Nana's Diary Ch. 03

A trip to the mall

Author's Note: this chapter has no sex but was needed for story clarification.

Tom's comment that he was "not much of a man" stuck with me and made me think, that if he were not much of a man, he should learn to be more like a woman. When Tom returned from work, I told him to go into the bathroom and remove all the hair on his body except for a small landing patch above his tiny prick. Make sure that he shaved under his pits and get those little hairs out of his ass. About an hour later he emerged from the bathroom as smooth as a baby. I told him that if we were going to please a woman, he had to know more about what it was like to be one.

I had him sit down in front of my vanity and taught him how to apply his makeup. With instruction, he put on foundation and blush, but needed help with the eye shadow and liner, unable to draw a straight line with his shaking hand. Despite his supposed discomfort, His little clit was at attention through it all. My goal was to make him passable but a little slutty. I told him to remember what he did because he would have to do it again soon. But not Saturday when I planned on taking him shopping. Although I was horny, and could use a good orgasm, I told him to stand in front of the mirror and think of how he would please me; not as a man but as a woman.

Saturday rolled around quickly, and we were off to the mall. I told Tom we would start our day by getting a mani/pedi. I had Anna, my manicurist, put clear polish on his fingernails, but had her paint his toes hot pink. She just looked up at me and smiled as she finished his toes.

Our next stop was Macy's. Their intimate selection is quite complete, and it was more likely that we would be helped by an older woman than a young girl. There would be plenty young girls to work with later. I had Tom ask the salesperson Helen help in buying panties. Helen asked him what size his wife was. He responded as directed "There not for her there for me".

Without missing a beat, Helen looked down at him and said, "you do not have much of a package there, these smalls should fit you fine." How many pairs do you need? Tom responded a dozen and I prefer that they be lacy and come in a variety of colors.

I could see he was turning red as the panties he held in his hand, but I minded him no matter. Helen, then asked if there was anything else. He responded that he needed a half dozen bras to match. What size?

He responded 38C. She asked if he was sure he needed such a big cup and he just nodded. Ready to check out, Helen once again asked will there be anything else? Exasperated, Tom said I need some garter belts and some hose. Please make sure at least one pair is in pink. Helen then held up a few belts from which Tom could choose and decided to go with one in basic black and the other in pink. Tom paid, thanked Helen for her help, and then joined me as I waited in the dress department

I told Tom that I thought he made some good selections and that I could hardly wait for him to model for me. I said let's go somewhere else for skirts and dresses. The clothes here are just too conservative and matronly. Back in the mall we walked past Forever 21. Let's shop here. Tom was mortified. Not only were the clothes young for me, much less him, but the store was crowded with young women.

Trying to distract me Tom asked isn't this where your granddaughter Kim shops? And I said yes it will be fun! As we looked through the racks, I found this really sexy short pink skirt that would require you to cross your legs carefully if you didn't want a guy to have a perfect view to your panties. I held it up to Tom and it came to about four inches above his knee.

Don't you just love this I said. Yes, he replied. I turned to the salesgirl Rita, who had approached to help, and asked her if she had this in an 8. An 8 would be way too big for you. Oh, it's not for me, it's for him.

Rita said shut up? No, it's really for him. Is he a cross-dresser she asked? No, it's just that he has a really small dick and that dressing him as a woman helps remind him of that. Tom was so embarrassed he wanted to disappear. Well yes, I have this in an 8. What else can I help you with.

He needs a little black dress, more miniskirts, and a corset in 38c if you have one. No problem, I will meet you at the register. As Tom pulled out his card to pay I asked Rita for her personal email. I told her that I thought she had a lot in common with my granddaughter and that they would both appreciate seeing Tom dressed up.

We stopped at the food court to get a drink and I asked Tom what he thought of our purchases so far. He said that he had tried on women's panties before but had never put on a skirt. I responded by telling him how empowering it was to be able to control a man by what you wore and that one day he will know what I meant.

We still had a few more stops to make. We went to Claire's and Tom tried on some clip-on hoop earrings, Laura, the salesgirl was a little shocked but after giggling for a few minutes and talking to the other associate Julie, recommended a few pair of drop earrings that would highlight his features.

Again, before leaving I made sure to get the girl's email addresses.

After Claire's we went to the wig store. I had Tom try on different styles from a pageboy, to a bob, but settled on a brown wave that went to his shoulders and that he could tuck behind his ears if he wanted to show off his new earrings

Our last stop at the mall was DSW. Tom has very small feet and wore 7.5 size men's shoes. Using a quick conversion table, I found on-line, we bought size 9 women's; the shoes fit perfectly. He bought a pair of 4-inch heels in black to go with his new black dress, a pair of 3 inch sandals to display his pink toes and a pair of nude heels to go with the rest of his wardrobe.

When we got home, I told Tom we would have a fashion show sometime soon but I wanted to wait until he was again made up. I did instruct him to practice walking in the heels because he would be serving my book club as a maid next week. I also told him that when he was dressed as a woman, he was to respond to the name Tia.