Lawyers In Love, Part Three

After everything that happened that night, I was expecting that there would be a lot to talk about the next morning, but I was wrong. At six-thirty I knocked on her door and she gave permission to enter. I went in with her coffee and the newspaper, wearing one of the maid’s uniforms. I set down her coffee and went to draw her bath. She put on her glasses and started reading the paper. No words were exchanged.

Bedtime that night was a different story. About nine, she rang her bedside bell for me. When I appeared, she was studying menus for the parties. Without looking up, she said, “Go to your room. Prepare yourself for the usual.”

A few minutes later she repeated what she’d done the night before: the teasing, the prostate massage, making me promise anything, and I had just as shattering a climax. When I was finished she peeled off her gloves. “From now on, you will give yourself a thorough cleaning enema an hour beforehand. And lubricate yourself before from now on. Unless you like it dry, that is.” She went to bed without another word. It became our nightly routine. And every night I looked forward to it more. Even though I was getting release every night, I often got erections during the day at work. Several times a day I had to go to the washroom and touch myself, though I was careful not to come.

She made it different each night. Some nights I received a straight hand job. Sometimes on those nights she fingered herself under her skirt with her free hand. When she was done she would wipe her lubrication on my face. Then there were nights she barely touched my cock, just holding it up with the tips of two fingers, while she finger fucked me with two or even three fingers. Some nights she was so slow I was moaning and babbling like an idiot in frustration; there were other nights when she brought me off so quickly she seemed to be racing against a timer.

After about a week, she informed me that I should be home by four, because we had to travel into the city to meet with the medical doctor she’d mentioned.

By now I was used to following her instructions, but when we were in the car I was curious. “You said he helps people with appearance issues. Is he a dermatologist or something?”

“His name is Felix Spector. He helps men pass as women if they need to.”

I was a little nervous about a doctor being involved. “Sounds like people in the theater, with makeup, would know as much.”

“He comes highly recommended. And I want to get his ideas; we only have five months till the first party.”

I was glad to know he had credentials, because the setting of his office was discouraging. It was in a terrible neighborhood in North Philadelphia, not quite the ghetto but not too far removed, either. I was glad to find a parking lot with an attendant; leaving the car on the street was an invitation to vandalism or worse. His office was little better; “shabby” came to mind.

Doctor Spector was a thin, very aged man, stooped, with a hint of palsy in his movements. But his eye was clear and there was still a bounce in his step when he came out to the reception room to greet us. He shook hands with my wife, “Good to meet you at last. I was wondering what you were like.” He shook my hand as well and ushered us to an examination room.

Dr. Spector looked at me. “Your wife has explained your situation to me. I’ve helped many people, both sexes, with these transition issues. We will give you the best care available. Please take off your clothes so I can examine you.”

I was flustered; under my male clothes I was wearing a bra and panties.

“Just get undressed,” she said impatiently. “He’s seen it all before.”

I was utterly embarrassed; only my wife had seen me in lingerie before. I turned away from Dr. Spector as I undressed and only faced him again when I was naked. He walked around me slowly, occasionally looking closely or gently pinching some skin to get a sense of my body tone. He spent a particular amount of time studying my face, having me turn my head in various ways under the lights.

He sat down and made some notes and then turned to my wife. “He is an excellent candidate for transition. So many of the patients I see are unsuitable, no matter how much they want it. Too old or too heavy or simply the wrong body type. He’s young, very fit, with good skin tone. I think you will be very pleased with the results if you follow my instructions.” He turned to me. “It looks like you exercise.”

“Free weights, every other day.”

“You’ll need to stop. No more weight training. It will bulk you up and give you too much definition. Do sit-ups, core exercises, balance drills. Nothing that involves the arms. They are too big already. How much do you weigh?”

“One hundred seventy.”

He shook his head. “Too much. We need to get your weight down to a hundred forty. I have a recommended diet I will give you on the way out. Twelve hundred calories a day, low protein. We are going to have to be vigilant about your weight from now on.” I was puzzled but said nothing.

He turned to my wife. “When does the electrolysis start?”

“I’m hoping to get him in next Monday.” I was startled to hear her say this; she’s said nothing to me.

Spector frowned. “And you want him to be able to pass in five months? Hmm. This is normally a two year process—I trust you appreciate that. Can you book double sessions?”

“I think so.”

