Crystal's StorySite storysite.org
by: Miss Vicky
My name is Vicki, well that is not entirely correct, my name is actually Jim, but I now answer most of the time to this new name given me by my Mistress. I am writing this account explaining how this came to be at the behest of my Mistress. As I enter this into my computer, I am wearing a lacy pink baby doll nightie with matching panties. My Mistress is sitting beside me dictating what to write. Every now and then she strokes my panty covered cock to reward me for my efforts. With each stroke, my cock twitches inside its frilly prison and I gasp with involuntary pleasure. Her Cheshire cat smile tells me she knows just what sort of effect her fingers are having. Well enough of my relating what's happening at the moment, let me recount how I came to be placed in this humiliating position.
It was my vacation week and I was looking forward to a week of rest and relaxation. My live-in girlfriend Jackie, had to work so I had the house we had bought together to myself. The first morning of the week I kissed Jackie good-bye, and as soon as she left for work, I got up and started to get "Dressed". I went to the attic and brought down my favorite under things, dress and shoes. I am a bit larger than Jackie, otherwise I would wear her things. I took a quick shower and shaved my face as close as I could. After drying off, I slipped into a sheer mint green peignoir set and went to the bedroom to complete my transformation. I slipped off the nightie and put on a black lace merry-widow with matching black lace french cut panties. I had taken in the merry-widow and it pulled my waist in a good 4 or 6 inches, giving me quite a bit of a figure. My maleness was already starting to rise, so I paused a bit and tucked it under and pulled the tight panties up. I then slid on a pair of black stockings and attached them to the garters. Next I slipped a pair of breasts into the cups and took a good look in the mirror. I saw a very sexy lady looking back at me. (so much for fantasy!).
I sat down at Jackie's vanity and started to put on my makeup. I was in the middle of the lipstick when I heard the door open. I panicked.
"Honey I forgot my purse." I heard Jackie say as she headed to the bedroom.
Jackie does not know of my dressing. I have tried to tell her before, but I couldn't. I tried to hide but it was useless. She opened the door and saw me trying to cover myself up.
"What on earth are you wearing?" she stammered. I fumbled out a flimsy excuse that made no sense at all, when she said " I always thought you were hiding something, but I never thought it was this".
"Are you angry?" I asked her.
"Let me put it this way", she said "I don't know why you are wearing my clothes, but you had better have a better excuse than you were lonely!" "We will talk more when I get home, and I want my future husband, not this" she said sternly as she stormed out of the house.
All my plans and dreams seemed to be crushed all that day. I finished dressing, putting on a leather mini skirt and silk blouse, but my mind was on what Jackie said. That afternoon I changed back into my male clothes and prepared myself to face the music.
Jackie came home and after a good hour of cold war stares she asked me how long I had been wearing her clothes. "Well", I started " I have been wearing girls clothes off and on since I was 12 years old". "I am not gay, I just love the way I look in the clothes. I especially like the feel of silk and satin lingerie against my skin". Jackie asked me why didn't I tell her. I told her I have tried to many times. "Don't you remember Halloween last year when I suggested you dress as a pimp and I would be your `girl`?"
"Yes" she said, "come to think of it you did get into the role more than I expected you to." "And another thing", she said " where did you get those clothes, they weren't mine!?"
"Actually they're mine", I said " I have a collection of many different types of dresses and such".
"You mean the things you had on this morning are yours" She asked?
"Yes they are", I said. "I have some information you can read", I said " if you want more information about cross-dressing"
"Get it for me" She said "and after I read it we will talk again".
I got the information about dressing from my study. It included articles about cross-dressers, as well as some magazines on the subject. The next few days Jackie said very little about the subject, and I was not going to upset her by bringing it up. Then on Friday she called me and said she would be late coming home because she had to do some shopping. Later that night I was watching the tube and Jackie came in and made a bee line to the bedroom.
"Don't come in here", she said I want to show you something in a minute. I sat in the living room trying to figure out what she had.
She came into the living room a few minutes later wearing a tight black satin dress and 5" heels.
"You look great" I said.
"Not as good as you're going to look" she said as she grabbed my hand and led me into the bedroom. My maleness was hard as a rock as I watched her buns swish in the tight dress. Her garters were very visible under the material and that only made it better. When we got in the bedroom she told me to close my eyes. I closed them and she ordered me to strip, keeping my eyes closed. I asked her what the surprise was and she told me not to worry and do as I was told.
After I was naked I felt her putting some lotion on my legs. This will help your legs to look better she said. I knew what was going on, but I was to stunned to ask her why the change of heart!. After a few minutes she took me by the hand and led me to the shower.
"Hop in and wash off". she said " and meet me back in the bedroom.
I got into the shower and I saw the hair falling off my legs. After I finished the shower I dried off and went back into the bedroom. Jackie had some lingerie laid out on the bed.
"Put this on " she said as she handed me a frilly red merry widow.
I put the merry widow on and she told me to turn around. I turned around and she hooked it up the back. "Not a bad fit for a first try" she said as she hooked the last one. "Now for the panties", she said "but first we have to do something about that protrusion". My cock got even harder when she said that. "I want you to take care of it the way you would if I wasn't here!" she said. "And if you refuse I will tell all your friends about your "hobby".
Reluctantly I took my cock in my hand and started to masturbate. I was about half way to climaxing when she stopped me and said ,"you need something on your legs for this".
She gave me a pair of black seamed stockings with lace tops and 6" black pumps. "Put these on baby" she said with a sly look. I sat on the bed and slid the nylons up my legs. They felt so smooth on my now hair-less legs. I attached the garters to the lacy stocking tops and slipped into the shoes.
