New! Classy Lassies

Priscilla Gay Bouffant

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A woman's best friend from college, performs a couple's makeover

Chapter one: Teased and Sissified

I really never wanted to help out Lisa. All I remembered about her was her ardent feminism. She and my wife Sandra had belonged to every militant feminist group there was at college.

I still blamed her for the way Sandra looked today. Sandy could be so pretty if she wanted to be. Instead she wore her reddish brown hair in a bun or ponytail. Blazers and slacks. The only shoes she ever wore with heels, were her zip up, Cuban style ankle boots. Rarely if ever did she wear make up.

Lisa was not only her best friend, she was her mentor. Two years older and one year ahead of her at school. She didn't get her MBA like Sandra though. Instead she got married during her year of graduate studies and moved to the west coast.

So when Sandra told me that Lisa has just went through a divorce, sold her house and wanted to get back in the work force I knew what was coming next. She added that she wanted to return east and go back to school.

"I told her she could stay with us as long as she needed to," Sandra said. She'll pay board until she gets part time work and a place to stay, Bill. She got a good divorce settlement. She won't be with us that long. What do you think honey?" Sandra asked, her voice with an unusual feminine lilt.

"Well, how long, is not too long?" I came back.

"Really Bill," she snapped," Getting right back into character. "You don't ask someone who needs a place to stay, when their leaving."

"Okay, you handle it. Remember, I don't think she ever cared for me." I remarked.

"You've both changed. You're not the biker you always tried to be, and she isn't as ardently feminist, either," Sandy remarked with some pride.

She wasn't kidding. About me or Lisa. Though, I didn't know the extent of change in Lisa yet. As for me, I still wore my hair long, but kept it brushed and tied back. Also wore a shirt and tie to my workplace. I had an assistant managers job at a supermarket. No more beard either. I still rode a cycle but a less powerful Japanese model, not a Harley. I still kept myself trim, so did Sandra.

I hadn't finished college either. Only went long enough to get my Associates degree. As soon as Sandra landed a good paying job at a brokerage I quit school and got the supermarket job as a manager trainee.
Lisa drove here from California, and it took her seven days. Like my wife, she had plenty of potential in the looks department. Both were maybe five foot eight, and they kept their weight around 140, by exercise and sports. At least Sandra did. As for Lisa, she was like that in college.

I stayed fit also. About 155 on my five nine, medium frame. Lisa not only had stayed fit, from what I saw when she got out of the car, she had changed a lot. Wow had she ever changed!

For someone who had spent seven days in a car and hotels she didn't look any worse for wear. In fact the last hotel she stayed in must have had a beauty salon and boutique, because she looked like she'd been to both in the last hour.

She was a knockout! Jet black hair, naturally curly, to her chin, jelled and tousled. She was one half Latino and her coal black eyes were beautifully made up. She had a short skirt on with heels and hose. She smiled as she walked to our house and hugged both me and Sandra.

"Oh my goodness! It's just so wonderful seeing you both!" First she threw her arms around Sandra, giving her a huge hug and kiss. Next, I got the same treatment. I detected a real passion in her greeting. I wondered. We hadn't gotten along before. Maybe we both could change.

Soon enough I was at her car, removing her bags. "I'll put these in the downstairs, mother-in-law apartment," I smiled, "You might be with us a while, if you're planning on finishing school and all." Sandra had a real look of surprise at my sudden change of heart.

Throughout dinner I could see something was troubling Sandra. Even after dinner, up to bedtime she seemed absorbed and far off. Finally, when we were in bed for the evening, I asked her what was troubling her.

"Both you and Lisa. Suddenly, because she's Ms. Hot Chick, you want her to stay here forever. As for Lisa, she's really changed. I can't believe that a few years married on the west coast turned her in to a sexy trophy wife. I feel like an 'ugly duckling' around her," she said turning her back to me. Try as I might I couldn't get her out of the mood. Within a couple of weeks, though, I was glad I hadn't.

At the supermarket where I was assistant manager, I worked half days on Saturdays, and Mondays. This got me Sundays and Fridays off. Sandra's job at her financial services firm was the usual 9 to 5, Monday through Friday gig. Lisa would soon be going to school pretty much the same days as Sandra worked, but slightly different hours. Normally on a Saturday I drove straight home from work and often Sandra and I would jump in bed.

