tagTranssexuals & CrossdressersA Butterfly Emerges

A Butterfly Emerges


It wasn’t my fault that my parents were small people and passed their genes on to me. However, it was a curse that I was forced to live with during my formative years. Sports like basketball, football and baseball were out of the question and I felt alienated from other children my age.

My parents did pass on to me a desire to succeed and I sought recognition through non-sport pursuits such as piano, art and drama. I became quite accomplished in these areas and was a favorite of my teachers.

High school was one living hell for me as I was forced to constantly deal with taunts from bullies and the jocks. I immersed myself in my studies, particularly science, and when graduation came, I had achieved valedictorian status.

College brought further harassment from the fraternity boys and drove me deeper into my computer science studies. I graduated from State Polytech a complete nerd with exceptional computer skills. In short, I was a social misfit but in great demand in the rapid growth computer industry.

With no social life to speak of, I was willing to devote endless hours working on new technological innovations. When my patent for a new semiconductor was approved, I became an instant multi-millionaire. I had all the money that I would ever need, but no friends or social life.

There was one young woman who worked at Allied Tech who I had an interest. She was petite and quiet, like me. I finally worked up enough nerve to ask her out. She accepted and I was looking forward to my very first date.

We had a very nice dinner at a French restaurant. I impressed her by ordering en Francais. We took in a very nice production of La Boheme and things were looking up. I decided to be bold and we went to one of the new “with it” bars uptown. This proved to be a big mistake.

There was a huge line in front with menacing bouncers deciding who the beautiful people were and granting admission by their whim. We waited for what seemed an eternity before we made the head of the line. We were abruptly stopped by the bouncer.

Where do you think you’re going pipsqueak?

We’re going inside.

Not while I’m working the door. I don’t want any little pussy faggot trashing up the image of this place. Now, your date can come in. She’s a fine looking babe. You’ll just have to blow out of here or better yet, just blow me.

I started to say something that sounded vaguely like a legal threat when the bouncer picked me up and stuck me in a trash bin beside the door. I struggled to get out as I saw him open the door and my date disappear into the club.

I was totally humiliated and vowed never to allow myself to be hurt or made fun of again. I retreated to my luxury penthouse and immersed myself in drugs, alcohol and self-pity. After an emotionally painful two weeks, I stared into my mirror and still faced a 5 foot six inch, 120 pound, effeminate man.

Life as a man had been unfulfilling and a living nightmare. I wondered what it would be like to live as a woman. No one would make fun of my slight build and high voice anymore. I began to hatch a plan.

I flew to San Francisco on the first leg of my adventure. I figured that just about anything would go there. I checked into the Fairmont and quickly left on a shopping trip.

First stop for me was the Intimate Ladies lingerie shop. I bought a variety of panties and bras, telling the clerk that they were for my girlfriend. Next, I went to a hosiery store and bought copious quantities of stockings in a variety of textures and colors.

Shoes were next. I bought six pairs in several styles, some strappy with high heels. Then, came the toughest part. I needed to purchase several clothing outfits, some conservative and some sexy. I went to Nordstroms and asked a sales clerk who was built somewhat like me to help pick out some outfits. She thought that I was shopping for a girlfriend and commented about how lucky some girl must be.

I was almost overburdened by the amount of clothes that I had purchased and I was forced to return to the hotel before I could venture further. I quickly dropped my packages and headed out once more on my quest.

I located a Mac cosmetics store and a very helpful gay man attended to my needs in the way of makeup, lipstick and nail accessories. We did not even attempt some false pretense. It was San Francisco and he knew precisely what I was up to.

My final stop of the afternoon brought me into a wig store. I purchase a short auburn wig that I thought might go nicely with my green eyes.

As I surveyed my bed strewn with my newly acquired wardrobe, I almost panicked at what I had done. I was at the point of no return. I was ready to begin a transformation that no one could know where it would take me.

I turned the shower on and then just as quickly turned it off. No, I think a bath would be more appropriate tonight. I poured some of the hotel provided bath oil into the steaming water and gently tip toed in. I bathed every inch of my body, sensually soaking in the delicious feeling of the slippery bath water. I took my razor and removed the little body hair that I had. I stared intently at my smallish penis and the little tuft of hair. I shaved the small amount of hair and felt clean and silky as I emerged from my bath.

The cork in the complimentary bottle of wine went pop as I poured myself an inviting Merlot. What next? It was time to dress.

I searched through the packages for the special lingerie that I had selected for this evening. I pulled out a very sexy black satin thong panty and matching padded bra. I slowly stepped into the panties, loving the luxurious feel against my newly shaven legs. I struggled a bit getting the bra to snap, but when it finally did, I had to admit it looked very sexy.

I sat down by the nightstand and took out a shear pair of Wolford stockings. Black shear thigh highs with an elastic band. They had cost me $40, but the 20 dernier silky texture immediately gave me a hardon.

