Disclaimer- This story contains some description of situations that should not be read by minors. All those depicted in this story are fictional, as are the situations. Any resemblance to any person living or dead is entirely coincidental. Any comments on the value of this story will be welcomed, but only if they are constructive. Send comments to tbrscd@icqmail.com Thank You, and enjoy, -Tiberius.
Male Mistress (pt 1)
"Tell you what, Collin. As we couldn't meet last week, and this week I'm a bit busy, why don't you meet me at my parent's house. I have to clean it up and it'll be private so we can talk about what you need to do to make more money here."
"Alright Richard, that sounds fine. When and where?" And with that innocent sounding phrase, I started along an adventure.
It was Wednesday afternoon when I pulled up to a relatively secluded ranch home in a nice middle income community. Richard was in the driveway waiting for me and he lead me into the home. Within was a barely furnished, but well lived in house. I asked why it was like this.
"You see, Collin, my mother died earlier this summer and left this house to my sisters and I. We children came to an agreement in which I took possession of the house while they got most of the rest of the things."
"Oh.. I'm sorry bout your mother. What do you intend to do with the house?"
"Well actually, that's what you are here for."
"Huh?" I eloquently replied as he gestured to a chair for me to sit across from him.
"Well, I guess you didn't know this, but I routinely check out the computer at the office, and I was able to read a story that you had written. As a result, I felt able to put this proposition to you."
I was nervous. There was only one kind of story that I wrote. I paled visibly and waited to hear what he had to say... thinking to myself for some way to explain my way out of this.
"What I want to know is if you will... well you see, my wife isn't all that I wanted in this world. I've always wanted something different. Something new and exciting you might even say. Well, in essence I've always wanted what you wrote of in the story. A man dressed up like a woman."
My mouth just worked. I didn't know what to say. Half of me wanted to deny every allegation, while the other half was finally relieved that the hiding was once again over. He rushed on with his explanation.
"I will offer you whatever you find reasonable, but I thought that I could offer you this house for you to use, free of charge while we're... well... together. Plus whatever else, within reason, you can come up with.."
"I really don't know what to say... I mean, this has never happened to me before. Do you think maybe I could get paid for this in some way that we could disguise it for the IRS or something?"
"Sure. I have a friend at a payroll service. He can take the money from me, and disburse it to you as if you were an employee of mine and I didn't want the hassle of the paperwork. He pays all the taxes from what I pay him and you get the checks."
"And what exactly do you want from me?"
"You will be here at this house in time to dress up every weekday in feminine clothing by twelve o'clock. You will then stay this way until seven o'clock. If I haven't come by that time, you may do whatever you like. All other times you are on your own. Whenever I am able, I will come here from work for a quickie at lunch, or for dinner after work. Since I do have a family at home I will rarely, but sometimes stay here. On the nights when I am able to sleep here, you will stay here with me. You get the picture? If you want to quit your job as night watchman for the office, I won't mind. I'll roll that into your new pay schedule."
"I understand. What I want, then, is fourteen hundred dollars a week take home and an expense account, whether it be a credit card or cash disbursements, to purchase more clothing. I am sure what clothing I do have is inadequate to what you want in a kept woman."
"Would a credit card with a twelve hundred dollar limit, billed to me, but made out to your female name be adequate?"
"That'll be just fine. Though, I may need more this first month to get some initial items."
He responded to this in a way I didn't expect. Out of his pocket he pulled a wad of cash, he counted out a thousand dollars in hundreds and tossed it down to the table between us. Then, looking me in the eye asked, "That enough?"
I just nodded dumbly.
"Very well. I find your demand for your salary also acceptable. So then. Is it a deal?"
I stood up, walked around the table and held out my hand. "You can consider me your girl Friday."
He stood, took my hand and smiled. "Let's consummate this deal properly."
He led me down a hallway and into the master bedroom. There was no furniture in the room, but there was a mattress on the floor. Pulling me into his arms, he looked down into my face and pulled me close. I looked up and meekly accepted his lips on mine. I felt his cock get hard between us. When he broke the kiss, he began to unbuckle my pants. I helped him slowly undress me and, at his insistence, I knelt on the mattress.
