I closed the door and took off my shoes and suit, and stepped into the dress. As I began buttoning it up, I began to cry tears of joy, as I felt as if a huge weight had been lifted from my shoulders. I was at least was able to compose myself enough to put my male clothes back on and go to pay for the dress.
My wife and I lived in a quiet suburb, in a modest but nice home. We both worked normal 9–5 jobs and had a fairly happy life together. I keep writing in the past tense because everything has changed. Jill and I are still together, but not in a traditional relationship.
I was an aspiring actor, I was good and I knew it. The only trouble was I couldn’t seem to get that message across to any agents. Without an agent in that business, you’re nowhere. I had tried different coaches to try and unlock my potential. Some wanted to protect me from me by only letting me work on simple roles, others wanted to play Svengali and control my every move, and nobody seemed to really want to work with me for the love of the art form.
That is until I met Ben Green. Ben Green had been a very successful Broadway singer for many years. By successful, I meant he was never without work. He had a steady following but never became a household name. I started working with Ben about 11 months ago. He was the best coach I had ever worked with. He had the singular ability to unlock parts of me, that I didn’t know existed while maintaining an atmosphere of support and creativity. I had never considered myself anything other than heterosexual, but the sessions with Ben were so intense and he was so brilliant, that I began to think of him more and more.
I was actually sad when a session ended, yet so uplifted that when I left I practically floated home. Try as I might I couldn’t stop thinking about this brilliant man. I was madly in love with my wife Jill, but whenever she was out of my sight all I could think of was Ben. I felt so good about the progress that I was making by working with him, that any happy feeling I had, I associated with him. Jill would see my usually sunny demeanor go absolutely radiant after working with Ben. She would ask me about the coaching session and be extremely supportive of my progress.
Jill knew how miserable I was in my day job. I was working full-time in a middle management position with a company that manufactured men’s coats. Like most of that industry, my company was slowly fading into oblivion, as more and more retail stores bought cheap quality imported garments (to save a buck, and screw the customers). It was bad enough to have to be working in a profession that you barely could tolerate when business was good, but it was torture to go to work in the condition this company was in. Daily, I would receive calls from vendors wanting to know when their bills were going to be paid. I was working like a madman after work to get my acting career going. I figured that it was a race to see what would occur first, my company going out of business or a big break in my acting career. After working seriously on my acting for almost five years since coming back to it, I was becoming a little despondent…as I had yet to land a paying acting job. I went to graduate school for acting and did lots of small regional theater work immediately following school, but quit when I couldn’t make ends meet. After years of working a “normal” job, I got the itch and started pursuing it again.
After working with Ben for a few weeks I began to notice that I couldn’t wait to get back to see him the next week. The sessions became intoxicating like drug. The more I went, the more I wanted to go back. At the time I thought that perhaps that I had a small crush on him, as he was so kind and supportive of my efforts. I felt really confused, as heretofore any feelings of attraction I had experienced had all been for women. Despite my growing confusion, I couldn’t wait to see Ben every week. My acting continued to get better and my confusion deeper. He never touched me, he never even flirted, yet I grew more confused. Here I was a 32-year-old married man, and I couldn’t get my acting coach out of my mind.
About six months ago I was working with Ben when he asked if I knew of anyone who would like to audition for a musical. The producer was looking for a female with dance and singing experience for a musical. I asked Ben if he would hear my wife, Jill, as she was also a theater major in school and had kept up with jazz dance as a way of staying in shape. The following week Jill came and took coaching with Ben. He was very impressed with her and thought, that with a few weeks’ work she could be ready to audition for the producer. I began to see the excitement in Jill upon her return from working with Ben. She was just thrilled to be working on theater material again. As we were now both working with Ben, we grew closer than ever talking about our work, and how he was helping us.
At my coaching the following week, Ben indicated that perhaps I should consider taking a dance class, to help my movement on stage more graceful. I told him that I had taken jazz and tap as part of my studies in school, but admitted that I hadn’t kept up with them very well over the years. He recommended that I take a ballet class, as it would not only help with my movement but would really whip me into shape. After all, the theater is a very visually oriented business.
That weekend I was sitting on the couch eating some popcorn while reading a book on method acting when I broke a tooth. I called to get an appointment with my dentist, only to find out that he had retired. When Jill came home she told me that she had found a new dentist and I would find her virtually painless. Luckily the doctor could see me that afternoon, as my broken tooth had really started to throb.
