Andrea's First Day

by Janis Elizabeth

 

"Well, Andy, you have finally run out of clean clothes to wear. You know you agreed to help me out by doing the laundry while I was at work. Now, since you didn't do as you were supposed to do, you have nothing to wear. All of your things need to be washed or they should be discarded because they are worn so bad."

My fifteen-year-old son Andy looked at me as I said these things to him. He knew he had not followed through on his responsibilities and he also knew that he had let me down. For a second or two, he couldn't look me in the eye, for to do so would be a tacit acknowledgment that he had failed me. Finally, he asked me what he would do for clean clothes today.

I looked at him neither kindly nor crossly and said, "As I see it, you have two choices, my son. Either you can wear nothing under your shirt and jeans or you can wear some of my things. I wouldn't recommend the first choice as you have sensitive skin and you will find yourself getting chafed in many vulnerable areas. However, the choice is yours."

"Mom," Andy pleaded. "I'm a boy. I would feel silly wearing your things. What if someone were to notice? What would I say about having to wear your underwear? I would be so embarrassed."

Although I heard every word of his lament, I pretended to ignore what he had said. I told Andy to stay put in his room while I briefly went to my room. When I returned, I was carrying some of my silky underwear and some other items. "Put on these panties and make yourself decent Andy."

Andy blushed as I handed him the white satiny panties. He started to complain but then understood that any protest would really be futile. Grudgingly, he turned his back to me so as not to embarrass himself any further. He removed his pajama bottoms and stepped carefully into the panties. I could almost hear him utter a sigh of contentment as he slid the garment into place. I reminded him to tuck himself between his legs, to hide any telltale bulges, which he promptly did. As he turned around, I could see that he was being torn apart by his emotions. One side of him was enjoying the pleasurable sensation of the satin on his skin. The other side was trying to remind him that he was a boy and boys don't normally wear satiny panties.

Next, I coaxed him out of his pajama top and handed him a white satin and lace camisole to wear. With somewhat less reluctance than his reaction to the panties, he took the camisole and slid it over his head and down on to his chest. I then handed him a pair of black knee-high stockings, saying that he didn't have clean socks to wear either. Besides, at first glace, these knee-highs could almost have passed for dark black socks. With a feigned show of reluctance, he sat down and carefully slid the knee-highs onto his legs.

I smiled inwardly watching my son put on my stocking and lingerie. I then handed him a silky, white short sleeve blouse. When Andy saw the blouse, he again grew upset. "But Mom," Andy wailed, "That's not a shirt. That's one of your blouses. While it's very plain, it's still a blouse. I'm not a girl and I'm not wearing any more women's things." I gave him a stern look and his resistance withered as quickly as it had arisen. He slid the blouse on his arms and over his body. He had some trouble fastening it, because the buttons were reversed from his shirts. I offered to assist him in buttoning the blouse, but he said he would mange somehow. I noticed that he furtively let his hands feel the fabric of the blouse on his arms and over his breasts as he buttoned it.

"Andy, you might as well wear these black pull-on pants also. You don’t need to wear a belt with them." I sensed that his reluctance was now just for show and that he was not seriously resisting wearing my things. He then donned a pair of my flats that slid on his feet perfectly.

For a few seconds, Andy just looked at me before speaking. "Mom, I never realized how nice clothes could feel on me. Is it wrong of me to enjoy wearing these soft, silky things." I gently assured him that there was nothing wrong in wearing women's things and pointed out that many men loved the feel of silks and satins against their skin. He then asked, "Do you think I would look pretty dressed completely as a girl? I mean, would wearing makeup and having my hair done make me look less boyish?" I assured him that, in my mind, he could be a very lovely young lady, if he were dressed properly and had his hair and makeup done. I then asked if he would like to see how he would look as a girl. He smiled shyly at me and quickly nodded his head.

At my direction, Andy went into my room and sat at my vanity, facing away from the mirror. Before starting on his makeup, I covered him with a pink plastic shampoo cape. "Are you sure you want to do this" I asked? As he looked at me, he smiled and nodded. I then applied a thin coating of liquid foundation over his face and covered it with powder. A light coating of pink blush was carefully applied along his cheekbones. I had him close his eyes while I daubed pink eye shadow on his eyelids. Finishing with his eyelids, I had him open his eyes and sit very still while I brushed some mascara on his upper and lower lashes. Lastly, I lined his lips with a lipstick pencil and filled in the outline with several coats of creamy pink lipstick. I then had him blot his lips together on a tissue.

"Andy, rather than try to do something with your hair right now, let me get something from my closet for you. No fair peeking at the work still in progress," I said. Andy smiled and assured me he would be patient. I went to my closet and took out a wig box that I had stored there. Opening it, I removed a lovely wig from the head form. The wig was styled so that the ends appeared to curl outward. It was in a color that matched my own hair. Coincidentally, it also matched Andy's hair. I placed the wig on his head and brushed it slightly. I also brushed the bangs properly into place over his forehead. "Are you ready to see the finished product" I asked? Nervously, Andy nodded his head. I had him turn and face the mirror.

