(Disclaimer: This is based on experiences I had, though I am adding a bit to cover what my mother's side of the story was, that is based on what I was told happened. It's a long enough story that it will likely cover several posts.)
I woke up the next morning and as I slipped out from under the sheets, I saw the nightgown I was wearing and it reminded me of the night before. I looked over to the bra and slip sitting on my dresser. I looked into my open closet to see the blue and green flower print dress I had been wearing the night before, hanging there, waiting for me to change into it once again. My mom had said I looked good as a girl, that with makeup on and my hair done, nobody would know I wasn't a girl. I thought about whether or not I really wanted to go that far or not, and decided that it probably wouldn't hurt to do it and it might be fun. It certainly wasn't what I had expected when I had asked my mother that question the night before, but then again, I realized that I wasn't sure what I wanted to know.
I left the nightgown on to go down and go to the bathroom. Trying to hold all the fabric up as I stood to pee, became rather difficult, but I managed to get it done and pulled the panties back up before heading downstairs. Walking in to the kitchen to grab a bowl of cereal, my mom was standing there already with a cup of coffee.
"Well, at least you didn't pee in my nightgown last night," she joked. I turned red and concentrated on getting breakfast for myself. She continued on. "You had said last night that you wanted to get your hair done today and some makeup on so you can see how much you really do look like a girl, do you still want to do that?"
"Yeah, I'd like to see what I look like," I answered sheepishly.
"Well, we've got that to do today, and we need to go do some shopping, so once you're done with breakfast, go ahead and change and we can get started on things," she finished.
As I finished gathering my breakfast, she finished her coffee and left the room to finish getting ready for the day herself. I ate quietly, thinking to myself about the plans for the day. If we needed to go shopping, I didn't want to go out wearing a dress. At the same time, if my mom spent a bunch of time doing my hair and getting makeup on me, I was pretty certain she wouldn't be happy to undo it all just so we could go run errands. I finished my breakfast, put my bowl and spoon into the sink, and headed back up to my room.
As I closed the door behind me, I looked at the dress in the closet again. It would certainly have to wait until after we got the shopping and whatever other errands we needed to run out of the way. I slipped off the nightgown, folded it, and placed it on my dresser next to the bra and slip from the night before. I looked down at the panties I was wearing and decided I should take them off as well; I didn't want to run the risk of having my shorts slip down my waist slightly and have the lacy edges of the panties showing while out and about. I took them off and set them on top of the nightgown, then got out a pair of my regular underwear to put on, together with a pair of shorts and a t-shirt.
Getting dressed, I put on a pair of sandals and went downstairs to see if my mom was ready to go or not. I went back to the kitchen to find her completely dressed and finishing another cup of coffee. She looked over at me, and noticing my attire, asked, "I thought you wanted to do hair and makeup?"
"You said we needed to go out, so I figured we would wait with it until we were done with that," I explained.
"Suit yourself," she shrugged her shoulders. "I guess we'll head out first thing then." She set her coffee cup in the sink and looked back to me. "I'm going to grab my purse, go ahead and get in the car and we'll go."
I went out, got in the car and strapped myself in. My mom came out and got in the driver's seat, started the car and we pulled out of the garage. As she hit the button to close the garage door, she began to talk. "I called your stepfather last night and told him about what you asked me." I looked over at her, afraid to hear what he had said about it. She obviously saw the fear on my face and went on. "Don't worry, he's fine with it. The thing is, you had said you would dress up again if the clothes were available, would you still do that? I mean, I understand you're worried about getting teased, but if we could keep it in a safe space where you don't get teased, would you dress up as a girl?"
I couldn't do much besides nod, somewhat in shock that she had told all of this to my stepfather.
"Well, we discussed that," she went on, "and we're both OK with you doing that, but it kind of presents a couple of issues. Your sisters certainly aren't going to want you borrowing their clothes, and depending on how often you want to dress up, I can't always make my clothes available. Not to mention the fact that sharing underwear isn't really sanitary. So the idea we had is to get you your own things. That way, you can dress up as often as you want. Not only that, but you'll get a bra that fits instead of trying to make do with one of mine." She chuckled slightly, noticing my nervousness, and trying to make light with the reference to the night before.
We kept quiet for a while, me slowly digesting what she just suggested, while she concentrated on driving. As we neared downtown, she began to talk more. "One thing about doing this for you: if we buy you these things, you don't just get to wear them in secret in your room. If we spend this money on you, your stepfather wants to see how you look in them, and your sisters will probably get to know as well. You should wear them somewhat regularly, so it'll be hard to hide it. Not only that, but I'm not going to do special loads of laundry for just your things, so everyone in the house will know. We'll make sure your sisters don't tease you, but there may be special occasions where we want you to dress up." We pulled into the parking lot and found a space. As my mother got out of the car, I was still unsure what to think about all of this.
