Helen's Pantypet
Part One

A fantasy by Miss Vicky

All the events depicted in this story are fictional and only exist in my fantasy world.  With that said, slip into something pretty and read along as Helen takes her boss from three piece suits to three piece peignoirs!

How do I begin? I suppose the at the start, back before I became my secretary's panty boy. I was a typical executive, well paid and on the fast track to what was referred to in our company as "mahogany row." I had what most men aspire to, a good paying job with a nice home in the suburbs. Other than the occasional one night stand, there was no woman in my life. Other than that, I had it made!

All that changed the day I got a new secretary. My previous secretary, Mandy had quit unexpectedly, leaving me with a pile of work and no one to help. I had no idea as to why she would want to leave. Her letter of resignation had only given "personal reasons" for her leaving.

I hadn't realized just how much I had depended on Mandy to help me with the seemingly unending details of running my department. I was at my wit's end and would have accepted anyone by the time personnel sent Helen to me for an interview.

I was at my desk, attempting to make some sort of order out of the chaos that was that mornings mail when there was a soft knock on my office door. "It's open," I responded. The door opened and the most striking woman I had ever seen strode through, closing the door behind herself. She was tall with shoulder length strawberry blonde hair. She wore a navy blue blazer over a sheer white blouse and a wine colored pleated skirt. I noticed her stockings were also navy blue with a discreet seam down the back.

"Good morning Mr. Adams, my name is Helen Carter. Your Personnel Department said you needed an executive assistant. They sent me here to interview with you."

"Please, has a seat," I replied. "Tell me a little about yourself and your experience."

She sat in the chair opposite my desk and crossed her legs before beginning. "I'm afraid there's not much to tell. My last position was that of executive assistant to the CEO of a large manufacturing concern. They were bought out by a competitor and absorbed into the parent company. That left a lot of people out of work, but I have a trust fund left by my father that more than meets to my expenses. I haven't worked for six months primarily because I don't really have to. The only reason I re-entered the job market was I have become bored just sitting around my house."

She continued, filling me in on her education and past employment, highlighting those positions that were pertinent to the opening as my assistant. As she spoke, she crossed and re-crossed her legs, causing the hem of her skirt to ride up just a little time. The final time revealed a lacy pale blue garter strap holding up her stockings. Try as I might not to peek, my gaze kept returning to that sight. I have always had a penchant for women in pretty lingerie and couldn't help but wonder if the rest of her lingerie was as provocative. I looked back to her face to see a slight smile on her lips as she continued. Had she caught me ogling her? I hoped not. There was more than enough on my plate at the moment without a harassment lawsuit.

I tore my eyes away and forced myself to look only at her face while she finished. "Do you have any questions about me?" I asked.

"Yes, as a matter of fact, I have quite a few," she answered. She then proceeded to ask all the normal questions about the position, hours, duties, benefits and wages. I answered

them all, filling in the details that I was sure Personnel had omitted. The next series of questions surprised me.

"If we are to work together, I have to know a little more about you personally," she said. "I hope you don't mind some questions along these lines."

"Not at all," I replied. "Ask anything you like, I have no secrets."

She then asked if I was married, divorced or never married, and if I had a regular girlfriend. She then wanted to know what I looked for in a woman, asking a series of questions each more personal than the one before. Before long, she knew every intimate detail of my life, right down to my appreciation of women in pretty lingerie. She had an aura of power about her, one that compelled me to tell her my inner most secrets.

At the end of all this she said, "I will accept the position on a 30_day trial basis. If I am unhappy for any reason at the end of that period, I will leave."

Because I had a very important report due at the next board meeting, I blurted out, "The position is yours."

"I will start tomorrow morning then," she said as she stood to leave.

"That will be fine. I look forward to working with you. If it's not too much an imposition, I would like you to be prepared to work a little late tomorrow. I'm afraid the backlog of work will require that we do that for a few nights to get ready for the board meeting."

She smiled softly and said, "That poses no problem for me, I look forward to the challenges I see here."

With that, she left leaving me to my thoughts. My joy at finally getting some help had outweighed everything else. Otherwise I would have noticed that she had not made any reference to what would happen if I was unhappy with the arrangement. In reflection, I could see that she had adroitly turned the tables on me, extracting all the information she needed. I now know that the interview had little to do with the opening, but more Helen's quest for a man she could bend to her will.

The next day came and I was at my desk trying to set priorities the day's work when Helen arrived. "Good morning," she purred. "Does my attire meet with your approval?"

I looked up from my desk to see her standing there, wearing a red blazer over a diaphanous black blouse with a matching skirt. Moving my gaze down, I saw that she once again was wearing stockings, red this time. The blouse was so sheer, I could easily make out the outline of her lacy black bra. "My goodness Helen," I gasped. "How do you expect me to keep my mind on my work?"

"That will be your problem, won't it," she teased. "I wanted to make a special impression on my first day. I saw you gaping at my legs yesterday. You know, I don't think my legs interested you as much as the garter strap I allowed you to see. Did you really think it was an accident that my skirt rode up like that? Don't be silly! I knew exactly what I was doing. It was a test of sorts and I must say I got the reaction I was looking for. I knew in that moment that you are the sort of man I was looking to work with. You told me far more about yourself than you realize. All that's required is a little cooperation on your part and I'll be able to show you just how happy you can be working with me."

At this point, she shrugged the blazer from her shoulders and draped it over the back of her chair. "Let's get to work then," she said.

The days that followed seemed to fly by. As the deadline for the board meeting approached, Helen and I spent many late nights working together. I was ecstatic with her! She seemed too good to be true. She was efficient and intelligent, many times catching things I had missed. During this time, her demeanor changed subtly. She began to take more authority in the relationship, sometimes teasingly threatening me with a spanking if she caught me in another mistake.

Helen was well aware of the effect she had on me and made the most of it. When showing me something in a document, she would bend over the desk, giving me a view of the lacy bra she had selected for the day. Other times, she would wait until she was sure I was watching when she reached for something on the top shelf of the supply cabinet. I always got a show of stocking and garter strap as her skirt rode up.

Her lingerie wardrobe was extensive. Not one day went by without her giving me a glimpse of her lacy intimate things. She knew what she was doing. She would sometimes catch me looking at her and just smile, letting me know that I had been caught. Sometimes, she would blatantly stare back, daring me to look some more.

Finally, the day arrived that we were finished with the report. Helen walked triumphantly up to my desk and dropped it in the middle. "There you are Jim, it's finished at last!"

"That's great," I replied. "At the risk of sounding like I'm coming on to you, can I take you to dinner to celebrate?"

