I meet Dr. Inga Hatfield
It was Friday evening when I returned home to find not only my younger second wife, Christina, but her man hating friend, Greta, and a third woman, a stranger, in our living room. I really didn’t like Greta but didn’t want to start a row with Chris, so I smiled pleasantly and said, “Good evening, all.”
All three women stood and Chris said, “Charles, this is Doctor Inga Hatfield.”
I turned to the doctor and was about half way through saying something like, “Nice to meet you doctor,” when the woman punched me in the stomach. Unprepared for the blow I doubled over and felt her grab my hair and yank me forward as Greta stuck out a foot and tripped me. I slammed to the floor with the wind knocked out of me and felt someone, the doctor as it turned out, sit on my shoulders. Greta dropped down on my butt and Chris, my dear sweet wife, grabbed my ankles.
I was trying to get enough breath to protest when the doctor pulled my head up and back by the hair and stuffed a ball into my open mouth. She quickly and efficiently buckled the straps around my head silencing me, at least as far as any intelligible sounds.
At the same time Greta captured my hands cuffing them behind my back and Chris wrapped what I later learned was a Velcro strap around my ankles. A second strap just above my knees and I was helpless and immobile.
Inga, the doctor, got up and resumed her seat on the couch where she could look at me. She began to speak to me while I felt my shoes and socks being pulled off and my suit coat being sliced up the arms, presumably by Greta. As she spoke my pants legs were being slit, probably by Chris.
The doctor said, “You have been a miserable excuse for a human being and we are going to see that you pay for your crimes. You will no longer be able to abuse and rape women.”
I tried to protest that I had never abused, or raped anyone and, although I couldn’t speak, I must have made enough noise that she must have understood. She began to list my ‘crimes’ saying, “Do you remember Helen Robinson? You sexually harassed that poor woman until she had to leave her job and move out of town. You had to pay her $10,000 to keep her from suing you.”
That made no sense at all. Of course I remembered Helen. She had been our chief accountant and one of the company’s earliest employees. Her leaving had nothing to do with sexual harassment. Her fiancée had been offered a promotion into a job 300 miles away and they had decided to marry and begin to raise a family. We had given her the $10,000 both as a sort of bonus for her years of service and as a corporate wedding present.
“Then…’ continued Inga, “… there was the barmaid who got pregnant and had to leave town.”
I had no idea of who she was talking about. I suppose there may have been an illegitimate pregnancy in town but I had never been with another woman since my marriage. As I was wondering what she was talking about Chris pulled away the rags that had been my trousers and Greta did the same with my suit coat. Then she began to work on my shirt while Chris attacked my boxers.
Inga continued, “Then of course there was the despicable rape of your wife’s best friend.”
This was nonsense. Greta was my wife’s best friend and, while she was physically an attractive woman, her attitude, especially toward men, had meant that we didn’t even like each other. I had never even flirted with her. I certainly hadn’t raped her. Greta’s silence seemed to confirm Inga’s accusation however.
“Shall I tell you what we are going to do to you?” Inga asked angrily. Of course I couldn’t answer her rhetorical question but she continued.
“We are going to castrate you and turn you into a simpering sissy boy, a creature that is neither male nor female, and fit only to serve as your wife’s submissive sissy maid.”
At this point she interrupted her diatribe to give Chris and Greta some orders concerning my now nude body. “Plug his anus and then roll him over so we can get him ready for the trip.”
I felt something cold and rubbery pressed against my rear and tried to clench my sphincter muscles. I heard my dear wife laugh as she said, “The tighter you clench the more this is going to hurt.”
There was an increase in pressure and the plug or dildo or whatever it was, was shoved painfully into me. Then Chris and Greta rolled me over so I was lying uncomfortably on my cuffed wrists. Inga said to Chris, “Watch him while Greta and I get the backboard and gurney out of the truck.”
Greta and Inga left on their errand and Chris, the woman I had thought was my loving wife knelt beside me and twisted my head so that she was looking into my eyes. She said, “I know you didn’t do any of those nasty things but we had to convince Inga. I thought of just divorcing you, but the pre-nuptial agreements we signed are very well drawn. This way you will just disappear and it will seem as if you deserted me. I will be able to gain control of all of your assets with little or no fuss. Besides, Greta has convinced me that it will be fun to have a little sissy maid to do all the work around here. And you, darling, are going to be that creature. Wait till Inga gets back and tells you what we have planned for you.”
Chris rose and went back to her glass of wine as Greta and Inga wheeled in what appeared to be a hospital gurney with some sort of rigid yellow board in the basket.
“Can you tell him the whole plan? “ Chris asked Inga.
“Well…”, she responded, “…I can, but by the time we are done with the operations, the brainwashing and the training, his mind will have been so shattered and rebuilt that he won’t remember anything we tell him now.”
“I know.” said Chris. “Still it will be days before you get to the clinic and it would be fun imagining his fear as you travel.”
“You have a nasty streak. I like that.” laughed Greta
“Let’s work while I tell him. Here, help me roll him on his side and slide the board under him.” Inga said.
As they rolled me on to my side, slid the board under me and then rolled me back onto the board, Inga said, “Listen up sissy. This is what’s going to happen. Once we have you secured to the board and in the gurney we will load you in my truck and head to my clinic. That will take about two days.”
As she talked they loosened the strap around my knees, pulled them apart and strapped them to the board. My ankles followed as Inga, said, “Once we get there you will undergo a whole series of surgical procedures. I’ve already told you that you will be castrated. We will also insert rings in the head of your penis and your perineum and lock your penis back between your legs. That will ensure that you have to sit like a girl to urinate and will also ensure that if your body tries to get an erection, it will not only be impossible, it will also be painful.”
Turning to the women she said, “Pull his arms out from under him and secure the right wrist and elbow. Then use the chest and hip straps before you take off the handcuffs.”
As Chris and Greta complied she turned back to me and said, “We are going to cut your Achilles’ tendons and shorten them. That will ensure you can no longer place your heels on the floor. You will need at least three inch, and perhaps even four inch, heels to be able to walk.”
