Well, it was inevitable, after failing to hold my sissy orgasm last week when Mistress Amanda worked me over per Mistress Christines instructions, punishment was inevitable. First Mistress Christine informed me that I had failed and disappointed her and that punishment was mandatory. Three things had to be done before my next phone call to her on Saturday.
1. Paint my toenails a very pretty pink and keep them painted until Saturdays session.
2. Edge three times in one evening, of course the minimum dress code was not sufficient and a full outfit and heels should be worn while edging.
3. Dress completely as a female would to go out and then stand in the corner in a pair of 5 inch heels and contemplate how I had failed.
Mistress Christine checked on my progress through the week ensuring I didn't slack off the punishment assignments.
4. Saturday's session would be a punishment session and she was really going to put me through the ringer.

Saturday I messaged Mistress Christine and she then instructed me to get dressed, bring all the toys I had to my play area, hand cuffs, leather cuffs, locks, etc. My buttplug was to be inserted, and most certainly bring the nipple clamps. Oh and some toothpaste, and a ruler.

Getting dressed in my white underbust corset, tightening the laces by hooking them over the door knob of an open door and leaning forward and exhaling, I managed to finally cinch myself up tight. Then the stockings, it is difficult to bend over and gently pull up the stockings with a corset that tight but I managed it. Next came the task of hooking the eight garters, the back garters being especially difficult but finally they ere hooked. A very pretty pink with lace trim babydoll nightie was added. I just wanted to rub my hands all over my body. Then the lovely and sexy pink with black trim open toe 5 inch heels and of course the pink lacy panties over the garters so Mistress would have the best access to my sissy parts.

Mistress first informed me of my misdeeds and made me repeat my understanding of them and ask her for punishment.This was definitely humbling and embarrassing as well. But it got a lot worse when Mistress made me dance for her like a stripper, dipping, and grinding, and swaying my ass like a slut in heat, giggling at me as well. I was as red as cocksucker red lipstick all over from embarrassment. Not being contend with this I was required to remove my buttplug and cover it liberally with toothpaste. Forced to turn around with my sissy ass to the webcam I had to reinsert the coated plug. Then it began the burning and stinging sensation, there was nothing I could do to stop it, even removing the plug would not help, and that was forbidden. Then the uncontrollable urge to wiggle and squirm from the pain started, I just couldn't hold still, I surely looked like a sissy slut wiggling my ass as if to invite someone to penetrate it. I was instructed to rock back and forth kneeling with my ass to the camera, against my heel forcing the plug in deeper and causing me to moan like a slut. Again Mistress Christine chastised me and asked me if I deserved my punishment, forcing me to admit I needed it and how much I really liked. I would have said anything to please her, but it really was true, I wanted her to punish me severely.

Wiggling and not being able to touch my sissy clitty, I was instructed to handcuff myself with my hands behind my back. Now I really couldn't do anything to protect myself or even try to remove the plug and stop the stinging. The dancing sissy slut was required to dance again for several minutes. The aroused sissy clitty was then to be humped against the arm rest of the couch until Mistress said stop. Humping with knees bent to get down to the level of the armrest was almost torture, very tiring especially with the 5 inch heels making me bend at the knee greatly, straining my calves and thighs. But the sensation and urge to orgasm was excruciating as well. Of course all this was going on with a very tight set of nipple clamps attached and the beads hanging from them swaying and pulling at my by now very tender nipples. Mistress Christine requiring me to tell how I was feeling all the while and if I deserved my punishment, requiring me to say how much I deserved it. Next I was allowed to kneel and rest my legs, but things were not exactly comfortable, being required to kneel on a ruler until told to get up. Then back to dancing and sitting on the armrest and bouncing on it driving the plug deeper and making me squirm more from the toothpaste burning sensation.