"Where did you get this stuff" I asked her.
"Be quiet and do as you're told" she reminded me.
"Now stand up and finish the job at hand so to speak" she said.
I took my raging member in my hand and in a minute of quick moves I shot half way across the room.
"Perfect" Jackie said " and just think it's all on film!"
"FILM" I shouted, "you filmed this"?
"Yes baby how else do you expect me to keep tabs on you." But don't worry, as long as you do as I ask, no one will ever see this tape." After a bit more protest, she had me put on the red lace panties and a red satin mini dress that barely covered the tops of my stockings when I stood up.
"Sit down and let me make you up" she said. While she was applying my foundation, she started to tell me what was going on. "I read the information you gave me and I realized you really enjoy wearing women's clothing. Judging by what I saw you wearing Monday and the articles I read I figured this was the look you loved the best." She finished the foundation and started on my eyes. "I went to one of the stores in the magazine you gave me to read, That's where I found this outfit you're wearing as well as my outfit. I decided that I would rather have you dress like this here instead of worrying that you would dress like this when you were away".
She finished my eyes with a bright shade of blue eye shadow and black mascara, then started on my lips with a shade of deep red lipstick. "The way I figure it" she continued, " is, if I have a boyfriend who dresses up like a woman, I might as well let him. In fact you look so good I might just keep you this way all the time".
When she was finished with the make up, she brought out a blonde shoulder length wig. "Lets put this on and see how you look Jim, I mean Vicky". I think you look more like a Vicky than a Jim right now. She put the wig on me and adjusted it and then helped me up and brought me to the mirror for a look.
I couldn't believe what I saw. If I was a woman, I would be chasing myself. I turned from side to side and I looked great.
"Vicky" Jackie said, "we forgot your breasts"
I looked and realized that the only "chest" was from the merry widow.
"Lets use yours" she said.
I went to the attic to get my falsies. When I returned, Jackie pulled my dress over my head and slipped the breasts into the cups. After I pulled the dress down, I took another look in the mirror. "There, that's much better" she said.
After admiring myself in the mirror I realized the camcorder was still recording this and I was going to ask Jackie to turn it off. Then I thought about it and said to myself "what the heck, it will make interesting viewing later". My thoughts were broken by Jackie's order to make dinner.
"What would you like love" I asked.
"I don't know, just surprise me. I'm going to chance into something more comfortable while you prepare our meal".
I went to the kitchen and started making a nice steak dinner. I was enjoying the newfound acceptance by Jackie.
"Dinners ready Honey" I called from the kitchen.
"I'll be right there" she answered. She came out in the white peignoir I had gotten her for her birthday. Her breasts made an interesting swell in the bodice. As she moved about the robe swirled around her, giving me a glimpse of her beautiful legs. She came over to me, gave me a hug, grabbed my buns and said "you look great honey" "What's for dinner"
"Steak and rice" I said. She squeezed my ass again and said great I'm starved let's eat." We sat down and ate.
"You know Vicky", she said "you have been working much too hard around here. I think it is time to get a maid".
"A maid" I asked?
"Yes, and I have just the outfit for her" she said with a sly look as she finished dinner. After dinner I was washing the dishes when Jackie came in the kitchen and started to stroke my leg, running her finger tips up to my crotch. "Lets go to bed Vicky", she said "the dishes can wait for the maid".
I didn't have to be asked twice. We retreated to the bedroom and I started to take off my dress when Jackie stopped me. "Leave it on Vicky"she said "it looks good"
I pulled the dress back down and stretched out on the bed. Jackie came over and started to caress my "breasts" like I do to her. It felt so good I almost felt like a real woman. She started to kiss me passionately, starting at my lips and continuing down past my breasts to the waist band of my panties. She stood for a moment to discard the robe of the peignoir set. She slowly started kissing me again from the neck down to my heels. When she got to my heels she re-positioned herself and started to nibble on my cock through the fabric of my panties. She pulled up the hem of her nightie and shoved her hips towards me until her panty covered pussy was staring me in the face. I didn't know what to do.
"Go ahead Vicky suck me" she moaned. I pulled the crotch of her satin panties to one side and took her clit in my mouth and went to town, lashing it with the tip of my tongue while I sucked it into my mouth. She ground her clit against my face while I did this, increasing the pressure. It took only a couple of minutes for her to reach a wild climax, bathing my face with her sweet juices.
When she had sufficiently recovered from her shattering orgasm, she told me to take off my panties and lay flat on my back. I did as she instructed and after placing a pillow under my butt, she had me extend my arms and legs as far apart as I could. She reached into the night stand and retrieved four padded leather cuffs. After fastening one to each of my wrists and ankles, she showed me the next surprise in store for me. Out of sight beneath the bedspread, she had fastened four eye-bolts with a length of sturdy rope attached. Before I could protest, she had the ropes attached to each of the cuffs, leaving me tied and helpless in a spread-eagled position. Once she was finished securing my body to the bed, she flipped the hem of the dress up, leaving my privates completely exposed and vulnerable to whatever she had in mind. I soon found out what sort of sweet torture she had in store for me.