She glanced at the women and said “Now pull his left arm out from under him and tighten the chest strap. I will help you control the arm until you have the wrist and elbow strapped down.”
“That’s not all sissy.” Inga continued. “Do you know what liposuction is? We liquefy fat cells and suck them from the body. Except in your case instead of discarding them we will inject them in your hips and buttocks to give you a more feminine shape. Your chest will get breast implants. Your chest skin probably won’t stretch enough to properly cover them so we will do skin grafts, probably from your thighs, to enclose your chest. We will open your neck and shave down the thyroid cartilage surrounding your larynx. That’s what you would call your ‘Adam’s apple’. At the same time we will tighten up your vocal cords which ought to make your normal voice about an octave higher.”
As she spoke she strapped another band over my forehead. Then she had the three of them lift my immobile body into the gurney. Opening a bag she withdrew a long tube and inserted it into my penis. “Catheter.” She explained to the women. “I don’t want any smelly mess while we travel.”
Once the catheter was fully in she inflated the balloon and gave a nasty yank to ensure it was fully seated. The collection bag was placed between my slightly spread legs. She slid two thin tubes up my nostrils and past my sinuses, explaining that this would ensure I could breathe even if I got a runny nose.
Then she unbuckled the gag. I was prepared to tell her that I hadn’t done any of the misogynistic things my wife had accused me of doing, but as she pulled the gag out she gripped my jaw holding it open and inserted a larger tube. This she pushed down my throat ignoring my gag reflex and apparently directly into my stomach. “This is his feeding tube. It will remain in place for the next two months, as we complete the operations and his medically induced coma. It will allow us to send the necessary nutrients as well as the female hormones directly into his body.”
“Oh that’s right sissy. I hadn’t finished telling you what’s going to happen. Let’s see, after the neck operation there will be a few cosmetic things. We will weaken your jaw line, emphasize your cheek bones and shorten your nose. Of course we will use a laser to permanently remove body and facial hair and to thin your eyebrows.”
“All in all, the surgeries will take about a week and a half. But the surgeries are only a part of the changes. We are going to take apart your mind and then fill it with tapes reminding you of your crimes, your need for remorse and penance by serving your wife as her personal sissy maid. “
“Do you know how we will take apart your mind?” Inga asked rhetorically. “We are going to use pain. Pain so all consuming that you will not be able to think coherently. Your only thoughts will be how to stop the pain. To do this some procedures will be performed while you are awake and without any anesthetic. For example, your castration will be with a scalpel and then the wound will be cauterized with a hot iron. Very simple, medically effective, and a method proven safe for hundreds of years. Still it will be very painful. Other procedures will require anesthetic but when you wake there will be no medication for the pain which will gradually consume you for every waking hour inhibiting your brain from any rational thought.”
“Then after the completion of the surgical procedures we will place you in a medically induced coma for the next six weeks. This will allow your body to recover from the physical shocks and we will administrate pain killers that will leave your mind open to suggestions which will be fed through ear phones. In the coma you will feel no pain and you mind will associate the suggestions with the blessed absence of pain, making you very susceptible to our suggestions as to the need to be submissive to your wife and serve her every whim.”
“In about two months you will have recovered enough to be brought out of your coma and we will begin your training. Your body balance will have changed and you will not be able to walk without the support of high heeled shoes so the first morning will be spent on how to stand, walk and sit. You will be clumsy at first but you will be punished for that and will improve. In the afternoon your training will include how to provide manicures and pedicures. You will practice on your own hands and feet as your nails will have lengthened substantially in the two months.”
“Then in the evening you will have your first training in cunnilingus. Your wife said you had some experience in this area but we will ensure that you practice on every woman in the clinic so that you sense the different reactions of different women and become expert on satisfying any woman.”
“In a few days when you have learned to move gracefully we will teach you how to dress in women’s clothing and how to use minimal makeup to enhance your face. Your hair will also have grown so we will have it trimmed and styled and then give you lessons in caring for long hair. Of course errors in these lessons will bring painful punishments.”
“As you learn these basic skills other training will be added. You will learn how to dust, vacuum, scrub floors and polish furniture. Laundry training will include separating colors and whites, treating spots, hand washing delicate items, ironing and stripping and making beds. There will also be cooking lessons though here we aim for basic competence rather than the perfection demanded in other classes. There will be classes in serving meals and removing courses and serving away from the table be it coffee, wine or mixed drinks. Of course cunnilingus training will continue.”
“We estimate about a month to bring you up to a standard that will please your Mistress/wife. Then you will be brought back and begin your life as a submissive sissy boy servant.”
Sissy training – day 1
I can’t remember much about the trip except that the inside of a truck’s roof is very boring. Each evening Inga would appear, lower the end of the gurney so I was at an angle, and pour something into the feeding tube. I had no way of knowing what it was. The tube prevented any sense of taste or swallowing but I could sense a certain feeling of fullness in my stomach. I would be left at the angle overnight and raised back to a level position the next morning.
Similarly the next two months or so are pretty much a blur. I remember intense pain when Inga sliced through my scrotum and even worse pain when she cauterized the wound with a red hot iron of some sort. After that I only remember continuous pain driving me more or less insane. Then there was a gentle period when the pain had stopped and soothing voices spoke to me but I can’t seem to remember what they said.
My memory seems to begin again when I was sitting propped up in a hospital bed and a very attractive young woman told me “It’s time to wake up, sissy. Swing your legs over the side and beg me to let you wear your pretty pink sissy shoes.”
I said, “Look there has been some sort of mistake here. I didn’t do the things my wife said I did…”
I was going to add and I shouldn’t be here but she jabbed me with a long rod with a forked tip. As it touched me I received a strong painful electrical shock. I realized that she had used a cattle prod on me. I also realized that my voice was higher pitched and that something in my mouth interfered with my pronunciation. It felt as though there was some sort of stud in my tongue.
I didn’t have time to think about my voice or what was in my tongue as the woman said, “All you sissies try to deny who and what you are. No one here is going to believe you and if you speak without being asked a direct question you will be punished. Now, beg me to let you wear your pretty pink sissy shoes.”