“Electrolysis makes a huge difference. There are some men, slightly built men with little hair, who need nothing else to be able to pass. The more we can get done, the better. Of course, since we’re short on time I can up the medication. That should help a good deal.”

“Medication?” I asked.

“Estrogen injections to soften the skin and redistribute the body fat under the skin. I’ll show your wife how to give them. It will go a long way to help you pass. Your pores are large. The injections will close them up, give your skin a smoother appearance. And androgen blockers, of course, to help the estrogen do its job. Another thing, very important, not appearance but just as vital, you need to have training in how to move as a woman. Men take large steps, wave their hands in big movements, sit with their knees apart—the most careful preparation in appearance means nothing if the body language gives it away. I’ll give you a list of movement coaches I recommend. A fellow like you, with muscular movements, we have a lot of work to do,”

“Doctor Spector?” I asked. “Just what will all this do to me?”

“Well, it will allow you to pass as a woman, at least as much as we can in a few months.”

“But what will it do? Permanently, I mean?”

“Unless we are talking about surgery, nothing is really permanent. You were born a male and you have functioning testicles. Your body will always try to revert. The only thing that is permanent is some of the hair removal from the electrolysis. Half the hair removed that way will never come back; the rest will, over time. It takes three and four sessions on the same patch of skin to get it all. Hair is a pretty persistent thing. As I said, my transition patients take two years of electrolysis, sometimes more. To the extent you experience redistribution of fat, that would be permanent, but it could always be corrected surgically if you wanted. Keep in mind that the estrogen effects will start to wear off as soon as you stop taking the medicine. Your body will always resist the estrogen, anyway. That’s why we need the androgen blockers, to give the estrogen a chance to have any effect at all.”

“Can’t I just, you know, do makeup? I mean, having my beard off, that’s no big deal.” I laughed nervously. ”Not having to shave every day would be nice—a lot of men would like that. I’m just nervous about the rest.”

He seemed a little disappointed in my reaction. “Well, you can do as you like; but from a medical point of view, there will not be a satisfactory result if you don’t go on high dose estrogen with androgen blockers as soon as possible.”

“Satisfactory?”

“When we see another person there are dozens of clues about whether we are looking at a man or a woman. Forget clothes and hair length for a minute. If you met a flat chested short haired woman, even before she spoke, you think you would mistake her for a man?”

“No. There’s her skin, the curve of her hips, how she’s muscled, lots of things.”

“That’s right. And if you saw a man in a dress and a wig, you’d spot him no matter how close he’d shaved and how much makeup he had on.”

“You’re right.”

“Your body has to be adjusted chemically to give off the little clues that real women do.”

“I just wonder if this is even . . . practical.”

“Oh, of course it is. I don’t want to discourage you; it’s just that I like to see really good results, and we need your full cooperation. It doesn’t have to be 100% perfect to work. If someone looked at you if you were on androgen blockers and had been carrying a full estrogen load for a while, there would be enough feminine clues that they would miss the male clues.”

The appointment went on a long time. Dr, Spector loved his work and I never had a sense that we were being rushed. We left with a bottle of pills, a vial of liquid estrogen and some needles and syringes, all of which my wife put on my card.

She was in a wonderful mood on the drive home, telling me one thing after another about her plans for the parties and how it would cement her partnership. I listened and thought about the fact that she made a point of always using my credit card. “If this is for me to be able to help you,” I asked her, “You ought to be paying for it, not me.” It seemed a silly thing to be thinking of when I was about to change my physical appearance, but my mind was stuck on it.

She had her answer ready. “This is for you, not me. I could hire a maid anywhere.”

I considered what she’d said. “You wouldn’t go to a tenth of this trouble if you didn’t love it.”

“Yeah, you’re right,” she smiled. “And I do love it.”

“It’s been wild,” I said. “I’m just a little . . . It’s a lot to think about.”

“It’s like the song, you ain’t seen nothin’ yet.”

That night, as I waited for my evening milking, she gave me my first two androgen blocker pills. She picked up the syringe filled with estrogen. We both looked at it. “Looks like it’s just water,” I said.

“It’s really thick. It was hard to pull it out of the bottle.”

We looked at each other. “This is going to change things,” I said. “It’s not going to be the same, after.”

She used a cotton ball with alcohol to rub a spot on my ass and then stuck the needle in. There was no pain. “Not bad for a first try,” I said.

She didn’t push the plunger right away. “What do you think it will do to you?” she asked.