"That would be wonderful, but I need time to change first," was her response. She took a post-it note and wrote her address on it. "Be here at 7:00 tonight. I have a surprise for you, one that I've been planning for a long time now. I have the feeling that tonight will mark a distinct change in your life."

Her cryptic comment left me so taken aback, I didn't respond. I simply took the address from her and put it in my wallet.

She got her coat and called out as she was leaving, "Make sure you're on time, or I'll have to punish you for being naughty."

I wondered what she meant by that, but gave it no further thought. I had grown to appreciate Helen, especially her choice in office attire. I wondered if there would be a chance of something developing outside the office. I knew that was a bad idea, in fact the company had very strict guidelines prohibiting personal relationships. I decided that it was worth the risk. If Helen seemed amenable, I was going to take the chance and see if I could develop something more than a working relationship with her. Little did I know how prophetic these thoughts would be.

I finished the few remaining things for the day and went home to shower and get ready for my date with Helen. I left the house early and stopped at a florist shop for a dozen roses before driving to the address Helen had given me. I found it in an upscale area of town, one where only people with substantial wealth lived. It was out of my reach and I wondered how Helen had managed to afford it. Her house was a colonial style with a cobblestone drive. I pulled through the open gate and parked behind a newer Chrysler convertible. I walked to the front door, roses in hand and rang the bell.

You can imagine my surprise when the door was opened by Helen dressed not in attire suitable for going to a nice restaurant, but rather a flowing red peignoir.

"I changed our plans for the evening," she said simply. "I want to spend some time getting to know the man I work with and have decided that a crowded restaurant would not give us the privacy I want."

I couldn't help but stare at this exquisite creature. The peignoir was shimmering satin with a lavish amount of black lace at the bodice and wrists. Her feet were in a pair of mules with marabou trim and 4" heels. This ensemble was designed for only one thing, to incite the senses and arouse the viewer.

She turned around and as she walked away directed, "Don't just stand there gawking at me, we have to get those beautiful roses in some water."

I followed her meekly, wondering what this was all about. We passed through the living room to the dining room where the table was set for two with elegant crystal and bone china. Helen went to the china cabinet and took out a crystal vase and handing it to me instructed, "Go through that door to the kitchen and fill this half full with water. I will use these as a centerpiece on the table."

I followed her instructions and returned with the vase to find Helen sitting on the couch, pouring two glasses of wine. "I thought we'd have a glass or two of wine before dinner. "Here," she said, patting the seat next to her, "You look like you need to relax a little. This is a very good Chardonnay. I found it while on vacation in France last year." Her next statement had a somewhat mysterious edge to it, "I hope you enjoy its special flavor."

I took the proffered glass and took my first sip. The wine had an interesting, if somewhat piquant taste. We chatted inanely for a bit about the different people at the office until I felt a warm glow infusing my body. I felt somewhat disoriented, even though my speech continued to be precise and my mind was still alert.

Helen smiled at me over the rim of her glass and spoke with a soft voice, "Is the wine to go to your head my pet? I hope so. I would hate to waste it. Since it's too late for you to do anything about it now, I may as well tell you that I put a mild hypnotic sedative in your glass while you were filling the vase. You will remain alert and aware, but your will to resist is considerably diminished. What I am about to do is implant thoughts in your subconscious. You won't even realize they are there, but will feel compelled to follow the urges they will engender. I have noticed your affinity for my pretty lingerie. This tells me that there is a good chance that you are the type of man I've been looking for."

She pulled my face forward and kissed me, snaking her tongue deep into my mouth. There was no doubt as to who was the aggressor her. Continuing the kiss, she took my hand and placed it on her thigh. "Feel how silky my gown is. Can you imagine how good it feels to be dressed in something so elegant? I can tell you that it makes me feel very special and pampered."

I could feel the warmth of her thigh through the satiny material. She moved my hand higher until it was at the essence of her femininity. "Feel how warm this is getting me," she whispered. "Just the thought of getting you into your first pair of panties is getting me very wet. Once I'm finished with you, I will have the best of all worlds a lesbian lover with a penis."

Still holding my hand, she stood and said, "Follow me, I have a surprise for you upstairs."

I didn't understand what was happening to me, only that for some odd reason I had to obey. It was as though my will to resist had been totally subverted by whatever she had put in my wine. I meekly followed her up the stairs, entranced by the swaying of her hips in the pretty peignoir. We reached the upper level and she led me through the doorway to what I surmised was her bedroom.

In the center of the room was an ornate four poster bed. Laying on the satin comforter was a complete set of red satin lingerie. She walked over and picked a pair of panties and held them up in front of my face. "Look at how pretty these are. Look at all the delicate black lace trim." She then began to rub them against my cheek. "If you think this feels good, I want you to imagine what they would feel like if you were to wear them. Imagine what they would feel like as I slowly pulled them up your legs until finally they settled over your male parts, trapping them in a prison of satin and lace."

"Here, hold these a minute, I want to get you out of these nasty boys' clothes," she said as she began unbuttoning my shirt. "I have noticed the way you look at me while we have been working and I know you want to get into my panties. Well, here's your chance. I have always wanted my own panty slave and you are going to be it."

She continued to gently undress me, stroking and kissing my bare flesh as it became exposed. As soon as my tee shirt was off, she bent slightly and licked my nipples. As they became erect, she smiled mischievously and purred, "All girls like this. Your nipples are just as sensitive as mine. I hope you can do as good a job once I give you the chance."

She continued undressing me while I stood there and meekly accepted what was happening to me. My shoes were untied and removed, along with my socks. She unfastened my belt and after pulling down the zipper, she grasped both my slacks and underwear and pulled them down to my ankles. "Step out of them please," she requested. Once again, I submissively complied, wondering why she had this hold over me. Of course, the drug she had slipped me had some effect, but that couldn't explain my raging erection. Could it be that I secretly wanted this to happen?

The fact that I was erect wasn't lost on Helen. She held it in the palm of her left hand while stroking it with her right. "My baby certainly seems to like all this attention, doesn't he? Wait until I put the panties on you. You're going to love how they feel. Before we can do that though, we have to make your body more feminine in appearance."

Still holding my erection, she used it as a leash to pull me into the adjoining bathroom. At her direction, I stepped into the shower and stood there while she adjusted the water temperature. She reached into a drawer in the vanity and retrieved a lady's razor. "We can't have all that nasty hair getting in the way of your enjoyment of your lacies, can we?"

She lathered me up from head to toe and shaved me completely. Yes, I mean even my groin. When she was finished, she stepped back and admired her work. "That's much better. You look adorable now, just like a virginal young girl. Well not exactly, most girls don't have as big a clit as you. I'm sure I'll find a good use for that though. Come on, out you go, it's time to make you pretty for your new Mistress."

