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Pandora's Box

By Alaina Brooks


Do YOU have a First Time Story? Email it to Cindy and we'll publish it!

It was the last of the year - December 1996. A company out of central Texas had contracted me to do some training for their employees the final days of December. I took the opportunity as a great way to get away from the family after Christmas and to enjoy some warm weather in Austin, Texas. It would be fun to spend new Year's Eve as Alaina - I was looking forward to the day. When I began the classes, I was surprised to meet one of my old roommates from college. Tom had always been a great friend and we both enjoyed getting to renew a friendship that had faded with time and distance. He had just moved to Austin and was a new employee and was comforted at finding out that there would be at least one person he would know.

Dec 30th - The first night in town, Tom and I had a great time. We went out for drinks and dinner, told old war stories and got caught up on each others lives. He told me about his family, his recent divorce and his late in life move in career choices. We had a blast going out on the town, drinking and remembering what it was like when we were both in college.

Dec 31st 3:00pm. - The last days seminar went great, I ended it a bit early in the afternoon and could hardly wait to go back to my hotel and begin my transformation into Alaina. Tom came up to me and asked if I would want to go to the party planned by the company - "Come on, it'll be a lot of fun - besides I don't know a soul, and I'd feel like a real shit if I didn't go." I hated to say no, but I made up an excuse that I would just as soon get to bed early and pack because the next days drive was going to be long. He persisted and said, that we probably would not stay out much beyond 1 or 2 and that it would be fun. I knew it would be fun and the thought of walking around a hotel dressed as Alaina on New Year's Eve was just too much fun to ever pass up on. He gave me a hard time about "getting old" but after awhile he gave up by telling me that I would be missing a great party.

Alaina 4:30pm. - I arrived at my hotel and began my transformation with a hot bubble bath. The feel of the bubbles on smoothly shaved legs always puts me in the mood to dress elegantly. I finished doing a close shave and stepped out of the tub ready to slip into the persona of Alaina. I began by applying my makeup and perfume to all the right areas, and then I slid into some sheer black pantyhose. I tightened up my corset once more before proceeding to put on my black lace bra and matching black lace camisole and slip. I checked the position of my breast forms and marveled at how realistic my figure and shape was. I pulled out my black sequined party dress and slipped into it. It was short, three inches above the knee with long sheer black sleeves and a low neckline. At first I thought it might draw too much attention, but my legs are my best attribute so I thought " What the heck". I had just bought a trio of necklace, earrings and bracelet - all real and all very expensive. The gold diamond necklace accentuated the low neckline , and the long sheer sleeves gave an air of real elegance while still looking just sexy enough. I reached around and zipped my dress up while noticing in the mirror how well it clung to my body in the right places. The matching gold bracelet and dangle earrings finished off the trio. The set had been extremely expensive, but the feel of real gold and diamonds made me feel incredibly feminine. I slipped into some three inch black patent pumps. I proceeded to attach my red nails (not too long ) and finished them off with two very feminine rings on each hand. The final touch - a long dark brown wig that hung down to my mid back - long straight and extremely sexy.

7:00pm. I stood in awe at the beautiful woman who I saw in the mirror before me. I had taken my time, and my makeup was perfect The dress, the hair, and makeup made for a nice combination. I had no doubt I could pass off anywhere tonight.

My plan was to walk around the hotel that night and to enjoy the freedom of being able to walk around and not look out of place. The hotel was buzzing with people and most of them were already dressed formal and semiformal - this was going to be fun. A quick cruise through the lobby, a trip up the elevator, and maybe a walk outside - I was so excited I could hardly think straight. I had gone out a couple of times before, but never on such a wild night

I packed a small black sequined purse with emergency makeup, perfume, a brush and an extra set of nails (just in case),my cell phone, some women's cigarettes, and my room key. With a deep sigh of nervousness, I opened the room door and stepped out. People were in the hall and I could feel that a group of older men watched me as I stepped out into the hall. I held my head up high and casually walked by them as I proceeded to the elevator. I could feel them looking me over as I walked by. The feeling was fantastic. As I reached the elevator, I suddenly realized that I had not packed any money, so I turned around and returned to the room. When I passed the men in the hall again, I heard one of them issue a low hushed "U- mm-mm - she's nice looking!" This made me feel great to know that I wasn't getting read.

