Dedication
To little sambo
Who crossed
On June 10th
Never to be seen again.

And to Willow who shall
Blossom when she meets her
Soul mate.

Acknowledgments

Family, friends, and loved ones, thank you! Time is a precious gift and they have given me all the time I want, need, and desire to write what I have in my heart and mind.

Inspirations develope, quite often accidentally, from many sources and each has my gratitude. The ladies in the nail salon in St. Paul, the gentleman at the grocery store, the limousine driver, people in the general public, have given more than they realize!

anna of anna’s Erotic Art will give the cover of Lotterby a spark of erotic realism. Being a real time submissive to a real time Master allows anna to put on canvas real time emotions. Please take an extended tour of her web site anna's Erotic Art to view a magnificent collection of her original artwork.

The least likely person one would expect to be acknowledged in a book of erotica would be my cousin, a Southern Baptist preacher. He is the least judgmental person I’ve ever met. In all honesty, I can openly say I wish more people possessed his quality of acceptance of others, including me, for what they are rather than what they seem to be on the exterior.

Anna J. Lightfoot

Chapter 1 - Deana

Much to my parent’s dismay, my name is Sydney Lotterby. Ethel Lotterby never suited my personality so I legally became ‘Sydney’ the day I turned twenty-one. I am a thirty-six year old female who stands all of five feet tall and weighs just a smidge over a hundred pounds. I suppose I'm considered a pretty woman who has been blessed with high cheekbones complimented by deep brown eyes and dark chestnut hair. I usually wear my tresses in a tight bun at the nape of my neck when I leave my co-op. My neighbors, most of whom are wonderful people, see me with little makeup, an elegant suit or dress with low heel shoes, perfect manicure, and a pleasant smile. I'm soft-spoken at all times, and of even temperament toward each resident in our building, which overlooks Central Park in New York City.

"Why you work on Sunday, Miss Lotterby? Why you no take day off? Today good day to stay in bed with good book," my elderly neighbor, Mrs. Womanski, said to me in her broken English as I headed toward the elevator, briefcase in hand. "Rain too hard to outside doing anything."

"Now you know, Mrs. Womanski, there is no rest for the wicked," I told her as I pushed the elevator button for my ride down the ten floors to the lobby. Mrs. Womanski laughed and 'pooh-pawed' me as the elevator door closed.

The doorman greeted me with a tip of his hat and a bright "Good morning, Miss Lotterby," he said. "Yer up and out early, Miss."

"Good morning, Ralph." I answered as he held an umbrella over my head and walked me to my waiting car. "Stay dry!"

Several years ago I came to the conclusion it was much easier to hire a full time driver rather than drive myself. I constantly found myself in the financial district rather than SoHo but, alas, I had also earned too many speeding tickets driving to Connecticut on the Merit Parkway. My mind was never on my driving but on my real world in my lofts on Wooster Street or my little farmhouse on the fringe of Greenwich.

‘Lotterby’s Center of Gender Reeducation’ on Wooster was located among the eclectic galleries, markets, little shops and lofts in SoHo. My building blended in well. It is a six-story building, once a small factory. One would never notice the building unless specifically looking for it.

Should you be taking the elevator to the third floor loft, you were most probably a cross dresser, transgender, transvestite or transsexual seeking guidance in the fine art of becoming a woman of charm, elegance and impeccable social skills.

Men of means seeking my personalized training traveled from all parts of the country to learn how to walk, talk, dress, think and become the woman buried within them. I teach my pupils that becoming female included far more than wearing a pair of falsies and high heels while prancing around like a drag queen. It is a journey of the mind as well as the flesh; it is a journey, once begun, never ends; it is a journey of both pain and pleasure; it is a journey which could result in tears. It is a journey that could well end in tears of joy, freedom, and release.

It was quarter to eight when I picked up the Sunday Times then put my key into the deadbolt lock. Once inside with the door securely locked, I hung my raincoat and kicked off my sensible shoes in the foyer closet. I padded, barefooted, into my office.

My first pleasure of the day was to shuck off my sensible, acceptable, restraining, business suit. Naked once again, I selected a black leather corset, black thigh high stockings, skin tight black satin pants and five-inch black leather platform boots I would put on before my newest client arrived. I pulled three large pins from my hair then shook my head vigorously as my heavy locks of wavy hair fell to the middle of my back.

