Mistress Psyche's Feminization Fantasies

 Home

Sissy Girl Stories

 Links 

 

Betty's Bed & Breakfast

by Priscilla Gay Bouffant

(An heiress acquires, " just the place," to showcase her hubby's many talents)

Chapter one: My Place in the Sun

As I minced as prettily as possible into the sitting room, I could not have been happier. Coming to grips with my inner femininity, and fully grasping the fact that I was born to serve females, as an effeminate Nancy Maid, had been difficult. That had been before, approximately two years ago when my "journey" had begun. Today, things were definitely different. I literally gloried in my newfound self. I was thrilled that my wife Paula, and her friends at our B&B, had taken the time to dominate, feminize, and mold me into the absolutely perfect picture of the submissive maid that I had become.

Following behind me, pushing the teacart was my newest trainee, Gigi, a lovely sissy novitiate. Newly married at 23, Gigi had been overwhelmed at her wife's insistence that she become a sissy cross dresser. A few months into her transformation, Lydia, Gigi's mistress had contacted the B&B and Gigi had reported for training. Now, two weeks later Gigi's wife Lydia and her lesbian lover Bev were watching with smiles as my assistant served his or her, first formal tea.

The B&B had once belonged to my wife Paula's aunt, Muriel. The name of Betty, and the homosexual female clients, had been inherited from the previous owner, a lesbian, and a good friend of Muriel's. Muriel, also a lesbian had enjoyed the clients. Some began to bring their sissy husbands, so they could be aided in their transformation, by the loving non-judgmental atmosphere of the remotely located B&B. It had worked well.

Once, during a visit, Paula had decided that at the first opportunity, she would attempt to begin to make me more feminine. To her, the opportunity came when her Aunt Muriel passed away, and left Paula the B&B in her will. Along with it came a considerable sum of cash. At the time I was out of work and Paula decided she would send me to the B&B to run it. I was concerned because the house was a full 3-hour drive from our home.

"Please Brett, don't be such a little fuss budget. My company has an office in the area. I could easily transfer there in a few months. We could rent out our home here or sell it," she said with a firmness that I had grown to recognize. "Pack enough clothes for the rest of the week. I'll be up this weekend. I've already spoken to Ms. Anna, the head housekeeper. She'll be happy to begin your training. She welcomes you as a full member of her staff," she said proudly, as if me, the new owner, was going to be a mere staff member!

As Gigi and I went about the room, I took in the warmth, and in a couple cases, apprehension of our guests. My wife, Paula, and Ms. Anna, the head of house keeping and a master chef, looked on proudly. We had four guest rooms, three occupied at the time. There was also my room, Ms. Anna's room, and Michelle and Paula's room.

Michelle, who also worked as a housekeeper and maid, was Paula's new girl, and also my immediate superior. Often, we had to put an extra single bed in most guest rooms. Many women brought girlfriends, and the sissy husband would have to occupy a separate single bed while the two women slept comfortably or made love in a nice, large, king bed.

This particular week, Gigi and his spouse, as well as two other couples were at the inn. The two other women, actually lovers, had brought their newly sissified husbands along. The two pansies set there watching us. They were dressed at the moment in unisex apparel, lightly made up and adequately perfumed. They knew that in Gigi and I they were seeing their very near future. They appeared to be nervous with it.

Myself, Gigi, Michelle and Ms. Anna had been required to move some furniture as the two new sissies had been made to sleep in the same room, but in separate single beds. Gigi and myself occupied my room, as it had two single beds also.

"We want them to become close girlfriends, but not lovers," one of the wives, Belinda, had remarked laughing. "As it is they both cry to each other like babies about the sissy things we make them do. We don't want them comforting each other sexually. June and I have them save their sexual frustrations for us," she laughed as most of the women present laughed also.

As Gigi and I served the tea and cakes to everyone we curtsied demurely and daintily. Once finished we left the serving cart off to the side. Any further serving would be done by "Prissy" and "Molly" the two sissy novices, present at their wife's insistence. Both pantywaists were expected to fully soak in the atmosphere of dominant females, and sissy spouses. Gigi and I left sashaying into the kitchen where Michelle was present.

"I'll let you two girly boys clean up the rest of the mess in here. I'll go do the laundry, but I'll guarantee that you two Nancy maids will be folding and ironing," she said as she tossed the apron down and left.

I knew she was presently unhappy and I was going to stay out of her way. As a true female, albeit a submissive one, she was still superior to me in the pecking order of the household.

Somehow she had displeased Paula, thus her relegation to "kitchen bitch" status. Had she been in Paula's good graces she would have been seated next to her in the sitting room, basking in the glow of being Paula's submissive lesbian femme. My attention turned to the messy kitchen and chatting with Gigi.

Having been instructed by Mistress to "feel her out" I began to converse with her. "Well Gigi, how are you enjoying your new femme persona?" I asked as I cleaned.

"I'm really not sure Miss Elizabeth. How long did it take you to adjust?" she asked smiling.

"Dear, please don't call me Miss Elizabeth. I'm simply Betty. No one in my recent past has ever called me Liz, Elizabeth, Lisbeth, or anything close. Just Betty," I laughed, my hand waving at her in a limp wrist fashion.

"It took me a while to adjust. Maybe three months. When I did, life took on a whole new perspective. Trust me, the rewards for being an obedient, efficient, sissy maid are tremendous," I said, looking her in the eye, hoping to pique her interest. Apparently I did make her curious.

"Rewards? Really? Such as?" she asked innocently enough. "By the way, I think that it's wonderful your mistress would name the B&B after you," she added. "Oh no. The B&B was named before I ever got here. Both mistress and Ms. Anna thought it would be cute to have someone named Betty working here. As for the rewards, well, here's a for instance. You did an excellent job today. It's quite possible your mistress may reward you at bedtime. Mine may reward me also. Sexually, we hope," I added, wondering what the evening would bring.