Surprise

Back in the room, I packed in some cash just in case I needed it. I checked over everything again and headed for the door. I opened the door when I remembered that I would need my lighter if I was going to smoke a cigarette, so with the door half open, I walked back into the room and searched for the lighter I had bought just for this occasion. I turned to head out the door and then to my total horror - there stood Tom in the open door way of my room. I freaked - I gasped and in an almost whisper I felt myself say "Oh shit - Tom !!"

Bewildered he said "What? " We stood there looking at each other for what seemed like an eternity. He looked perplexed and stunned as he came to the realization that this woman was ..... me . After a few seconds, he said:

"Well, are you going to ask me in ?

A smile broke out on our faces and we both laughed as he stepped into the room. From his look, I knew everything would be OK. We talked for awhile and I explained that I was a crossdresser. I had always been a crossdresser.

He was surprised to find out that while we had been roommates in college, that competitive bicycling had been a great excuse to justify keeping my legs shaved. When he and our other roommates had gone home at times, I had a secret stash of clothes I would put on. He never suspected , I did not seem to fill his stereotype of what a crossdresser would be like. He told me that he was aware of what crossdressers were and had been a bit curious, but I had been the very first one he had ever met. He complimented me and told me that if I had not called out his name, he would have excused himself from the room and taken it for granted that a mistake had been made - either he was in the wrong hotel room, or that I had checked out.

"I would never in a million years suspected this was you" he said. "You're very convincing - you make a very beautiful woman"

I felt myself blush. I was so flattered by his compliment.

"I would never suspect you were anything other than a good looking woman. I came by so sure that I could convince you to go to the party with me."

I told him "I'm sorry to disappoint you - Now you know why I didn't want to go out. "

I told him that I had planned to walk around the hotel and maybe walk around a bit outside. With all the people partying in the hotel, I probably would not be noticed.

"That's what you think !" he told me. "I'd lock on to you quick. You're pretty fine looking. Alone, dressed to kill, with those killer legs - I'd have made the moves on you right Now !"

I was sincerely flattered and also scared as I envisioned the persistence of some unknown guy trying to pick me up. The thought sent shivers up my spine - and I suddenly felt cold.

Tom was dressed nice. He was wearing a nice looking three piece suit and looked like he was going to a formal party. He had planned to for us to go and figured that if he came over, that I would not refuse. In a soft and almost child like voice, he asked ..

"Well.... As long as your dressed for New Year's Eve, why don't we still go to the party ?"

I immediately said "NO - no way - There will people there that I will have instructed in the last three days - they'll know me !"

"Look" he said " I know you better than any of those people and if I can't see you right now, what makes you think any of those people will ?"

After a lot of convincing I half heartedly agreed. I felt very confident about my looks, but I was unsure of my voice and we spent a few minutes talking and practicing of my best female voice. After some convincing, I agreed to go.

It would be a wild adventure. I had brought a coat just in case it was cold - I grabbed it and we headed for the door.

We walked out the hotel side by side until we got to his car. I was so impressed - he walked around to my side of the car and opened the door for me. I sat down on the seat and then slid my legs into the car. He closed the car door and walked around to the other side. For a moment I felt a real tinge of panic - here I was dressed as a woman - going to a corporate New year's Eve party - was I crazy ? or what ? There would be people I had been teaching that day. Would they recognize me? Would I be read ? My heart was pounding so hard I almost got out of the car to run back to my hotel room. The driver's side door opened and Tom got in. I told him of my fears and he reassured me that if he could not recognize me, no one else would either.

Thoughts of being in an auto accident filled my brain - visions of being brought to a hospital dressed, made me feel cold.

"Quit that" I thought. "Enjoy yourself. It'll be alright" I pulled my coat around me and decided that I was going to stop being paranoid and enjoy the adventure.

Tom's car was new. He told me about it's new high performance engine and how it was a treat for him after a messy divorce. The plush leather seats were roomy and I began to feel very much like a beautiful feminine lady. Along the way I spoke only as Alaina. I told myself that I had to make sure that if I laughed or spoke that no vestige of my male self could ever come out. Tom commented that I did sound pretty convincing, but to be very careful not to slip up - the voice could be a telltale if I did. I would have to concentrate - I would have to be aware.

