CHRIS'S SURPRIZE PRIZE 01

Chris’s Surprise Prize

Chris’s Surprise Prize Part 1


My name is Christopher James who is 22 years old. I am called Chris. I am a closet cross-dresser. I live on my own in an apartment in Los Angeles and work at a bank. I bought my clothes by mail-order not having the courage to buy things in person. I just loved the feel of the soft silky women’s clothes on my skin. I often wore panties and pantyhose under my suit to work. I had several nightgowns which I always wore to bed. In fact I rarely wore male sleepwear. While I was growing up I used to wear my mother’s clothes.

I had entered a completion in a magazine called “Blush”. The first prize was an automobile which would be great as my own was old and giving lots of problems. The other prizes were surprise prizes. They just gave the value of the prizes. The 2nd prize was worth $30, 000, while the other prizes were lesser amounts.

I had just got home from work and entering the foyer of the apartment building from the underground garage I went to my post box. I collected my post and noted amongst the envelopes was one from “Blush”. It was after the closing date of the competition. I went into the lift and heard someone calling for me to hold the lift. It was a woman who lived on the same floor as me. Her name was Patricia and I fancied her but not had the courage to ask her out on a date and also because of an incident. The building had a basement Laundromat. I had on occasion washed my women’s clothes there. There was one occasion when Patricia had surprised me when I was taking some of my delicates out of the drier. She had looked at me quizzically but did not say anything.

Patricia was wearing a sheer blouse and her lacy bra was visible. I caught myself staring at her bra rather than its contents. She noticed and smiled and said, “Chris are you looking at my melons?” I averted my eyes to look into her eyes. I was short for a guy and Patricia was taller than me. I felt my face get hot as I blushed. Patricia continues to tease me and said, “Or is it my bra you were looking at?” I blushed even more. I stammered, “S... sorry it’s your m... melons I was looking at.”

Patricia said, “You can’t fool me, I know it’s my bra you were looking at.” I just stayed silent the rest of the ride in the elevator. We reached our floor and then exited the lift. Being a gentleman I let Patricia go first. I walked behind her and looked at her back my eyes focused on her bra straps. I remembered from school I loved looking at the girl’s bra straps as I sat behind them in class.

Chris’s Surprise Prize Part 2


We reached my apartment first and I stopped to get my keys out. Patricia turned around and waved at me and I returned her wave. I unlocked my door and went inside. The first thing I did was after putting my briefcase down was open the letter from “Blush”. I began to read the contents and my mouth dropped open in surprise when I read that that I had won the 2nd second prize. I turned to the second page and discovered what I had won was a voucher from a bridal store to the value of $30, 000. The voucher was not exchangeable for cash and had to be used within a month. I was stunned I had won something of great value yet to get it I would have to go to a bridal shop and present the voucher. I was apprehensive of doing it.

The next day was Saturday and I decided to go to the shop called “Cinderella’s” just to check the place out. I loved walking in malls and secretly looking at women’s clothes. But for now I was just going to relax with a DVD and also surf the internet while dressed of course. I made myself a cup of coffee and relaxed while sitting my couch. I read the letter from “Blush” again. I had always wanted to wear a wedding dress with lots of petticoats. I now had a chance. I just had to muster up enough courage to go into the shop. I went to my bedroom which looked like a normal young guy’s room. I kept my female clothes with my male clothes. I began to undress, removing my outer male wear. I had panties and pantyhose on.

I just added a silk lacy camisole and a half slip to what I was wearing. I put on a white silk blouse and a red skirt. I just loved the cool feeling of the slip on my stockinged legs. I had small feet and was able to wear ladies shoes so put on a pair of white low heeled sandals. I did not shave my leg and body hair so the effect was not that good. I did not have the nerve to do that. I wore my hair on my shoulders and for work wore it in a ponytail. At home I wore it loose. I undid it and brushed it out. I would love for someone to style it for me. I kept my finger and toenails neatly trimmed and shaped. I would often paint my fingernails.

I went to the kitchen and began to prepare my supper. I was a fairly good cook and loved to make my own meals. Tonight I was doing my favorite, macaroni cheese. I had the TV on and was watching soaps. I had a glass of wine as I cooked. I had everything done by the time “The Bold and the Beautiful” started.

After my meal I went to my bedroom to fetch some nail polish which I used to paint my nails as I watched the TV news. After that I went to my room and while standing in the bathroom I got a tube of lipstick from the cabinet and applied it to my lips. I always coated it thickly. Back in my lounge I poured myself another glass of wine and put in a DVD. It was about cross-dressing and portraying yourself as a female. I knew it would be a long time before I venture outdoors while dressed.