"If I continue to train you, where you perform well, we're both liable to be rewarded with a shopping trip, lunch with the ladies or maybe a trip to the beauty parlor for a perm or something really cool like that," I said, thrilled at the idea myself.

"Then you consider getting to do really girlish things to be a reward," she mused. "That's interesting. It may take some getting used to. Could you and I have some more girl talk like this later?" she asked. "I think it would be fun. Just you and I, maybe one or both of the new sissies" she added, putting her hand to her mouth, surprised that she would use the word sissy to refer to herself or anyone else for that matter.

"Don't worry about using the word sissy, especially around here. Your spouse will be using it to refer to you, quite often. Why don't we get together, say tonight, for a couple of hours after evening meal? We'll clean up first. Then go to the verandah outside our room. It's private. Maybe we'll even get to chat at bedtime if neither of us are needed by our mistresses," I said reluctantly.

"We'll have lots of help, serving and cleaning. Michelle and both of the new girls will be assisting us. The novice's serious training starts tonight. Trust me, I know. Michelle will be in Paula's "poodle house" for a couple of more days. I've seen this happen before," I confided.

"Okay, you're on" she said. I always liked telling someone, especially an apprehensive sissy, about my transformation. As a rule it was a comforting experience for both of us.

So once we had finished with supper, and relaxing on the verandah, I let Gigi in on the details of my transformation. Prior to our conversing, I suggested we do our hair first and shower.

First Gigi showered and shampooed and then I did. I had to smile when I came out of the bathroom, wearing my red kimono and white mules. Gigi was already at her vanity setting her hair. She had me check the rollers she had put in so far for tightness. She had learned fast! Improperly set hair could get us a couple of demerits and a minimum of five swats with a paddle.

Once our hair was rolled and we both put on hairnets and scarves, we went to the verandah to drink tea, do our nails and chat. As I had done many times, I began my story telling once again.

"It always seems, like only yesterday, that I knocked on the front door, here at the B&B. It was answered by a woman I have gotten to know and like very much, Ms. Anna Manly.

Chapter two: Maid Trainee, Betty Anne

 

 

Ms. Manly saw to it, that I knew from the start, who was in charge. "Oh yes. Your wife called to say you were coming. My name's Anna Manly. You must be Beth," she said.

"No ma'am. The name is Brett," I answered.

"Well come this way. "I'll show you to your quarters. At your wife's insistence you'll be rooming in the same section as the maids, Kathy and Sharon. She wants you to learn the business from the ground up and I intend to accommodate her," she said and then added, "Are those the only clothes you brought?" she asked looking at my small suitcase.

"Yes. My wife will be coming this weekend with more," I noted nonchalantly.

"Oh really? That's not what she told me an hour ago.” She's been called out of town on business. Indefinite stay. Not to worry. Once those get dirty, if we don't have time to launder them, the girls and I have things for you to wear. Unisex of course," she said as if this would be the natural course of events.

"Unisex, unless you prefer your things to be a little more femme. Oh what's this?" she exclaimed as she pulled a pair of Paula's stretch slacks and a blouse out of my suitcase. "So you did come prepared after all," she smiled.

No matter what I told her about the clothing not being mine, she wouldn't listen, and soon I was in her office with Kathy and Sharon, as she described the pecking order for my "trainee" period.

"Beth, I mean Brett, is to begin by performing the most menial tasks, just as if he were a maid in training. He shall wear an apron and some type of head covering. You girls will report his performance directly to me, or if she is present, his wife, Ms. Paula. This week, if he runs out of clothing, we may have to lend him appropriate apparel," she stated as I interrupted her, to the girl's giggles.

"Wait Ms. Anna. You said we'd launder my current clothing," I whined as if a spoiled child.

She frowned and stated slowly, as if warning me never to interrupt, "What I said, Miss Chatty Cathy, was we would launder them if we had time. For your information Miss bed and breakfast expert, we are in the middle of the week, after a busy weekend. It's nearly spring and we'll have guests everyday, very soon. Right now we are prepping for nearly a full house this weekend. We may not have time to do your laundry, Princess."

I was so humiliated, I looked away as the two maids tried to hold back their giggles.

Finally, Kathy could hold back no longer and laughingly said, to everyone's amusement, but mine, "Maybe we should call him Betty. After all, he's already acting as if he's in charge!"

The laughter nearly made me cry. Here I was, in the middle of nowhere, with three strangers, being laughed at for my inability to cope, get along, or do anything right. I felt so desperate. I couldn't help what I said next. "Please ladies, give me a chance. I'll do anything to help out and fit in. I really do want to be part of the team here." Then laughing to make light of the subject, "You know. One of the girls, so to speak."

They all stopped laughing and stared at me and then all three smiled. Sharon spoke first, "Very well spoken, Brett."

Ms. Anna added, "Yes. Precisely. Good my angel. We'll see just how much you want to cooperate in the next few days."

"Really Ms. Anna I mean it. I want to cooperate fully," I stated honestly.

Looking at me she grinned prettily, "Yes. I believe you do. Good. I'll take you at your word. All right girls, let's get to work."

With that, I found, that she was most serious about me wearing the most fluffy, ruffled aprons, and the brightest colored stretch turbans, or silk scarves on my head. "Menial tasks?" Absolutely! What could possibly be more menial then the scrubbing of bathroom tubs, tile, floors, sinks and toilets? If I found ladies stockings or panties in these same bathrooms, I was told to hand wash this lingerie in the sink!

The thing is, I did it. Without complaining at all. Of course I would complain as soon as I spoke to Paula. Unfortunately Ms. Anna wasn't sure where she had gone on her sudden business. She'd just gotten a new cell phone, so I hadn't that number either. I'd simply have to grin and bear it until I next spoke to her.

