Diary Entry: Sissy Shopping and Thoughts

During part of the training, there is shopping that happens. That seems like a ‘DUH’ kind of expectation – but, with a new sissy you, you need a new sissy wardrobe.

Here was the diary submission for that week


The shoes from Yandy didn’t ship with the rest of the items Mistress Lillith assigned me to buy.

They were to come separately but there wasn’t a tracking number. I contacted customer support with the order number and inquired. A customer service rep named Linda, who had a girl in lingerie for her profile picture, emailed me an apology:

“Robert, the tracking number for *your shoes* is…” Size 10. My shoes. A thong string bikini and leather and chains were the other part of the order.

Kind of humiliating.

A review on Yandy.com for the leather and chains outfit was from a guy: “My wife looks great in this.”

Uggghhh… Super humiliating.

I asked Mistress Lillith for a little more time on this week’s assignment. She agreed immediately. I wanted to tease her as a pushover but didn’t have the nerve. I guess I did here.

I wonder if she’ll really push me and my boundaries. This is already as far as I’ve gone. I think I could probably cum just thinking about intense pyschological domination… Being told

“No. Get it done bitch.”

Yep that would make me cum.

This was a crazy week at work. A really positive, memorable one. But still one that sucked up everything from me. I wasn’t sure I could juggle everything I had going on. By some fortuitous circumstance I found myself alone for an hour. I could hardly believe it. “Okay, now or who knows when.” I thought.

Need to shave. Foundation. Eye shadow. Damn I messed it up again. Pink blush. That looks better. Hot “cocksucker” red lip stick. Mascara. 20 mins in. Makeup takes forever.

Slave 4 u by Brittany Spears played in the background and her music video was on my TV. I fumbled as I tied a string bikini for the first time. It didn’t cover anything downstairs! I set my cell phone up to record and walked, posed.

Next outfit: the leather and chains one. Oh my gosh. I kneeled. I got on my hands and knees. Whoops my balls made it in the shot. Now the black dress.

Stress was washing away somehow.

45 mins in. Time is getting tight, need to clean up. Rushing. Double, triple checking things–yes, all put away. Unbelievably I finished, mostly. Still have my shoes and cutoffs that haven’t arrived yet.

My body hair is growing back slowly. I really like my nude skin better than being a wookie. Waxing is expensive and painful but who knows. I have a week or three to think more about it.

I missed my mantras twice this week. Just completely forgot. I’ve tried to make up the time here and there.

I had a sissy dream on Monday.

These are RARE for me. In it my hands and legs were bound in purple blocks. My headphones were on and I was being forced to listen my sissy slut mantras.

Work meetings have been different too. I’m admiring women’s makeup and how they do their hair. That’s NEW.

I’m tired and still having fun.

Now you know why women are sometimes exhausted. It’s a lot of work looking so perfect! 😉

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