Crystal's StorySite


My First Time Completely Dressed

by Sally Ann

Part II


The episode at my cousin Haley's had a profound affect on me. The undergarments had raised indescribable feelings within me. I wasn't aware of sex or what sexual feelings were. I just knew that I wanted to experience those feelings again.

Over a period of months I was able to acquire some clothes from Haley. Just odds and ends, things she didn't want anymore. One of my favorites was a green, one piece bathing suit. For whatever reason it gave me intense feelings.

I hid my little stash of clothes in the back of my closet and would dress up any time I had the opportunity. My Mom would leave me alone for hours at a time, especially on weekends. I would use that time to dress up. I loved those moments. I would prance around the house acting as much like a girl as I could.

I thought my hiding place to be secure. In my young naive mind nobody would ever look back there. I came home one day from school, went directly into my room only to be shocked to find my entire feminine wardrobe piled neatly on my bed. A minute later my Mother followed me into my bedroom.

"Well "she said "I think you have some explaining to do young man. What on earth are these clothes doing in your closet? Where did the come from? And what is the purpose of them?"

She was standing there with her hands on her hips looking at me over the tops of her glasses. My mind was racing my face flushed with embarrassment over being exposed. Before I could begin to answer she told me in, no uncertain terms , that she wanted the whole truth. I was busted.

I hemmed and hawed. "Out with it young man" she ordered.

Caught dead to rights I slowly told her the story. She knew of my little escapes at Haley's house but didn't realize the effect of our dress up playing. I told here that the clothes made me feel funny and that it was a good feeling. I told her I didn't know why , it just did. As I confessed the look of consternation slowly left her face.

I was made to tell her how I would dress up when no one was home. As I went on she prodded my for details. I made a clean breast of it. I asked that she not be mad at me. She asked me if I had ever worn any of her clothes. I said that I had not, I hadn't, hers were much to big and not anything a young girl, which I fancied myself to be, would wear.

She could see that I was very upset at being exposed. Being the loving mother that she was she hugged me. What a relief.

My Mom was and is a very kind and understanding person. She was mainly upset that I was sneaking around. She didn't like sneaks.

To my surprise she told me that if I wanted to keep the clothes (I think I might have had at most 15 items) that I should put them away properly. I should also have them in the laundry like any other clothing. She could she that the 2 pairs of panties had been worn many times and told me that it was disgusting not to launder ones undergarments.

The talk had turned from a confession to a lecture on how launder and properly store clothes. I found myself so relieved. I was relaxed talking to my Mom about dressing up as a girl. Every young man should have such a wonderful Mom.

She went on to tell me that I could go on with my "hobby" but that there were rules and that one of them was to NOT go out of the house dressed "like that". I was to keep my hobby to myself . I was to be careful when home alone not to be caught by an unexpected guest, our neighbors did come in that way. I had already had a close call.

She told me that I need not "sneak" that I could dress while she was home if I wanted to but that she was the only one I should dress around.

With that she picked up the garments and left the room. She took them to the laundry room. Minutes later I heard the washing machine start, I knew what was agitating in the machine. It made me feel really strange knowing my Mom was washing my girl things. I was also relieved to have my little secret out in the open.

The next day when I came home from school I found my 3 dresses hanging in my closet with my male attire. My green bathing suit hung next to them. I later found the rest of my stash, all undergarments, in my drawer. I was overcome with strange feelings seeing my panties folded neatly beside my jockey shorts. One of my most prized garments , my yellow nylon slip was in my other drawer.

I was missing my pantyhose. I was later to find out that Mom had thrown them out. She explained that they were to big for me and that they were full of runs anyway. She told me that she would get me some new ones one of these days when she was out. I also got a lecture on cutting toe nails to avoid running the delicate material. It was more like a Mother Daughter talk, she was so calm and matter of fact about everything.

The shock of getting caught had made me a bit leary about getting dressed up again. The thought of doing it with Mom around was also a bit unsettling. But about two weeks had gone by and my desire to dress up was growing stronger. It didn't help that my little wardrobe was right in my face all of the time.

The clincher was when my Mom, being true to her word, presented me with a package containing two pairs of pantyhose. She admonished me to "remember what I had been told about my toe nails". And that "they didn't give these things away at the store". Being an observant women she had noticed that my wardrobe didn't contain any shoes so she picked me up a pair of inch high pumps from the Salvation Army store . She told me to tell her how they fit when I was in the mood to try them on.

It was a Saturday morning, I couldn't stand it any more. But I was still very apprehensive about dressing in front of my Mother. I knew that she would more then likely being going out for a while as she usually did on Saturday. I was caught in a dilemma. Mom had told me not to sneak and that was exactly what I was planning. I didn't want to sneak but I felt it would be to embarrassing with her there.