Behind me, he rolled a condom over his long, hard cock and lathered it up with lubricant. Sliding the nozzle of the lube into my ass, he gave it a squirt. The coldness of the lube startled me, but soon it was replaced by the head of his cock bumping into my sphincter. With a slow steady push, he pressed himself inward and down to the root.. My breath was stolen from me when he finally reached his full depth. He waited a bare moment for me to adjust, but then began a rapid withdrawal until almost removed followed by a thrust inward until he was once more within me to the root of his cock.
I just closed my eyes and held on for the ride, getting what pleasure I could from the feel of his cock pistoning in and out of my ass. I must admit I came bare moments before he did. When he finished, and pulled out, I fell to the mattress and lay there gasping. Turning my head I saw him button up his pants and readjust his shirt.
"So then it's a deal," he remarked lamely. "I'll have a little more furniture in here by next Wednesday. The Monday after that I expect you to be as fully moved in as you need for you to fulfill your part of the bargain. You don't have to but, if you wish, you may live here full time. Give up any apartment or whatever you may have. You can start purchasing the stuff you want with the cash in the living room, I'll have the card for you by Monday next, and here are your keys and garage door opener." He dropped a bundle on the floor by me. "It's your house. Do what you want and let yourself out whenever you would like. See you Monday."
After visiting the master bath to clean myself as best I could I returned to the bedroom to dress once more. Then before leaving I gathered up the thousand dollars. I locked up the house and drove home in a daze, wondering what exactly my cock had gotten me into.
All that next week I gathered up all the feminine clothing I had accumulated for myself and packed it away in boxes. When Thursday finally came, I brought it all over. Letting myself into the house through the garage, I found myself in a new place. The house had been given a facelift. Where it used to be a well lived in, but old, home, it had now become an obvious bachelorette pad. New wallpaper and rugs, furniture and fixtures all pointed at a wealthy but single woman. The master bedroom was dominated by a new four posted canopy bed and very feminine furniture. I could only smile and begin unpacking.
Once unpacked, I realized suddenly just how meager my supply of feminine things actually was. The drawers of my dresser were very empty, and the closet echoed. The shoe rack was decidedly barren. I decided that would become my next order of business.
Setting my second computer up in my new office, I hooked it up to the phone line and connected to the internet. I already had many catalogs and had chosen out many things that would fit me and might arouse Richard, but internet ordering, I realized, would be faster and would get me a good selection to start with until the rest of the things I ordered would come in.
After finally clicking the 'send info' button for the last time, I shut down the computer and gave myself a formal tour of the house. Starting back at the Mistress' suite, I looked into the bathroom. Large whirlpool bath, stand up shower, water closet and counter-top with vanity and make-up mirror.
I smiled to myself in the mirror and moved on. The very ample walk in closet was attached to both the bath and the main room. I looked at the expanse of clothes rod and shelving and thought to myself how much fun it would be to fill this closet. Then I proceeded on once more.
The master bedroom was roomy, but not too large to be comfortable. From there, the doorway led out into the ranch style home's center hallway. The first room on the right was the study/sewing room facing to the front of the house. The left was the office. Then further down the hall the right had the living room and the back had the dining area. All that remained was the kitchen at the rear of the house, and the family room with entry to the front. And between them the exit to the garage and the laundry between the house and the garage.
All in all, a very nice home.
Returning to my bedroom, I began to undress. I had planned for this day for the past week, and had informed mom that I had a vacation planned. I wasn't expected home until Monday evening. I had five whole days to myself, and no one to care how I looked during them. I decided I was going to get into shape to give Richard a great welcome when he met me Monday. He wanted a feminine me, and I was going to give him the best possible me in drag as I could.
Once I was undressed and had my male clothing properly thrown away into the clothes hamper, I pulled a soft robe around my torso and made my way to the bathroom. I gathered my toiletries, and sat myself in my bathtub and arrayed my implements. After dropping the robe off my body, I began the arduous task of depilating myself. As I knew there was no way to stay smooth long by shaving, I decided I would have to wax.
My god, what a horrendous thing we women have to do for beauty. It hurt like a bitch, but when I finally finished I was quite hairless.
I quickly ran myself a hot relaxing bath with skin softening oils and bubbles. I lit the candles I had brought and eased myself into the warmth to relax and soothe the soreness caused by the waxing. I spent quite a while just sitting there, inhaling the fragrance from the oils, the candles and the soap. When it was finally time to get washing, I gathered my body wash and my wash puff and stood out of the water.