This was the first time she had referred to herself that way. I found it somewhat disconcerting, yet comforting at the same time. Now, no matter what happened, it wouldn't be my responsibility. Helen was making all the decisions, making me free to accept and enjoy what was happening to me. I followed her back into the bedroom where the lingerie and my fate awaited me.

She first picked up a red corset with lavish black lace trim. "Before I can put you in your panties, we have to give you a more rounded figure. I want you to grab the post of the bed and hang on while I lace you into your corset. I know this will feel a little uncomfortable at first, but it's something all girls have to get used to."

I did as I was told and before I knew what was happening, Helen had me tightly laced in the embrace of the corset. The under-wired cups pushed my chest muscles up and in, giving the illusion of small breasts. "Now for the stockings," she said. She showed me how to roll them and slid each one in turn up my legs. The feeling of these silky things slipping up my now hairless legs was incredible! By the time both were on, my cock was twitching with lust. I looked down at the shimmering black fabric encasing my legs and wondered how anything could feel this good. I attempted to fasten the garter snaps, but couldn't seem to get the hang of it. After watching me fumble for a few seconds, Helen pushed my hands aside and showed me the proper way to fasten them. Once this was done, she indicated that I was to stand. I looked down to see my penis framed perfectly by the lacy garter straps of the corset.

"I suppose you're wondering why I put you in the corset first. That's actually quite simple when you think about it. This way your panties can be easily pulled down without having to fiddle with the garter straps. As the night goes on that will be a real advantage for both of us. Now my pet, the moment we've been waiting for, your first time in panties. This moment is special, one that will remain with you for the rest of your life."

She took the panties from me and knelt in front of me. "Pick up one foot at a time dear so I can get my beloved in her panties."

Meekly, I raised first one foot, then the other. Helen began to ever so slowly pull the panties up my legs. The feeling of the soft panties rubbing against the silky stockings was like nothing I had ever experienced before. As they passed my knees, they seemed to gain a life of their own, stroking the insides of my thighs. At last, they settled about my waist, caressing my privates with their embrace. She next slipped my feet into mules matching her own. I teetered for a moment on the heels, but soon got the hang of them.

Helen stood and surveyed the results of her efforts. "You look divine! Your legs look fabulous in the stocking and the heels give them great definition. You truly are on your way to becoming my panty slave." Once again she thrust her tongue deep into my mouth while she reached down and softly stroked my panty covered privates. Breaking away she continued, "This means you are mine now. The moment these panties closed around your male parts, you ceased being the macho male. You have begun a journey, one where I will be the Mistress of ceremonies, so to speak. Come on, admit it. Doesn't lingerie feel so much better than those nasty boys' undies? How horrible it must be to have to wear those boring cotton shorts when you could spend your life dressed in the finest of satins and lace."

"I have to admit," I said, "This is unlike anything I have experienced. It's as though my cock and balls are being stroked softly with every move I make. You hands feel even better than I imagined they would."

"Oh, this is just the beginning my pet, here put on your peignoir robe and we'll go down to dinner." She handed me a robe that was the match to her own. I put it on reveling in the feeling of silky satin against my lingerie. We went downstairs to the dining room where Helen turned and asked, "Would you like a little more wine my pet?"

"It really isn't necessary," I replied. "I'm really enjoying what you have done to me. There's no need to drug me again."

"That's not what I meant," she replied. "Besides, there wasn't anything in the first glass except wine. I suppose it was naughty of me to suggest otherwise, but I wanted to see just how suggestible you were."

"You mean that everything that just happened was because I really wanted this?" I asked.

She took my hand and looked straight into my eyes. "Yes, my pet. You didn't do anything that you really didn't want to do. The one and only reason you're dressed the way you are is because you have secretly wanted it all along. All it took was a woman that could recognize your hidden yearning to wear pretty things. I recognized your affinity for pretties the moment I met you. I knew then that what we have shared tonight would come to pass. What you could not have known is that I have been searching for a man just like you for several years. There is something about a cross-dressed male that really turns me on."

She grasped my head gently and pulled my face toward hers. Once again we kissed, but this time her hands began to wander. First, my breasts were teased and my nipples tweaked. Then her fingers trailed lower until they insinuated their way inside my panties. Once there, they began to slowly masturbate me, taking a full five seconds to complete each trip up and down the length of my shaft.

Not wanting Helen to feel left out, I reciprocated, teasing her nipples through the red satin of her nightgown until they were fully erect. She moaned her approval, "Yes baby that's it, make my nipples hard. Suck them for me, play with me like the lesbian love you know you are."

Happy for the opportunity to please the woman who had shown me so much about my buried yearnings, I bent to the task with a will. I slipped the strap of her nightgown down, freeing her breast. I sucked her breast into my mouth and began to swirl my tongue around the circumference of her aureoles. Her breathing began to sharpen, each breath coming in a short pant as I flicked the tip of my tongue against her turgid nipples.

"Oh God, you're even better than I had hoped," she gasped. "You have me so hot I can't stand it." She raised the hem of the nightgown, exposing her pelvic area. To my surprise, she was wearing panties under her gown, but not the ordinary kind. These were red crotchless panties trimmed in delicate black lace. The lace framed her pussy perfectly, giving mute testimony that she was indeed a natural blonde.

"She reached down with her index finger and probed inside her honey pot. She held her finger to my mouth commenting, "Look what you've done to me you naughty slut. "I'm all wet now. What are you going to do about this?"

There was little doubt about what it was she wanted now. I kissed my way up her inner thigh to the junction of her legs. Her musk was sweet smelling with a distinct aroma. I needed no further prompting. I began to lick her, gently sucking the lips of her labia as I traveled up and down the length of her slit. I purposely avoided her clit, instead teasing her by coming just up to it and then starting back down. Not to be denied, she pushed me down on the couch and after pulling up her nightgown, straddled my face. Once in position, she let go of the nightgown, leaving me in a red satin tent with her pussy just inches from my face. As I lifted my head to her, she lowered herself until I was pinned against the cushions. "Suck me, you slut," she ordered. "Make me cum with your mouth. I want you to taste your Mistress's nectar."

I did just that, sucking her clit between my lips and lashing it with my tongue. I could feel her excitement building and when she was reaching her peak, I ran the length of my tongue over her clit. That was all it took as wave after wave of pleasure coursed through her body. Her thigh clamped down against my head, ensuring that I could do nothing but service her pulsing pussy. Her juices flowed into my devouring mouth, filling me with her personal essence.

As her tremors began to subside, she raised herself from me and then shifted position to allow her to lay next to me. She whispered in my ear, "That was incredible my pet. No man has ever given me an orgasm of that intensity before. You have all the ear marks of a good lesbian lover, one that understands what a woman really wants. I want to give you the same kind of pleasure now, but first I want you to accept that it has to be on my terms."

