My first dress  

19 posts
1/6/2006 11:19 pm

Last Read:
4/4/2007 2:35 am

My first dress

My first
Dedra Post
This is one of my short stories about my life as a cross dresser.

Chapter One

The beginning

I had just turned 8 when Linda came to work for us as a live-in sitter/housekeeper, mom had put a advertisement in the help wanted section, Linda was the only one that would work for the salary mom could afford. She had just moved away from home in Washington state.
She had lived with her father and four brothers and had the home maker for them since her mother died when she was fourteen. She hated them, her father worked in the lumber yard and was drunk most of the time, her two older brothers were no help to her around the house.
The two younger brothers were a pain in the ass, and constantly messing up the house which she was to take care of. She was a war with them all, so as soon as she turned eighteen she left home never to look back and to never let a male have control of her again.
Mom had divorced my Dad a few mouths earlier and mom and I had moved into my grandmother’s apartment building. My mom was the Manager of the building because my grandmother traveled a lot on business, my job was to keep the parking lot swept up, take the trash cans to the curb and keep the laundry room clean.
Linda had been working for mom little over a week, when mom asked her if she wanted to make extra money clean out an apartment unit that the family had skipped out owning rent. The mother and daughter left almost everything they owned behind.
Linda had finished cleaning the unit, and had kept all the clothes in large trash bags. I had finished cleaning the laundry room and was thirsty, I went into our apartment were Linda was going though the bags, sorting them. I asked her, “can I get a soda” she snapped at me “get your soda and go to your room” not knowing what I had done.


I did as I was told, not seeing that side of Linda before, she had never raised her voice at me before. I laid down on my bed trying to think what I may have done to make her snap at me. A few minutes had passed when Linda yelling from the living room “take off your clothes and get ready for your bath.
Linda was only 5 foot and was about 160 pounds but was very strong in her arms and hands. Her grip was like a vice and she was strong enough to pick me up and throw me across the room if she wanted to. I on the other hand was 4’ 9” about 100 pounds if that, I have a thin build and not much muscle.
I normally took my bath in the evening after dinner, but I was hot from the work outside and did as I was told. I was down to my under wear when Linda came into my room, she had a angry look on her face and was carrying some of the clothes from the trash bags and threw them on the bed.
She said, “I told you to get ready for your bath” I replied, “I am” she grabbed me by the arm and sat down pulling across her lap holding me down and began to spank me saying “from now on your will do as I say, when I say, and you will not tell anyone what happens when we are alone. As she spanked me as hard as she could I was screaming for her to stop.
I had never been spanked by my mother or father like this, the most I received from them was a swat on the butt, that was all it took for me to behave. She spanked me until at one point I passed out and came too, the whole time she continue spanking. I was crying so hard I wasn’t making a sound. It was hard for me to catch my breath, each blow sent me jerking forward.
All the time she yelled, “you will do as I say, when I say, and you will not tell anyone what happens when we are alone” over and over again she yelled it at me. After what seemed like a hour or more she stopped, grabbing me by the hair and jerking my head up to make eye contact.
She asked me, “do you understand me? I was crying so hard all I could do was shake my head yes. She said, “I did not hear you and hit me a few more times, I screamed out, “yes I understand you” she was still hitting me, I begged her to stop saying, “I will do anything you say, please stop” after I said that she stopped and helped me up to my feet.
I stood there with my underwear down around my ankles, right in front of her, she had both of my wrists in her vice like hands looking me in the eyes, I couldn’t look her in the face my head hung down and still crying, tears running down my face. She asked, “do you understand what I am telling you”? I said in a low shaking voice, “Yes, I understand”

