tagTransgender & CrossdressersHigh Fashion Queen

High Fashion Queen


Authors Note:

I want to thank my editor Pete who goes above and beyond for me. Also, I'd like to thank everyone who reads my work and offers critiques, support, and encouragement. It means the world to me.


Of an old love's fancy life that left you stranded in a dream,

Ain't you glad you're a high fashion queen.

The Flying Burrito Brothers


I felt like such a loser. It was Friday night and instead of going out and hitting the clubs to dance, drink, and have fun, I was in my dorm room with my best friend. We had known each other since the 6th grade and today was his birthday. No one should be left alone on their birthday right?

To be honest, I didn't really feel like going out anyway. My boyfriend, who I had been seeing for the last three months, had been cheating on me with his ex-girlfriend. I caught them in bed together two days ago, and nothing had been able to pull me out of my doldrums since. I liked to think that staying in on a Friday night and keeping my friend company on his birthday, was good Karma anyway.

My friend Jesse and I decided that he would supply the pot and I'd order a pizza and we'd spend the evening together, just like we did so many times in high school.

Jesse is what I affectionately refer to as a dweeb. He was a diminutive Asian guy who was bullied almost constantly in high school, because of his small stature. He is very shy and quiet and I can't ever remember him even speaking to anyone besides me.

We met in middle school when some thugs from the football team were picking on him and I came to his rescue. Not that I am much bigger than he is, but they weren't going to hit a girl and they backed down when I started yelling at them. Since that day, we had been best friends and I found him to be one of the sweetest people I know. One time, we even tried to kiss, but both of us agreed that it was awkward and neither of us felt a spark, so we mutually decided that we should just remain friends.

It was six-thirty and both of us were incredibly high and full of pizza.

"I'm sorry again Sara that your boyfriend cheated on you," he said, in voice barely above a whisper.

"It's okay, I always knew he was too good for me and it was only a matter of time before he'd find someone better." I said softly.

"That's a horrible thing to say, you were too good for him."

"I'm taking solace in the fact that he was hung like this," as I held up my pinkie finger.

We both burst into laughter, more from the strong, hydroponic pot than my little joke.

"His ex-girlfriend deserves him," I said, as I took another long drag from the joint.

I'm not sure if I could be classified as pretty. I've always thought of myself more as average looking. Maybe 'tomboy pretty' if that's even a way to describe someone. But, when I want to, I clean up okay and at the very least look presentable. I've always had a high sex drive and there was never a shortage of guys in high school or college that were willing to hook up with me. Unfortunately, I could never find 'Mr. Right' which lead to a lot of one night stands and failed relationship attempts.

We both looked up at my dorm room ceiling, enjoying the comfortable silence until I spoke again.

"So when are you going to introduce me to your girlfriend?" I said teasingly.

This was a sore subject for Jesse, but I knew he'd be okay with my gentle chiding. Besides our failed attempt, he hadn't even kissed a girl, much less had sex. It had to be horrible being twenty-one and still a virgin.

"You may meet the wrong guys Sara, but I can't even meet anyone," he said sadly.

I didn't want him to be depressed liked me. That was the whole reason for the pot, so we'd escape our pathetic lives for a while. Just then, a crazy thought entered my mind.

"Jesse, I know that you've never, umm... You know... Had sex."

"Thank you for reminding me Sara, what's your point?" he said smiling.

"We could always, you know... Umm... Do it," I said shyly, "that way, you'd at least know what it's like. It could be like, you know, birthday sex, my present to you."

He thought for a moment, and there was a split second when I actually thought he was considering my offer and might actually take me up on it. Then, the conversation took a turn that I wasn't expecting.

"I think I'm gay Sara," he said quietly

My mouth dropped open as I reflected on his statement.

Jesse is gay? Jesse is gay. In the back of my mind, I might have suspected it, or at the very least wondered if it was a possibility.

"Have you ever... Umm... Done anything with a guy?" I asked hesitantly.

"I haven't, but it's all I think about."