As I watched I sipped my wine and was delighted when I left a trace of lipstick on the glass. After the DVD I put on a Star Trek Voyager DVD. This was my other passion, sci-fi movies. Later on I got ready for bed. It was nice to undress and then put on my nightgown, which was a long pink cerise creation. It had a matching gown. I kept my panties, pantyhose and slip on. I got into bed after doing my teeth and reveled at the soft silky material on my skin. I surfed the internet for a while looking at sissy outfits. I fell asleep wondering about my visit to the bridal shop the next day.

I woke the next morning and as was my custom upon waking I began to stroke myself after I lifted myself up and pulled my panties down. I gripped my tool with my nightgown. My tool was normally hard this time of the morning being excited by the soft silky material of the nightgown. I wanted to prolong my excitement so I stroked myself slowly. I began to build up in excitement till I reached the point of no return and I erupted into my nightgown.

Chris’s Surprise Prize Part 3


I lay and relaxed for a while and then got up and put on a clean nightgown and a pink quilted gown and went to make myself breakfast. Really had a proper breakfast during the week and enjoyed a full breakfast on the weekends. I finished eating and then went to the bathroom and where I had a long leisurely bubble bath.
I got out the bath and dried myself off with one of my soft fluffy pink towels. I stood in front of the mirror and shaved while standing in the nude. This was a task I hated but an unshaved face looked really terrible. I powdered myself with baby powder. It had no smell. I went to my room and began to dress. I put a pink panty which had ruffles across the seat. Next I put on some thigh high stockings which had elasticized top to hold the up. I did not want to wear my garter belt in case they were seen under my pants.
I put on one of my silk shirts after spraying myself with deodorant. I loved silky clothes, it looked masculine. Next I put on a pair of slacks and then my socks and shoes. I brushed my teeth and then left the apartment.
As I walked along the corridor became aware of someone walking behind me and turned around and saw it was Patricia. I said hello and she greeted me also. I got to the elevator and held it for Patricia. We began to ride down to the foyer. During the ride down other people got in the elevator and soon it was full. Amongst the passengers was another girl Kathy who lived on a lower floor and was friends with Patricia. I ended up standing close to Patricia with my rear pressed against her.

We got to the foyer. Kathy quickly moved forward and quickly closed the doors and pushed a few buttons. The elevator started going up. I asked her what she was doing. She did not reply but Patricia asked, ”Chris are you wearing panties? , don’t deny it I could feel them while you were pressed close to me. “ I blushed and said,” No I’m not “, blushing further. She replied and said, ”Why are blushing then? “.

