Gene or Jean? - Part 6 - How I got a job wearing a dress

Gene or Jean? - Part VI - How I got a job wearing a dress.
By Pentatonic

Chapter 38 - The Winter Carnival.

The college sponsored a Winter Carnival every year near the end of January to give everyone a chance to blow off a little steam. There were all sorts of activities such as figure skating contests, snow man building, and even sleigh rides. Some of the frats and sororities had booths with food, hot cider and cocoa. Others set up carnival type of games. The college even cancelled classes for Friday. Naturally, my presence, as the SRS Halloqueen, was requested, and because of my position, RLE didn’t object.

“I don’t have anything to wear,” I lamented to Sylvia.

“Said just like a woman,” she responded. But in my case, I didn’t. My feminine wardrobe was limited by where I could keep it. So the girls and I went shopping. I was able to borrow a white fake fur trimmed parka, but I had to buy ski pants and snow boots.

Suitable attired, and wearing my Halloqueen sash, I was assigned to SRS’s booth, selling cider and cocoa. I was in the booth, with only two other girls, when I spotted Frank, my roommate, heading over. Panic. “I have to get out of here,” I said. I didn’t want Framk to see me.

“You can’t leave now,” one of the girls said, “we’re too busy.” So I ended up serving Frank a cup of hot chocolate. He was too busy ogling the other girls to make the connection between me as Halloqueen and his roommate, but that was about to change.

Two additional girls arrived to man the booth, and one of the girls said, “We’re okay now, why don’t you take a break.” It was then that Frank came up to the booth again.

“Hey, Halloqueen,” he said, “why don’t you and I walk around together.”

I hesitated. “Go ahead,” one of the girls said, and I took off my apron and stepped out of the booth.

As Frank and I walked we made the usual small talk. When I mentioned where I was from, he said, “My roommate’s from there. Do you know him?”

“Yes,” I answered.

We talked about the courses we were taking. While I well knew what he was taking, I feigned interest in his courses. When he asked me about my courses, I didn’t think about it, so I answered him.

“My roommate’s taking the same courses,” he commented.

‘Oops,’ I though, maybe I’m giving him too much information.

We talked about me being the Halloqueen and what I did as Halloqueen. “I go to all of the school functions and sorority functions,” I answered him.

“Yeah, I saw you at the Christmas Dance.” he commented, “you really looked foxy in red and green. That slit up your skirt was really sexy.”

“That was the whole idea,, or at least the sorority’s idea.” I responded, “It wasn’t mine.”

“Hey,” he said, “don’t they say, ‘ if you’ve got it, flaunt it,’ and you’ve got it.”

“I’ll take that as a compliment,” I said, smiling at Frank.

“You ever talk to my roommate about why he doesn’t go to dances and suff like that?” Frank asked.

“We may be from the same hometown,” I answered, “but that doesn’t mean I’d ask about stuff like that.”

During our conversation, I let slip some more facts which connected me, the boy, with the Halloqueen. Frank’s grades may leave something to be desired, but, as I said, he wasn’t stupid. Then, it came to him. He stopped walking and turned to look at my face.

“Ahh, eer,” he mumbled. He then found his voice. “You’re my roommate!” he declared. I had to admit that he was correct.

“How come you never told me?” he said.

“I knew that you didn’t like cross-dressers,” I said in the nature of an explanation.

“Yeah, maybe, but right now I like a certain cross-dresser,” he said as he took my hand in his. We continued to walk. Frank seemed very happy to show me off to his friends, like I was some trophy.

That week, I was tutoring Frank, and he said, “How come you never wear a skirt here?”

“I don’t think it would be a good idea,” I said, “anyway, it takes me a lot of time to look like a girl.”

“Maybe so, but you’re really good at it,” he said, “all of my friends were impressed that I was walking around with the one and only Halloqueen.”

I did, however, dress up for him, to satisfy his curiosity. “You really look good,” he said, “If I didn’t know better, I’d want to kiss you.” He paused, still looking into my eyes, and then said, “What the heck?” and he kissed me.

“You kiss like a girl,” he said.