I gingerly swung my legs over the side and saw her holding a pair of bright shinny pink high heeled woman’s shoes. They had a silly looking pink bow on the front and thin stiletto heels at least 4 inches long. I guess I didn’t beg soon enough because she lifted her other hand and jabbed me with the cattle prod. The shock focused my attention as she said, “I said, beg me to let you wear your pretty pink sissy shoes.”
I didn’t want to wear the ridiculous shoes so I slid forward and tried to stand barefoot on the floor. As my weight came down my legs became very painful and I found that I had to stand on the toes and balls of my feet. Trying to lower my heels toward the floor caused intense pain in my ankles and calves. My trainer gave me a moment and then jabbed me again with the cattle prod. She reiterated, “Beg sissy!”
It took two or three jabs and more pain before I surrendered and said “Please let me wear the shoes.”
Another jab and more pain and she asked, “What shoes sissy?”
“The ones in your hand.”
More pain. “We can keep this up all morning sissy. You have to beg to wear the pretty pink sissy shoes.”
It was then that I gave in and asked, “May I wear the pretty pink sissy shoes?”
Another jab and more pain. “I didn’t say ask for them, I said beg for them.”
“May I please wear the pretty pink sissy shoes.”
“That was OK but you should address all women as Ma’am.” she said, handing me the shoes and a pair of small nylons that covered only my foot.
I sat on the bed and pulled on the stockings and the shoes as my trainer went to a chalk board and drew two slashes. I was to learn that those slashes were essentially demerits which would be punished at the end of each session of training.
As I buckled the ankle straps she said “Those buckles have holes so they can be padlocked on but we don’t need locks. With your legs you can barely stand without the shoes. ‘It’s a shame to waste the holes in the buckle so let’s put these on.”
‘These’ were two small round bells with hooks to attach them to the buckles. Not wanting more pain I did as she instructed and she smiled and said, “Now you will make a little tinkle noise as you walk. How appropriate for a sissy.”
At her command I started to walk up and down the room. I found that with my altered body shape I was unstable and tended to go from side to side just catching my balance and ringing the bells. The trainer ordered me to take shorter steps and to place on foot in front of the other so that my hips moved. I was to learn to glide rather than stamp. From time to time she jabbed me with the cattle prod and when she thought I wasn’t trying hard enough she put more slashes on the chalk board.
When I had the basic walk down pat, she had me place my arms at my sides with my wrists bent so that my hands were parallel to the floor. This made my shoulders swing in time with my hips and gave me a ‘proper sissy’s walk’. Of course this also made my ‘boobies’, as the trainer called them, swing from side to side.
She thought this was very amusing but did tell me that a brassiere would reduce the swing. At the same time she warned me that comfort for a sissy was not a key element in the decisions made and that the clothing I eventually would be allowed to wear would probably be uncomfortable.
After what seemed like long hours the trainer, apparently satisfied with my basic walk, produced a rather ugly short pink skirt trimmed with lace and hung with more bells. I was instructed to beg to wear the ‘pretty pink sissy skirt’.
Remembering both the pain and the outcome of the dispute over the shoes I asked, “May I please wear the pretty pink sissy skirt?” This got me another electric shock as I had forgotten to address her as ‘Ma’am’. I corrected this and ‘properly’ begged to be allowed the skirt.
I learned how to step I into the skirt, which is no mean feat when wearing 4 inch heels. Eventually I was able to raise the skirt to my waist, fasten the button and pull up the short zipper. Then it was back to walking to the accompaniment of the bells.
The trainer then had me sit down. I had to stand and sit again this time using my hands to smooth my dress under my bottom. I thought I had done this as instructed but the trainer told me it was clumsy and added a stroke to the growing tally of demerits. I was to sit up straight with my shoulders back and my knees together while swiveling both legs to one side.
It seemed, however, that I leaned forward too aggressively to stand up and sat down too heavily. Both of these lacks of graceful movement earned me shocks from the cattle prod and strokes on the chalk board.
From time to time she would have me walk around the room before seating myself. Occasionally I would fail to remember to keep my hands in the proper ‘sissy position’ and earn another painful shock and a demerit on the chalk board.
Eventually lunch time approached and the trainer picked up a hair brush and sat in the chair and told me to get across her lap. Apparently I was to be spanked twice, once on each cheek, for every demerit on the chalk board. I tried to back away but the trainer jumped up and grabbed my arm, twisting it up behind my back and steering me to the chair.
I was astonished at how easily this young woman overpowered me. She laughed at my consternation and said, “Your muscles have atrophied over the months you have been bound and in a coma. Your diet and chemical regime are designed to keep you weak and helpless. All the new sissies try to use strength and they all fail. Attempting to fight a woman is strictly forbidden, as we are all superior to you sissy. After your spanking, you will be caned for having tried.”
Across her lap with one arm wrenched up between my shoulder blades, my trainer proceeded to lift the hem of my skirt exposing my bare buttocks. I can’t express how humiliating it was for a grown man to be handled and spanked by a young woman. Nor can I find words to adequately express the pain she caused with her hair brush. Apparently the injection of fat cells into my buttocks had stretched the skin and made it more sensitive to spankings.
I had apparently accumulated 18 demerits and received 36 hard swats with the hairbrush, 18 on each cheek. Further humiliation came when she made me count each swat and then thank her for correcting me. I was soon shrieking and bawling while I gasped out the numbers and thanked her, but was told that it was ok for a sissy to cry. After all, we weren’t big tough men, we were just sissies.
After the spanking she had me place my hands behind my head and led me to a wall. Holding a coin against the wall she told me to lean forward and hold the coin in place with my nose. Once I was in position she told me that if I moved the coin would drop and she would spank me all over again. Fear of an additional painful spanking kept me in place while she made a telephone call.
Of course I only heard her side of the conversation but she asked someone to have the punishment frame set up in the lunch room. In answer to a question I didn’t hear she said, “No, no trouble at all. We had the usual stupid male ego resistance until he got smart enough to learn that he didn’t like the cattle prod. After that there was the usual male clumsiness but no real disobedience. I need the frame because he tried to fight off the spanking.”