After all this I was finally allowed to uncuff myself and sit on the couch. Mistress asked if I wanted to stroke for her at which I eagerly said yes. But lacy was not allowed to cum, Mistress gave lacy a number of strokes and required her to count them, first 20 without cumming. Since lacy did a good job 30 was in order, stroking and counting and begging for release. "Lacy I said not to cum, don't disappoint me you are doing so well" was Mistress Christines encouragement to lacy. Next it was 60, counting, stroking, and being teased was almost painful. But lacy made it through it with out cumming. The big test was next, Mistress said "lacy I want you to stroke 100 times for me without cumming, if you do you will be punished again this week." I began the stroking and counting, then Mistress upped the tease factor telling me how much of a slut I was acting like and how much she loved punishing me, teasing more and more, then it happened. I came violently at sixty strokes. Mistress Christine was displeased and made me eat my own cum and teased me even more. I was made to admit my sissy short cumming and was made to repeat my new punishment assignment to be completed this week. I slowly repeated several times to ensure Mistress I understood "I will go to an adult novelty store and select a 7 inch long lifelike like dildo. If a female clerk asks me if I need help I will tell her that my Mistress is requiring me to purchase a dildo for me to practice on." If not approached while choosing, I am to tell the female clerk at check out that Mistress wants me to buy it to practice on." I will also be required to wear panties, bra, hosiery, etc. under my (uggh) male clothes. I will surely be humiliated by the female clerk for buying a dildo to practice on. But Mistress Christine is in control of me and I must obey her by doing this.

lacy's trial by Mistress

As instructed by Mistress Christine I instant messaged and emailed Mistress Amanda for a session on saturday morning. Mistress Amanda asked me what toys I had and then proceeded to ask me several questions. I was very nervous as the web cam came up and started transmitting the picture of me dressed in a corset, bra, panties, micro fishnet stockings and a slip with my 5 inch d'orsay heels. I had to twirl around and show my panties, and corset by pulling up my slip. Then Mistress Amanda commanded me to dance like a stripper. I had to bump and grind and like a slut. Then she commanded me to get some toothpaste remove my butt plug and coat it with toothpaste, reinsert it and pump myself with it. The burning started quickly and made me squirm uncontrollably, there was no escaping it. I had to rock back on my heels which caused the heel of my shoe to push the plug further in. I tried to rub my aching sissy clitty but she made me remove my hand each time.
The next effort was to hump the arm rest on the couch. This caused my legs to feel like jelly. Then she asked if I had any hand cuffs and I had to retrieve them. Locking them on my wrists behind my back she again made me hump the couch. This really wore out my legs and was tiring quickly, especially with my state or arousal. Allowing me to remove the cuffs she again made me pump myself with the buttplug and then spank myself with my hand 30 times. Then she allowed me to sit on the couch and rub my sissy clitty, making me stop occasionally and teasing me about how I wasn't supposed to cum per Mistress Christine's instructions. I was begging for release but also begging not to disobey Mistress Christine for fear of punishment. Mistress Amanda made start stroking again, telling her how many strokes it might take me to cum and then adding to the required number of strokes for me to complete. Finally telling me to stroke it 100 times without cumming. Agonizing the whole time I began to stroke, it was torture, then it happened, at around 80 I came, there was no way to stop it. I had failed. Mistress Amanda laughed at my sissy clitty and my cum on my hand making me lick it and the towel the rest of my cum landed on. I was so humiliated and so disappointed in myself for letting Mistress Christine down.
My last assignment from Mistress Amanda was to take a cold shower, redress and clean the house dressed up, write emails to Mistress Christine and copy Mistress Amanda about my session and then another email about my experience cleaning the house dressed for the rest of the day. The humiliation was compounded by the fact that she had recorded the web cam video session on her computer and will be sending it to you for review. Mistress Amanda told me I would have to ask permission from you to view the video.
Sincerely,
lacy

Assignment List

Mistress has required me to maintain an assignment list that she may add to or modify at her whim.

