Part 5 of 29

Saturday, June 22
If I thought yesterday was weird, today about doubles the weirdness. We finished breakfast (sinfully late - 10AM!) and were relaxing over coffee. Grandpa went out to tell some lies with his cronies or something - he wasn't all that clear where he was going - and we were relaxing over coffee when Eve finally asked me about the crossdressing. As I fell asleep last night my mind cleared and I knew I wanted to take the next step.

"That's what we figured you'd say, which is why Earl decided he had something else to do this morning. He figured this would be easier for a woman to do - or maybe I should say he's just chicken. Earl is a sentimental old man; he couldn't bring himself to throw out any of Sylvia's clothes when she died so they're all in the spare room. She was large for woman and some of her things might fit you.

She was right, the closet was almost full of clothing, neatly covered with plastic to protect it. Eve removed the cover and moved things around a bit.

"They may be a bit out of style but Sylvia had good taste and I'm sure you won't mind too much. I don't want to be morbid about this, but Sylvia was my best friend. Before the cancer got her it took her breasts and she lost her hair. If you look in the small box in the bottom drawer you'll find a pair of breast forms and there are several wigs in the closet. I washed everything after she died and put them away so if you feel comfortable about it they're yours.

"I can't say she would have wanted you to have them because as far as I know she never knew anyone who crossdressed, but she was a generous woman who always did her best for her friends. Maybe Earl had a premonition that the clothes would be needed, he's like that sometimes. We won't be back until suppertime so you have all day to yourselves."

A quick hug and she was gone. I just stood there, looking at Mary Ann, not quite sure what to do. I hadn't bargained for this. I couldn't help thinking of how I wrote 'the Lord will provide' last night. I don't think Dad would want to use this as an illustration in a sermon, but suddenly my unspoken prayer had been granted.

"Are you OK with this? After all she was your grandmother." I had to ask.

"I never really knew her, she died when I was pretty young. I mostly remember her from the pictures we have. It does seem a little creepy, after all she's dead. I love you, Angel. If this can make you happy then it makes me happy. Go ahead and open a box."

She loves me? Yeah, she said it. I've been thinking those words, writing them in this diary, but I haven't had the nerve to say it to her.

"I love you too, Mary Ann. I don't know why you put up with me and my weird obsessions, but thank God you do!"

"God ain't got anything to do with it, silly. Now open one of those boxes and let's see what's in them."

I'm not so sure that God isn't part of this, but I wasn't going to argue theology with her. It may sound funny, but after saying 'I Love You' out loud to her I wasn't quite as interested in looking at the boxes, but when she shoved one into my hands what choice did I have?

The first one was disappointing - socks and shorts not too different from what I always wear. The next one was hardly better, t-shirts. I was starting to wonder if I was going to find anything I wanted to wear.

I shouldn't have worried. The next box held bras and panties by the dozens. I picked up the one on top and examined it. Just a plain, white bra but it looked like it might fit. With a shrug I took off my clothes and slipped my hands through the straps invited Mary Ann to do the honors. She snapped the back and it fit! By then I was starting to get excited, I went to the dresser and sure enough there was a little box in the bottom drawer. I opened it and took out the breast forms.

They wiggled in my hands, almost as if they were alive. They were cool to the touch but warmed almost magically as I held them. I pulled open the cup of the bra I was wearing and dropped one in. A bounce or two and it settled in place, so I inserted the other one.

I couldn't believe how right it felt! Wearing a bra stuffed with washcloths had been fun, but once the breast forms were in place it was a whole new experience. Mary Ann helped adjust the straps and I could feel their tug on my shoulders. The bra stayed in place by itself, it didn't try to slide up to my chin like it did before. My balance changed just a little bit, I had to lean back ever so slightly to balance the weight on my chest, which made me feel remarkably feminine.

Mary Ann laughed delightedly as I went through all this. I had to look in the mirror, which made her laugh all the harder. I guess I did look pretty silly with a brush cut and the wrong equipment hanging between my legs.

