Masseur to Masseuse

0.Chapter 1

Part 1

I've been an unlicensed masseur for a number of years. I offer my services by word of mouth or by options such as Craigslist. I have a natural affinity for it, and I've always found it enjoyable to help someone feel better. Naturally, there are some clients that expect more than just a massage, and there are some clients that are not happy simply because I'm a man. I may get a call to massage them once, and they may enjoy it, but hardly ever will they call me for repeat business. Until recently, this wasn't really a problem. I had my day job which paid the bills more than adequately, plus I had a tidy nest egg set aside in the event of a business downturn.

Things went along in this way for a number of years until the business downturn finally reached me. My boss had to let me go, but it was an amiable parting. We had always had a good working relationship, and he made sure to let me know that I was on the short list to rehire as soon as business picked back up. At the time, I didn't think it would take that long, so we parted with a handshake and a smile, and a promise to keep in touch with each other. As I was single, with a rather minuscule social life, I could live on my nest egg for several months, as long as I was careful. I resolved to treat the time as an unpaid vacation.

Also during this time, I decided to maybe branch out and put a little more focus on my massage activities. Now that I was able to take clients in the day, I let it be known, again on Craigslist and by word of mouth, that I was available to take care of their stress and body aches. I wasn't exactly flooded with new clients, but I did pick up a few new people and some of them even became repeat customers.

As time went on I began to seriously consider doing massage full time and foregoing my previous technical career. I gave it long thought and finally decided to take the plunge, using a portion of my nest egg to cover the required 9-week class and the state license examination. In our class of eight, I was not the smartest person there, but my instructor said I certainly had the best touch.

All of my classmates were planning on taking positions in physical therapy, working for hospitals and such. I was the only one looking to do actual relaxation and stress relief massage, so I thought that would be a leg up for me. As an actual licensed therapist I planned on applying with some of the local massage studios for a full time, or a contract type position. This I did, but immediately began running into problems.

As part of the application process, I would always give a massage to the owner, so she (it was always a female, a clue I should have picked up on) could check my technique. It was invariably a success and I invariably never got called for a second interview. Finally, after the fourth attempt, and already seeing the inevitable writing on the wall, I decided to confront the issue directly and I asked the owner (her name was Jennifer, Jen for short) what my chances were. She had me sit down in her small office and we chatted.

Jennifer leaned back in her chair and sighed. "Matthew, I won't make bones about it. Most of our clients, both men and women, simply prefer a female for massage. Your technique and your empathy are excellent. And, truly, most people wouldn't notice your sex once you began working on them. But that initial meeting always seems to put them off."

She leaned forward in her chair as I fell back in mine, suddenly seeing the obstacles in front of me. Her arms resting on her desk, she waited for me to reply. "Couldn't you perhaps just take me on on a trial basis? Say a month or so, just to let clients get used to the idea?"

She shook her head sadly. "No Matthew, I'm sorry. Once we lose a client, that client almost always stays lost. We work hard to keep the clients we have and I don't want to give them an excuse to go looking elsewhere. I'm sorry."

I stood then, as there seemed to be no reason to continue the conversation. She stood as well and held out her hand for a friendly departure. As I took her hand, I asked one final question. "Is there anything I can do that would make it possible for you to hire me?"

"I'm sorry Matthew. If you were a woman, I'd hire you in an instant, you seem to be perfectly suited for this work. But you're not, so...". Her voice trailed off, and I released her hand, mumbled my thanks, and left, walking through the lobby into the bright sunshine, which totally did not match my mood.

Part 2

After the last interview, I continued with my life much as before, taking the occasional client from Craigslist, and generally just getting on with my life. However, Jen's last words kept echoing in my head. "If you were a woman...". The more I thought about it, the less outlandish it seemed. Perhaps it was just desperation nudging me along, but I tried to consider it dispassionately. I was slim, not very muscular at 140 pounds, and not excessively tall at 5'5". I didn't have any relations nearby that would be shocked at such a change. I thought I might (emphasis on "might") be able to do it, but, even if I were willing, I had no clue how to begin.

