My name is Jeff, and making music is what makes my life worthwhile. I have a Bachelor of Music Education degree and a Master’s degree in keyboard. While in college, my faculty advisor suggested the education part, because with it I could teach music in grade and high school. Perhaps my advisor had heard my performances and thought that I couldn’t make it as a concert pianist. I was good, but maybe not THAT good. Perhaps she was right, because I couldn’t find a full time job as a performing musician when I graduated. Well, I did what a lot of other unemployed graduates do in like circumstances; I went to grad school.
Suggesting the education part turned out to be a great idea. Right before I graduated, I started the process of getting a teaching certificate, and found out that I still needed a few education courses. That was another reason I went to grad school. Once I had my masters, I completed getting my certificate. I started looking for a job as a pianist. OOPS! While I had some gigs as a backup musician, I still did not earn enough to move out of my parents’ home. While kicking around the job market, I also looked into a teaching position with my teaching certificate in my hot little hands,
Music education programs at most schools do not need a full time teacher. So I looked over the requirements for an endorsement for my certificate, so I could teach a core course in addition to music. I only needed one additional course in History and two courses in English to get endorsements in both. So, it was back to the local community college, where I picked up the necessary credits to get the endorsements. Then it was back to the job market.
Those endorsements did the trick, and I found a position at the local high school where I taught freshman English, Band, and Chorus. Having a Masters was an additional bonus, because it kicked me up into a higher salary bracket. At last, enough to move out on my own. While I was in the process of packing and moving, my Mom said, “Don’t forget to pack ALL of your clothes.”
The last comment referred to my “hobby” of occasionally cross-dressing. While my parents tolerated this, it appears that they didn’t want to be reminded of it with a closet full of womens’ clothes. Luckily, I had rented a two bedroom apartment, so I had enough room for ALL of my clothes and enough room for the piano which my parents bought for me when I was only six. One of the pleasures in life was to get dressed in a gown, high heels and make-up and pretend that I was this gorgeous concert pianist and play a full program while enfemme. This had been mostly limited to those evenings when my parents were out. While they tolerated it, they just didn’t want to see it. My dressing was curtailed during college because I shared a room and didn’t have much spare money for clothes.
Since I considered myself to be a musician, even in grade school, I decided that I could let my hair grow. My hair grew, but I didn’t. I stopped growing during my sophomore year in high school and only stood 5 feet eight inches. I topped out at 135 pounds. While most of me remained skinny, by behind was not. Perhaps it was all of that sitting while practicing the piano.
I was too small for most sports, but I could run, so during high school I ran on the cross country team. I wasn’t all that good, just good enough to stay on the team. The funny part of all this was that as a team member, I was almost considered to be a “jock,” and I wore my letters proudly.
While in college, I met Amy. She was in the music program and took voice. We dated a bit but didn’t see much or each other after graduation. Imagine my surprise when I ran across her in my hometown. She told me that she had taken a job here, and a second part time job teaching chorus at St. Anne’s, a local girls’ high school. We had the occasional date and spent a lot of our free time together.
That November, she had the biggest smile on her face. “I have a soloist position for a Christmas Program. The Messiah. Maybe you could help me rehearse.”
“Sure,” I said, “I still have my piano at my apartment, and a keyboard. Maybe you could come over to my place on Friday evening. I can order some takeout, and we can rehearse after we eat/”
“That’ll be great,” she replied. “How are you stocked for music?” Well, as you could imagine, as a musician, I have a great quantity of music, most of it in cabinets and shelves in my second bedroom. By the way, the dresser and closet in this room had my “other” clothes. There was no bed in this room, just a couch, but additionally there was a low table with a mirror that I used as my vanity.
That Friday, I came home as quickly as I could and cleaned up the apartment. I made sure that my womens’ clothes, shoes and make-up were safely put away. At least I thought safely. I ordered a pizza, and it arrived about the same time that Amy showed up After we ate, I said, “Let me get my copy of the Messiah,” and I headed for the second bedroom. She followed me closely. My mind raced to try to remember if I had put away all of my girl clothes and make-up. While I really didn’t want her in the room, I could not think of an excuse to keep her out.
She immediately headed for the music collection and pulled out some scores. “Maybe we could do some of these in the future,” she said. I just grunted in reply. After a while, she started looking around the room. Her eyes fell on my sort-of vanity, and she walked over to it and began to study it with interest. Luckily, all of my make-up was in a box under the table. She reached over and turned on the lights beside the mirror and sat down. I could just about see the wheels going round in her head, as she appraised the situation, but she said nothing. A few moments later, she turned around and took in the rest of the room. “You are lucky having this second bedroom. It gives you a lot of closet space.”
I was beginning to get nervous, and I suggested we start rehearsing. She stood up, but rather than walking to the door, she headed toward the closet. I could not think of anything, except to hope that she would head out of the room. No such luck.