"Try on the panties, silly woman!"

Woman? Well, I guess she had a point. The panties were pretty loose, I don't have a woman's hips. We solved that with a safety pin. She circled around me like an artist examining her creation - well, maybe there was some merit to that - and informed me I had to shave.

My legs.

I don't have much body hair, but the mirror my legs looked fuzzy enough to spoil the look of the bra and panties as much as my brush cut did. I kind of liked the idea of shaving my legs. Running my hands over Mary Ann's smooth legs was a pleasure, so why not shave mine? I started for the bathroom immediately.

"Angel, take off the clothes, you dope!"

Oh. I guess I was a little too excited. We filled the tub and I climbed in. She handed me the shaving cream and I awkwardly spread it on my leg. I used her razor (mine got used about once a week - on my face) and found it takes acrobatic talent to get at the back of your legs.

It took a lot of time, the razor kept clogging. Mary Ann assured me that once I had shaved it would be a whole lot easier to keep it up than it was to start.

We went back to the spare room and this time I picked out a prettier bra, a white one with lacy cups. I like lacy cups, they look so great through a blouse. There were even some pantyhose still in their packages, but they didn't quite make it up my legs, I must be taller than Sylvia was. I wore them anyway. The shoes were hopeless, I had to settle for my own sandals.

I was dying to look in the closet by then. A very frilly blue dress with a low neckline caught my eye. I tried it on and it felt wonderful! The skirt drifted across my shaved legs like feathers. I was in love! I was in Heaven!

Then I caught Mary Ann's look. I was in trouble! She was laughing and pointing to my chest, er… breasts. So I looked in the mirror and saw my few chest hairs and the edges of the breast forms clearly visible. My fantasies came crashing down in a moment.

"I think you need to wear something with a higher neckline, don't you?"

Spoilsport! I took off the dress and hung it up, selecting a bright red high collared blouse. This one had lots of frills at the neck and cuffs but I hadn't even gotten it out of the closet before Mary Ann vetoed it, too. I was getting frustrated!

"Look at me, darling. What am I wearing?"

"A blue blouse and a white skirt?"

"Right, Describe them to me."

"Uh - the blouse is pretty basic, light blue cotton blend, wide neckline, short sleeves, and it doesn't show enough of your pretty tits. The skirt cotton blend, too, I think. White, elastic waist, simply pleated and it shows your knees very nicely."

"Not bad for a novice woman, where did you learn about fabrics? Never mind that, what would you expect a woman to be doing in an outfit like this?"

"Shopping, visiting friends, casual stuff, right?"

"Right! Now, what would a woman be doing when she wore that blouse?"

I got the point. That was a party blouse, formal and flashy. It would look out of place anywhere else. I got my first lesson in proper dressing from Mary Ann that morning. She selected a white cotton shell and a pretty flowered skirt for me, summery and simple. I tried on the three wigs and was amazed at the difference they made. With longer hair instead of a brush cut I really did look like a girl.

I've always liked longer hair on girls, the shorter styles just seem wrong for some reason. OK, the reason is that my father felt that women should have long hair. No matter what happens, no matter how much I reject his religion or outmoded ideas, he is still a profound influence on me. I'm starting to understand that passage in the Bible about things being passed on unto the third generation. I sometimes worry just what I will pass on to our children.

After trying on the wigs, we decided I looked best in the page boy, it softened the lines of my face and I liked the feel of hair on my neck.

We moved some of the lingerie into our bedroom and packed up the boxes neatly with what I didn't use. We just hung out the rest of the day. We made lunch together, everything seemed new and special because I was wearing a skirt! The closer it came to 5 o'clock, the more nervous I became and finally I returned to the bedroom and changed back into my regular clothes.

Mary Ann didn't say anything, she understood I wasn't ready to have Grandpa see me like this. It was a beautiful day, one of the most special in my life!
 

