MISTRESS ANNE and Jill (Part I)©2001 - Fiction Submitted by: John C
Jill glanced at the clock and gave a small, surprised gasp. It seemed that "she" had just gotten home and put down her briefcase, stealing a few moments to shed the day and unwind a bit before starting dinner. At least a half hour had passed, and her lover was due to come home any moment. Jill smiled to herself, and felt a stirring below her belly button, as she knew tonight was one of those special nights, with romance one of the chief ingredients.
The next few moments were a flurry of quick, decisive movements...uncorking the wine and setting it to breathe; grabbing a casserole out of the fridge and pushing it into the microwave; arranging some flatbreads in a basket and setting the table.
While the casserole heated, Jill carefully removed her pant suit, and quickly changed into something more feminine to await her lover. White lace bra and g-string panties accentuated her womanly form, though nothing was hidden from view. A lacy garter belt fastened the old fashioned stockings that she slid over her legs. A simple, low-cut satin lycra mini dress that just covered the tops of the stockings when she stood to check her image in the mirror finished the look. Sexy, but not tarty. Someone will be sooo pleased! A quick spritz of a favorite scent, a quick glance around, and all was in order....
As Jill prepared, she was acutely aware of the "feel" of the stockings as they touched lightly against each other, the silky sense of the smooth and shiny lycra as her hands brushed against it, the feel of the high stiletto heels and how they tipped her slightly forward, revealing a hint of thong satin panty under the mini dress as it pushed her ass into a prone and sexually accessible posture.
Jill knew that soon Mistress would be home, and she would serve Mistress, relax her, cater to her, and present herself to Mistress for her pleasure later that night, Jill knew that the silky dress would be the "wrapping" for Mistress's favorite presents: Jill's body for her use and pleasure, Jill's tongue for her orgasms, the look in Jill's eyes as she kneeled before Mistress, tied, ballgagged, having to watch Mistress pleasure and tease her pussy just inches from Jill's hungry mouth, to later be locked in an embrace as their stockings and satin rubbed against each others, as Mistress mounted Jill to receive the oral worship she so loved....
All was ready, and Jill could hear Mistress approaching, climbing the long 4-flight journey to the apartment. The wine was poured, the soft sensual music was on.....One quick check in the mirror to make sure the wig and make up was good and..
The lipstick... The lips were all wrong! Mistress spent hours teaching Jill how to properly prepare lipstick for a slut's mouth, thick and red lips, pencil lining the outside to make the lips full and ready to suck Mistress's strap on dick or lick a pussy- and the lines were NOT straight.....
Jill thought of running to the bathroom before Mistress was..........
The door opened......
"Honey...I'm home!" she called as she fumbled with packages at the door.
Wait a moment... why was she fumbling? Where was her mate to help her with her pocketbook, shoes and coat?
"Are you home?" She was a bit alarmed, as Jill got out of work a full hour and a half before she did, and worked close enough to the duplex apartment they shared to walk home.
"I'll be right there" was the muffled reply from the bathroom.
"Are you OK? Are you sick, darling?" Concern crossed Anne's brow, as the household ran on very strict rules. Ritual and time to interact together cemented a lovely relationship that was entering it's second year. The door greeting ritual was one that Anne particularly looked forward to, as it allowed the two to show their devotion to each other in a very basic way, and set the tone for the rest of the evening. Tossing the flowers that she had bought her "wife" for their anniversary, Anne rushed to the bathroom and opened the door.
"Ohhhhh...." Jill stood there, pale and trembling a bit....totally lovely except for the messy smear of lipstick across her mouth and cheek...she clutched a wadded tissue in one hand.
"What is the meaning of this, Jill?"
Well, Mistress, I um..Didn't..
"YOU ARE HESITATING! You didn't meet me at the door DRESSED in your dress and heels? WELL?"
"Well Mistress, I was fixing my lipstick to please you. "
"Uh HUH" she said doubtfully.. "Well what are we going to do about this. I did have a night of "stocking-rubbing" and release.. and you KNOW what will NOT COME OFF TONIGHT! Instead I think it will be a night of being tied up and ballgagged, used - and then you can watch me pleasure MYSELF. maybe if you are good I will let you keep my dildo wet for me in between plunges.."
"But you do look pretty in that shiny minidress and stockings and heels. I may use you tonight with my strap-on. You know what a thrill that is for me, love the power, love the feeling>" Jill forced a smile, then just lowered her head.