Naked and feeling unencumbered, I unlocked and pulled a folder from the filing cabinet labeled ‘Griffin, Dean Walter, Oklahoma City, Oklahoma’. Flipping through the folder I found Mr. Griffin’s original application, Dunn and Bradstreet report, a TRW credit report, copies of his license to practice law in Oklahoma and New York, and driver's license. Two pictures of the client, one in street clothes and the other wearing feminine clothing, were next in his file. The last item was a copy of his cashier's check to cover his six-day stay with me in my Wooster Street loft for training.

I removed the two pictures of Griffin. The first was a black and white shot of Mr. Griffin in his business clothes. It was the standard press release picture. I studied the picture. He was a handsome, clean-shaven man with 'power' etched in his face. He seemed a tall, slender, man with broad shoulders and a somber expression on his face. There was no spark in his eyes, no smile. His dark brown hair was cut short but didn't have that 'I just had a haircut' look. He wore a suit and tie, both conservative, both expensive. The copyright of a professional photographer was on the back of the picture.

The second photo was of Griffin dressed and in makeup. It was taken with a Polaroid camera and not the least bit professional. Miss Walters wore an expensive full-length evening gown, a flashy blonde wig, too much makeup, too much pink lipstick, and too much gaudy jewelry. The look on her face was vastly different from the previous picture; Miss Walters was smiling and her eyes were alive and joyful. She seemed relaxed. Comfortable. Happy.

After reviewing Griffin's application I remembered what had originally attracted me to him. He was not only a cross dresser, he was also a submissive masochist who would welcome my strict punishment in order to correct his/her bad habits.

I smiled. I had chosen the right outfit to wear for meeting Mr. Griffin/Miss Walters for the first time.

Putting the Griffin file aside, I spent some time reading the New York Times and last Friday’s Wall Street Journal. My stocks were holding firm as the stock market fluctuated. The mutual funds were okay but not great. I left notes for Monday as to which stocks to sell and which to buy. Gloria, my secretary, would take care of the transactions.

At a quarter past nine, I folded the newspapers. It was time to refocus on the honorable Mr. Walters, Esquire. Before putting the file back in the filing cabinet, I glanced at the application once more. Dean Walter Griffin was also Miss Deana Walters. The feminine name was not innovative but understandable. I replaced the file and locked the cabinet. Miss Deana Walters was due at ten.

I was a nudist in my home but as Miss Lotterby, Head Mistress of the Center, I dressed appropriately for the occasion. Today was, indeed, a day for fetish clothes to be worn. After I had hooked on the strapless leather half corset I pushed my breasts inward and upward giving me an abundance of cleavage. The tight corset ended two inches above my waist. The satin and spandex pants slung low on my hips, hugging my legs. After scrutinizing my image in the full-length mirror, the boots were replaced with a pair of five-inch spike-heeled black slides. A sexy outfit, if I did say so myself. With a few strokes of eyeliner and gray shades of eye shadow, I again checked myself in the mirror. I bent at the waist and shook out my long hair. Mrs. Womanski would have fainted should I have knocked on her door dressed in my work clothes. The change was dramatic.

A few minutes before ten, there was a light knock at the door. I waited until the stroke of ten o'clock to respond.

I slowly opened and stood behind the door. Dean/Deana heard a female voice, mine, tell him to step fully into the room and set his luggage on the floor. He hesitated.

"Now," I said in a soft but stern voice, "or turn and leave." I'll bet only a few things had frightened Griffin. He was shaking in his shoes as he stepped into the foyer and placed his luggage in a neat little row to his right.

I told him not to turn around until I gave him permission to do so. The door closed and Griffin heard the distinct sound of the deadbolt lock click into place.

"Remove your manly clothes. You won't need them while you are with me."

Griffin slowly began to take off his shoes and socks. I smiled. He removed his jacket then loosened his tie and unbuttoned his shirt. Once the shirt and tie were removed they joined the jacket on the suitcase. He unbuckled his belt and unzipped his suit pants. He vacillated in the removal of his pants but, taking a deep breath, he stepped from them and they also joined his neatly folded clothes.

Attorney Dean Walter Griffin, eyes closed, stood in my foyer wearing a pretty white camisole, a pair of red frilly panties, a sexy red garter belt and seamed black stockings.

"You may turn around, Deana." Hearing the name "Deana" for the first time was unexpected. "Don’t be afraid, Deana. Turn around."

Never having seen my picture Deana was unsure of what to expect. We had talked extensively on the telephone prior to the exchange of funds. As with all of my clients, Deana had formed a mental image me. As Deana turned to see her mentor for the first time, she was surprised at how tiny I was in real life. My sultry voice gave the impression of a much larger person.

The outfit I'd chosen was not only unexpected but, I'm sure, highly arousing. Deana finally noticed what I was holding in my right hand. I knew her heart literally skipped a beat. I was holding my menacing black leather, riding crop!