The shine of my wet hairless body was quite sexy looking and very convincingly feminine. I admired briefly, but then continued with my cleaning.
I let the water drain out of the tub, and squeezed the body wash liquid into my scrub puff. After thoroughly lathering up, I stepped into the shower and rinsed off. Then I proceeded to wash my hair.
Again I was glad that I had allowed my hair to grow long. It would be easier this way to style it, and look more convincingly female. Wigs were such a poor solution, and I didn't want to look fake for Richard.
When I had finally finished, I stepped out and slowly patted myself dry. Then, wrapping my hair up turban like, I slid back into my robe and returned to my bedroom. I sat at my vanity and took up my fake breasts. Preparing them and my chest, I pressed them firmly on, adjusting them slightly, and waited for them to hold. Once on firmly, I took up the bra I had set aside and slid it on, fastening it behind me with a well practiced motion. Then, pulling up my robe again, I proceeded to work on my face.
I had been playing with make-up for quite a while, but luckily just the past month I had ordered from a transvestite website a video on make-up application. Now I felt I was getting quite adept at it. A little base to even out my complexion, some eyeliner and mascara and a little lipstick all contributed to changing my face even more. The final touch was when I took down my hair once more, brushed it out and styled it. A little mousse for volume and some aqua net for hold and I was once again Rebecca.
I got up then and shrugged out of my robe and slid on my gaff. Once more sure that my little friend would be tucked away perfectly, I wrapped my corset about my waist. I tugged myself into a more hourglass shape, glad that I had started dieting so I would not have to do this much longer. Then, looking more like the woman I sometimes wished I had been born, I dressed in the casual clothes I had chosen for the big first I had planned for today.
First I drew the suntan stockings I had chosen to wear up my now smooth legs. I attached them to the garters hanging from my corset, then I pulled a pair of panties over the garters to finish my underwear. Next came the white blouse and the black denim skirt with a vest to cover them both. A belt to accent the outfit, and black loafers with a three inch heel finished the outfit suitably. After transferring my wallet contents to my purse and painting my nails I was ready for the most daring part of my day.
I was going out shopping.
Even though I had been dressing like this all my life, mostly, I had never had the guts to go outside when anyone could ever possibly recognize me. But this was different. I had been really practicing, and think I would do well. Today I was going to go whole hawg one might say. Besides, there was still a lot of stuff that this house needed that I could have gotten over the internet, but I needed them before they ever could have gotten here. Besides the obvious food concerns, I also needed household things. Towels, sheets, and all the other little things that a home needed.
I snatched up my keys and went out to the garage, started the car up, and without a second thought, drove out to do my stuff.
It was great.
I cruised the mall, going to all those places that I as a man would have gotten funny looks and for the most part, no one really noticed or cared that I was a man. In sears I got a funny look or two, but dammit, I still like tools. And I assuaged the clerk's curiosity by buying the pink ladies tool set.
Hell, it was such a great day that I even bought myself a new outfit for Richard when he came to see me on Monday, and even got my ears pierced. I felt it about time.
When I finally got home, I was exhausted, and was barely able to put my purchases away, and make my new bed with the purchased bedding, before I had to change into my new nightie and go to sleep.
The next day I got up early, and dressing in exercise stuff, went into my family room. Putting one of my new exercise tapes into the VCR, I worked out for an hour. Then, after a quick shower, I was dressed in casuals and having breakfast. Wondering what to do today, I had a funny thought. It went so well yesterday, I decided I had to go malling one more time. I changed once again into an outfit much like what I had on yesterday, and out I went. This time I waved to my neighbors as I passed. They would all get to know their new neighbor soon enough, there was no point in hiding.
As I walked through the mall, my hair swinging in a ponytail behind me, I watched the reaction I got from those around me. The women appraised me, and the men generally looked on in interest. I know I was not the best looker in the place, but I did look like I wanted to be noticed and the men, true to nature, obliged. I felt good. I bought a few more clothes, and household items, but really hadn't treated myself when I noticed that no one was waiting in the front of the beauty salon. I just had to try out my new femininity, so I went in.