“I didn’t think you’d like it if I kissed like a boy,” I responded.

“Well . . .,” he said.

“No matter how I kiss, just remember that I have a very jealous girlfriend.” I said, “and I don’t think that I’m gay.” However, after swearing me to secrecy, Frank admitted that he was.

Chapter 39 - Valentine’s day.

Like the prior dances, the sororities and frats were hosting a Valentine’s day dance, and as Halloqueen I had a role in it. The first problem: What to wear.

“Something red and slinky,” suggested Rachael.

“With a slit up the side,” added Sue.

“Great,” I said, “but I don’t have anything like that. You know, I could wear the white dress I wore on the float.” The girls didn’t like that idea.

“Shopping time,” Ann declared. “Get dressed, and wear your corset.” When I was suitably attired, we headed to a discount dress outlet. Once there, the girls went directly to the cocktail dress section. Rachael was the first to strike pay dirt. She came up with a red cocktail dress that was a little shorter than knee length. The main asset, however, was a slit up the left side. She handed it to me and directed me to try it on.

It fit.

Rachael’s discovery only encouraged the others. As always. my opinions were not solicited, and I was told to just stand there, try on dresses, and be quiet.

Sue found a pink dress with a full skirt. “This would be darling with her red hose,” she suggested.

A slinky pink dress, with a slit was then found. The hem of this was just below mid-thigh. Way too short, I opined. I was ignored.

After a lot of conversation, the pink one with the slit was chosen, probably because I already had red lingerie.

The procedure for the Valentine’s dance was much like the Christmas dance. While sitting in the kitchen, I noticed that Sue was using a lot of makeup on my face. “Go easy on the makeup,” I said, “I don’t want to look like a cheap hooker.”

“Oh, I won’t do that,” Sue said, “I’ll make you look like an expensive hooker,”

The dance was much like the Christmas dance. I started with some words of welcome. When I stepped up on the stage, I was greeted with the usual whistles. I decided a little tease was in order, so I smiled broadly, hiked up the hem of my skirt an inch or so, and gave everyone a good look at my leg which included the top of my stocking and a garter strap. This drove the boys wild, and I noticed more than one girl elbow her date in the ribs.

As before, I started the dancing with the President of the fraternity council, and then what I called the ‘mandatory’ dances with officers of the fraternities.

Then I noticed Frank, my roommate. He came up to me and asked me for a dance. “As long as you behave yourself,” I said.

“You’re so beautiful, that may be difficult,” he said, “I keep on thinking what’s underneath that dress.”

“Try not to,” I said.

“You know, you can come directly back to our room, you don’t have to change first.”

“Sylvia might not like that,” I responded, “and there is chance that I might stay overnight at her apartment.” It was a lot easier before Frank knew that I was the Halloqueen and I knew that he was gay.

“Anyway, don’t you have a boyfriend?” I asked.

“I do. You.” he answered.

Not what I wanted to hear.

Like Christmas, I spent the night at Sylvia’s apartment.

Later that week, Sylvia, along with the other girls and I were sharing some takeout food at the apartment. “Who was that big hunk I saw you dancing with,” Sue asked.

“That might have been Frank, my roommate.” I answered.

“Does he know?” she asked.

“He figured that out at the Winter Carnival.” I answered.

“And he still wanted to dance with you?”

“Well, yes,” I said, “and I discovered something about him. He’s gay. So now I have a boyfriend in addition to a girlfriend.”

“You only need a girlfriend, me,” Sylvia said, “has he tried anything funny with you?” she asked.


“Keep it that way.” she said.

“He likes it when I dress,” I added.

“So do I,” Sylvia said. “Just don’t let him see you.”

Chapter 40 - Spring Break.

With spring break around the corner, a lot of my fellow students were planning to go to Florida. I was not one of them.

Mr. Phillips had called my agent and asked if I would ‘cut’ another record. Since making my last CD I had been composing and writing some new songs, and I readily agreed. He scheduled a session in the middle of the week. When I told this to Sylvia, she had some reservations. “I had hoped that you could spend some time with me at my house,” she said.