This was getting juicy. I tried to will my mind to focus amidst the haze of the pot. When Jesse and I spoke about sex, it was always about me and who I was hooking up with. I was pretty sure that the marijuana was loosening him up, so he felt more comfortable and able to speak freely with me about his fantasies and desires.

"What do you think about?"

He took a long drag from the joint and once he exhaled, he spoke again.

"What it would be like to have one in my mouth, or you know, have sex,"

I could tell just by looking at him that he was thinking about it that very second.

"So in your fantasies, are you pitching or catching?" I said, smiling at him.

"Definitely catching."

There was another comfortable silence as we passed the joint back and forth.

"You said you wanted to help me and give me a birthday present. Would you still be willing to do something for me?"

"Well, if you fantasize about catching, I don't think I'm physically equipped to be of much help to you," I said, teasing him again.

He gave me a very serious look, and I could tell that whatever was on his mind was important to him and I immediately felt bad about my earlier quip.

"Jesse, of course I'll help you, with whatever you want."

"Would you help me dress as a woman?" he said, in a tone barely above a whisper.

I quickly tried to get the shocked expression off my face. Jesse being gay was pretty easy to accept. Jesse wanting my help to dress in drag, that came out of left field. In the end, it didn't matter, he was still my best friend.

"Of course I will," I said, trying to focus and mentally formulate something that resembled a plan.

"What should I do first then?" he asked.

I thought for a moment while studying him from head to toe.

"You need to shave all of the hair off your body from the neck down and by the time you get back from the shower, I will have figured out what to do next."

He instantly jumped up and tore out of my dorm room. I could tell he was excited about this and I don't think I had ever seen him move so fast. Well, maybe except a time or two, when he was being chased by a couple of bullies in high school.

About a half hour later I heard a knock on the door. I opened it and Jesse walked back into my room, freshly showered and shaved wearing shorts and a tank top. I had everything set up and ready to go for his transformation.

"Sit here," I said, as I pointed at the chair I had set up in the middle of the room.

Once he sat down, I immediately went to work. I could tell he had washed his face and shaved his very sparse facial hair. I put on a light coat of moisturizer while admiring his beautiful skin, it was something I had never really noticed before. After the moisturizer, it was time for the concealer and luckily, I had foundation that I thought was certain to match his skin tone perfectly.

I used my brush to apply a very light coat of setting powder. If we were going to do this, we might as well do it right I thought. The next step was highlighter. I brushed it around the corners of his eyes, beneath his eyelids, and finishing on his high cheekbones, which gave his face a nice depth of color. I continued to work on his eyes using a powder that was a couple of shades darker than his natural skin tone. I dug around in my make up case for a few seconds until I found the blush. Meticulously, I applied a small amount on his cheeks to help accentuate his high cheekbones.

I sat back for a moment admiring my work. Time to focus on his eyes.

I pulled out the eye shadow primer and eye shadow and applied it on his eyelids. I chose a darker color which helped accentuate his big brown eyes. Finally, I applied eyeliner which gave the illusion of a fuller lash line. With his eyes still closed, I very carefully brushed on the mascara.

I again stepped back. His look was really coming together I thought and then.... a strange feeling came over me. This was actually turning me on. I could feel the dampness between my legs and I knew I was starting to soak through to my thong. I quickly put this very unexpected reaction out of my mind so I could concentrate on my friend.

Okay, last step, his lips. I applied a light coat of lip primer, and then I very carefully used lip liner to trace around his lips, using a color that was nearly identical to natural color his lips. I thought for a moment, should I go bold or demure on the lip gloss? Go bold or go home I thought. I picked a bright red shade, and very carefully painted it on, giving his lips a full, slutty, pouty look.

I could tell he was anxious to see the end result, but I made him wait. I wanted him to get the full effect of my work. I reached over and grabbed the wig I had borrowed from my friend across the hall. She was a theatre major, and luckily she had about a half dozen wigs from her various plays.

Jesse had short, jet black hair and the wig I borrowed matched his natural hair color perfectly. I put the wig on him and styled the long hair until it fell naturally down over his shoulders.

"Can I see what I look like so far?" he said pleadingly.

"I think it would be better if we waited until you were dressed, so you'd get the full effect," I said.

