September 1st: I start back to school next week. Aunt Rose has gotten me a whole new wardrobe both for school and home. The school clothes are very nice but they make me look a little odd, I think. Some of the older boys looked at me strangely for a awhile but after a couple weeks they got over it. Maybe it was that they had never seen a boy with manners before who knew how to dress and look nice for school. She certainly had drilled all of that into me about how to conduct myself and how to dress and move and everything. Most of them certainly didn’t bother with themselves. A couple of them asked me if I had gone to a Catholic grade school because of my dressing and hair style. I just told them my aunt was very fashion conscious and strict. She certainly had taught me how to be a gentleman and I do mean with the accent on ‘gentle.’ My movements seemed different to me, somehow smoother, less abrupt and jerky, more fluid I guess you’d say like a dancer maybe. Perhaps even a little feminine but somehow, even thought that should have bothered me, it didn’t. This was a new school for me and the kids didn’t know the old, sloppy me. Those two inch heels made me walk a little differently too as I noticed that I had to sway my hips a little more although they were hard to notice as my slacks were just the right length. I liked the way my friend Janice walked in hers and I think I copied her walk.

Mostly my school clothing consisted of nice slacks in various patterns, fabrics and colors, a silk shirt in various colors and maybe a gold chain or two and a pair of loafers over thin, knee high hose. She never let me wear sneakers anymore. Maybe it was the earrings and long hair that put them off at first along with the gold bracelet and the smallish wrist watch. Well, they were earrings and even though they were a punishment, I had come to like them. Now I had two in the left ear and one in the right. I liked to see that little glint of light on them when I tossed my head or looked in the mirror. They had little diamonds that slid around on them as they moved. Aunt Rose had gotten me a few other styles and showed me how to put them in and take them out, even some pretty dangle ones. She told me the ones she put on me were self piercing and that’s why they hurt so much. And the wrist watch, well, a full sized men’s would look ridiculous on my tiny wrist anyway. I wasn’t any bigger than most of the girls in my class.

I had some really pretty studs now that I wore to school and several pairs of dangles that I wore at home. I don’t know why I let her talk me into those but they were very pretty and I loved the feel of them as they brushed my neck as they swung and I had seen dangles on some men on TV but I was a little afraid to wear them to school. It was really odd how my feelings about my appearance had changed since Aunt Rose had shown me the difference between slob and well groomed. Sometimes I’d even put my hair up so I could see them better although Aunt Rose preferred it down, cascading about my shoulders. I’m glad she cut in those bangs. I wouldn’t be able to see otherwise I think. One time, she saw me with my hair up in a pony tail and asked if I would like to try something else, a different way of putting it up. "Sure, why not?" I said. So she proceeded to teach me how to do a braid from my crown back. She told me I could tie it off with a scrunchy or a ribbon but to be honest the ribbon looked nicer. I remember that’s how the men used to do it in colonial days. So I started tying it up in all colors of ribbons to match what I was wearing on top. I had to admit, I did have pretty hair now. It was odd to think how I had come to think of my hair and feet as pretty. I did love the way that braid looked on me and had gotten used to wearing the dressier shoes.

A lot of the ‘at home’ clothes consisted of handsome tops that had a sort of self attached neck tie that was tied in a bow or that I could tie like a regular necktie. Auntie said they were the kind of top that 19th century poets used to wear. I’d wear slacks and a couple of them were designed so full that they actually looked like skirts I’m afraid. I think she called them Palatzo Pants or something. And unless I wore a somewhat higher built up heel, they dragged on the carpet. They sure had a lot of material in them and flowed all over the place when I walked. My newest sandals had a higher wedge heel with a single wide strap across my toes. I guess they must have been at least 3" high. They were cute. I felt a little guilty when I thought about painting my toes. I guess that was what wearing a long skirt felt like although I’d never had a skirt on in my life. Then that thought about what my legs would look like in a skirt crossed my mind. What is the matter with me? First I’m thinking lingerie and now a skirt and I’m enjoying 3" heels?

She got me some new night wear too, mostly nightshirt types, very silky and they came just below my knees except one that came all the way to my ankles and had long sleeves. It seemed to be a heavy satin. I thought that would come in handy in the winter. The fit was grand and loose and they hung somewhat from my chest as well as my shoulders. How strange. I thought my chest was flat but it seemed I was poking out some there along with my wider pelvis that seemed to force me to walk differently than I used to. No matter. At least they didn’t have pockets for breasts in them so I knew they couldn’t be girl’s nighties. Oh, they did have some pretty lace on them but Auntie pointed out that 19th century men wore a great deal of lace, a fact I knew to be true as I’d seen many pictures of them. They were very nice and I thanked her profusely because they felt so neat. She got me a nice quilted robe too.

October 1: Aunt Rose has been at me every day about how I sit and stand and walk and talk. It feels like she’s training me to become King or something, you know, Regal? I’m sure she only wants the best for me but she is at me about every nuance of my disposition lately. She wants me to sit down and rise slowly, gracefully, and not just plop into a chair and she wants me to stand with my feet together and cross my legs slowly at the knee when I sit or at worst, my ankles and to keep my knees together when I sit and arise. She won’t let me sit with my one ankle resting on my knee any more. Whatever could that matter when I was wearing pants? I could understand that if I wore skirts but I don’t.

