Twas the night before Christmas and all through the house, not a creature was stirring except for me. Here I was alone on Christmas Eve. My girl friend had broken up with me the day before. After being intimately involved for almost a year she broke up with me telling me I was not masculine enough for her she then told me that over the last month she had become involved with another man who treated her right. This other man had asked her to be with him for Christmas and she had accepted so here I was wallowing in self pity on Christmas Eve. It was approaching midnight and I had watched enough heart warming Christmas stories to make me puke but I knew that I would not be able to sleep. It was the same with every relationship I had ever had first they found me refreshing not being a masculine asshole then they walked all over me finally they left me for the same type of person they had hated so much before.
Just as the clock struck midnight the Westminster Chimes tolled out the death of my relationship and I sank deeper into depression. Just as the clock tolled the last stroke of midnight I heard a noise upstairs and was startled out of my reverie. Picking up the remote control I turned the TV down low and there was lots of noise coming from upstairs. Just as I went to get up out of my recliner I heard noise coming from the fireplace little bits of soot and ash fell down on the grating. Starting to get worried I rose from my chair moving toward the fireplace I saw a boot come down the chimney. I picked up the fire poker as another boot came down and then a red leg. I went into shock as a gloved hand appeared. Finally the whole man did the impossible and climbed out of the fireplace into the room. Santa Claus, white beard and red hat, little spectacles standing right there in front of me. Gesturing at the fireplace poker he said "You won’t be needing that, I’ve come to give you something not to take anything away". I took two steps backward and sat down heavily on the couch. Santa walked over dragging his bag with him and sat down in the chair across from me he picked up the bottle of bourbon and poured himself a shot and asked "Will you join me ?" as he poured another shot passing it to me he smiled an incredible smile. He toasted me and I joined him as we downed the shots. Finally finding my voice I said "But this is impossible you don’t exist." Santa smiled again and chuckled in a low humorous belly laugh finally saying "I would beg to differ with you but I really am here." My mind was reeling as lots of things rolled through my head, somehow just looking at this jolly man had a soothing effect on my soul. Santa finally spoke "Tony Bryant, I know you are very distraught this evening. Things happen that drive nice people to the brink." Not being in any mood to listen to this impostor I interrupted him screaming "I don’t know who you are or what you want but get out of my house, Now! I am in no mood to listen to any of your crap." I again lifted the fire poker in a threatening manner. Santa just smiled at me again pouring us another shot of bourbon saying "Here Tony, this will soothe you." As he pushed the shot glass over to me. His smile and presence was intoxicating and I started to relax despite myself. Santa continued "Proof you want proof ? Do you remember that mother with the two kids last summer that you stopped and changed the tire for even though it meant being late for work and catching grief yourself, don’t think that goes unnoticed. All that work you have done for the children’s center. Paying your sister’s electric bill and never expecting anything in return. I picked up the shot and downed it in one gulp. Looking into the kindest eye’s I had ever seen I finally believed and asked " Why are you here I thought you did your work after everyone went to sleep?" Santa responded "Most of my work can be done after you are asleep but some of my gifts can only be done in person, some require extra special attention." Santa picked up the bottle of sleeping pills and looked me in the eye’s then he tossed them into the fireplace and said "This is one case that requires special attention. We reviewed your case for a long time before finally coming up with a solution." Santa reached into his bag and took out an impeccably wrapped present and tossed it into my lap and smiled at me saying "Open it." Opening the package I was surprised to find a beautiful red and black Christmas dress unfolding it I held it up finding the top to be a red and black silken material the skirt came down in three layers with a silken inner slip flaring out in a feminine manner. Very nice and sexy. I looked over to Santa and said "I think you brought this one to the wrong place." Santa replied "No I am quite sure I hit this one right on the money, remember I know everything."
