Skip to toolbar


by slave kellie

When I applied for the job with job with C. Thompson and Co., the interview was conducted by a shapely, dark haired girl, about my own age. The plaque on her desk announced her as Tasha Donaldson. My instinct was to josh along with such a pretty lady, maybe even invite her out to lunch, but she was all business. The job I was after was perfect for me and it was obvious enough I had to meet with Miss Donaldson’s approval before even getting to see Mr Thompson. I responded courteously to her questions, tried to make a good impression.

Holding my precis, she proceeded to check out each item, asking searching questions about my experience, and at the same time giving me appraising glances. I was glad, my shoes were polished, suit pressed, clean shirt and best tie. I hoped she approved of what she saw, knew that I liked what my glances at her revealed. A crisp blouse bulged sweetly. The legs I saw through the desk keyhole were shapely. She was wearing heels and dark nylons, which foolish as I am, made me wanted her for a boss. “You seem to be well qualified , Kenny, “she observed, after the catechism.

“My present employers want me to stay, Miss Donaldson. Of course the opportunity is much greater here.” I had not missed her matter of fact use of my first name, did not think I should respond in kind, “Will you be my boss?” The way she replied made me think I had a good chance. “My name is Tasha and yes, I will be your boss. A bossy one too, as you’ll find out.” There was a little smile with that remark, but it was plain enough she meant it.

I could not think of an appropriate reply. Any suggestion it would be a pleasure to work for such a lovely lady might have been taken for being a smartie. I wanted that job in the worst way. Tasha asked me a few more questions, learned I was single, living alone. She did not record the answers and I had a feeling she was not supposed to ask. I didn’t mind, she could ask about girlfriends, if she wanted to. I didn’t have any. No wedding ring on her 4th finger either, but in my experience, beauties like that have already taken up residence with some gent who straightens horseshoes for a hobby. While I was musing along these lines, Tasha dismissed me. Her manner of doing it was proof positive she would be the boss. It was not a suggestion. Orders! “I’ll need some time to check your references. Go out and have lunch. Be back here at 1 PM.” There was no temptation to suggest the busy lady have lunch with me. I did wonder thought when I was going to meet Mr Thompson?

Promptly at 1 PM, I reentered Tasha’s office. She was watering some plants. The first sign of femininity. Out from behind the desk, her figure was good to look at. Standing in profile she displayed the mouth watering forward curve in the blouse area, and an equally attractive backward bulging where she sat down. Still intent on plants, Tasha asked “When can you start work?” I answered a delighted, “Just about any time. Right now, I’m on vacation from my present job. That will take care of the notice.” “Let’s make it Monday morning 8 o’clock. I can spend some time with you before we start work at 9.” ” I don’t have to see Mr Thompson?” “I do the hiring,” she announced somberly and then added “and the firing.”

Well before 8 on Monday morning, I reported to the new job and Tasha took me in hand. I soon learned how well she knew her job and the extent to which she ran the office. The girls in the steno pool deferred to her. No one even mentioned Mr Thompson. Tasha turned out to be a intense person who lived for her work, expected ever one else to do the same.

My job was demanding, but so interesting that I enjoyed it, found myself taking a full briefcase home every weekend. By the end of the first month, I seemed to have passed probation and my paycheck took a big jump. It was everything I had hoped it would be, but one small cloud appeared: Tasha showed signs of being a stickler for punctuality. I was putting in plenty of hours after work and on weekends, did not have a time card like the girls in the steno pool. There was no reason for me to show up right on the dot, especially on Monday mornings. It led to some brisk conversations with Tasha. “You’re late again Kenny.” “So I am, Tasha. I spent most of yesterday on this stuff in my briefcase.”

“That doesn’t make any difference. You’re supposed to get here on time. Everyone else does. Even the boss.” “I know you do.” “I didn’t mean me. I meant the big boss.” “He must hide pretty well. I’ve never met him.” Tasha’s face got an odd look at that, but she dropped the subject, that day anyway. The next Monday it started over again. I realized we were heading for a showdown and thought I might approach Mr Thompson myself, ask him to get this quarrelsome female off my back. I knew my work was excellent. I’d had spectacular raises to acknowledge it. There was no way he would fail to back me up. But it was Tasha who initiated a visit to the boss.