Upon arrival at the dentist’s office, signed all of the normal charts and forms and waited in the very nicely decorated lobby to be seen. When the dentist examined my tooth, she indicated that she could build up the broken part of the molar with some new resin enamel and that I would be as right as rain. She turned up the “elevator music” that was playing in the background before she started working. Shortly after the music was turned up, I dozed off, and couldn’t remember a thing about getting my tooth fixed. I shortly woke up to my new lady dentist leaning over me as I lay in the chair. She smiled a brilliant smile and announce that I was free to go, but that I should schedule a follow-up visit for next week to check the bond on the repair. When I walked out of her office I felt better than I had in years. I felt like I had awoken from a whole night’s sleep, and hadn’t a care in the world. I practically skipped to my car.
Later that night Jill and I had a romantic dinner and began to talk of the week’s events. We later went into our den and shared a bottle of good wine. For the life of me, I can’t explain why, but I began to tell her of my confusion over Ben. Much to my surprise, she was not angry, and simply put it off as infatuation. She told me that she felt totally secure in our relationship, and was not at all worried about me straying. We made love that night like frantic teenagers, if anything my revelation made her more turned on than usual.
The following day Jill asked me if I would like to go shopping with her at the local mall. Normally I couldn’t think of anything I would like to do less, but for some unexplained reason, I said yes, and happily accompanied her. We spent the whole day looking at ladies’ fashions, as she was looking for a new dress for her audition, and needed to stock up on some “essentials”. On the rare occasion that I have gone shopping with Jill, I have vacillated between sheer boredom and embarrassment. Especially when she wanted my opinion on some new “frilly” she was about to purchase from the lingerie department. On this particular foray into shopping, I that I was having a blast. I was much more attuned to what matched, and what was in fashion. Jill and I shopped for nearly eight hours before stopping for dinner. The time had simply flown. I couldn’t remember Jill and I having a better time together. I did think the whole experience odd at the time, but whenever I thought about it a sense of pure serenity flowed into me.
Although Jill had been my best friend in the whole world since virtually the time we met, we were to my amazement growing even closer. Over the next few days, I would find myself calling her from work, to chat about some inconsequential matter just because I hadn’t heard the sound of her voice in an hour.
We both continued to study acting with Ben, and he complimented us both on the great progress we were making towards our acting careers. He continually preached that to be truly believable as an actor, you had to be able to pare away all of the external images that you have built of yourself over your lifetime, and be able to share the essence of your soul with the audience. Ben told me that I was getting very close to a big breakthrough, and as always, I left my session very encouraged and uplifted. I was a little concerned as this past session with Ben felt a little like a very painful therapy session that I had gone through in college. Nevertheless, I was so encouraged by Ben’s comments that I quickly put it out of my mind.
The next week Jill had her big audition and wore the dress that I had helped her pick out. She looked fabulous and sounded even better. The producer offered her a role in the show immediately. He said that the show would go into a workshop in a month, rehearsal in six, and with a little luck on Broadway in a year. The producer indicated that he had a few more important parts to cast and that he would be in touch the following week. When Jill came home she told me her marvelous news of being hired. I asked her what the name of the show was, and she said that it was as yet, unnamed. When I asked her what the show was about, she really couldn’t tell, as they had only had her read a few disjointed passages from throughout the show. She couldn’t even tell me who wrote the script, as it was anonymous.
The following week I went back to the dentist for my follow-up appointment. The dentist explained that the new resins that she had used were somewhat unstable unless treated a second time with a special ultraviolet light procedure that required me to remain relatively still for thirty minutes. She set up all of the equipment, and turned up the background music, explaining that it helped her concentration. Just as before I fell fast asleep, only to be awoken by my grinning dentist, who said she would see me in six months for a cleaning.
Things were going along fine for Jill and me. She was going to be in a big show, and I was really getting in shape with my ballet class. At 5’10" tall I had whipped myself down to 150 lbs. I had never felt better, and even though I had been eating like a bird, I never felt hungry. I had tons of energy, and I slept like a baby. Then something strange occurred…
I was out on my lunch hour and was walking around the neighborhood near my office and walking past a ladies’ dress shop. I suddenly had an overwhelming urge to go and look at the lovely dresses and accessories that were on display at the store. I walked in without the slightest hesitation and began to peruse the merchandise. I was amazed at the tremendous sensual feelings of the fabrics the dresses were made of much nicer than the wool suit I was wearing. I remember thinking that it was so unfair that men were made to wear rough wool suits, while women could wear such a wonderful variety of textures and colors. When a salesperson approached and asked if I needed help, I snapped out of my revelry, turned bright red, and walked back to my office wondering if I was having a nervous breakdown.
Ben had become much more to me than a drama coach, even though I continued to have disturbing fantasies about him, he had become a friend and confidant. I told him after my last coaching about the incident at the clothing store, and he reassured me that we had been doing work that gets very close to the heart of one’s psyche and that I had probably been very emotionally exhausted. He went on to explain that the emotional strain of such work often led people to temporarily do things that they thought were strange, but he urged me not to give up on our work, as we were getting very close to a breakthrough. I mentioned the episode at the dress shop to Jill that night at dinner. She thought it was cute and playfully suggested that I buy myself something. I was repulsed by the idea and dropped the subject immediately.