"Since you have a fetish for panties, I'm going to try and overload your senses with the feel of soft, silky panties against your skin", she gloated. She bent at the waist and removed the panties she had worn while I brought her to climax. She pressed them against my nose, forcing me to inhale her scent. Just the smell of her hot pussy caused my cock to twitch with desire. Noticing this, she pulled the white panties over my head, positioning the crotch over my nose and mouth. Now every breath I took filled me with her essence. Not yet satisfied with my level of excitement, she took the red panties I had worn and using just her thumb and forefinger, dragged them over and around my cock and balls. It felt like a butterfly was stroking my cock. The softer the strokes, the more intense the pleasure. It took only a minute of this for my cock to begin to ooze pre-cum. Next, she cupped my balls and began to stroke my cock with her panty wrapped hand. I could feel the cum beginning to boil in my loins. The onset of my climax was only seconds away. She sensed this and stopped immediately. I was left hanging on the precipice. If my hands had been free, I would have finished what she had started myself. Of course, I could only lay there and squirm with unsatisfied lust.
When I had calmed down, she once again used the same technique to bring me right to the edge. By now I was moaning with desire, craving the release my body screamed for. At last taking pity, she straddled my waist and using one hand to hold my cock and the other to spread her pussy lips, she impaled herself on my cock.
I had never felt anything so good in my life. As her hungry pussy swallowed my cock, it felt as though it was being immersed in a vat of warm oil. Once it was all the way in, she began to raise and lower herself up and down until she was ready to join me in ecstasy. As her second climax hit, she ground herself against the base of my cock. Her vaginal muscles contracted around my cock, impelling me to orgasm. Spurt after spurt shot from my cock deep inside her as her pussy milked me dry. I thought I'd never stop cumming.
She collapsed on top of me and kissed me gently, "this is just the beginning of your new life my little sissy", she purred. "Now go to sleep, you have a big day ahead of you tomorrow". She left me bound to the bed with my new dress around my waist. After what seemed to be an eternity, I was able to drift off to sleep.
When I woke up I was no longer bound. Jackie was up and said from the kitchen, "good morning Vicky. your clothes are in the closet" I went to my closet and discovered that all my male clothing was gone. The only thing there was a short pink Maids uniform, and several boxes filled with some very frilly lingerie.
The uniform was the same one I put on lay-away at the TV shop in town. It even had the slip I filled out. I took off my clothes began dressing in the new lingerie.
First, came the pink merry-widow trimmed lavishly with black lace and ribbons. Even though it fastened up the front, it was a real struggle to get it closed. When I finally was finished, my waist was 6" smaller and I had the illusion of small breasts swelling above the cups of the built in padded bra. Next, I opened the new stockings. They were the sheerest you can buy, with seams up the back. After fastening the six garters hanging from the merry widow, I reached into the next box to discover a pair of pink panties.
They must have been custom made just for me. Across the front, embroidered in black was the message; "I AM Jackie's PANTY SLAVE". The back was adorned with rows and rows of delicate black lace ruffles. I pulled the panties up my legs and as they settled about my cock, I felt as though my masculinity, and with it my ability to resist, were gone. This was not the sort of thing a virile man would wear, rather these were the panties of Jackie's personal slave.
Next, I opened the last box to discover a short, very full black satin petticoat. I pulled it up around my waist and then slipped the maid's uniform over my head. I managed to zip it up without help and then went to the vanity to freshen my make up and brush my blonde wig into place. The final step was to slip into the black patent heels.
When I was satisfied with my appearance, I walked back to the closet to inspect myself in the full length mirror on the back of the door. The fullness of the petticoat pushed the hem of the uniform out and up, exposing the lacy garter straps and the tops of my stockings. The over-all impression was that of tramp with a capital "T". Rather than being ashamed or uncomfortable, I found that I loved the look and hurried down to show Jackie my new countenance.
She was seated at the kitchen table, dressed in her pale blue baby doll nightie. "Vicky, you are the epitome of a slutty tramp!, Jackie cooed. Come over here and let me inspect the job you did preparing yourself for your new position."
I went over to where she was sitting and stood there with my hands clasped in front of me awaiting her pleasure.
"Turn around slowly", she commanded, "I want to see every aspect of your costume".
I did as she instructed, pirouetting slowly. I felt her hands on my stocking clad legs, softly stroking them. As I finished the turn, her fingertips roamed higher under the petticoat, until they were tracing the lettering on the front of my new sissy pants.
"These words will define your new existence my pretty", she said. Her fingers continued to stoke my panty clad cock while she went on. "From now on, whenever you are home you will wear nothing but your frillies. Also, when you get ready to go to work, you will find the lingerie I have selected for you wear under your male clothes laid out in the bathroom. Your days of sneaking about and dressing only when you are alone are over. Henceforth, you will live in pretty panties, garter belts and stockings. Every day when you pull your panties up over your cock, it will serve as a reminder of your servitude to me. Every step you make at the office will cause your panties to caress your privates, stimulating you to distraction. This will also serve to ensure your fidelity. Dressed as you are, you will have to wait until you get home to me to get any sort of relief. I have seen the way the women in your office look at you. They would love nothing better than to get into your pants. I can only imagine what those hot little secretaries would think if they were to unzip your slacks expecting to see BVD's and find instead your cock trapped in the frilly panties I laid out for you that morning. I suppose they might even be a little jealous since your lingerie is bound to be much prettier than anything they have. As long as you behave, it will be our secret. Your co-workers will never know that under your Brooks Brothers suit there lives my fancy panty slave."
After giving my cock a final squeeze she continued, "Now that we have the rules defined, you may begin your service as my maid. I want you to first prepare my breakfast. I will leave the menu up to you. When you have served me, you will do the dishes left from last night while I eat. Only when the kitchen is spic and span may you have your breakfast. I am sure you are aware that the household help is seldom allowed to eat with their Mistress".