After an exhausting first day and a restless nights sleep, I was informed by Ms. Anna, that I would be spending the day with her in town. "We'll do some shopping for the house, and some other business. We'll also pick up a few things, for you and the other girls. In addition, you need your hair trimmed and styled to make you more presentable to our guests," she added, without asking me what I thought.

Town was only eight miles away, a short drive. We arrived at about nine thirty in the morning. We'd spend all day there. It would be one of the most significant days of my new life.

Our first stop was the bank. Ms. Anna had me follow her. I took in her firm, very full figure. She had a lovely head of perfectly coifed, blond hair done in a somewhat dated bouffant. She was however quite attractive. I stood quietly and meekly behind her as she discussed some things with the teller.

Just before leaving she introduced me to the girl as "the newest member of the housekeeping staff." The girl smiled and wiggled her fingers at me, in a sort of girlish greeting.

At the grocery, Ms. Anna did pretty much the same thing. I carried the packages of the purchases she had made, to the car. All non-perishables. Perishable items would be delivered.

Moving on, we went to the drugstore where she made a huge purchase of cosmetics, hair care items, hair care utensils, nail care products and perfume. At the counter, she gave me the money to pay for the order. The women ringing it up looked at me and then at Ms. Manly saying, "Well Anna. Are you and your new boy toy here planning on getting all dolled up?"

They both began to laugh at my embarrassment, as Ms. Anna said, "Not just yet Sybil. By the way, does Ellen still have that sale on culottes? We're thinking of buying a few pairs."

"Yes she does dear. However, if you're thinking of buying them for your new 'sweet thing' here I do hope you've shaved his legs. Ellen isn't to keen on "Hairy Mary's" trying on things that show off their legs," Sybil replied.

As shocked as I was I said nothing, as my new boss added, “Not much need to worry there Saw him leaving the shower last night. His leg hair is very sparse. Almost like a boy, just into puberty. Any shaving can be done at a later date. Come along Brett. We have a big day ahead of us," she said as I struggled to keep up.

She and Sybil exchanged good byes as we went out the door. I planned very soon to tell her how she would not be shaving my legs, nor was I her "boy toy". I didn't have time though, because soon I was in, Ellen's Unique Style Shop. I'd been in such shops with Paula, my wife and I didn't like them. Just as with Paula, I knew enough not to complain.

I saw right away that this shopping excursion was for me. I also had no allusions that my haircut would be done at a salon and not a barbershop. In fact I hadn't seen too many men at all in town. Mostly women, and the few men I had seen, had not acknowledged my waves to them.

After speaking to a sales girl, Ms. Anna turned to me saying, "Lets go to the Bramblewood Inn. Ellen's eating there. You can meet her. Then the three of us can return to her shop together. On the way to the inn you can put your cosmetic purchases in the car," she stated firmly.

The inn was the nicest restaurant in the town of Bramblewood, and bore the town's name. Ellen was at a table in the rear, had just ordered, and had a young, effeminate, college age boy, return to take our order. He referred to her as "Aunt Ellen."

Before sitting down Ms. Manly introduced me to Ellen. She was a pert blond, with short hair. I estimated her to be my wife's age. About 30, four years older then myself, possibly five years younger then Ms. Anna.

Ellen was extremely pleasant. In fact as lunch progressed, Ms. Anna went from being curt and bossy to me, to being very pleasant. Both she and Ellen spoke to me as if we had been lifelong friends. In fact they both took me into their confidence, as if I were nearly an equal. Equal, but younger and less experienced. It was much different then going somewhere with Paula, that was for sure.

My wife Paula treated me as if, she were an impatient husband, and I, the "air head" or featherbrained wife. It was quite humiliating, especially around her girlfriends. Once, when she and Michelle, (her secretary at the time) invited me for lunch, I had asked a dumb question about finances. This was prior to my realizing, that she and Michelle were lesbian lovers.

After the laughter had subsided, she had said to Michelle, "You can easily see why he can't hold down a real job. Can't you? If he wasn't so good at housekeeping and sex, I'm not sure I'd keep him around."

As embarrassing as that was, both she and Michelle might have had one drink too many, it being Friday afternoon. Michelle then asked, laughing, "Good at sex? Does he give good head?"

Both she and Paula really had a rousing laugh over that one, as Paula answered, "Very good head, as a matter of fact." They even ordered another round. I wasn't permitted to drink as I was chosen to drive them both home.

So, it was easy for me to feel quite taken by both Ellen and Anna. Here I was talking to two successful, self-assured, attractive women. Not only were they being nice to me, they would occasionally ask my opinion of something, albeit something feminine. Occasionally they would even touch or pat my hand, and once Anna even brushed some stray hairs from my face and referred to me as "precious".

We left the restaurant with me feeling lightheaded. Much to my surprise, Ms. Anna took my hand and squeezed it, smiling at me as she did.

It took very little prompting on their part, to get me to use the bath and shower in Ellen's office to shave my legs, chest and arms, so I'd "look nice" in my new outfits. Even so, I still felt self-conscious modeling the outfits on a pedestal just outside the dressing room. I would be made to turn one way, then another, as Ellen and Anna would discuss my appearance.

Occasionally other ladies shopping would stop to view me and give their opinion. During this time I saw four people enter, that for all appearances would be taken for two women of the same age, and a teenage girl and boy.

One of the women definitely was in charge, as the other seemed to defer to her. The teenage girl seemed older then the boy, and would occasionally chastise him verbally. Six months later I would meet this foursome, when Paula and myself would attend a fashion show at her ladies club in Bramblewood.

