Male Mistress

By Tiberius

Published on Jan 23, 2004

Transgender

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 2)

I was now cleared to stay at my new house for a few weeks. According to the story I had told my mother, I would be put up for training for a while. That would be good enough for the 'newness' of my new relationship to calm down with Richard. I didn't think that after that much time had passed, I would have to worry about him popping up every day.

I mean, really, how often does a man say he wants sex every day, but when he gets it, it doesn't last very long. In two weeks, he'll be down to maybe seeing me twice a week, then in a month he'll maybe see me once a week. After that, then I have to start trying to keep his interest in me, or have something to blackmail him with. Not that I would, however.

Anyhow, after a night sleeping at 'home,' I was back to what I was hoping would be my new home for quite a while longer, getting ready for my job.

Already I had found out what my biggest problem will be in keeping Richard's interest; variety.

Looking through the very scarce amounts of feminine clothing I had, I didn't think it would be very long before I had nothing 'new' enough for him. I decided my best bet would be to just keep to the fancy lingerie and not worry about the special outfits until the newness of having a mistress of his very own wore off. I had greeted him in a teddy yesterday so today I would greet him in a garterbelt, stockings and bra set. A little different, but basically the same.

I greeted him at the door once more, and led him to the bedroom as he lost pieces of his suit every few feet.

I had set the mood with soft music and lowered lighting and he just looked amazing in the candle-light. His muscles rippled gently under his flesh as he reached out to take me in his arms. I don't know if it was just the situation I was in, or if I was changing slightly inside, but I found it immensely erotic. I was getting hotter and hotter just standing near him and basically taking in his maleness.

I flowed into his arms and raised my face for him to kiss me deeply. He held me closely and kissed me more passionately than he had ever kissed me thus far. My knees felt weak and I responded like never before. He slowly led me to the bed and laid me upon it. Then, working slowly from foot to head, he laid kisses upon my flesh. I must admit I was in a sweat before he finished his trip up my body. He was sure putting effort into getting me in the mood this time.

When he finally got to the business of getting my panties off, I was his. I struggled to get them off me faster than any woman ever had before. I threw them away from me and he got between my legs. He spread me out, and slowly pressed his lubed and rubber covered cock into me. I almost screamed at him to hurry up and fuck me! In what seemed like an hour, he was finally full length inside me. With hardly a pause, he pulled out of me and then thrust back into me full force.

That time I did scream out in ecstacy, and I didn't stop until finally he came deep within me and fell exhausted to sleep atop me.

I just laid there and breathed. I felt like I had forgotten how to do that simple little thing from the sex being almost too good. I could still feel the great feelings washing over me and I didn't want them to end, but eventually they did fade. I let Richard sleep until he had to wake up to make it back to the office on time. He left me an envelope when he departed for work, telling me it was a proposal I should take some time to think on. Then he told me to be ready for a night out at a nice restaurant tomorrow night. I kissed him goodbye just inside the door, and he left in a rush.

Then, with nothing left to do until tomorrow night, I went to the master bath and settled in for a good long soak. I opened the envelope Richard left me while waiting for the bath to fill. Inside was a brochure for what seemed to be an addiction clinic. As I read further, I came to realize that was very far from the truth.

The Tau Clinic was a clinic for 'special' women like myself. With a minimum of fuss and a definite maximum of money, anyone could get whatever plastic surgery, chemical assistance and some minor reprogramming to turn a man into the perfect she-male or even fully realized new woman. The bath finished filling, and I slipped out of what little clothing I was still wearing and eased myself into the water. Then, comfortable, I continued reading.

According to the ad slick, in just seven days, Charles Atlas could make you a man, but since women were just a little more complex, the Tau Clinic would take a full month. I laughed a little at the joke, and hummed a few strains of the Rocky Horror song that came to mind. Then I looked at the admittance questionnaire that Robert had provided in the paperwork he had left for me to read to see what he had in mind.

In the first sections were the pretty standard things: Breast size desired as well as final measurements, hair color, wether hormone replacement therapy would be used, things like that. It was in the second section that the things started getting weird. As an example, take this question.

If the client is to be a She-male, is she to be functioning? Some hormone replacement therapies can cause erectile disfunction, shall she be equipped with a pneumatic penile erection device? Shall the device be remote controlled?

It continued in the same vein. There was a question of how to get the feminine hip dimensions correct, implants or surgical rearrangement of bone. This place was hardcore. Then I looked at the prices. A full work over would cost Richard on the order of a million dollars, and that was the minimum. I didn't think I was worth this much to him. Then I remembered the contract. I wasn't worth this much... I was worth twice this much.

I regained the warm fuzzyness that my amazing afternoon with Richard had given me. I also knew now what had gotten into him to make him so focused on me today.