She came over to my door and opened it. "Well, unless you've got something to say, let's go!" I got out of the car quietly and followed her into the department store.
Entering the store, she immediately headed to a section marked 'Intimates'. I followed my mother meekly, somewhat wanting to just disappear. She headed to a rack full of packages of panties, looking them over and noting the sizes. "Let's see, the size seven you wore last night seemed to fit perfectly...great! Here we are, size seven. She looked at the patterns and pulled out three packages, thrusting them into my hands. Not sure what to do, I said, "What am I supposed to do with these?"
"They're yours, you can carry them. Now let's get you a couple bras," she finished.
I looked down at the packages of panties in my hands, reading the front of them, trying to make sure I didn't make eye contact with anyone around. each package held three pairs of panties, 'Women's Cotton Briefs' was the description. I looked at the patterns she had settled on--tiny flowers all over, with light lacing around the legs and waist. I followed my mother quietly over to a rack of bras. "Let's see," she talked quietly, "here we are, I just got Mindy her first training bras last month, let's see if they have a 34 double A for you." I wanted to crawl into the carpet, the mention of my youngest stepsister reminded me that she would know I had these things and would probably see me in them as well. My mother picked out three bras and handed them to me to put with the panties. I looked at these new items. They had even more lace, but were mostly a sheer white fabric except for a tiny pastel flower nestled between the cups.
My mother walked over to the 'Young Miss' section with me in tow. She began scanning over racks of sundresses, occasionally taking one out and holding it up to me to see what she thought. She settled on two similar dresses in different sizes and handed them to me, then began looking over a rack of skirts. She picked out a couple blue skirts, then found a white blouse that she thought would pair well with it and handed a couple of those to me as well. Keeping quiet, I meekly accepted them and hoped we were getting close to being done. She looked at me and said, "OK, let's go see how they fit!"
My jaw dropped. I had thought it was bad enough to be out shopping for girl's clothing for me like this, but now she wanted me to try things on? I protested a bit. "But, can't we just get them and go?" I didn't want to be having to put a dress on in the fitting rooms of the department store.
"Absolutely not," she was adamant. "We really need to see how these fit on you, I've never bought clothes for any of you without having you try them on first, I'm not going to start now." She found a younger sales girl on the floor and asked, "Excuse me, where can he go try these on?" The girl looked at the dresses and skirts in my arms, then pointed to the women's rooms. "Yes, ma'am," she said, "you can go try them on in the fitting rooms."
"No," my mother corrected, "not me. These are for him." She pointed directly at me, emphasizing her point. "Not me. Still over there?"
The girl looked over at me, and at what I was holding. The realization of what was being asked hit her. "Yes, ma'am," she replied, "I'm sorry, I thought they were for you. If they're for him, he'll need to use the boy's fitting room." She pointed out where they were at, and noticed me blushing, head hung quietly. "Sorry, but it's company policy. We get men in here occasionally buying things like this. If they come in dressed as men, they have to use the men's room. If they come in and look and act like women, then they can use the women's," she explained.
My mother thanked the girl and walked me over to the boy's fitting rooms. "See," she said, "maybe we should have done your hair and makeup before doing this today. You're the one who decided to wear what you did, it wouldn't have been so much of an issue if you had worn the dress now, would it?" I didn't say anything as we walked up to the fitting rooms. "Here," she said, "give me your panties, go try on the dress first, and try at least one of the bras on as well."
I handed her the packages of panties and took the rest into the fitting room, hanging them all on the hook on the back of the door. I slipped off my sandals, and took my shorts and shirt off. I stood there, looking at the dresses, skirts, blouses, and bras hanging on the hook. I took a deep breath, and fumbled with getting the first bra off the hanger. Once I finally got it free, I slipped it up my arms and worked on hooking it behind my back. It took a couple minutes, but I was finally able to get it done. I slipped one of the sundresses off the hangers, and slipped it over my head. I looked at myself in the mirror, and called out to my mom, "This one fits!"
"Come let me see," she responded. I had dreaded her wanting to see. I didn't want to step out in the open wearing this, I was ready for the earth to open up and swallow me. "Come on," she insisted, growing impatient. I knew better than to try her patience, or she would really make things difficult and embarrassing. I opened the door, and stepped out to where she could look me over. I felt fortunate that there didn't seem to be anyone else around.