She slid open the closet door. I just groaned. I could see our future together disappearing in a flash. There, hanging in the closet, were dresses, skirts, blouses, slacks, tops and coats. The floor of the closet was covered with shoes. Not a single piece of male clothes. She turned to me with a questioning look on her face, which shortly turned to a smile. “Yours?” she asked.
“Mine,” I managed to squeak out, not being able to come up with an explanation that would hold water. .
“I’d like to know about this,” she said sweeping her hand around.
“No, I don’t think you would,” I stammered.
“Yes, I would. We’ve been friends for a long time, but I would never have suspected this. Not that it’s bad. Just unexpected. So, what gives?”
“Well, sit down, and I’ll try to explain it to you.” I really had expected to see her race out of the apartment, but she hadn’t. Instead, she sat down on the couch, waiting.
“I like to cross dress,” I managed to say.
“Obviously,” she said, nodding at the open closet door. “Why?”
“I really don’t know, I just sometimes feel like being a girl. I rather like being a girl.”
“I never believed you were gay, considering all the times we slept with each other,” she said in a quite voice. “Are you bi?”
“I don’t think so.”
“I’d like to see you as a girl,” she said.
“Maybe, some day,” I muttered, thinking that “maybe” might never come. No such luck.
“No, not maybe,” she insisted, “NOW!”
I just sat there, thinking that this was the end of a wonderful friendship.
She grabbed my hand and pulled me up from the couch. “Showtime!” She exclaimed. “I’ve seen your clothes,” she added, “do you have undies and other unmentionables?
I nodded my head slowly.
“In that dresser?” she added. Again, I just nodded my head.
“This I’ve got to see.” she exclaimed triumphantly, and she walked over to the dresser and started opening drawers. “Wow!” was her comment as she picked up some panties and a matching bra. “You’ve just GOT to wear this for me. Start stripping!” she commanded.
I slowly began removing my shirt and pants, and paused before removing my shorts. “Don’t try to be modest,” she observed. “after all, I’ve seen you naked lots of time.”
She stopped for a moment, and observed my hairless body. “I always assumed that you shaved your body because you were a runner. Now I know differently.” she observed.
She handed me the panties. “I need a gaff first,” I explained, and I reached in one of the drawers. I slipped up the gaff and then the panties. She then handed me the matching bra.
“How do you fill it up?” she asked, looking at the empty cups.
“Breast forms,” I replied, “second drawer down. She reach in the drawer and pulled them out.
“Wow, they feel real,” she said.
“They ought to, for what I paid for them,” I quipped. This brought a smile to her face.
“What’s next?” she asked.
“Waist nipper and pantyhose,” I managed to say, “I don’t suppose that you’d be satisfied with a pair of slacks and a blouse?” I hopefully queried.
“You’ve got that right,” she said, with a smirk on her face.
“Then in that case, a slip.”
“Full or half?” was her next question.
“Depends on what I’ll wear. If it’s a half slip, I’ll need a camisole.” She handed me a full slip with lace at the top and the hem.
I put on the pantyhose, waist nipper and the bra. I slipped the breast forms in the cups and jiggled around to get everything in place. I could feel that I was getting aroused, but thankfully the gaff was doing its job, albeit painfully.
She looked at me with a smile on her face. “I’ll pick out the dress,” she asserted, and she pulled out an emerald green dress with a flared skirt. “This ought to do the trick.”
I lifted up my arms and she slid the dress over my head. I pulled it down and wiggled to get it to sit right.
“Looking good,” she said, “now for some shoes. Have any favorites?”
“Black patent leather, with the three inch heels.” She rummage around the shoes on the floor of the closet, pulled out the shoes, and handed them to me. I put them on.
“Make-up! I assume that you know how to do make-up.”
I was tempted to say no, but I didn’t think it would fly, so I sat down in front of my makeshift vanity and pulled out my box of make-up. First, I brushed out my hair and pulled it back in a ponytail. I then began to put on my face, foundation, powder, blusher and the like. I then began work on my eyes. I decided that green eyeshadow would work, and spent a considerable amount of time to get it just right. I finished off my eyes with some mascara. A little work with an eyebrow pencil gave my eyebrows a more feminine look. I then outlined my lips, and filled them out with lipstick.
“Stand up, and let me see.” demanded Amy.
“Turn around,” she next demanded, and I obliged with a swirl.
“Wow.” she exclaimed, and took my hand. “Let’s go in the living room, and start on some music.”
“Wait,” I said, and pulled the rubber band out of my ponytail, and let my hair fall around my face, after which I tucked it behind my ears.
I smoothed the back of my skirt and sat down at the piano. “Wow, you do that like a real girl. Nobody would think that you are a guy in a dress.” I just grunted.
The next few hours were spent with George Friedrich Handel. It was pleasant, with Amy there and me looking like a girl.
