The Birth of a Sissy

After some careful planning and serious consideration I had made the decision that I would use my parent's birthday present to me to travel to Orlando, FL. They have a University there and tons of other things to see. For a kid from a little town in NC it felt like the biggest city that I could visit and still be safe (they have the house of mouse what's the worst that could happen). It was settled and within a few hours of talking it over with my parents they had purchased my plane ticket, gotten me a room at a hotel near a convention center (because, you know, cheaper than most other places) and had set up a campus tour for me. Being from a little place you kind of have a warped sense of distance between places. It turns out the University and the hotel were nowhere near each other. So yeah I never made it to the campus.

I had busied myself for several weeks leading up to the trip. I had decided that I would spend my whole trip wearing panties in public and every chance I got. I had started to wear them more often and had gotten to the point that I could pretty well control the erections. I had worried for some reason that when I got to the airport they would ask to inspect my suitcase and I would be outed. So I had taken special consideration on putting my collection of panties into tube socks, folding them together and stuffing them in my shoes. I had taken my contraband dress and placed it in the leg of my dress pants and folded those too. As the time drew nearer to my trip I was a bundle of mixed emotions. Should I be doing this, could I actually do this, even better would I actually do this?

On the day of my flight I decided that if I was going to actually do it I was going to have to start right then and there. I dug into my suitcase and withdrew a sock ball from my shoe reached into a sock and pulled out a cute little yellow cotton brief. I slipped them on and slid my shorts on. They were so soft and light and rode just slightly up my pert ass. As I rode the hour and a half to the airport my folks droned on about staying safe and checking in regularly. About how proud they were that I was growing up so fast and to not feel pressured to go to school so far from home. My mom at least ten times reminded me that her and my father met at a community college forever ago.

After what seemed like forever I finally boarded the plane to sunny Florida. On my short flight down I chatted up the business man next to me. It turned out that my folks had gotten the hotel they got because there was a convention at the same hotel and a couple of the big companies scheduled to attend had backed out. According to my new friend there was a sleepy little bar in the hotel but the real action was out and about near the convention center. He was also nice enough to offer to split a cab with me to the hotel. He was a father of three who traveled all over for business, but he loved Florida and always looked forward to "blowing off some steam"! I knew what that meant and no doubt he "blew off steam" everywhere he visited. He was a mid forties business man who's best days had probably already passed him by. All I could think was how bad I hoped that I would not have to spend my life traveling to "blow off steam", but at the same time here I was traveling somewhere to be free of the community I lived in. We bonded over playing high school sports and I could see that he had probably once been very athletic, but comped dinners and breakfast buffet's had put some extra weight on his 5'9" frame.

The cab ride took what felt like forever, again spatial awareness I guess. But as we pulled up to the hotel I was amazed by the amount of activity occurring all over. This was the place that you could get lost and blend into if you wanted to. I handed my new friend some money for my half of the ride and we grabbed our bags from the driver. In the lobby the level of busy did not subside in the slightest, as I waited in line to check in the area was awash in business men and women as far as the eye could see. The hum of conversation was incredible. I got my room card and shuffled off through the crowd. I was on the eleventh floor and shared an elevator with a group of very tan gentlemen that were speaking a level of Spanish above the two years I got in high school. I disembarked the elevator and found my room, as the door closed behind me I placed the safety bar for extra security and stripped down to my panties. I walked to the window of my room and peeked through the shades, outside was a plethora of opportunity and activities. I could see a Walgreens and several other shops, I waned to go shopping. I jumped in the shower and cleaned the flight off of me, toweled off and slid into a fun little gray lace thong, some shorts, a bra and a heavy tee. I trotted down the hallway to catch the elevator and within a few minutes I was out on the busy street in the heavy Florida heat. The thong seemed like the best idea I had ever had.

