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Lady is always on the lookout for more ways to give me pain/pleasure. One day She was looking in the medicine cabinet and notices the collection of prescription bottles from Target Stores. These bottles are red with a color band identifying who in the household the prescription is for. Why i saved all the empty container i am living to regret.

She held one up and said, “Look maid, these rings are bigger than your clitty. Here, put one on.” She was right, with my flaccid little man-toy the ring could be pulled over the head and down the shaft.

“Oh, that is so cute; look we have more. Lets make it a game. There are 10 bottles. I want you to put each ring over your tiny thing. If you fail to get them all on in say, 5 minutes, each one left over will be 10 swats with a tool of My choice.”

The challenge did not seem to hard, after all, i easily put on the first one. But much to my dismay, my neglected sissy clit had not been fondled in quite some time, and as i pulled each ring over the head, my penis began to grow. After just the third one, it was already very difficult to slide the ring on; the fourth was near impossible, but i got it on. Try as i might, the head had swelled to look like a mushroom and i could not get the fifth ring on. As i was now dripping with my own juices, i tried to lubricate the ring, but my cockhead was getting more sensitive by the second and continued to grow. The four rings already on my penis were beginning to get very uncomfortable as my flesh bulged between the rings. The more i tried to slide it on, the more it grew.

Lady was quite amused. “Look at that silly thing. Times up. Bend over”

I began to sob as the first of 60 swats hits my backside.

Tags: Cock Torture Humiliation Spanking Sissy

When my Lady took control of my life there were many changes and adjustments i had to make. Of course there was the ritual of clothes disposal: all my male underwear (except to one pair my Lady kept locked away “for emergencies”) was given away. A lock was installed on my closet door, so that i could only get to my male outer ware when Lady deemed it appropriate. My credit cards were surrendered and my paycheck was mailed to a PO Box She controlled.

Since i was taking over all of the domestic duties, there was no need for my once a week housekeeper, Linda, to continuing coming to the house. So i had to terminate Linda after nearly ten years of loyal service.

Adjusting to being the wage earner as well as the maid was difficult. There were many days when i returned from my management job with no energy to make dinner, clean the house and service any other needs Lady might have.Needless to say, after a few months i began to fall behind in my cleaning. The range hood, under the cabinets and other hard to reach places began to accumulate dust and grime. My mopping, dusting and vacuuming all became rather haphazard.

“I don’t know why you cannot do a better job” Lady exclaimed. Corporal punishment had little impact as She soon realized how much i looked forward to having my backside struck with a crop or paddle. Lady bought me a variety of uniforms. i had a few conservative maids' dresses that you might see being worn in a formal hotel, i had some pastel pants suits that might be worn by staff in a cheap motel, and of course i had some very sissy French and English maid’s dresses.

Each day, Lady would indicate what uniform i was to wear. One day She told me to select the sluttiest French uniform i owned. This was a sissy pink dress with matching crotchless rumba pants. Then She filled me with a butt plug with a string of sleigh bells hanging off the end. A pink ribbon leash was tied to my cock and pulled up my asscrack and out the waistband of my bloomers; this too had sleigh bells fastened. All of my aprons had a pair of grommets in the ties so that once a padlock was locked in place, i could not remove the apron, and of course, the dress underneath. Finally pair of thigh-high “go-go” boots with 6 inch heels was zippered on my legs. The shoes also had grommets that were locked to the top of the zipper pulls.

Now, i had been dressed like this before, but it was a uniform usually saved for serving at one of Lady’s many cocktail parties. i thought it a bit odd that i was dressed for formally so early on a weekday.

“I have had enough of your sloppy housecleaning. Nothing I do seems to have any effect on your lazy habits. I have you dressed in your finest outfit, because today, I have a special guest coming to teach you how to do your job.”

i had no idea what Lady meant, but i did hate housework.

The doorbell rang and Lady ordered me to answer it. When i opened the door i was so shocked to see Linda, my former house cleaner standing there. i blushed so many shades of red and purple. Since my surrender as a sissy i had been seen by many of Lady’s friends, but never had anyone from my past ever seen me like this.

“I asked Linda if She could help Me teach you the proper way to keep this house in order. So for the rest of the day you will report to Her.” i was still dumbfounded at seeing someone who had once worked for me, now assigned to be my teacher. i could barely utter a “Yes, my Lady.”

“Linda was so kind; She is not to going to charge us for your education.” Now, i had known Linda for many years, and working for free was not in her nature. “you will pay back Linda for Her assistance by helping Her with some of Her jobs. Linda is going to give you some invaluable on the job training at Her client's homes" "Hurry along, you need to help Linda finish her rounds so you can get back here and show Me what you've learned."

i followed Linda to Her car, my bells ringing as i sashayed along in my 6 inch heels with mt facial cheeks still glowing crimson.

