A Very Happy Holiday To Me

I don't know if it was a dream or just something that happened but it was Christmas and I felt sore and achy all over but with a wonderful feeling none the less.

I am a crossdresser who is trying now to discover and explore his female personality and can now happily tell of who I was in the past, who I am today and perhaps who I will be in the near future.

I began my life as a normal child until the age of 18 years old when I went into my parents' bedroom to look around. It was a typical bedroom with a large bed, hardwood floors, a huge closet full of my father's and mother's clothes and two very large dressers each with a mirror attached above them. I knew my father had the usual items in his dresser so there was no reason to search any further but I never knew what exactly was in my mother's dresser. I did know that my parents and my sister were not going to return back to the house for a while so I decided to see what was in mother's dresser.I glanced around the room as if someone was actually watching me and then closed the door quietly. I got undressed and took off my glasses putting them nearby just in case I needed to look at something a little better.I put my hand out as if wanting to open a drawer but pulled it back a couple of times trying to find the courage to look inside. I thought that I would never do this and saw my own clothes on the bedroom floor and told myself that I may never get the chance to do this.I hesitated a little longer but I finally made the decision to see what I was so eager to find.I slid the first drawer open slowly and to my surprise was some of the prettiest things that I had ever seen.

 I noticed everything was so neatly folded and organized and again I paused to think about what I was about to do.I peeked inside the drawer and saw a brand new red underwire bra still with the store's tags on it and right next to it was a pair of matching panties.I reached in the drawer and pulled both of the things out holding them each in my small hands. I had a feeling of something was wrong with doing this nearly dropping them to the floor.I had a strange feeling thinking that if I was caught that I would have to face the consequences of my actions and a great deal of bitter criticism from those outside of the family. I shrugged my shoulders and decided now I had to do this or just forget about it entirely.I put the panties on the top of the dresser and unhooked the bra trying to remember how to put it together once I put it on. I lifted the bra to my body and put my arms through the straps and quickly closed the hooks in the back and grabbed the panties raising one leg and then the other and slid them slowly up my legs until it reached my waist. I was amazed about how easy it was to do this and thought that my mother did this every single day.I turned my body towards the mirror and saw what I had done. I noticed that I was flat chested and went in my father's dresser to put a pair of socks inside the cups to make me seem that I had the right features. I stood in awe for a while but thought it was the best time to becoming who I really was. I never again tried to do this but I kept on thinking back to this day.

In a couple of years later, I went to the high school in town where I had more female friends than just being with the boys of my same age. We shared all of innermost secrets, telling about the crushes we had on a boy, makeup and hair advice, all about our boyfriends, life at home and everyday events. The girls that I made friends with even invited me to to go to the mall together when they shopped for new clothes asking me as if I really knew on how it looked on them.They even tempted me to try on different clothes with them but I always told them that I was not that kind of person. Well, just not yet I thought to myself.The rest of my high school days went by fast and when I graduated my parents bought me a new car and gave me a check with an amount that startled me. I promised my parents that I save this money and would put it a bank account where I was not allowed to use it without their permission.

I knew my college education was fully paid for by my relatives and attended the university close to home but I lived in a dorm with men from the town I grew up in and others around the country and the world.I studied hard for four years receiving my degree in Business Administration with high honors. I proudly showed my degree to my parents and my sister and told them it was time for me to find my own apartment and that ever elusive good paying job with good benefits.

After a few weeks, I found a nice apartment nearby the house with a large kitchen. a walk in closet with plenty of space for clothes, enormous dining and living room and the biggest bathroom I had ever seen. The rent was not too bad and it seemed everything I needed was close at hand. I continued my search for a job and found one with a major law firm who was always in the news as their new research associate. I really liked the job with all of assignments and resposibilities I was given and had enough money to buy new furniture , a better televsion and a lot of new things for the kitchen and bathroom and still had enough to save in my bank account. I even went to the best electronics store and bought the most expensive desktop computer I could afford with a lot of the extras.

In my free time, I decided to find out more about the online dating services I heard so much about and discovered by filling out the different profiles that I was truly a crossdresser. I also subscribed to a number of women's beauty and fashion magazines and newsletters and requested the mail order catalogs I needed to purchase the clothes I wanted so I could avoid any problems of doing so in public. I eventually found the right catalogs for everything else I needed but never did nothing more than put them in my storage shed in the basement. I met a lot of nice people online but never went out with them socially until I met Bill. He seemed to be a great person and we shared a great deal in common and he was sympathetic to me. We chatted for hours every day and I felt confident enough to give him my telephone number.