"You have shown me so much already," I replied. "I'll go along with anything you want."

"That's my girl," she exclaimed, reaching down to stroke my panty covered cock, "I promise you won't be sorry. All I ask is that you not question what I am about to do. It is in your best interest to just let it happen and enjoy it."

"Come on," she commanded, getting to her feet. "For what I have in mind, I want us to be comfortable."

She took me by the hand and once more led me to her bedroom. Once there, she said, "Take off your robe and your panties, then lie flat on the bed with your arms and legs extended toward the bedposts."

I began to comply, removing the robe and panties, but hesitated to get on the bed. I suspected that she was going to put me in bondage and that idea bothered me.

Sensing my trepidation, Helen calmly said, "I want you to do as I have instructed. If you don't do as you are told, you may consider the evening to be over. I will send you home and we won't see each other again."

Once again, the submissive side of me took over and I meekly complied, lying on the bed in the prescribed position. At that moment, I found myself wanting to please this enchanting woman more than anything else in the world.

Helen went to the night stand and retrieved four silk stockings. She turned back to me saying, "I want you to be completely free to enjoy what I'm going to do to you. Oddly enough, one way to accomplish that is for you to have all your options to resist taken away. I'm going to secure your hands and feet to the posts of the bed. When I'm finished, you will be completely exposed and vulnerable. You will just have to trust me here. I promise you I won't do anything to cause you harm."

She took the stockings and tied one end of each to my wrists and ankles, the other to one of the bed posts. While she did this, she continued speaking. "There are many things in this world that seem to contradict themselves. For example, I'm using delicate stockings to restrain you. Used one way, they are extremely fragile, subject to ruin from the smallest snag. Used in this manner they are incredibly strong, able to withstand the struggles of the strongest man. In the same vein, you will come to understand that in total submission comes total freedom. Only when all your options are taken away, will you become completely free to enjoy what is happening to you."

I struggled briefly, testing my bonds. She was right of course, there was nothing I could do but lie back and await my fate.

Helen wasted no time. She began by kissing me deeply, then trailing her tongue down my neck to the swelling above the cups of the corset. She pulled each cup down in turn, exposing my nipples. She licked around them before sucking each one into her mouth. When my nipples became hard, she gently bit down, sending shivers of delight through my body. I had no idea something like this could feel so wonderful. She continued by lowering her head to my legs. She began to kiss the insides of my thighs where the tops of my stockings ended. Again, I felt waves of pleasure course through me, my cock twitching in anticipation of what I was sure would come next.

Helen continued her teasing, taking my erection in her hand and with her lips just an inch away, blowing softly on the head of my penis. I thrust my hips upward in an involuntary attempt to meet her mouth, but she just laughed and pulled away. "Not yet my pet, all in good time. We have the whole evening ahead of us and we're just beginning."

She then reached down and retrieved the lacy panties I had been wearing. "Does my sissy miss his panties? Do you miss the feeling of satin against your clit? Your Mistress will try to help then." She took the panties and dragged them across my cock and balls, sending shivers of delight through me. "That certainly seems to have an agreeable effect on you, doesn't it? I wonder what would happen if I did this."

She wrapped the panties around my cock with the excess draped over my balls and began to masturbate me with them, slowly at first, then with an ever increasing tempo. I was sure she was going to allow me some release from the unyielding pressure in my loins, but that was not to be. The instant she sensed that I was about to climax, she would stop and chide me, "Not so fast dearest, you have to wait a lot longer than that before your Mistress allows you the privilege of release. You may as well learn to enjoy the fact that I am in complete control of your body. I will use it as my toy, playing with it in any manner I see fit. If I decide to bring you to the brink a hundred times that is what will happen. There is nothing you can do to stop me."

To illustrate her point, she began to stroke me again. Thinking I could fool her, I tried to feign a lack of arousal, thinking she might continue and inadvertently allow me the release I craved. This was not to be. She laughed at me saying, "Do you really think you can fool me? Not a chance, my pet. I know your body now and what to watch for while I'm teasing you. For trying to fool your Mistress, you will have to service me with your talented little tongue while you endure this five more times."

She once again straddled my face, forcing me to attend orally to her pussy. This only served to arouse me further, intensifying my desire to climax. True to her word she forced me to endure five trips right to the edge of paradise, while I licked and sucked her clit.

When she wasn't stroking my cock, I could feel her drag the panties over my body, paying particular attention to my groin. This was as bad as her stroking me. I was fully erect and the satiny fabric being dragged over my nipples and other private parts drove me wild. By this time my balls were felt swollen and ached in a way I hadn't experienced since my high school make out parties.

This went on until her hips began to undulate with the passion of her own climax. I was sure she would give in to my tongue and once again bathe my mouth with her juices. She had other plans however. At the last instant, she pulled away chiding me, "Not this way my precious, I want to feel you inside me this time."

She reversed her position so she was straddling my cock. She reached down and grasped my tool, holding in position while she slowly lowered herself onto me. I felt as though my cock was in a velvet vise as her moist heat enveloped it. She stopped only when I was completely inside her. She began to move her hips in a circular motion, grinding her clit against my pubic bone. Her breathing sharpened, coming in short pants and she began to raise and lower herself, at the same time clenching and unclenching her vaginal muscle.

It was obvious that she couldn't last much longer and as her climax neared she screamed, "All right, cum for me now! Fill my pussy with your hot oil!"

To emphasize the point she increased her tempo until we both fell into an abyss of ecstasy. My cock pumped for what seemed to be forever as my body released all the pent up pressure. I could feel our juices mingling, making everything even more slippery than before.

After what seemed an eternity, she collapsed against me, purring her pleasure. "That was incredible my pet. I felt as though I would explode from the intensity of it all." She kissed me softly and when her strength returned, untied me from the bed. "I don't know about you, but I have really worked up an appetite. I want you to put your pretty panties back on and we'll go down and eat something. I have a few ideas about where we will go from here that we can discuss while we eat."

Chapter Two

Once Helen untied me, I meekly stepped into my lace trimmed panties and slipped on my satiny robe. At Helen's direction, I followed her down to the meal she had postponed earlier.

"Sit, my pretty," she commanded, pulling out a chair. "The last thing I want is for my new pet to waste away from hunger. In fact, I think I'm going to put you on a regimen of diet and exercise, one that will enhance your girlish figure without sapping your energy."