This particular Saturday, about two weeks after Lisa had arrived I came home to Lisa and Sandra coming out of the house looking pretty nice. Lisa was her usual hot self, and Sandra much to my pleasant surprise was wearing heels,. Her hair was up in a cute up sweep, and she had a nice tight knee length skirt and a low cut blouse on. She even had on dangling ear rings and makeup. She looked a little shy and awkward about it.

"Where are you to going?" I asked.

"I talked Sandra into a full make over at Gigi Labelle's," Lisa said smiling as she climbed into her car, adding, "We'll be there all afternoon, Bill. You may as well grab lunch at Busche's Inn. We'll see you at The Bistro for dinner. We have reservations for 7 p.m. for the three of us. Dress up. We will be looking really hot!" she said with emphasis on the word hot.

The salon she mentioned was one of the best and most expensive in town. Sandra could well afford it on her salary. I was glad to hear she was going. If Lisa had this sort of effect on her I was glad to have her at the house.

I was really glad to hear it and was absolutely stunned when I got to The Bistro. Sandra looked fabulous! Her makeover was first class. Her hair was now a shimmering, very coppery red, just to her shoulders, in bouncy curls. Her makeup had been done to emphasize her big green eyes. Her lipstick looked luscious. What a change!

Dinner was really enjoyable, and the lovemaking that night the best in years. Finally, my wife was dressing and looking like a hot chick! Over the next few weeks and months Sandra really got into how she looked. There was one thing I noticed the first time she had a perm put in her hair. While making love I noted that the scent of the perm solution in her hair turned me on! I know today that was the first sign of me being a beauty parlor pansy.

Lisa got right back into school and asked if she could ride my cycle there. Actually I decide to let her because I wanted to tool around in her Audi. I also owned a pick up, and Sandra had her Volvo. Lisa then started wearing leather outfits whenever she rode the cycle to school. In fact she occasionally dressed sort of like a Domme.

Now every chance we got, Sandra and I tried spicing our love life up by coming home at lunch if we could, to jump in the sack. We couldn't do it on days Lisa was home from school though. One afternoon, when I had expected Lisa home at lunch I called Sandra's work to find she had went home. I had wanted to do lunch downtown with her.

Steve, the manager trainee would always cover me during these trysts so I told him I was headed home for some fun. When I arrived I saw my cycle, my truck and Sandra's car. They were both home. Once I opened the door I heard soft music, and smelled incense burning. On my way down the hall, the door to our bedroom opened, and Lisa came walking out wearing heels and some sexy lingerie.

She looked a little surprised to see me but recovered quickly. From the room I heard Sandra call out, "Lisa, is someone there?" When Lisa told her it was me, Sandra said, "Oh, no!" I then asked Lisa for an explanation.

"Well Billy honey, why don't you and I set on the living room sofa and discuss it? Sandy won't be able to join us she's tied up right now," she said with an intriguing smile.

We sat down, and she began telling me one very surprising, and not altogether thrilling story. "You see Bill, during college, Sandra and I just weren't good friends, we were lovers. I was not only her mentor, but also, well, you might say I dominated her in more ways then one. So, would you like to join the party and make it a threesome?" she asked, pausing for my reaction.

"Wait Lisa! I can't believe this. You and Sandra? You are her Domme?" I asked incredulously, now realizing she meant literally that Sandra was really "tied up."

"My goodness Bill. You certainly don't think Sandy made this metamorphous from matronly aunt to fashion model to please her husband? I'm the one she did it for. Why should you care though? Come along honey. Let's take a look behind door number one," saying this she took me by the hand, announcing our impending arrival to Sandra.

Sandra's response was, "Please Lisa? Don't let him see me like this?"

"Like this," was kneeling on the bed, facing the headboard. Her wrists were tied to the corner posts. Her butt was bright pink. Sandra really did look lovely though. Beautifully made up with her hair "done." She was wearing a halter top, high heels and nothing else. She smiled at me prettily and then hung her head in embarrassment.