There was a pause and the she laughed and said, “Yes, they are all so predictable. See you soon. Thanks.”
I was taken to the lunch room with my skirt rubbing at the burning flesh of my buttocks. My trainer sat on a chair and had me sit on an unpadded plastic chair at her side. Of course my recently spanked rear didn’t appreciate the hard chair and I squirmed some. She soon used the cattle prod to remind me to sit still with my back straight and shoulders back, my knees together and my feet together and daintily to one side.
We were both served salads by an effeminate man in a waitress costume apparently patterned after that of ‘Hooters’, except that the shirt read ‘Sissy’s’ and instead of tight shorts he wore a brightly colored mini skirt. He carried a try and bent his knees to get down to the level of the table top. I saw the tray had two salads, one with dressing and one without. Of course he served me the plain salad while my trainer got the one with the dressing. Similarly I received a glass of water while she had a darker beverage, probably iced tea.
During lunch she ordered me to take smaller, more feminine, bites and chew each bite thoroughly before swallowing. The cattle prod reinforced those instructions.
At the end of our meal my trainer led me to a punishment device. My ankles were locked to the legs and my hands were cuffed in front of me and then pulled down to floor level leaving me stretched over a waist high bar. My skirt was pulled up exposing my already red buttocks.
The sissy waitress brought my trainer a flexible cane. I heard a whoosh and my buttocks exploded in fire like pain. There was a pause and my trainer said, “You failed to count and to thank me for correcting you so we will ignore that stroke and start over.”
Once again I heard the whoosh and felt the explosion of pain. This time I managed to stammer out, “One. Thank you for correcting me Ma’am.”
This went on until I had counted and thanked her for 25 strokes. I was certain that my ass was shredded and bloody. Then she told the sissy waitress to apply some cream. It felt cold and his hands were gentle but with my penis pulled back between my legs he was soon fondling the tip of my cock.
I’m not particularly homophobic but was disgusted at the thought of this sissy touching me so intimately. I guess I tried to squirm away from his hand which apparently amused my trainer greatly and she was laughing as she told me to, “Stand still!”
I guess the sissy waitress wasn’t supposed to fondle me because as soon as he realized that my trainer saw what he was doing he moved his hands back to my buttocks. I heard the whoosh of the cane and a little gasp of pain from him (her?) as the cane apparently cut across his (or her) exposed thighs.
I was left in my stretched and exposed position for some time as my trainer chatted with other women who worked in the clinic. Eventually I was released and we walked back to the room in which I had awakened. It now appeared that I would live in this room as well as using it as my training room.
I was reminded of the need to stand straight with my hands in the proper sissy position and walk properly with short mincing steps. All of this was reinforced with the cattle prod.
The afternoon’s training had to do with manicures and pedicures. I hadn’t thought about it but both my hair and my nails had grown substantially during the past couple of months since my abduction. I was made to remove my ‘sissy skirt’ and carefully hang it in the wardrobe.
I filled a plastic tub with the appropriate solution and removed my shoes and stockings. With my heel supported on the edge of the tub I soaked the toes of my right foot. When the proper time had passed I took out the right foot and began soaking the left. I doubled my right leg and began to learn how to care for my nails.
There was something called an orange wood stick used to remove dead skin from the cuticles. Then I trimmed each nail and shaped it with an Emory board which is sort of like a stick with sand paper. The final step was the application of several coats of polish. Even this had some tricks as I used cotton to separate each toe. Of course the color was ‘sissy pink’.
The left foot followed and when I was done we moved on to manicure which was essentially the same on the hands. Of course I was pretty clumsy, especially with my left hand, which earned me electric shocks and some demerit slashes.
When it had all dried I had to remove the polish with cotton and remover and then reapply polish. After several repetitions the trainer had me apply a clear gloss coat over the colored polish.
With my completion of the lesson the trainer told me to lie over her lap for my spanking. I didn’t even try to resist as I knew what the outcome would be and I certainly didn’t want another session with the cane.
The spanking hurt and I was crying by the time she finished. Again she had me put my hands on my head and brought me to the wall where she had me hold a coin with my nose. She again warned me that if I let the coin fall I would be spanked again.
I heard some rustling and then my trainer called someone and said’ “We are ready for you.”
A few minutes later I heard the door to my room open and someone in high heels enter. My trainer said, “OK sissy. Take your hand off your head and bring me the coin. Remember to walk properly.”
I turned around to comply and my draw dropped. Dr. Hatfield had entered the room. I hadn’t seen her since the journey but that wasn’t what astonished me. My trainer was sitting on my bed, totally nude. There was a pillow on the floor and she pointed to it saying, “Come and kneel here sissy.”
The woman had a magnificent body and I felt a pain in my groin as, despite my castration, my cock feebly attempted to harden. Dr. Hatfield said, “It is time for your first cunnilingus lesson. I don’t know if you remember but I told you that you would practice on every woman in the clinic. We will start today with Tina, your trainer.”
While she was speaking I moved forward and knelt on the pillow between Tina’s legs. I began to reach up to caress her thighs when Dr. Hatfield said, “Stop!”
Her command was accompanied by a flash of pain. Dr. Hatfield didn’t use the cattle prod but had a riding crop. She flourished it at me as she continued, “Sissies are not be permitted to touch a woman unless specifically directed by their Mistress/wives. For training purposes we will keep your hands behind you and you will learn to sense a woman’s reaction using only your lips, tongue, eyes and sense of smell.”
She moved behind me a handcuffed my hands. For all I knew it could have been the same set of cuffs she had used in my living room the night I had been abducted.
“Begin by kissing her inner thighs”
That began a long session of cunnilingus during which Dr. Hatfield drew my attention to every movement or sound that came from my trainer, whom I now knew to be Tina. She was a brilliant teacher and I found myself focusing on all sorts of muscle twitches or slight sounds that would not have registered with me under other circumstances.
Under her tutelage I drove Tina’s body closer and higher until she exploded in an orgasm that was rather wonderful to watch. Though my tongue was tired and my jaws ached I was proud of what I had been able to do and, in truth, somewhat amused that I had been able to take all control from Tina who had so carefully controlled me all day.