Oddly enough, I found myself taking comfort in the idea that Helen was interested in continuing this relationship. The concept of being subservient appealed to me even more. I had always been the one to make the decisions and found it appealing to have this taken away from me. My role in our relationship would be the opposite of that at the office. There was no doubt in my mind that I would relish the idea of relinquishing all power to this captivating creature. As I ate the meal she had prepared, I wondered where she would lead me next. Helen's next statement confirmed that she was having the same thoughts.

"You realize of course, that you have reached a crossroads in your life. I want you to think about what has just transpired between us this evening. I believe you enjoy serving a strong willed woman. Furthermore, I think you would enjoy further exploring a submissive role. This is what I propose. While we are at work, we will continue to have the normal working relationship. There will be a few minor changes, but nothing that anyone except the two of us will know about. Once we are out of the office environment, I will be in charge. You will follow my directives immediately and without question. I will ask nothing of you that I don't think you really want and certainly nothing that will bring harm to you. If you accept this proposal, I will continue your training and lead you to delights you never knew existed. If you decline, I will never see you again, either at the office or socially." She reached over the table and took my hand before continuing, "Take a moment to think carefully, my pet and give me your answer."

I did just that, first thinking about how good the panties and the rest of my lingerie felt against my skin. I knew I had to accept. She had not really forced me to do anything I didn't really want to do. Nothing that had occurred had been in least bit unpleasant. On the contrary, as I have mentioned earlier, I was thrilled to be under her authority. Helen was about to open a whole new world to me and there was no way I could deny my urge to submit. I looked her directly in the eye and said, "I will do as you wish Helen. I want you to teach me about your world."

To my surprise she slapped me! Not hard mind you but with enough force to get my full attention. "When we are in this house, you will not address me by my given name. You will use either Mistress or Mistress Helen. Is that clearly understood?"

I was so startled, it took me a few seconds to stammer my reply, "Yes Mistress, I understand."

"Good, you may begin by repaying my hospitality. I want you to clear the table and rinse the china. You may then put everything in the dishwasher. When you are finished, I will continue your training."

I obeyed at once, being very careful with the china. I wondered where Helen was while I was doing my domestic chores. The answer to that came a minute later. I was startled by first a flash then the unmistakable sound of a Polaroid camera ejecting a picture.

"Why did you do that," I exclaimed? Remembering my prior instructions, I hastily added. , "I meant to say why did you do that Mistress?"

"First, I am proud of you for remembering the proper form of address for your Mistress," she replied. "As to your question, I took a picture of you simply because I felt like it. You must learn to never question me. Since you appear to be finished here, you will come with me. I'm afraid I will have to discipline you for your arrogance."

Helen turned on her heel and motioned me to follow. She led me back upstairs, but not to her bedroom. Instead, she continued down the hall to the room next to her own. Using a key hanging from a ribbon at her waist, she opened the door and ushered me in. It was another bedroom, one obviously intended for a girl. The bed was similar to Helen's in that it had a wrought iron frame work and canopy. The bedspread was pink satin with a matching ruffled flounce. Against the wall stood an old fashioned armoire and next to that a mirrored vanity. The opposite wall had two doors and as Helen saw me looking at them she explained, "One is a closet, the other is a connecting door to my room. That door will remain locked unless I decide otherwise. This is to be your room. This is where you will sleep unless I decide to allow you into your Mistress's bed. As you can see, the door can and will be locked. It is now time for you to get ready for bed. You will strip off all your clothes and place them in the hamper. You will find the hamper in the closet. While you are there, I want you to select a nightie for yourself. As I'm sure you're aware, a proper lady always wears something pretty to bed."

I followed her orders, stripping off my panties and bra. The corset was a problem. It took me several minutes reaching behind my back to untie and loosen the laces sufficiently to allow me to slide it off. I did eventually accomplish the task and set about inspecting the contents of the closet. There were only two nighties there, one in pink the other in pale blue. They were both a frilly baby doll design with matching ruffled panties. I chose the blue one. As I pulled it over my head, I couldn't help but marvel at how good it felt to be caressed by the soft nylon of the nightie. My nipples actually got hard as the sheer bodice cascaded over my chest. This was nothing compared to what happened when I slipped the panties up my legs. As they settled over my groin, my penis was teased by the slippery fabric, impelling it to erection. The panties were so sheer, there was no way I was going to be able to conceal my excitement from Helen. "Oh well," I thought. There was nothing I could do about that and went back to the bedroom for her approval of my choice.

"I told you to merely select your nightie" she chided. "I said nothing about your putting it on. I suppose I should have known this would happen. What you have done is prove just how much you like wearing panties. I've turned you into such an eager little tramp, you act without permission. "Come here," she ordered. "Let me see what it is that's making such a nasty bulge in your pretty blue panties."

I walked over to her and stood with my hands at my sides. She reached out and using just one manicured nail, traced the outline of my erection through the panties. "Would you look at the size of your clit?!' she exclaimed. "Whatever am I to do with you? There is no way I can just put you to bed like this. You wouldn't wait for the door to close before you started to play with yourself. I'm afraid I'll have to take steps to ensure that doesn't happen. I want you to go and lie on the bed, you know the position, so hurry up."

I did as I was told and as before found myself with my arms and legs secured to the bed posts, this time with one difference. Instead of the stockings, she used four leather cuffs with lengths of nylon rope attached. When she was satisfied that I was completely helpless, Helen looked down at me and smiled at my predicament. "Now I can sleep securely in the knowledge that my new sissy slave won't be able to get herself into trouble."

She reached into my panties and wrapped her hand around my erection. "If I left you to your own devices, you'd start to play with yourself, doing something like this," she teased as she began to slowly masturbate me.

My whole body spasmed, aching with desire. "Look at this," she said softly. "Look at how badly my sissy wants to come. Well, not tonight my pet, that is to be your punishment for not addressing me properly. In fact, you may as well come to understand that the only time you will be allowed any sort of physical release is when I deem it appropriate. That will happen only when I am satisfied that you are behaving properly and have truly earned the privilege. There will be times like now when it amuses me to tease and torment you without allowing you release. I have found this to me a wonderful discipline device. By the time I'm done with you tonight you'll always remember the proper way to speak to me."

She continued her stroking, asking in a husky whisper, "Don't you wish you had been a good girl? Don't you wish I'd tighten my grip and stroke you faster and faster until you filled your panties with your juices?"

"Yes Mistress," I panted. " Please Mistress, give me some relief, I'm very sorry, I'll never speak to you in that manner again."

"Not tonight my pet, perhaps in the morning if you are especially good, I'll let you climax. For now though, I'm afraid I'll have to continue your torment until I'm satisfied that you have truly learned a lesson."

True to her word, she continued. Each time she felt me getting close to the precipice, she either slowed or stopped stroking me completely. My hips would buck involuntarily, striving to get release from my heightened arousal. This went on for several minutes before she removed her hand and pulled my panties back in place.