Lying on her left was a paddle and to her right a box of sex toys. The room smelled beautifully with perfume and incense. A CD of Celtic warrior princess ballads was playing. The old style songs had been electrified and the drums, stringed instruments and powerful female voices put me under a momentary spell, that was broken when Lisa touched me. "Well sweetheart? Care to join us?" she asked sexily.

"I don't think so! No I'll be leaving. Don't wait up," I said as I headed for the car.
Sandra called out to me, "Bill! Come Back! Please?

This was followed by Lisa saying. "Quiet wench! I'll do the talking around here!" Then a loud smack and my wife squealing loudly.

I sat in the car and Lisa must have opened our bedroom window as I could now hear the music again. This time I was definitely drawn towards the house and into the room. She had resumed her paddling of Sandra and stopped only when I cleared my throat.

She went to the CD player and turned the music down, saying, "So you have changed your mind! Sandra darling. What would you call a man who left you tied up and completely at my mercy?"

"I'd say he was a sissy and I'd also say he needed to be punished," stated my wife, recovering quite quickly.
Lisa untied her and they both began to undress me, turning the music back up, closing the window and humming and singing along with the songs as they stripped me and tied me up in the same position Sandra had been in.

Sandra quickly took charge saying, "I think we should spank the little trollop and then show her what it's like to be a girl. By the way Lisa, what should we call our new playmate?" she asked with a very domineering tone.

"I think that Brandy would be a lovely name for her. By the by love. Shouldn't we make her up first?" Lisa asked as I got really worried.

"Later. We'll do that before we get ready to pump her rear end," Sandra added as she began my paddling.
They broke me in, right from the very beginning. I had to count each stroke of the paddle, adding, "Thank you so very much for my correction, Mistress," following each stroke. In addition I was made to beg them to make me up "Really pretty", and to make me, "Feel like a natural woman."

The term "Rode hard and laid up wet," really made sense to me now, as I returned to work for the rest of the day. I was so embarrassed about going home that I stayed until closing, a few hours after I would normally have left.

It didn't matter though. The ladies were waiting for me to show me all the purchases of girls clothing they had made for me. I had been left hanging sexually also. When I mentioned it they had me strip and pull myself off into a glass of milk. Then Sandra had me drink it down saying, "That's for all the times you had me swallow."
They also began my preparation into girlhood, by shaving my body, thinning my brows and doing my nails.

"You learn to do this, because we plan on you doing this for us in the future. Wear pantyhose to work from now on and toenail polish. Keep that body hairless and smooth also," Lisa instructed me as if I were her slave. Then she added, "We're going to start thinning your eyebrows and have a little something done to your hair. Plus that right ear needs to be pierced to match the left one."

Sandra picked things up, "We're going to femme you up slowly. You won't go girlish, full time, until Lisa is working with me and bringing home some bacon. By the way. Don't be surprised when your relationship with Gladys, your boss at the supermarket changes. She's a friend of ours and is thrilled to be assigned the job of keeping you in line away from the house."

They really meant that. The following week when I went in my schedule had changed completely. Steve, the trainee was now assigned the assistant managers job. A new trainee was hired and I was relegated to the position of "Manager's clerk", which meant Gladys kept me around her office running errands and doing secretarial duties.

Before she would really get to embarrass me, Gladys gave me a brief reprieve, basically waiting for me to learn some beauty skills and also giving me some time to start dressing and looking a little more femme. My hours now coincided right along with Lisa's and Sandra's. They started teaching me housekeeping skills as well as how to do their hair, makeup and nails, as well as my own.

I dressed as "Brandy" around the house and for the most part they called me by that name no matter how I was dressed. Gladys pretty much used the name in private at work. In public she referred to me as her "Little helper."

Wearing heels was the toughest part of all, and although I only wore them around the house, the girls had one pair they tied onto my feet at bedtime and I wore those in bed. This would help my feet, ankles and legs to take a more comfortable set, so I could wear high heels all the time. I now occupied the guest room as Sandra and Lisa slept together.

Finally one Saturday the girls decided to have me "come out" not as a full fledged girl, but as a "sissy." The next couple of months would be about the most embarrassing of my life. I was actually relieved when my Mistresses would finally let me be a girl full time.