“I can,” I replied, “either at the start of the week or the end of the week. The start might be better, because I don’t know how many recording sessions there will have to be.” So, after my last class, Sylvia and I packed my car and headed off to her house. At Sylvia’s insistence I had packed a suitcase of girl clothes. I wasn’t sure why, because I had enough girl clothes at my house to cover the recording sessions. It was when we were at her house, I found out that Sylvia had planned a weekend of me being a girl, starting with going out to dinner with her parents.

“What about your parents?” I asked, “Won’t my dressing come as a surprise to them?”

“No,” she said, “I told them about you being the Halloqueen and sent them some pictures, so they’re expecting it. In fact, they may be looking forward to it.” I couldn’t imagine why.

After coming back from shopping on Saturday afternoon, Sylvia said it was time to start getting ready to go out to dinner with her parents. When we were ready, we met her Mother in the living room, “Your Dad will be with us shortly. He had some wardrobe issues.”

A few minutes we were joined by a nicely dressed middle aged woman. Sylvia jabbed her elbow in my side and chuckled.

Surprise, surprise, the woman was her Dad - her dad was a cross-dresser! He, or rather she, was wearig a maroon dress with a full skirt. The top part had a square neckline, and she wore a delicate gold necklace. Her makeup was subdued, and she was wearing a wig. “Sorry for the delay,” she said, “I couldn’t get my breast forms to look right until I realized that I had mixed two different sets. You girls might not understand, but maybe Jean would.”

“I do.”

“Mom says that she likes it when Dad dresses,” Sylvia said.

“It turns me on,” Sylvia’s Mom added.

“It must be genetic,” I muttered to myself.

“I heard that!” Sylvia said, “and maybe it’s true.”

“You have such a nice figure, how do you do it?” her Dad asked.

“An uncomfortable corset,” I replied.

“See,” her Mother said to her Dad, “how many times have I told you to get a corset?”

“Okay, maybe I will,” he replied.

So it was four ladies who went out to dinner that evening. Sylvia’s Dad was very interested in me being the Halloqueen and I had to relate all of the details.

Sylvia wanted to go with me to the recording studio, so at nine on Wednesday morning we met Mr. Phillips and Mr. Nicholas at the studio to go over the music. I was wearing a skirt and sweater. The first thing we did was for me to play and sing what I had written, as Mr. Nicholas timed each piece. After I had sung a song, they placed the score in one of two piles, ones we would include in the CD and ones we would not. “These we will put on the market to sell. As you will recall, we did that for your last CD, and we have actually sold about half of them,” Mr Phillips said, more for the benefit of Sylvia than for me.

Mr. Nicholas then pulled a pile of scores from his briefcase. “Why don’t you read through these?” he suggested. “We’ll record the ones you wrote today, and you can practice these others this evening and we will record them tomorrow.” He and Mr. Phillips had timed it perfectly. The recording crew began filtering in just as we finished going through the music. This time a drummer and string bass player arrived with the crew.

I laid down the piano track, first with the drums and bass, and then without. After this I laid down my vocal track and my vocal harmony track.

It was mid-afternoon when we finished. “Good session,” Mr. Phillips said. “Now go home and practice these others and we’ll meet at ten to record them.”

When the session ended, neither of us had eaten lunch, and Sylvia asserted that we were famished. We stopped at a fast food joint to satisfy our hunger pains.

No one was at my home when we arrived. There was a note on the table directing me to take a casserole out of the refrigerator at a certain time, and put it in the oven. The note continued to say that my parents would be home about six.

“I’ll have some time to go over these pieces,” I declared. Sylvia, who got turned on when I wore a dress or skirt had other ideas and led me to my bedroom. I had no idea when any of my sisters would arrive home, but neither of us really cared. Afterwards, I started rehearsing the music supplied by Mr. Nicholas, and finished about midnight, with a break for dinner.

The second recording session then went much as the first had done, except that Mr. Nicholas had me speed up or slow down some of the songs. As before, we completed the session by mid-afternoon.