My first stop was the Walgreens, which though new and brightly lit, had very few customers. I quickly dashed to the cosmetic aisle and began picking up the necessities (lip liner, mascara, etc.) then I made my way to an aisle that had women's hosiery and to my wonderment I found bra lifts (inserts to make it look like I had breasts). I was in heaven, I was buying things for myself in a place where no one knew I existed. I scurried to the counter to pay and without even a sideways glance from the cashier I was out of the store with my bounty. Next I hit up a Payless shoes about three stores down and with little trouble had found a pair of black heals women's size 12 that fit my feet. Another quick cash transaction and I was headed back to the hotel. On my stroll back I passed a tourist trap shop that caught my eye, all the manakins in the window had different colored wigs on. I popped in and to my amazement found an aisle of costumes with a dearth of wigs to choose from. Being a natural blond with blue eyes I decided on a jet black wig. I thought why not match my dress and set off my eyes. At this point I was so thrilled with what I had acquired and almost skipped back to the hotel.

In a matter of 45 minutes I had found all of my goodies within one square mile, Orlando really was a magical place. As I walked back into the lobby I became painfully aware that I had only eaten some airplane pretzels and a cookie all day. I walked into the "sleepy little bar" my business man friend had told me about. He was completely right about the place, with all the bustle around it, this little bar was inhabited by three patrons and two wait staff. I sat down at a booth and looked over the menu, settling on a burger and some fries I flagged down a waiter and placed the order. The food was nothing to write home about but in my hunger state I wolfed it down and headed up to my room.

Once the door closed behind me and I had locked the lock I was a light with giddy. I spread out all of my goodies on the bed and began unpacking my bag. I stripped down to my bra and panties. I slid on the hose I had just bought and slid the bra lifts in. I slid my dress on and went to work applying my make-up. I fitted my wig and straighten the hair the best I could, then sliding on the heels I began to walk to the bathroom to take a good look at myself. Unfortunately walking in heals is not a natural thing and I toppled quickly, bouncing off the corner of the bed. I abandoned the shoes and walked into the bathroom. I was amazed at the woman that stared back at me from the mirror, sure my make-up game needed more work but for all intents and purposes I was a passable woman. I gave the heels another try just to see what the finished product could look like. Standing still in heels was still a task and unfortunately made me 6'5" which to me seemed less passable then I had been before. So heels were out, but in that moment I was probably the happiest with myself I had ever been and in my triumph I walked to the window of my room and threw open the curtains. For anyone interested in looking, there I was, proud as a peacock. I took it all off and made a few notes on some makeup changes, slipped into a pair of Lycra boy shorts and crawled into bed for the night.

The next morning I woke with a massive case of morning wood. I stoked myself to climax in my panties, cleaned up, slid on a basic black bikini cut, some shorts, a tee and headed down to continental breakfast. The place was abuzz with activity and the breakfast area was packed with the business crowd, all dressed to impress and ready for their days. While I ate my Belgian waffle I was taken aback by some of the gentlemen in the group. They had on fitted dress shirts and suit coats that were tailored to there form. Before I could realize I was doing it I had been caught staring at a handsome 30ish business man in a grey suit with a lights blue dress shirt and peach colored tie. He was probably my height with light brown hair. What had caught my attention was the form fitted pants that made his muscular buttocks look amazing and they were tight enough that the outline of his flaccid penis was slightly visible. He didn't see me staring but I became quickly aware that the gentleman he was talking to was looking right at me. I quickly busied myself with something on the table and when I looked back up the man in the grey suit was looking at me. OMG he had beautiful green eyes, I freaked, turned flush red and scrambled back to my hotel room. Once back in my safe place my embarrassment was brought to bare by the fact that I again had a raging hard on and had probably run from the lobby with said boner. What was happening to me? Aside from the confusing moments with Nate I had never ever looked at a man that way.