Chris’s Surprise Prize Part 4

Patricia then pressed the emergency stop causing the elevator to stop between two floors. I did not know what to say and wondered if I was going to be discovered. Patricia goaded me further and said, ”If you weren’t wearing panties you would not been blushing and besides I know you live alone and I saw panties in your wash, come on ‘fess up. “
Before I knew what was happening Kathy got behind me and held me with my arms behind my back. Kathy was also taller than me. Patricia said, ”Well we’ll just have to look for ourselves. “Before I knew what was happening Patricia began to undo my belt buckle. I began to protest but Kathy said, ”Shh, sissy boy we don’t want to hurt you.” Patricia had my belt buckle undone and then unclipped my pants. I was just frozen and let them have their way with me. I was embarrassed and excited at the same time.
Kathy said, ”Patricia our sissy boy is not even putting up a fight.” Patricia replied, ”Yes seems he is scared of us.” Patricia then addressed me and said, ”OK let us see what you are wearing.” I was helpless to stop Patricia and she gripped the puller of my zipper and began to pull it down. She soon had it down and opened up my pants and pulled them down exposing my panty. Patricia exclaimed,” Well will you look at that! “ Kathy used her free hand and they together pulled my pants down to my knees. My thigh high stockings also came into view. Patricia said, ”He’s wearing stockings too. “ My pants were allowed to fall to the floor effectively hobbling me.
The girls began to rub their hands over my panty and stockings. This caused my tool to harden and this did not go unnoticed. Patricia said, ”Oooh looks like sissy likes that, his tool is getting hard. “ Patricia reached down and pulled my panty down exposing my now hard erect tool and then just as quickly she pulled my panty back up. My pants were pulled up too and my zipper was pulled up and my pants clipped and my belt was buckled. Kathy pushed the emergency stop and the elevator resumed its journey. Patricia said, ”We know your secret now Chrissy, I think it’s actually cute, a man getting in touch with his feminine side. “
We got to the next floor and luckily there was no one to take the elevator. Patricia pushed the foyer button and the elevator started on its downward journey. We reached the foyer and the girls exited the elevator and I followed them down to the underground garage. I went to my Ford Pinto. Kathy drove a Ford Mustang while Patricia drove a Buick. Kathy said, ”Look Chrissy drives a little automobile. “
Patricia called out to me saying, ”Are you going to buy some panties today, Chrissy? “ Luckily there was no one to overhear what she asked. I got inside my automobile and drove off, the girls had already left. I contemplated the fact my secret was now out. There was nothing I could do about it now. I vowed not to wear my feminine clothes again while going out of my apartment. I would wear them this time.
I headed over to where Cinderella’s was located. I arrived there and went just past it and circled the block and parked in the lot across the street. I went into one of the stores and bought some wine. I walked back to my Pinto and placed my purchase in it and then took a walk past Cinderella’s. They had the most beautiful gowns in the window. I still did not have the courage to go in just yet. I decided the best time would to go into the store when it was near closing time and there were no other customers. I still wanted to do it today and noted their hours. They were due to close at 12 noon. I had about an hour to kill.
I went back to where my Pinto was parked and went and bought a newspaper, a soda and a pie. I drove to a nearby park and relaxed and strategized as to what I would say. I had my pie and soda while sitting on a bench in the park. I would spin them a story saying it was for me and wanted to wear it to a fancy dress party. I left and then drove back to Cinderella’s and this time parked my Pinto in the small parking lot next to the building. It was 10 minutes before the hour.
I had the letter from “Blush“ with me and I went into the boutique. A woman of about 40 approached me and said, “Yes can I help you, you do realize we are due to close soon?” I said, ”Yes I know and I have come about this letter I received from “Blush” magazine. I produced the letter and gave it to the woman. She read it and asked if I had proof I was the person mentioned in the letter. I got my driver’s license from my wallet.
She said,” It seems to be in order, now who is the dress for, do you have a sister or girlfriend or fiancée?” I took a deep breath and said, ”Actually I have none of those and the dress is for me, I wish to wear it to a fancy dress party.”

Chris’s Surprise Prize Part 5

The woman was wearing a blouse and her bra was visible, as usual I was more interested in the bra than the contents. She said, ”I am Beverly Guthrie, I am pleased to make your acquaintance Christopher. What can l call you? “ I looked up into her eyes as I began to speak, “I am called Chris” .”Pleased to meet you Chris, I never would have thought it would be a man claiming this prize, OK I wonder how we are going to accommodate you, and it will have to be after hours as my regular clients may not like the idea. “ Beverly went to the front door of her shop and locked the door and turned the open/closed sign around.

I said, ”I must say you are accepting of this, I was a bit apprehensive of walking into a female domain. “ Beverly replied, ”I am curious, why would you as a man want to wear woman’s clothes, are you one of those cross-dressers? “ I replied blushing, ”I am and only do it in my apartment. “ Beverly asked, ”Are you wearing anything now? “ I replied and blushed further, ”Yes, I am wearing panties and stockings. “

Beverly, ”Don’t blush so much, I thinks it’s sweet a man like to wear women’s clothes after all women wear men’s things. “ I said, ”Yes but it’s not acceptable for guys to wear women’s clothes in public. “ Beverly said, ”Anyway let’s see what we can to for you to get your prize. “ Beverly took my hand and led to the rear of the shop. There were the most beautiful frilly gowns on display and I noted that most of them had sleeves and full necklines, not like some gowns that were strapless. We went through a door marked, ”Fitting room. “ Beverly closed the door behind is and said, ”Ok, Chris the first step is for you to be measured so that I can select the right size, I can even involve a dressmaker to make something custom fitting for you, don’t worry she is discrete.“, when she saw the look of apprehension on my face.

”OK the first thing for you to do is undress so I can measure you. “ I took off my shirt and then began to unbuckle my belt. I thought of the incident in the elevator a few hours before when I was exposed and now I was removing my clothes in front of a woman. I unclipped my pants and pulled my zipper down. I slipped out of my shoes and pulled my pants down and stepped out of them. I was standing in my panty, stockings and socks. Beverly said, ”And where did you buy your lingerie? “ I told all my clothes were bought by mail order. Beverly began to measure me and while she did so we talked.