At ten o’clock, I turned to her and said, “It’s ten. We have to stop, so the neighbors don’t get mad. I don’t want them coming up to complain and to see me dressed. They don’t know about my hobby.”
I got out some wine, cheese and crackers and we sat down on the living room couch. Amy sat close to me, and I put my arm around her shoulders. Suddenly, I felt her had under my skirt, moving up my thigh. “Hey,” I said.
“I had so many guys put their hand up my skirt, I just wanted to feel what it was like, and for you to feel it,” she said. “How does it feel.?
“Good,” I answered, “but it becomes painful with the gaff.”
“Then take it off,” she responded, “and maybe take off the dress, we don’t want to have to send it to the cleaners.”
I turned and Amy unzipped me. I pulled the dress off, reached under my slip, pulled my pantyhose, panties and the gaff down my legs, and then stepped out of them.
“Come on,” she purred. “Let’s go into the bedroom. I’ve always wanted to make love to a woman.”
“But I’m not,” I responded.
“Close enough. How’s your tongue doing?” she chuckled. “By the way, what is your girl name?”
“I don’t have one.”
“How about Jenny?”
Hand in hand we went into the bedroom. Sufficient to say, it was different and wonderful.
Thereafter, we practiced several times each week, and I dressed each time. Amy told me she really liked it that way. I was very happy she did, because I liked it as much as she did.
Finally, it was the night of the performance. Amy came over to my apartment at about 3:00. “Why are you here so early?” I asked.
“Well, I thought we could eat together, and then get you ready.”
“Ready?” I asked.
“Yes, I want you to wear that green dress, and I brought a red scarf to go with it. Christmas colors, you know.”
“But I’ve never been outside dressed,” I complained.
“No time like the present,” she said.
“But what if people point at me and announce that there’s a guy in a dress. I might get arrested.”
“That won’t happen. You look too convincing,” she reassured me.
“But what if I have to take a pee? It’s a long performance. Where do I go?” I said frantically.
“Use the lady’s,”
“But if I’m discovered I’ll be arrested.”
“Then don’t get discovered. Just make sure you sit to pee.”
“But my voice.”
“Then don’t talk. Anyway, if you do talk, keep it short. You’re a high tenor. If fact, your voice is a lot like a woman’s. Keep your voice high, use head tones, and speak softly,” she explained.
“Do it for me.” she said, “I’ll make it worth your while later.” I wasn’t sure about the alternative, but I didn’t think it would be good or that I would like it.
So, I wore my green dress, the red scarf from Amy, a black wool coat and a black purse. Both of us had a score, Amy because she was a soloist, and I because I liked to follow the score during the performance. I had my ears pierced a month before, and Amy produced some cute snowman earrings for me.
My first time outside, enfemme. The first thing I noticed was the cold breeze on my legs and up my skirt. I mentioned this to Amy, and she just smiled as we walked to her car.
We arrived quite early, because the conductor wanted to go over some parts and to warm up the voices. I noticed that there were a lot of red and green outfits among the choristers. I was just standing there, score in hand, waiting. A woman with a clipboard in her hand walked up to me. “Soprano or Alto, dear?”
“Oh, I’m not singing. I’m Amy’s friend, and we came together,” I replied.
“Well, I saw that you have a score, so I assumed. . .”
“I haven’t practiced with the chorus, so I don’t think I should sing.” I responded. “I just like to follow along during the performance.”
“We have a few walk-ins, if you’d like to sing. Have you ever sung the Messiah? she asked.
“Yes, quite a few times,” I answered.
“I hate to ask this, but do you read music?”
“Yes, I have a bachelor and a masters in music, and I teach music” I replied.
“Well, then, back to my first question, Soprano or Alto?”
“Alto, but I’ve also sung the tenor part, if that matters.” I volunteered.
“We can always use tenors. Come over to the piano, and let me hear your range.”
“Okay,” I replied. I didn’t see a problem because I have a good range.
She seemed to agree when she checked me out. “You have a good strong voice, and a good range. How about singing tenor? You won’t be alone. We have some other women singing tenor, because we don’t have enough men volunteering to sing.”
Amy thought it was hilarious that I had been “roped into” singing the tenor chorus parts. Amy sang beautifully and, in general, the performance went well, or as well as could be expected from a volunteer chorus. In any event, the audience loved it.
After the performance, the singers and musicians were treated to punch and cookies. The lady with the clip board kept looking at me. I was afraid that she had “read” me, but Amy explained that she was impressed with my voice, and wanted me to sign up for later performances, and maybe try out for a solo.
“If you do, you’ll have to do it as Jenny,” Amy said with a smirk, thinking it would bother me.
It didn’t. In fact, I liked being Jenny, and looked forward to it. As I said, making music makes my life worthwhile. If I do it in a dress, that’s okay, well, maybe more than okay. An added plus is that Amy seems to like it too.
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