When Tina recovered I was ordered to bring her bra and panties to her. Of course with my hands cuffed behind me I had to use my mouth. My face was already covered with her secretions but she wiped her panties on my chest when she took them.
Once Tina was fully dressed she escorted me to the bathroom and then to my bed where picked up the pillow that I had been kneeling on and placed it on the bed. She then removed the handcuffs and had me take off the high heeled shoes. She tucked me in as one might a very young child and said, “Go to sleep little sissy. We have so much more for you to learn tomorrow.”
Sissy training – day 2
The next morning I woke on my own, slipped on the high heeled shoes and went to the bathroom. I was returning to the room when Tina entered. She said, “Good morning sissy.”
I responded, “Good morning Tina.”
She sighed and walked to the chalkboard where she made two lines for demerits. Looking at me she jabbed me with the cattle prod and said, ”That’s a poor start sissy. First when you came out of the bathroom your hands were not in the proper sissy position. Secondly you didn’t address me as Ma’am. Sissies do not use a woman’s name unless instructed to do so. You are not my equal and do not have the right to speak as though you are. If you don’t remember the lessons you were taught yesterday you are going to have a very sore bottom, sissy.”
I pushed my hands out parallel to the floor in the approved sissy position and shut my mouth.
Tina looked at me and said, “I said good morning sissy. What is the proper reply?”
It was humiliating to think that this younger woman, whom I had licked and sucked to a spectacular orgasm just last night, was so in control of me but I didn’t want more pain so I answered, “Good morning Ma’am.”
We spent about an hour in remedial work with my standing, walking with short mincing steps and then sitting properly with my back straight, my shoulders back, my knees together and my ankles together and to one side.
I earned both an electrical shock and a demerit when I sat without smoothing my skirt. I protested that I wasn’t wearing a skirt. That got me both a shock from the cattle prod and two demerits, one for speaking not in response to a direct question or instruction; and one because, “It doesn’t matter if you are wearing clothes or not. You must make the proper sissy motions every time you sit so that it becomes habitual. A real woman doesn’t have to do that of course but you are nothing but a sissy.”
After she was satisfied that I remembered yesterday’s training, we moved on to clothing or at least lingerie. We began with my begging to wear the ‘lovely lacy sissy brassiere’. As she had intimated yesterday this bra wasn’t designed for comfort but to emphasize my breasts and the sissy nature of the creature wearing it. It was lacy and had no lining so that it was constantly scratchy on my breasts and while it pushed my breasts up, it seemed to allow them to jiggle and bounce freely.
The brassiere was followed by a matching pair of thong panties. As with the bra, the material was unlined and scratchy on my locked up cock and the rear thong rode uncomfortably up the crack of my ass. My trainer, who I now knew to be Tina but whose name I was not permitted to use, told me “Sissy, you will always wear thongs. It makes it easy to spank you without having to pull down your panties and expose that ugly, useless appendage between your legs.”
Actually that wasn’t quite true. The tip of my cock extended past the brief triangle of lace and was clearly visible from behind. Beside that the lace was more or less see through so nothing was really hidden. I suppose the part about being able to spank me without removing them would prove to be true.
Having managed to dress in bra and panties with some shocks and demerits for being clumsy, we moved on to a lacy garter belt. I managed to put this on with no further corrections but was then admonished for not having run the garter straps inside the skimpy waist of the thong. This was, I was informed, so that I could ‘go potty’ by lowering the thong without having to fuss with the garter belt.
Of course the next logical step was stockings. She showed me how to roll them up and then insert a foot and roll them up my legs. I don’t know what denier they were but suspected that they chose a thin one that would ladder or run easily. Of course with my longer nails I ruined several pair and each pair cost another demerit.
I finally managed to get a pair of stockings up on both legs and fastened to the garter straps with no holes or runs, only to be told that the rear seams weren’t straight. Of course that was another demerit. At her instructions, I removed both stockings and started over again paying attention to the seams as I smoothed them up my hairless legs.
We did a few more minutes of standing, walking and sitting and then she drew the lesson to a close. I was a bit surprised because it wasn’t lunch time yet, but dutifully draped myself across her lap. I don’t know if the thong and stockings inspired her but the spanking seemed much more forceful than yesterday.
When it was over I was ‘sissy walked’ to a room with a salon chair. My hair was washed, trimmed and styled. I was given instructions in maintaining my hair.
When we were done the stylist reached under her dress and pulled off her panties. She sat in a chair and dropped a cushion between her legs. Dr. Hatfield appeared with her riding crop and handcuffs. Guessing what was coming I knelt on the cushion and brought my hands behind my back.
“Good sissy”, said the doctor. “Perhaps you are coming to enjoy servicing women with your mouth. It will probably be the only sexual activity you get.”
The session was very similar to last night with Tina except that this woman, whose name I never knew, put her feet on my thighs pinning me securely in place and instead of removing her skirt, she just draped it over my head. I couldn’t see much but with the assistance of Dr. Hatfield’s crop I did learn that this woman responded slightly differently than Tina.
It took a long time before I brought her off and from under the skirt I couldn’t really tell how strong her orgasm was. There was a copious outpouring of fluid when she came and my face was slick and shiny when we went to the lunch room.
I was a bit worried as we ate lunch as the punishment frame was still in the lunch room but it turned out to be for some other poor sissy. I was a bit ashamed of myself as I watched him caned. I felt as though I ought to be sorry for the other sissy but all I felt was relief that it wasn’t me. I was a bit concerned that I thought of him as ‘some other poor sissy’ suggesting I now thought of myself as a sissy.
In the afternoon I had a makeup class and was trained in both daytime and nighttime make up so that I could assist my Mistress/wife. I learned that as a sissy I would use very little makeup but would be expected to wear foundation powder, some slight eye liner and lipstick at all times.
Of course when they wiped it off and had me apply it I looked like a clown and accumulated demerits. After four or five applications I was getting marginally acceptable. My trainer made it clear that I was to be dressed and made up with my hair properly cared for when she arrived each morning.
