose myself as a submissive, a pervert, and a boy in need of chastity to a close female friend.  After several drinks and a lot of fear, I chose my oldest friend Amanda to expose myself to.

I was thankful for the chance to expose myself.  I deserved to be outed as a pervert and a freak.  I had the words bouncing around my head, “you are a loser and you need to let your inner loser out so nobody can ever be fooled again.”  So Princess Shimmy’s assignment was perfect for me.

In my confession letter to Amanda, I confessed how I had once stolen her pretty socks that had little roses embroidered on them and had used them to repeatedly masturbate while thinking of her.  I promised her that because I was a pervert and had stolen her socks, used them so abhorrently, and lied to her about it – and because I had done many other perverted things since then, that I would be in permanent chastity, and I sent her a picture as proof.

Thankfully, Princess Shimmy had come to the rescue again with an assignment called “Chastity Hell Week” that I could use to be punished, further publicly exposed as a pervert, and put into the permanent chastity that I felt was so rightly deserved.  Thank You, Princess Shimmy.

DAY 1: MAID MONDAY

Princess Shimmy’s Chastity Hell Week and Maid Monday began early on a November morning.  When I woke up that morning, first thing, I stood in my worship/shame corner and I put on my chastity device for Princess Shimmy, knowing that I would never come again.  It was exciting because I knew this is what I needed and deserved.  It was so exciting that it was difficult to put my device on because I started to get hard.  It’s just further proof of what a pervert I am.

I wore my chastity device all day and I didn’t touch it, but I was excited to come home from work to do my cleaning.  I took some pictures of myself in the bathroom mirror as I prepared.

I made a little video of me getting dressed and putting on my make-up.

Then I made a video of me doing all my chores, dutifully licking and cleaning and scrubbing my bathroom, washing windows in view of the neighbors, vacuuming and folding my laundry.  Maid Monday was fun.  I felt so good in my little bikini bottoms and sissy t-shirt.  Thank You, Princess Shimmy, for turning me into a good little maid and housekeeper.

 

DAY 2: TOUCHY TUESDAY

The next day was called Touchy Tuesday and my instructions were to touch myself everywhere head to toe whenever I had a moment alone.  I took full advantage of it.  I had lots of time at work that day to put my hands under my shirt and rub my bitch tits and twist my nipples and rub my thighs.  Then when I got home, I sat in a chair for an hour and touched myself, put clothes pins on my nipples, practiced for the future Fellatio Friday by sucking and licking a black dildo and then sticking it up my ass and touching myself some more.  I made a video of that too.

I also took some pictures, because several times I had touched my chastity cage through my jeans while at work, not trying to cum, but out of the habit of feeling so aroused.  Princess Shimmy’s punishment for this was that I had to sleep on the floor that night with my black dildo in my ass.  Thank You for my punishment, Princess Shimmy.

 

DAY 3: WAXING WEDNESDAY

Wednesday was a more challenging day due to my chastity.  It had been 3 days now being locked up, and after Touchy Tuesday, I was feeling very horny.  After work, I went to my usual Wednesday evening inter-mural volleyball league, and we played a game against a team with two beautiful and athletic young ladies in their early 20’s or so.  I just wanted to drop to my knees on the court and touch myself for them, to show them how beautiful I thought they were.  That fantasy was so distracting, it was so hard to concentrate on the game.  And when I got home, I desperately wanted to touch myself.

I had also been thinking of Princess Shimmy and the fact that She had so easily talked me into exposing myself as a pervert to my best friend.  I was thinking of Princess Shimmy’s beautiful Goddess curves, and thinking of how that beauty and Her strength and power were going to ruin me, and how I need to be punished and humiliated by Her.  It had me feeling so randy.  But thankfully Princess Shimmy had a task for me to focus my energies on.