How take your underwear off and follow me, it is time for your bath, as I removed my underwear, as Linda was started the bath water, the steam came up from the tub as I entered the bathroom. The water had a sweet smell of roses and was of bubbles, Linda ordered me into the tub.
The water was so hot that it made my toes turned pink “the water is so hot” I complained, she told me to get in and stop complaining. I slowly lower my body into the tub until I was covered with bubbles, “now doesn’t that feel nice” Linda asked in a smug voice. I had admit that it did feel good all thou I did not tell her that.
After sitting there for a few minutes, she retrieved a razor and lady shaving from the under the sink, and told me to lift my leg and place over the side of the tub. I did as I was told not sure what she was up to, she rub shaving cream all over my leg and began to shave it, starting at my ankles and working her way up to where the tub water covered the rest of the thigh and started doing the other leg.
She stopped and handed me the razor, And told me to shave the rest of my body like she showed me, I took the razor and finished the other leg. She had me shave my crotch, and under my arms, my chest, and down the crack of my ass.
I was to shave myself every other day, she would see that I did this on a daily basis and if I missed a spot it would mean trouble for me. After I finished shaving, she handed me a pot scrubber and told me to scrub every inch of my body, she wanted my skin a nice pink color.
I scrubbed my body like I was scrubbing a pot or pan, until my skin was a pink color all over even my feet and toes. She told to stand up so she see what kind of job I did shaving and scrubbing my body, “not bad, now wash your hair and use conditioner so that your hair is nice and soft.
I dried myself off with a large towel that Linda had hung the back of the door, she told me to come back to my room. I rapped the towel around my waist and joined her, she said, “that’s not the way to wrap a towel around you” taking the towel she wrapped it up under my arms and tucked it in in the front. “That’s better, you must start acting like a young lady.
I was stunned at her statement, and was going to say, I am not a young lady, but thought I had better not say anything or she might go off on me again. So I just kept my mouth shut. She said, “from now on when we are alone just you and I, your name is Dedra and you will dress, act, and talk like a young lady.
“You will not tell anyone about this or I will kill you and your mom and make it look like someone else did it, do you understand me” I looked into her eyes and saw a deadly stair that was as dead as I would be if I did not do what she said. I shook my yes, but that was not good enough, “answer me” she said, “yes” I said in a pitiful voice.

She said, ” that as soon as your mom leaves for work (7:00am) I was to take me bath and shave once a week, wash my hair and put on the outfit that she will lay out for me. In the evening before your mom comes home at (7:30pm) you will change at 7:00 back into your other clothes leaving your girls underwear on underneath.
I am going to teach you everything you will need to know to be a young lady, and when you make a mistake or do something wrong you will be punished. It was like a might mare that I would surely wake up from soon, but it was real and I was scared to death.
I stood there looking down at the floor, when the door bell rang, Linda told me to stay here, while she sees who at the door. I was like a statue made of marble not moving looking down at the floor, only when I heard Linda in her room did I look up and though the connecting bathroom , I saw her reading a letter.
After she had read it , she ripped it up into small pieces throwing it away, she said in a low stern voice “that bastard can’t hurt anyone again my he roast in hell. She stood there looking out the window, and then gave a little smile turning towards me, I looked back down at the floor as she came back into my room.
“Now Dedra” she started off saying, I would come to like being called that, but for now it scared me to death when I heard it. “I am going to help you get dressed and I want you to pay attention to every detail, I want you to learn everything there is to know about being a young lady“.
She continued, “Everyday you will learn something new, I expect you to improve each and every day, if you do not do what I tell you to do or are not trying hard enough, the punishment that you received earlier will be nothing like what will happen if you do not mind me.


Chapter two

My first dress

Linda looked at me, taking her hand raising my head so to make eye contacted, as they did I tried to look away, but she said, “look at me” as I did her eyes looked deep into mine, it made me nervous and I started to shake uncontrollably. She took me into to her arms and held me tight.
I did not like that, the only one in my family that did that was my grandmother and I like that but only from her no on else. My mom never hugged nether did my dad, and I wasn’t used to someone hugging me.
Linda whispered in my ear, “it is going to be all right, and we are going to have fun dressing you up in pretty things and you will come to like it I know you will” her words were no comfort to me, I just stood there arms to my side like a rag doll that she could play with.
Still shaking with tears running down my face, she released me and stood up, turning towards the bed and eyeing the clothing laid across it. She started to go though the pile of panties and picked out a pair of white lace with ruffles across the rear, but changed her mind, tossing then aside.
She took another pair out of the pile and held them up, “these are the ones. I was looking for” she said to herself, but loud enough. I was starting to cry all over again, as she bent down and held them open for me to put on, I was so scared that I could not keep my balance trying to steady myself one foot.
She told me to hold on to her shoulder for balance, but I did not want to touch her. So I reached for the chair that was near by and held on to it, I put one foot then the other in the panties as Linda slowly raise them up to my waist line, then taking a step back she looked at the small bulge in my panties.
She scathed her head and was thinking about what to do with my small boy hood, after a minute or so she told me to stay put she will be right back, and left the room. When she returned she had a pink ribbon in her hand, she bend down to her knees and pulled my panties down half way to my knees.
She took hold of the ribbon and folded it half taking the folded end and started to wrap it around the base of my little dick. Around and around she wrapped it until the head was the only thing left showing, tying the two ends together, she took the rest of the ribbon ends and tucked them between my legs, forcing my legs apart.