After watching some tv to take the edge off I decided to get some fresh air and stroll the strip near the hotel. There was something to do on every corner of every street I walked. As I ventured down a less crowded street I found that I was wandering to places that Orlando probably hoped few people would see and after a few blocks I decided to turn back the direction of the hotel. There were still shops down the street I found myself on but they were not as tourist oriented. They seemed a little more geared towards the people that came to town to blow off some steam. Being from a small town I never thought of myself as a prude, so in an effort to expand my horizons I chose to enter an establishment that advertised itself as an adult novelty and book store. Inside I was bombarded with so much exotic merchandise I was momentarily embarrassed. Maybe I was a prude. After the initial shock wore off I began to explore shelves of dvd's and insane adult toys, I must have looked like a slack jawed yokel for sure. Then I came to a wall of exotic lingerie and was instantly mesmerized. I walked along touching all of the fabrics and textures marveling at the revealing under garments that my mother would never have imagined in her lifetime. I decided I had to own something from this store and settled on a red nylon/spandex bodysuit. Again at check out I was shown very little interest by the heavily pierced young lady who rang me up, whom beside for carding me when I walked in never even looked at me again. Back into the Florida humidity I high tailed it back to the hotel.

As I slid my new purchase on in the mirror of the bathroom I was amazed at how sexy I looked and felt. I was also slightly embarrassed by the fact that the cut of the bodysuit made it painfully obvious of how unkempt my pubic hair looked. I removed the lingerie and proceeded to manscape myself to a satisfactory level of bald and slid my new outfit back on. The feel of the fabric on my freshly shaved body was incredible. I pranced around the room, I laid on the bed, I sat in he chair and lastly I wandered to the window. Before I had thought through my actions, in the euphoria of my current situation I flung the curtains open and stood in the window with the sun warming my body and in full view of anyone that wanted to glance my way. I wasn't embarrassed, I wasn't afraid, there was no trepidation, I was ALIVE!! In that moment I decided that I wanted to show anyone who wanted to see me who I really was. In that moment I decided that I was ready to go out in public as I was meant to be seen.

I took a shower and went about making myself up. I slid my body suit on, pulled on my nylons, slid in my lifts, slipped on my dress and wig. I put my most concerted effort into my make up and when I had finished stood in the mirror staring in wonderment at my handy work. I took a few deep breaths and exited the room (shoeless because I still had no idea how to walk in heels). I caught the elevator to the lobby and shared it with a couple that was headed to the pool. They had no interest in me in the slightest, though I wondered if they thought I was passable. As we hit the lobby I was surprised at how quiet it was it seemed everyone had found somewhere else to be for my grand reveal. I strolled into the bar and found myself at the same corner booth from the night before. The lighting was pleasantly dim and I was relieved by the lack of patronage at the place. The waiter came and with my softest voice I could muster I ordered. Not even a sideways glance affirmed that maybe I was actually pulling this off. As I sat and waited a couple of middle aged business men sidled up to the bar and ordered drinks. Occasionally I would catch one or both of them looking my direction and when eye contact was made they would quickly look away. By the time my food had arrived their twosome had grown to a foursome and the conversation volume had tripled. The youngest in the group was probably in his mid thirties and he was obviously a junior partner where ever they happened to work. He did however seem to be the most willing to look my way as I caught him in eye contact frequently. As the waiter cleared my dinner plate the bartender came to my table and presented me with a glass of wine from the gentleman at the bar.

I had dabbled with alcohol in high school keeping my status up with my peers but this was different I was in a drinking establishment and I was convinced at any minute that I would be carded by the bartender. So again as soft as I could, I politely declined the drink and asked the bartender to tell them thanks but no thanks. I rose from my seat and began to exit the bar, still worried that I was too young to be served and would be quickly outed as such if I stayed. I hurried myself towards the elevators in an attempt to escape to my room to escape, but before I got to the elevator bank I could hear someone calling out from behind me.

"Hey... Hey... Hey dear, hold up for a second..." Came the call from a pleasant baritone behind me. I was frozen in place as the voice got close to me very quickly. Within a second the young business man slid in front of me in an effort to engage in conversation. I just stared at the floor in shear terror. This was where I would be found out and this was where my little fantasy would come to an end.

"Hey, listen I didn't mean to offend you. I get it a pretty lady like yourself probably has to deal with getting hit on all the time. I just... I was trying to get the other guys off my back, they have been riding me all night about being too timid. I just want to say I'm sorry if I offended you"

"Thank you for the apology, I... I am not old enough to drink yet and I left so you wouldn't get in trouble." I was giving my best effort to sound as effeminate as possible and remained staring at the floor.