I wasn’t sure what she meant. “Like Doctor Spector said, it will help me pass.”

“It’s going to turn you into a woman.” She pressed the plunger a little.

“Just a little,” I said. “And it’s temporary. The way he made it sound, it’s like makeup.”

She pressed a little more.

“I can feel it inside me.”

“Think about it moving around, getting into your blood. How does it feel?”

”It doesn’t hurt. I’m just thinking about it . . . inside me now.”

”Think about what’s in here,” she said slowly. “You’re full of the juices that turns preteen girls into women. Do you have any idea how this turns me on?” She pressed until the syringe was empty, but still didn’t pull it out.

“A lot.”

“Oh, you have no idea. Welcome to puberty.”

She outdid herself with her milking that night.

In the next month, the maid project starting taking over more and more of my life.

My wife found a female drama coach who gave me movement lessons twice a week, and there were drills to do every night when I was home. The coach was a slender woman of about 40 who usually wore black leotards and jeans. The top was so sheer and so tight it was clear she had no bra underneath. Marilyn allowed me to go without my female underwear, which was a relief, because there were times the coach would touch my shoulders or side to help me get a movement right. She was under the impression that I was going to play a woman’s part in a community theater. I was taught how to walk with short steps, how to move my hand minimally, how to walk with just the slightest sway in my hips. I learned to sit with my knees and ankles together. She worked with me on a softer voice in a higher register, too. It was very strange, at first, and I felt impossibly awkward. I realized how the gestures and movements of the average man were so abrupt and overdone. And as I began to move more softly, with more subtlety, I recalled what Doctor Spector said about the clues.

Once a week, I went to my wife’s beautician after hours. Partly I was being groomed to appear more feminine and partly she was teaching me about makeup. The story to her was that I was going to a Halloween party as a woman and we wanted to be sure I won first place for best costume. She was young, barely out of high school, a bouncy little thing with pert breasts and a tattoo on the side of her neck. She thought the whole thing was hilarious. She plucked my eyebrows, just a little at first, and experimented with different hair styles. Because it was short, she started with a unisex style that would look short if combed straight back, but would look fuller if combed to the side. She began teaching me about makeup; what shades, how much, how to apply it; there was a lot to learn. And I realized, again, how right Doctor Spector was; makeup would help, but even skillfully applied it could only do so much, and it was no substitute for feminine skin.

There were several other big changes, but neither took a lot of time, diet and exercise. My diet was severely restricted; no alcohol, no sodas, no sweets, and only tiny portions of food, not a third of what I was used to. I had to weigh myself every other day and report to my wife. No more going out to lunch for me; I took some carrots and celery in a paper bag and worked through lunch. I had to drink a lot of water to keep the hunger pangs away. After a few days I became used to the amount of food and my stomach stopped hurting. Very quickly I found myself becoming weak. I had enough energy to get through the day, but I was tired in the evenings and slept more.

The only change that simplified my life was exercise. My free weights disappeared; instead, I did a regimen of sit-ups and stretches. But there were a lot of sit-ups. My abdominal muscles ached for the first few days and then grew accustomed. By the end of two weeks I could feel my stomach getting flatter.

Then there were the electrolysis treatments.

My mother had complained to me a few times about hair removal, so I had some idea what it would be like. But it was my least favorite part of the process. There was no plausible cover story to give the technician and my wife didn’t try; she told her that I wanted permanent hair removal, period. The technician and I never discussed it. She was an older woman, heavyset with gray hair. The sessions went in total silence except for her necessary instructions. I sat there and wondered what she was thinking as the needle gradually destroyed by body hair.

My wife had booked me for two hour sessions twice a week, Tuesdays and Fridays, and that was all I could stand. I had to imagine being found out at a formal dinner party to give myself the motivation to handle that many treatments. My skin was naturally hairy, which meant the progress was slow and painful. The technician would work on a tiny patch of skin somewhere on my face till it was too swollen and painful to continue. Then she would move to a different spot, and then another, till she ran out of face. Then she would go to my chest. There were fewer nerves there, and fewer hairs, at least in comparison. Because I was already shaven it was hard to gauge how much progress she was actually making, but any time the damned needle was away from my face, I was happy. The Friday session was the worst; wherever she had worked Tuesday was still tender, so she couldn’t work more than an hour on my face and chest till I was done. To fill up the second hour she worked on my legs, or, more rarely, my ass. Thankfully, my wife had decided I would not have my pubic hair removed, although she required me to keep it shaved.