Santa picked up the remote control from the table and pointed it to the Television and pressed the play button. An ten year old boy appeared on the screen. I recognized this boy, He was me. Turning to Santa I said "Where did you get this I don’t remember any one filming me. I don’t even think there were video recorders then." Santa looked at me sternly and said "Be quiet and watch !" Turning my attention back to the screen you could see a very distraught little boy the surroundings were definitely Christmas morning. I remember not liking Christmas very well. The film showed me unwrapping a football, Tonka trucks and a Cowboy suit. You could obviously see that he was much more interested in what his sister was unwrapping. A Barbie doll and clothes a pretty dress and the all the wonderful mysterious under garments. Then running up to hug and kiss Mom. Dad walked over and said "Come-on slugger get some clothes on so we can go out and toss the football. Reluctantly the boy got up to go. Santa turned to me and said "So what was that all about ?" Turning back to the screen Santa fast forwarded to The boy and his Dad Tossing the football. Santa said "You were not even making an attempt to like it." I responded "I did not like the sport, Still don’t if I showed any interest he would start to tackle me and I would end up all bruised. I wanted to play with my sister." The scene on the TV moved to one of the father finally giving up when he threw the ball a little to hard and the boy started to cry. The boy was sent to his room with the father saying "If you can’t even play catch you can’t go see your cousins either." Looking to Santa I said "I was pretty mean to him, But the family gatherings were even worse." Santa looked back and nodded to the TV hitting fast forward again we watched the family leave with the boy staying home. After the rest of the family left we see the boy look around the house finally going to his sisters room. Stripping off all his clothes he went over to the dresser and pulled out a ruffled pair of panties and put them on. You could see his little hairless cock getting erect in the panties. Again he went into the dresser and pulled out a training bra You could tell by his actions that he knew where everything was. The look on his face was ecstatic. He then pulled out a pair of white tights and rolled them on to his legs. As he stood up and looked in the mirror you could tell he liked what he saw. Going to the closet he looked in and selected the prettiest petticoat which he put on and the most feminine ruffled light blue party dress that he also put on. Bending over to select a pair of black patent leather shoes you could see his ruffled panties and petticoat under his dress. Returning to the bed he put on the shoes and went to the dresser taking a brush he started to brush out his longer than usual hair finally satisfied with his hair he went down the hall to his parents room to look in the full length mirror. Standing in front of the mirror you could see him do a pirouette and just stare at his image, He made a very pretty little girl. Watching myself in this long forgotten scene had me aroused, But I knew what came next. Turning to Santa I said "Could we stop this now? I don’t need to see anymore." Santa said "No its just about to get interesting."
Turning back to the TV there was a sound from down stairs. I could still recall every word and circumstance. The little boy froze, The fathers voice came up the stairs "Tony, I am sorry you can come with us." You could hear the father go to his room and open the door and then start to come down toward the parents room saying "If you are in my room there is going to be hell to pay !" Little Tony was frozen in place with a look of terror on his face." The father opened the door and stood staring uncomprehendingly at the little boy and said "What the hell !" Finally Tony tried to bolt out the door past the father who easily grabbed him saying "No wonder you don’t like football you little pansy." Then he dragged the little boy down stairs and yelled outside "Gladys, Get in here I have something to show you."
The little boy looked terrified. I still felt terrified 15 years latter. My mother and sister walked in the door. My mother looked down uncomprehendingly just as my father had. My sister who was a year and a half older said "Oh, How cute." And smiled at me then looked angry and said "YOU, Were in my room. I am going to kill you." My mother said "Tony, What are you doing in your sisters clothes ?" I could not answer. My father finally screamed "Get out of those clothes and get back her immediately." As I went up the stairs I could hear them talking about me. When I got back down my father was standing there waiting with the belt.
Santa chose that moment to stop the TV and said "So do you still think I have the wrong house ? Are you telling me you don’t like the dress ? You seemed to like dresses when you were little." Smiling again he winked at me.