At that time, the boy would be attired as a girl. He would also be one of the lovely models. I would find that the older sister was indeed a female. She would be with her boyfriend "Tammy." The woman, who had seemed to be in charge, was the mother of the two children. She was also the head of the household. The meek submissive female, I would learn, was actually the transformed spouse of the dominant lady. He was being made to shop, dressed as a woman, and watch his son be sissified.

I left the shop dressed in a pair of lavender stretch slacks, a white fluffy sweater top, knee high support hose and cordovan penny loafers. In this apparel I walked tentatively to the hairdressers, a nice beauty parlor called, Salon Mary Chanel.

Marie, the owner, had purchased it from the original proprietor, and kept the same name. Just as Ellen and Anna, she made me very comfortable, even having her husband Gary serve me a cup of coffee in her office. After she "shooed" him off, she, Anna and I chatted.

By this time I was feeling so open and accepted that during the conversation I shared that I had not felt this welcome in a long time. As they listened silently I told them how I felt mistreated by Paula. I got so carried away with my emotions that I started to sob. Ms. Anna held me and comforted me, as Ms. Marie also commiserated with me.

"There, there now precious. What you need is a nice pampering here at the salon, after you've had a good cry," Marie said.

"That's right angel. A good cry, a pampering, supper, a nice hot bath and curl up with a good book. If Paula calls, maybe a chat with her might help. Actually, once she sees you take to doing a good job at the inn, and adjusting well, I'm sure she'll see you in a whole different light," Ms. Anna said proudly.

"Do you think so?" I asked, peeking through my tears, as both ladies nodded and smiled and escorted me into the main portion of the salon.

The cape they put on me was more of a kimono, pink in color, with a huge sash bow that tied in the back. As Marie shampooed my hair we chatted about the furnishings at the inn, and how I might want to decorate.

She also gave me a Luster Cream condition and a Suave cream rinse, before seating me in front of a mirror and beginning my cut. She decided on a "Dutch" bob, with bangs straight across at the top of my eyebrows, the hair cut even to my chin, all the way around. In back she trimmed it to a tapered wedge, slightly shorter then the rest of the hair.

She then took me back to the shampoo sink and asked Gary to bring her a "50/50 mixture of 8a and 8b." then she added, "I'll shampoo it in. Save me the rest of the 8a for a paint on highlighting," she said as if talking to an employee.

"What about the rest of the 8b, dearest?" Gary asked sweetly.

"You can use it to touch your roots up sweetness," Marie added, as if she were talking to a child.

The shampoo in coloring left me with a really light blond shade. Once Marie put the plastic cap over me and began pulling my hair through, with what looked like a knitting needle, I thought I would never want to return to a beauty parlor again.

After the hair was pulled through, she painted each section and then wrapped them with foil, putting me under a really hot dryer. It wasn't lost on me that she gave me a pictorial magazine to read called, Dutch Bob Versatility. "Here's all the different styles you can achieve with your cut Brett," she smiled.

While I literally baked under the dryer, I noted there were plenty of up sweeps I could try and thought of which one I might wear the first time I would see Paula at the inn. I caught myself, and wondered where that idea had come from.

Marie wasted no tome with my make over, getting me back to the sink for a rinse and into the vanity chair again. She tilted the chair back and put something warm and gooey on my eyebrows. Ouch! I had been zip waxed without knowing it. Then she took some hair color on a q-tip, and tinted my lashes and brows.

During what I thought would be the last procedure, she dipped her fingers into a jar of blue styling jell, and massaged my scalp. Then she rolled me up onto some hot rollers, letting this set for ten minutes. Lastly, or so I thought, she used a blow dryer and comb to fashion a hybrid, modified, bouffant/bob, which would have made any fashion model look quite chic.

As nervous as I was, as she rotated my chair, holding a mirror so I could see myself at all angles, I actually liked it! I smiled and told her so. The color was a lovely, light blond frost with champagne blond highlights!

Setting next to me and holding my hand Marie said, "You're among friends baby. Would we like to try some make up? You'll be wearing it sooner or later. It's what your wife wants. Wouldn't you like to leave here with at least some lipstick and blush on?" she asked condescendingly.

When I told her I was scared, unsure, and didn't know what to do, she left and returned with Ms. Anna. Her hair was now more sleek and modern looking, a nice pageboy. She told me her stylist had talked her into "doing something different."

Sitting next to me she said, "What's wrong with my Betty? Why don't you tell Aunt Anna what's bothering her new girl?"

I told her of all my misgivings and sobbed a little. She listened and then frowned slightly. I had become such a puss, that her frown scared me a little.

"Didn't you just tell us how good you felt today, finally being accepted by females? Why then, when you're so near complete fulfillment do you want to balk? I even kept some nice shoes with me from the clothes we put in the car. I have them right here. A little blusher, some lip color, a touch of eye make up, and some pretty shoes? You'd be all set," she said firmly and without anger.

"What about my flat chest?" Won't people know I'm a male with cosmetics on?" I asked, surprised I would even raise the question.

"You silly goose!" she said laughing. "You need not worry about that. You have on a puffy sweater, for one. We can't really put you in a padded bra now. Taking your pullover sweater off and putting it back on would ruin that gorgeous hairdo. Trust me. No one here in this town will say a thing unpleasant to you on your way to the car," she said adamantly.

I nodded my consent and Marie came over to me and began to show me how to apply and blend foundation, blusher and powder. Once satisfied that it looked right, she applied my eye make up. Believing that applying lipstick would be a real "treat" for me, she had me apply my own lip liner and then fill it in with a glossy, magenta lipstick.

Perfumed, doused with hair spray, and shod in inch and a half tapered heel pumps, I was led by the hand to the front of the salon where Ms. Anna paid. At the counter she purchased a red, clip on bow, about 4 inches long and an inch wide. She pinned it to the side of my hair. Promising to return me in a few weeks for a permanent, Ms. Anna led me to the car, even holding the door and belting me into the passenger seat.