She looked me over, pulling the fabric of the dress up a bit and letting it fall, before rubbing her hand across my back. "You have one of the bras on?" she asked. I knew she could feel the strap of it, I just nodded as she pulled the strap slightly, testing the fit. Satisfied, she looked back at the dress. "This one's a little too big," she noted, then looked at the label. "Try the other one on, I think it will fit better around your waist and hips. It's good we're getting you panties as well, your regular underwear shows horrible lines under this." I walked back into the dressing room to change as directed. When I came back out, she again went over me, having me turn around. As I did, I noticed the sales girl off in the distance, craning her head slightly to get a look at me. My mother seemed satisfied, and I went back in with orders as to which blouse and skirt to try on first. The blouse took a little getting used to the buttons being on opposite sides, but once I came out and got looked over my mother seemed satisfied enough to send me back in to change into my regular clothes while the sales girl walked up.
"Those look really nice on him," she commented to my mother. "Any particular reason you're buying him them?"
My mother looked back at her and smiled. "He asked what it was like to be a girl, so we're letting him be a girl to find out for himself. He seems to like the clothes and told us he'd dress up if the clothes were there, so we're getting him clothes to dress in." The sales girl nodded her understanding.
"Well, when you're ready to go, let me know and I'll ring you up," she walked away as I came out with the clothes. My mother hung the clothes that she felt didn't fit on the rack to go back on the floor, chuckling slightly at just how out of place they looked, the yellow sundress, white blouse, and blue skirt hanging there next to the boy's slacks and button-down shirts. We walked back over to the 'Young Miss' section to continue shopping.
"I think we should get you at least one nightgown as well," she told me. She looked over the racks of summer-weight fabric and found one that she liked and held it up to me. "This should fit, what do you think of it?"
"It's fine," I said, eager to get this shopping trip done.
"Well, you're going to be the one wearing it, so you better be happy with it," she retorted. She looked around the area a little bit more, and her eyes settled on the bathing suits. "You're probably going to want to be in the pool a lot this summer, so we should get you a bathing suit as well," she indicated, walking over to the racks. She began flipping through the one piece suits, and I stood there quietly, looking around. My eyes settled on a red bikini with white trim on it. "What about this?" I asked my mother.
"I don't think you're ready for a bikini yet," she said, smiling. She found a red one piece suit that she liked, and added it to the pile of clothes in my arms. She found the sales girl who had helped us earlier, and we walked over to the cash register.
Ringing us up, the girl could only help but smile at all the things I was being bought. As she rang up the panties and bras, she asked, "Are you sure everything fits? We can't do returns on undergarments." My mom just smiled. "I had him try on one of the bras, and the panties are the same size as the ones he had on yesterday, so we should be fine," my mother answered.
The girl just nodded and looked over at me where I stood with my head hung down. "If it's anything to you, these things look really pretty on you," she remarked. "If you were to wear them in next time, you could use the girl's dressing rooms and not feel so out of place." She smiled sweetly at me, and I thanked her politely for the compliments, knowing my mother would berate me if I didn't. We paid, and carried the bag of clothes out to the car, my mother commenting that she wasn't the only one who thought I looked nice in a dress. She opened the trunk and I placed them in, turning to go get in. Instead she turned back towards the shops on the main street, urging me to follow. "Shoes next!" she smiled.
We walked into the shoe store, and my mother immediately went to the women's section to look things over. As she settled on a pair of low wedges, I found some sandals that I thought she might approve of to go with the sundress she had just bought me. As I pointed them out, she just smiled broadly at me, saying, "You really do have a good fashion sense, maybe you're more girl than boy." She went over and found a salesman and brought him over to where she had sat me down. "We need to get his feet measured and look at these shoes, please."
The salesman took my foot and placed it on the measurement tool. "Men's nine and a half," he proclaimed.
"That's fine," my mother agreed, "but do these come in men's sizes?" She held up the wedges and sandals for the salesman to see. It took a moment, and then he grabbed a different tool and placed my foot on it. "Women's ten and a half," he chuckled. My mother handed him the shoes and we sat there while he went in the back. I could hear a fair amount of laughter coming from the back, I just sat with my head down, knowing they were laughing at me. The sales man came back with the shoes, and handed them to my mother and I, together with a couple nylons to put on my feet while I tried them on.
The salesman chuckled as I tried walking around in the wedges, not having any practice with any sort of heels. My mother ended up being satisfied with both pair and we paid for them and started to leave. My mother was already out the door, and I was a few steps behind her carrying the bag with my shoes in it, when I overheard the salesman who helped us joking to another salesman.
"So," he asked, "do you think he's just some queer little faggot, or did he do something to piss momma off really bad?" As the door shut behind me, their laughter was the last thing I heard.