My desires and urges to develop my feminity grew stronger and I began to let my hair and fingernails grow longer ever mindful of my appearance at work and in public. I found a woman near the apartment who helped to give me private makeup lessons and also taught me the best ways to act and behave at all times as a woman.

I talked to Bill more and more and then he asked me if I wanted to go out for a date at a friend's house for a Christmas party as long as I could go with him as his girlfriend. I said that I would have to think about it but finally said it was fine.

The days before our first meeting went by so very slowly but I got a long e-mail message from Bill with all of the details for the party. I knew that I had to get my hair and makeup done outside of my apartment and get all of manly body hair removed so that I could be soft and smooth to the touch just in case there was to be any contact between us. I went to a local beauty salon to have my hair cut and styled as if for a woman and a complete waxing but left my pubic hair in the shape of something that would cover a vagina and let them dye it a hot pink color. My co-workers said I looked great.

The day before the party I returned to the beauty salon and told them to give me the absolute best makeover including a deep facial and everything else. I told them that my makeup had to last for a few days and be very dramatic and glamorous. When I finished my appointment at the salon I went to a jeweler and got my ears pierced and purchased a couple of pretty dangling earrings, a long necklace, a bracelet, two beautiful rings and a women's watch to wear. I got back to my apartment and went directly to my storage shed to pick out the nicest things I could find for the party.

I had a restless night of sleep and woke up with my heart beating hard in anticipation of things yet to come. I got up and took a long bath using my favorite bath oil which had a nice and pretty smell. I was very careful as not to ruin my new hairstyle and checked myself to see if had any traces of body hair that needed to removed. I was still soft and smooth all over and quickly dried off and dusted my body with a lightly perfumed powder. I went into the bedroom staring at my clothes thinking I was unsure if I was ready for all of this. I kept daydreaming for a while but was startled when the telephone rang in the kitchen and it was Bill reminding me about tonight's plans.He told me to be ready at 5:00 and he would meet me at my apartment and whispered softly in my ear that he was in love with me. We talked for a short time and told him that it was time for me to get dressed. I went back to my bedroom and started slowly to put my clothes on. I chose a beautiful cobalt blue dress with matching high heel shoes and black lace top stockings and the nicest lingerie I had. I sprayed my best perfume on all of the right places on my body to complete the effect realizing that now I was no longer a man but a pretty woman from head to toe.

The time after I got ready seemed to go slowly and then promptly at 5:00 Bill rang my dorbell and let him come upstairs to my apartment. He was absolutely handsome and nicely dressed and groomed and gave me a flower and kissed me gently on the lips. We talked for a while and then he said it was time to go to the party. We got his car where he opened the door for me and helped me to sit down so not spoil my outfit. We drove for quite some time and finally arrived at his friend's house or should I say mansion in the middle of nowhere. Bill opened the door for me again and helped me to my feet. We went up to the oak door and rang the doorbell and was greeted with a smile by Bill's friend. He said that he was very happy to see us and we entered to a house full of people almost to the point of being a little bit overcrowded. I noticed how nicely the house everywhere was so nicely decorated for Christmas and a huge Christmas tree all lit up stood in the middle of the room. A short time passed when someone asked me if I wanted anything to drink and I agreed and asked for a glass of wine. Before I knew it, I was handed my glass, raised it gingerly to my lips and sipped it. It tasted so good. I began to mingle with the other guests until we were told that dinner was ready. Bill and I walked over to the table with neatly written cards designating where everyone should be. I reached my chair noticing Bill was next to me on my right side. Bill gently pulled out my chair and I sat down and then Bill pushed me slowly towards the table.We were served a salad with a very unique dressing followed by an elegant meal finishing up with a huge piece of chocolate cake and coffee. I looked over towards Bill all during dinner and he always smiled back at me. I got up from my chair and began again to talk to the guests noticing that my wine glass was never empty. Around 1:00 in the morning Bill came over and it was time to leave and I saw a sly grin across his face as if he knew about something he wouldn't discuss. He said goodbye to his friend and told me that three other men were coming with us but that is all he said.