Beverly said, ”Your panties are so pretty and feminine, what do you like about wearing them, and what else do you have in your drawers? “ I said, “The soft silky feel is nice and I have mostly lingerie, I have nightgowns, camisoles, slips, a few skirts and blouses, I have some shoes. “ My tool was getting hard at the talk of lingerie. ”And have you ever been outside while dressed up? “ ”No, I have not had the nerve to do so. “ .”Well, I don’t know if you are aware of this but one of the conditions of your prize is to wear your dress in public and ”Blush “ magazine is to take photos of the bride in her dress in an actual wedding ceremony, it’s one of those conditions that comes with the prize, so you have a little problem. “ I also began to blush when I realized my hardness was noticed by Beverly. She said, ”This excites you, does it?” I just nodded my head.

”I did not know that, but my desire to wear a wedding dress is so overwhelming, if I could just look like a woman I think I could pull it off. “ ”Well for a start I can see you still have lots of body hair and that will not do, I will help you to get a feminine body so you can wear the dress properly, for example you will need cleavage, a bigger butt, smaller waist, you have long hair which is good, your facial features are not exactly masculine, yes it think you could pull it off. “ My tool hardened further and began cause a bulge.

I said, ”That would be great, how would we do that? “ .”Haven’t you thought about it, investigated looking like a women or anything? “ .”No I haven’t. “ .”I’m surprised you haven’t, anyway that the last measurement. “, and wrote down a figure on a pad. ”Get dressed and lets go to my office and we can talk. “

I began to dress while Beverly left the room and soon I was dressed again. I joined her in her office. My tool had subsided and Beverly had a glasses of wine for us and said, ”We must drink a toast in celebration of your winning this opportunity to wear a dress. “ She handed me one and we clinked glasses and then took our seats. We sat on the same sofa in the office.

Chris’s Surprise Prize Part 6

Beverly suddenly leant to me and kissed me on the lips. I was quite surprised. She said, ”OK now tell me what kind of dress you would like. “ ”Well anything frilly and feminine and it must have lots of stiff petticoats underneath. I would like something that covers my shoulders, a sweetheart neckline with high illusion. It must have puff sleeves. “ My tool began to get hard due to the talk of feminine clothes. ”Ooh it sounds like you have a good idea of what you want, the other thing we must do it get you a female looking body, there are way of doing it like breast forms for your cleavage, we can use a waist chincer and also pad your hips. We have to do that first before trying to fit a dress on you and of course I will have to measure you again, I’m sure you won’t mind as you enjoyed it so much .“ ”Well whatever it takes to get me into a beautiful dress is fine with me. “ ”Yes you and I will have a lot of fun turning you into a woman. “

”Ok how do we go about this? “ Beverly replied, ”Well let’s look on the Internet, we need to find you things, breast forms, hip padding and something to give you a smaller waist. “ Beverly got up and went to her computer and said, ”Join me, we can look together. “ I got up and pulled up another chair. Beverly soon found a site for cross dressers which detailed all you would need to become a woman. I loved the idea, I would get melons and a female curves. You could order what you required. Beverly began to do that and said she would cover the costs.

I thanked her for that. Beverly said we would have to wait for the items to come and then we could begin to fit dresses. Beverly suggested I should remove the hair from my body and recommended a few products. Beverly asked if I would like to try a few things on. I said I would love to and we went back to the fitting room where I got undressed again down to my stockings and panties. Beverly came back into the room with some items. One was a bra and Beverly helped me onto it. I loved it when she strapped me into the feminine garment, I liked the compression on my body. She suggested I remove my stockings and use them to fill the cups of the bra. I did so and handed them to her. Beverly rolled them up and placed them the cups. Beverly came out with an item I did not have in my collection, a suspender belt.
She strapped me into the belt and then told me to sit down on a chair. She produced some stockings. She looked at my legs and said,” This hair will have to go. “ She began to roll the first stocking up my leg and then the other. She pulled me to my feet and clipped the tabs to my suspender straps. She helped me into a camisole. She left the room and I admired myself in the bra, suspender belt and stockings and camisole. I stood sideways and liked the view of my stocking filled bra. Beverly came back into the room and she had a number of petticoats with her. She helped me into the first which was satin trimmed with lace on the hem. The next was a stiff net of tulle and was followed by another of organza. The effect was that I was dressed in petticoats that stood out from my body. I swayed and heard the petticoats rustling.
Beverly said, ”Isn’t that the most wonderful sound? “ ”It sure is, I just love to be dressed all femininely like this. “ ”And you look so cute let me go get a dress for you to try, while you enjoy your swishing petticoats. “ Beverly left the room and I was actually glad to wear the flared petticoats as my tool was getting hard and bulging in my panties.