Of course taking care of both hair and makeup required a mirror and I was surprised to see how much my face had changed. I wasn’t a raving beauty by any means but I did appear to be a modestly attractive woman.
At the end of the session they made a game of my spanking with me lying over the back of a chair and each woman spanking one buttock. The game was that they competed to see who could make their cheek the darkest shade. They though it very funny but their position standing on either side of me allowed a full swing of the arm and the competition aroused their competitive spirit. I was crying and blubbering long before they stopped.
When they did stop Dr. Hatfield appeared again. I was prepared to kneel but they made me lie back on my bed which, of course was very uncomfortable with my well paddled buttocks. The makeup woman had been wearing trousers which she shimmied out of along with her panties. Then she climbed on the bed and moved up to cover my mouth with her pussy.
Tina and Dr. Hatfield each strapped one of my wrists to the bedframe and the doctor told me, “A sissy must ignore his pain or discomfort to service women. In this position you will have little access to her inner thighs and will have to focus on her vulva and clitoris. You should still focus on what pleases the woman you are servicing and modify your actions to improve her pleasure.”
I did find it harder to sense what was pleasurable but Dr. Hatfield used her crop to point out what was happening. It took me perhaps 40 minutes to bring the woman off and I was exhausted and ready for the evening meal.
Instead of releasing me, however, when the woman finally climbed off my face Tina mounted me. She, however, sat facing my feet so that my nose was caught in the crack of her ass. The good doctor reminded me to ignore my discomfort and get busy. She also told me that this position was called ‘queening’.
In some ways it was easier as I remembered what Tina’s body enjoyed. At the same time my reach was limited and when Tina sat upright I found it difficult to breathe. From time to time she would lean forward allowing me to gulp air. It was a long session and when I was finally released my trainer asked, “Are you ready for dinner?”
“Yes ma’am.” I politely replied only to be jabbed with the cattle prod.
“Your lipstick is gone, your makeup is smeared and your hair is a disgrace. That’s three demerits you stupid sissy but it’s so late we will start with those tomorrow morning. Now fix your face and hair and be quick about it.”
Sissy training – the second week
I won’t bore you with a day by day recital of the training. Suffice it to say that over the rest of that week and the next week I learned to wear a travesty of a maid’s costume and shorty or ‘baby doll’ nightgowns. I gave many pedicures and manicures and graduated to giving foot and calf massages. I learned to dust, vacuum, mop and scrub floors and to thoroughly clean kitchens and bathrooms. I also learned to strip and make beds and to do laundry both by machine and, for delicate items, by hand. Ironing was an adventure until I got the knack of it.
Of course I made mistakes and was constantly punished for them, but at some time during the second week I realized that I was earning punishments for current lessons only and that the remedial drills went without a hitch. I was shocked to realize that walking, standing and sitting in ‘a proper sissy way’ had become second nature.
Over the course of those 14 days I performed cunnilingus over 35 times on 22 or 23 different women. As with my other sissy skills I had become fairly adept at sensing what pleased the woman I was servicing and placing emphasis on that to enhance her pleasure. Dr. Hatfield still supervised those training sessions but used her riding crop less and less which further evidenced my improved performance.
Between muscle memory and the training I was slowly being brainwashed into a sissy. In fact I wondered if I would ever be able to remember how to walk like a man. As this realization crept over me I cried. I had never cried as a man but, I told myself, it was OK as sissies cried easily.
During those two weeks I had avoided the cane by complying, to the best of my ability, with the instructions given me. That lasted until the end of the second week when my trainer told me to bend over a table and began to strap on a dildo. I was frightened and panicked. Realistically I knew I couldn’t escape anything they wanted to do to me but my fear overrode my reason and I tried to bolt from the room.
I was quickly subdued with the cattle prod. My trainer handcuffed me and tied my ankles to a table. Then she pushed me down on the table and ran a rope across my back just below my shoulders. When she tied the rope there was some slack but she inserted the cattle prod under the rope and twisted until I was firmly held against the table. To keep the rope tight she wedged the cattle prod against the underside of the table. With my hand cuffed behind me I could just touch the tops of my buttocks but was unable to reach lower.
As she tied me down, my trainer said, “That was so stupid sissy. You know sissies have to have their boy pussies pegged. We can’t return you to your Mistress/wife an anal virgin. I would have been gentle with you but rebellion after all the time I have spent with you is unforgivable. Now you will be caned for not obeying. In addition you will be pegged rather brutally and repetitively.”
I could tell from her tone that she was very angry and viewed my abortive rebellion as some sort of personal affront to her training ability. Leaving me tied down she then called someone and invited her to join us and bring a punishment cane and ‘the big strap on’.
My trainer didn’t wait for the others but squirted some sort of lubrication in the crack of my ass and then forced her strap on into my anus. She began to saw in and out forcefully. I have heard that some people enjoy anal sex but I found that I felt nothing but pain and humiliation. Apparently my trainer was getting some sort of vaginal massage as she slammed in and out of me because she eventually had an orgasm.
When the door opened I heard Dr. Hatfield’s voice asking, “Was there a problem with your sissy, Tina?”
My trainer replied, “Yes. The little sissy boy had been doing so well up until now. Then today he decided he was too macho to be pegged.”
“We can’t have that. Here’s the cane but after you correct him you will have to use the bigger dildo on him.”
“Yes…” Tina replied, “…and I’ve invited a couple of others to join me.”
“That’s a good idea.” Then Dr. Hatfield said, “I have another idea. It’s something that has worked well before with sissies who pretend they are still men. After you are done with him leave him on the table for the night. I’ll send Sally and her sissy down in the morning.”
I had no idea what she was talking about but my trainer seemed to know as she laughed and nodded in agreement. At that point the door opened and two women I had serviced orally, but whose names I didn’t know, came in. One of them was carrying a huge dildo. Dr. Hatfield left at that point.
One of the new women came around and saw my anus which must have still been stretched open. She turned to my trainer and asked, “Started without us?”
My trainer replied, “Yes, but he needs to be caned and then we can all enjoy him.”
Turning to me she asked, “Do you remember how to count and thank me for correcting you?”
“Yes.” I said.