"Don't go away," she teased as she went into her room, returning with a pair of black lace panties and her Polaroid camera. "First, I'm going to document your submission to me," she said as she took several shots of my helpless situation. "My possession of these pictures will ensure that you don't have any second thoughts about obeying me. Can you imagine the thrill the other secretaries would get out of these if I posted them in the ladies room?" I imagine they'd be quite jealous. I doubt any of them have a lingerie collection as vast as the one I have in mind for you."

Helen waited a few minutes for the prints to develop before showing them to me. There was not a doubt in my mind that these pictures could ruin my career. They clearly showed me in tight bondage while wearing pretty lingerie. One shot in particular, showed my cock straining against my panties, proving how much I enjoyed my imprisonment. "

"Just one more pose and I'll leave you to your dreams," she continued. "I want you to be reminded of me while you sleep tonight," she said pulling the black panties over my head. Once they were on, she arranged them so the crotch area was directly over my nose and mouth. Then, using a common safety pin, she took all the slack out of the waistband and secured them at my neck. I was now trapped inside her panties, forced to inhale a combination of her own sweet musk and the perfume she wore.

"I hope you appreciate these. I wore them at the office today and they are full of my scent. Now each breath you take will be a reminder of your Mistress and her sweet pussy. Unfortunately, that is as close as you'll get. You have misbehaved and as much as it pains me, I have to instill some discipline."

After taking more pictures of me, she turned and walked to the connecting door, calling over her shoulder as she went, "Sweet dreams little sissy, I'm tired and have to get some rest. You must be tired as well and you'll need your beauty sleep. I have a big weekend planned for you."

The door was then closed and I heard the distinct sound of the lock being thrown. My erection continued to throb, causing me great discomfort. How, I wondered could something normally so pleasurable be so uncomfortable? I tested my bonds, hoping Helen had left enough slack for me to get to my aching tool. Of course there wasn't any to be had. I reconciled myself to the fact that I would just have to try and go to sleep, that I was now alone, trapped until Helen decided to release me. Needless to say, sleep came very hard. The panty hood ensured that with every breath, I was filled with her essence. My erection was still there as I drifted off to sleep.

I awoke in the morning to the sound of Mistress's voice, "Come on, sleepy head, it's time for you to get up." I opened my eyes and through the thin nylon of my panty hood, I saw Helen standing next to the bed. She was dressed, if you want to call it that in a pink half cup bra with a matching garter belt and seamed stockings.

"I told you I was going to put you on an exercise regimen," she said as she undid the safety pin holding my hood in place. She continued speaking as she pulled her panties off my head, "We may as well begin now. Your tummy needs to be tightened and I can't think of a better way than with a few sit-ups. These are going to be very special sit-ups. You are going to have the privilege of servicing your Mistress while you exercise."

I wondered what she meant by that. How was I going to do sit-ups and pleasure her at the same time? My question was answered in short order.

Reaching into the drawer of the night stand, she retrieved two items. The first was a sturdy leather collar with several rings attached. Helen place it around my neck and secured it with a small padlock. She then untied the rope holding my wrists to the headboard and reattached them to the collar. Next, she picked up what appeared to be a dildo with two latex straps. Placing the base of the dildo against my chin, she stretched the straps over my head. One went around my neck, the other over my ears to the back of my head. When she was finished, I had a six inch latex cock growing out of my chin.

"Now my pretty, you are going to please me while you tighten your tummy," she said as she straddled my face, while facing my feet. She lowered herself until the head of the dildo was just at the entrance to her pussy. "Now I want you to stroke it in and out of my pussy very slowly," she ordered. "At the top of each stroke, you are to lick my ass, swirling your tongue around my rosebud."

I hesitated for just a few seconds, not sure what she meant. This prompted Helen to reach into my panties and lightly squeeze my balls. "Get to work sissy, I don't have all day!"

I immediately complied, using my stomach muscles to raise my head, driving the dildo deep inside her love tunnel. As she had dictated, I used my tongue to bathe her ass, swirling it around and trying to stick it inside. In order to do this, I had to hold myself in position with just my abdominal muscles, putting considerable strain on them. By about the fifth repetition of this, Helen began to breathe heavily, bathing me with her juices. Before long, Helen gasped, "All right my pet, rest for a minute. I want to change position so your talented tongue can be put to better use."

I stopped at once, grateful for the chance to rest. Helen repositioned herself so her pussy was facing me and after a short interval, again lowered herself to the dildo. "All right, I'm sure you know what I want at that top of each stroke," she whispered. "Give me some pleasure and I just might let you up."

I repeated my prior performance, the only difference being this time I used my tongue on her clit. Her body began to tremble as the onset of her climax approached. I used this to my advantage, holding myself with the dildo deep inside her while I sucked her clit between my lips and lashed it with my tongue. This was more than my Mistress could stand. Her orgasm overtook her and she screamed her pleasure. "OH YES MY PANTY PET, SUCK ME, FUCK ME, MAKE ME CUM."

She ground her clit against my mouth, filling it with her pleasure honey. Her climax would begin to abate then another wave of pleasure would shoot through her, until at last she collapsed, resting against the headboard.

It took several minutes for Helen to regain her composure. Only when her respiration began to return to normal did she lift herself from the dildo. She sat next to my still bound form and while stroking my cheek said, "That was incredible my pet. The feeling of being penetrated and attended to orally at the same time pushed me to heights I've never reached before. This is the first opportunity I've had to use this toy and I can assure you, it won't be the last."

She unlocked the collar and removed the cuffs. "I want you to take a bath now. I have it prepared and to make sure you don't do anything naughty, I will accompany you."

With that statement all hopes of being allowed to relieve the pressure in my groin vanished. Helen was apparently intent on keeping me at a high state of arousal for the foreseeable future.

I stood and undressed, placing my baby doll nighty in the closet hamper. I followed Mistress Helen into the bathroom where a tub was already filled with hot, scented water.

"Get in, sissy we don't have all day," she ordered.

I did as I was told, slowly immersing myself in the water. I began to wash, using the sponge handed to me by Mistress Helen. She next gave me a pink razor saying, "Now shave yourself all over. I don't want to see any regrowth from last nights shaving. I know I did it for you last night but I want you to learn how to do this for yourself."

Again, I followed her instructions, now without even so much as a second thought. While I shaved, I marveled at how much my life had changed in just a few short hours. This time yesterday, I was a typical single male, looking only for my own pleasure. I recognized the fact that now everything had changed. I was now just the play toy of a beautiful woman, trapped forever in her web of silk, satin and lace. What was even more interesting and in fact more to the point was that I was enjoying it! I found myself looking forward to the events to come. The questions I asked myself included; What would Mistress Helen dress me in when my bath was over? What color would she choose? Would I be allowed to wear a corset again? All these thoughts and more occupied my mind as I finished the last of my shaving.