Looking back at him I said "Yes it is beautiful." Looking at me mischievously Santa Said "So was that the last time you dressed as a girl ?" Looking at him shyly I said "You know it is not." Santa turned back to the TV and hit the remote. Appearing on the screen was a 15 year old version of my self this time over at my best friend Chad’s house it was still Christmas we were in his living room. Chad was showing me all the things he had gotten for Christmas. A bicycle, Short wave radio, Atari, The coolest jeans. I found myself attracted to the pile of stuff that his sister Sally had gotten. Chad noticed and said "What are you looking at her stuff for ?" I replied "Sally is a pretty girl and she must look awesome in that cute little dress." I picked up the little floral dress that was sitting on her pile of Christmas stuff and held it up in front of myself as if to model it. Chad looked at me and got a funny look in his eye’s and said "You like that dress don’t you ?" I had no idea what to say and just looked at him. Chad continued "Would you like to try it on ?" I still had no idea what to say this was unfamiliar territory. On one hand I wanted to wear that dress worse than anything. On the other hand I was afraid of what Chad would think and how he would react. After my dad’s reaction when I was 10 I had watched and come to realize that the world took a dim view of boys that wore girls clothes. Chad looked closer and said "Yes I think you do want to wear that dress, No one is home they won’t know." I looked down and realized that Chad was quite aroused by this. This aroused me and I lost some of my inhibitions. Chad took me by the hand and led me to his sisters room and said " Sally will not be home for hours why don’t you get dressed for me." Looking around I realized there was no turning back now. Going to the dresser I pulled out a pair of panties that matched the dress. I stripped off all my male clothes. Chad stood and watched me he was now fondling himself though his pants. I pulled the panties up around my now totally erect cock. Next I rummaged until I found the matching Bra. The cups were a little to big for me. I continued hunting until I found a slip. Pulling it over my head I could tell by the way Chad was reacting that he was just as turned on as I was. Next I dug in the closet finding a matching pair of shoes that almost fit. Finally I pulled the dress over my head and went over to the dresser and took a brush and combed out my long hair when I finished I turned around and Chad was staring at me in a way he had never looked at me before. He said "Tony, You look awesome !" I turned and looked in the mirror and could not believe the pretty girl I saw looking back. As I turned back to Chad he had moved closer and shocked me by grabbing me and kissing me on the lips. I backed away and Chad moved after me pinning me up against the wall. I could feel his erection pressing against me. He kissed me again reaching down he reached up under my skirt and grabbed my panty covered butt hard enough to leave bruises. I tried to push him away but he was insistent. Chad pulled me over to the bed and told me "Most of the girls I date suck my cock and you will be no exception." I replied "I am not a girl." Chad looked me up and down telling me "You look like a girl, In fact you look like the prettiest little girl that I have ever let suck my cock." Pushing me to my knees he undid his belt and dropped his pants. His cock was not that big but it was very hard. It was the first erect cock I had seen besides my own. I told him "I will not suck your cock !" Chad replied "If you don’t I will tell everyone in school that you dressed up like a girl and wanted to suck my cock but I would not let you." What could I do ? I moved toward him. I thought to myself that I did want to suck his cock but wished he had been nicer and more gentile about it. I reached up and grabbed hold of his cock and stroked it once. I felt his cock tighten and he came instantly I held his cock as he shot spurt after spurt of thick white semen all over the front of his sisters new dress. I looked up into his embarrassed face and he yelled at me "Take that dress off and get out of here !" I quickly dressed and left. Santa stopped the TV again and said "Your friend Chad was not very nice was he ?" I replied "No, he would not speak to me after that and when he did say something he would call me a fag." Santa said "Your fetish so far has only got you into trouble and you still want to do it ?" I sheepishly replied "Yes more than anything."
Santa again went into his bag this time he pulled out several smaller presents tossing them in my lap and said "Open these." Putting down the dress I unwrapped the first one finding the sexiest black lace and silk panties and bra I had ever seen. I could feel a stir in my groin as I thought of wearing the bra panties and dress. Santa smiled and said "You like them do you ?" I responded "You know I do." Santa said "Finish with the presents." As I unwrapped them I found a matching black garter belt, stockings, diamond earrings, some sexy black pumps a diamond necklace and a case full of makeup and a hair brush. Everything I unwrapped was just what I would have bought if I ever had the nerve to do so. Finally Santa said "Put them on." As he poured another shot of bourbon I picked them up and went to go to the bedroom when Santa said "Do it right here I want to watch." That smile of his convinced me so I stripped naked throwing my male clothes into a pile. My cock was now at full mast somehow I did not care that Santa saw. First I wrapped the silken bra about my chest. The cups were a little big but I figured I would get some fake breasts later. Next were the panties I just about creamed when the silken material touched my inflamed cock I then put the