"Oh! Oh man I am... You just looked old enough from where I was sitting. I thought you were in town for the convention too. My name is Brian." And he extended his hand in a friendly gesture.

"I'm... I'm Katie" I said as I accepted his hand shake and as he raised his other hand to cup mine I noticed a wedding band. He must have realized that I had seen it as he quickly withdrew his hands from mine.

"Well now that I have made my amends, I can head back to my friends..."

"Wooohooo, that a boy Brian!!" Was the chorus of cat calling coming from across the lobby from his cohorts. They were already pretty well inebriated as they walked out of the lobby and into the night.

"I guess you had better catch up with them." I said as I began to turn towards the elevators.

"Oh not really, I know where they are headed and trust me they will still be there if I want to see them again tonight. If you would allow me to I would love to buy you some dessert at the bar to make up for my faux pas earlier. You game?"

To that point I still hadn't stopped looking down at my feet, but with his words I looked up and met eyes with him. His eyes were a light brown and came close to matching his hair. He looked into my eyes and from nowhere I began to feel light headed. He smiled at me and I smiled back. "Yeah that would be great!"

What was I doing? He was obviously a married man and if he was looking to blow off some steam then he was barking up the wrong tree. Where did I think this was going to lead? Was I ready for this leading anywhere? Within seconds he was pulling out a chair for me at the table, I obliged the gesture and sat. As he sat down he removed his suit jacket. His jacket was too big for him and as he laid it down on the seat next to him it was apparent that he was in good physical shape. His dress shirt was much better fitting and accentuated his muscle tone. He was a very attractive man and the more I looked at him the more I became aware of the light headed feeling. He quickly broke the silence and began to talk about his relatively uninteresting job. His aspirations to become a partner at his firm within the next ten years. How he was going to do night school to get his MBA and break through the glass ceiling. All the while I nodded and smiled and watched his left ring finger as he spoke with his hands.

"Okay so let's address the apparent elephant in the room... Her name is Elizabeth, she is a school teacher back home in Denver and we were high school sweethearts. We have two young sons and she has not touched me in a sexual way since our second was born three years ago."

"Oh, um, I'm sorry..."

"Hey I am the one that started this little rendezvous, you have done nothing more then keep a lonely man company for an hour" he said with a reassuring smile. "I'm sorry if I have over stepped my bounds and made you feel uncomfortable."

"No, it's not that at all, I just didn't want to give off the wrong impression. We are having a good time and I just..." Before I could finish the sentence he slid his right hand up my left thigh, under my dress and right to my half hard cock. I sat in utter terror and couldn't pull back in time to stop his discovery from happening. As a thousand scenarios poured through my head on what was going to happen next he placed his hand squarely on my cock and leaned in, planting his lips on my mine.?????? His lips began to part and the light pressure of his tongue pressed my lips. I obliged his advance and opened my mouth to allow his tongue. I caressed his tongue with my mine and let out a very faint moan, with that he wrapped his fingers around my now erect cock and gave it a slight tug. He then separate from our kiss and laid a room card on the table.

"Why don't you take a second to compose yourself and come join me upstairs #926." And with a wink he stood up, grabbed his jacket and walked out using his jacket to conceal his own erection. I sat there for a good 45 seconds before I could even begin to think. Had that just really happened? Had he known all along? Should I really go to his room? The last thought was a no brainer. The answer was yes, totally yes. I took about five minutes to "compose" myself and picked up the room card. I walked slowly through the lobby and into the elevator. As the doors closed I leaned against the railing to gather my bearings and quickly realized my heart was thundering out of my chest. To the best of my knowledge I had never had a reaction like this before. No sexual endeavor with a girl had ever aroused my senses like this. The doors opened and I walked to room 926. I stood outside the door and second guessed myself for a split second before my hand instinctively slid the card into the reader and the door beeped its acceptance.