The following Monday, she became quite angry during the usual exchange. Some of the stenos were listening and it must have bothered her to have her authority challenged. Anyway, she finally said, “We’ll go into the Boss’ office and straighten this out. Come along.” I did not need urging. Tasha led the way to the very back corner of the big suite. A handsome black girl guarded an ornate door, which had a sign Thompson and Co.’ Apparently, we were expected. She waved us in without stopping her busy typing. Tasha in the lead, we entered an immense office, and my mouth dropped open. A mature beautiful lady sat behind the big desk. She was on the telephone, smiled and waved us to chairs. After a brief conversation, she put the phone down and said, “Finally, I meet the new man who has done such a wonderful job.”

While I was digesting the compliment, Tasha turned right in, “Lady Jacqueline, Kenny and I are having a disagreement as to what time he gets to work.” I said nothing, I was tongue tied. Such a lovely, self possessed woman running an immense business like this. She came out from behind her big desk, sat down, crossed her shapely legs and said, “What about it Kenny?” I found my tongue. “I work weekends, Lady Jacqueline. I didn’t think I had to come in on time every morning.” “Tasha has been telling me you come in on time very infrequently.” “I guess that’s true.” “Yes it is,” Tasha put in. “Well, I agree with you Kenny. You shouldn’t have to , but you should have to do what Tasha tells you to.” “I do, except for that one thing.” “And he argues with me in front of all the girls,” Tasha complained.

“Is it such a hardship for you to set a good example Kenny?” the boss smilingly asked. “No, I guess not.” “Not undermine Tasha’s authority?” “I suppose not.” “Then that’s settled?” “Yes, Ma’am”, from me “Yes, Lady Jacqueline, “from Tasha.

I’d lost that one, but the job was too good to lose also. I dragged my bones to the office on time for some weeks, was rewarded by seeing that Lady Jacqueline actually did arrive before anyone else. She always had a kind word for me, was generous with praise for all my work, but the time came that I rebelled. Damn, if I was going to work all weekend, show up Monday morning like one of the stenos. Tasha reproached me naturally, mildly the first time, increasingly as she saw that it was to be a pattern. One Friday she said, “Time for you and I to visit Lady Jacqueline again. She’ll be late today. Can you stay a few minutes after 5 or do you have pressing business elsewhere?” If that sarcastic note meant she thought I was afraid, she was wrong. I instantly agreed to wait until we could see the boss together. It was after five and everybody else had left before the visit. Tasha became quite pleasant while we were waiting. Surprisingly so, when the girls were out of earshot, she was very human. So much so that I impulsively suggested, “Why don’t you and I have dinner together after we see Lady Jacqueline?” She smiled at that. “Ask me afterwards if you still want to.” This time there wasn’t the big smile when we entered the private office. Lady Jacqueline stayed behind her desk opened the conversation herself. “You are having trouble doing as you are told, Kenny?” “I don’t see why I have to be prompt.” “One good reason, Tasha tells you to.” “I don’t think that’s such a good reason.” “No business runs without discipline, Kenny, any more than the army does. Tasha minds me; you must mind her. I have to be strict about that or we’ll all be out of a job.” Mrs Thompson’s voice was that of a mother patiently explaining to a child why he must mind Mama.