Chris’s Surprise Prize Part 7

I enjoyed myself by gripping the petticoats and swishing around the room. The room was larger than the normal fitting room, just as well as the petticoat skirts flared out so much. After a while Beverly came back into the room unnoticed by me. She spoke, “Ooh Chrissy looks like you are enjoying yourself.” Her referral of me by the feminine name caused me to blush. She said, “Don’t blush the name suits you, I mean I can hardly call you Chris while you are dressed so femininely.” I said, “Ooh yes I like the name.”

I knew that I could trust Beverly to help me in my quest to dress while outdoors and come out of the closet. Beverly was carrying a dress. It was plain looking and she said, “Come let’s get you into this one it’s a bit plain.” Beverly started to unbutton the dress and then told me to bend forward with my arms outstretched and then slipped the dress over my head and arms. I pushed my arms through the sleeves and Beverly got the dress on me. I stood up straight and then Beverly pulled the dress down over the petticoats and went round to my back and began to button up the dress. Beverly said, “It’s not a perfect fit as you don’t have the perfect female body but it will give us a good idea of how you will look.” Beverly left me again and I just enjoyed moving around in the dress and loved feeling all feminine. Beverly returned once again and she had a veil and headdress with her. She loosened my hair and began to brush it out. She then fixed the veil and headdress to my head with clips and finished off by pulling the veil over my face. I looked my refection in the mirror and loved what I saw.

Beverly left the room again and moved around walking forward and enjoyed the feeling of the pull of the train on the floor. I looked back to see the dress spread out behind me. Beverly came into the room with a camera and asked if it was ok to take photos of me, she said I could take them home with me and she would not keep them. I agreed and she began taking several shots of me in various poses. It so wonderful having someone with empathy towards me cater to my needs and I was even more determined to come out the closet, although it was going to be inevitable due to the requirements of my prize.

Beverly finished the photographs and said, “Come Chrissy you will have to get undressed now, I know how much you have enjoyed this but I will have to go now.” I was sorry for it to end Beverly began to remove the veil and headdress and then unbuttoned the dress and helped me out if it. The petticoats were also removed, followed by the bra, suspender belt and stockings. I was left standing in my in my panty. I sat on a stool and pulled my stocking on and then my socks. I reluctantly began to dress in my men’s clothes. Beverly left the room and said I should meet her in the office. I did so and Beverly was busy on her computer busy putting the photos on a disk. I noted there was a few video clips as well. She handed me the disk and then kissed me and I responded by kissing her back. She saw me to the door and unlocked it and I left to go to my Pinto. I drove towards home.

I stopped at a food store and got some groceries and then continued on my way to my apartment. I went from the underground garage to the foyer and to the elevator. There was no one about and I rode up in the elevator thinking of my experiences of the day so far. I exited the elevator and then began to walk to my apartment. As luck would have it Patricia exited her apartment with Kathy and the two of them walked towards me. They got up to me and Kathy said, “Well Chris did you have a lovely day buying panties, did you maybe get something else like nighties too.” I blushed and said, “I don’t buy my things in shops I order them online.” Patricia said, “Why are you a little shy, maybe we should take you shopping some time.”

As my hands were laden with bags the ladies took their opportunity to rub the hands over my rear and Patricia said, “You still wore your panty in spite of us having exposed you, does it give you a thrill to wear a panty under your pants or what?” I just said nothing and blushed. Kathy said, “Of course he likes it.” They both kissed me on the lips and said, “Goodbye pansy.” I continued on my way to my apartment and set down my bags and got my key out and entered my apartment.

I closed the door behind me and set down my bags and went to my refrigerator and got a soda and then relaxed on my couch. Remembering the disk Beverly made for me I went to my computer and put the disc in and then began looking at the photos and video clips of myself in the wedding dress. I could see what Beverly meant about the fit of the dress. I relaxed the rest of the afternoon in my apartment. I was due to meet my mom, who also did not know of my cross-dressing; at least I didn’t think so. I was due to have dinner with mom and go see a movie.

My father had died two years previously. I enjoyed the company of mom and it was she who encouraged me to get my own apartment. I welcomed it as it was a chance to dress without the fear of been discovered. Well now I had been found out. I did my own laundry as I wanted to be independent. I began to get ready. I undressed and quickly showered. I noted that my panties had a damp spot from being excited as I had been hard most of the afternoon.
I dressed again and wore a pink panty and stockings and dared to put on a camisole as well. I wore a thick shirt to hide it. I left the apartment and drove over to mom’s house. On my arrival mom kissed me and said, ”Welcome my boy, so nice of you to visit me.” We sat down to eat and as always I enjoyed mom’s cooking, she had taught me a lot of what I knew in terms of cooking. We finished our meal and left to go to the movie house. We drove there in mom’s Cadillac with mom driving us.