Lisa had gotten her Masters degree and would start working with Sandra at the brokerage on the following Monday. She had been recruited and interviewed for the job while still taking courses in school. It was Saturday. I would wear, for the first time in public, really effeminate, very sissified, unisex clothing. I was also going to "Have a few things done" at Gigi Labelle's, the same full service salon and spa., where both Lisa and Sandra had all their beauty services performed.

Going there dressed as an androgynous sissy was doubly humiliating. I entered this really ultra feminine place of business dressed in a pair of red hot pants, trimmed with a wide black belt and big silver buckle. My shaved legs, were shown off to full advantage as I had on white anklet socks and black patent leather Mary Jane shoes with inch and a half heels, purchased at a "specialty shop."

My hair was up in a little bun, wrapped with a slender red ribbon. I wore a white, short sleeved blouse with a high collar trimmed in lace. I held my patent leather purse, which contained my makeup, daintily by the straps, with the tips of my clear polished fingernails. My limp wrists, and flat chest, let everyone know I was a sissy.

Worse yet, before entering the salon I had been made to traverse the full length of the mall, without my mistresses, meeting them at the entrance to the salon. My tear filled eyes told them I'd heard my share of comments and laughter. Ms. Gigi Labelle herself was going to be working on me. She met myself, Sharon and Lisa in the center of the salon to discuss things. Naturally, I was in full view of quite a few amused people. When Gigi felt I had been on display long enough she snapped her fingers and said, "Claudette! Front and center!"

Mincing to the center of the salon, from the rear, came a really attractive beauty, whose raven colored hair, was done in tight curls. She was quite tall, though beautifully slim, and wore a French maids outfit. From the whistles of some of the ladies, I soon realized that Claudette was probably not a true female.
In her four inch heels Claudette was a little over six feet tall. Still she executed the most beautiful curtsey and said in a slightly throaty voice, " Yes Madame Gigi, what would you like Claudette to do?"
"I would like her to take our new friend Brandy to the rear of the salon, put a cape on her and give her a shampoo, hot oil protein pack and a creme and warm water rinse. Then prep her hands with skin and nail conditioner," Madame Gigi said firmly.

After another curtsey and a "Yes Mistress," I was led to the shampooing area. She hung up my purse, reaching for it with the same limp wrist and dainty fingered grip I held it with. Putting a cape on me, she shampooed my head as she gave me some pointers.

"In short my Mistress despises male conduct as much as she adores females. She tolerates sissies. While she works on you, be polite, obedient, and attentive. Speak only when asked a direct question. If you displease her at all, you'll wind up, behind that door to the left of the dryer. There she will discipline you. She'll probably use a thick, very wide, leather razor strap," she said as if this were a natural occurrence.
My head was washed, and the smelly, hot oil protein pack was worked in and I was simmered to well done under the dryer. What a relief I felt when my plastic cap was removed and my hair was cream rinsed with warm water and a strawberry scented conditioner! Seating me in the styling chair, Claudette began to massage my hands with a scented cream to prep me for a manicure. She would do my nails as Ms. Gigi did my hair.

"Well let's see. What do we have here?" Ms. Gigi said to no one in particular as she removed the pink towel which Claudette had wrapped around my head, turban style. "Very healthy, thick sissy hair I would say," she added with a smile.

She gave me a layered cut, leaving most of the length but thinning underneath. Then she set my hair really tightly on mid sized brush rollers and perfumed setting lotion, before leaving me with Gigi who completed my manicure with a creamy white polish. When Ms. Gigi returned she had a Mistress/sissy publication.
"Read this under the dryer Brandy. Claudette and I are featured this month," she said as Claudette put me under the dryer on medium heat. I was under the dryer a full 45 minutes and got a real eye full of the Mistress/sissy scene from the magazine.

Once the timer went off Claudette returned and checked my hair for dryness before removing the rollers. She left me to wait for her Mistress. I looked at my changed hair, now a mass of springy curls. While she did my comb out and spray Ms. Gigi counseled me on what to do.

"From here you will be going to a specialty shop similar to where you got your cute shoes. This place specializes in figure improving garments. After that you'll go to an obstetrician/gynecologist for an exam and some pills. If you'd like people to think you are a female instead of a pantywaist, I suggest you leave the specialty shop with a padded bra on. Also you may want me to do your make up now and the girls can touch you up along the way. What do you say Bran? Want to take a little walk on the wild side?" Ms. Gigi asked in a slightly facetious tone.