With the words ringing in Jill's ears about the look of the mini dress, she thought how they first met. It was a busy Halloween night and the party was full of celebrants! Jason's interest in sexy woman's clothes was always there, having grown up with all girls in his family, but his interest was always in women wearing those clothes, not him. But on a dare and with the help of a professional make up artist friend of his, he dressed in a long black wig with bangs, a corset, and mini dress and heels for the party. When he did, two things happened: He looked great as a woman, most passable and sexy, and He liked the feel, it was most erotic.
Jason had been involved in the BDSM scene for years, and was a submissive. But never did he couple woman's clothes with being submissive. Most of his BDSM play encounters dealt with him naked, and the DOMMES dressed in leather, latex, stiletto boots, and other standard DOMME outfits. When Jason met Anne at the Halloween party, there was an immediate chemistry. Anne, with her long black Raven Hair and sensual lips, caught his eye. Her outfit, A BLACK CORSET, flairy satin skirt, high boots, and a riding crop in hand caught Jason (JILL's) eye like a magnet to steel.
Upon first glance n the dark room across the floor, Anne thought Jason WAS Jill! Jill's gold lame mini dress, platform heels, and stockings caught Anne's eye, and the kitten collar and dangling chain from Jill's neck REALLY caught her eye. "AAHH, a Twinkie" thought Anne. She walked up to Jill, grabbed the dangling leash, and said "Hello". Upon getting that close and hearing Jill's (Jason's) whispering voice, Anne realized that Jill was a MALE dressed as a woman, and looked HOT! "THIS IS GOOD!", Anne thought, "This is "VERY VERY GOOD". Anne was not a lesbian, and preferred men, however, she did have a strong bi-sexual interest, and often thought how great it would be to have a strong and handsome man at her side by day, or out at night, and have him "transform" into a sexy silky "Twinkie" at home at night for feminine sexual pleasures, satin against satin, stockings against stockings, sweet "perfume and lipstick" nights.
After some brief small talk, the "white-heat" was so hot that Anne and "Jill" left the party and headed for Anne's apartment, for some wine and talk. What ensued was a night of sexual bliss, light BDSM which would later grow strong and intense over time, and the realization for both of them that they were two very unique people with a very exotic and singular desire for this unusual "special pleasure" . This was the beginning of their relationship.
Anne's demands were simple in concept, Jason was to be her man, dressed as a man at all times in public (except for BDSM parties etc...) and would behave as such. BUT, at night after he returned from work and had his evening shower, Jill must emerge from the bathroom, freshly shaved, perfumed, and lubed for pleasure. Both Jason and Jill would be sub to Anne at all times, though usually couched in public. Jill was Mistress Anne's property, her lover, her slave, her sexual toy, and her "Twinkie". Jill's personality must transform along with the clothes, so Jill acted and spoke feminine, and please the Mistress in this fashion. This was actually quite easy for Jason, because sexy silky clothes and high heels had that effect on him immediately anyway!
An additional problem was solved when Anne began to enforce "CHASTITY" on Jason. Jason was an ardent masturbator, and had been for his whole life. He was ordered to stop, but a verbal order cannot change many years of habit. SO Anne used a small black tube, secured by a small gold padlock to secure Jason's penis by day. At night, after greeting Mistress at the door as "JILL, the device was removed so the Mistress could have full access to it if she chose. It also made an unsightly bulge in a tight mini skirt, so it was removed when Jason became Jill. For Jason, the chastity device was most effective, but also most distressing, as ever sexual thought, image, view, and woman he passed on the street caused an erection, one that could not be completed due to the tube, but always reminded him of whom the penis truly belonged. It also gave him tremendous incentive to hurry home, shower, shave his body, and get pretty for Mistress Anne, as that would mean the tube would be removed at the front door for the evening. So when she said "YOU KNOW what will not come off tonight" she referred to the tube. It was especially difficult for Jason to have to wear the tube as Jill, because the feel of being dressed as a woman and constant brushing of the sexy spandex or satin against the tube made the penis constantly in a state of erection, or as much as could be inside this device.
And after a long day of work, having to completely shave, spend time preparing make-up, lipstick, dawning lingerie, dress or mini skirt, heels stockings, and then preparing dinner for Mistress was difficult. Knowing that the tube would be removed when Mistress entered the house usually made it all worth while. The Mistress also knew the importance of making Jason's cock cum several times a week to prevent medical conditions and to keep it in good working order when she DID want it, but Jill came only on Mistress's terms and conditions. And maybe a few times a week, not two or three times a day, as was Jason's masturbatory habit. Mistress especially loved sex with Jill dressed sexy, slutty, or just plain hot, and it was like two women with a shared dildo in each other simultaneously. It was magic for Anne and Jill! But there would be no release and no cumming tonight, at least not for Jill!
Anne took Jill to the mirror and showed her the smeared lipstick.