We arrived. The house was owned by the president of the corporation, it was enormous. It oozed of rich society and opulence. We walked up the long walk to the front of the house and I could hear the live music coming from the rear. A cold shiver of anxiety went up my spine but the clicking sound of my heels on the walkway made me feel so wonderful, so feminine, that I began to calm down. I decided I would relax, play the part and enjoy myself. When we got to the front steps of the house, an older very elegant lady met us at the door.

"Hi Tom" she said I'm so glad you could make it"

Tom introduced me as Alaina Brooks - I shock her hand gently and in my best voice I said how glad I was to be here. I was afraid she would ask where I was from and how Tom knew me - but she did not. we walked into the main room of the house. The sound of my heels on the smooth marble floors, and the feel of my dress moving as I walked was almost intoxicating. I glanced to my right and saw myself in a large full length mirror. It was a dream come true - I now knew how Cinderella must have felt. Tom and I looked great together. Without even being aware of myself, I took Tom's arm as he escorted me into the main part of the house. I was pleased to see that there were few people there and that It would not be crowded. Tom laughed and told me to expect at least a hundred people by midnight.

We mingled for awhile and Tom introduced me as a good friend from his home town. We made small talk and I enjoyed standing hanging on to Tom's arm while the men made small talk. I had to bite my tongue many times as the male part of me wanted to engage in conversion - instead, I enjoyed just adding comments once in awhile.

After awhile Tom and I took the tour of the house - incredible. The house must have been easily in the area of 5- 7000 feet in area. The artwork, the floors and the general decore of the house talked volumes of a very successful company.

As the night wore on, the band began to play again and people started to dance. By this time we had had a few drinks and I was feeling a bit warm and fuzzy and pretty good about being out. I had always wanted to dance so I asked Tom if he would dance with me. He said sure, it would be fun. we danced several songs and I know I really enjoyed moving to the music especially being slightly intoxicated. We were in the middle of the dance floor when the next song that began to play was a slow song. I was unsure of what to do and I thought Tom would lead me off the dance floor, but to my surprise, he slid his hand around my waist and pulled me close to him. With one arm around my waist and the other holding mine, we moved slowly to the music.

It was so incredible to be held close as we swayed to the music. He led and I followed as we moved with all the other couples on the dance floor. We exchanged small talk and he again complimented me on how beautiful I looked. We danced cheek to cheek and I could feel his breath on my neck.

"You smell wonderful" he said. I now knew how women felt when men complimented them. The dance ended and I so wanted the band to play another slow song. We walked out of the room and onto the rear deck of the house. The night was clear and cloud free and it felt wonderful when Tom took my hand in his as we walked around the well lit pool of the estate. I stopped and reached into my purse for a cigarette and Tom lit it for me. We talked about how I felt to be here. I told him this was the ultimate in any experience I had ever had. I told him how wonderfully feminine I felt, To dance, to be held and how wonderful it felt to have him hold my hand and to escort me as if I were the beautiful woman I felt I was.

He said "How ironic this all is." Here I am out on a date for the first time in seventeen years - the first time since my divorce with Linda, and I find myself out with a woman I cannot have - an illusion."

In a soft feminine voice I whispered "I'm sorry - maybe this was a bad idea."

"Oh no , no, no," he said. "that's the thing that's so ironic."

I thought it would be almost like a college prank to escort you here - I thought it would be something we would both laugh at later - the absurdity of it all..... I didn't expect myself to enjoy it so much."

"I feel almost guilty being here with you" he said.

I reiterated "I'm sorry Tom - I guess I should not have come"

I felt guilty and confused.... had I come on to him... was I playing the woman to much ? Was he getting repulsed at the thought of being out with a transvestite ?

I then asked Tom "Maybe we should leave and you can tell them I had an early flight out tomorrow"

"You don't understand" he told me. "I don't want to leave - I want to stay and dance and have a few more drinks and laugh. I haven't had such a good time on a date in a long long time." We both laughed as if we were kids that had been caught being naughty.

I told him "Thanks" "I don't mean to make you feel uncomfortable" "Please let me know if I do."