I really didn't have a choice, although now that I think of it, I might have waited for the shop ladies to do my make up. After all, now people at the mall got to see the sissy boy leave the beauty parlor with his hair "done", nail polish on and plenty of makeup, including bright lavender lipstick!
At least my lady friends walked with me through the mall and to the car. It didn't seem so bad when the people in the mall and outside teased me. Sandra held my hand and on the other side of me, Lisa put her arm around me. I sat in the back seat all the way to The Feminine Mystique, a shop that catered to cross dressers.

I was surprised at how young the sales ladies were, and how helpful, attentive and understanding they seemed towards me, especially. I tried on several waist cinches, corsets, ball bags and really serious gaffs. I also was fitted for bras and breast pads. Because my hair was now done in a stylized page boy flip, my mentors decided to forego the trying on of wigs for the moment.
"I'd hate to muss that gorgeous new hairdo, Brandy," Sandra had said, giving everyone but me a laugh. In addition we bought some training heels that had shoe locks, so I couldn't take them off. They could leave me at home all day in these shoes and I'd have to wear them until they unlocked them.
Next stop was a carry out lunch because I was too nervous to go in a restaurant. Then we were off to the doctors office. Dr. Chambers was a really nice lady who seemed to be used to transformed males. She now considered me "One of her girls."

"We only want to put you on a hormone dosage strong enough to retard hair growth and plump up your cheeks, butt and breasts a little, Brandy," she said really sweetly. "Take these for 26 days, stop for four, come in for a mild booster and start over again," she added before we left for home. As confused as I was, things would only get a little worse before getting better and clearing up.
I had no idea that whenever I stopped the pills I would get something similar to menstrual cramps, until I got the booster. I was really becoming a girl.

Chapter two: Trained and Transformed

After a weekend of wearing unisex shoes, slacks and blouses, with ladies under things, I was sent to work in stretch slacks, a ladies pullover top and some girlish flats. My hair was done in a slightly puffed back swept style. I had pearl studs in each ear, clear polish and a hint of waxy white lip gloss. The girls at work greeted me fine but the few guys there, steered clear of me. I was doubly embarrassed because of my little purse.
Gladys took me in her office and showed me my new desk and typing area. "You are to set here, with a nice pretty posture. Straight up, prim and proper. Legs together, very ladylike, and perched on your toes.

Tomorrow wear a slight heel. Everyone who comes in will see you from your profile side," she said firmly
and with a very commanding tone.

"You are to daintily limp your wrists to type. You will say yes ma'am and no ma'am, or sir if the situation calls for it. A sweet melodic voice when you answer the phone. You'll run errands, do my nails, get me coffee and keep the office clean. Any questions?" she asked and I told her I understood.

She then had me practice answering her phone, "Ms. Gladys Helm's office, Brandy speaking," I said in my most sissified voice. She smiled and walked to her desk.

The next month couldn't have been more embarrassing. The errands I ran were to lingerie and perfume shops to buy gifts for her lady friends. If I did her nails she always timed it so someone, male or female came in the office. She even had me purchase her douche, sanitary napkins and vaginal sprays, right there in the supermarket, along with cosmetics and nail polish.

Finally after an extremely trying day I went home and while cleaning up after dinner broke down crying and poured my heart out to Sandra and Lisa. "Please, please, please, let me quit work and dress like a real female!? I hate being a sissy secretary! I want to be your girl, your wife, your housekeeper, your maid!
Please, can I?" I begged like I'd never begged before. It worked, sort of.

The following Tuesday at work, during a shift change, Gladys had all the department heads, assistant managers and the head cashier in her office. Lisa and I were seated on a couch, Lisa with her arm around me. Gladys began speaking.

"I want everyone to meet Billy's very supportive sister Lisa. Lisa is here to tell you about the transition Billy is going through. We, Billy's friends are going to be very supportive of him for the next month," Gladys said in an authoritative tone, as the nine employees, seven women and two men, listened to my supposed sister, Lisa.