My reverie was interrupted by Helen's next command. "All right my pet, it's time to get out of that tub. We don't want our pretty skin to get all wrinkled do we?"

I rose and stepped into the soft bath sheet she held and stood docilely as she patted me dry. "Come with me," she said, leading me back into what I had begun to think of as "my room." Once there, she had me sit, still wrapped in the towel at the vanity.

"You have such pretty features, I think a little enhancement would really bring out your natural beauty," she purred.

With that, she set about giving my face a more feminine appearance. She plucked my eyebrows, applied mascara and eyeliner. Next, came the foundation and a little blush for my cheeks. The last thing applied was the lipstick, a bright crimson. She stood back, admiring her handiwork in the vanity mirror. "There's just one thing missing," she mused. "You need a more lady like hairstyle. You are such a lucky girl, I have just the thing."

She left the room for just a moment, returning with a large round box. "Close your eyes my pet, I have a surprise for you."

I closed my eyes in anticipation of what she had in store for me. I was sure by the size and form of the box that it would be a wig. My suspicions were confirmed when I felt Helen placed it on my head. She fussed with it for a moment, combing it into place. "All right, you may open your eyes now," she instructed.

I opened my eyes and gazed at the creature in the mirror. The image was of a striking woman, one with shoulder length auburn hair. There was one thing that struck me immediately and I had to ask, "Mistress, the color is an exact match for my own hair and coloring. Is that a coincidence?"

"Of course not, my pet, I bought this several weeks ago in anticipation of this very moment. Once I was sure you were the one I wanted to undergo my special training, I took a chance that I could make this happen." She reached down, trailing her fingers down my chest to the top of the towel. "Stand up now pet, it's time to get you dressed."

I followed her to the armoire where she opened several drawers. In each was an array of panties, bras, stockings and garter belts. There had to be at least a dozen sets there, all color coordinated.

"Hmmm," she mused as she inspected them. "Which color would be most appropriate for your first full day as my panty pet? Let's see, since you are almost newly arisen to the realm of panties, I think virginal white will be perfect."

She handed me a complete set of lacy, white lingerie, indicating that I was to put it on. I took the stockings and rolling them first, pulled each in turn up my legs. Next of course, came the garter belt. This was quickly followed by the bra and panties. The bra was under-wired with push up pads sewn into the cups. Once in place, I once again had the illusion of small breasts. The panties were French cut, with lavish lace at the leg openings and side panels. I walked to the vanity so I could inspect myself in the mirror.

From behind me I heard Mistress Helen issue yet another order, "Go to the closet my pet, there's a dress that will be perfect. You will also find a pair of white pumps that should fit you."

In the closet I found the dress and shoes she had referred to. The dress was a white jersey knit, the kind that would cling to the body. The shoes were also white with a pink bow at the instep. I pulled the dress over my head and pulled it into place. The hem came only to the tops of my stockings. When I slipped the shoes on, the problem became even more pronounced, clearly showing the garter tabs.

Helen had come up behind me and her laughing voice interrupted my struggles to get the hem lower. "I didn't think it was possible for anyone to look like such a tramp while wearing a virginal white dress. What a pity you can't show yourself off to the world like that. You'd give a eunuch a hard on with that outfit! Wait a minute! Why not? You look quite convincing. If I hadn't dressed you myself, I would never know there's a cock in those panties. I think we're going to take you out like that. I had intended to take you shopping anyway, so we may as well make the best of it."

"Please, Mistress, don't make me do that," I cried. What if we meet someone I know, or worse yet someone we both work with?"

"Not to worry, my pet. I know of an absolutely fabulous shopping mall that's about a two hour drive from here. There will be little chance of us running into anyone we know there. Besides," she continued as she handed me a pair of wrap around sunglasses, "these will serve to disguise you further. Enough of your back talk, be a good girl and do as you're told and perhaps your Mistress will give you a special treat when we get back. Come along now, we have some shopping to do."

With that said she turned on her heel and headed for the front door. "We'll take your car, my pet. That way your hands will be occupied and you won't be able to get into any mischief the way you could if I were to drive."

She stood at the side of the car and watched with amusement as I attempted to get in the driver's seat. "Not that way silly," she taunted. "The way your dress rode up, I could clearly see your pretty white panties. No lady would ever allow that. Get out of the car and I'll show you the proper way to enter a car while wearing a dress."

Mutely, I obeyed and watched as Helen showed me the proper procedure. She sat on the seat, facing out with her legs together. Helen then kept her knees together and holding the hem of her dress down, pivoted on the seat, swinging her legs into the car. "Now, you will demonstrate for me," she said as she reversed the process to get out.

I was able to mimic her motions fairly well, but she still insisted I do it several times until at last she was satisfied that I had it mastered.

"Now take us to the freeway and head north," she ordered. "I'll give you directions from there."

For the next hour and a half, my mind was kept busy with just the chore of learning to drive while wearing heels. As we approached the outskirts of the next large city to our own, Mistress Helen told me to take the next exit. From the bottom of the ramp, I could see the mall she had in mind. Without being told to do so, I drove into the large parking lot, managing to find a spot fairly near the mall entrance.

Helen got out first, coming to my side to see if I had truly learned how to exit a car gracefully. As I did, she clapped her hands to show her approval. "That's much better my pet. Come with me, we have some serious shopping to do."

The rest of the afternoon was a blur of shops. First, we went into an upscale lingerie store. We spent considerable time picking out panties, bras, garter belts, stockings and several pretty nighties. The styles ranged from demure to naughtiest of crotchless panties and open cup bras. Helen took great delight in holding these most feminine of garments against me while she oohed and aahed about how good they would look on me. All the while she did this, she wore an incredibly mischievous grin. At one point as we were looking at several full length nightgowns, she made me hold a lacy lemon yellow number against myself while she stood back to get the full view. I saw the clerk smirking in our direction, a knowing look on her face. I was mortified to say the least. Helen thought this to be hilarious, and made several more remarks about how hot I'd look in some of the more risque choices.

By the time we had made all our selections Helen paid for them with her gold card, teasing me in front of the sales clerk. "What sort of woman goes shopping and leaves her purse home, you're such a ninny. It's a good thing you have me to take care of you."

As we left the lingerie boutique, I could feel how aroused my panty trapped cock had become. Helen noticed this and whispered in my ear, "You certainly seem to be enjoying yourself my pet. Try to contain yourself though, we don't want any nasty bulges giving away what you keep in your pretty panties, do we?"

