Billy’s Desires

Billy’s Desires
A Short Story
By Maryanne Peters

I had convinced myself that being born male was the best thing in the world. I mean, men run it – the world I mean. Men are in charge. Women have babies. Women are meant to look pretty and look at their men adoringly, but they offer nothing when it comes to leadership or innovation – that was my position, back then. Somehow it seemed that the more I said it out loud, the truer it became.

All it did was piss my Mom off. I understand why. It was for me. It was to assure myself that I really wanted to be male. Even the fact that she was pissed made me feel more like a man.

So, then she decided that I needed to be taught a lesson. She had decided that I had to be a girl for a whole 48 hours. It just so happened that it was prom weekend, but that didn’t matter to me. I was not going. Prom was for girls so they can get dressed up, and I didn’t mix with girls, because that was not who I was.

I had to concede that I had been a prick and I agreed to take her punishment, thinking that I would have to just wear a pinny and help her around the house.

“If this is what you think being a woman is all about, then it just confirms that you need the full experience,” she said. “You’re not going to like this, but you are going to the prom tomorrow night as a girl. You remember my hairdresser Lisa? Well, her son needs a date and that is going to be you. You need to experience what it is like to look pretty’ like you said girls are meant to.”

How ironic is that? My own words coming back to hit me over the head. Despite whatever was going on inside, I dreaded the idea of having to step out as female.

It so happened that Mom had a prom dress. Mom was a dressmaker and this outfit had been abandoned by the girl who was to wear it to the prom, who tossed it at my mother after a fight with her boyfriend. My mother brought it home and started talking about how a dress like this had to be worn and admired. I didn’t realize it but she looked at the sizing and she looked at me, as I was ranting at her about some stupid girls on TV. I had no idea what was going on in her head. It was not until she had decided on my punishment that the dress reappeared.

“This dress will fit you perfectly, if we shape your body a little,” she said. “A prom dress needs a prom and now we have one.”

“I am not going to my school prom in drag!” I protested.

“Not your school, no,” she said. “Lisa’s son Roderick goes to the military academy on the edge of town. If you don’t want to go in drag, then you will have to go as a girl. That means looking like a girl and acting like a girl. That way Rod will be the only one to know your secret.”

My brother had gone to that military academy, paid for by the Army after my father was killed in Afghanistan. I could have gone too, but it was not for me. My brother was now in the service, and I was alone with Mom and not doing much. If she wanted to throw me out of the nest, there was no safety net. I would have to agree to what she wanted. It was to be an ordeal I would have to endure, as my father would have said it.

The weekend was still some way off, but as those weeks passed I found myself increasingly agitated by the thought of this prom thing, if agitated is the right word. I started to have a series of dreams. In each of them I had breasts and a vagina and long hair, and I was dressed in lacy underwear or a minidress or a ballgown or a bikini. I was either just being a girl or, on a couple of occasions I was in the company of a handsome young man. My only hope was that once this was done and over, these weird thoughts would end.

Then the evening before the Saturday prom my mother had me go around to Lisa’s salon to start “the preparation”. I soon discovered that this was going to be an all-over waxing, and had to be done the day before to ensure that any inflammation had time to decide. Lisa had opened the salon late just for me, and so like the horror movie, there was nobody to hear my screams.

“Your squeals are not high enough,” Mom said, less than sympathetically. “You need to raise your voice a few octaves to sound like a girl, rather than just spend the whole night not talking.” I guess the pitch did go up, but with not much effort on my part.

Mom spent the whole time telling me that I would not regret going to this effort. Lisa was telling me what a great guy her son Rod was such a great guy, and that he would look after me and ensure that I wasn’t embarrassed.

“Rod knows who you are, and he wants your secret maintained as well,” Lisa said. “So, it is up to you. I suggest that you spend some time watching girl movies and try to observe and imitate. A masculine step or a clumsy gesture might give you away.”

Next came the work on my hair. It was not going to be a wig but extensions in my hair that was already longer than most boys in my class.

“Is this necessary a full 24 hours in advance?” I had to ask.

“You need to get used to having hair like this,” said Lisa. “You need to care for it tonight and all day tomorrow, and then come back before the prom to have it styled. Makeup too – I will do it for you tomorrow, but I will show you how to do the basics tonight – mascara and lipstick. You may need to freshen up at the prom, so you need to know how.”

When I headed home I had long hair and I was wearing makeup, and when I got home Mom produced the undergarment that I would be wearing. It was a very tight one piece cinched my waist and had gel pads and a push up arrangement to allow for a visible cleavage. In the crotch was a place for my penis to lie in a channel and point down so I could pee like a girl. Over this I could wear lacy panties and a bra as well.

“Let me get the dress and we can try it on,” Mom said. “Maybe I need to take it in a little. Wait here.”

I stood in front of the full length mirror in her bedroom looking down at my legs, as smooth as a billiard ball and the redness already having disappeared. Then I looked up and into the mirror.

I saw a girl standing there. She could have been naked. The shaping garment was flesh colored and almost invisible in dim light. A pretty naked girl stood there with her breasts and her hairless feminine crotch, looking afraid and yet gorgeous. He bra strap-length straight hair hung down and her makeup showed her big anxious eyes. She was beautiful.

Beautiful women make people smile, and she smiled back. She flicked back a lock of hair and turned a little, angling her leg to show off her shape and how good she might look in heels.