So that was it. i was now reduced to being the assistant to my old housekeeper. This is my greatest humiliation: scrubbing toilets while Linda sits watching television.

Tags: Humiliation Sissy Maid Humiliation

Sensitivity training Lady uses the DVR to record shows She would like to watch at more convenient times. One day i recklessly commented on how dumb one of the shows was. She was furious. “I am going to teach you to be more sensitive to My needs and wants.”

With that She began to collect some of Her tools. Soon i had my hands tied to an over door hook where i had a clear view of the television. She then forced my feet into 6” heels and spread my legs apart with a short length of pvc pipe (economic spreader bar) and sisal rope.

“Now, let Me show you some sensitivity.” Lady squeezed a pair of snake bite suction cups on my little tities. Then She squeezed again to expel more of the trapped air; this had the effect of pulling my nipples further into the cups. Next she tied a ½ pound lead weight from the local fishing store to my balls. “There, that should last until the next commercial break.”

The pain was already spreading over my body. my toes were being squeezed together into the points of the narrow pumps. my ankles were arched and contorted beyond imagination. my knees ached from rough texture of the rope and the spread of my legs. The weight hanging from my balls and the suction on my nipples confused my senses. What else could She have in store?

It did not take long to find out. The commercial interrupted Her show. Usually She would fast forward through the breaks, but not today. Lady walk up to me and squeezed the snake suction cups again. my nipples burned as they were sucked deeper up the cups. Then She hooked another weight to my balls. “This is what I will do each time my show is interrupted. You should be glad this is only an hour show, probably only 5 commercial breaks.”

Tags: "nipple Torture" Nipples

Another sissy shared the joy of squeezing into tight restrictive girdles and long line bras. i too share this love.

As a child i snuck my mother's girdles, then too big, and would sleep soundly. As i grew older, the girdles fight tighter - oh heaven.

Then there was the fateful week when a slender neighbor Lady asked me to care for Her garden while she was out of town.

WOW, i thought to myself, as thin as She is why does she need all these girdles and corsets. Of course, they were far more lacy and frilly than the utilitarian garments in my house. What a week!

I would water Her plants as often as i could. But of course, once i turned on the sprinklers i made a mad dash to Her bedroom to pour myself into Her lovely undergarments.

Sometimes i would wear multiple layers. They fit so tightly against my sissy clit. i would wear Her longline open bottom girdles (OBG) low on my legs so that i could barely walk.

And how could i contain myself; like a bitch in heat i rubbed my tucked under clitty against the sofa armrest until i blasted my joy juice into the crotch of Her pantie girdle.

When the weekend neared i began to panic. Her girdles, corsets, garter belts, stockings and bras were all over the living room. i had multiple problems. i did not know how to wash these delicate items (or anything else for that matter, Mom always did my laundry). i could not remember which pieces came from which drawers. And to top if off, there were cum stains on the armrest i had regularly humped. She was due home on Sunday so Saturday i began my cleanup effort. i started by sorting the frilly garments by type. But the temptation was too great; i needed to feel these wonderful slices of heaven one more time.

i carefully selected the pieces i would wear. Then i gently pulled each item over my eager body. Pantie girdle, OBG with garters, stockings, corselette - i knew all the names from my research in the Sears and Montgomery Ward catalogs. Baseballs filled out the top. Once attired i began my ritual on the end of the sofa. Oh, yes, this was good. i was so wrapped up in my ecstasy than i did not hear Her enter the room through the kitchen.

"What the hell!", She shouted, "what are you doing?" i could only do what came naturally- i began to cry. "Stop bawling you sissy. I am going to make you pay for the damage you have caused."

But that is another story.

Tags: Sissy Girdle Humiliation

My Lady has me sort my panties into three groups: discreet, real sissy and embarrassing.

 

Category 1: “Discreet” panties are usually solid color with a scalloped waistband (VS) or just a touch of lace. Some of these are so subtle that i can wear them to the doctor’s office or gym. But close inspection will let anyone know these are not men’s underwear.

 

Category 2: “Sissy” panties are usually pastel floral prints and patterns that no self respecting male would ever wear. Included in the category are panty girdles and control thongs.

 

Category 3: “Outright embarrassing” panties have heavy lace decorations or ruffles or very bright floral prints or solid colors. Some of my bikini bottoms are included in the category. But there are also long leg girdles, open butt girdles, padded panties and rumba panties in this collection

 

In the house, i am always dressed in category 3. Everyday in the vanilla world, i usually get to wear Cat2’s. Category 1’s are reserved for those times that I will need to show my panties, like the afore mentioned visits to doctor and gym.