"AND WHAT is THIS?" she demanded, pointing to Jill's lips.
Well Mistress..I um.
"YES YES .."
Mistress Anne told Jill to kneel, then began to fix her lips.
"I have taught you and taught you. And still you get it wrong! It is important to me that you look pretty when I get home after a stressful day. I need my girl to look sexy and inviting, especially the lips!"
"Yes Mistress" Jill whispered meekly.
And you never know when I am going to come home and want you immediately, or maybe bring home a friend for you to please. I cannot have you looking like a $2 whore!"
After fixing Jill's lips, Anne helped Jill stand. Her 5" stiletto platform heels were still a bit difficult for Jill, but since Mistress Anne kept her in heels and skirts at all times at home, Jill was getting a lot more use to it.
Upon standing erectly, Anne walked Jill over to the couch and pushed her over, so her body was bent over the arm of the couch. Jill knew immediately what this meant. Instinctually, Jill bend over and spread her legs. Mistress Anne had trained Jill to be taken at any time anywhere, and Jill was trained to bend over, arch and present, and spread her legs. Mistress Anne had taken one of her many strap-on dildos out, and had slipped into it after having fixed Jill's lipstick. A small tube of a sweet-flavored lube was in her hand, and she administered it to Jill's anus immediately. Within a second, Mistress Anne was deep into Jill, moving in and out, slow at first, then more. She had taught Jill how to relax her body, how to arch her back to present herself for use by Mistress Anne without hesitation, how to enjoy the fullness of a big cock inside her, how to orgasm like a woman, not buy erection and ejaculation, but by feeling the deep womanly feelings inside when entered.
Jill shuddered as she was used, and Mistress Anne leaned over Jill as she moved, using her fingers to rub Jill's satin-covered breasts. She knew this was Jill's most sensitive area, and Mistress Anne's constant rubbing and stimulation of Jill's nipples over time and made Jill's breasts grow and become very pert, like that of a pre-teenage girl's. Mistress Anne also had the strap-on positioned to stimulate herself, so her orgasm was present as well.
After using Jill for her pleasure, she removed her dildo, walked over to an oak bureau, (which was full of sex toys) and took out fur-lined wrist cuffs, and a ball gag.
"Now that your lips are finally fixed right, I need to remind you of one of many reasons why I keep them that way." With that, Mistress Anne took Jill's wrists, put the cuffs on, and locked the cuffs behind Jill's back. Jill loved the feel of the satin skirt on her ass as her hands rubbed against them while cuffed. Mistress Anne adeptly placed the ball gag in Jill's mouth.
"Nothing prettier than slut-red lipsticked lips surrounding a tight ball gag, don't you agree Jill. Jill could not speak, but nodded her head in the affirmative. Actually Jill was glad it was the ball gag and not the latex penis gag, which was much more restrictive, gagging, and made Jill so helpless and vulnerable. "Kneel" Mistress Anne said, leading Jill to a large velvet pillow placed before a large upholstered living room chair. The chair was affectionately called "THE THRONE", and had been modified with o-rings and other secret bondage restraints.
Jill kneeled on the pillow. Mistress Anne sat on the throne, placed a collar on Jill's neck, and positioned Jill in-between Mistress Anne's legs under the mini skirt she was wearing. Mistress Anne had on one of her sexy business suits with a low cut satin "wrap" blouse, one of Jill's favorite outfits on Anne. Mistress Anne attached a leash, then another, to Jill's collar.
Then she pulled the ends through the o-ring eyebolts behind the legs of the chair. It forced Jill's head in-between Mistress Anne's legs. It was then that Jill noticed that Mistress Anne had removed her panties, and her pussy was moist and wet. The leashes forced Jill to be within an inch of Mistress Anne's pussy. Mistress Anne picked up a sexy magazine, and proceeded to leisurely read it while Jill knelt in-between her legs, her face in Mistress Anne's sweet pussy, but unable to do anything but see it, smell it, and wish for it.
Jill knelt tied for what seemed like ages while Mistress Anne finished reading her magazine. Then Mistress Anne removed Jill's ball gag, and said "OK Sweetie, it is dinner time for you", and with that forced Jill's mouth onto her wet pussy. Jill began to work on Mistress Anne's pussy they way she had been trained to, and Mistress Anne's reaction was that of delight and pleasure. It wasn't long before Mistress Anne let out a loud moan of pleasure and her body quivered in orgasm after orgasm.