1. Purchase a dildo according to Mistress specifications
2. Purchase larger butt plug
3. Purchase a fleshlight masturbation toy
4. Shopping for stay up thigh high stockings
5. Shopping for matching bra and panty sets
6. Shop for and try on a matching skirt and jacket suit
7. Shop for and try on women’s slacks
8. Buy a new pair of flats
9. Buy a new pair of knee high, highheel boots
10. Purchase pads with wings
11. Purchase nail polish, Mistress choice of color
12. Purchase mascara
13. Paint toe nails, Mistress choice of color
14. Wear panties, pantyhose and bra to work
15. Wear panties, thigh highs and bra to work
16. Wear panties, girdle and stockings to work
17. Wear womens socks all day
18. Wear women’s blouse when shopping for fem items
19. Wear women’s slacks when shopping for fem items
20. Wear women’s slacks and blouse when shopping for fem items
21. Wear women’s slacks, blouse and flats when shopping for fem items
22. Suck off a dildo for 10 minutes while edging
23. Suck off a dildo for 20 minutes while edging
24. Suck off a dildo for 40 minutes while edging
25. Suck off a dildo for 60 minutes while edging
26. Wear lipstick and suck off a dildo for 10 minutes, reapply lipstick after 10 minutes
27. Wear lipstick and suck off a dildo for 20 minutes, reapply lipstick each 10 minutes
28. Wear lipstick and suck off a dildo for 40 minutes, reapply lipstick each 10 minutes
29. Wear lipstick and suck off a dildo for 60 minutes, reapply lipstick each 10 minutes
30. Purchase a CB2000, CB3000, or CB6000 chastity device
31. Purchase the points of intrigue for the CB device
32. Wear a maids uniform and sweep the house wearing 4” or higher heels
33. Write a fantasy and publish on blog
34. Purchase something for Mistress
35. Buy a wig
36. When sleeping alone wear a nightie or negligee to bed
37. When sleeping alone wear a nightie or negligee to bed with ankle strap heels
38. Masturbate using only thumb and fore finger, pinching and rolling skin between them
39. Dress up in corset, bra, panties, stockings and 5 inch heels, secure a vibrator at a height that requires standing up, hands cuffed behind back, ankles cuffed and edge for 30 minutes

Punishment list

Below is a beginning of my list of punishments that Mistress is requiring me to maintain per Mistress instuctions. Mistress Christine's comments and changes are in red. She may add and modify at her whim.


1. Stand in the corner dressed and wearing 4 inch highheels for 15, 30, 45, or 60 minutes - All of these are good
2. Stand in the corner dressed and wearing 5 inch highheels for 15, 30, 45, or 60 minutes
3. Stand in the corner dressed and wearing 6 inch highheels for 15, 30, 45, or 60 minutes
4. Paint toenails pink and keep painted for 3 days - I think you would like this, but I know it will be dangerous for you...so it could be fun for me
5. Paint toenails pink and keep painted for 7 days
6. Paint toenails red and keep painted for 3 days
7. Paint toenails red and keep painted for 7 days
8. Edge for 15 minutes - Can you actually edge for that long? We might have to revise these to a number of times in one day to edge
9. Edge for 30 minutes
10. Edge for 45 minutes
11. Edge for 60 minutes
12. Kneel while dressed on rice for 15, 30, 45, or 60 minutes These are good
13. Kneel on a ruler while dressed for 15, 30, 45, or 60 minutes
14. Wear nipple clamps for 30 minutes, remove and reattach for another 30 Nipple clamps...mmmmm, I like
15. Wear nipple clamps for 60 minutes, remove and reattach for another 30
16. Wear nipple clamps for 90 minutes, remove and reattach for another 30
17. Wear buttplug to bed all night Can you get away with this?
18. Wear nipple clamps and tie them to the clothes rod in the closet blind folded and hands cuffed behind back while dressed and wearing heels. How will this work out? Will you need help?
19. Lacy cannot wear highheels for one week and must wear only flats when dressed This is awesome...but the dresscode may conflict....you might have to use a special way to present yourself to me, like...."My beautiful, awesome Mistress Christine shouldn't have to deal with such a pathetic sissy who can't wear her heels while addressing her Mistress...."
20. Paint head of sissy clitty with nail polish of Mistress choice Hehe....nice
21. Rub ben gay on nipples and head of penis, and edge number of times Mistress desires Or you can use Icyhot...and rub it on the shaft too...you know this will hurt, right?
22. Edge and spank sissy clitty with a ruler number of swats Mistress desires Perfect punishment add a plug to your sissy hole during the session and I will be watching.