After stopping for some fast food, we went back to my house. My parents were not due home from work until at least five-thirty, and as before, Sylvia had an idea as to how we should use the time before they came home.

The rest of the week Sylvia and I went shopping and otherwise amused ourselves.

Chapter 41 - Girlfriend.

At Sylvia’s insistence I remained dressed on our trip back to the campus, and after I dropped her off at her apartment, I went to my dorm room. Frank was there.

He looked me up and down, and then said, “Welcome back, girlfriend.”

“You’re very nice,” I responded, “but I’m not your girlfriend. As you well know, I’m not even a girl.”

“But you look like one,” he rejoinded, “and a very pretty one at that.” He moved over to me and surprised me with a kiss. I did not kiss him back. “Aw, sweety, you can do better than that,” he complained, and kissed me again. This time I responded. Still holding me he slid his hand down to my butt, and began rubbing.

“Enough!” I declared, “Please stop that at once.” He reluctantly released me and moved away a bit.

“I bought you a present as thanks for your help,” he said, and he pointed to a parcel on my bed.

“You pay me for my time as a tutor,” I said, “and that’s enough. You don’t have to give me presents.”

“Well, aren’t you even going to open it?” he asked.

“Well, okay,” I answered. Inside the parcel was an ivory colored nightgown.

“I got one just like it for me,” he said, with a smile.

“Thank you,” I said, “but I don’t know how I can wear it here.”

“That’s simple,” he said, “we lock the door, take off our clothes, and put the nightgowns on.”

“In your dreams,” I said, and folded the nightgown and put it back on my bed.

“Aren’t you even going to try it on?” he asked as he locked the door, “I will if you will.”

I just sighed, and started to undress. Frank did the same.

The nightgown was very pretty, at least on me. Frank’s was a plus size, and not as attractive on him. I started to take the nightgown off. “No, leave it on for at least a few minutes,” he said and he moved toward me and gave me a hug. He followed this with a kiss, and I could feel him fondling me.

While it felt good, I insisted he stop. We took off the nightgowns. I still had my panties on, and there was a involuntary bulge as a result of his fondling me. He saw it, and said, “So, you have to admit that I turn you on. That’s good, since you turn me on.”

I turned to him and said, “We’ve got to talk.”

“About what?” he responded.

“You hitting on me,” I said. “You’ve got to find a boyfriend or girlfriend of your own.”

“It’s not that easy,” he said. “It’s not like I can put up a sign or ad in the paper saying ‘Gay football player seeks lover. Cross-dressers welcome.’ I can’t let the guys know that I’m gay. You’re the only one on campus that knows.”

I thought for a moment and said, “Have you contacted any LGBT groups?”

“No,” he responded, “if I walked into a meeting, my secret would be out, so I can’t.”

“I’ve never looked for a gay lover,” I said, “so I can’t be of much help to you.”

Frank thought for a minute, and then said, “I’d go to a LGBT meeting if you’d go with me. They’d think that I was your protection, and not suspect that I’m gay.”

“But everyone would think that I was, so your answer is no.” I responded. “I guess that you’ll have to go trolling near gay bars,” I said.

“Which ones are those?” he asked.

“Go looking. I certainly don’t know.” I concluded, “In the mean time, no touching or kissing.”

I finally gave in and went with Frank to a LGBT meeting. A lot of those present cast hungry looks at me, which I ignored. Frank was successful and it was not too long thereafter that he found a lover. I accommodated them by leaving them alone in the dorm room for their trysts. I even gave Frank’s lover the nightgown which Frank had bought for me.

Chapter 42 - Spring Fling.

The final event which the sororities and frats hosted was the ‘Spring Fling’ which followed the frat and sororities’ initiations. I was in a quandry. They wanted me to be there as Halloqueen and to dance with all of the new members of the frats, but my fraternity wanted me present as a new member. I hoped that I could attend as a new frat member, and not as Halloqueen, but that was not what the powers that be decided. I suspected that Ann had a part in this.