This day was Waxing Wednesday and when I got home, I went right up to my bathroom to begin my task.  It took nearly two hours, and I’m not even a hairy boy.  I started with my chest, which wasn’t too painful, but my chest broke out in a rash during the process.  My underarms hurt a lot.  The area around my chastity device turned bright red and was the most painful.  My legs weren’t so bad, but they got black and blue spots from the waxing.

Now I had a better understanding why women should only be with real men and not loser perverts like me.  Because it takes so much work and effort for a woman to make herself perfect.  I felt shame for all the times I though of a pretty girl and beat off, because she deserves better for her efforts that to have a pervert like me soiling her beauty with my sick and disgusting habits.  I should have apologize to those two women that I had nasty thoughts about during volleyball.

Thank You, Princess Shimmy, for teaching me a very important lesson that day, and thank You for my punishment.

DAY 4: TORTURE THURSDAY

The next day was Torture Thursday.  After dinner that night, I went upstairs to my bathroom and I stood in the shower so I wouldn’t make a mess, and I obeyed my instructions for the day.  I brought a fresh bottle of Tabasco sauce and a hair brush into the shower with me.  I spread the Tabasco sauce on my balls, and then I hit myself with the hair brush as many times as I could stand.  I’ve posted the video below.

I guess from the video it doesn’t look that I am hitting them that hard, but I can say that it hurt a lot and I hit them as hard as I could get myself too.  At first, I feared the Tabasco sauce, but it didn’t hurt like I thought it would.  But a few minutes in, the sting grew and grew and became nearly unbearable.  The worse part was that I wore the smallest ring on my chastity device so that it wouldn’t slip off while I am playing sports or running, and so some of the sauce got underneath the ring and pressed into my balls, and it was nearly unbearable.  Even in the shower after, it wouldn’t wash off, so I just had to suffer with it.  The shower didn’t really help that much.  You can hear me moaning even while in the shower.  It felt good while the cold water was on, but as soon as I shut it off, the burning started again.  It took all of a 90 minutes to recover.  It still hours later and for a while I couldn’t sit and had to just stand up.  This experience had me so fearful for Sadist Saturday, but I promised myself that I would do the best I possibly can, because I know that I deserve this harsh treatment.  I deserve to be punished and punished brutally, and I was very thankful to Princess Shimmy for giving me what I deserve.  Thank You, Princess Shimmy.

At least the next day Fellatio Friday would be a little break.  I love to suck cock, and I was excited to learn to deep throat.

DAY 5: FELLATIO FRIDAY

Fellatio Friday was an exciting day because I got to practice my cocking sucking skills for Princess Shimmy.  I printed out a picture of a hung stud with a juicy, meaty cock for inspiration, and I mounted my dildo to the wall in my shame corner and got down on my knees and tried to be the best little cock sucker I could possibly be.  I was proud of being able to take the cock so deep into my throat.  If ever my perversions get me into serious trouble, at least I know my mouth will be useful in prison.  In the video, you will see that I wiped my finger across my lips and licked them, because I was imagining the huge load of warm cum that could be spilling from my mouth.

While Fellatio Friday was a pleasure, I was still fearful of what was next.  Sadist Saturday was truly frightening.

DAY 6: SADIST SATURDAY

When i got home from work the next day, Sadist Saturday began.  I was fearful and hesitant to begin, but I decided to put my fear aside, because I had made a commitment to Princess Shimmy to finish the task She had given to me, and I knew I was so deserving of punishment and humiliation.  So deserving was I that I was honestly thankful to Her for it.

I tied my balls as instructed, rubbed icy hot all over them and the shaft and head of my little penis, and then slapped my balls with a wooden spoon 20 times each as She had directed me.  The burning all over was painful and intense, but this was still the easy part.  Next was the scary part.  I was afraid that having icy hot inside my body wasn’t safe, but I took a deep breath, filled a syringe, and pumped 1 ml of icy hot inside my urethra.  Then I took the q-tip, put icy hot on the end, and then inserted it to push the icy hot deep inside my penis.  My balls and my cock were painfully burning, but I was surprised that inside my urethra, it didn’t hurt.  I was easily able to push the q-tip inside.  I completed this 4 more times for a total of 5ml.  Most of the icy hot went inside, but a little came out with the q-tip.  Then with my assignment completed, I locked myself back up.