He was stunned speechless for a few seconds when he saw his image. At last, he looked at me and said, "Mom. I look better than I had hoped to look. I think I look very pretty. In fact, from some of the old pictures I've seen, I look exactly like you did when you were my age." I smiled at his comparison and agreed that he did bear a striking resemblance to me when I was in my teenage years. I told Andy that he looked very pretty indeed and would have been lovely had he been born a girl. I leaned down and gave him a quick hug.

After again looking in the mirror, Andy then said that if he had breasts, he would really look like a girl. I asked if he would like to temporarily experience having breasts. "Mom, I would love it," he replied eagerly. I removed his shampoo cape and had him carefully take off his blouse and camisole, so as not to muss up his hair or makeup. I then opened my lingerie drawer and removed several items. I had him slide the straps of a white, satiny bra on his arms and over his shoulders. Lovingly, I hooked the back of the bra for him. I then put some realistic B-sized breast forms into the cups of his bra, giving him the feel of the added weight on his chest. He smiled again as he viewed his girlish image in the mirror.

"Andrea, dear, would you like to wear a dress instead of a blouse and pants," I asked? Andy noted that I had referred to him by a feminine name and smiled broadly. He indicated that it would be nice to wear a dress. While he removed the flats, knee-highs and pull-on pants he had on, I went into my closet and returned with a lovely dark green satin dress with short sleeves and a full skirt that would fall to just below the knees. I first removed a full satin slip, garter belt and black stockings from my drawer and gave them to Andrea to wear.

I explained how she should wear her garter belt and she followed my instructions perfectly. Next, I showed her how to put on her stockings and attach them to the garters without causing any runs in them. As she slid the satin and lace slip carefully over her head and down her body, I watched as she experienced the sensations of the satin on her body. I then handed her the dress. "It's lovely, Mom. But I have never seen you wear this dress before." It was my turn to smile as I explained that I had gotten the dress especially for her, with hopes that she would wear it one day. I told Andrea that I knew she would make a lovely girl and I wanted to have a lovely dress ready for my new daughter to wear, just in case.

She carefully slid it over her head and settled it around her waist. She raised the top and slipped her arms into the sleeves. Turning around, she asked, "Mom, will you zip me up?" I quickly helped zip up the dress for my daughter. I had her sit on the bed and I helped her into a pair of one-inch heels. I then helped Andrea to stand up, making sure she kept her balance and then held on to her as she took her first teetering steps in heels. I watched as my daughter mastered walking in heels, taking small steps, which allowed her to keep her balance.

Andrea again sat at the vanity again for some finishing touches. I put a single strand of simulated pearls around her neck, a pair of pearl clip-on earrings on her ears and then I sprayed her with some feminine perfume. I had her walk around, so that I might see how the dress fit her from all angles. I must admit it was a perfect fit.

As Andrea sat on the bed, naturally smoothing the skirt of her dress under her, as if she had been doing it all her life, I started to speak. "Andrea, I know we have come very far in a very short time. I hope you won't feel like I'm rushing you or pushing you but……." I faltered in my speech, unable to go on. Andrea looked at me and said "But what, Mom?"

I regained my voice and continued. "Andrea, there is one more dress I would like to see you wear sometime. It doesn't have to be today. It's a special dress for me and I want it to be special for you. Would you wear my wedding gown, so I might see you in it?"

Andrea smiled and asked me if I wanted her to model it. I replied, "No dear. I want to see how my daughter would look as a lovely bride." She leaned forward and hugged me saying she would be pleased to wear my bridal gown. I then said that maybe she would like to wear my wedding night negligee to bed sometime. She smiled and nodded, saying she would be proud to wear my negligee to bed. I struggled to hold back the tears of joy but I did not succeed. My eyes flooded as I smiled at my pretty daughter. I reached out and gave her a big hug.

Regaining my composure, I said I wanted to show my pretty daughter off to the world. Would my Andrea be interested in going out to eat and then going shopping? Andrea smiled and said she would love to go out as my daughter. The rest of the day was a typical mother-daughter outing. We talked. We laughed. We shopped. In general, we just had a good time. At bedtime, I watched as Andrea changed from her dress and lingerie into a knee-length pink satin nightgown with lace all over. She looked so innocent and adorable in the pink satin. As she got into bed, she looked at me and said, "Mom, I had fun being Andrea today. It was very nice." I hugged her and said that, hopefully, there would be many more occasions for my lovely Andrea to join me and be the daughter I have always dreamed of having. Andrea smiled and said, "I am looking forward to all the times that I can be your Andrea. Good Night Mom."

"Good night dear. Pleasant feminine dreams."

 

 

 

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© 2002 by Janis Elizabeth. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.