I was in a dream world, all the way back to the inn, where the happy duo of Kathy and Sharon met us. "Goodness Brett, is that you? You look gorgeous!" said Sharon.

Before I could answer Ms. Anna said, "Yes indeed it's whom you think it is, but the name is now Betty Ann. Let's get the packages girls. Sharon, you take everyone's cosmetics to their room. I purchased everyone's favorite brand. The Cover Girl I got for Ms. Paula. The Tres Fabu, belongs to Betty," she said smiling at me.

Anna and Kathy carried the groceries and I had my hands full with all my new clothing. Once in my room I began to put my things away and Sharon came in and set up my vanity with make up, perfume and hair care products before putting everything else away either in the bathroom or closet.

That evening I watched television wearing a nightgown, high-heeled slippers and my hair protected by a net and bouffant bonnet. Friday I wore my first maid trainee uniform, and padded bra, with a special figure training corset.

I prepared to receive my first guests, two lesbian couples. I still wondered when Paula would call, or contact me in person, but the next few days would be so eventful, I could hardly think of my wife.

Chapter three: Initiation

 

 

The two pairs of guests arrived within a half hour of each other around two, on Friday afternoon. I'd spent the night in hair net and bouffant bonnet, my hair being heavily doused with perfume, spray net, and lacquer prior to bedtime. The constant and heavy perfuming would serve to remind me, that indeed, I was expected to be feminine at all times.

In the morning, as I would do throughout the next month, I sat in the anteroom outside the maids quarters, waiting for any one of my three superiors to show. I was still netted and bonneted, dressed in my feminine sleepwear, of baby doll nightgown and fluffy pink robe.

I was made to face a mirror to really "soak up" how feminine I looked. Once Kathy came for me I was taken to my room, to be dressed. This particular morning, I would wear a waist cinch, panties, pantyhose, plain dark knee length skirt, white cotton blouse, and a lacy maids doily.

My make up was done tastefully and subtlety and perfume sprayed on slightly. The cosmetics were all light pastels. The company Tres Fabu, catered to transformed males, and was located in Southern California.

Once the guests arrived we showed them to their rooms, and found out what they would like in the morning for breakfast. No one seemed to care when I was introduced as "Betty, a sissy novice."

That evening I received a call from Paula and when I filled her in on the happenings she simply told me, "You are to obey your superiors Betty. This is what I want for us. I'm selling the home, and Michelle is selling her condo. Within a couple of weeks, maybe less we'll be at the inn with you."

She went on to tell me that Michelle would be quitting her job and helping out at the inn. Paula would be transferring to an office her company had in the area. They already had a secretary lined up for her.

"I've already met my new secretary. He's a very cute young boy of about 22. He must be very special. He's a grad of Elite Secretarial Academy. Elite takes in about 5% new male students for each class. The greater bulk of their student population is female. Whenever you meet him, I want you to be very polite to Victor. No jealousy. Do you understand?" she asked, as I tearfully said that I did.

We ended the phone call with me wondering if I'd been such a failure as a husband that Paula now wanted me as a wife.

At the inn, whenever we had guests, we would prepare and serve breakfast to them. Once they left we would first clean their rooms and make their beds. Then we would clean the rest of the house. We made lunch and dinner for ourselves only, but made baked goods and snacks for the guests. However, when sissy novices were being trained, guests were invited to all three meals.

The first weekend went smoothly. It wouldn't be until a short time after Paula moved in, that I would see my first sissy spouse at the inn. It was Monday after our guests had departed that my initiation took place at the B&B.

After cleaning up the supper dishes I had showered, shampooed and conditioned my hair and begun to roll it up. Kathy came in and offered to set my hair. While we chatted Sharon came in to talk also. I was really feeling relaxed and once Kathy finished setting my hair she wrapped it tightly in a scarf.

She then took a second scarf and before I realized it she used it to blindfold me! Sharon then tied my hands behind my back with another scarf and I was led to Ms. Anna's bedroom, on a leash attached to a velvet collar.

"Don't worry Betty, all our maids get this same initiation. After tonight you'll be a full fledged sissy maid," Sharon told me. I was only wearing a panty brief, bra and three inch heeled slippers. I'd been using slippers to train myself to walk in higher heels each day.

Ms. Anna had the girls tie me spread-eagled, face down on the bed, my head facing the foot of the bed. I realized my plight when Kathy removed the blindfold. "We are going to raise your buttocks my sweet, and warm it up a bit," Ms. Anna pronounced.

She continued, "This is just so you'll never forget your place in the household. After your paddling, we'll have a few treats for everyone, if not for you darling," My panties were then pulled to my knees and my butt was baby oiled inside and out.

The swatting of my rear began with Kathy getting in five good swats. By the third smack I was screeching, begging for mercy. "Oh, please ladies, don't spank me! Haven't I been a good girl so far?"

"Indeed you have Betty, and we want to insure you remain a little goody two shoes in the future," stated Ms. Anna. " By spanking you now, you'll know exactly what awaits you if you ever misbehave towards anyone here at the house. We want you to know we mean business. Sharon, I believe it's your turn. Give her a half dozen or so swats with her paddle," Ms. Anna added.

Indeed, when she said it was my paddle, she meant it. This instrument of discipline had been designed for me, by a Domme in Chicago, who made special birch paddles, with small, drilled holes. Then the paddles were hand painted with little flowers by her sissy husband and monogrammed with a cute phrase, which included the sissy's first name. Mine was called "Betty's Baby."

The paddle's handle was big enough to grip with both hands and had a dual-purpose piece of rawhide attached to the handle's end. This rawhide made the grip better and also facilitated hanging the device up. Mine hangs ominously beside my vanity mirror on a hook, to this day.