garter belt on. Santa sat there watching sipping his bourbon. It was obvious he was getting aroused. I sat down and pulled the stockings on one at a time thinking that I will need to shave my legs. Standing up Santa said "Very nice you already have a feminine shape about you." I felt very flattered as I picked up the dress and pulled it over my head the silken material was heaven. Santa asked "Move over here so I can zip you up." I obliged, his touch was magic he also ran his hands down my sides, I felt a funny tickling. I stuck one hand up and pirouetted for him. He said "Very nice, now take that brush and comb out your hair." I picked up the brush and walked over to the giant mirror next to the fireplace looking in the mirror I noticed how nicely the dress fitted but I still looked like a guy wearing a dress but I was feeling very turned on. I could still feel Santa’s magic touch tickling me throughout my chest area. I raised up the brush and combed through my short brown hair. In the mirror I watched as my hair sparkled where the brush had touched and it looked almost as though the brush was stretching and coloring my hair after one swipe I had a shoulder length blond strip running down the side of my head 10 minutes later I had a full head of shoulder length blond hair. I also brushed my eye brows and pulled my skirt up and brushed my pubic hair. When I looked all my chest hair had vanished. Looking back at Santa he said "Are you having fun? Do you still think I have the wrong house." I smiled and looked back in the mirror at the pretty girl starting to emerge and then smiled back at Santa and said "You definitely have the right place." He then said "I think a little makeup is in order." Walking over to get the makeup case I looked down and Santa was as turned on as I was and he was fondling himself through his pants. Walking back to the Mirror I took out the makeup not knowing where to start I took a tube labeled, Beard Hide and rubbed some into my chin as it went on the same sparkle happened as with the brush and it left my face smooth as a baby’s bottom. After doing my entire face I used some eye liner, blush and lipstick. Backing away from the mirror to get the full effect I saw a beautiful girl looking back Santa got up and brought the shoes to me that I put on the effect was complete I could not believe what I saw in the mirror. Santa stood beside me also looking in the mirror and said "Now how’s that for a Christmas present ?" I said "This is incredible." Santa smiled again and turned me to him holding my shoulders in his magic hands he said "And now for my favorite part." Looking me deep into me with those kind gentle and now passion filled eye’s a wave of lust like I had never experienced swept over me and I dropped to my knee’s and undid his belt pulling down his pants. I reached up caressing his erection through his red silk boxers pulling down the boxers I freed his 12 inch cock looking up Santa looked down at me smiled again and winked at me. Gripping his cock about the base I grabbed his balls with the other and licked the entire head before sucking the entire head into my mouth wrapping my tongue around his cock I started bobbing my head back and forth as I stroked the part that I could not get into my mouth I felt his cock grow even bigger as he grabbed the back of my head and drove his cock all the way down my throat. Strangely I felt no urge to gag he continued fucking my face while I held on to his balls suddenly he grunted as I felt his balls tighten and he said threw clenched teeth "Here comes the best present of all." He pulled out until only the head of his cock was in my mouth. I could feel as he pumped a massive load into my mouth I swallowed every drop. As soon as I could feel his nectar bounce off the back of my throat I could feel the magic sparkles work there way down my throat I felt the magic sparkles engulf my raging hardon spreading up to my chest finally engulfing my entire self in a wave of sexual ecstasy such as I have never felt before. Never once letting up on Santa’s erupting cock. Finally I had sucked everything Santa had to give and the wave of sexual orgasm that engulfed my entire being subsided. Pulling back I looked up and Santa was smiling down at me. Leaning forward I kissed the tip of his softening cock as he reached down and helped me to my feet. I felt strangely different as I looked into the mirror. The first thing I noticed was that I now had two nicely shaped breasts poking enticingly out from my chest as I looked down I noticed there was no hair under the sheer stockings on my legs. Santa watched as I finally felt the strangeness and reached down to grab my cock only to find that it was gone. Pulling up my skirt I could see the outline of a pussy under the silky panties reaching down I felt the new parts with a feeling of awe. Dropping the skirt I turned to Santa who said "Good little boys eventually get what they deserve." Pulling up his pants Santa walked back to his bag and pulled out one last present and said "Open it." Opening the present I found a purse that matched my new dress opening the purse I found a drivers license, a new birth certificate and a social security card and all my credit cards that said "Susan Bryant" hearing a noise I turned to Santa who was heading to the fireplace He stopped and said "On to my next special case, Merry Christmas and A happy New Life." As he turned and went up the chimney.
If you liked or didn't like this story this story Email me at SONOFAK@AOL.COM and let me know. The only way I can get better at writing these stories is if you let me know what you like or don't like or maybe would have done differently Or which parts really turned you on. Thank you for reading my story Karen Flynn.
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