So when in doubt, turn to the Internet, that compendium of all things you would never ask the public librarian. I entered "male to female" in the search engine and the first thing I came up with was a photo page of 25 people who went from male to female. As I scrolled through the photos, I was surprised, pleasantly so. These people, in their male guise, some of them could have been me. And in their female guise, they looked wonderfully feminine.

It was the beginning of a whole new world to me. I ended up spending hours looking through the various search pages; learning about makeup, what to buy, how to use it. Clothes and what fits a man even though it's made for a woman. Shoes. Lingerie. It was quickly becoming at once overwhelming and also fascinating. And the more I looked and studied, the more my goal might actually be possible to realize.

But the more I studied, and the more feasible it seemed to be, I kept bumping into one inescapable fact. I was a man, I had always been a man, and I had no idea how to act like a woman, or better yet, how to actually become a woman. For two days the problem played around in my mind. Then one night while flipping channels, I came across one of those home shopping shows. On the screen, a woman was demonstrating how to apply a particular make-up to a woman's face. And I knew what I needed: a coach!

Or more accurately, a teacher, a woman who wouldn't mind teaching me what it's like to be a woman. The more I thought about it, the more reasonable, the more necessary it seemed. And as I thought about it, the perfect woman to do this came to mind.

Her name was Melinda and she'd been a classmate of mine in college. She was a cheerful, happy, lovely lesbian, and unaccountably we'd become and remained good friends. We didn't have as much contact as we'd had previously; careers, family and life in general just seemed to get in the way. But we'd kept in touch through the modern miracle of Facebook and we still got together for lunch every now and then. I decided it was time to suggest a dinner date. I didn't stop to think how crazy my idea might sound to her. If I thought about it too much I'd have probably chickened out.

The following Monday we were having dinner in a small bistro that we both enjoyed. We talked and laughed, sharing details of the things we'd been involved in lately. She told me of her partner, and how the two of them were getting along. I gave her updates of my family, what they had been up to lately. We shared gossip on some of our mutual friends from our college days. Finally, as our plates were cleared away, and we settled down to sip our wine, she brought up a subject that I hadn't really been sure how to broach.

"I saw on Facebook that you were let go. Have you found another job? What are you doing now?" she asked. I sensed a touch of caution in her voice, as though she didn't want to bring up a potentially sore subject.

I smiled easily and hung my head somewhat bashfully. "Well, I've been doing some massage through Craigslist. I even did the training and got my license. It's keeping me in a positive cash flow, but just barely." I took another sip of wine and continued. "I've tried to get on with some of the local massage businesses, but I've been turned down at each one."

She looked puzzled. She had been the recipient of more than one my massages back in the college days so she knew how good I was at it. "Why? I would imagine that they would snap you up like that!" she said, snapping her fingers for emphasis.

"It's because," I said slowly, "I'm not a woman."

She looked at me, her eyes wide and her mouth dropping open. For a moment, there was just a silence at the table. And then she started to giggle, and then covering her mouth as the giggle gave way to full blown laughter. She finally got herself under control, her big grin matching my smile. She shook her head, her soft brunette hair waving back and forth. "Oh Mattie, that... that is just too rich!" She started giggling again, and I thought she was going to break out in laughter a second time, but she got control of herself.

Finally, with a deep breath, and a long exhale, she quieted down. But I could still see the mirth in her eyes, and her cheeks were a rosy red. She raised her glass for a toast and said, "Here's to those that just don't know any better." I smiled, raising my own glass and touching it to hers in a soft 'clink'. We both took a sip, then set our glasses down.

"So," she asked, a mischievous grin on her face, "what are you going to do about it?"

It was my turn to take a deep breath and let it out slowly. I took another sip of my wine and, looking straight at her I said, "I need to become a woman. And I would so appreciate it if you could help me."