As Sharon reached seven stokes my screeching became sobs. I was then instructed from now on to count each stroke out loud and punctuate my count with the words, "Thank you so very much mistress."

At this time Ms. Anna took over and gave me a half dozen more swats before stopping the festivities to have both the girls soothe my butt with cold cream and condition my genitals also. Their ministrations at first caused me discomfort but soon I couldn't help but become sexually aroused.

Through my crying and sobs I began to gasp as my penis began to swell. A lubricated finger entered my rectum and my sphincter muscle began to expand and contract. "Relax sissy, relax," Sharon whispered to me, "What we want you to do, is enjoy this," she added.

What I soon "enjoyed" was a small vibrator, about the size of my own penis, buzzing in and out of my rectum, followed by someone entering me with a faux penis, somewhat larger. From the weight I knew it had to be Ms. Anna, who soon confirmed herself as my "lover", as she whispered, "Now you are going to feel like a real girl honey."

Tears of both joy and pain came to my eyes but I soon realized she was being extremely gentle with both her entry into me and with the speed and force of her movements. I was as grateful to her for her gentleness, as any virgin would be, towards her first lover. She really did make my first time really special.

My thrusts soon matched hers and I moaned and sighed in a really feminine way. Ms. Anna said to Kathy, "Milk the little swish. She's really begun to enjoy it."

I was then treated to being brought really close to orgasm before the ladies stopped and changed positions. All three took turns milking me and pumping my rectum. I've come to the full realization today, that every humiliation, disciplinary measure, and overly feminine experience I've had, were necessary to complete my transformation into the compliant, well adjusted, Nancy maid I am today.

Between the milking and pumping I finally came. As I did so, Sharon, who was now wearing the strap on, increased the pressure on my sphincter. Ms. Anna squeezed, ever so slightly, the base of my penis and released it, massaging the very tip. The feeling was incredible! The surge, the rush of adrenaline, the sissy cream escaping from my engorged sissy clitoris as everything expanded to the maximum!

I thought my head and the head of my penis had blown off! My scream would have drowned out a fire station siren. I collapsed into tears of joy and surrender. I had found out who I really was. My sleep that night, in the arms of my "Nanny", Ms. Anna was ever so peaceful.

Chapter four: The "Nancy" of the House

 

 

Gigi stared at me incredulously and I had barely scratched the surface of the story. Just then there was a knock at the glass door leading to the verandah. My darling wife Paula entered smiling. Gigi and I stood up, curtsied, and said simultaneously, "Good evening Miss Paula."

"Good evening girls. Don't the both of you look sweet with your hair up, nails done and having tea? I just wanted to say that in view of your current performance, myself and the other "powers that be" have decided that you should take tomorrow off. Do anything you wish. You can shop, do lunch, relax here, you name it. Continue as you are doing and we plan to treat you both to something very special." Paula said this as if she were speaking to two teenage girls. Gigi and I took it as if we were a couple of 16 year olds!

"The two new sissies plus Michelle can handle the chores. Now why don't you be smart little sissies and get some rest?" she said with a mock firmness.

We clapped our hands together and smiled at each other and thanked Paula profusely as she left the room. "Gigi why don't we get some sleep now and tomorrow we can spend the day relaxing at the pool in the backyard?" I asked, trying to be as adventurous as a sissy possibly can.

Gigi agreed and we went off to our little beds and were quickly asleep. We awoke the next morning, had a light breakfast, did our hair and make up, and put on our ladies swimsuits and lounging robes. While we relaxed and tanned at the pool, I continued my story.

"I can recall that in the next few days I was really accelerated in becoming more feminine"

Mornings, I now dressed before going to the waiting area. From here on I was under Ms. Anna's direct supervision. The very first day after my initiation, Marie from the salon came by and pierced my ears for two sets of earrings. I was also told that unless I was doing yard work or really heavy housework I was to wear four-inch high heels.

I would literally scurry about the house taking those precise, practiced dainty steps that I have now become accustomed to. Ms. Anna wanted my hair to be either in an up sweep or a slight bouffant, always with some sort of decoration. "A bow, barrette, clip, even a comb will be fine Betty. I want you to stand out," she said firmly.

She wanted me to stand out so much that I was introduced to people as "The House Nancy." At times I would introduce myself in the same way. In preparation for my wife's arrival I was taken to the salon and given a permanent wave by Marie.

It was on this particular day that I finally met "Yvonne", Marie's sissy husband Gary. During my first appointment, I'd met him as a he. As soon as someone like myself was finally "out", Yvonne would be introduced so both sissies could commiserate and identify with one another.

"She" was dressed in a very traditional, pink, stylist's smock with a short skirt and "sensible" two-inch heeled pumps. I really liked her jade earrings and the perfume she wore was super.

Yvonne did my shampoo before my hair was given a layered fashion cut by Marie. "We really do want you to look tres chic for Paula. We're going to put a pair of hoops in one set of your new pierced holes and something colorful in the other set," Marie stated.

She sectioned my hair and then rolled it really tightly on the colorful wave rods. Actually, I found out I wasn't getting a permanent wave but something less harsh called a body perm. It still really did smell when she put on the solution.

Under the dryer she gave me a sissy fashion magazine to read called Prissy and Proud. It really made me feel better about myself and my situation. I now knew there were other sissies and many were really well adjusted to the lifestyle.

I got to pick out my finished style from a book. My hair had grown and was easy to wear in an up sweep. The curls the body perm gave me looked really nice on top of my head. I'd wear the same style the day I would see Paula, for the first time in six weeks.

I was really nervous the day she arrived. I felt a little upset that she and Michelle arrived within a few minutes of each other. I really had wanted some time with Paula alone. I answered the door as any maid would. I was wearing a long sleeved, just below the knee, black dress, with white lace trim at the cuffs and collar. My apron was also white and ruffled, and came to the hem of my dress.