I set about my assigned tasks, preparing poached eggs, toast and coffee. I served my Mistress in the dining room and after making sure she had everything she needed, set about clearing the dishes from the previous night. By the time I had all the dishes and pots rinsed and in the dishwasher it was time to refill my Mistress's coffee and clear her plate. Just as I finished, I heard my Mistress call me from the living room.
I obeyed at once, finding her sprawled on the couch with her legs spread and her baby doll panties lying next to her on the couch.
"Seeing you in your new uniform has gotten me all wet and sticky. You may have the pleasure of cleaning my pussy. I want you to use your tongue of course, but so be sure you don't cheat, I think I'll restrain your hands."
With that, she put the cuffs on my wrists and secured them behind my back with a double ended spring clip. I went to my knees and she grabbed my head with both hands, guiding my mouth to her sopping pussy. I settled in to the task at hand with gusto. At this time nothing seemed more important than the complete obedience to and satisfaction of this enchanting creature. My tongue seemed to have a life of it's own, dancing back and forth across my Mistress's clit. When her climax hit, I drank greedily from the fountain of her femininity. I continued to lap at her pussy, cleaning every drop of her juices from her labia and pubic hair. As the tremors of orgasm subsided, I laid my head in her lap while she stroked my head, telling me what a good slave I was. This was heaven!! My fetish for cross dressing and Jackie's latent desire to dominate and sisify a man had combined to create the perfect relationship.
My new life was one of never ending surprises. Each morning I would jump out of the shower with my face and legs freshly shaved to find the lingerie my loving Mistress had laid out for me to wear under my suit. Her imagination and sense of style always assured that I was dressed in only the finest and frilliest of lingerie.
We had spent the remainder of my vacation shopping and building up my wardrobe of lacies. Of course when we went out, I was made to wear my panties and garter belt. My Mistress took great delight in my embarrassment when the sales girls would give me a knowing smile as I piled my selections on the counter to be rung up. One look at the two of us and the disparity in our sizes was all it took to let them know that the pretty things I was buying were for myself. Each time when we arrived home, I was ordered to give Mistress a fashion show, modeling the days purchases.
My favorites were the nighties and peignoir sets. The feeling of the slippery fabrics caressing my body from shoulders to ankles was delightful. My cock always responded in a most positive manner to this form of stimulation, growing to its fullest. If Mistress was in a good mood, she would wrap a pair of panties around it and stroke it until I came all over the lacy fabric.
If she was not in a good mood however, she would cuff my arms and legs to a chair and then tease me. Sometimes this would take the form of her stroking my panty trapped cock until I was just about to come. She always stopped before I made it over the top. This was usually followed by making me watch as she slipped her hand down inside her panties and masturbated herself to climax. The sight of her fingers slipping in and out of her creamy pussy combined with the scent of her juices drove me wild with desire. When she reached completion, she would take her soaked panties and place them over my head, leaving me there to contemplate my fate while she showered and changed into fresh lingerie. She knew I would be driven insane with lust by the feeling of her panties over my face and the aroma of her climax.
Mistress spent the entire two weeks of my vacation imprinting firmly on my mind just who was in control. I was at her beck and call 24 hours a day, expected to comply instantly with her requests. I cooked all the meals, cleaned the house until it sparkled, and attended to her while she took her bath. Of course I never wore any male clothes during this time. Mistress always dressed me in something frilly and feminine.
By the time my vacation was over, I was completely trained and under her spell. My days were filled with joy as I did her bidding and the nights were ones of sensuous delight as she taught me new ways to attend to her sexually.
No matter what form our sex play took, there was always one constant. I was never allowed to reach a climax unless I was restrained. Looking back now, I can see how cunning my Mistress really was. She taught me to associate being restrained with the ultimate pleasure of orgasm, leading me to crave being made vulnerable and helpless.
All too soon, the vacation was over and it was time for me to return to the mundane world of earning a living. I remember vividly getting ready for my first day back to the office.
I came out of the shower to find new lingerie laid out on the bed for me. It consisted of a matching camisole, garter belt and pair of panties, all in black with lavish red lace trim. Completing the set was a pair of red, sheer, seamed stockings. I fastened the garter belt about my waist and pulled the stockings up my legs. My penis instantly grew to its fullest. The sight of my turgid cock framed by the lacy garter straps almost made me come then and there. I slipped the camisole over my head, relishing the sensuous caress of the slippery fabric as it cascaded down over my nipples. The panties were last, trapping my tool in a silky, slippery prison of nylon and lace. Still fully erect, it made a bulge in the front of the beautiful new panties. At this point, Mistress joined me.
"That just will not do! You simply cannot go to work like that. Go and get your cuffs!"
I did as I was told and soon found myself with my wrists cuffed together and attached to a hook in the ceiling normally used to hang a plant. After pulling my panties to my knees, Mistress took a pair of her panties from the laundry hamper and used them to stroke my cock until I spurted my load into their silky depths. She left me strung up until my spent cock returned to a flaccid state.
"That's much better", she said, wiping the last of my cum from my cock. "Now, I'm going to release you and let you finish dressing. You will present yourself to me for inspection before we leave for work."
It seemed so strange to be putting on a man's dress shirt and suit over my pretties. I discovered that in order for the camisole not to show through my shirt, I had to put a T shirt over it first. I didn't think the girls at the office would understand if they saw my red and black lingerie peeking through. I stepped into my wing tips and went to present myself to Mistress.
"You look satisfactory slave. I want you to remember that I will expect you to get out of your male clothes as soon as you enter the house this evening. I will have something suitable for you to wear laid out for you." With that, she kissed my on the cheek and patted my panty covered butt, sending me off to work.