We went to a mall where the movie house was located and on the way there we passed a bridal shop. I was looking at the display a bit too intently and mom said, “Those are pretty romantic dresses aren’t they Chris.” I just said, ”They sure are.” We carried on and got to the movie house and bought tickets and settled down to watch the movie after buying popcorn and sodas. We enjoyed the movie and then went back to mom’s house. I kissed mom goodbye and then got my Pinto from the garage and then left to go to my apartment.
Back home I quickly got my male clothes off and got my new pink negligee on and got a glass of wine and got into bed. I thought of the day’s event and was soon hard and excited. I needed some relief and pulled my panty down and began to rub myself with my negligee. I soon came in it. I went off to sleep and dreamt of being a woman.


Chris’s Surprise Prize Part 8

Two weeks passed and I got a call from Beverly, she invited me to come over to her store as she had something for me. I was to come again on the Saturday at closing time. I had also bought the hair removal product Beverly had suggested and had used it. I even used it on my face and I was enjoying the need not to shave. I spent the morning in a leisurely way and left to go “Cinderella’s”.

I arrived on closing time and parked the Pinto next to the building. I went to the entrance and saw Beverly coming to the door. She opened the door and then come out of her store and told me I should come with her, we were going to her house just to the rear of her store. She said it would be more private there.

I walked with her to her house and waited while she unlocked her door. We went inside and I noticed how feminine everything was. Beverly had told during the walk over to her house she had everything in her house for me. Beverly told to sit down and make myself at home while she went and got us drinks. Beverly gave me my glass of champagne and we talked and then Beverly asked me to undress so we could start. I welcomed it as I was keen to start dressing. I removed my shirt to reveal a pink satin and lace camisole underneath. I removed my pants to reveal my panties and stockings which were held up by a suspender belt. Beverly said, “Don’t you look so pretty in your lingerie, but everything excepting your panties will have to come off too.”

I began to remove the rest of my clothes. Soon I was standing before Beverly in only my panties. She said, “Oooh yes that it much better, you are smooth just like a little girl. I blushed at what she said. Beverly suggested we go to her bedroom. We went through and Beverly kissed me. She told me to lie down on her bed. I complied and she placed a blindfold over my eyes. I could hear her moving about and I felt a weight over my left side followed by a weight on my right side. Beverly warned me to stay still. After a while I was allowed to sit up and immediately noticed the feeling of weight hanging from my chest. I knew these had to be melons. Beverly asked me to lift my hips and I felt her remove my panties, my tool which was hard at this point and sprang up to attention.

She pulled another garment on to my lower body and told me to stand up. I ran my hands over my hips and buttocks and discovered they were padded. I felt Beverly strap a garment around my waist and I felt the constriction of it. Next I felt Beverly place a garment on my chest and get my arms through straps; I knew this was a bra. She pressed against me and fastened the back straps and lifted my forms into the cups. I felt the support of the bra on my forms.

Next I felt Beverly place something at my feet, she guided my feet into openings and I felt her tug the garment up my legs. She removed the blindfold and I looked at myself with awe in the mirror. I had a female form, my melons perfectly proportioned to my frame and I had female rear curves too. I said, “I look so good.” Beverly said, “Yes it has worked out well.” Beverly began to talk to me asking me about my life what did for a living. I told her and then she came out with a bombshell. She asked me if I would consider leaving my job and come and live with her. She would support me. The idea of being near a shop with frilly dresses and lingerie was appealing.