Two days later I went down to the lobby of my office building to buy a cup of coffee at Starbucks when my eye caught the latest volume of Elle magazine. Suddenly, as if my hands had a mind of their own, I was fishing around in my pockets for enough money to buy the magazine I had to have it. I read it cover to cover eight times before the day was over, I had an overwhelming need to know all there was about current women’s fashion and cosmetics. I thought I was really over the edge now and vowed to take a few weeks off from working with Ben.
I confided this new episode with Jill at dinner and she said that I was blowing the whole thing out of proportion. She explained that men often like Elle, and Cosmo so they could ogle the beautiful babes that grace the pages. She comes over and gave me a big hug, and explained that she thought my new awareness of the feminine half of the population was a sign that I was becoming a more complete and evolved person. She went on to say that she guessed that all of the work I was doing with Ben was really starting to pay off and that it would be a bad idea to take a break from him.
At work, over the next few days I found it very hard to concentrate, and once had to go to the men’s room, because I had gotten so angry with a coworker that I suddenly felt the need to cry…and didn’t want anyone to see me. Once in the men’s room, I sat in a stall and balled my eyes out for a good 15mins. I felt much better afterward, but couldn’t remember breaking down crying like that, except as a child. I did keep my weekly appointment with Ben and mentioned my recent behavior. He tried to reassure me that I was doing very important work with him and that it would be a tragedy to quit at this juncture.
The weekend came and Jill and I had planned to just chill out and spend quality time together. She was soon going to be starting the workshop of her play and wanted to make sure that we spent time together since it would soon be so scarce. She announced that we were to go shopping, as she needed a few new workout outfits. Without thinking twice I happily agreed to go with her. We were gabbing like a couple of magpies all afternoon, just having a great time.
We passed an outlet store for Hanes/Bali etc, and she stopped in to get some new underwear. Normally I would have waited out in the mall for her, but this time I skipped right into “forbidden territory” with her. Strangely, instead of feeling panicky or embarrassed I suddenly felt that feeling of serenity pass over me. She asked me what I thought of a pair of printed high-cut satiny panties as a joke, and I replied, as if from someone else, that I wanted a pair for myself. She chucked and inquired if there were anything else in this store that I required. As if in a trance I told her that I need a garter belt, stockings, and a bra also. With that, she merrily took me around the store and picked up a number of items, many of each. When we arrived home at the end of the day we had a dozen bags of purchases to bring into the house. As we unpacked the bags I asked Jill, why she had bought so much lingerie, as there appeared to be enough for a small army. She very calmly told me that they were for me.
I flipped, I mean, remember the whole shopping trip, but for the life of me, I thought it was some kind of a dream. Jill came up behind me, wrapped her arms around my waist, and cooed in my ear that the thought of me in sexy undies had her totally turned on. We stripped down to nothing and made love at a fever pitch for hours, although for the first time she decided that she would be on top. I have to admit that having in her in the dominant position was a lot of fun.
The next Monday I was walking around the vicinity of my office building on my lunch hour when I passed the dress shop again. Once again, an overwhelming urge compelled me to walk into the store. As if on auto-pilot I looked around the store at the lovely fashions, stopping many times to look at sizes and to touch the fabrics. But unlike the last excursion into this new world, this time I felt perfectly normal and at peace looking through the racks of dresses, tops, and skirts. Actually, I felt better than normal, I felt euphoric. My eyes fell upon a navy blue dress with a hem that fell to about mid-calf. I held it up to myself and looked in a mirror. The saleslady couldn’t remain a bystander any longer, she came up and asked me if I needed any help. Still, in a semi-daze, I asked her if she thought the dress was my size as if it were the most normal thing in the world.
I had inexplicably lost more weight overall, but for some odd reason, my pants had been feeling a little tight in the seat lately. The saleslady was very nice and offered to take my measurements. Upon measuring me the sales lady announced that I was a size 10 and that this dress should fit me perfectly. She then asked me to follow her to the dressing room area, where she escorted me into a room, and bid me try the dress on.
I closed the door and took off my shoes and suit, and stepped into the dress. As I began buttoning it up, I began to cry tears of joy, as I felt as if a huge weight had been lifted from my shoulders. I was at least was able to compose myself enough to put my male clothes back on and go to pay for the dress. As soon as I was back on the street with my shopping bag, reality set in….I had just gone into a dress shop, tried on, and purchased a dress, and now I had to go back to my office with a bag from a well-known ladies’ dress shop. No one at work said a thing, as I guess they thought it was a gift for Jill…although I did detect a few sideways glances from some of the secretaries as I walked to my office.
READ THIS STORY — Getting into acting as a woman