Of course there was a mountain of work piled on my desk. My secretary, Ashley, had them sorted by priority and we spent the day just taking care of the most pressing matters. As we worked, I couldn't help noticing how attractive Ashley was. Each time she bent over the desk to pick something up, her blouse billowed open affording me a glimpse of her creamy breasts barely restrained in a lacy blue bra. On several occasions, she would invent reasons to brush against me, rubbing her butt against my crotch. If I had any thought of trying to instigate a little office tryst, my panties reminded me of how futile that would be. Ashley continued her teasing and flirting for the rest of the day. By the time it was time to leave, my cock was straining against my panties, aching for release.
I returned home to find a black peignoir set laid out for me. I stripped off my clothes, hanging my suit up and placing my lingerie in the laundry hamper. I noticed that the panties held the evidence of my excitement during the day, with numerous stains where my cock had oozed pre cum. I showered and slipped into the lacy gown and robe before going into the living room where Mistress awaited me. She had a bottle of White Zinfandel and two glasses set out. I poured the wine and dutifully gave her a kiss. She patted the cushion next to her, indicating that I was to join her on the sofa. As we talked about my day, Mistress turned the conversation to questions about Ashley. She wanted to know what she was like and how I treated her. I told her that Ashley was my right arm and that I couldn't function at the office without her. There was no way I could tell her of Ashley's attempts to arouse me. I would have been forced to admit that I had become excited, staining my panties with the evidence of my stimulation.
Mistress gave me an odd smile and changed the subject. The rest of the night was taken up with preparation of our dinner and the ensuing cleanup, followed by our retiring for the night. Of course we made love, with me tied to the bed and Mistress riding me to climax. When I came, it was an extremely intense orgasm, my cock pulsing with load after load of hot cum.
"My goodness, but aren't we the hot little thing tonight", Mistress commented. "I wonder what it was that got you so worked up. It can't just be the panties, I've had you in them for weeks now. I would certainly like to find out just what it is that's getting you so excited. I am sure it is something at work, that's the only change in your routine since I've pantified you on a permanent basis."
I was untied and we went to sleep. The next morning, when I came out of the shower, my lingerie for the day was all black. The only unusual item was the panties. Embroidered across the front was the message, "Property of Mistress Jackie". I was just pulling them up my legs when Mistress came into the room.
"Your performance last night has me convinced that there is someone in your office is trying to tempt you into doing something really foolish. I am quite sure that you would never be the one to instigate anything. I am equally sure that one of the women there is teasing you, attempting to start an affair of some sort. The panties you are wearing today should put a stop to any sort of hanky panky that person may have in mind." She then turned and left me to finish dressing.
That day and the days that followed were pure torture. Ashley wasted no opportunity to tease and torment me with her flirting. She would brush against me, rubbing her ass against my crotch even when there was plenty of room for her to pass. Her blouses became more and more provocative, either with buttons undone or being so sheer as to allow her lacy bra to show through. Her skirts got shorter and shorter, until I was treated to a constant display of her stocking tops with the garters attached. My cock spent an awful lot of time fully erect, a state that was not lost on Ashley. Of course all this titillation at the office made me most anxious to get home at night. There at least, I knew there would be a chance for relief. Mistress said nothing more about how excited I was when I arrived home, concentrating instead on finding new ways to humiliate and torment me. I have to say that this was my favorite time of the day. Driving home, I would try to imagine what sort of sweet suffering I would be subjected to that evening. I was never right. Mistress always surprised me with fresh ways to tie and tease me.
The situation at the office came to a head about two months later. It was just after lunch. Ashley pretended to trip and reached out to steady herself by placing her hand against my thigh. When she straightened up, she gave me a shrewd smile and I knew she had felt my garter strap. Nothing more was said about it and the day seemed to end normally. I mistakenly thought that either I was wrong or that Ashley was going to forgo acting on her discovery. The next day was to prove just how incorrect one man can be.
Mistress met me that fateful morning as I stepped out of the shower. "I have a feeling that today is going to be a very special one for you," she said mysteriously. "That calls for special undies. Yesterday, I received some very different lingerie for you to wear just for this particular occasion."
I followed her to the bedroom where laid out on the bed was a pair of very unusual pink panties. Actually, they were closer in design to bloomers than panties. "You know of course what these are called", Mistress said, picking them up. "Just to remind you, they're called "sissy" pants." Look at all the rows and rows of lace covering them. These panties are truly deserving of their name. Only a true sissy girl would wear these. They are the ultimate in femininity." Once my garter belt and stockings were properly in place, Mistress knelt in front of me and commanded me to raise each foot in turn as she personally attended to putting the new panties on me. She pulled them up over my cock and balls, trapping them in a slippery nylon prison. She added a pink camisole with lots of pink ribbons and lace and the outfit was complete. The panties came down my thighs to the tops of my stockings, trimmed with row after row of lace. As Mistress led me to the mirror to admire her handiwork, I loved the tight caress they held me in. Mistress kissed me good bye, admonishing me to be a good girl.
I arrived at the office at my normal time only to discover that Ashley had called in, telling the receptionist that she would not be in until after lunch. The only reason she gave was that she had some personal errands to run. I didn't think too much about it and set about taking care of those things that I wouldn't need Ashley's help with. Before I knew it, it was time for lunch. Because I went with some of the guys from marketing, lunch took a little longer than usual. I returned to the office at about 1:30. When I went to my office, I found the door was locked. That was most unusual. I had never locked that door in the five years I'd been there. I rattled the knob a little, then tried to think where I might have left the key. I was just about to turn away when I heard the door being unlocked. I entered the office to find it completely dark, the lights turned off and the blinds drawn.