We walked back into the house and we grabbed another drink. Sipping on Gin and Tonics made me feel warm and fuzzy inside. The slight wuzziness made the whole experience just that more exciting. We finished our drinks and began to dance again and as luck would have it, we hit another slow dance. I was so excited about being held and slowly moving to the music that I had to contain my enthusiasm when Tom asked me

"Alaina, would you like to dance this one ?'

Softly I replied "Yes, ...Please"

We moved slowly to the music. I enjoyed feeling Tom holding me close to him. All of a sudden the music stopped. The countdown for New Years was upon us. We stood on the dance floor still holding each other as the countdown reached zero. Everyone shouted "Happy New Year!"

At that moment, Tom faced me and kissed me. I had always thought that I would never in a million years allow a guy to kiss me. But I was caught off guard and when I felt his lips press against mine I almost backed away - but instead - I felt myself kissing him back. It was a gentle, romantic kiss. Our lips touching, our mouths just barely open . It was not a deep kiss, but a very loving kiss. We pulled apart and looked into each others eyes. I think both of us were surprised that we had actually kissed. Maybe it was the alcohol or maybe it was just a longing both of us wanted. We both stared at each other in disbelief. Both his arms were still around my waist and my arms were around his shoulders. I could tell it was a first experience for both of us and we were both feeling anxiety. We walked back to our table and ordered another drink. My head was reeling - I could not believe I had let him kiss me.

We continued stayed at the party playing pool, dancing, drinking, and generally having a great time until just after two in the morning. Both of us were a bit drunk and I knew neither one of us should drive. The owner insisted that we leave the car there and that she would pick up the tab for cab fare (although it was free that night). Tom and I walked to the awaiting cab and got into the back seat. We sat in the back talking and laughing and enjoying ourselves . We talked about all the things we had seen and done that night. I could not believe it - I had actually pulled it off.

At one point while we were laughing, Tom placed his hand on my leg just above the knee. I flinched a bit, but it felt good to feel his hand on the smoothness of my hose - and I didn't bother to object any. We arrived at the hotel and Tom and I walked leisurely around the hotel laughing, talking and holding hands. We arrived at my door and I stopped to reach into my purse for the room card. I felt a scared excitement - I felt myself shaking with nervousness. Was I crazy ? Deep down inside, I wanted so much to be kissed again. I pulled the room card from my purse and then looked at Tom. In a soft demure voice I said "I had a great time, Tom. This is was a lot of fun. Thanks for taking me along"

"Thank you ! It was a lot of fun." he said.

"Thanks for everything Alaina" We looked at each other and our eyes spoke volumes. With this, Tom slowly put his hands around my waist and pulled me close to him. He looked into my eyes and, almost instinctively, put my arms up on his shoulders and around his neck. We looked at each other for what seemed like an eternity. Nothing was said - we just stared into each others eyes - and I knew he knew I wanted him to kiss me.

He pulled me close to him as he moved to have his lips meet mine. I closed my eyes and our lips met and we kissed a soft gentle kiss. We both pulled away just slightly as we looked into each others eyes. I moved to him as I closed my eyes again. The feel of his lips gently pressed against mine made the feeling of being a woman so real. His kiss was gentle and very subtle. The feel of his lips, the probing of his tongue was like nothing I had ever imagined. We kissed gently at first and then deeply. His hands moved slowly up and down the small of my back as our lips and tongues embraced . He held me tightly against him. The smoothness of my dress and hose, the tightness of my heels, the feeling of my long hair on the nape of my neck while being held was an incredible sensation. To feel him against me was an incredible high. I could feel his excitement.

We broke from our embrace and we both went into the room. We talked about the night's experience and how much fun we had had. We talked of future plans to maybe get together - although I knew it would never be arranged. We had an awkward moment of silence where I think both of us felt a little unsure of what to do next. At this point I stood up and Tom said goodbye and wished me well.

He left and I sat on the bed looking at myself in the mirror. What had happened this night ? Had I crossed the line ? What were my feelings on the whole thing ? I had enjoyed myself a thousand times more than I had ever expected to. This had been a fantasy I had only dreamed about for years. It was then and there that I came to the realization that I had truly opened Pandora's box ... and things would never be the same again.



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