My stockings were sheer hose. My hair up, make up tasteful but obvious, one set of small hoops in my ears, I was the picture of demure virginity. The only concessions to being dressy were the 5-inch, open toed pumps I wore and the "Proper Nancy" cap atop my upswept locks. Dangling from the hat, were two feet of ribbon streamers down my back. Of course I had been bagged up at the genitals and corseted to the max. I curtsied and said "Hello Mistress Paula and Miss Michelle. I'm thrilled to see you both."

"We are also Betty," my dear wife said as I took their coats and handbags and showed them in. Michelle laughed of course. Once they were seated I took their drink order and let Ms. Anna know they had arrived. She also gave me her choice of drink and went in to greet them. When I returned they discussed my progress as I served them. They spoke of me as if I were not there.

Finally as I stood by demurely, hands folded and head bowed, Paula spoke, "Ms. Anna has told us of your fantastic progress. I can also see it from your lovely appearance. She feels one of your trainers, either Kathy or Sharon could be paid and return to their place of business. I'm very proud of you Betty." With this my wife stood up and hugged me, also giving me a kiss, full on the mouth! I was ecstatic!

Michelle chimed in sarcastically, "Yes, Paula must really be proud of you Betty. All any woman wants in a husband, is a toilet cleaning, slipper sucking, panty washing, Nancy boy." That really almost made me cry. Luckily Paula turned and put her fingers to her lips to silence Michelle. She also frowned to show her displeasure. Michelle had a look of surprise on her face and said no more.

By now I had been informed, about two weeks before, that both Sharon and Kathy worked for professional Dommes and had been hired to help Ms. Anna train me. One would stay around until Michelle got practiced in housekeeping. Soon enough we would also have visiting sissy spouses to help us with the household duties.

"Who have you become best girlfriends with Betty? Don't be shy. Who do you feel closest to? Is it Kathy or Sharon? Don't worry. No one will be upset," she said waiting for my answer.

Though it was difficult for me to decide I finally said, "I adore them both. However Sharon and I are closer to the same size so we exchange clothes more often. I guess she would be my best girlfriend." This brought Michelle to the point of a belly laugh and she excused herself, asking where her room was.

"You and Paula will be staying in the room with the oriental furnishings. I'll show you. Betty, I think you should get their bags," Ms. Anna said. Paula came to the car with me and held my hand the entire way. She deemed some of the bags too heavy for me and carried those. Once we had all the bags to the room, Paula seated herself, pointing towards the center of the room.

Michelle was already running her bath. I stood meekly in the center of their bedroom, as Paula began to lecture me. "Here are how things are, and also how things will be Betty. Paula and I are lovers. She is my sub, but towards you she is a superior. You will wait on me first and foremost and on her if I assign you to it. I also intend to have a relationship with Victor, my new secretary. >From time to time he will stay here. You will refer to him as sir or Mr. Victor. You will also curtsey to him. You might also be expected to clean his residence or serve in his household should he throw parties. Have I made myself clear darling?"

Meekly, I curtsied and said, "Yes Mistress Paula."

She continued, "In addition, you will occasionally will be granted bedroom privileges. You may pleasure me, Michelle or any female in this house who cares to have you. Guests included. However, no matter how female you may become, in body or mind, you will never be allowed to pleasure a male or a sissy. Do that and I'll banish you from my life forever," she said adamantly.

Again I curtseyed and agreed to her terms. Actually it was a relief to know she didn't expect me to have sex with anyone but females. She smiled and came towards me saying, "Go to your room and get out of your Fifi outfit. Get into some sexy sleepwear. I'll come for you when Michelle and I are ready for you."

I did just as she told me. It turned into an interesting afternoon. Though I spent much of the time watching I was occasionally "used" for my newfound talents.

Chapter five: The Head Sissy

 

 

Kathy bade us all goodbye a few days after Paula had settled in. She admonished me playfully, "Now you be a good little sissy, Betty Anne. If I hear you've been naughty I'll get on a plane just to come here and spank you." Sharon would stay another couple of weeks to get Michelle broken in. I now prepared for my first pair of lady guests who would be bringing sissy husbands along.

They arrived two days after Kathy had flown to Washington, DC, where she worked for a lady named Mistress Judy. The two couples arrived in a Dodge Caravan. As the husbands got out of the middle seat of the van, it was obvious that both of them were real sissies.

They wore the same style of short shorts, or in this case hot pants. Their legs were slim, tanned and shaved. One had a white tube top and the other a cream colored silk blouse. Their blouses matched in color, the three-inch, strap sandals they had on their feet. Chris, the one wearing the silk blouse, had pink satin hot pants, while Carl had on red velvet shorts.

Their nail polish was silver, and they had on waxy white lip-gloss. Heavily perfumed, "Christine" had shoulder length hair done in a French braid. "Caroline" was obviously the recent victim of a roller set, and her business style bouffant was the giveaway. They each grabbed a door as they helped their wives out of the van. As the two dominated sissies struggled with the luggage I walked out to the porch to greet the wives.

As I still do today, I curtsied and said, "Hello ladies and welcome to Betty's B&B. I'm Betty Anne, your Nancy maid for the weekend. Should I help your sissies with the luggage or shall I show you inside first?"

"No, the girls can handle the luggage. We'd like to be shown inside Betty," one of the women said, adding, "Well Gwen, this should be interesting for the girls. Can you believe the on site Nancy they have? It will be an interesting three weeks for Caroline and Christine," she laughed as we went inside.

In most cases the lady guests came for 3 days to a week. They would then leave their sissies for an average stay of three weeks. Actually Ms. Anna had trainee packages from one to six weeks long. Then the women returned for another short stay, picking their newly trained maids up, to take them home.