Whoosh, the cane sliced across my rear and she asked, “Yes what?”
I gritted my teeth against the pain and replied “Yes ma’am.”
I don’t know what was more brutal, the 30 strokes with a cane or the forceful pegging or anal rape by each of the three women using the huge dildo. I wish I could say that I bore it stoically but it wouldn’t be true.
I manage to count and thank her for correcting me during the caning but totally lost it when they were ramming me with the huge dildo. Of course the pain in my ass became worse as they banged into my buttocks with each stroke. I was crying and blubbering before the first woman managed her orgasm. I was begging for mercy and shrieking by the time she was finished.
The second woman strapped on the dildo and said “He even screams like a little girl. How did he ever think he was a man?”
I don’t know if it was the pain I had received so far or if this woman managed to actually be even more brutal. I know that I couldn’t take any more and eventually I passed out only to be awakened by the smell of ammonia biting my nostrils. The second woman was still banging into me and my trainer was going to make certain that I didn’t miss a moment of it.
Eventually the second woman finished and my trainer strapped on the dildo and had another run at me. I can only vaguely remember her having an orgasm and then unstrapping the harness so the huge dildo was left within me. To ensure I didn’t force it out during the night, she wrapped the strap around my thighs. This time there was no one to wake me when I passed out.
The next morning
I woke slowly my body stiff and the smell of urine strong in the room. Apparently I had voided my bladder while unconscious. I was still tied to the table. I sensed rather than heard the door open and my trainer came into the room. She pulled the dildo with the still attached harness from my rear. It hurt but at the same time its removal was a relief.
The door opened again and I saw another woman on whom I had performed cunnilingus come in. She was holding a chain and following her was the feminized sissy waiter with the mini skirt and revealing top, carrying a tray. I couldn’t see what was on the chain but I did see that the chain ran under his mini skirt. She made a face and reached under the mini skirt unclipping the chain and said to her sissy, “This stinks. Mop up that urine and get something to mask the smell. Move now.”
The sissy gave a sort of curtsey and with a pronounced lisp said, “Yeth mith. Right away mith”.
He must have been familiar with the room because he went directly to the closet with a mop and bucket and air freshener. My trainer and the other woman, who I guessed must be Sally, chatted quietly as the sissy mopped the floor and then sprayed air freshener covering any residual smell with a heavy odder of pine.
My trainer recovered her cattle prod and untied the rope across my back. I groaned as I straightened up but swallowed it as I saw her sharp glance. She indicated I should kneel, which I did clumsily as my hands were still fastened behind me. The she said, “Lie down and roll so you are face down.”
I collapsed sideways and then straightened out and rolled face down. The sissy waitress placed two bowls on the floor in front of me. One contained some sort of porridge or perhaps oatmeal. The other contained water. I hadn’t had any dinner last night and even the oatmeal smelled good.
My trainer said, “Eat it all up sissy.”
Of course with my hand cuffed behind me all I could do was lower my face into the dish and lap it up like an animal. The same was true of the water but I was so hungry I didn’t hesitate. My trainer made certain I had eaten every drop before she and Sally grabbed my shoulders and lifted me to a kneeling position. I could feel chunks of oatmeal on my cheeks and chin.
Sally kicked my knees apart and then fastened a spreader bar between them. Behind me my trainer forced me to cross my ankles. She tied them in that position and then ran the rope through the chain between my handcuffs pulling so that I was leaning slightly backward.
When she was done she stood and nodded to Sally who said to her sissy, “Look at the mess on that face. Clean him up.”
He turned toward the supply closet but Sally intervened and said, “No! Use your tongue sissy.”
I suppose, given everything that had gone before and what was yet to come, having a sissy lick your face clean wasn’t much. Yet it seemed more humiliating and disgusting than anything I could imagine. The idea of this stranger’s tongue slurping over me was offensive. I imagined I could smell Sally’s pussy juices on his breath, though in truth that may have only been my imagination gone wild.
I leaned back as if to escape, which, of course, was nonsense as he grasped my ears to hold my head steady. I might still have tried to escape his licking but a jab with the cattle prod brought me to my senses and I stopped and allowed him to lick at me.
When he was done he stepped back and my trainer grabbed my jaw forcing my mouth open. Sally slipped a ring gag into my mouth and fastened the strap tightly behind my head. The straps pulled uncomfortably at the corners of my mouth holding the ring in place against the back of my teeth. I didn’t know what they were planning but I was certain I wouldn’t like it.
Sally turned to her sissy and asked, “How long has it been since you were allowed to cum, sissy?”
“Thirteen weeks, mith,” he replied, hopefully.
“Strip,” she ordered him.
He quickly disrobed and I saw that while he had breasts similar to mine, he still had his scrotum. It was swollen enough to suggest that he still had his testicles. His cock was curved down between his legs by a metal chastity belt.
“You’ve been a good, obedient sissy, not like this one.” Sally said. “I’m going to give you a treat.”
“Oh thank you mith” said the sissy.
She produced a key and unlocked the chastity device pulling off the curved tube but leaving the locking ring in place. The sissy immediately grew hard but looked to his owner for instructions. Sally laughed and said, ”What are you waiting for. Stick it in his mouth and fuck him.”
A pair of hands, evidently my trainer’s, clamped my head to hold it steady as the sissy pointed his cock at my open mouth and stepped forward. It happened so fast that I didn’t have time to cry out and now my mouth was more or less full of the sissy’s hard cock.
Sally took over holding my head by simply grabbing a handful of my hair. As my trainer’s hands fell away Sally began to pull my head forward and back. My trainer said’ “You don’t look so macho now you sissy cocksucker!”
As my head rocked back and forth his cock ran up and down my tongue. It didn’t take long before he began to ejaculate into my mouth. I tried to avoid swallowing but there was too much and I was beginning to choke.
When he finished his cock softened and he withdrew. My head was pulled back so that the cum wouldn’t drip out. The straps on the ring gag were undone and Sally twisted the gag pulling it out of my mouth. My trainer cupped my chin and held my mouth shut. With my mouth shut the cum reached the roof of my mouth and dripped back into my throat. I could do nothing but swallow.