Shimmying into my black miniskirt was one of the most exciting things I had ever done. I paired it with a beige v-cut blouse and a pearl necklace. I completed the dressing by stepping into 3 inch strappy heels with very pointed toes and spike heel. Damn, I was starting to really look and feel like a sexy woman.

The hard part was next, applying makeup. If I had ever learned anything by watching women it was that it’s better to use less makeup than too much. No use looking like either a prostitute or stereotypical transvestite. I gingerly applied the conservative eye shadow and blush. A moderate pink lipstick capped off my facial transition. I applied some very conservative false nails to my fingertips and lacquered them with a pink polish to match my lipstick.

Finally, I took the cute auburn wig and placed it on my head. I stepped in front of the mirror and was absolutely shocked at what I saw. Staring back at me was a very pretty young woman, passable in all respects. I clearly remember thinking, as a tear gently washed down my cheek, that this was the very first time that I had truly been happy and looked forward to an evening out.

My plans for my first foray into the world of womanhood were modest. I would go out for cocktails and dinner then return to my room. From there, who knew where my new life would lead.

I nervously shut the door to my room behind me as I stepped into the hotel corridor and made my way to the elevator. The elevator dinged, the door opened and I stepped into the elevator, joining a very handsome looking man. I stood in front of him, staring at the floor numbers, but I could feel his eyes looking me over.

I entered the hotel lounge amidst a huge happy hour crowd and noticed that the only seat available was at the bar. I breezily walked past tables of half-stewed stockbrokers and attorneys, ogled with each step that I took. I hopped up on the bar stool and seductively crossed my long legs, revealing just a hint of my stocking tops. I saw several jaws drop and the whispering started immediately. I clearly heard one drink-laden businessman tell his companion, “I’d like to take her for a ride.”

I ordered a cosmopolitan and teasingly sipped it down, leaving traces of my lipstick on the glass. Just as I finished, the handsome man that I had seen in the elevator walked up to me and asked if I would let him buy me another. “Of course,” I responded.

He introduced himself to me as Ted Johnson. Not having given much thought to what my female persona would be named, I blurted out, “I’m Christina.”

“You know it’s dangerous for such a good looking woman as you to be alone in a hotel lounge. The men in here might get the wrong impression.”

“And what impression would that be?”

“That you’re available and looking for someone to spend the evening with.”

“Perhaps,” I smiled and seductively crossed my legs.

“Are you in town for business,” he asked.

“No, purely pleasure,” I demurred.

At this comment Ted dropped his hand onto my knee and gently started stroking my leg. I immediately got a terrific tingling sensation and my small penis started pulsating.

Ted leaned over and whispered into my ear, “Let’s take this somewhere else.”

With that, I rose from the bar stool, took Ted’s hand and led him across the bar, through the lobby and into a waiting elevator. It seemed as if one thousand eyes were watching us and I felt like a giggling teenage girl.

As soon as the elevator doors closed Ted took me into his arms in a heated embrace and kissed me deeply. I had never been kissed like that by anyone. He backed me against the elevator door pushing his obviously hard cock against my body. We almost tumbled to the floor when the elevator door finally opened at my floor. It was quite a shock to the elderly couple who were waiting to get on the elevator.

I feverishly fumbled for my room keys in my clutch purse while Ted ran his hands over my tight sexy bottom. As I tried to stick the key in the hole, Ted’s hand ran up my skirt and quickly found my thong. It felt so good as his fingers massaged the crack of my ass.

Now safely in the privacy of my room our passion heightened. I was worried that it would all be over too soon and I wanted our lovemaking to last forever. I was determined to slow things down.

I pulled away from Ted and demanded that he sit on the edge of the bed. He protested but complied. Next, I started a series of very seductive movements intended to drive him crazy. I put my foot up on a chair and sexily smoothed out my stockings, letting him drink in the view of the tops of my nylons. I turned away from him and bent over to pick up some inconsequential piece of paper, revealing my shapely ass and long legs. Ted stroked his ever-growing erection as I moved around the room.

The television in the room had a built-in radio and I turned it on, looking for appropriate music. When I stumbled upon George Thorogood’s “Bad To The Bone”, I knew it was the perfect song.

I pulled a chair from the desk into the middle of the room and then grabbed Ted by his tie and led him to it. I pushed him down and began my naughty lap dance. Nipping at his ear lobes, letting him drink in my intoxicating perfume and rubbing all over him, had Ted ready to cum. But I would not let him.

As the song wore down I straddled Ted and gave him the deepest kiss I could imagine. We melted together as I slowly ground my bottom onto his engorged cock. The only thought passing through my mind during our heated embrace was how was I to tell Ted that the woman of his desire, was different.

My worries and fears disappeared when Ted whispered into my ear, “Christina, I don’t know who you will be tomorrow, but tonight I want to make love to you.”