Part 3

It was two weeks later, and Melinda had spent two or three hours each day giving me lessons in how to be a woman. Her partner, Zoe, I was going to have to nominate for saint-hood. I cannot think of many people who would willingly give up the love of their life for 2-3 hours a day just to help an old college friend. The lessons were intense, sometimes funny, often awkward, but always enjoyable. Fortunately, Melinda was a girly-girl; she enjoyed dressing up, make-up, jewelry, and being feminine. She was the 'female' in her couple, while Zoe was the 'male'. They were both attractive women, just attractive in different ways.

Carefully, patiently, and with good humor, Melinda coached me in the techniques of applying makeup and doing my nails. At first, I was simply overwhelmed with all the minutiae that a woman has to deal with. Earlier in my life, I had (somewhat jokingly) made the statement that "it is so much easier to be a guy." Now that I was actually beginning to live it, I realized that it wasn't just a remark to be tossed off flippantly. Women go to great lengths to look beautiful for their friends, their lovers and the strangers they pass in the street. And I would need to learn the same techniques and go through the same daily process if I were to succeed as a woman.

The first time that my face was completely made up, sitting at Melinda's dressing table, I was amazed at the transformation. The rather ordinary looking man had been replaced by an attractive woman. My eyes had been highlighted by eye-shadow and mascara; my lips were no longer pale and thin but had become dark and inviting; no trace of beard was showing, and my skin appeared to be glowing from the inside, with the slightest dusting of blush across my cheeks. My nails were only slightly longer than I wore as a man, but now they were covered with a pale red polish, almost pink. The color was subtle but undeniably feminine. I sat there in wordless wonder as I just stared at myself, eyes wide as I took in my new image. Melinda stood behind me, resting her head on my shoulder and looking at my face in the mirror. She smiled softly and asked, "Is this what you expected Mattie?"

I sat there, just staring into the mirror, my fingers pressed to my cheek, the nail color complimenting the color of my lips. I shook my head softly, just barely moving. Then I shifted my eyes from myself, to her reflection. Whispering softly, almost afraid to break the mood, I said "I really wasn't sure it was possible." A large breath I hadn't realized I'd been holding came out in a long exhale. Softly, I murmured, "Thank you Mel... it's... " and my words trailed off. The right words didn't seem to be there. She just smiled and gave me a soft kiss on the cheek

When the makeup process had been learned, we moved on to clothes. Melinda had picked up some clothes for me from Goodwill; heels, pumps, flats, jeans, blouses, dresses, skirts, bras, panties. She gave me a sheet (from the Internet of course) that showed what women's sizes could be worn by men, and the men's size that they relate to. The first time I slipped the panties over my hips and the bra around my chest, it gave me a shiver. My initial reason to do this was simply so I could work at what I enjoyed doing. But now, as she and I moved deeper into this new world, I found that I was enjoying it, that appearing as a woman pleased me, even excited me, in a fashion that was entirely new.

On Melinda's advice, I ordered breast forms (a modest b-cup), a corset and a gaff. The last item was one I'd never heard of before; it turned out to be a reinforced panty that would effectively hide my penis once it was tucked between my legs. In all honesty, I was not looking forward to wearing it, expecting it to be very uncomfortable. But, once it was in place, with everything tucked away, it was surprisingly comfortable and smoothed out my front exactly as advertised.

The official lessons went on for another two weeks or so, though they never really stopped. (Truth be told, I'm still learning.) How to walk, how to wear heels without killing myself, how to get in and out of a car while wearing a skirt or a dress, how to sit (no more sprawling on the couch with the legs spread wide), how to behave around men, how to recognize flirting (from both sexes). Some of these things I could practice; some would just have to wait until I was in a real-life scenario.

Finally, after a month or so of teaching, learning, training, trying and growing, Melinda judged I was ready for the "real world". Zoe had been keeping an eye on Melinda's lessons and (I learned later) had offered some "behind-the-scenes" advice on some small things she'd noticed, particularly when I would slip into male mannerisms. They had decided, between themselves, that I was ready to go out in public as a woman. (We had done some public outings in simple ways: walking through the malls, doing a little shopping, but nothing too extensive.) So for my "graduation", we were going to celebrate at a local place that served both gay and straight women.