"Miss Walters, you have a hard-on. Your red panties don't look nice with a large bulge. Now I ask you, is that any way for a young woman to react?" Deana shook her head. "Other than that one large flaw, your under garments are adorable. Did you pick them out yourself?"

Deana nodded.

"Hang your manly clothes in this closet." Deana complied with my command, without speaking, and I closed the door, locking it with the same key I had used to unlock the dead bolt in the front door. "You won't need these while you are here, Deana, will you?"

Deana shook her head. I walked behind Deana and gave her a gentle little swat on the fanny with the crop. "I expect you to talk, Deana, not shake or nod at me." When Deana nodded yet again, the crop landed smartly on her pretty red panties. The sting was enough to bring an "ouch" from her.

"It's good to find you do, indeed, have a voice, Miss Deana Walters. Be a good girl and collect your luggage. I'm going to show you to your bedroom and give you a quick tour of the loft. After that, we will unpack your bags and get you settled into your room. You'll enjoy your stay here for more reasons than you can imagine." I smiled at Deana. The smile had a wicked tint to it. She shivered.

Deana picked up her luggage and followed the clicking of my heels. There was an elegant strut to my walk and I knew Deana wondered if she, too, would learn to walk with an air of confidence while wearing spike heels.

Unfortunately, the huge bulge in her red panties was back and she had thoughts, evil thoughts of lust in her mind. How did I know? I have a full wall mirror at the end of the hall and could see everything happening behind me. Experience has taught me what goes on in the client’s mind before he sheds his male self and concentrates on the female side of the brain.

We passed a large gourmet kitchen which would rival any in the city, a spacious and richly furnished dining room, and finally, a large and beautifully appointed formal living room.

"This will be your bedroom, Deana," I said as I opened a door near the end of the hallway. "Put your luggage at the foot of the bed for the time being."

Deana placed her luggage at the end of the canopy bed. She scanned the room, decorated in light shades of pinks and corals, ruffles and frills, erotic photographs. She seemed to relax and feel more at ease.

Each minute detail in the bedroom had a feminine flair. The bed linens, subtle wallpaper and drapes were Laura Ashley. On a round table near the window stood a beautiful jade statue of a nude woman, her arms seductively stretched over her head. Gracing the east wall was an oil painting of two women, one clearly submitting to the other by bowing, head down, at the feet of the standing woman. A trio of paintings hung on the west wall, each depicting women wearing magnificent dresses, each of a different era. Deana couldn't take her eyes from the pictures.

"I see you like the pictures, Deana. They are former students. So is the statue."

"You mean these are all men?"

"No, Deana, they are women in their minds and hearts, ergo, they are women. I commissioned the jade piece of Pricilla after her surgery. She's lovely, isn't she? Pricilla was a student during her pre-op year of learning how to be a woman in the real world rather than behind closed doors. She will be helping you with your cosmetics and hair."

I noticed chill bumps on Deana's arm. "Are you warm enough, Deana? You aren’t wearing many clothes, my dear."

"No, I'm okay."

"Interesting, Deana. A man would say 'I'm okay' but a woman probably respond with 'I'm fine, thank you.' In order to be a woman, Deana, you must begin to think as a woman thinks. We are, after all, the gentler gender, aren't we?"

"Yes, ma'am."

"I'm sure you're exhausted from your trip and you'll have time to rest shortly. You have a full bath with a shower stall as well as a Jacuzzi all to yourself. Maybe a soothing bubble bath or quick shower then relaxing in the Jacuzzi would be nice before we have dinner with our guests?"

‘Guests? She never mentioned guests! She said instructors, yes, but never guests! Do I say anything or just keep my mouth shut? What if somebody recognizes me? Good God, I made a mistake coming here!’

I could see Deana's mind was afire with fear of discovery, of being outted, of being labeled as a homosexual, dominated his thoughts. It was a normal fear showing on his face; one I’d seem many times.

"Deana, snap out of it! You are thinking like Dean and I won't stand for it! During your stay with me you are Deana, not your male counterpart, and you will think like Deana, not Dean!" I softened my voice. "Come with me, dear."

‘Good God, she's a mind reader! I'm doomed." I walked to and out of the door; Deana followed like a good little girl. "This is the second bedroom. I may be spending a night or two here with you. You'll never be alone; someone will always occupy this room or be sleeping with you at night."

Though not as feminine as 'her' bedroom, I could see that Deana loved the sleek lines of the second bedroom with its massive brass bed, antique-looking Shaker dresser, amour and chair. In contrast to the Shaker designed furniture the walls were adorned with black and white pictures of women in varying degrees of dress from saloon girls to two naked women making love.