 

When i have crossed my Lady, I am forced to wear Cat3’s out of the house. These can clearly be identified under men’s clothing, especially under the thin linen pants i wear when out. (i am never allowed to wear anything as masculine as a pair of jeans). The crotch liner stitching can usually be identified as well.

 

On a recent outing to Las Vegas, i answered back when Lady told me to put lipstick on when entering the hotel. WOW, was She angry. When we got to the room, She locked my Cat2’s in the suitcase. If i chose to wear no underwear, people could easily see the outline of my chastity belt, so i needed some cover. There was no doubt that i was wearing flowered panties under my thin white linen pants. I did the best I could to not make eye contact with anyone the entire weekend.

Tags: Panties Humiliation

It is embarrassing to so shopping for something macho like men's athletic shoes when wearing fish net or patterned stockings .

 

Most days Lady has me wear "decorator" stockings with no socks to hide my sissyness. The worst of these stockings are white with red hearts, but many have floral prints knitted into the fabric.

 

When we go shopping for lingerie she usually holds up panties to my waist to "see if they will fit", but sometimes she will ask the clerk, "Do you think this will fit him?"

 

Another assignment She often gives me is to return an item. She hides within hearing range and i am to say to the clerk,"i need to return these, they do not fit me."

 

She keeps threatening me that i will be sent to the dressing room with some dresses to try on. This has not happened yet, but She is always teasing me this will happen as soon as She finds the right store.

Tags: Shopping Humiliation

Lady said i need more shoes. i dreaded going to the mall and trying on shoes, it was always so embarassing. i whined and even started to cry. Lady then offered me a compromise.

 

If i would wear my chastity belt 24x7 for one week i could order shoes on-line. I quickly agreed.

 

When the seventh day came around, Lady and I begin to browse the Payless shoe site. We decided on 4 pairs, 2 styles of MaryJanes, a wedge, and a ballerina flat.

 

But then came the proclamation that since i refused to go to the mall, i would be kept in chastity until the shoes arrived. Okay, that was only a few more days. Since i was unsure of my size in their styles, Lady suggested i buy three of each, one larger and one smaller as well as my usual size 12.

 

i gladly paid the rush shipping fee and prayed there would be no back orders.

 

Three days later the shoes arrives, all 12 of them (4 styles, 3 sizes each). Lady released me from my chastity and had me bathe and shave my legs.

 

Lady ordered me put on a fashion show, requiring that i wear a different dress or uniform with each. I modeled the Mary Janes wearing two of my maids uniforms. To show off the wedge espadrilles, i pranced around in a one piece floral bathing suit. And finally i wore a white leotard, tights with a pink tutu to model the ballerina flats. They were all so nice. The heels of the mary janes would surely cause me some discomfort as i did my chores, so I selected the larger size. The wedge and flats fit fine in size 12.

 

i started to box up the 8 extra pair when Lady stopped me cold. "What are you doing?" You have tied up my credit card with 12 shoes and rush charges. You need to return these shoes directly to the local Payless."

 

Lady is very petite and has a very small foot. When I walked into the store, surely the clerk would know they were not Hers. I was allowed to put on some slacks and a generic looking polo shirt over my panties, bra and stockings. As was our custom when leaving the house i was allowed to remove my breastforms from my bra.

 

Things did not go well at the store. The clerk was friendly and helpful, but needed to call the manager to approve the return. I stood there, rather red-faced as other customers came in. i was sure they could see my bra straps under my shirt. After what seemed like an eternity, the manager came over to complete the paper work. He (yes, it was a male manager) looke at the stack of very large sized shoes, glanced at Lady and then looked me up and down. i could sense his disgust at this sissy standing in front of him. He asked me outright, "what is the reason for return?" i tried to sink into the floor, my face turned crimson. i looked at Lady, and She said, "go on, tell the nice man why you are returning the shoes." i whispered, "because they don't fit." The thoughtful manager asked me to repeat what I had just said as he could not hear me. Twice more i squeaked, "they do not fit.". "Perhaps the customer could come in and try on the proper size" he said, with a knowing look of contempt. Lady jabbed me and said, "please explain the situation to the gentleman." By now a line had formed by the register as a few ladies were impatiently witing to pay for their purchases.