The crazy thing was that whatever masculinity I thought I had seemed to have evaporated so quickly that I wondered if it was ever there in the first place.

Mom appeared with the dress. I think that she caught me admiring myself but she said nothing. She had me put it on, and she had found a pair of shoes for me to wear – black heels that would look great with the red dress – even I knew that.

The dress was a perfect fit, but not the shoes.

“That settles it,” said Mom. “We will need to go to the mall tomorrow and buy a new pair.”

“Ok,” I said. I was looking at the girl in the mirror – she was looking forward to a shopping trip.

“You will need to remove that makeup and tie back your hair, and put on some night cream,” said Mom. It all sounded so feminine and so inviting somehow. I did exactly what was instructed. I used one cream and then the other, and marveled at my smooth skin.

I fell asleep easily, and those dreams returned. But this time I was on a bed lying naked with my ample breasts exposed and my crotch carrying just a small tuft of pubic hair above my wet vagina. Inside that vagina was a cock, and attached to that was a man, smiling down at me and shaking my breasts and my curls which each of his solid, manly strokes. Rather than wake up with a start, I just laid my head on the pillow and hoped that it would last forever.

In the morning Mom suggested that we head to the mall early.

“Rather than watch movies you can watch girls in their natural habit and learn their behaviors,” said Mom, imitating a wildlife documentary. “Now, we just need to put together something to wear that would not embarrass a girl your age. I may need to go into my stock to find something.”

She had plenty. She picked out a few and asked me to pick something.

“Good choice,” she said. “You are really getting into this, Billy. In fact, while we are out, I will need to call you something else. What about Willow?”

That was who I became that day. Willow and her mother went to the Mall and enjoyed moth daughter time. It was wonderful. We found the perfect shoes and sat at the juice bar just watching all the other women who were just loving life being women. That was the way it seemed. Men seemed to be gruff and determined and they were often alone. Women like groups, and talk, and pretty things. It was like finding where I belonged.

We had a late lunch and then found that it was time to go to Lisa’s salon for the final makeover. This time the salon was full, and it seemed that everybody knew that the pretty girl at the end of the row was Willow and she was going on her first prom with Rod, Lisa’s daughter.

Their excitement made the excitement build in me, and when I saw the final version of me ready for my social debut and was ecstatic. I looked so beautiful I could not believe it. All of the feminine feelings that I had bashed down my whole life seemed to just spew out of me. I now understood – this is who I dreamed of being. All the rubbish I spouted had been just a way of denying who I was.

I could not wait to get home and put on my dress. As I rushed out the door the ladies in the salon, staff and customers, applauded and wished me well.

I looked around my bedroom and I knew things had to change. I ripped some posters off the wall right then. I needed the dark colors to go and to get some light in there, and plenty of mirrors to admire the new me. I might even paint in pink. But that was all to come later. I needed to be ready for Rod.

I had a moment of concern as I waited for the doorbell. What would he be like? Surely he would not be nasty and cruel like Billy? But more importantly, would he like me? Then I realized that these were the thoughts that any girl would have. That was what I was – a girl like any other girl.

I went to the bathroom, and I sat down to pee, pulling down my panties and peeing with the assistance of what I wore underneath. I decided that I would put a panty liner in place, just in case.

Then the doorbell rang. I primped a little as Mom called for me to come down, and then I paused. This was going to be my entrance. It could not be rushed. I slipped on my brand-new heels and walked down the stairs.

There was Rod and my mother waiting. Mom was beaming with pride, and Rod was beaming too. In fact, he looked awestruck, which made me feel awesome.

“My mom told me that you were a stunner, but I was not prepared for this,” said Rod. His voice sounded like warm molasses and as I drew near I could see that he was taller than me even in my heels, and that under his suit he was muscled. He was a little older than me perhaps, but he was a man, in every sense of that word. He had a corsage for me and he slipped in on my wrist.

“Hello Willow,” he said. “Will you accompany me to the prom tonight as my date?”

It was all arranged so this was unnecessary, but it was a wonderful question to hear. I sounded just like “will you marry me”, so of course, there was only one answer.

“Yes.” I breathed it as if it was my last breath.

He had a car and driver waiting and he held the door. It was heavenly. As we rode through to the academy he briefed me on who would be there – his friend and their girlfriends. I just looked at him and nodded, thinking nothing except how wonderful this all was. It was a Cinderella story. I had been living in ashes and now I was a princess, in the backseat of a car with a prince.

“Nobody knows your secret,” he whispered as we arrived. “It is just between us.”

“Why me?” I asked. “You could have any girl. I can see that. But I am not yet a girl. I am incomplete.”

My words seemed to confirm to myself that I was not going back. I had taken a step into the ocean and I was not getting out until I got to the other side, there made complete.”

“I have always dreamed of a girl just like you,” he said. “My mother has known about it, and she must have talked to your mother. I want to help you to become the woman that you need to be.”

There, in the car, he gave me the first kiss we ever shared. There would be plenty more, that night and every day since.

And after that prom we shared an even deeper connection, if you know what I mean.

Oh my God! His name is Rod, and I know why.

The End
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© Maryanne Peters 2024

Author’s Note: I must have written dozens of little vignettes on this theme – rebellious teenager is forced or persuaded to dress as a girl to date a young man to the prom