"Are these all men, too?"

I ignored Deana's question and pointed to a closed door on the far side of the room. "The bath is over there, Deana. Why don't you go and take a peek?" I smiled. The bathroom adjoining this room was not in the least feminine. I had it decorated in black and white. On the wall was a framed black-and-white portrait of a naked woman on her knees with her hands bound in front of her, her mouth gagged, and her eyes begging for something. In the forefront was a coiled whip being held by a female wearing thigh high boots, facing the imploring woman. The photo gave rise to the imagination; was the begging woman begging the Domme to stop or for more of the whip?

The bulge had return to Deana’s silky red panties. She'd been so engrossed in looking at the picture she didn’t hear me walk up behind her. She felt my hand clinch her engorged penis as the other grabbed her balls. Each hand squeezed with an iron like grip and Deana dropped to her knees in excruciating pain.

"As a general rule, women don't have a hard-on. As a strict rule here, Deana, you are not allowed an erection without permission. My permission." She clutched her painful groin after I had released my grip and stepped to face her. "I do hope we understand each other on that note, Deana, as I would be forced to discipline you for disobedience. Do we understand each other, Deana?"

"Yes, Ma'am, we have a clear understanding."

"Excellent! Although I do enjoy seeing you on your knees, if you are able to stand, do so, Deana." She flinched as I again gave her the smile with the same tint of wickedness.

"I have a question, Miss Lotterby," Deana said as she was standing up. I nodded indicating she could ask her question. "Why do you keep using my name over and over again?"

I gave her a genuine smile. "Why? To help you remember the reason you came to me, Deana. Your male name is locked in the closet with your male clothes. The more you hear your feminine name, the more you will identify yourself as Deana Walters."

"It's beautiful here." I'm sure Deana felt like a dunce but couldn't think of anything else to say.

"I want your stay, Deana, to be reeducational as well as pleasant. Having peaceful surroundings helps the soul absorb the essence of whom and what you are inside."

"Thank you."

Deana's voice was noticeably softer. Her body had taken a gentler, more refined, manifestation.

"Let's go unpack your luggage, Deana, and then it will be time for lunch. I own a sissy maid, Missy, who is cooking and she'll get her panties in a twist if we're late."

We began to walk back to Deana's room as an attractive woman approached us. She was dressed in a designer suit and carried a steno pad. Poor Deana was bewildered. "Good morning, Miss Lotterby. I have your appointments for the week if you have time to go over them with me." Her voice was soft and sweet but formal and business-like.

"Deana, I'd like for you to meet Gloria. She is my submissive and secretary. Gloria, this is Deana and she is our full time guest for this week."

Deana acted as if she suddenly remembered how she was dressed. If Gloria was surprised, it didn't register on her face.

"It is a pleasure to finally meet you, Miss Deana. I hope you enjoy your stay as much as I did. In fact, Miss Lotterby can't get rid of me now."

"You're a man?" The words were out of Deana's mouth before she could stop herself.

I frowned, but Gloria smiled and spoke before I could get the words out of my mouth.

"I'm pre-op. I work here on a full time basis; Mistress gives me a dash of courage or reinforcement when I need it. I owe her more than I could ever repay.

I lived for so long thinking I was crazy for hating my penis and being male; she helped me realize that inside everyone there is at least a little bit of a woman at heart."Gloria laughed. "In my case, there’s a little bit of a man inside and a lot of woman! Women, especially women such as Miss Lotterby, are truly superior!"

"Why don't the three of us go into Deana's room and give her a hand unpacking, Gloria? After that, Missy should have lunch ready and we can go over the schedule while we eat."

"Miss Pricilla is due at three today to begin hair and cosmetic lessons with Miss Deana."

"Perfect timing, Gloria, thank you. You, Deana my dear, are one lucky girl to have Pricilla available to help you with your makeup so early in the week. Let's get the unpacking done; I want to see what you’ve brought, Deana."

As they walked, Gloria asked, "Deana, are you a CD or transgender?"

"I just enjoy being in women's clothes. I don't have any plans on having any of my parts moved around or altered. I came here to learn enough so I can pass, if that’s even remotely possible. So, I guess I'm a run of the mill cross dresser."

"Missy is a CD. All she's interested in is being a maid and wearing the maid's uniform. There's something about the uniform and cleaning that she loves. She's a good cook, too."

"How old were you when you first started dressing, Gloria?"

I loved conversations such as this one. A new student guided by an 'old-timer' was the best reeducation in the world.