They decided that I would be the Halloqueen, and as such be introduced as a new member of my frat, fully dressed, as they directed, in the same clothes as I wore at the Valentine day dance. I was directed to show a lot of leg. I finally went along with what they had planned. However, someone was needed to dance with all of the new members of the sororities, and a likely suspect was convinced to do the same. Of course, I was to dance the first dance with him. He didn’t like the idea, and neither did I, but we were pressured into doing it.

There was one surprise. During the time the DJ was on break, Jill, the President of SRS, presented me with a photo album of all of my appearances as Halloqueen. When she presented it, she made a little speech, acknowledging how I was one of the best Halloqueens for many years, and how I really showed school spirit, and a lot of leg. She even plugged my new CD.

After Spring Fling, the student body worked on final projects and papers, and prepared for the final exams. Frank was pleased with his performance that semester to date. Going into finals he had a good average in his courses, and he felt confident that he would do well on the final exams.

I also felt confident that I would get A’s in most of my courses, which I did.

Summer was approaching and I hadn’t lined up a summer job. Being a self-employed songwriter just didn’t cut it. The earnings from my recordings were modest. I needed a real job.

Sylvia and I were sitting at the kitchen table in her apartment. At her insistence I was wearing a blue pleated skirt, pantyhose, heels and a black chiffon blouse. When I related my problem to Sylvia, she suggested that I list my assets and see if they suggested a job. Sylvia picked up a pencil. “Give me an asset,” she said.

“Fluent in French,” I responded.

Sylvia chuckled and said, “Great looking legs.” She twirled the pencil around, “good in bed,” she added.

I looked at her list. “These sound like the qualifications for a high priced courtesan,” I said.

“There’s a thought,” she said.

“Not a very good one,” I muttered.

“How about sings and plays piano?” Sylvia said as she wrote them down.

“Not much use for flipping burgers in a fast food joint,” I responded.

“Don’t be so negative,” she said.

“I’m not negative,” I rebutted, “I’m a realist.”

“And a cute realist,” she said, as she slid her hand up my skirt.

“Oh, we can’t forget ‘likes dresses with slits up the side’,” she added.

“I don’t,” I countered.

“But I do, when you wear them,” she said, with a wicked smile on her face.

“Hummpf,” was my response.

“Let me improve your mood,” she said as she took hold of both of my hands and lifted me up off of my chair, and led me to the bedroom.

About an hour later we were again sitting at the kitchen table. My mood indeed was better. “Hey,” I said, “I just got a check from the record company. Let’s go somewhere fancy tonight for dinner.”

“That works for me,” she responded. “Now, what to wear?” she posited.

“Coat and tie,” I answered.

“Spoil sport,” she said, “I was thinking a nice dress,”

“For you? That would look nice,” I responded.

“No, for you, silly,” she rejoined.

“If you insist,” I said.

“I do.”

So I changed into a deep violet dress with an A-line skirt and fitted bodice. Sylvia was likewise attired, and we headed downtown to the Carleton House, the most fancy restaurant in town. We hadn’t made reservations, so we had to wait in the lounge area, which was okay, because a woman was playing cocktail piano. “You could do that and sing,” Sylvia speculated.

Chapter 43 - A Job Offer.

It was a half hour later that our table was ready. We could hear the piano in the dining area. As we were being escorted to our table, I mentioned to the maitre d’ that I really enjoyed the piano.

“Enjoy it while you can,” he said, “because she and her husband are going away for the whole summer.”

“But you have a replacement?” I asked.

“Not yet,” he said, as he looked me up and down, “You play?”

“Yes,” I answered.

“She’s a recorded professional,” Sylvia interjected.

“You union?” he asked.

“No,” I responded, “Is that important?”

“Gotta be union to work here,” he said.

“How hard is it to join?” I asked.

“If you’ve got a gig lined up and pay your dues, you’re in.” he said, “If you’re interested, come by on Monday afternoon and talk to the manager,” he added.

So that Monday I wore a cocktail dress which I borrowed from Ann, and Sylvia and I went to the restaurant. The manager checked out my appearance. “You look okay, now let’s see if you can play as well as you look,” and with that he led me to the piano. I sat down and began to play. “Okay, you can play,” he said. “I’ll give you the names of some songs, and let me hear you play them.”