 

i know this was the moment of truth; if i ever wanted to get out of the store i would need to explain. "These shoes do not fit ME and i already have the correct size at home." A hush fell as the women behind me stared at me. One started to giggle and then they all begin to laugh. The manager calmly completed the paper work and then had a final shot, "perhaps next time the gentleman could simply come to the store and try on the shoes."

Tags: Shoes Humiliation Shopping

Oh, its almost that time of the month.

 

To prepare Lady has me go on a liquid diet. Last night i was subjected to consecutive enemas until i was truly clean. Being ever so kind, Lady allows me to decide when i am clean enough; She tests my thoroughness by allowing me to drink 12 ounces of the clean discharge. Today i had tomato soup for all of my meals.

 

At midday i heard Lady complaining about Her cramps. i knew it would soon be my turn to share in Her discomfort. Lady ordered me to prepare a 10 ounce bulb enema of straight lemon juice. Then She gleefully squeezes the bulb as hard and fast as possible. Next She pushed a chunk of peeled ginger up my pussy hole and held it all in place with a super tampon. But She was not done yet. Lady had a collection of padlocks from some of our play sessions and She locked them on the string hanging out of my pussy hole.

 

The figging ginger was doing its thing; my hole was on fire. The straight lemon enema was inducing some fierce cramping. And the weight of the padlocks hanging between my legs required me to clench my cheeks as tightly as possible to keep my tampon from pulling out. Wow was this uncomfortable.

 

Still more. Lady stuck a pad on my little clitty penis and another to the soft spot at the opening of my pussy hole. Then just as the effects of the ginger were beginning to subside She powered on the massage mouse (a mild electro play toy) sending tingles from one side of my body to another.

 

i was nearly doubled over from all of the sensations and the cramping.

 

“Well, sissy, what are you waiting for? Get dressed and back to work.” i limped to my room and put on my French maids uniform, including a triple petticoat. When i started to pull up my French knickers Lady slapped me sharply. “What do you think you are doing, you will interfere with your little swinging pendulums.”

 

So here i am, properly dressed without panties and a bunch of padlocks swinging between my legs. The cramps are so severe, i can barely move. Oh, it’s Thursday – the day i mop the floors. It is all i can do to hold the tampon from falling out. The rhythmic jolts shooting from front to back have me almost in tears. From the other room i hear Lady curse, “oh the second day is always so much worse.”

 

The house was nearly cleaned, it was taking me so much longer than ever. The way the damn massage mouse was positioned, on my little penis and near my pussy hole, the severity of the stimulation would vary depending on how i was moving. Sometimes it was really intense, shocking me upright. All the while i need to keep my cheeks clenched so tightly to keep the weight of the padlocks, latched on to the string of my tampon, from pulling out.

 

In the distance i could hear Lady waking from Her nap. “sissy, I think We need to be changed.” This a standard ritual.

 

First i prepared the throne. i covered a dining chair with plastic wrap.

 

Next, Lady would stand in front of the chair and i would gently remove any clothing that might interfere.

 

Then She would take Her place on the throne and i would kiss Her feet and lick the soles clean.

 

i would tug on the string of Her tampon with my teeth, being ever so carefully so as not to mess Her thighs anymore than necessary.

 

my tongue would clean Her so there was no trace of Her Womanhood. Of course any drops on the chair would also need to be licked clean.

 

Lastly i would take the used item in my mouth and transport it to a dish by my bedside where it would be saved until next month.

 

This was not something i enjoyed, but of course any complaint would be severely dealt with.

 

Lady then dressed Herself after inserting a fresh tampon.

 

But what about my situation? This was the first time i was forced to endure these cramps. The ginger had long stopped burning, but the lemon juice induced cramps were mounting.

 

“my Lady, might i be so bold as to ask permission to change my tampon?” She glared at me and said of course. Foolishly i believed that i would remove the tampon and relieve myself of the lemon juice. “Bring another bulb of lemon juice.” i nearly died, the cramps were already so severe i was on the verge of tears. “And also bring an oil Fleet.”

 

We had stocked up on mineral oil Fleet enemas . They were the messiest thing, oil would trickle out of my pussy for days and form an unsightly ring in the toilet.

 

“Give yourself the Fleet then finish off with the lemon juice,” i was ordered. i was trembling as i removed my tampon and replaced it with the first nozzle. Some leakage occurred as i pushed it in. The lemon juice really filled me up. The pressure on my pussy was really painful. “i sense you might have a heavier than usual flow, you had better use a napkin instead of a tampon.” Ugh, this means i will feel my menses flowing out of me as i go about my chores. To be safe Lady allowed me to wear a sanitary panty to catch any drips.

 

i wonder how much worse things will get tomorrow.

.

Tags: Menstruation Cramps Humiliation

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