"I've always been trapped inside the body I was born with. It wasn't a matter of dressing for me, Miss Deana, but of being the woman I should have always been. I'm thirty-two and I just could not see myself living the next thirty or forty years being as miserable as the first thirty-two have been."

"I'm almost fifty-three. I have a wife and two children in college. If they knew I dressed I'd be divorced with two estranged kids. I'm taking a risk just being here."

Once inside her room, Deana said, "May I find my robe first? I feel silly walking around half dressed." Deana looked for her luggage. In a panic she shouted, "My bags are gone! My clothes have been stolen! My bags are gone!"

Missy, wearing her French maid's uniform with fluffy crinolines, thigh high stockings, four-inch heels, and a blond wig came out of the bathroom, smiled and curtsied. She also sported a black mustache and beard. "Miss Deana," she said in her natural baritone voice, "your clothes are put away, not stolen. Your pretty dresses are in the closet and your undies are in the dresser. I put your wigs and personal grooming items in the bathroom closet; your makeup is in the vanity. You have a beautiful wardrobe!"

The Dominant side of my personality came rushing out. To say the least, I was not pleased with my maid. "Missy, how many times have I told you not to assume duties unassigned to you? Go directly to the punishment room, Missy, and wait for me! I am not happy with you and when I'm not happy, you can bet your pretty bottom you won't be either!"

"Please don't punish her, Miss Lotterby. She really didn't do anything wrong," Deana pleaded.

"Just who do you think you are, Miss Deana Walters, telling me how I should treat my maid? Perhaps a taste of the paddle would do you good, too! Go with Missy to the punishment room!" Missy scurried from the bedroom followed by a bewildered yet excited Deana. "Gloria, you needn't see this; find something else to do."

"Yes, Miss Lotterby, thank you." Gloria left as quickly as she could. Pain of any sort upon others upset her; the thought of what was going to happen to Missy, and perhaps Deana, was enough to make her cry.

I opened the door to the punishment room to find both Missy and Deana standing, side by side, in the far corner. The whispering between them came to an abrupt halt. Missy gave Deana a slight nudge of her elbow.

"Miss Lotterby," Deana pleaded, "there was no damage done. Missy was just trying to be helpful. That's all she was doing. Trying to be helpful."

"Be quiet, Deana," I said in a harsh tone. "You don't know what you are talking about. Missy knows the rules, don't you Missy?"

"Yes, Mistress, I do."

Deana gave Missy a look of surprise. I knew Missy had tried to talk herself out of punishment by using Deana as a go-between. By doing so she was well aware that her punishment would be twice as harsh. Topping from the bottom was a trait Missy had tried to master for years. This time she may have gotten her wish.

"Missy, I've allowed a few little things to slip by lately but your inappropriate behavior this morning has pushed you to the line. You seem to have forgotten I own you, you are mine, and you do as I command, not what you may think I want of you. Asking Deana to cover for you only makes matters worse, young lady. As far as I’m concerned, you planned this event and you will pay dearly for both the inappropriate behavior and the planning. In this case, you’ve chosen your punishment partner well."

Deana seemed to suddenly realize I have two distinct personalities. She now knew ‘Miss Lotterby’ who runs the school and also ‘Mistress Lotterby’ who was the Dominia and, without a doubt, a sadist. A look of surprise registered on her face.

"Missy, your punishment is for not obeying my rules and for topping from the bottom. Deana, you will witness the punishment to give you incentive to obey my rules!" I looked directly into Missy's eyes and said, "Kneel on the spanking bench and be quick about it."

"Yes, Mistress." She was almost running to the bench located in the middle of the room. As she knelt her frilly white crinolines arched about a foot into the air; her panties covered her ass.

"Deana come over here and pull her panties down."

"Yes, Ma'am." Deana was still wearing her silky red panties, camisole, and stocking with the red garter belt. Finding her robe had been forgotten once Missy confessed to having put Deana's clothes and personal belongings away.

Deana went to the left side of Missy and, for a split second, hesitated in pulling down Missy's panties. As if in slow motion, she reached under the crinolines and found the waistband of Missy's frilly-bottom white panties.

"Are you getting excited, Deana?" She began to pull the panties over Missy's fanny; Missy had a perfect bottom, nice and round, well padded with ample muscle and tissue. "Are you worried about an erection, Deana?"

Deana lowered Missy's panties until they were around her knees. She stepped back from the spanking bench. Deana was shaking, inside and out. "Is this what you’ve been looking for, Deana? A mistress?"

She nodded.

"Did I tell you to move, Deana?" She didn't answer. "Deana, did I give you permission to step back?" My voice was that of another woman; I was hardly the tiny little thing Deana had seen up until this incident.