When I first peed, I was scared because I was afraid the q-tip might have done damage.  But I was able to pee, and when I did, a long white stream of icy hot came out with the pee.  It didn’t hurt at first, but then every time I peed after that, I had the most painful burning sensation.  It would make it hard to start peeing, because of fear of the pain, and I wanted to scream every time.  This lasted 2 full days.  Then the 3rd day it started to subside, and now it is all gone and everything is back to normal again.  I almost wish it still hurt.  I miss the pain that Princess Shimmy gave me.  Thank You for hurting me, Princess Shimmy.

I went to sleep that night all ready for Sacrifice Sunday, the final day that I might last the rest of my life.

DAY 7: SACRIFICE SUNDAY

Sunday was the final day of my chastity assignment, the day when I would permanently enter chastity to pay for my sins.  I was instructed to rub myself slowly for 4.5 hours, and then for the final 30 minutes, I was allowed to edge 15 times but not cum.  I did this like a good boy.  I used pictures of Princess Shimmy from Her “Dirty Sneakers & Foot Worship” Photoset for motivation.  She looks so hot in Her jogging outfit.  It reminds me of all the times I’ve gone to the local park, North Ponds Park, and sat in my car and rubbed myself while the sexy female joggers go by.  It’s another good reason I should be in permanent chastity.  There are so many reasons.

I stood for a couple hours rubbing myself.  I began to have crazy fantasies.  I imagined being at the park watching the sexy female joggers going by, rubbing myself, and then I imagined Princess Shimmy running by and catching me.  I imagined Her making me strip, tying me to a tree by collar and chain at the edge of the trail, and making me kneel there in sight of everyone going by.  I imagined all the pretty lady joggers going by, stopping and making me lick their sneakers clean if they had stepped in dog poop.  I even imagined the male joggers who needed a bathroom break, stopping at the “pervert of North Ponds Park” to unzip their pants, stick their dicks in my mouth, and piss down my throat… and Princess Shimmy just stood a safe distance away and smiled and laughed.  As the time went on, my fantasies became more and more depraved.  It was so hard not to cum.

After a while on my feet, I got on my bed and humped my pillow while still adoring Her picture.  I almost came then.  I felt it start and so I stopped rubbing up against my pillow for a moment.  A lot of fluid came out all at once, but no orgasm.  I often dream of licking up my cum while I touch myself, but once I cum, I no longer want too.  I knew it was just pre-cum this time, because the desire never left me, so I licked up my mess off my pillow before I continued again for the rest of the 5 hours.

I hit my balls with my fist five times when I was done, and then I assembled my chastity device again just like I was instructed, gluing all the pieces together with superglue, and then filling the keyhole in the lock with superglue.  The superglue almost immediately became hard as cement.

I was thankfully to be locked this way without a key  I knew I would still be a pervert, but at least I thought I could no longer steal my friends socks just to abuse them, and I could no longer touch myself while leering at the joggers going by at the park.  But the chastity ended up lasting only one month before I ended up cutting the peg on the device.  I can’t even remember why I did that now.  My friend ended up forgiving me, and asking me to take it off, so that was probably part of it.  But I know permanent chastity is still what I deserve, and so that is one of the many reasons for this blog, to try and try again until I get it right.

Perhaps if I had begged Princess Shimmy to make me her chastity slave and received her follow-up and instructions, I would have had better success, instead of just buying a one time assignment.  It was a great assignment though.  I highly recommend Princess Shimmy as a Key Holder and strict and beautiful Goddess worthy of obedience and devotion.  You should call Her today and visit her PTV store.

Mommy’s Wimpy Boy