I was greeted cheerily by a teen aged receptionist and told there was no wait just then for a hair appointment, and yes, I could have my nails done as well. It was wonderful sitting in the chair being waited upon and becoming more beautiful by the moment. It took a while, but I left much more beautiful than when I entered. I couldn't wait for my Richard to see me.
When I finally got home, I was excited, and quite a little turned on. I needed to do something, but I didn't quite know what I wanted to do. While I tried to figure it out, I decided to eat. I looked around for the groceries I meant to buy today... and alas I didn't have them. I had to order out. I decided that a greek salad from the pizza shop down the road would be great. I called and ordered it, with a diet pepsi, for delivery. Then, sitting down in my family room, I turned on the television.
There was nothing on the television, and I could not keep my mind off how sexy I felt right then. I was the most female I had ever felt, and I needed to show it off for someone. I was deep in thought about this when the doorbell rang. Flustered I went to the door and met the delivery boy. He was maybe eighteen, and dressed in a tight pair of jeans and tee shirt. Naughty thoughts came to mind. I asked him in on the pretense of getting my purse. Once I had the door shut behind him, however, things changed.
I had him put the food down, and proceeded to 'look for my money'. I had enough to cover it, but I pretended I didn't have anything. When the poor boy tried to be kind and offer to just get it the next time, I told him nonsense. I had a way of paying him.
I strode, slowly, sexily, up to him and kissed him deliberately. This kid was no idiot, he knew what the score was. It was a bare half second before he was tongue wrestling with me and grasping at my ass and breasts. I was getting into this, and it was with a huge force of will that I pushed him away. Not understanding my move, he began sputtering apologies. I stopped him with a finger to the lips. Then I knelt before him, and unzipped his fly. In no time, I had his cock out standing proud before my face.
I had never sucked a cock before, but I knew I would have to for my Richard and decided I had to practice sometime. Now was as good as any. With one hand, I grasped the base and brought my lips to the head. The first taste of the pre-come coming out was interesting. I loved running my tongue over the tip, gathering up the drops accumulating there.
Getting used to this, I began to suck him deeper into my mouth, while stroking softly at the little bit uncovered by my mouth. I pulled off his cock when I reached the back of my mouth and licked up and down his shaft, peering up to his face. He was obviously enjoying this, so I took him in my mouth again. Each time I took him into my mouth, I pressed him deeper into me. When I thought I might gag, I swallowed and fought off the reflex. In minutes I had his whole cock in my mouth, and I had my nose pressed into his musky smelling pubic hair. Once I had him fully in my throat, I began massaging his testicles and sliding him fully in and out of my mouth, like I was allowing him to fuck my face. By his groans, I knew I was doing it right. It wasn't long before he clamped his hands over my head, pulled me tight to him, and came into my throat. I just swallowed every pulse until he let me up.
When he finished, I kissed him once more, tucked his cock away, and led him to the door. I told him that the next time he delivered here, he could expect the same tip if he told no one else. He just nodded dumbly and staggered off to his car.
I smiled to myself as I sat down to eat my supper and finish watching the television.
Saturday morning, after my new exercise regime was finished, I began practicing my voice and the rest of my female deportment. With the new long nails I got at the salon the day before, practice was needed. I never thought they were so difficult, but in no time, I felt I had it. It was the same way when I first put on heels. In a few hours, It was as if I had always been wearing them. Now I am just as comfortable with them on as not. I even taught myself to dance in them.
When I felt my voice was getting correct, I went back online and began shopping some more. A school girl outfit.. Richard would like that someday... After a few hours and many dollars, I was then bored with that as well. I didn't want to go shopping at the mall again. I guess I needed food, I'd have to go grocery shopping.
I spent the rest of the day doing just that and putting all the things away later, when I got home. I went to bed early that night and just read myself to sleep. Erotic romance novels of course.
Sunday I got up late and made myself a good breakfast. Since it was a nice day out, I decided it was high time I went out on my deck and sunned myself. After donning my bathing suit, two piece of course, I went out and laid down upon my chaise lounge. I had been there a few hours, and had just turned over on my back when a voice near my face asked me a question.
"Hi. I'm Sandy, your next door neighbor. Do you need lotion on your back?"
Startled I jumped up, but soon I calmed down enough to look around and saw this teen girl standing in front of me, just off the deck.