“You are a valuable asset here. You know that, Tasha would have fired you long ago otherwise.” “Yes Ma’am, You’ve seen that I was rewarded.” “Now I have to reprimand you. You can be thankful not to be told to pick up your check and leave.” “Yes Mama, I’m ready to listen.” “You listened last time we talked about this but it didn’t do much good. Another scolding is not what you need.” “Yes Ma’am.” I assumed I was going to be required to apologize to Tasha. Maybe in front of the whole office? “I have my own way of handling insubordination.” “What is that Lady Jacqueline?” “A sound spanking!” “A spanking.. Is that what you do?” “That’s exactly what I do. You have your choice between a sore toddy-side and looking for a new job.” I was stunned. “Who is going to spank me? Tasha?” “I will today, but then I will tell Tasha to bring you here and tend to you herself if there is anymore trouble from you. What is your decision?” She opened her desk drawer, pulled out a big ruler, walked around and leaned against the front of the desk, idly smacking the ruler on a shapely thigh. It was not a difficult decision. I’d never find another job as interesting and rewarding as this one. “If you think I need a spanking, I’ll take it Lady Jacqueline.” “Very well, take your pants down.” “Take my pants down? Bare skin? In front of you and Tasha?” “Of course, did you think I was going to spank your trousers?” “Can’t Tasha leave at least, Lady Jacqueline?” “No. Tasha stays. I have a feeling she will be reddening your bottom herself often enough.” “Yes Ma’am.” In horrible embarrassment, I fumbled pants and shorts to the floor, looked at Lady Jacqueline for instructions. Out of the corner of my eye I could see Tasha’s expression. She’d known what was going to happen. No wonder she smiled at the dinner invitation. If Mrs Thompson’s spankings were anything like my mother’s, I’d have no interest in sitting afterwards. Tasha was interestedly inspecting my nakedness. I would be glad when Lady Jacqueline took me behind her desk to put me across her knee. As calmly as if spanking a naked bottom was every day routine for her, Lady Jacqueline turned around and began clearing off her blotter. “Bend over my desk, Kenny,” she said. “Reach out and take hold of the far edge.” She had put the ruler down. I tried an appeal “Lady Jacqueline, couldn’t you do it with you hand just this one time? I … I… didn’t know how strict you are.” “No better time for you to learn, Kenny. You will find my ruler quite persuasive. Unless you are thinking of other employment?” “No Ma’am, I’ll mind.” I bent over the big desk, took a firm hold of the edge. Lady Jacqueline addressed Tasha. “Move your chair over here, Tash, so you can see if I do a good job.”

My head was on the blotter but I heard a chair being moved, then heard and felt Tasha lift my shirt tails off the target area before sitting down. Lady Jacqueline was talking to me again. “Kenny, I will insist that you submit willingly and completely. If you so much as let go of the desk before I say you may, your career here is over.” “Yes Ma’am.. Ouch!” The first crack of the ruler felt red hot. Before the sting subsided there was another, and another. I greeted each with surprised OWS, getting louder with each smack. Lady Jacqueline said nothing, just continued to pepper my poor ass. I was soon wailing, begging for her to stop, swearing I would never be late again. I resolved to get to the office an hour early every day, told her so. I never let go of the desk, but my ass waved in a fruitless effort to avoid the next stinging crack. Lady Jacqueline only moved closer, held me tightly against her body, dispassionately continued the spanking.