Ashley's voice broke the silence. "Lock the door and turn and face it!" I don't know why I did as she instructed, but I did, perhaps because Mistress had conditioned me to obey instantly.
"Put your hands behind your back, NOW!!!," her voice commanded.
Again, without hesitating, I did as I was told. I felt something metallic being placed on my wrists and seconds later a series of clicking sounds told me I now had my hands hand-cuffed behind me. A scarf was then placed over my eyes and knotted behind my head.
Ashley's voice came to me again, "There, that's much better. Follow me, I'm going to lead you to your chair." She gripped my belt and turned me around, then led me slowly over to my desk. I was turned around again and pushed until the backs of my knees contacted the seat of my chair. I felt my arms being raised then pushed back until I was seated. My arms were now behind the backrest of the chair. I heard Ashley walk to the credenza on the other side of my office and return. After releasing the first set of handcuffs from my right wrist, she fastened my left hand to the arm of the chair. She slipped my right arm out of my suit coat and then unbuttoned my shirt and did the same with that. After re-fastening my right arm, she repeated the same procedure with the left, using another set of handcuffs. When she was done, I was left wearing nothing above the waist but my lacy pink camisole.
"My, my but aren't you the pretty little thing," Ashley cooed. I wonder what you're wearing under your slacks." I felt her nimble fingers at my waist, making short work of my belt and zipper. Next, my shoes and socks were removed. "Raise yourself off the chair so I can get these slacks off. I want to see your panties."
Again my training took over and I meekly complied. I felt my slacks sliding down my thighs, exposing my sissy pants and garter belt. When the slacks were completely off, Ashley used two more sets of handcuffs to fasten my legs to the pedestal of the chair. The manner in which she did this caused my legs to spread wide apart, leaving me totally exposed and vulnerable. Despite my predicament, my cock began to grow inside the sissy panties. Not helping the situation were the fingers tracing the outline of my tool, impelling it to greater size.
"Goodness, look at what I found", Ashley teased. "There is a full size cock in this little girls pretty panties. I always wondered why you seemed to pay more attention to my lingerie than you did my charms when I was trying to get your attention these past months. It seemed the lacier the bra, the more you stared. I began to suspect that you had a lingerie fetish. Yesterday, when you bent over to pick up something from the floor, I was sure I saw the outline of a garter strap through your slacks. Of course, I had to be sure and my make believe stumble clinched things. As soon as I knew you were wearing lingerie, I started to make my plans for what is to transpire today. I have enjoyed dressing boys in lacies since I was in my teens. Some of my fondest childhood memories are of the times my sister and I would dress my little brother. The three of us would then have "tea parties". Of course, because he was my brother there were certain things we couldn't do. Now that I've got you where I want you, I can take my fantasy to the next level".
Ashley then picked up the phone and called the switchboard. "Hi, this is Ashley. Please hold all Jim's calls. He's going to be tied up all afternoon." It was all she could do to suppress the giggle that escaped the instant she hung up the receiver.
There was silence for a moment, the I heard the unmistakable sound of a Polaroid camera spitting out several pictures. This was followed by the sound of my office door being unlocked, opened and quickly shut again. I sat there helpless, wondering what would happen if someone should wander in. After several moments, I heard the door once again being opened and re-locked.
"There, now I have all the control I need", Ashley boasted. "I just mailed the pictures of you in your lacies to my home address. You will now do whatever I tell you or face the risk of those pictures being posted on the company bulletin board. For the moment, you can sit there and wait while I prepare your first surprise".
The irony of her statement wasn't lost on me. I had no choice but to do just that. The handcuffs prevented all but the most rudimentary movements. I could hear what sounded like someone removing their clothes, sounds like the click of fingernails on buttons, the unmistakable purr of a zipper being pulled down, the whisper of silk sliding against skin. My imagination ran rampant with minds eye pictures of what Ashley was wearing under her street clothes. Would it be the pretty pink bra or perhaps the sexy black one she had tantalized me with just last week? The answer was soon in coming. I felt Ashley undoing the knot in the scarf. As it fell from my eyes she cautioned me, "Keep your eyes closed until I tell you to open them".
Thirty seconds later she spoke again, "All right my little slut, you may open your eyes now and gaze at your captor".
It took a few seconds for my eyes to adjust to the light now flooding the room. Ashley was standing in front of me, just inches away. She was leaning against my desk with her legs slightly apart. Her long, blonde hair was pulled over one shoulder, cascading down and partially concealing one breast. Her lingerie consisted of a white half cup bra and crotch-less panties, both trimmed profusely with pink lace. Her garter belt was all pink, holding up her pink lace stockings. Because the bra had only half cups, the breast that wasn't covered by her hair had it's nipple exposed. Also, her position caused the slit in her panties to gape open, offering proof that she was indeed a natural blonde.
"Do you like what you see? I'm sure you never dreamed that the day would come that you would be allowed to view your sweet little secretary in her scanties. I think you'll like the name I have for this outfit. I call it my "rape suit". That's exactly what I have in mind. I'm going to use my pussy to rape that cute little cock you're hiding in your panties. Even though I'm wearing a complete set of lingerie, all the goodies are accessible. I didn't want to have to bother taking off either my panties or bra when the time comes for me to make use of your hot mouth or stiff love pole."
To demonstrate, she leaned forward, placing her nipple at my mouth. "Show me how well you can pleasure me slut. Make my nipple hard or you'll never get out of this chair".