Guilt, Shame, or both

Cross dressing has been a part of my life for many years, I love the feeling of the silky fabrics, the hug of the spandex, and the girly feeling of not having to be in control. The dressing controls me, and the irresistible urge to masturbate and orgasm grow until I finally give in and begin slowly caressing my sissy clitty. That name sissy clitty, doesn't sound masculine at all, actually down right sissy and submissive. How can anyone with a sissy clitty even have a masculine thought. It causes my sexual tension to build even further. As the sensation continues to grow my ministrations increase and the sissy clitty swells to it's fully excited state, and then it happens, the pulsing, surging, wave of energy overtakes my sissy clitty. And it's over. I am now lying there with a limp sissy clitty, exhausted, and wearing very feminine, clothing. The same clothing that just a few minutes ago gave me so much pleasure now gives me so much shame and embarrassment. Inexplicably begin to remove the clothes to remove my embarrassment and even sometimes shame. If only I could leave them on and be forced to meet my sissy desires and embrace them for a longer time. I frequently long to have someone controlling me at this point in time. Forcing me to remain dressed, forcing me to admit my true state as a sissy, forcing me to face my embarrassment and embrace my predicament. Punishing me by making me own up to being a cross dressing sissy and own up to the my true desire to remain dressed and just punishing me to prove I am not in control and proving my need for a dominant woman. If only.

From the beginning

Most of us crossdressers started out very early. Lacy is no exception, I vaguely remember being 8 or 9 and checking out mom's underwear drawer. For some reason it held a special mystique, I remember seeing all the pantties, girdles, bras, and of course the stockings that every woman wore in the sixties. I really do remember being able to see all those stocking clad legs as a small boy and wondering what it felt like to wear them. But other than a peak in the drawer I never really got a chance until about age 11. There were pairs of stockings hanging up on the line in the basement to dry, sneaking a pair from the line I stuffed one in each pocket and went upstairs to my bedroom. After everyone in the house fell asleep, the stockings came out for an adventure. I removed my pajamas and underwear and began to roll the stocking up just like I had seen in the movies and slipped it up my leg pulling it all the way up my thigh. It was fantastic, so I slipped the other one on and it was twice as fantastic. Then it happened, something rose to the ocassion. Stroking it the feeling grew and intensified, then it happened, my first orgasm wearing women's clothing. It felt good, really good. Was this normal, if it feels this good it has to be. If I had only known what the stage was now set for.

Mistress Christine's controlled sissy

Well lacy has finally found the the one Mistress who would consider taking control of lacy. Mistress is pretty, intelligent, and dominant. What a combination. I am just so excited, and nervous. I just don't know why but I really long to have her control me, my orgasms, masturbation, shopping, dressing, assignments, punishments, and my sissy training. The thought of being controlled and not being in charge of my orgasms and even my own sissy clitty is scary and exciting, never knowing what she will have me do one minute to the next. Mistress Christine is absolutely beautiful. I love to dream of being in her presence and begging her to use me for her pleasure. She grabs me by the ears and forces my mouth toward her moist and precious femininity. Of course my hands are tied behind my back and my own sexual desires are heightened as my sissy clitty responds. If only I could do something with my sissy clitty, but alas Mistress isn't ready since lacy must serve Mistress needs first. Maybe after several orgasms pity will be directed toward lacy and Mistress will allow her some type of humiliating and painful relief.
If only.........