Part 4

The club was called "Out and About" and it catered primarily to professional women. As it was a Saturday, the clientèle was a bit younger and a bit more party-friendly, so I wasn't entirely sure what to expect. As a male, I had never been a party person, but as a female I found that more than just my dress style was changing.

Melinda and Zoe had chosen my outfit for me this night. Another part of my "graduation", they had purchased a beautiful outfit. It consisted of a silky gold, sleeveless top that clung to my feminine form and plunged just enough to give a hint of cleavage. A(relatively) modest pleated skirt, a dark chocolate brown color, that came to just above my knees. A new bra and panty set, also chocolate brown, and new stocking and heels. Earlier that day I had shaved all the hair from my body except for my eyebrows, and then they had taken me to the beautician that they used, giving me a manicure and pedicure, and painting my nails to match my outfit that night. My hair had also been trimmed and shaped in a much more feminine style. It wasn't as long as I wanted it to be, but it was longer than I'd ever worn it as a man. It had also been washed and blow dried until it gleamed.

Throughout the month of these lessons, and particularly throughout this day, I found myself in almost a constant state of excitement. What had once seemed like a simple thing to just find employment doing something I loved had changed. I found that I enjoyed dressing as a woman! The work that I had to go through to feminize myself each day at first had bothered me greatly, partly due to its unfamiliarity and partly due to the amount of time it took. But as the unfamiliar became familiar, and as practice made things easier, I found that I was enjoying it, even looking forward to it each day! I shook my head, smiling inwardly at how much I had changed, and in so short a time.

Further, I had learned so much about being a woman, just from those brief excursions we had already made in public. How women are treated differently in the stores, how men's eyes would follow me as I walked through the mall, even how other women would evaluate me! It was in so many ways a shock. I felt like I'd gone through life blind, and had only now had my eyes opened. It was an ongoing voyage of discovery.

"Hey, you awake there girl?" Zoe's voice took me by surprise. I blushed as I realized we were at the door. I'd been so lost in my reverie that I hadn't been paying attention to where we were going. And now we were here.

I smiled, my blush hidden by the darkness outside the club. "Yes, I'm good, thanks Zoe. Just thinking about how I got here, how much everything has changed!"

She gave me a warm smile, kissing my cheek as Melinda held the door. And we three, looking for all the world like three girls out for a good time, entered the club.

I laughed lightly to myself as we went in even though I was still a bit apprehensive. "Out and About" is a lovely club, a wonderful place to hang out, and consequently can be very crowded, though we'd timed it to get there before the rush. However, there were a number of people scattered about. Knots of women were gathered here and there talking, laughing and drinking. As we three came in, there was the briefest lull in the conversation as the automatic evaluation of the newcomers began. I felt my heart beating faster, but I relaxed in the knowledge that both Melinda and Zoe had vouched for my appearance, and I trusted them implicitly. I didn't know what I would do if someone recognized me for what I was, I would just have to wait and see.

We found a small table off to one side of the dance floor. Only a few couples were dancing, bodies close and touching to the slow music coming from the sound system. I sat down carefully, looking around, taking it all in. In no time, a waitress had come up to us and taken our drink order. Melinda and I both ordered strawberry daiquiris, Zoe ordered a martini "extra dry". The waitress smiled at each of us, then headed back to place our order.

For some reason I couldn't stop smiling. I don't know if it was nervousness or excitement. But as I moved my gaze between Melinda and Zoe, and looked around the club, I was very much enjoying the experience, enjoying the atmosphere. Melinda leaned in close to me, smiling also and whispering softly, "Are you all right Maddie?" In my female guise, I was now Madeline. It had been Zoe's idea, knowing what Melinda's pet name for me was. It was a simple jump to go from "Mattie" to "Maddie" to "Madeline".

I nodded, still smiling, still feeling my heart beating quickly in my chest. Murmuring softly, working to pitch up my voice to be a bit more feminine (something I'll always be working on) I replied, "I'm wonderful. I just find it so hard to believe I'm here!"

Zoe smiled, chuckling softly. "You know Melinda and I have been here before. We know a lot of the girls here, but you're a new quantity. I imagine some girls will be hitting on you before the night's over."