I did as she said, sucking her nipple into my mouth and running the tip of my tongue over and around it until it was fully erect. Her breathing began to deepen, her hands gripping either side of my head, trapping my face against her. "Oh, that's very nice", she purred. "Now do the other one". She pulled her hair out of the way and presented her other firm breast to my tender ministrations. This time, while I continued my oral attentions, I felt her reach down to my panties, insinuating her hand under the waistband. Her cool fingers wrapped around my erect cock, making me gasp with pleasure. "Goodness me, what a large clit you have my dear," she teased. "I'm sure I can find a good use for this, but to make sure that it remains in it's present state, I have something for you."
She pulled away and walked over to her over-sized purse, returning with a leather strap. It was about a quarter inch wide and six inches long. She pulled my panties down to the tops of my thighs and began to stroke my cock, oops, excuse me my clit. When she was satisfied that it could get no larger, she wrapped the leather strap around the base of my clit and balls and pulled it tight. Bending over, she gave the head of my clit a quick kiss before pulling my panties back into place. The strap made my clit stand at full attention, making a large bulge in my pink panties.
"There," she said, stroking me through my panties, "that will keep your clit nice and hard until I decide to take the strap off. It will also prevent you from reaching climax. Your clit is mine to do with as I please for as long as I want. You have no control over your own body. I will decide when and if you are allowed to come. Before that will happen, you will first have to pleasure me. Only when I am completely satiated will I even consider allowing you to have any form of relief. You are after all, in no position to argue."
"I think I'm going to allow you to worship my pussy with you hot little tongue. But before we can do that, I'm going to have to get you out of that chair. Please don't entertain any ideas of resisting. You wouldn't want any of our co-workers to hear us and come to investigate, would you."
I nodded my assent and she undid the handcuffs from the chair, leaving them attached to my wrists and ankles. After clearing my desk, she motioned me to lay down on my back with my head hanging over the edge. Once I was positioned to her satisfaction, she handcuffed each wrist to the corresponding ankle. Next, she took two lengths of rope and tied one around each thigh, just above the knee. She tied the other ends to the legs of the desk, after first pulling them tight, spreading my legs far apart. I was once again completely helpless. Ashley had complete access to whatever parts of my anatomy she wished. There would be nothing I could do by lay there and take it. She wasted no time in taking advantage of my plight.
She came around to where my head hung over the edge of the desk. I had a perfect view of her sweet pussy. As she came closer, I could see the drops of moisture already leaking from her lips. The pink lace of her split crotch panties made an attractive frame for her love tunnel.
The elevation of the desk allowed her to stand with one thigh on each side of my head, placing her pussy over my mouth and nose. I needed no prompting as to what she expected of me. My tongue darted into her folds, seeking the prize of her clit. I ran it slowly up and down the entire length until I felt her growing nub. It took only a few flicks of my tongue to start her juices flowing. It was like nectar, impelling me to greater and greater efforts. As the tempo and pressure I applied increased, so did her breathing, until she was gasping for air and moaning softly. I was able to suck her clit into my mouth and press it between my lips as I rapidly lashed at it with my tongue. This sent her completely over the edge, her body shaking and trembling as wave after wave of pleasure shot through her. It was all I could do to keep up with the honey pouring from her tender slit. When the last tremor subsided, she backed away and sat sprawled in my chair. Her legs were wide apart, her swollen pussy still glistening with her juices. This made for a picture that you usually only see in some of the men's magazines. I couldn't take my eyes off her, my cock aching for a chance to delve the depths of her tight snatch.
"Goodness, but you are certainly a talented little slut," she sighed. "I haven't had my pussy eaten like that ever in my life. I honestly thought for a minute there that I would faint. I'm going to have to think of a way to reward you. Perhaps a special surprise is in order. There is one surprise that I have been saving for just the right moment. You will just have to wonder what it is and when I'm going to give it to you."
"I want you to look forward to our times together and there is no better way to do that but to allow you to have some pleasure too. I wonder what a tramp like you likes best. Would you respond better to me taking your stiff clit into my pussy or my mouth? Perhaps a combination of the two, yes that's it."
She stood up and walked over to where I lay bound and helpless. Her fingers stroked my clit in it's satin prison as she continued, "After I've caught my breath, I'm going to drive you right up the wall with desire before I take the strap off and let you spew your load deep inside my steamy pussy." She licked her fingers and pulled the foreskin back, running her fingers around the head of my cock. "For now, I want you lay there and think about how good it will feel as my lips slide over the head of your clit, sucking it deep into my mouth. My tongue is going to dance around the head, with special attention paid to the underside of your glans. When I think you are ready, I'm going to straddle you helpless body and let you watch as my pussy devours your clit. Think about how good it will feel as inch by inch, the silky hot folds of my pussy slide down around you until all you can see is the slit in my panties pressing against your pubic bone."
She wrapped her warm hand around me and began to gently compress my cock with a slow rhythm. "This is only a hint of the way it will feel when I use my vaginal muscles to squeeze you and caress you, making you long for orgasm. Naturally, you will only be able to lie there, a prisoner inside my me until I start to slowly move myself up and down." She began to slowly stroke my cock, continuing with her verbal teasing, "Your clit is going to be driven wild by the feeling of my wet, glove-like pussy stroking it." Between the images she was planting in my mind and the continued manual attention I was getting, I was hotter than I could ever remember. I could feel the cum boiling in my balls, screaming for release. Suddenly, there was a soft knock at the office door, three taps followed by two more. It was obviously some sort of code.