I whispered back, "I'm sorry Mistress, but this is getting me excited. I don't know what I can do."

"As usual, your Mistress has the solution," she replied. "Come with me, and we'll powder your nose."

She led me into the ladies restroom. Thankfully, it was empty, leaving us alone. She led me to the furthest stall and once inside, latched the door.

"I must accept part of the blame for this, she said. "I should have known how excited you were and taken care of this before we left the house. Pull your dress up for me pet, and Mistress will try to do something about your problem."

I pulled the hem of my dress to my waist, exposing my panties. Helen pulled them off, commenting as she did so, "I'm glad you had the foresight to put your panties on over your garters. It makes it so much easier to get them off."

Once they were off, she wrapped them around my cock and began to stroke it. In no time at all, the beginnings of my climax shook my body, causing my legs to tremble.

"All right my pet, let your Mistress do all the work," she whispered. "You have my permission to cum now. Fill your panties for me."

To ensure my compliance, she reached down with her free hand and cupped my swollen balls, massaging them gently. My cock erupted, filling the silky panties with juices. When she was satisfied that she had milked the last drop from me, she used a tissue to wipe the last of it away. She took a new pair from the bag and after removing the tags handed them to me. "Here put these on. It's a good thing we bought a new white pair or you'd have to go without for the rest of the day."

I put on the clean panties and pulled my dress down. Helen led me from the restroom, depositing my soiled panties in the trash can at the door.

We finished our shopping with stops at a shoe store and dress shop. We bought only two dresses and three pairs of shoes there. By the time we were finished, it was late afternoon and time to go home.

As we walked to the car, I commented, "Mistress, we seem to have purchased an awful lot of lingerie, but not much in the way of dresses or other outer wear."

"You won't be going out that much just yet, my pet. You will however have to wear your pretties any time you are with me. That's why you need so many."

"But Mistress," I stammered. "What about when we're at work?"

"I should think it obvious that since you are with me at work, you will wear your pretties under your suit," she replied frostily. "Even though to the people at the office, you are my boss, we know better, don't we? Your panties and whatever else I decide to dress you in will be a constant reminder that you belong to me. You really have no choice in the matter. I'm sure you remember the pictures I took last night and what will happen if you disobey me."

She then changed the subject, asking, "Are you as famished as I am my pet? That's a silly question of course. You must be starved! I know how much shopping can tire a girl out, lets stop at a little restaurant I know on the way home."

Dutifully, I got in the car and began the drive home. About half way there, Mistress directed me off the freeway. After a short drive, we were at the restaurant where we were immediately seated.

Helen ordered for both of us. We both were going to have the Chef's Salad with oil and vinegar dressing. "A girl needs to watch her figure and you're no exception," she explained. I felt as though every eye in the place was on me, that everyone there knew I was really a man in women's clothing. Helen dismissed those thought, explaining that perhaps the only reason people were staring was that I had not taken off my sunglasses. I still didn't take them off, figuring it was better to be stared at than recognized.

After the light lunch, Helen had me detour slightly to a store devoted to sex toys. She made me stay in the car while she went inside, returning ten minutes later with a bag of what she referred to as her training toys. She wouldn't elaborate, simply saying I would find out what she had bought when the time was right.

There was silence as we drove back to Helen's. As we pulled into the drive, she told me to bring all the packages up to my bedroom. Once everything was in, she spoke, "Take off your clothes and take a quick shower. Then we're going to have a fashion show, I want to make sure everything fits."

The next few hours were a blur of soft, silky fabrics in every style and color imaginable. Helen made me strut and pose in each ensemble, making comments on each one. She was especially partial to the last outfit she had me wear. It was purple with lavish black lace. The bra had black lace trimmed holes where the nipples were and the panties had a zipper from front to back. The possibilities of this outfit were immediately apparent.

Helen took note of my apprehension while wearing it. "Don't worry my pet, there will be times that I want you to be able to wear your pretties without denying me access to every part of you. When the zipper is closed, you will have your modesty, but when I open it, I will be able to tease and use any part of you I want. You will be completely exposed and vulnerable, even though you have a complete set of lingerie on. The other advantage is you don't have to bother putting the garter straps under the panties. I hope you appreciate all the trouble I go to in making you comfortable."

"Oh yes, Mistress, I certainly do," I replied.

"Well in that event, I'm going to allow you to prove it," was her response.

She went to the closet and got a spare pillow. Placing it in the middle of my bed, she commanded, "Put on your wrist and ankle cuffs and lie on your back with your cute little ass on the pillow."

I did as I was ordered and once again found myself bound to the bed. The big difference this time was my hips were supported by the pillow, forcing my crotch up.

Helen stripped off her clothes and naked came over to where I lay. She began to lightly trace the zipper with a finger tip until she reached the rosebud of my ass. Pressing lightly against it she said, "The time is coming when you will have your virginity taken. Because I care about you, I'm going to do something that is practiced by an obscure South Pacific tribe. When a girl is about to be married, the other women of the tribe use a series of wooden dildos to prepare the maiden for her marriage bed. In this manner the girl gets the unpleasantness of defloration out of the way and is able to fully enjoy the first time she is taken by her husband. I am going to prepare you in much the same manner. Beginning tonight, you will have a plug inserted. The first one will be quite small, the next a little larger and so on until you are completely ready for the ultimate moment in a girl's life."

She went to the bag from the sex toy store and came back with a small butt plug. It was about two inches long and one inch in diameter at the widest point. It had a base to prevent it from getting lost inside and an indentation to prevent it from being easily expelled.

Helen pulled the zipper in my panties all the way down, exposing my cock and ass to her gaze. She took a tube of lubricant and began to coat my ass with it. She coated the butt plug and placed it at my opening, saying, "relax my pet, this is for the best. Soon you'll crave the feeling of having your pussy filled."

I felt her increase the pressure against my ass and began to do as she instructed, relaxing my sphincter muscle. I could feel her inching it inside, the discomfort growing until it passed the widest point and she drove it all the way in. Uncomfortable at first, I soon started to get a feeling of arousal as my body got used to it. This was evident by my penis, which while it was flaccid at first, soon grew as the sensation of pleasure chased away the ache.

"There my pet," she teased. "Doesn't that feel better? Not that what you want is of paramount importance, but it would be nice if you could learn to enjoy the inevitable. I'm afraid you're going to have to sleep with it inside you tonight. By morning, you'll be ready for the next size. By tomorrow night, you'll be ready to become a woman. For now though, I'm going to require that you service your Mistress with your clit. All this shopping and watching you prance around in your dainties has gotten me quite aroused. I think that since you are the cause of my problem, you should be part of the solution."

Click here to go to the conclusion of the story in part two