Two of the songs he named were on my CD’s, and I had those down cold. I noticed that there was a microphone near the piano. The manager saw me looking, and asked, “You sing?”

“Yes,” I answered. “Two of those songs are on a CD I released a while ago.”

“You’ve got music on the market?” he asked with a little incredulity. I nodded my head.

“Could you loan me a copy?” he asked.

“No problem,” I responded.

“Okay,” he continued, “we have music three hours Wednesday through Sunday evenings. We pay union scale. Tell the union that I hired you. Can you start three weeks from Wednesday? That’s when our current pianist is leaving for vacation. The gig runs through Labor Day when our regular pianist returns.”

“So I’m hired?”

“You bet,” he responded. “If you’d like, I’ll buy you and your boyfriend dinner on Wednesday and you can talk to Adele about what you can expect.” Adele was the regular pianist.

Sylvia was not happy that she was not included in the free dinner, but she assured me that it was okay provided that I took her shopping with me. “All of the girls agree that you need some more cocktail dresses for your job. So, who’s going to be your boyfriend on Wednesday?”

“I think I’ll ask Frank,” I responded.

That evening I mentioned my new job to Frank. “I’ll be playing cocktail piano five evenings a week at the Carleton House restaurant. They want me to come over on Wednesday with my boyfriend to give me a chance to talk with the regular pianist before she leaves for the summer.”


“I want you to pretend to be my boyfriend. You’re big enough to be my protection. You get a free steak dinner out of it,” I said, “That is, if your boyfriend doesn’t pitch a hissy.”

“Just a meal?” he asked, with a gleam in his eye.

“Just a meal,” I responded , forcefully.

The next day the girls and I went shopping for cocktail dresses for me. It became readily apparent that my only purposes of being there was to make sure the dresses fit and to pay for them. The girls were having a great time, the more risque the dress, the better they liked it. Naturally, all of the dresses had revealing slits.

I objected. “You realize that I’ll be sitting at a piano, so the dress will fall open, revealing a lot of leg.”

“And that is a problem?” Ann said, “I don’t think so.”

I ended up with two new cocktail dresses, one in royal blue and another in a deep maroon, The hems of both came to a few inches above my knees, and the bodices were fitted. Naturally, buying a dress wasn’t all. We looked at shoes. I reminded them that I had to use the pedals on the piano, but I still ended up with four inch heels. Then came stockings. The girls insisted that I have stockings, not pantyhose. Since the dresses would be revealing, they insisted that I purchase new lingerie, in black.

So, suitably attired, I picked Frank up at the dorm. He was dutifully impressed. “I wish that you were my boyfriend,” he said, “You look so beautiful and sexy.” When I drove to the restaurant, the skirt of my dress fell open at the slit, exposing my stocking tops. Poor Frank couldn’t keep his eyes from my legs.

Adele, the regular pianist was maybe fifty-five and a plus size. “You’re going to drive them wild,” she said when she first saw me. Frank and I had our dinner in the lounge, next to the piano. Adele and I traded off sets. “You’ll do just fine, Honey,” she said. I asked about boys hitting on me. “I never had the problem. At my age, I consider being hit upon to be a compliment. Some men will want to buy you drinks. The bartenders will give you a soft drink when this happens. Just tell them what you like.” She paused. “Of course the guys buying you drinks will get charged as if it were a mixed drink. Keep a tip glass on the piano. You should collect a few bucks extra every night. If anyone gives you a problem, give a signal to the bartender and someone will be sent to rescue you.”

Frank and I left when Adele was finished for the evening, and I drove Frank back to the dorm. His boyfriend was waiting for us. I leanded over and whispered, “You want me to spend the night at the apartment?”

“That would be a nice idea,” he said. When I got to the apartment. Sylvia also thought it was a nice idea.

So I had a summer job lined up. It was only 15 hours a week, but at union scale, which would earn me more over the summer than if I was flipping burgers. However, I couldn’t help wondering why I seemed to need to wear a dress more and more.

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