"I think your special surprise is here", Ashley chortled. I turned white with fear as she went to open the door. What if she had decided to let my secret out? I would have to resign my job and move to another city. There would be no way I could continue to work in my present position if the word got out that I dressed in frilly lingerie and allowed myself to be tied up and dominated. These and a thousand other thoughts raced through my mind as I struggled against my bonds. I don't know what I hoped to accomplish, there was no way I going to get free. I only knew that I had to try.
Thankfully, Ashley opened the door only wide enough to admit our visitor. You can imagine my surprise when in walked Mistress Jackie. I laid there in stunned silence as she walked over to the desk and smiled while she surveyed my plight.
"Look at you all tied up and helpless! You are such a slut. The first woman that comes along and you lie down and spread your legs for her. I suspected as much. That's why I have been planning this with Mistress Ashley for the past few weeks. She and I met at last month's company party and discovered that we had a great deal in common. We got to talking about what turned men on. She asked me if you liked to see a woman in pretty lingerie. We both had a good laugh when I told her just how much you really liked them. She posed the idea for what has transpired today and I of course I agreed. She even stopped by my office yesterday to deliver the special lingerie you are wearing now. I must say, you are a most fortunate slave to have two Mistresses buying you pretty things. You will have to show your appreciation to both of us."
She turned then to Mistress Ashley, "I hope he didn't give you too much trouble Ashley."
"Not at all Jackie, you have him or should I say her, very well trained. She responds immediately to the female voice. In fact, he seemed to enjoy the trials and tribulations I put him through."
"Judging by the size of his clit, I would have to agree. I could have predicted it though. Every time I have put him in his panty prison, his clit grows until sometimes, I think it will burst. What do you suggest we do with him now? I have to admit that the sight of him all tied up and helpless has had it's usual effect on me. My pussy needs the special talents only his tongue can provide. I was listening at the door for a while before I knocked, so I know what you have in mind. Since I'm in no mood to wait, I think the poor dear will just have to accommodate both of us at once."
Mistress Jackie fixed her gaze on my eyes as she slowly disrobed. Under her street clothes she wore an outfit very similar to Ashley's. Her red panties were crotch-less with white lace and the bra instead of having half cups, had white lace holes for her nipples to peek through. She bent over, placing her face just inches from mine, "What a lucky slave you are", she teased. "You are about to be granted a privilege few slaves ever get. You are about to serve two Mistresses at once. Mistress Ashley is going to avail herself of your hard clit while I put your mouth to good use. If you do a good job, you may be allowed to come, but not before Mistress Ashley and I have had our way with you first."
Mistress Jackie adjusted my bonds so my head was no longer hanging over the edge of the desk. "I want our slave to be as comfortable as possible while we use him." Tugging my panties down to the tops of my thighs, exposing my rigid tool, she continued, "Ashley, why don't you get started first? I think our slave would like to be able to watch while his clit is gobbled up by your pussy."
Mistress Ashley climbed up on the desk and straddled my hips. Her stocking clad legs rubbed against mine, creating the most wonderful friction. Mistress Jackie, not wanting to be left out of the fun, fed her nipples each in turn to my ready mouth.
My cock was now at full attention, craving the caress of Mistress Ashley's womb. After first pulling my foreskin back to expose the sensitive head, she stroked my cock up and down the length of her slit, coating it with her hot oils. I felt as though an electric shock had gone through me. All the attention had made me so hot my hips involuntarily attempted to thrust upward.
Ashley quickly retreated out of range, chiding me. "You are getting a little impudent slave. I will be the one to decide when you are allowed inside me. Now be a good little slut and lie still while I prepare the two of us for the ultimate utilization of your clit." She continued teasing the head of my tool with her velvet folds, her juices and mine mingling to drench my cock, preparing it for its journey into her depths.
At last she was satisfied with the preparations. She lifted herself above my distended sausage and using one hand to guide my cock and the other to spread her lips, she lowered herself ever so slowly. If it hadn't been for the strap preventing it, I would have lost control the instant her slippery labia wrapped around me. As it was, she had only taken a third of me inside her when the pleasure became so intense I began to moan loudly.
"Jackie, our slave is making entirely too much noise. Why don't you put something over his mouth to at least muffle some of the volume. I wouldn't want anyone coming to investigate what's going on in here."
Mistress Jackie was only too happy to comply. She got on the desk facing Mistress Ashley with one knee on either side of my face. The white lace trim of her panties was already soaked with her juices, giving mute testimony to her state of arousal. The scent of her musk drove me wild as I lay there anticipating the arrival of her sweet flesh on my mouth.
By this time, Mistress Ashley had completely impaled herself on my aching tool. The sensations were more than she had promised. My cock felt as though it were in a hot velvet vise.
Mistress Jackie lowered herself to me, placing her swollen clit at the precise point where my dancing tongue could do the most good. "All right slut, lick me until I come. Mistress Ashley and I are going to play with each other while we rape your clit and mouth at the same time."
I bent to the task with delight. There is nothing that pleases me more than pleasuring my Mistress with my tongue. While I licked and sucked at Mistress Jackie's love button, I could feel the strap around my cock and balls being removed as Mistress Ashley began to raise and lower herself on my bloated cock. As she began to move faster and faster I could feel her pussy contracting as her climax neared. At the same time, Mistress Jackie was pushing her clit harder and harder against my mouth. Suddenly I could hear the moans of pleasure as both of them hit their peak at the same time. Mistress Ashley hot pussy began to spasm, gripping my cock until I joined them, pumping my hot load deep inside her.
My life now is one of complete submission to two beautiful women. Mistress Jackie oversees my life at home and Mistress Ashley takes over when I go to my office. Needless to say, I couldn't be happier.
© 2001 by Miss Vicky. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.