“That’s over,” the disciplinarian said, dropping the ruler on her desk. “You may stand and pull your clothes back up.” I did not trust my voice to reply, obeyed without a word. “Still want to take me to a sit down supper?” Tasha asked in a too innocent voice. “Tasha!” came a warning. “You’ve been across this desk often enough yourself. Do you need another lesson?” “No Lady Jacqueline. I’m sorry, I wasn’t trying to be nasty.” The thought of Lady Jacqueline spanking that pert bottom made me feel better. With bravado I said, “the invitation still goes. But how about a stand up meal?” “I’d love it.” “So would I,” chimed in Lady Jacqueline. “Am I invited too?” “Certainly Ma’am.” “At least you didn’t say, certainly Mama’. I think we are well enough acquainted now that you better call me Catherine.” “An honor to have your company, Catherine. Yours too Tasha.” “We are going to forget all about this little incident now, Kenny,” Catherine said. “But first I must warn you that it will happen again any time you need it. Tasha you are instructed to spank this employee any time you see fit.” “Yes Ma’am.” It pleased me that Tasha had not been invited to use the familiar Catherine. As I learned from my mother long ago, a spanking is a powerful influence to change behavior. I appeared at the office every morning promptly at 9, surprised myself by finding that I didn’t mind it, and that there was less work to take home, when I got busy early in the morning. Tasha had no more reason to complain of tardiness, but that did not mean she was any less my boss. I found that out the day we disagreed on a layout and I said I would not do it the way she wanted it. She stopped arguing immediately. I thought I had won the point, but then, “I want you to stay after 5 tonight.” “What for?” “We are going to use Mrs Thompson’s office after she leaves.” That was cryptic. Did she mean use the big couch in there? I’d like that. Tasha and I had been out on several dates, but so far my suggestions that we find a bed somewhere had been turned down flat. It must be she was going to change my mind on that couch. My excitement mounted as the girls packed up their typewriters and left one by one. Finally, Catherine left, took note of two employees staying behind, tactfully and said nothing. As soon as the door closed on her, Tasha carefully locked it, turned to me. “Go back to Mrs Thompsons office and take yoru pants down.” “Tasha, you are going to spank me.” “I most certainly am. Remember what Lady Jacqueline said?” “Honey, please.” “Never mind the sweet talk. Get back there and do what you’re told. Or would you rather Lady Jacqueline used her ruler tommorow?” “I’ll go Tasha.” Bare in the luxurious office, I wished Tasha would come in and get it over with. Instead she seemed to be deliberately keeping me waiting. When she arrived, I found out why. She had changed out of the office slacks and now was wearing a frilly white blouse, short skirt, dark brown nylons and heels. Compliments never do any harm. “You look lovely, Tasha.” “Thank you, I have a date tonight. Go out and bring me one of the straight chairs. There’s nobody there, no one will see you.” When I shuffled back Tasha told me to put the chair in the middle of the room and sat upon it. “I spank naughty boys across my knee,” she said. “Get over here.”

As I approached, she turned the skirt up til it was well over stocking tops. I lay face down on partially bare thighs. Tasha was not silent during the spanking, as our boss had been. “When I tell you to do something, you DO it, do you hear?” This was to the tune of stinging hard slaps and I naturally answered “Yes I do. I’ll mind. Ouch.” “I can’t make the girls obey unless you do.” More spanks, more sweet agreement from me. “If you think I won’t spank you in front of all the girls you are mistaken. The next time you defy me, I’ll take your pants down and put you over my knees right out in the office.” That prospect kept me silent. “Do you hear me? Do you think I won’t ?” A flurry of spanks punctuated that question. “Ouch. No Ma’am. I know you will, I hear you, Ouch. Please Tasha, I won’t ever do that again.” “You better not.” A dozen spanks. “Is this teaching you anything?” “Ow, ow, yes it is. I’ll be good.” “Hold still. Let me make it sink in.”

About two dozed smacks concluded the lesson. As I was dressing, with Tasha sitting there watching, I tried to make a feeble joke. “If you didn’t have a date. I’d ask you to drive me home. I won’t be able to sit in my car.” “My date won’t interfere with that.” “How comes?” “The date is with you. I’m going to take you home and make you dinner.” Flabbergasted, unable to understand women, I thankfully accepted. We left my car in the lot and Tasha drove us in her little Toyota. At her apartment, the first thing she said was, “Pants down again.” “Tasha, are you going to spank me again?” ” Just do what I say. Haven’t you learned that yet? Go in my bedroom and lie down on the bed. Bare bottom.” Sure there was to be a chapter two, and most likely with her hairbrush. I resignedly trotted off, partially undressed and flopped face down on the clean bed. She wouldn’t have to tell me to turn over. Besides, I did not want a certain area to bear weight. Tasha came in, carrying a jar. She opened it and applied cold cream to my sore bottom. It stopped burning at once. I thanked her of course, and she said, “I don’t like to punish you, Kenny, but I must when you don’t mind. Do you understand that?” “Yes, I guess so. If you don’t Lady Jacqueline will.” “Would you rather it was me?” The cold cream was being applied to some erotic places now. “I guess I like anything you do,Tasha.” “Like this?” “Yes! Just like that.” My car stood in the office parking lot all night and I went to work in the same garments I had worn the day before. One of Tasha’s little razors had done a half way decent job on my beard, but Lady Jacqueline was not born yesterday. “Your car accumulated a lot of dust since you arrived this morning, Kenny,” she said with a twinkle in her eye. “How could you see through that windshield?” I gave her a sheepish look, but noticed that Tasha was cool as a cucumber.