Chris’s Surprise Prize Part 9

I told Beverly it was a good idea and it she didn’t mind I would love to live with her. She asked how soon I could do it. I told her I would have to resign first. I had to give a months’ notice and I also had to give a months’ notice at my apartment. She said I could move in with her immediately if I liked. She said she would love to help me come fully out of the closet. I said I appreciated that.
Beverly continued to dress me; she suggested I spend the night. I said I would love to. Beverly asked where my vehicle was parked and asked me for the keys and said she would move it into her garage. I did so and while Beverly was gone I took the opportunity to examine closely what she had put me in. Beverly was not gone long and returned to her house. She said, “Ok Chrissy now what I want you to send an e-mail resigning from your job at the bank. I want to get on with this as soon as possible. Do you have a private e-mail account?” “I do have one”
We went to her computer and I logged on and sent an e-mail to my boss. I was going to do anything that Beverly suggested to be able to wear women’s clothes. I looked in the closet and found the petticoats I had worn before. I put them on and had by prancing around and letting them swish. Beverly came back into room and approved of what I had done. She had a satin dress for me to wear. She helped me into it and then loosened my hair and brushed it out.
She got me to sit at her vanity where she did my makeup. When she allowed me look it in the mirror I was amazed the result. There was no trace of maleness. Beverly suggested we go out to eat as I was dressed now. I hesitated and she said come on this is what you wanted to do. I agreed and Beverly added some finishing touches, some jewellery and a small dainty watch. She put some clip on earrings on my lobes. She sorted out a purse for me and put a number of items in it for me, tissues, lipstick, a wallet and some tampons. She helped me into some shoes and then we left the house.

Chris’s Surprise Prize Part 10

We walked to her garage and I enjoyed walking in a skirt outdoors. I loved the coolness of the wind blowing around my legs. I got into Beverly’s Cadillac carefully after first smoothing my skirt down behind me and sitting first on the seat and then swinging my legs in. Beverly complimented me on that. We left and then drove along to a restaurant. We went inside and where shown to a table. As luck would have it I spotted Patricia and Kathy sitting at a table.
I froze for a second and then recovered. We sat a table past them and once we were seated I whispered to Beverly that I knew the two and told of what they had done to me. Beverly said I shouldn’t worry as it seemed they did not recognize me. We ordered with Beverly doing all the talking. We enjoyed our meal and during the evening the inevitable trip to the ladies became necessary. Beverly went with me and I went into one of the stalls and while I was busy I heard the voices of Patricia and Kathy. They were talking about me and what they did to me and were speculating about me. They also talked about when Beverly and I walked past them. The fact this girl had the same color hair as what I did, I was the same height and that if they imagined me as a girl that’s the way I would look.
I had my panties down and was sitting on the seat and doing a wee. Later I finished and got up and got my panties back up. Fortunately Beverly had put the suspender straps under my panties. I knew I would have to come out the stall and face the two. This would be a test. I exited the stall and Beverly was at the wash basin redoing her lipstick. I knew I had to act normally as a woman would.
The others were not yet out and I went and stood to Beverly’s right. I began to get my lipstick out my purse and apply touch up my lips. Patricia and Kathy came out the stalls and went to the remaining two places. They greeted Beverly and I. We greeted them and Patricia came over to me and asked if she knew me from somewhere as I looked familiar. I hesitated in answering and she exposed me by saying, ”Hi Chrissy, I mean Chris. I know it’s you. You finally took the courage and are out the closet. “ Kathy said, ”But I see you have had some help, introduce us to your friend. “ I did so and Kathy and Patricia said I looked good as a woman.

We returned to our table and Beverly told me I had done well so far and that it was good to get a compliment from my former tormentors. We finished our meal and then went to see a movie. Beverly got me to buy the tickets as she said it would be a good experience for me. I did so and spoke in a low soft voice. We enjoyed the movie; it was my favorite topic Sci-Fi about a trip into space.


Chris’s Surprise Prize Part 11

We left to go back to Beverly’s house and my new home to be. Once we got there we soon got ready for bed. Beverly had a long pink satin nightgown for me to wear. Beverly helped me to undress. Once my clothes were off my tool which was hard sprang to attention. Beverly asked if I been excited all day. I said yes pretty much. Beverly then asked, ”Well are you needing some relief? “ I said that I normally would stroke myself. Beverly then surprised me by saying, ”Well that not much fun let me do it for you. “ She left me and warned me not to do anything and then came back a short while later dressed in a low cut French maid’s dress.

Chris’s Surprise Prize Part 12

This caused my tool to rise even further and Beverly came and knelt before me and took my tool into her mouth and began to suck on it. I was quickly approaching a climax. I wanted it to last but the sight of Beverly’s deep cleavage before me and the fact she was so expertly sucking on my tool I could not help but come in an earth shattering explosion.
Beverly had swallowed all I gave her and she wiped the last drops from my tool and then helped me into the matching panties of my nightwear. She took the nightgown and slipped it over my head and then let it drift down over my smooth hairless body. I just loved it to have a woman dress me in this way. She escorted me to the bathroom where she produced a tooth brush for me to use. I brushed my teeth and then went back to the room.