Mistress Anne had spent hours teaching Jill how to properly lick her pussy, as well as how to make love like a woman, how to touch and caress like a woman, and how to dress, act and feel like a woman. And she did this NOT just by words, but by actions; by spending hours with Jill in bed dressed in lingerie, hours of passion, touching, licking, heated passion. Hours of being sexually physical as "woman to woman", BUT also hours of necessary strict discipline, reprogramming, bondage, and forced feminization. The whole program had a total effect or turning an average male lover into a superb female love-slave. And Anne knew there was no going back to the former after this experience.
The evening progressed to a pleasant dinner with her slavegirl, Jill serving Mistress Anne, awaiting the invitation to dine with her, and the light conversation and some girl-talk about shopping and new sexy things Jill will be made to wear in the future. Upon completion of the meal, Jill went into the bedroom to see what Mistress Anne had laid out for her, as was the custom for the evening. Mistress Anne had picked out a beautiful satin corset, with a design that made it go under the breast, exposing breast and nipples. It had a tight, firm sculpting underwire which gave Jill the look of cleavage and breasts, and left them exposed for the Mistress's pleasure and access. Most of Jill's bras were also designed with firm underwire in the satin to create the look of female breasts and cleavage. There were matching while lace stockings and stiletto heels lying on the bed, and the corset had white garter straps attached. Jill dressed quickly, then returned to present herself to the Mistress.
Mistress Anne bound her wrists behind Jill, had her kneel before her, and lightly played with Jill's nipples again for some time, making them pert and full. Jill's "member" strained against the chastity tube that contained it, as it held it in, as no unauthorized orgasms OR erections were allowed. After what seemed like an eternity to Jill, Mistress Anne helped Jill up, unbound her wrists, and walked her into the bedroom. On the bed, attached to the Brass headboard, was a long white satin scarf. Jill laid on the bed and instinctively crossed her wrists. Mistress Anne tied Jill's wrists in front of her body. Jill laid on her back and lifted her tied wrists over her head. The satin scarf was then tightened to hold Jill's arms.
Mistress Anne left briefly to dress herself in a beautiful black satin corset and stockings. Upon returning to the room, she produced a small key that was on a chain around her neck. "Well you have been a pretty good slut" she mused. With that, she released the chastity tube holding Jill's "member" tightly in place. Without talk, Mistress Anne mounted Jill. She did not mount Jill astride sitting up, but rather laid her body on top of Jill's, kissing her as she did. With forceful rhythm, Mistress Anne began to ride Jill in a "missionary" type position, so that their bodies touched each other, satin against satin, stockings against stockings, breasts against breasts. She kissed Jill forcefully as she rode her and whispered for Jill to cum. Within a short time, Jill came violently and vocally, and released a surge of warm fluid deep within Mistress Anne.
Mistress Anne slowed her rhythm, enjoying the warm inner feeling, then deftly reached down and squeezed her lower lips. Quickly she moved up Jill's body so that she was now sitting up, astride Jill's still lipsticked mouth. Lowering herself down and releasing her vaginal lips, she put herself to Jill's open mouth. Jill licked her Mistress and almost immediately Anne exploded in waves of rippling orgasms. One after another, as Jill caressed the Mistress's pussy and tasted her sweet nectar mixed with the salty warm fluid. Again Anne writhed in pleasure, and when finished, fell to the bed exhausted. She cuddled Jill for some time, then released her arms from the satin scarf. Jill and Mistress Anne cuddled together and both fell asleep quickly from both exhaustion and after-glow.
The morning arrived early, and Jill was up and out of bed quickly. Coffee was brewing, and Anne was still asleep. Jill went into the bathroom, applied a powerful cream make-up remover, and took a shower. From the bathroom, out walked Jason, with no trace of Jill or her make-up. His hair combed and his face freshly shaved.
He slipped quietly back on the bed, and awoke Anne with the warmest and most gently tongue against her sweet pussy. She stirred and moaned in pleasure. "Time to get up" he said softly as he continued to pleasure her. She slowly rose to greet the morning. Her coffee had been prepared, and she slowly wandered over to take a morning sip and smell it's inviting aroma. Soon thereafter, Jason walked back into the room wearing a beautiful charcoal-gray Italian double-breasted suit and hand-painted silk tie which made her moan with approval. He presented himself to Anne, and she re-attached the black chastity tube to his penis, locking it firmly with the small golden padlock, and returning the key chain to her neck with a wicked smile.
"I have to run dear, early meetings". She looked at him and knew she loved him. He kissed Anne passionately on the lips, which made her knees weak. Jill will see you tonight, he whispered.
He left quickly with business on his mind. As the apartment door closed behind him, Anne leaned back, coffee cup in hand, smiled, and sighed "WHAT A MAN!!!"
Page last updated 01-Dec-22 by: Altairboy@aol.com