My trainer laughed as she said “That’s it sissy. Swallow all that tasty cum like a good little sissy cocksucker.”
Sissy training – the third week
In the third week residual training continued as did cooking lessons but more personal services were taught. I learned how to dress and undress a woman. In addition to pedicures I practiced foot and calf massage. I also learned full body massage and application of lotions.
Despite the female hormones pumped into me, my cock painfully tried to get hard when I was rubbing lotion into a woman’s breasts. No, that’s not quite accurate. When my cock tried to get hard it was tugged by the ring and was very uncomfortable but it wasn’t painful when compared to the spankings, the electric shocks and the occasional caning.
Of course the women hadn’t been mutilated as I had so the massage often aroused them sexually. That invariably led to my servicing them orally. As I mentioned earlier, other than the strain on my tongue muscles, that didn’t bother me. In fact bring the women to arousal and orgasm gave me a sense of being in charge, at least for the moment. Short term thinking, I know but when you are essentially a slave you take pleasure where you can.
Then there was pegging. I still did not enjoy any part of it but after the punishment I had received I submitted to my trainer’s orders. With use of the cattle prod and spankings she got me to the point where I could be pegged without being restrained. She would have me bend over with my hands on my thighs just above the knees and hold that position until she brought herself off by slamming into my butt.
Changes in Training – week 4
In the fourth week we moved from strictly training to practical application. At my trainer’s instruction I gathered up my female clothes and moved from my room to a suite that she shared with a woman called Marcie.
The suite had a combined sitting/dining room and two bedrooms, each with its own bathroom. Off the dining room was a kitchen and beyond that were a laundry room and the maid’s (my) quarters.
My room had a bed on one wall and a dresser and make up table or vanity on the other wall. There was a short hanging rod also mounted on that wall. You really don’t need much hanging space when all you have are a couple of maid’s uniforms. The rear wall had a doorway (but no door) to a small bathroom with a shower, sink and toilet.
There were no windows in the kitchen or my quarters but both bedrooms and the living room had large windows. It was the first time I had seen anything outside of the building since I had arrived. Looking outside the scenery was filled with desert plants that suggested that I was somewhere in the Southwestern United States or perhaps in northern Mexico.
With the move, my routine changed. There were less formal lessons but I was to apply all of my prior lessons in maintaining the apartment and serving the two women. Marcie went to work in some function or another while my trainer generally lounged about the house supervising my efforts as she thought necessary. Of course any failures on my part brought punishment.
Generally my days were structured with tasks as follow. My alarm went off at 5am and I had 45 minutes to shower, use the toilet and dress including tending to my makeup and my hair. At 5:45 I woke Marcie by knocking on her door and then opening the curtains in her room. I then ran her bath and while she was bathing prepared her breakfast which was fairly light. She would have fresh squeezed orange juice, an egg white omelet, toast, coffee and some fresh fruit. This generally took until about 6:30 when I would wake Tina, my trainer. If Marcie finished breakfast before that time I cleaned the kitchen until 6:30.
After waking Tina I helped Marcie dress, bringing and helping her into her clothing. Then it was back to the kitchen to prepare and serve Tina’s breakfast which was generally larger than Marcie’s. Tina had either two fried eggs with bacon or sausage or a ham, mushroom and cheese omelet. She also had juice and toast but preferred English Breakfast Tea to coffee. With breakfast for the women finished I helped Tina dress and then returned to get some breakfast for myself.
After breakfast I stripped all three beds and remade them with fresh ironed linen. Tina, my trainer, would later inspect to see that the beds were properly wrinkle free. The used sheets together with the bathroom towels went into the washing machine along with the contents of both women’s clothes hamper. Of course their delicate underwear, along with mine, was set aside to be hand washed later. While the laundry was running I cleaned the kitchen until it was spotless.
Generally the white load would be completed while I was still in the kitchen and I loaded it into the dryer and started the colored load in the washer. Then it was off to scrub clean the bathrooms (all three, even if mine hadn’t really become dirty). I would occasionally be interrupted by Tina calling, “Sissy!” When I responded by quickly moving to whatever room she was in and curtseying, she would request (order me to fetch) whatever it was that she wished. Sometimes it was a glass of water, sometimes the morning newspaper.
Then I started ironing the sheets and blouses from the now dry white load while moving the colored clothes into the dryer. If I finished the ironing the whites before the colored load was dry, I would begin hand washing the lingerie. Once those were washed and hung to air dry, the colored load would be ready for ironing.
When I finished the scrubbing and the laundry and ironing it would be time to prepare my trainer’s lunch. Typically this was a light meal consisting of a freshly made salad served with a glass of white wine. I would also have a salad but without dressing and with water for a beverage. Of course I didn’t eat until my trainer had been served and completed her lunch. While I was lunching she would check the beds and bathroom as well as examining the ironed laundry. Of course any slight problems would result in a spanking with her hairbrush.
The afternoons were intended to be devoted to re-cleaning the kitchen, dusting and vacuuming in all rooms and then one big chore. The big chore was either polishing all the wood furniture or washing windows. Of course preparation of the evening meal would also take time.
I say intended because Tina, my trainer, would constantly interrupt my afternoons with her demands. It might be something as simple as repositioning her chaise lounge so that she got a more even tan or something as time consuming as spreading sun tan lotion on her lovely back and buns. One day she decided that her nail polish was the wrong color and required a complete pedicure and manicure. Of course, from time to time she would require me to tongue her to an orgasm. With all of these interruptions I rarely finished that day’s assigned big chore, which of course, called for punishment.
On the second day I failed to respond to her call because I couldn’t hear over the noise of the vacuum cleaner. Tina solved this problem by forcing a remote controlled vibrating dildo into my ass. The thin cord of the thong ensured that it wouldn’t fall out. I was told to insert it when I dressed in the morning and not to remove it until I changed into my nighty for sleeping. From then on when Tina wanted me she summoned me by turning on the vibrator. That meant I had to stop what I was doing and run to her to learn what she required of me.
When Marcie returned home I had to help her change clothes and generally give her a foot and calf massage. Some days she insisted on a f