Gwen and her lover, Sandra, had planned on a weekend vacation and leaving their "girls" for three weeks. Then they would return to vacation for another week and pick up pointers from Ms. Anna. Unfortunately, mid way through this training period, Sharon would be flying home to Chicago, where she worked for Madame Jessica, the Domme who had custom made my paddle. I would really miss her.

Ms. Anna has a method she uses to mold her sissy trainees, that begins the moment the sissies are separated from their mistresses. I saw it in action for the first time. It actually works best when sissies are in pairs, but if the occasion arises, where she's training a lone sissy, she will use me as the second girl.

As soon as Gwen and Sandra left, Monday at noon, the method was put into action. I've never failed to see it work. The first thing she does, is marches the sissies to the room their mistresses used and has them clean it, concentrating on the bathroom especially the toilet. They then clean every other room and toilet in the house, hand scrubbing all stray lingerie.

Once they are exhausted she has them eat, bathe and finally she puts them in baby dresses for "sleepy bye." They are marched down stairs with their dollies, to have their hair set in rollers, usually by Ms. Anna and someone else. Sometimes I help with the hair setting, sometimes Michelle. Even Paula lends a hand. Once their hair is set they are given, over the knee spankings, milked and sent to bed.

The next evening they are treated like "big girls" and given the initiation I received on the bed in Ms. Anna's room. After that, they are encouraged to be "sisters" to one another, doing each other's hair and nails, complimenting each other on their appearance, helping one another with the endless chores. When their mistresses return, they are pleasantly stunned to find such simpering, compliant sissies, mincing about. The only thoughts, they are left with, are to please their mistress and to look pretty and feminine.

"Wow that's quite a story Betty. I was wondering. I've had my initiation. Will the two new girls be having theirs soon? Gigi asked.

"Of course. Two nights after their wives leave," I answered, adding, "We may be asleep by then, but don't let any noise disturb you. Though Michelle can be a tad rough, Paula and Anna are absolute angels with the virgin sissies," I replied knowingly.

Indeed I never have let the goings on at the B&B or in Bramblewood bother me at all. After all I'm sort of a celebrity hereabouts. I'm the owner of Betty's B&B.

Epilogue

 

 

It's a quiet day, shortly after the New Year holiday. I'm serving tea to Ms. Anna, Michelle, Paula and Mr. Victor. We're not expecting any guests for a couple of weeks. I mince and sashay about the room, curtsying to everyone as I wait on them. The chatter is polite and friendly.

Mr. Victor has spent the evening. He does occasionally. Though, Paula prefers staying at his place. Less complications with Michelle, and Ms. Anna doesn't recommend having a sissy trainee around a real man, especially, early in their transformation. Paula agrees with her on that one. Mr. Victor has always been pleasant towards me, although our first few meetings were a little strained. Even though Paula had prepared him, he still looked at me strangely for some time.

I can't really blame him. It's a normal reaction for any real man, to be awestruck upon their first meeting of a real sissy. Actually, I've either heard of, or noted, a few different reactions. I've been told some men are repulsed by the sight of a sissy. Possibly this is normal, but I wonder if it isn't homophobic.

Others, I'm told, are amused, especially if the sissy is the hubby of the man's girlfriend. No competition there. One reaction I've experienced on a few occasions are the pleasant smiles and occasional flirtations of male guests I'm serving. Like any good mistress, Paula has taught me how to discourage any sexual advances.

Finally, there is the uneasiness Victor showed when we met. I believe he held Paula in awe for being dominant enough to sissify me. I once recall one of her college girlfriends commenting, "Paula, you were always such an ardent feminist. Only you could get the guy you married to dress like a maid and scrub your toilets."

Victor also wondered what kind of wimp I must be to permit my own transformation. I'm not sure myself. In fact, I'm unsure of Victor now.

On the particular afternoon I'm speaking of, I had went to the kitchen to wash some cups, and returned to a slightly strained atmosphere. Michelle was leaving the room sobbing and Ms. Anna was following after her. Apparently, Victor had been flirting a bit much with Michelle and Michelle had been returning the attention. I tried leaving, but Paula called to me and told me to stand in the corner.

"I'll need you presently, Elizabeth Anne," she said very firmly. Elizabeth Anne! She was seriously put off!

"Victor, I want you to understand that you are mine! If you'd like to keep it that way, then you will realize that Michelle is mine also! In addition you should realize that, never the two shall meet! If that's not clear dear, you should get a new job, find a new condo, as I won't be paying half your rent, and find a new lover! Possibly Michelle would be interested," she said as she paused for what would be a very meek reaction from Victor.

All I heard him say was, "Yes darling, I'll never so much as look at another woman as long as I live."

I honestly don't know if she expected this response, but what she did next was a stroke of absolute genius.

"Betty, come here. I want you to model for us, just parade around the room. Mince, prance, preen, do whatever comes to mind. I want you to glory in your absolute, ultra femininity. Don't stop until I say so," she said with hardly any emotion in her voice.

I need not tell you I did exactly as I was told. After close to five minutes she had me stop and said, "Now come over here and curtsey. Then pose like a demure parlor maid."

I did so, posing in the meekest, most pansy like manner possible.

"See this Victor? See little Miss Thing here? If all else fails, and you really displease me, you can wind up like this. Would you like that Victor?" she asked with a facetious tone.

Victor turned white as a sheet, looked down at his feet and said, meek as a mouse, "No dear. Please don't? Anything but that."

As far as I know he's been as meek as a lamb since that day. Every once in a while, when no one is looking I wink at him. He's never mentioned it as far as I know. Two weeks ago Paula left the house with him on a shopping trip to Elaine's. I haven't seen them since. I did mention it was two weeks ago, didn't I? I wonder what she's going to call him? Vicky?

End

 Home

Sissy Girl Stories

 Links