"No, Ma'am."

"Well?"

"Ma'am?"

"Get your pretty self back where you were, Deana, and be quick about it."

"Yes, Ma'am," Deana said. It was easy to see that her brain was on hold. Deana slowly stepped forward to the bench.

"Now, Missy, you are going to get a spanking you'll remember for a long time. You won't be sitting for a week!" I looked at Deana. "Pay close attention, Deana. Don't take your eyes away from Missy's bottom."

"Yes, Ma'am." Deana's voice was shaking!

As the spanking began I used my best toy; my hand. Deana's eyes were glued to Missy's bottom. At first the snacks to Missy's bottom were light and easy as my marvelous hand made contact. The cheeks of her fanny had become a light pinkish glow.

"What's the safe word, Missy? Tell Deana the safe word."

"'Stop', that's the safe word, Mistress."

"Bad maid! I told you to tell Deana, not me!" The slaps became harder and Deana could see handprints on Missy's pretty almost-red bottom.

I turned to Deana. "The safe word is always the same: stop. If you say stop, I'll stop what I'm doing until you are relaxed and ready for more. Did you understand what I just said, Deana?"

"Yes, Ma'am. The safe word is 'stop' and you will stop for me to relax."

"Good girl, Deana."

The slaps to Missy's bottom were becoming harder with each strike and her color had changed from light pink to a dull red. Missy was beginning to squirm on the bench. "Do I have to tie you down, Missy, or are you going to be still and take your reprimand like a good maid? I know you hate bondage so you'd better be still, worthless maid."

At the word 'bondage' Deana’s erection begin to grow in her revealing silky red panties.

"Put it out there, Missy, and don't let that sissy-clit of yours get hard. No erection for you, Missy!" My strikes were getting harder by the slap.

Missy boosted her fanny into the air as commanded; her sissy-clit was already engorged with blood and pulsating with every strike of my hand. Missy had a cut penis and its head was deep purple. Alas, her crinolines hid her sissy-clit and she could only hope I didn't look under them.

I put my hand under the crinolines and felt for myself what was happening; an evil smile came across my lips; the lips of Mistress Sydney, sadist.

"Deana, pull Missy's crinolines up over her head."

While Deana was struggling with the maid's uniform, I went to the closet to get a towel that I placed on the spanking bench to collect any run-away precum. "Look at her, Deana! Look at how big her sissy-clit is getting to be and I told her not to become erect! What a naughty sissy-maid she is! Wouldn't you agree, Deana?"

Deana didn't move, didn't speak, and probably didn't dare think. I saw her red panties were now fully tented with her own erection. As scantly clad as she was, Deana knew I could see her configuration.

I smiled as I reached under the spanking bench and retrieved a wooden paddle. I slowly used it to circle Missy's extremely red bottom. I knew the cool wood felt good on Missy's hot bottom as it circled each cheek. As if it had a life of its own, the paddle began to lightly tap on Missy's fanny.

"First you assume duties not assigned to you and now you have an erection, Missy. Yet another offense to add to your collection of demerits."

The paddle came down on Missy's bottom with a loud smack which seemed to echo throughout the room. Missy howled in pain. Again the paddle found its mark. Missy began to beg, "Please, Mistress, I'm sorry about unpacking. Please, please, I promise I won't do it again. Please, I beg you to not paddle me! I’m sorry I involved Miss Deana, Mistress."

Deana was breathing so hard I thought she was going to pass out. Never having been under the tutelage of a Mistress, Deana didn't realize the error in judgment she was about to make.

She reached down to her crotch and began to stroke the outside of her panties. I’m sure it felt so good, so wonderful, she wasn't thinking past her throbbing penis.

"Mistress, pleaaaaaaassssse!" Each of Missy's cheeks received four especially hard paddle strikes and her fanny was on fire with heat and pain.

"Deana, rub her bottom. Feel how hot it is. Feel the way her flesh has swelled from the paddling. Feel her pain."

Deana's hand eagerly moved over Missy's bottom, from the cool of the untouched skin to the heat of the paddled area. She felt the way her fanny did, in fact, seem to swell where the paddle had landed. I could read Deana’s mind through her eyes, which were pleading, ‘I need this! I want this! I WANT this!’

I retrieved Missy's butt plug from under the bench and was generously applying lubrication. Missy, sobbing, buried under crinolines, was incapable of seeing the butt plug and Deana was too involved in rubbing Missy's fanny to notice anything.

"You made three major errors today, Missy, and you have three punishments due. This is the second!"