"Oh, you startled me. Hi Sandy, that would be nice. Do you want to join me?" I noticed she was attired much the same as I was, and eagerly she bobbed her head in the affirmative to my question. I pulled another deck chair over beside mine, and then proceeded to just purr as her small hands massaged lotion onto my back. She was good. All too soon, however, it ended and it was my turn. I did a thorough job and we laid down once more facing each other so that we could talk.
She told me that there was no one who understood her, her parents hated her and she had few friends. She said how nice it was for me to let her come over. I decided that I liked her, the way she spoke, she sounded intelligent, and though her body was growing out quite nicely, she had a very plain-jane, bespectacled face. After hearing that she had to wear uniforms to school, though I briefly had to arrange my little friend, I knew why she didn't have boys sniffing around her. Unless you are some incredible looker, or really stacked, a girl in a private school uniform is uninteresting to the boys who see them all everyday. And besides, there was also a public school in the area for the boys to get girls who dressed as sexily as they wished. This poor girl would never get her chance until later, but then, it would be a great day.
We talked for quite a while, until dinnertime, and she stood, remarking that she had to go home. I told her to come back anytime. Just knock, and if the door was open, come right in. She dimpled, waved, and trotted off back home. I admired her ass.
When she was around the corner, I got up myself and went inside to start preparing for the big day tomorrow. Basically, I bathed, shaved what little hair was still above skin level and settled in for an early night, alarm set for early next morning.
The next morning I awoke to the annoying sound of the alarm clock. Groaning at the early hour, I slapped the alarm off, and slowly got to my feet. Into the bath to relieve myself and splash some water on my face I went, slowly beginning to think of the fun to be had this day.
I proceeded back out to my room and began to lay out the clothes I'd be wearing for Richard tonight. My new black dress, new stockings to go with, the high stiletto heels, the choker and the corset and finally, the bolero sweater to go with it. Piece by piece it went on, slowly changing me into the woman I wanted to be. I piled my hair into a french twist, high on my head, my make up was done perfectly, my nails were beautiful and that dress... was positively painted on. I looked gorgeous. As if on cue, after a bare half hour wait, Richard pulled up, and entered the house exactly at noon.
I flowed across the floor to him, wrapped my arms about him, and turned my face up to him. He responded in kind and kissed me with the most passionate kiss I had ever had. I could feel him rise in his pants as he pressed himself into my hip. I was quite excited myself, I must admit.
"This paperwork can wait. I've got to have you." he said, and led me back to the master bedroom. I followed along blissfully.
In the room, he turned to me again, and we kissed once more, his hands roaming over me, my back and ass and up front to my breasts. With ever increasing excitement, he began to undress me. He drew my sweater down and off my shoulders to drop at my feet, then unzipped my dress to pull it from my body. Disrobed, he stepped back to examine what I looked like. The corset I wore accentuated my hips with a vastly drawn in waist, my false breasts were covered in the cups, and looked quite natural, and everything about me from nails to hair looked female. Except for one thing... between the garters holding up my stockings was a cock, prominently standing, and waiting to be used.
Richard did just that.
Sitting on the bed, he drew me towards him, and took me within his mouth. I groaned at the feel. I had always loved a blow job and though he wasn't practiced, it was still good. I thought to myself that I'd be able to teach him better in time.
Feeling his mouth and tongue around me and his hands on my ass, it wasn't very long before he had me coming in his mouth. When I had finished, he looked up at me and told me to lay back on the bed. He undressed as I did as he told me.
When he had finally stripped himself bare, I looked between my legs to see his hardness rise up. It was beautiful to me, so strong and manly looking. He slowly stepped between my legs, caressing them through the nylon, pulling them gently up and apart. He rolled a condom down his cock, and lubricated himself up, then, placing his cock at the entrance to me, he looked me in the eye. When I smiled back at him, he thrust in.
All the breath rushed out of me in that first thrust. Then came the second. And the third. Soon I lost count in the bliss that his cock was creating within me. I think I orgasmed again while he was punching his cock in and out of me. When he finally came deeply within me, he collapsed onto me.
We kissed and caressed each other in the afterglow. I loved the feeling of his weight upon me. After about an hour, he revived a little and asked me to roll over and kneel on the bed.