All evening I set about planning what I wanted to look like. I looked up photos online, researched what the 'proper' proportions of a woman were and I measured myself to make my desires within the reasonable range that the Clinic documentation described for best results. I stayed up late and answered every question in the questionnaire. When I finally went to sleep that night, I dreamed of the perfect woman I was to become.

Obviously I woke late the next morning, and already I was late for the day I had planned. I wanted to look my very best for Richard tonight, especially as he wanted to take me out. I had a lot to do if I was to look like a proper woman for him. The first thing on my list was once again dealing with that pesky body hair. I smiled to myself as I got the waxing materials out, and began to prepare myself. One of the major problems with being born a man is the speed at which hair grows back. The two weeks advertised by the products I was using only work that long with estrogen flowing in the recipients blood stream.

When that was finally, and painfully, done, I then moved to my vanity table to pluck and shape my eyebrows. I had gotten rid of my horrendous unibrow that birth had cursed me with when I first began cross-dressing, but they continually needed to be touched up. But today, I was going further than I ever had before. I wanted no longer to have slightly feminine eyebrows that would pass when I dressed as a man, I wanted a woman's eyebrows. I wanted them thin and arched. I set out to do that, and after quite a long and careful time, I finally had that. The change was even better than I dreamt it could be. It's not the big things that make the most change in a person's attitudes and perceptions, but the little ones. When I looked in a mirror wearing my fake breasts and my hair in a ponytail and high heels, I never felt quite as feminine as when I looked now at my eyebrows and what it did to my face.. I knew then that I had to pierce my ears. It was the logical next step and I was eager, but I didn't have time today.

I checked the clock, and time was speeding toward my deadline. I needed to hurry up. I quickly dressed in tights, leotard and sneakers and ran to the den. I began my now daily workout to slim myself down to make the illusion all the better. As I was finishing up, I was startled by a knocking on the sliding glass door. I quickly spun around and looked, and there she was. My neighbor girl, Sandy, was on my back porch, crying and obviously looking scared. I got over my startlement and opened the door to let her in. She fell into my arms and I led her to the couch where I comforted her.

"What's wrong dear?" I asked her. "Tell me, please." It was a while before she finally calmed enough to speak to me.

"It's my mother's boyfriend. He's after me again. I told my mother, but she doesn't believe me. The last time I told her, he stopped. I guess he was afraid she'd throw him out, but since she hasn't, he's gotten worse."

"You're safe here. I promise you that. Is there someone else you can tell? Some family member who can convince your mother what's going on?"

"No. My mother was thrown out for having me and we moved here so she could get work. She's doing well now, but she still hasn't figured out how to pick a good man for herself. At least this one doesn't beat her, but he does just sit around and leech off her money. And now he tries to have sex with me."

"I'm so sorry, Sandy. I'll try to help as much as I can, really."

"I know you have a guy who visits you sometimes, but if he's not here, can I kinda stay and do stuff here until my mother gets home? He doesn't do anything when she's around."

"Of course you can!" I grab her and hug her tight. "I think you should tell someone with some authority or something to stop this, still, but until then you can stay here whenever you want."

"Oh, thank you!" she cried as she buried her face into my chest.

"Right now, however, I need to get ready for tonight. I have a hot date. Would you like to help me?"

"Sure, ahh.. What do I call you? We've talked, but I don't think your name ever really came up."

"Oh, I'm sorry. I guess you're right. I'm Colleen Marsden. You can call me Colleen if you would like, since we're friends."

"Thanks. I'd like that." She finally smiled one of those glowing smiles that I had come to expect from her, and again I saw the beauty she was going to become.

We both wandered to the bedroom and she took up position on my bed as I quickly chose the clothing I was going to wear tonight. I decided that the black dress and bolero jacket would be the perfect thing for this evening. I got out all the black lingerie I had worn that day not so long ago and my heels and laid them out. Then I went into the bathroom to shower. It was difficult to be so openly womanly for my guest and not be too modest, but still hiding what I really was. Somehow I managed to pull it off until I could put on my black satin gaff and my robe over my lingerie covered false breasts.

Throughout it all we talked about her life. What classes she was in and which ones she liked. She was focusing mainly on sciences and I assured her that I had done much the same.

She backhandedly flattered me by saying, "But you're too pretty to be a girl who likes science."

I laughed, almost ruining the job she was doing on my make-up. When she looked hurt I explained myself. "I wasn't this beautiful when I was in high school. This takes a lot of work, and I only do it because I decided I wanted to. I used to look just like you. Well, not just like you, but the glasses and the uniform that just didn't make it easy to see what an individual I was. My peers didn't like me, so I determined to make myself the best person I could, and only be the kind of person I wanted to be."

"Yeah, it worked for you, but what about me. Only my mother's boyfriend wants to kiss me, but that's because he's a 'perv'."