Things went better with my straw boss after that night. Either she was more lenient with me, or more likely I had decided to obey her. She still made her pressence known with me, as with the girls, but I followed the stenos’ example, did what she told me to do. We still dated but oddly enough, were back on the no sex routine which had existed prior to the spanking. I was even begining to think I better offend her, for a repeat of that entire evening, when thunderclouds gathered in Catherine’s office. I made an error. It was not a little one. Not something which Tasha should have seen. Catherine herself came out of her office bearing the offending paper and pointed it out to me. I was chagrined of course, sincerely apologized and promissed it would not happen again. “I’m sure it won’t,” she said, “Remain here at your desk after the others leave.” I knew what that meant. There was no mistaking the indignant heave of buttocks as she left my desk. Somebody was going to get a spanking and if it wasn’t me, why was my bottom tingling? Tasha was no help.

“You’re going to get it, ” she said when I told her. “Want me to stay?” The way Lady Jacqueline sounded, you better no be near her.” In the empty office after everyone, even Tasha had left, I heard urgent heels approaching and Catherine appeared wearing a stern look, ruler in hand. “Did you lock the door? ” “No Ma’am” “Doesn’t matter to me. I’m expecting two people. If you want them to see you get a licking, it is fine with me.” “I’ll do it now.” “No. Take your pants down and bend over your desk. This won’t take long.” I obediently stripped, was in the right position, when the door opened, a sweet soprano said, “You’re busy Catherine. We’ll come back later.” “No, come in, lock the door, come over here.” Two sets of heels approached my desk. Catherine put a firm hand on my back to hold me down, then made formal introductions. “This is my right hand man, girls. His name is Kenny. I couldn’t get along without him, but he does get careless and has to have his toddyside warmed occassionally. Kenny meet Annabel and Phoebe. I mumbled, “Pleased to meet you,” and kept my burning face turned to the desk. “Want us to help you?” came a girlish voice. “You know how to spank, Phoebe? I thought all you knew was how to be spanked!” I should know that. I might like to try the other role.” “Spank Anabel. She’s probably been naughty with Ingrid again.” “You stop egging her on, Catherine. She’ll do it.” “We’ll talk about it at bedtime.” During this interchange, I seemed to be forgotten except for Catherine’s hand on my back, but then she turned to me and began the lesson. Her illustration of how to reprimand carelessness should have been one her friends mever forgot. Certainly, I never would. The ruler landed, crack, smack, dozens of times. I started to cry, only to have her mercilessly continue the tattoo. The witnesses were forgotten. All I could think of was the terrible burning. I remembered Catherine’s stern warning when she spanked me before: If you resist, your career here is over.’ I concentrated on staying where I was, toddyside exposed to both guests and ruler. When the lesson was finished, I stood, not concerned about exposure, and danced about the room. “Going to be careless again, Kenny?” Catherine asked sweetly. “No Ma’am. I am not.” “Good. Your pay envelope Friday will comfort you.” When I pulled my trousers back up over a flaming bottom, and Lady Jacqueline and friends retired to her office, I left, badly wanting to be petted. As if she had known how I would feel, Tasha was waiting at the bottom of the elevator. “Come home with me ,” she said. “Mama will comfort you.”

The End

Ready to start your training?

Submit your application today!

Thank You for accepting my application and allowing me the privilege of entering the interior of Your site. It has indeed had a profound effect on my psyche. i view myself as transgendered, and i have been progressing along the… Read more “jamie”