Tuesday, June 25
I wore Sylvia's clothes all day today and even cooked dinner with Mary Ann while wearing them. I did chicken out and change before Grandpa and Eve got back though.

I could really get to like wearing these clothes all the time.
 

Wednesday, June 26
I wouldn't have believed it, but after only three days I was getting bored. Oh, not with getting dressed up - not by a long shot. Each morning when Grandpa and Eve left I rushed into the spare bedroom and put on my pretty clothes. Mary Ann is a gem, she must understand me because she gently reminds me of how a woman moves or speaks. She's teaching me how pick out matching clothes, how to use makeup (tricky stuff!) and only laughs at me once in a while.

It's the staying in the house that is getting boring. Sure we can watch TV or read or play with the computers, but I was torn. It was a beautiful day, I wanted to go out but I didn't want to take off my wonderful new clothes. Naturally Mary Ann had the answer.

"So let's go out and take a walk, silly!"

I think my name is getting changed from 'Angel' to 'Silly' for all she uses it. Just open the door and go out, right! I was scared. Dressing up was fun, more exciting than anything else except learning to love Mary Ann, but I was just plain scared to let anyone else see me this way. It took me quite a while for her talk me into it. In the end she just took the money out of my wallet, put it in a purse and handed it to me. She picked up her own purse and walked out the front door, leaving me to decide what to do in a hurry.

I went.

And I survived. How wonderful is that?
 

Thursday, June 27
How is it when I read stories about having beautiful shaved legs nobody mentions that a few days after shaving you have stubbly porcupine legs? I never felt Mary Ann's legs be stubbly, but when I asked she said that's because she keeps shaving them.

Duh!

I have a lot more leg than I have chin. Being a lady isn't all bubble bath and perfume, I guess.
 

Friday, June 28
We went shopping today. I got some panties and pantyhose that fit me properly. I enjoyed Wednesday's walk, but with the too small pantyhose I was glad to get home. We rode the bus and no one even looked at me, which is one of the advantages of being with Mary Ann. No one looks at me while she's around.

I kind of missed holding her hand on the bus, but I sure didn't want to draw attention to us. I learned about window shopping that day, we didn't buy much (no money!) but we looked at everything and I even tried on an outfit at the K-mart! I didn't get it but I was able to put on the new pantyhose and I felt a lot better walking after that.

Mary Ann introduced me to Shoe Source and I got a pair of flats that felt more comfortable than my sandals, or am I just thinking that because they are girl's shoes? I don't really care!

The other great adventure was having to pee. By the time we were ready for lunch I knew I wasn't going to make it home so I had to use the ladies room. We picked a Burger King for lunch because they have one person restrooms. I got in and out and no one noticed!

Is there a ladylike way to eat a Whopper? Next time I'll pick something smaller, I felt foolish trying to stuff that big burger in my face while acting like a lady.

Maybe that's why those two girls spent so much time looking at us. If I were in my boy clothes I might have spent a bit of time appreciating them, at least if Mary Ann wasn't around, but it was uncomfortable being stared at like that. What would I have done if they were guys? Not a thought I want to dwell on.

We were having so much fun we lost track of time. It was late when we got home and both cars were in the driveway. No chance of sneaking in and changing, but after spending the day out in public I felt pretty sure of myself. I just hoped Grandpa and Eve would be OK.

I took the door key out of my purse and opened the door. We walked into the kitchen and Mary Ann said "Hi, Grandpa!" He turned and did a double take that warmed my heart. Not often you can get the best of the president of the Liar's Club.

"I will be damned! Hey Eve, get in here!"

She entered the kitchen serenely, not at all disturbed by Grandpa's excited shout. No double take from her, just a warm hug and a kiss for the both of us.

"Earl, what's all the excitement? I'm glad Mary Ann and Angel are back but you don't have to shout."

Grandpa is lucky she isn't interested in running for President against him, he'd have some stiff competition with her poker face.