With a single, pitiless thrust, I inserted the butt plug into Missy's ass while Deana was still rubbing her left cheek. Missy screamed.

Deana's erection began to drip precum as she instantly withdrew her hand.

"This will be your third!" The paddle was once again put into use and Missy received five more strokes on each cheek. Each strike of the paddle landed smartly on her already lobster red ass.

Instead of crying or sobbing or begging for Mistress to cease, Missy became quiet and her body seemed to relax. Her endorphin and adrenaline levels had reached the point where she no longer felt 'pain' but pure pleasure as the paddle reached its mark; her mind was soaring, flying, and she was in her own special, wonderful, point of unadulterated peace.

Deana shouted, "I need that! I want that!" She was near ejaculation. I ignored her. She bent over Missy and began kissing and rubbing her neck. She was whispering into Missy's ear as I secured the butt plug. Missy scarcely stirred while the plug was bound with duct tape into her sissy-vagina

"I want that, too!" Deana’s voice was trembling and almost muted.

I continued to ignore Deana as I gently and with compassion helped Missy from the bench. I knew Deana had never witnessed care such as I was giving my Missy. I 'walked' Missy to her nearby double bed and helped her to lay down then covered her with the sheet and thick down comforter. I sat beside Missy and stroked her and kissed her and talked to her and whispered in her ear and did wonderful things for her. Missy was sleeping like a baby before I would consider leaving her side.

Deana, dazed, was still standing by the bench with her hand on her crotch, rubbing the silky red panties now abundantly wet with precum.

"You, little cum-queen, have broken my rule, haven't you?" I began walking toward Deana; I kept my face stern and without a hint of a smile as I spoke.

"Yes, Ma'am, I did."

"Do you think you are going to receive punishment as Missy had?"

"Yes, Ma'am, I do."

"Is that what you want, Miss Deana Walters? Do you?"

"Oh, God, yes Ma'am, I do!"

I stripped off my black thigh highs. "We don't always get what we want, do we?"

"No, Ma'am."

"You want to have your body over the spanking bench and you want a hard spanking with the wooden paddle, don't you?"

"Yes, Ma'am, I do."

"Tell me why I should give you what you want."

"Well, ah, you told me I wasn't allowed to have an erection without your permission and I did."

"Oh, you did more than that, cum-queen." As I spoke, I walked to a straight back chair and a small stool beside it in the far corner of the room. "Come over here."

Deana darted to the chair; she was excited and apprehensive at the same time; her adrenaline level was sky high. She was over fifty years old yet looked like a little girl waiting for Santa Clause to come down the chimney. I wanted to laugh but kept a stern expression as I watched her scamper to me.

My voice was hard and cold. "Is this why you came to me? To have the discipline you think you so richly deserve? Do you desire to be a woman and dress like a woman or did you just want your ass beaten every day for a week? Is this how you get your rocks off?"

"Oh, Ma'am, I came to you to learn how to be a better woman when I am able to dress. I honestly didn't realize you are a Domme. When I first saw you this morning, dressed in a leather corset, I had hoped you were but I didn't know for sure until I saw you spank Missy." Deana couldn't stop talking. "When she called you 'Mistress' my heart skipped a beat, Ma'am. When you said that you owned her, I practically fainted. I've been searching for a Mistress for years. I need a strong woman to keep me in line and use whatever punishments she deems necessary. Oh, Ma'am, you have no idea how excited I am to know you are a Dominant; a skilled and wonderful Mistress and Dominant Woman!”

"Stop! Enough. You've made your point, Deana."

I sat in the chair and put my right foot on the little stool. "Do you know what OTK means?"

"It means over the knee, Ma'am. It's a type of spanking." Deana was almost panting.

"Take off your panties."

Deana quickly removed her red panties, wet with precum, and stood in front of me with a full erection; little droplets of precum were visible on the tip of her grossly enlarged sissy-clit. I kept from smiling at her eagerness. Little did she know!

"Give me the panties." Deana handed them to her. "Kneel in front of me and open your mouth." Deana knelt and opened her mouth.

"Wider!" Deana fully opened her mouth. I then crammed the precum soaked panties into her mouth!

"You had an erection without my permission, Deana, and that's not going to go without punishment. Bend over my knee! You are going to get the discipline a recalcitrant young woman needs." Deana began to bend over my knees. "Make sure your silly little sissy-clit is between my thighs!"

Deana did as ordered. My thighs tightened around Deana's sissy-clit until I knew it hurt.

"You are going to get a spanking and you are not to cum until I allow you to cum. You've broken one rule in the short time you've been here; don't break another Deana. You are not to cum until you are told to cum! Do you understand, cum-queen?"