As I did her hand touched the head of my penis, it sent a shiver up my spine, she reached around and pulled them tight up and back forcing my penis to disappear. After she was sure that it could not be seen, she took one end in each hand and crossing them, she wrapped them under the cheeks and pulled them tighter, making my ass full and wide like a young girls.
She tied it off under my belly button, it a small bow. She sat back on her knees and looked at her handy work. She said, “now that is much better, now is in it” not sure if she was wanting me to answer her, I said nothing, she pulled the girls panties back up and said, “you look like a real girl, you even have a small slit showing like you have a virgins.
I started to cry, the tears running down my face, this time I did not try to hide it.
I just cried out loud as she reached for a girls bra, that matched the panties. She showed me how to put it on upside down and inside out hooking it in front and turning it around. Still crying and now shaking as she pulled up the straps.
I wanted to run away, but dressed in this where would I go, I could not do anything to stop what was happening to me. Linda stopped after the bra was in place and adjusted correctly, and sat down on the bed in front me, she looked me deep into my eyes, I turned away from her stair.
She took me gently by my chin and turned my head back to face her staring eyes.
She did not say a word for the longest time just looked into my eyes, I was doing my best not to look at her, when she broke the long silence and said, “there is nothing to be ashamed of you are a girl and you need to start to dress and acted like one”
If she was trying to comfort me, it was not working nor was it making me calm down. She told me to stop crying or I will be punished, like I was earlier, that put a quick end to any sound coming out of me. I was still crying but not making a sound, but the tears gave me away.
She did not say anything about it, or act like she didn’t cared. She picked up two form rubber falsies, that were in the pile of clothes. She said. “these will give you a head start on be coming a girl, as she placed them under the cups of the bra. I watched as she had told me to, but was discussed at the change that was happing to me.
She took a step back to check out how I looked so far, “very pretty” she said, with a sly smile. I was wear white panties with little pink dots and a matching bra, that was a 32 A juniors. I had a shape of a preteen girl, 12 or a little older. After approving what was done so far, she rummaged through the pile and pulled out a pair of nude panties hose.


With a smile, she told me to sit down on the chair, she said, “now watch me very closely. I want you to learn how to put panties or stockings on without putting a tear or run in them” I watched closely as she rolled one leg of the panties hose up. She told me to point my toes as she placed the seam of the hose across the tip of my toes.
She carefully unrolled the leg until it was just under my knee, she told me to do the other leg like she had showed me. I made sure I did exactly like she did the other leg,. After I had got it up to where the panty part was even, she showed me how to pull it the rest of the way up. As I was pulling them up the feeling of the panties hose and my freshly shaved legs felt so wonderful and silky smooth.
She picked out a pair of little girls lace ankles socks and put them on me. Then she said, “ now for your shoes” she had several picked out sitting next to the bed. I did not say anything but they all were high heels and was unsure that I could walk in them. She picked out a pair of white sandals with ankles straps that had at least a three inch heel. She had in sit down as she showed me how to put then on.
She then had me take hold of her arms and stand up, as I did I almost fell when I was standing up strait. It was hard to balance on the high heels. She held my hands as we walked around the room. After three or four times around she suddenly let go and I was on my own. Surprisingly I was doing pretty good until I caught my heel on a torn part of the carpet.
I fell on to my knees, I was afraid that I had tore my panties hose and Linda would punish me, but luckily I didn’t. she told me to get up. As I did I had a hard time doing so, she did not help me, saying you have to learn to do things by yourself. After I had gotten to my feet, she told me that I have to watch where I am walking and where I place my shoe to make sure things like this don’t happen again.
I walked around the room a few more times, when Linda stopped me and said, “ we got to finish getting you dressed. She had hung a dress on the back of the door that I hadn’t seen. She said, “This is Dedras first dress” holding it up. I was so embarrass that I started to cry again.
She stopped and hung the dress back up, saying I almost forgot, she started picking though the pile again and pulled out a pair of white sissy lace bloomers, the butt was covered with rows of lace and around the trim. The kind a baby or very young girl would wear.
The tears were running down my face, after seeing the dress I knew that the bloomers would be visible with the dress on. She held the bloomers so I could put my shoes though the legs openings without tearing them. I put my hand on her shoulder to balance myself.