I shouldn’t leave the impression that it was a month of nothing but work; every night, without fail, my wife was ready to milk me. I was having more sex than I’d had since college. There were nights she was home late, or had a headache, or her period, but none of that mattered. I got my release every night. It’s just that, as the weeks went by, it gradually changed.

It was not a matter of changes in my body; I was watching for that but they were hard to identify. I lost ten pounds in the first month of my diet, it was hard to see where it had come from. My butt seemed the same size. My shirts felt the same, except that they were getting tighter across the chest and looser in the collar and shoulders. The only thing I could definitely see was that the patches of skin where the electrolysis was complete looked very smooth and feminine. The doctor was right; it was easy to see the difference between skin that was shaved and skin that was truly hairless.

The first clear change was I began to feel less edgy and more calm. Little things upset me less and I had more patience. Getting my own way wasn’t as important. I began to feel lazier; I had less sense that I had to jump up and be doing things every minute. I was glad that the doctor had advised against exercise; I didn’t feel motivated to do much beyond the required sit-ups.

As the weeks went by, my skin was more sensitive. Not just because it was shaved; by now I was used to being bare. I started feeling erotic all over. I had been a typical man--if you wanted a sexual response, touch my cock, preferably the tip; otherwise it didn’t matter. Now I was discovering that running my hands over my body almost anywhere was sexual. I wasn’t focused on the tip of my cock anymore. It was almost as arousing to touch my nipples as my cock. As time went by, my nipples became even more sensitive, as well as my thighs, my neck and my stomach. I began to appreciate why women loved massages so much. Being touched in so many different places felt equally good.

I didn’t discuss this with my wife; I didn’t need to. As she milked me, I had the sense that she was constantly assessing me. As the weeks went by, and my old male preference for cock stimulation faded, our evening sessions changed. Each night there was a little less cock play. Instead she fingered me more in my ass; with two fingers, then three, and then four. She began playing with my nipples as well as my cock. Gradually there was more nipple stimulation and less cock.

I began having trouble getting erect. Not getting aroused or coming, just getting erect. At first I was just slower to arouse; I put that down to the fact that she wasn’t focusing on my cock as much. But when I would try masturbating at work, I found it was more difficult to get hard then, too. After a couple more weeks, even when she got me hard, it wasn’t a firm erection; it was rubbery and not rigid. It was strange; I was as eager to come as ever, it was just that I wasn’t erect. I had always associated a hard cock with being ready to come and a soft one as a sign I wasn’t ready, but it wasn’t that simple anymore.

It must have been about five weeks after we started the shots that we had what she later referred to as our “breakthrough evening.” It has been an unusually long day for me; a double electrolysis session followed by a class with the drama coach that involved repeated small steps, bending, kneeling, sitting and standing, till my legs ached and I was exhausted. It didn’t help that my evening meal was practically nothing, and that I had to do the wash. By the time she was ready to milk me, I was so tired I almost forgot to clean and lubricate myself.

She came into my room, put on the latex gloves, and began running her hands slowly over my body. It was a very gentle, sensuous touch, and I could feel my body respond despite my fatigue. She slid her fingers down my sides and along my thighs, up and down, unhurriedly. Then she moved up to the small of my back. My hips slowly began to move along with her hands. After a while she moved one hand down to my stomach, barely brushing my limp cock in passing. Her other hand move to my ass and a finger slipped inside. After nearly two months of nightly use, I barely felt it enter. After a few minutes she moved her one hand to my nipples; as she touched them she inserted a second finger and began to search for my prostate. I was fully aroused now, but still limp. And I wasn’t a bit anxious about it. I felt just fine; relaxed, happy, at peace, sexual—the fact that I wasn’t hard seemed irrelevant. I wouldn’t be putting it anywhere. What difference if it was soft?

I felt a gentle tingling in my groin as her fingers brushed my prostate. The tingling became stronger when she added a third finger. Then she started playing with my nipples more vigorously, rubbing them deeply in slow circles. I gasped; she had done this before, but it had never produced such a feeling. It was like having a pleasure center like the tip of my cock, but in my nipples instead. I couldn’t believe it could be that intense. I tried to press my chest more firmly against her hand, trying to increase the sensation but she moved her hand away, teasing; and at the same time she gave me the fourth finger. I thrust my hips back to meet her. For the first time I spoke, “Oh God that feels good.”