Deana, her mouth full of her own cum-soaked panties, nodded her understanding.

I didn't 'warm up' Deana's bottom as I had done with Missy. Her hits were hard and fast and it took little time before Deana was cringing at the sting each time the palm of my hand struck. First one cheek, then the other until Deana's brain was swimming in hormones.

When I thought she could take no more, I said, in a murmur, "Fuck my thighs, you silly cum-queen!"

These seemed to be magic words to Deana and she began to pump her sissy-clit between my tight thighs. Each time her ass went into the air it was met with a hard hit from the palm of Mistress Sydney Lotterby’s strong hand. Deana pumped faster. She was not aware of anything but her cock, now her sissy-clit, and her bottom being slapped. Nothing else in the world mattered to Deana but her feelings of pain and pleasure, pleasure and pain!

"May I cum, Ma'am?" Deana was mumbling through the panties in her mouth.

"No." I used a soft tone in my voice but the meaning was clear "No, you may not."

"I can't hold it, Ma'am! Please may I cum?" Deana garbled through her wet panties.

"No. Pump and fuck my thighs and cum when I give you permission! Not before, cum-queen!"

"Dear God, I'm going to cum!"

"No, you aren’t. Pump as you were ordered to do, cum-queen! You will wait for my permission, won’t you, Deana?"

Deana nodded her head and continued to thrust upward as her ass was slapped with each pump. Her precum slid down my leg.

"Now! Cum now! I want to feel you're hot cum on my bare legs. Cum now, cum-queen. Cum hard for me; Now!"

It seemed as if Deana had cum stored for years that kept shooting onto my legs and dripping to my ankles. All the while, Deana's ass was being spanked and that enhanced her entire ejaculation. She squealed in blissful agony!

When she had at last finished her orgasm, Deana was drained. She lay limp over my legs. The panties were removed from her mouth. "You aren't finished yet, cum-queen. Get off of me and lick it up. Clean my legs with your tongue and do so now!"

Deana couldn't believe her ears. I could tell that this was not something she'd counted on doing. Could she comply with this command? Lick her own cum?

"Clean my legs with your tongue. You have the choice of obeying or leaving. Lick or leave. Now!"

Breathless, she said, "I've found my Mistress."

Deana slid from my knees and began to lick her cum from my legs. I knew she'd never tasted the taste of her own cum; the salty-sweet, musky taste was new to her. But she did lick every drop of her own cum. I thought she also realized she had been ordered to do so by a superior, strong, Dominant woman.

Missy began to stir in her bed; she moaned for her Mistress. "Come with me, Deana, and we'll see how Missy is doing. She got quite a hard paddling and needs a little TLC from us. You may crawl on your hands and knees behind me to the bed."

Deana didn't hesitate. She crawled to the bed. I felt Deana was humiliated yet stimulated by the power of the woman she wanted to call 'Mistress.'

"Deana, climb into bed and cuddle with your sister. Wrap your arms around her and keep her warm and snug." A genuine smile crossed my lips, the lips of Mistress Sydney Lotterby, a loving sadist.

Deana climbed into the bed. She snuggled against Missy and they both fell asleep.

At noon, there was a soft knock on the punishment room door. "Come in."

Gloria came into the room. "Miss Lotterby," she whispered as not to wake the sleeping girls, "I took it upon myself to finish the luncheon preparations. Whenever you are ready to eat, I can serve. Missy, I'm sure, will be groggy for the rest of the day."

"Thank you, dear; that was thoughtful of you. As you said, Missy is in la-la land. Groggy isn't the right word. She's in utopia."

I put my hand on Deana's bare shoulder, "Deana, it's time to get up. Go into your room, shower and choose a suitable outfit for this afternoon. I'm going to shower while you dress for lunch and Priscilla's visit to help with your makeup and hair."

Hearing voices, Missy awoke. "Missy will join me in my shower. Would you like that, little maid?"

"Yes, Mistress, will you allow me to wash you? May I brush your hair?" Missy was glowing from ear to ear with the thought of assisting me in my shower.

"We'll see, my little Missy, we'll see." I smiled down at her.

'Miss Lotterby' was back. Deana could feel my change from ‘Mistress’ to 'Miss Lotterby' in the way I moved and spoke. Deana, I knew, was a bright little girl. Deana Walters, truly, was going to enjoy her week at Lotterby’s Center of Gender Reeducation.

Back to MzAnna's Home Page

Back to MzAnna's Story Page

MzAnna
All Rights Reserved
Copyright 2003
A Lightfoot Publication