She even made me carry a book around on my head for a whole week at home until my walk smoothed out with my high heels on. She said I was too ‘bouncy’, whatever that means. Said I’d never be able to be a waiter and carry a tray if I didn’t smooth out my walk. I really didn’t fancy becoming a waiter but I smoothed out the walk nonetheless as I realized that we may have guests and I might be the one serving them. Just to prove her point, she’d have me load up a complete service for one person on large platter with a drink and everything and take it to the table and back to the kitchen when we were done eating. You know, she was right. I had to learn to take a little smaller steps to but if I hadn’t smoothed out the walk and learned to move my hips gracefully, I’d have spilled the drinks every time. The trick was learning to keep my upper body quiet while I let my hips take up the balancing. This also caused me to learn to walk in smaller steps with my feet close together and more in a straight line.

She taught me the proper way to get in and out of a car too, placing my rump in first and swinging my legs in afterwards and then reversing it on exit. I never even knew there WAS a right or wrong way but that made it so easy, I wondered why I’d never thought of it myself. I suppose Mom and Dad would have shown me all this but they weren’t’ around now. She showed me how to take small bites instead of a mouthful, said it was bad etiquette to take such big bites as though I were a wolf devouring a carcass, and chew slowly and with my mouth shut. Now there’s something I never heard of before. I used to gulp everything down and just began to realize that I never really enjoyed my meals before. They were just necessary evils to be gotten over with as quickly as possible. But eating slowly and politely gave me time to really enjoy the meal and taste the food. Eating wasn’t such a bore anymore. It was time for small bites and conversation. She was teaching me how to socialize during a meal. It was rather fun not to just sit down to gobble and go.

I’ve been here six months now and I must be doing too much at home because my body is sore and despite all the work, I seem to be getting soft. My chest is tender and my slacks are getting pretty tight, so tight in fact that I’m a little uncomfortable in them, my underwear included. I really didn’t eat all that much and couldn’t understand why I’d be putting on weight, especially on my bum. I mentioned this to Aunt Rose and she came up with a solution.

She got me special underpants to wear that kept my boy things up and out of the way, not that it amounted to much lately, didn’t even seem to want to rise to the occasion but that garment certainly has made it easier for me to cross my legs at the knee and it gives me a nice smooth line in front. There’s no more bulge there to get in the way of crossing my legs and it’s ever so much more comfortable and looks nicer in all my slacks now too. The only problem with them is that I have to sit to pee since there’s no placket even if the slacks have a front zipper.

Well, I can get used to it I suppose except now I have to wipe in front as well as back as I was never well developed and now I appeared to be losing ground. My slacks are a size nine and when she got them for me, they were nice and loose. Now I more or less fill them completely although my waistline didn’t seem to expand along with everything else. If anything, it’s getting smaller. Well, what the heck. I’m not through growing yet, I’m sure.

October 31: Aunt Rose lives in a rather posh neighborhood and the young girl about my age a few houses up was having a Halloween party. She invited me either out of courtesy to Aunt Rose or because I was in her class, I don’t know which. I didn’t really have a costume but Aunt Rose came to the rescue again.

She borrowed an evening gown, did up my hair in a chignon and made my hair really pretty with beads wound into it and I wore matching long dangle earrings and full dramatic evening makeup too. She got me a pair of matching white pumps with 3 inch slender heels and taught me how to walk and dance in them for a few days before the party. I had always thought that slender high heels must be difficult to manage but was pleasantly surprised to find that these were quite comfortable and I really didn’t mind wearing them for an evening at all. I thought they made my feet look really sexy. My real problem was that I seemed to be rather enjoying these lovely garments and the way they made me feel. By the time the party came around, I suppose I had become rather expert at walking in them so as to not give myself away too soon. My new sandals were that high of course but they didn’t have so small a landing zone. I suppose it was just that the heel was so slender and feminine that worried me but my ankles soon adapted and the little soreness in my calves left too.

The day of the party, she gave me a manicure, shaping my now longer nails with very red polish and also a pedicure with matching polish. I couldn’t wait to see how my toes looked in my sandals now. It had been quite a while since I had cut my nails and wearing the rubber gloves had certainly kept them nice and strong, not to mention long. She shaped them just like a girl’s at least a ¼" beyond my finger tips and I can’t tell you how it felt to have such pretty hands and feet. It was weird how I reacted to this. It was just part of the costume of course, but it did give me a little thrill. Well, I want to tell you I was scared to death but turned out to be the belle of the ball. It was a blast.

I’d never really been popular and I’d never danced with a boy before and they didn’t have a clue as to who the fox in the gown was until the unmasking and then, they didn’t believe it. Let me rephrase that. They didn’t WANT to believe it! The boys were so embarrassed by some things they said to me in front of witnesses that I just knew I was going to be quite safe in school in spite of this little deception. They had lined up to dance with me and their reputations would be ruined if I spilled the beans on them. The attention was quite flattering and I’m afraid I rather enjoyed it. Naturally, I did my best pretense at being a real girl so as to pull off the masquerade successfully and was very apologetic to the boys for fooling them. I really played it to the hilt with the gentle voice and all. The girls were amazed at not only who I was but that I did such a wonderful job of fooling everybody. I had to admit that I really did make a passably pretty girl and the girls seemed to warm to me after the unmasking. I had never been popular but I was that night.

Auntie Rose and I had quite a discussion when I got home about how I had enjoyed myself and about all the boys I danced with. She seemed very pleased that I had such a good time. It was a great deal of fun although I must admit my emotions were somewhat on a roller coaster, feeling giggly and elated on one hand and a bit embarrassed on the other, first for having such a wonderful time being a girl for the evening and secondly, especially when in the arms of a big, strong, handsome, he-man type and feeling very submissive, like a real girl I suppose. It was rather easy to forget I was a boy when a big handsome guy was twirling me around the dance floor.