After she had pulled them up, she had me turn around so she could se how they looked, making the comment very pretty. I was still crying and could not stop, shaking from head to toe. She took down the dress and took it off the hanger. She unzipped it and had me raise my arms.
The dress was a white little girls dress, it was covered with lace very short and had a petticoat liner, which made the him of the dress flare out, puffy lace sleeves and a big lace tie that tied in the back. As she slid the dress over my head it seemed to tight for me, but after it was all the down it wasn’t as tight as I had thought.
She zipped it up and tied a big bow in the back making my falsies stand out, giving me more of a girly shape. The bottom of the dress was so short that my lace panties were showing almost up to the waist band. Linda went back to the pile looking for something, that when she couldn’t find it, it mad she agree.
She was muttering something like, I know they were here, after looking for over five minutes or so, she stopped looking for what ever it was and told me to stay here, that she would be right back. She returned shortly with a pair of white gloves, like kind girls wear to church on Sunday.
She started to put them on me, and stopped saying that I need to polish my nails but that it was to late for that because I had my shoes and hose on already. We will do that tomorrow. That started me crying again, the thought of having to do this all over again was more then I could take.
I finally broke my silence, I asked her, “I have to dress up like a girl again tomorrow”? her reply sent me into a pure state shock, She said, “ you will dress like a girl everyday that we are alone and your mom is at work” I did not say a word the rest of the day.
It was like I was in a night mare and I could not wake up, I was crying and shake all over. She put the gloves on and told me that I needed a little makeup, she left and returned with a large makeup box. As she rummaged though it picking out items, I just sat there looking at her.
There was a serious look to her face that scared me. It was a look that said I am not messing around, I mean what I say and I will do anything to you that I want, when I want. I was crying with the tears streaming down my face, and my hands were shaking so bad, I tried to take a drink of my soda that I could not hold it to my mouth.
She started to apply a light pink blush to my cheeks, saying you need a little color to your face. Then a little white eye shadow just below the brow line, a light coat of brown mascara and a light pink lip stick. She looked over her makeup job, saying that’s better.

How for the final touch, she said to herself taking a blonde wig off a foam head that she had hidden behind some things on my dresser. It was a little longer then shoulder length, had small tight curls, and long bangs that were curled upwards away from the eyes.
She stood up and took a step back, then told me to turn around slowly. As I did I could feel her staring at me. Very, very pretty young lady you are Dedra she said as I turned around for her enjoyment. You into to you mothers room and take a look at Dedra for your self she said.
I slowly walked into my moms room where she had mirrored closet doors, so I could see myself fully from head to toe. I closed my eyes afraid to see what I looked like. I turned toward the mirror and slowly opened my eyes.
I did not recognize the girl standing in the mirror in front of me, I felt the tears start building up inside of me as I slowly turned around staring at the mirror. I was looking at a preteen age girl, dressed like the girls I had seen at church, expect for the very short dress that showed almost my entire ass. That part looked like a little girl around three or four with the lace panties.
I was crying and my mind was racing, thing that I was going to have to dress like this every day that my mom was gone to work, or when Linda and I were by are alone. Linda came into the room, and asked me what I thought about how I looked, I just looked up at her for a second and ran out of the room.
I ran into my room and fell down on the bed crying and screaming, “I don’t want to be a girl. Well that was my first dress, after that day I learned everything there was to learn about dressing, acting, walking, talking like a girl. I had to read teen girl and women’s magazines and was quizzed about the stores. This went on for over two and a half years.
Until Linda met a Marine at a Thanksgiving dinner one year, after they got married she disappeared, never to be heard from again. She did leave me clothes she had bought me and a daily journal that she had kept during the time she was working for my mom. It was a very detailed account of my life as Dedra.
I did not know why she left it for me, but I kept it until I was seventeen or eighteen. I must have read it a thousand times, keeping it hidden away, not showing it to anyone.

The End

rm_lisann4 66T

2/26/2006 8:22 pm

Dear Dedra your story of being made to dress as a women is it true or just a story I love dressing as a women but at a young age that would be a hard one to deal with your friend lisann.

DEDRATVCALIF replies on 2/6/2007 10:29 am:

randioralone 58M

3/28/2006 9:58 pm

Blogs like yours will keep helping people understand why people are who they are. Thank you for sharing a small portion of your life with us.

DEDRATVCALIF replies on 2/6/2007 10:32 am:

rm_marke1964 52M

4/13/2006 12:13 pm

Hi dedra I am from Tulare visalia area and would like to meet you.

justyoumexxxxx 41T

6/5/2006 6:16 pm

I wish I hope with you my love

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