"Please Sara, I don't think I can wait."

I relented, it was his birthday after all.

"Close your eyes," I said.

I watched as he closed them and I gently took hold of his shoulders and turned him so we both faced the mirror.

"Okay, open them."

I watched as his eyes opened and it was as if his jaw had hit the floor while I stood beside him in my old torn t-shirt and ratty sweatpants. There was only one beautiful woman looking back at us in the mirror, and it wasn't me.

It wouldn't be exaggerating to say that in this newly transformed state, Jesse looked like a model. Obviously not as tall as a model, because he was only 5'4". However, because of his high cheekbones, soft feminine features, the jet black flowing wig, combined with my makeup job, I would have sworn Jesse was born a woman had I not known the truth.

It took him a full two minutes to speak. He just stood there staring into the mirror and I watched as his eyes went up and down his reflection as he studied every detail of the transformation.

"Sara, I... I... Thank you," he said simply.

I could tell that he was ecstatic with what I'd done so far. Now, the last step.

"What do you want to wear?" I asked.

"Honestly, I have no idea," he said hesitantly. "Why don't you just pick something."

Jesse and I were nearly the same size so I figured he could just wear something of mine.

I paused for a moment trying to come up with something simple for him to wear. I rummaged through my closet for a couple of minutes and finally found a short, faded blue jean skirt and tiny black cowl neck halter top. I desperately needed to do laundry so I didn't have a large selection of lingerie to choose from, but after what felt like an exhaustive search, I finally found a clean matching white lace thong and bra set.

I turned around and faced him and showed him the clothes I picked out. His eyes immediately lit up and I could tell he was happy with my choices.

He stripped off the tank top and dropped his shorts to the floor. In an instant, he was standing naked in front of me, his small erection standing up proudly. I now felt bad concerning the earlier remark I made about how small my ex was because Jesse appeared to be about the same size.

It didn't seem to bother him though as he reached for the lace bra in my hand and began to put it on. He turned away from me so I could help fasten the little hooks in the back. He turned again to face me and I realized how ridiculous the bra looked over his flat chest. I thought for a moment and then grabbed some of my gym socks and rolled them up into small balls and stuffed them into the cups of the bra giving him the illusion of breasts.

He started to slide the thong up his thighs and then paused for a moment and a perplexed look appeared on his face and I could tell something wasn't right.

"What's wrong?" I asked. "If you don't like that thong I can try to find another one, but I don't have a big selection right now because I need to do laundry."

"No, it's not that Sara, it's..."

I waited patiently until he felt comfortable enough to tell me.

"For this to look right, I have to be able to tuck my penis back, and I can't do that when I'm hard," he said, in an embarrassed tone.

I thought for a moment.

"Would you let me help you with that?" I asked cautiously.

He gave me a bewildered look and I was pretty sure he no idea what I was planning to do until I got down on my knees in front of him. For some reason helping him with this transformation had made me incredibly wet and worked up. I didn't really even think about what I did next. It was just a spontaneous, almost involuntary act that in the moment, just felt right.

His eyes opened wide as I leaned forward. He had a long string of pre-cum dangling off his cock. I heard him moan as I took him into my mouth. While I gently began to move him in and out of my mouth, he placed his hands on my shoulders in an attempt to steady himself.

I swirled my tongue over the head of his cock and I heard him gasp. I very easily took him all the way into my mouth and closed my lips tight around him and then very slowly I started working him in and out. He was so worked up from the whole transformation I found that I really had to fellate him slowly because any time I increased the pace he started to tense up and his breathing changed and I knew he got close to orgasming. Even fellating him at this incredibly slow pace, I still had to stop several times because I could feel how close he was getting to orgasm. Since he wasn't going to have sex with me, I wanted him at the very least, to enjoy his first blow job.

After stopping for the fourth time I let his cock pop out of my mouth. It was shiny and wet and my saliva was dripping off of it. I looked up into Jesse's big beautiful brown eyes, my pot addled brain instantly began processing the many strange contradictions I was feeling. I had given lots of blow jobs, but never to someone who looked like a woman, yet, had a cock and was my best friend nonetheless. It was just so many different contrarieties that my mind, in this inebriated state, couldn't deal with them all.