Beverly came in a while later dressed in an identical nightgown. She asked if I wanted something to drink and recommended a nice warm glass of milk. I said that was fine. She left to go and fetch it. While she was gone I contemplated the day’s events. Beverly returned and gave me the glass and gave me a pill saying it was a vitamin pill. She kissed me goodnight and left to go to her own room. I soon fell asleep.

Chris’s Surprise Prize Part 13


I woke the next morning, it was Sunday and I did not have anything planned for the day. It was strange waking up to feel the weight on my chest. I had sleep on my side or back and not on my front like I normally did. I was aware of Beverly moving around. She popped her head into my room and asked if I was ready for some breakfast. I told her yes and then got out of bed and put on a gown and went to the kitchen. Beverly was busy making toast and frying bacon and eggs and told me to help myself to some cereal and juice which I did. Awhile later I had the rest of my breakfast. Beverly said we could go out later for lunch.

After breakfast Beverly said it was time for me to learn about some feminine things. I told her what I normally did. She asked how often I would do make up and my nails and seeing we were going to go out she suggested I bathe and then dress. I did so and I ran water and then Beverly came into the bathroom and added bath oils and bubble bath. She told me to relax and let the water and oils soften my skin. Beverly came back into the bathroom and proceeded to bathe me which I enjoyed immensely. It gave me hardness in my tool as usual. I was helped out the bath and Beverly dried me off and told me to start with my underwear while she bathed. I left the room with the towel wrapped around me. I began to dress putting on the padded panty and then my brassiere. Next I put on the suspender belt and then rolled on my stockings and clipped them in place. Beverly came out the bathroom and into my room and helped me with the waist cincher and then helped me into a slip.
She suggested she teach me about eye makeup. She began to put a foundation on my face and told me to carry on applying it. I was able to do. Beverly asked about my ability to do this and I told her I had got DVD’s on the subject and would they some things myself. Next was a blusher. Beverly did one side of my face and I tried to match it on the other side. I battled a bit but eventually it got it right. Next we worked on my eyes, Beverly said this was a bit tricky but all women did it so I should learn too. I was willing to learn too. I had a lot to learn about skin color and the appropriate makeup for different times of day. We started with applying eyeliner. Next was my eye shadow by coating my eyelids from the lashes to brows. Next a darker shade was used on my eyelid creases and then the medium shade was applied from my eyelashes to the crease on the outside half of the upper eyelid. My eyeliner was retouched and then mascara was applied to my eyelashes.

Chris’s Surprise Prize Part 14

I carried on with my lips using a lipstick pencil to outline my lips and then coated my lips with pale pink lipstick. I brushed out my hair and Beverly helped me into my dress for the day. It was a red satin dress that had a low neckline. I did my own nails and then we relaxed the rest of the morning. We left to go eat out and Beverly said we were to be joined by a friend of hers. Beverly assured me that it would be ok after I appeared a bit apprehensive.

We left for the restaurant and upon our arrival we were shown to a table where a lady was already sitting. She had her back to us and when we moved forward to take our seats opposite her I got the surprise of my life. It was my mom. I was taken aback and mom greeted me saying, ”Hello Chrissy how nice to see you. “

I stammered and said, ”M.. mom what are you doing here? “ Mom replied, ”You silly girl I’m just going to have lunch with my daughter and my friend. “

The waiter pulled out chairs for us and we sat down. Mom began to explain that she knew of my wearing her clothes while I lived at home. Beverly and mom were old friends from school and had met again after a long time. We ordered and had our meal after which we returned to mom’s house.
Mom knew all about my prize and said she was going to help me fulfill all the conditions.

Chris’s Surprise Prize Part 15

Mom and Beverly both kissed me. The doorbell rang and Mom went to answer it. Mom came back with a guy of about 23. Mom introduced us, he was Kevin and Mom said he was there to take me on a date. He knew I was really a guy and did not mind as he was bi. We relaxed and talked for a while and got to know each other. I was to go back to Beverly’s and then he would come and pick me up.

We left to go to Beverly’s after Kevin left. Mom came with as well as she said she was there to get her girl ready for her date. I had a quick shower and then Mom and Beverly did my makeup for me and I noted of the night time colors they used. I was dressed by Mom and Beverly.
I wore a pink and white gingham dress with two full petticoats. Underneath I wore a suspender belt and stockings and wore sandals with 2 inch heels. I wore a ribbon in my hair. The ends of the ribbon were tied under my hair. I felt all girly. Kevin arrived to fetch me. He drove a 60’s Ford Mustang. We went to restaurant near to where I lived.