"You are very beautiful. You just are not what boys your age want. Now, people like me will see you as beautiful as you really are." Then, almost belatedly I added, "when you're my age, that is."

She just looked thoughtful at that and continued working on my face.

When finally I was put together, I finished dressing, and we awaited Richard's arrival in the den watching television. When I heard his car in the drive way, I jumped up and my heart started to flutter in my chest. I didn't know how I could stand it, but I did. I gathered up my purse and walked to the door.

"Wish me luck," I asked of my houseguest. And with her "Luck!", I went out to meet Richard.

Like a true gentleman, he opened my door for me and complimented me on my looks. I smiled in true appreciation for his efforts and got into his Lexus.

During the short drive to the restaurant, Richard handed me another of what were to become his ubiquitous unmarked envelopes. "It's more of what I've promised you," was his cryptic response to my body language asking what this was.

I opened the envelope and inside were two credit cards, a drivers licence, some papers and a coupon for a sam's club membership under his corporate account. All of these had my full feminine name. The papers, when I pulled them out to look at them more closely, were a new birth certificate, social security number and the application for a passport... all it was lacking was a photo and confirmation signature.

I looked at Richard and asked him how he had gotten all these things.

"Contacts, and money... but mostly contacts. When you're as big a business man as I am, you get to know a lot of people, those people start to owe you things and the result is things that can't happen for normal people start being possible for you. For this thing we have to work out, you need to be a real person. People overlook some things in the real world. An executive of my stature and power is expected to have a mistress, can sometimes get away with a boy toy, but what you are is still too much for conservative society. So, I made for you a feminine persona that frankly, can hold up to almost any scrutiny. And, to make things easier for you, I'm continuing to pay your old self a salary so that you may pick it up at any time if you wish. I don't want you to feel trapped."

He smiled at me and I smiled back, carefully trying to keep the tears at bay. I now knew how I could use his help to keep the ability to change back to my old self alive. I could go to school, college I mean, in my feminine persona, and take the same classes in distance learning in my old male persona. We'd both get diplomas in the same things and therefore both be equally marketable. I won't be trapped being Colleen. I put all the paperwork away in my purse; the cards, licence and social security card in my wallet, the paperwork back in the envelope.

Then, we arrived at the restaurant. He took my arm as we walked up the red carpet to the door, and the doorman held it open for us. The smile that the doorman directed at me showed me that I was not just desireable to Richard. For that matter, the way the waiters and busboys ogled me, I felt positively gorgeous.

I had definitely been lucky that the clothing I had bought was as fancy as it was. This was a class restaurant, and I just barely fit in. My jewelry was cheap and plain in comparison to the other women here, but it wasn't embarrassingly so.

Richard noticed my discomfort and told me to calm down. "You're more than beautiful enough that these crones will all be jealous anyway, you don't need the jewelry and minks as well, though, in time you will have that as well." Then he covered my hand with his own, smiled, and turned back to his ordering.

The food came in courses, five in all, with sherbet or light salads of greens in between. I was amazed. I now realized why the portions were so small in all the gourmet restaurants I had seen on television. If they were what I, as a normal middle class American, had usually eaten as a meal, we could never have finished the second course. As it was, I still felt pleasantly stuffed when the dessert had finally been cleared away.

Then came the second surprise of the night, I thought we were just here to eat, but the lights in the room dimmed further, a curtain at the side of the room opened and a stage was revealed. It was a dinner theater, and now was time for the floor show. The women of the chorus were beautiful in their glittery outfits, the singing was awesome and I was overwhelmed that something so simple seeming could tell a complex story.

I don't know if Richard felt the same way, however. He seemed fixated on the breasts.

Finally, however, the night ended. Richard escorted me out the front where we waited bare moments for his car. He handed me in to my seat, went around to his door and we went off to my home.

I asked him in, and he accompanied me to the kitchen. I made us coffee, and we sat down. Before too long, however, he started to play footsie with me and I responded as favorably as I could; I stood, took his arm, and led him to the bedroom.

I turned on some soft music and lit a few candles, as he turned off the lights and began undressing. I turned around to find him gloriously naked and entered his offered embrace. As we kissed, he gently began to remove my clothing as well. When he got to my bra, I tried to stop him, but he pushed my hands away.

"It's ok, just this once I want to make love to you just as you are, totally naked. If you carry through with our plan, this may be the last time you can do this, and I don't want you looking back with regrets. I want you to know, for yourself, that you aren't gay. At least not as a man for a man. Am I making sense with this?"

"Yes," I respond. "I understand what you mean. You have demanded a lot from me and I've said yes all along. You just want to be sure that I really mean it, and how can I really mean it if I don't try other ways to be sure I don't want them. Correct?"