I put all of those strange thoughts out of my head and took him back in and started to rapidly move him in and out. Immediately, I felt his hips start to buck as he thrusted himself into my mouth over and over. Seconds later, Jesse started moaning and grunting and I felt hot splashes of cum squirt over my tongue. Once he started to settle back down and the rapid pitching of his hips subsided, I swallowed his thick semen.

I wiped a drop of his seed from the corner of my mouth and carefully licked over his penis, cleaning the little drops of his cum that I had missed.

I looked up into his eyes and we smiled at each other.

"Thank you Sara," he said, "for everything."

"You're welcome Jesse," I said, smiling brightly at him. "Now let's finish getting you dressed."

I watched as he opened his legs and carefully tucked his scrotum back. I was mesmerized how, in just a few seconds, his cock and balls appeared to have magically vanished. I had never seen anything like that before.

He then pulled up the thong and slid the little skirt up his thighs. I handed him the black, halter top blouse and he put it on.

"You need some shoes," I said, noticing that he was in his bare feet.

"I've always wanted to wear heels," he said.

I thought for a moment.

"Jesse, heels won't go well with that outfit, they are much too formal and that outfit is way too casual."

He gave me a disappointed look.

"Can I at least try?"

"Yes, of course you can," I said.

I looked into my closet and pulled out a pair of four inch, rhinestone, t-strap sandals. His feet were a bit wider than mine and I knew he'd never fit into any of my pumps.

He put the heels on and I helped him lace them up. Once we had them on, he stood up, took a few steps and immediately began to wobble and nearly fall. I reached out to steady him and then helped him get back to the chair where he could sit down.

I tried not to laugh, because I didn't want to upset him.

"I think you need a bit more practice before you'll be able to wear those." I said, trying as best I could not to giggle.

"You may have a point," he said smiling.

"Let me find you something easier to walk in, that will go well with that outfit."

I rummaged around my closet again and pulled out my new pair of Cocobelle gilded leather sandals. They were flat, so he'd have no trouble walking in them.

I helped him put them on and secure the little straps around his ankles.

"That's perfect, now let's check how you look one more time," I said.

He stood up and moved beside me as we looked at our reflection in the mirror. He truly looked stunning and I was a bit envious. He had naturally dark tanned thighs that went perfectly with the faded jean skirt. I looked down and admired his round, heart shaped ass that looked impeccable in the short little skirt. Guys always went crazy for an ass like that I thought. The dark, long, flowing wig matched his skin tone and makeup perfectly and the stuffed bra gave him the illusion of small 34b breasts. They were just big enough for him to get a little attention, but small enough to go perfectly with his petite frame. I was utterly amazed as it was virtually impossible to tell he hadn't been born a woman.

We both stood awestruck in front of the mirror for at least five minutes. Dressed as a man, Jesse was average looking, at best. However, dressed as a woman, he was truly stunning.

While admiring how good he looked, my thoughts traveled back to high school, to all of those beautiful, stuck up cheerleader bitches that thought they were too good to say hello to anyone who wasn't in their 'social class'. Maybe I had some unresolved high school issues that I needed to deal with.

The pot was finally starting to wear off and I grabbed my lighter and Jesse's dimebag to spark up another joint.

"Sara... Wait," he said, his voice startling me.

"What's wrong?"

"If you light that up, you won't be able to drive."

"Where do you want to go?" I asked incredulously.

He smiled brightly, "I'm twenty-one and legal, I want a drink of course."

My jaw dropped open and I started to get pissed.

"I did all this work transforming you Jesse and after only a half hour, you want to go back to how you looked before, just so you can get a drink? Are you fucking kidding me?" I snapped angrily.

"No Sara, I'm not changing a thing, I'm going out just like this."

I thought for a moment, processing his words and their implications.

"I'm not sure if that's such a good idea," I said softly.

He looked seriously into my eyes.

"I've been a social pariah for twenty-one years Sara, but in one night, you turned me into this," he said, as we both looked into the mirror at his reflection and saw a beautiful little Asian hottie looking back at us.

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