Moms are physic, intuitive beings. She told me that morning that she would be going out for a while and that if I wanted to dress up that I should do it before she left otherwise I would be a sneak and she hated sneaks (my father had been one) and that's why he wasn't around anymore.

She told me that she wanted to see if the shoes fit properly and that I probably needed some instruction on how to properly put on hose. She was right about that.

"So do you have plans today young man " she asked . She could tell by my sheepish attitude that once again she had done a mind probe on me." Well pick out what you want to wear, take a shower , and we will get on with it". "I know that you are embarrassed but you need not hide anything from me. I'm the person who gave birth to you. After today the embarrassment will have gone away and you will be more comfortable". "Call me when you need help with the hose".

With that she left the room. I went and picked out my favorite dress, my slip, a pair of panty hose still in the package and a pair of panties and headed to the shower. Mom caught sight of me headed for the bathroom. Oh it was still embarrassing, but my desires overwhelmed my embarrassment.

In the bathroom I hung my dress from the towel rack, and placed the other garments on the closed toilet seat. I pulled off my tee shirt and dropped my jeans. The thought of what I was about to do had my little man standing at attention. It was straight out as I dropped my jockeys. I still was to ignorant of the facts of life to draw the connection.

As I shampooed and showered I almost forgot about what was waiting for me outside the shower curtain. I turned off the shower and dried with the towel I had haging over the curtain rail. I stepped out and there they were. Like they were not inatmate objects or something. They were only cloth yet the thought of wearing them and not sneaking was driving me crazy. Here goes, I reaced for the panties. They were nothing special , just nylon hip huggers, the elastic had come loose in a couple of spots. But they were clean and soft from being laundered. I slipped them on. Oh the feeling the whole thing was surreal. I next pulled the slip over my head. I was just taking the dress off the hanger off when I heard my Mom at the door.

"Are you ready for me?" she asked through the door. "Just a second" I replied.

The dress was another "not special" item . Just a light green cotton dress with puffed short sleeves that buttoned up the back. It was similar to the one that I had dressed in at Haley's house but didn't tie in the back . It to had some rough edges but I liked it.

I jumped into it as fast as I could. Somewhere in my immature mind I thought it wasn't as bad presenting myself to my Mother dressed as opposed to being in girls underwear. I struggled to button the back but as usual I could only get the top two buttons.

"Ready dear? " came through the door. "I guess so" I replied. This was it. The door began to open.

My Mom entered the room. There in front of her stood her son in a dress head hanging. She stood for a couple of seconds surveying the situation. She walked over and picked up the hem of my dress and made a remark about the hem coming loose in a spot. Everything was so matter of fact to her. She turned me around and noticed the 3 buttons that hadn't been fastened. Without a word she fastened them.

I know she felt how uncomfortable I was that's why she went about her business as if this was a normal situation. She sat me down on the Toilet, opened the pantyhose package and instructed my on the fine art of putting on hose. All of this with no hint in her facial expression that anything was wrong. She had me stand up and pulled the hose up around my bottom. She had to feel the panties but still it was all so matter of fact.

"Your head is soaked" she said as she grabbed a towel and dryed my head. My hair was not real long but long enough that it could be mistaken for a girl. Mom grabbed the hair dryer and a brush. In an couple of minutes it did look like a girls hairdo.

"Where are your shoes dear ?" Mom asked . "I left the in my room" I answered. "Wait her I'll get them " she ordered. "You don't want to ruin a new pair of hose trouncing around in your bare feet" She left to retrieve the shoes. The new hose were so tight compared to the old, stretched out ones I had been accustomed to. They clung to me in such a way as to cause those wonderful feelings that I had been long for. They also compressed around my crotch and buttocks, it was wonderful.

In a minute she was back. She sat my again on the toilet ,knelt down, and gently pushed one foot into the shoe. She pinched the toe to see where my toes were.

"Good" she said "I thought they would be about right, and there is a little room to grow into". Moms are so practical even when buying pumps for their son.

She fitted the other shoe and stood me up.

"Try walking in those sweetheart" she instructed me.

It was a piece of cake the heels weren't that high, besides I had had some experience at my cousin Haley's .

"Now are you still embarrassed to be around your Mother ?" she asked. "A little" I replied . "Well you will soon get over it , it's better then being a sneak . You will probably grow out of this as you get older. My job is just to see that you mature as a responsible person. That means know sneaking. There is nothing that you can not talk to your Mother about". She again reminded me who had carried me and given birth to me.

