Shopping with Trudy

As many of you know I have more than one “alter ego”. April has many looks, and over the past 19 months I have been going out with more frequency.

Yesterday I went shopping with my friend Trudy. Trudy is an attorney who recently went through some plastic surgery. I must say she looks great and she is happier than I have even seen her.

Trudy is an excellent attorney, but she also has OCD, which manifests itself in many ways. For example, she checks her lipstick every 5 minutes; she changes her underwear 4 or 5 times a day.

She asked me if April might like to spend Saturday shopping with her, and not surprisingly I said yes. As a “normal” gal I am very passable. I know all of us gals think this, but I really am. I have no beard left, I am smallish, small feet and hands etc. It is hard for me to tone down my look, but I manage. I have found one can wear great gobs of makeup if one is conservative. So no false eyelashes on Saturday morning! But based on where we were going I did wear a girdle and stockings, always a bit risky.

Trudy picked me up on a warm fall Saturday morning, and we headed to a mall about 20 miles from me. I must say, I had the time of my life! We started with shoes at Lord and Taylor, and I got 2 pairs, Trudy 3. We had a funny moment as she saw the heel and toe of my Hanes 415’s, in “South Pacific”. Clothing was next. I have been trying to get her away from her business suits she wore everyday, including this shopping trip. We each picked a few things, and I went to go into my own dressing room she simply followed me. Just two gals out and about. In a moment our clothing was off. I had a lovely slip on of course, and she helped me into a dress I ended up buying. She suddenly stripped to nothing and put on a clean bra, panties and her ever present Hanes support hose. She tried on 4 outfits and a dress, and she got all of them! I cannot describe how wonderful this felt to me, it was amazing.

This mall is huge, and off we went next to Macy’s. More shoes, more dresses. I took her to Bebe, and she got the sexiest skin tight black dress. I must say also the young ladies working there were amazing. Then Nordstrom, where we both got Nars lipstick.

We stopped for lunch at the huge food court, and then I needed to pee. I know the “unisex” toilets at this mall, but Trudy wouldn’t hear of it. We went back into Lord and Taylor into the ladies room into the handicapped stall! While we have not been intimate, Trudy knows everything about me. But as always I had a Modess hospital size pad on.

“Come on hurry up” she said when I hesitated. So I lifted my dress and slip, down came my girdle, stockings, pantyhose and panties. I reached behind me and unfastened the pad, then took it off from the front. I sat to pee and she giggled.

“I guess I shouldn’t be surprised you sit down to pee, but I wasn’t expecting it.” she said laughing. “And it really is small isn’t it?”.

I finished going, decided not to change my tampon, and got another napkin out of my purse. Once it was her turn she dropped her skirt, pulled down her hose and panties, and sat to pee. I don’t know about you but I love the sound of a woman peeing. Once again she changed everything, and when we finally left the stall, we both spent 10 minutes touching up makeup. You see what originally attracted to her was her heavy makeup, covering up adolescent acne scars. I was afraid that after she had this address, along with a new nose, eyelift and lip enhancement, she would stop wearing it, but as always her foundation was thicker than mine. She had that wonderful smell of makeup and perfume.

We left the mall, and the ride home was interesting. She asked those questions women ask us always, why, are you gay, do you want a sex change. I have known her for a few years and we never talked about these things.

She came in for a late afternoon glass of white wine. But there was one more surprise. “So you enjoying getting and enema don’t you?”.

“Yes” I answered truthfully.

“Maybe next time I come over you will show me? “she asked.

Guess what I answered?