With this reassuring comment, Ted lifted me up and carried me in his arms to my bed. He laid me down gently and proceeded to undress. He had such a sexy body. I couldn’t wait to run my fingers through the hair on his chest. He finally removed his boxers and I couldn’t believe what I saw. Ted had the most delicious rock hard penis. I rose and sat on the edge of the bed. I motioned for Ted to come closer.

Ted’s hard cock was now in front of my face. I reached out and gently ran my fingers up and down the length of his shaft noticing every bulging vein. I looked up into Ted’s eyes and he could only whimper, “Please.”

My tongue darted out and slowly teased every inch of his cock. It seemed impossible that it could grow even larger, but with each flick of my tongue, it pulsed and grew. Finally, I could wait no longer and I took the head of his cock into my mouth. It was like no other taste I had ever experienced. I quickly began moving my lips up and down his shaft, my saliva making his cock wet and slippery.

I dropped off the bed onto my knees and continued my sucking of Ted’s cock. While sucking his turgid member I gently tickled and played with his balls and enjoyed how they tightened with each playful tickle of my polished fingernails.

My fingers massaged the gentle area behind his balls and Ted’s moans were quite audible and growing more intense with each passing moment. As I sucked his beautiful cock, I looked up longingly at Ted. His face was contorted as he obviously enjoyed every suck and tickle. He forcefully grabbed my head and pulled me tighter into him, furiously fucking my face.

“Christina, I’m going to cum,” he gasped.

I felt Ted’s ass tighten as he began erupting into my eager mouth. I pulled his throbbing cock out of my mouth and licked its head and jacked him while his cum spurted onto my lips and face. Was I a whore for loving the feel of his sticky seed as it dripped off my nose and chin? I lovingly lapped at his cum and cleaned his cock with my tongue.

I encouraged Ted to lie on the bed while I went to the bathroom and returned with a warm towel to clean his cock and my cum stained face. He loved the warmth of the towel and pulled me close beside him on the bed. We rested entwined, kissing and fondling for a heavenly hour.

Throughout our lovemaking I had given no thought to my own sexual satisfaction but I was at peace with myself knowing that I had delivered immeasurable pleasure to my man. However, Ted was troubled that he had been the sole partner to climax and he was committed to rewarding me for my efforts on his behalf.

Ted rose from the bed and grabbed a bottle of lotion that I had left on the dresser. He returned to the bed and gently unzipped my skirt and pulled it off me. He slowly unbuttoned my blouse, removed it and then took my high heels off. Now I was laying on the bed in just my bra and thong and my silky stockings feeling very vulnerable.

Ted rolled me onto my stomach and then pulled me up on my knees, allowing my head to be supported by the pillows. With one hand he pulled the tiny strap of the thong away from my bottom and with the other expertly applied lotion to my derriere. It felt so smooth and sexy to feel the cool lotion trickle down the crack of my ass.

Ted slowly began to run his fingers and hand up and down my crack as he massaged the lotion into every nook and cranny. I felt my pitifully small penis snap to attention as Ted began to probe my previously unexplored rosebud. He gently circled the hole and then easily slipped a finger into my bottom. I felt my bottom clinch and tighten around his finger. I silently wished it was more than his finger, but I would let him decide our course.

While fingering my bottom he took his other hand and started gently stroking my man clit. God, it felt so good. I wanted to let out a girlish scream, but I was startled by the initial discomfort of a second finger and then a third being inserted into my bottom. The temporary pain subsided and the lust and joy returned as I found myself rhythmically thrusting back onto his hand.

I shocked myself with my sluttiness as I blurted out, “Please fuck my ass!”

Ted swiftly flipped me over onto my back, jerked my thong off and rested my stocking clad legs on his shoulders. I spread my ass cheeks as wide as I could as Ted expertly guided his newly engorged cock toward my man pussy. I moaned as I took the full length of his giant cock into my ass. The pain hurt so good.

He started his rhythmic pumping of my bottom as he stroked my clitty with his hand. My man clit had swollen to about three inches in length as I could barely contain my excitement.

My mind flashed back to the years of frustration and humiliation of trying to survive in a macho world as an effeminate man. I had never been accepted for who I was and what was inside of me. Here in the privacy of my hotel room I found the respect and love that I had so craved for so long. Whether it all came crashing down or lasted forever was immaterial to me. For this brief shinning moment, I was at peace with myself and with the world.

These thoughts quickly vanished as I first felt Ted tense up and make a final desperate plunge of his cock into my ass. Simultaneously, my own hips bucked and I shot warm cum all over my chest and stomach. We collapsed together, dripping in cum and exhausted from our night of passion.

I awoke from a deep slumber the next morning saddened to discover that my man had gone. Fearing rejection I was relieved to find a handwritten note beside the bed. It sweetly read: “Christina, our night of love has brought me a new fullness as a man. I must leave you for work, but I will look for you in the lounge at 6:00. I intend to take my new love to dinner.”

Oh what a busy day I would have, shopping and preening for my love. It was a new day and my new life rose with the rising sun.

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