I obliged and smiled when I felt him fumble around behind me and once more thrust into me. He lasted a little longer this time, and it was just as much fun for me this time as the last. When he finally came once more, I fell to the bed. Behind me he was cleaning up and getting partially dressed.
"When you get cleaned up, come out to the kitchen. I have our contract out there."
"Alright Richard," I replied and began getting up. In the bathroom I washed my sore ass as gently as I could, then returning to the bedroom I pulled on a short black silk robe I knew would drive Richard mad.
I must have been quite a scene when I entered the kitchen, judging from the look on Richard's face. I know the image of a woman in tall heeled sandals, black nylons and a black robe that leaves little to the imagination has that effect on some men, but he'd just had me.
I walked over to him, and sat on his lap to go over the papers. We discussed the agreement, I made a few changes, then we signed on the dotted line.
Some of the discussed items were what I would require to let him have sex with me without a condom. My response was an aids test right away and at three month intervals. Then he wanted to know if I would be amenable to having breast augmentation surgery and other plastic surgeries to make a more feminine look. I counter proposed that he would have to pay all the costs associated with any change he wanted, and make a deposit in a bank, in my name, to cover any reversal of surgery performed. Finally he asked if I would take hormones to feminize myself further, I agreed, again with him paying all the costs associated. As he agreed to all the specifics, I had no problem signing on the dotted line.
Besides, I know it was a little cruel, but all throughout the meeting, I wiggled on his lap and showed the top of my stockings. When the deal was done, he threw me over the table, lifted the edge of the robe, and fucked me right there. Just before I came once more that day, I noticed Sandy outside the window, watching us. Her hand was under her skirt and there was little left to the imagination in what she was probably doing. That ended it for me and I came loudly soon echoed by Richard.
He cleaned himself up quickly and left. I slumped to the chair we had just been sharing. Then, smiling, I wondered what to do with Sandy, my little voyeur.
I kicked off my heels, stood shakily and walked back to the bedroom, there to take a long hot bath and though it was barely after six, I felt it appropriate to ease my soreness into bed to sleep til morning.
I woke predictably early the next morning. Getting up after lounging for longer than I usually ever did, I quickly dressed in my exercise gear, and went out to the living room to work out. An hour of intense work and I was ready for the shower.
Then I got ready for the day. I thought to myself about what the day would probably hold. I knew I was a new enough diversion for Richard that I'd probably be visited by him when noon time came along. Also, I needed to figure out just what I was going to do if Richard took the new clauses of the contract to heart and enacted them. I would have to leave my mother's house in some believable way and do so in such a way that I wouldn't be expected home often. Once the changes started, I would have to 'come out' to my mother. I still did not consider myself gay, or at least not as one would think. I had always wanted to be a girl, but I have never been real attracted to men. It was women I found all the beauty and desire for in my fantasies. I was truly that lesbian trapped in a man's body. This thing I was doing with Richard was a job, and a means to an end. I was going to be the woman I wanted to be, I didn't care that I had to fuck this man to get it.
Therefore, I began planning what I was going to do when this gravy train derailed. I began researching online schools for computer classes that I could take in my time off from Richard so that when he discarded me I would have something to do.
At noon, I was dressed in a short teddy, hose and high heels to greet Richard at the door. We didn't get past the living room before he had me down on my hands and knees being royally fucked. I had my body thrown over the coffee table and was holding on for dear life as he pounded himself into me, over and over. I screamed when I came mere moments before him. Then, he carried me to my room, placed me on the bed and finished undressing himself. Sliding in beside me he pulled me close to him and we began necking and he began biting my neck and shoulders. His hands roamed over my body and felt every part of me. It wasn't long before he was hard again, and pulling my legs apart and around his waist, he slid his cock into me for another marathon session of sex. I drew him closer to me with my calves and scratched his back with my fingernails as he pounded into me. When he spend himself, he collapsed onto me. I just held him as he slowly dropped off to sleep.
I let him sleep there atop of me until he had to get back to work. He got up, kissing me quickly as he dressed, and left. I watched him go, but lounged around for a few hours. Then, I got up myself, took a shower and washed up, then, putting on my male clothing I went home to tell my mother the great news. I was going to take some training that the company I was working for was offering, then I was going to get a promotion, a raise and maybe more. She was ecstatic, and I had the beginning of my alibi.