"I'm sure you have been wondering about my brother's increasing feminine appearance. Well, all his life he has struggled with gender dysfunction. He tried everything to be a normal man. Marriage, motorcycles, anything to fit the male stereotype. Nothing worked. He's now sought clinical help and decided to try the change. One of the things he needs to do to make the try successful is live as a female for six months and at least for one month, work as a lady. I appeal to you to be understanding and help him," Lisa said in an academy award winning performance.

The room was silent as Gladys explained I would be coming to work as her female secretary, Brandy, beginning next Monday. I was really surprised at the response. The guys smiled and the women actually hugged me. Gladys gave all the folks at the meeting all week to prep the rest of the employees.

These were the only conditions the girls would let me become a full time lady under. No sneaking around and hiding. I'd have to work at least 30 days as a female or continue as a sissy. The sex change story was just to add to my embarrassment and keep me humble and submissive. Now it would be even more difficult to ever dress as a guy again.

My first day as Brandy the secretary I decided to do my hair up in a modified beehive. I even wore faux pearls and a "little black dress," three inch hells and perfume. Full makeup of course with plenty of red lipstick.

The fun part was "doing lunch" with Gladys, and shopping sales with her. Gladys even took me to Gigi's to get my hair colored strawberry blonde. My wonderful boss also encouraged me to change my hairstyle dramatically every few days.

Up in a bouffant, down in a page boy, one side down and the other pinned back. I did braids, ponytails of different types, French rolls, and chignons. I really became a style queen, with my clothes, hair and makeup.

By the time the 30 days was up, and the girls gave me a going away party, clothing, hair and cosmetics were all I cared about. Housework? Of course. As a sissy maid I had to do that. Sex? Actually it just wasn't as important. I had become the woman I'd always wanted in my life. A really sexy looking, hot looking chick. Well dressed, beautifully coifed and made up.

Of course, as a lady's sissy maid, I also still enjoyed performing personal services for my mistresses, as long as these services made them beautiful. Again, if they really desired me as a boudoir maid, I felt compelled to perform sexually. You know what, though? It's a real drag to get really dolled up and get my clothes wrinkled, my hair mussed, my makeup smeared and my perfumed body, stinky and sweaty. Of course, then it's fun to doll up again.

Epilogue

"Yes Candy, what is it?" I say to the other sissy maid that Sandra and Lisa now employ. Lisa found Candy at a costume party and just couldn't resist offering her a job. Candy couldn't refuse. I'm not jealous at all. She is great in all aspects of sissy maid duties.

I'm just finishing my make up, filling in the magenta lip liner, with ginger matte lipstick. We're all going out in three hours and I want to look hot, especially at Club Siren. The femme lesbians there, and the sissies are really beautiful. Lots of competition, in a fashion sense way.

Candy realizes she'll never get my full attention when I'm doing anyone's make up, especially my own, but continues anyway. "The Mistresses want to know if you'll join us for some playtime, Brandy? It's not mandatory this time. I'd love for you to play though, they really wear me out when I solo," she pleads sweetly enough.

Not mandatory? That doesn't happen often. I pause and check my upswept hair, recently done in a perm. What torture it can be getting a perm! The tight roll up, the smelly lotions, the heat from the dryer! Then of course, now that Claudette and I are sissy friends, she whines about Gigi when her Mistress isn't around.
It's worth it though. Anything is worth doing if the results are, looking really good.

"Where will this take place Candy?" I ask as she walks away saying something about "Their room, where else?"

I continue my dolling up, and can't decide what to wear when Sandra comes in my room and pulls me towards her and onto my bed. "Please Sandra, you'll muss my do and smear my cosmetics!" I shriek like a chorus girl.

"Darn right I will, you little sissy femme. I'm going to take what's mine," she says very commandingly.
As a sissy, one thing I've never been able to resist is a command. She smears my makeup all over, when she kisses me and when she sets on my face to finally orgasm. My heavily sprayed hairdo becomes a glob of matted sweaty curls as she plows me from behind.

When I finally orgasm with her riding me on top, my perfume is blended with the sexy scents of satisfying sex. Was it worth it? You bet it was. As I said, now I get to doll the both of us up.

We head to the shower and I hear Candy whimpering and pleading in the next room. Then I hear, "Quiet wench! I do the talking in here!" Lisa was always such a feminist.

Ended?
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