“You like this, don’t you?”

“Don’t stop. Rub my chest some more.”

I thought I heard a soft chuckle. She moved her hand down to my limp cock and started playing with it. “I thought you wanted this.” I thrust my hips in time with her hand but it stayed soft. I could barely feel her fingers even though she was holding it firmly; I realized that my cock simply wasn’t very sensitive anymore. The hand in my ass worked slowly in and out.

She moved her hand back to my nipples; they were hard now, and the feeling was like electricity. “Please don’t stop, Ma’am. That feels so nice.”

She pressed on each nipple. “You like that more now?”

“Oh yes; that’s wonderful.”

She began working the hand in my ass in a slow circle, stretching me out even more. I curled my hips back to give her better access.

“You want me to play with your nipples till you come?”

“Oh yes, Ma’am, please.”

“I don’t want to let you,” she whispered. “You’ve been holding out on me.”

Through the haze of arousal I tried to make sense of her words. “No, Ma’am, I haven’t. I’ve given you everything.”

She pressed a little harder into my ass. I could feel the prostate fluid dribbling out, but I still was limp. She talked in a pouty voice.” I give you a place to live and honest work and you’re holding out.”

“No, no I’m not.” I still had no idea what she was talking about.

“You’re going to stop holding out; you’re going to give it up tonight to me.”

“Give it up?”

She pinched one of my nipples. I felt like I was on the edge of having a climax with my whole body. “I’m going to take your virginity tonight.” She pressed her fingers further into my ass. “Right now, I’m going to turn you into a pussy. Press back, like you were on the john, or this is going to hurt.”

It happened in a moment, and yet it was like slow motion. I pressed down, not because I understood exactly what would happen, but just because she told me to. And as I did, she pressed deeper with her four fingers. There was a moment of pain, a sensation of stretching, and the stretching sensation was replaced with a feeling of fullness. Her entire hand was inside me up to the wrist.

“Oh.!” She said. For a moment we stayed like that, motionless, neither of us believing that it had really happened. I felt completely possessed. She was inside me, and not just a finger tickling my anus; she was deep inside me. .

“It’s too bad you can’t see this,” she said. There was wonder in her voice. “All I can see is my wrist. My hand is all up inside you. It looks like I’m fucking you with my arm.”

“I feel . . . helpless,” I said. I feel . . .” I struggled for a word. “Connected. No, not just that. Owned.”

“Well, you are owned, honey. I just popped your cherry. Does it hurt?”

“Not at all. I was all stretched out anyway. And once you got past the knuckles, it’s smaller at the wrist.” A thought occurred to me. “You planned this.”

“Of course. You can’t just put your hand in somebody the first time you think of it.” She touched my cock with her other hand. “Did you come already?”

“I don’t think so,” I said.

“You’re soft.”

“I still need to get off. What about you?”

“I came when I pushed inside you,” she admitted. “A big one.”

“I’ve never felt anything like this before.”

“How does this feel?” She moved her fingers a little. I felt it in the front as much as in the back.

“I feel totally controlled. I feel like a puppet.”

We were like that for some time, each of us getting used to the new feelings. From time to time she moved her fingers a little, not going any deeper, just exploring the sensation. “I can feel every finger,” I said. “This has got to be a hundred times better than having a cock inside you. Not that I would know,” I added.

“Even a small wrist has to be bigger than the biggest cock.”

“And the fingers,” I gasped as she started to move them. “It’s too much; oh God! I’m gonna come!”

She put her other hand at my cock, not gripping it, just with a finger touching the tip. “Look,” she said.

I looked down between my legs. She had her hand to one side to give me a good view. My cock was completely limp, not more than two inches long. And as I watched, I came. It throbbed, and a white jet of sperm surged out. She started to move her hand inside me and another jet came out, bigger than the first. But my cock never hardened; it just twitched. I watched, not believing what was happening. She moved her hand an inch deeper inside me; I thought I would go crazy. Another big jet. She pressed a little deeper . . . It went on that way till I was completely emptied. The whole time, neither of us took our eyes off my limp cock

I spoke first. “I didn’t think that was possible.”

“That was amazing.”

“I came as hard as I ever came in my life. But I was soft.”

“So it didn’t matter, did it? You don’t need to get hard.”

“Not if I come like that.” I gasped.

“Good. Because that’s how it’s going to be.”