"Now come on we will go into the kitchen and I'll get you some breakfast" I followed her to the kitchen being amazed at the clicking of the shoes as I walked. I was in sort of a daze I don't think I have words to explain what it was like.

In the kitchen I was instructed hw to smooth my skirt under me as I sat and how a girl keeps her legs together. I found that keeping my legs together wasn't that easy. Mom made me some eggs and toast and we ate together. We talked as we ate not anything to do with my makeover. I was relaxing now and assimilating into my new role when a knock came to the back door.

I was about to make a mile when Mom stopped me with a hand on my shoulder. "Sit right there sweetheart I'll see who it is. If I give you the sign just get up and go to your room". My heart was pounding .

Mom went to the door which was attached to the kitchen. It was a contractor she had talked to earlier in the week he had come to give her some estimates on the siding. It was clear to me that if I could see him he could see me. But I was far enough away from the door that know way would he know that the girl setting at the table was a boy. Somehow it was actually exciting. Being dressed up with someone else around.

Mom had a brief conversation with the man and thanked him as she closed the door.

"I've got to get ready . Your Aunt and I are going to do some shopping . Be a sweetheart and do up these dishes while Mommy gets ready" .

I followed her instructions and cleaned up while she did her thing. I couldn't help several trips into the hall way to admire myself in the full length mirror. It was like I had been reborn. The thought of growing out of it was terrible. I simply loved being a girl.

Mom finished getting ready and was in the kitchen when the phone rang . It was my Aunt, Haley's Mother. Apparently Haley had an accident playing field hockey the day before and her ankle was swollen. She could not go shopping with her Mom and Aunt as they had planned. My Aunt asked if I could come over and stay with Haley while they were out. Mom told her to hang on and that she would get back to her in a few minutes.

"Well I think you are going to have to change dear and go sit with your cousin." Oh what a bummer I thought . I had the greatest plans to be a girl for the resr of the day.

My mind raced. I was bolder now having gotten over the initial embarrassment . "Why can't Haley come over here?" I asked .

"You would still have to change dear" Mom replied.

"Why" I said. "Haley knows I like to dress up as a girl, these are her old clothes remember".

"Well I think my sister will think of it as a bit strange but if you are up to it I'll see if Haley can come over.

Mom got on the phone and in a few sentences it was apparent that Haley could come over. Mom also hinted that she had a surprise for her sister and that to be prepared .

About a half hour later my Aunt and Haley pulled into the driveway. A couple of seconds later My Aunt was helping Haley, hopping on one foot , through the door. I was sitting at the kitchen table back to the door as they came in . I turned my head and started Haley straight in the eyes and smiled .

"No way " was her reaction. She smiled and laughed. "Isn't he beautiful Mom, look at Jamie ".

"Well " replied my Aunt "It's not like it's the first time. And I do recognize the dress" she laughed.

That was it. Aunt Alice changed the subject and talked to my Mom about the days itinerary . I was now OUT for all practical purposes. Aunt Alice gave Haley and I last minute instructions and the two were gone. It was no big thing.

Haley surveyed me for a couple of moments. "You need some makeup on that puss hon " . Before I knew it I was head back getting my face painted. And loving every moment of it I might add . Haley spent an hour or so using me as her own personal doll. She did my hair differently and added a couple of barrettes . The result of her efforts was a very convincing young 11 year old girl .

"You should have come over to the house I could have put you into something nicer then those old rags" Haley taunted me. I was starting to feel self-conscious about the dress that only a few moments ago I was so proud of .

"I've got to come up with some way to get us over to my house" said Haley.

It wasn't but a few minutes later that Aunt Alice was on the phone only to check up on us. Haley was an excellent whiner. Before she was done she had hatched a scheme to get us to her house. But this was to violate the rule that I wasn't to go out side dressed in girls clothes. Haley convinced my Mom that everything would be all right. My Aunt ordered a Cab for us, it was only eight blocks or so but Haley couldn't travel on that foot and I felt super uncomfortable at the thought of running into some of our school mates on the way. All I had to do was to fool the Cabby.

Next thing you know Haley and I are hopping her into the Cab. I was feeling super self conscious . My oufit was a shame compared to Haley's. The cabby turned out to be a lady who was more concerned about doing her job then checking out a 11 and 12 year old. We were there in a flash.

The rest of the day was a young cross dressers dream. I was in and out of so many outfits that it made my head spin. I also acquired a few more items for my wardrobe in particular a couple of hand-me-down padded bras.

Haley also had a couple of inexpensive but believable cap wigs The wigs made such a difference. There is nobody on this green earth that could guess that I was actually an 11 your old boy.

So ends another chapter in the life of a boy who will "probably grow out of it "... Ya right.




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