We all get into the car and drove the long distance back to his apartment in utter silence with smooth jazz playing on the radio. I kept wondering about lied ahead and asking Bill what he was planning but he just kept silent paying closer attention to the road instead. We arrived at Bill's apartment and he opened the door for me and he he helped me stand up wobbling a little bit from all the wine I had to drink. We walked up a short flight of stairs that creaked loudly and Bill let us in nodding his head to the men as if to acknowledge it was time to start. Bill hurriedly caame over to me, smiled broadly and then kissed my deeply and passionately on the lips. I felt my body grow weak yet at the same I felt I was now ready for anything. Bill told me to find his bedroom and I went there without any hesitation. I pushed open the bedroom door and saw beautiful white lingerie laying there on the bed with a note saying I was now to have the best time of my life. I got undressed and put on the lingerie which fit me perfectly and I felt so incredibly pretty and sexy. I noticed the lingerie had no bra cups and was crotchless below my waist. I stood there for a while and did not even hear the men come into the room to join me. Bill once again came over to me and kissed me even better than the first time. I said I was now ready and told the men to get undressesd and go over to the bed. The lingerie moved softly on me as I went over to the bed with my thoughts filled with ideas of what was about to happen. The first man I was with in the bed kissed me hard and said he wanted me to give the best oral pleasure he ever had. He approached me with his penis standing straight out and very erect and I opened my mouth wide and took every inch of it down to the bottom of the shaft and moved my my mouth up and down. He closed his eyes as I continued to please him and then screamed that he was ready to climax and ejaculated his sperm in a long stream in my mouth.

I swallowed almost every drop and licked the top of his penis as if to clean it. He told me that was the absolutely the best he ever had and kissed me again.The next man came over with the same idea and I did exactly as before taking him fully in my mouth but this time he pulled his penis out of my mouth and ejaculated directly on my face. The third man came over to me and said he wanted me to get on my hands and knees so that he could penetrate me from behind. I shifted my body for him and he pushed his very erect penis inside of me and began to thrust himself long and hard inside me. I quivered as the rhythm of his movements felt so immense until he moaned that he was ready to climax and sent his sperm in a steady flow inside me. I felt Bill's own eyes upon me during all this time and then told the men to leave us alone.He walked over to me and kissed me all over slowly taking my lingerie off and said he wanted to experience everything he saw before. I leaned over to him and took him in my mouth moving my mouth in a constant motion and moaned that I needed to feel him inside of me. I moved my body to take every inch of his penis deep inside me and he entered me slowly making sure I enjoyed it. We moved together in harmony as if we had done many times before until he whispered he had to climax and ejaculated his sperm in me.He kissed me intimately and said he was so elated and pleased what I had done tonight. I felt my body go limp with exhaustion and stretched out on the bed wanting to sleep for a while. Bill lied down closely to me as I drifted off into a peaceful rest. I woke up soon after and excused myself to relieve almost all of the wine I had to drink and clean my body. I returned to the bedroom and then realized that I never brought any of my own clothes to change back into. I got dressed back into my clothes and went into the kitchen to join everyone. We all talked for a short time and then said it was best that we leave to spend Christmas with our family and friends.

The men agreed together and each one came over to kiss me one final time saying that it was the best time they ever had. Then each of the men told me goodbye and left quietly out of the apartment one by one. Bill told me to stay with him for Christmas Day but I said I wanted to go home and sleep and remember this. Bill shook his head slowly saying it was all right with him and we left the apartment together holding hands all the way down the stairs until we reached his car. Bill opened the door for me and I sat down moving in a such a way that I could be close to him as he drove. When we finally got to my apartment Bill turned his head towards me and kissed me gently with a little tear coming from his eye. I got out of the car quickly so not make my neighbors aware who I was in the dress and ran as fast as I could to my apartment to change. I took a hot shower to wash my body and take off the makeup I was wearing once again becoming a man. I put on my shirt and jeans on and went to the living room window and saw Bill was still there. I went back downstairs to tell him goodbye for now and said I hoped that this was only the start of something very special. Bill smiled and drove away waving his hand to say he was okay as he left sight of him.

I went back in my apartment and turned on the radio listening to the same smooth jazz music we had heard before in the evening. I made myself a cup of coffee and a bagel with cream cheease and strawberry jelly and began to reflect on what just happened. I finished my breakfast and went into my bedroom to sleep. I slept for a short time and got up to check my e-mail messages and saw one from Bill with a heart icon attached to it. I read it over and over again and then saved it in my contacts section of my account.

I still talk to Bill every day and he still says that he loves me and wants to continue to be together with me but this time as a real couple. Well, let's wait and see what happens next.