"Yes," he replied in a breathy whisper, and slowly took off my bra, taking the false breasts away with it. I stood before him, a skinny, runt of a boy, with long fingernails, no body hair, make-up and long feminine hair. I also stood before him feeling quite vulnerable.

Nervously, I responded to his touch and move to the bed. He moved himself close to me and we kissed. I still felt anxious in his presence. I had been with him many times over the past few weeks, I didn't know why it was so different now.

With gentle hands, he guided me under the covers. I rolled across the mattress and he slid in next to me. He rolled over, and gently kissed me as his free hand traced itself over my body. When it had reached my cock, I responded much slower than I usually did. Finally, I had had enough. I wanted this formerly great night to end.

I began kissing him back passionately and stroking his cock, hoping to 'rev his motor' enough he'll get it done with quickly. He responded predictably. In bare moments, he was rolling a condom down his length, lubing himself up and thrusting himself deep into me. In moments he was spent.

"Do you mind if I stay over tonight?" he asked me as he rolled away.

"Of course not," I smiled back trying to look happy for him. "It is your place as much as mine. What time do you need to wake?"

"Six o'clock should be fine, thank you." I leaned over him, and set the alarm. Then I pulled the covers up over us and rest my head on his chest. In moments he is asleep and snoring gently. I, however, am not so lucky.

I lay there thinking on what just happened. Why did having sex with Richard, something I had done many times before, disturb me so much tonight. Was I a different person in my mind when I was dressed up as a woman. Was it only because of what I was or was not wearing?

I carefully got up, collected my clothing and other things from the ground, and wandered into my dressing room/walk in closet. I put the dirties in the hamper, got a sport-bra and panties set and a light nightie. Prior to putting all this on, I re-attached my false breasts and then, immediately after, I exited my bedroom to sit in the living room.

I comment on such mundane things because it wasn't until much later that I realized that this is what I had done. I remembered being in bed one moment, then next I found myself huddled on my couch crying. I mean, the hysterical, shuddering type. I don't know for how long this occurred but it was almost five in the morning before I was calmed down enough to start thinking again. I sat in the dark trying to put my mind back into order. What was I going through, why was I acting this way.

As I sat and thought, things came back to me. I remembered being a very young boy, nine or ten, and a man that used to live in my town. Deep buried memories welled up within me. I tried once more to hold off the crying, but was unable. He was friendly, then he was abusive. I learned how to keep him friendly, and how to avoid making him abusive. When the inevitable eventuality came, and he wanted me to have sex with him, I did it. I hated it, and I didn't want it done to me, but I didn't want to be punished either.

Now I knew why I had to pretend to at least pretend to be female for Richard. I wasn't gay, or couldn't let myself think I was gay, or it reminded me too much of my past. Did that mean I didn't really want to be a woman?

I thought long and hard about that. But, eventually, I realized that I had always been a cross-dresser and felt I should have been female. I was dressing up since before I ever met that man, and I never associated the two in my mind. I wasn't positive that I was right, but it felt like that was the correct feeling.

Finally, more at peace than I had been in a long time, I washed my face and crawled back into bed with Richard. When the alarm rang, waking him up, I happily went into his arms to kiss him good morning.

"You're dressed again?" he asked me.

"Yes, I prefer it this way. I want to be your she-male, mostly woman, but not totally so."

"Good, I'm glad. You've looked over the brochure I gave you, correct?"

When I nodded yes, he went on to ask me if I was ready for that. I was, and he went over with me what he wanted to have happen. He was willing to have implants make my hip structure more feminine, and he wanted any breast size I would be comfortable with. He also didn't care what I wanted for hormone replacement as long as I would still be functionally male. I told him I'd get the paperwork filled out, and sent to him in a week, and I'd be prepared for the trip whenever he'd like it done. He agreed that a week for the paperwork would be adequate and hoped that by the end of the month I'd be enrolled in the Tau Clinic's program.

I walked him to the door and let him out, kissing him on the step as he left. I went back to my bed, curled myself into a tight ball, and fitfully dozed off.

That afternoon, Sandy was once more over visiting me. We sat and chatted as she did her homework. I thought about my revelation about myself and as I sat curled in my armchair talking with sandy I realized I felt right. I was happier in these clothes, relating to people in my feminine persona. I didn't hate being Collin, far from it. I just loved being Colleen. I smiled and felt much better with my choice.

The moment Sandy left for home, I went to my office and began the paperwork that would change me into the person I wanted to be.

Two weeks later, I told my mother that the training had gone well, but I was going to be transferred at the end of the month. I was going to be making much more money. She was upset a little, but she wanted to see me succeed. When I told her that the new job included training and schooling, she was ecstatic. She had always wanted me to go on to college and now that I was (just as Colleen) she was happy for me. I was no longer tied to my masculine self and all barriers to Colleen were gone.

Next: Chapter 3


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