A day full of sissy dress-up and lingerie.

Sissy dress-up adventures. It was time to give my little sissy pet a treat for being so loyal and devoted to dressing up. He spends a day in and day out, living like a perfect, feminized sissy. Her name is now Jane. I taught Jane how to do her make-up at first, and later she put even more devotion into it and bought herself a few lessons with a licensed cosmetologist! She even crafted a sissy shopping list for us to go purchase together. It turned into a day-long shopping adventure. She knew exactly what she needed to wear to impress. Of course, she spent plenty of time researching and watching some drag shows and youtube tutorials.

Now, the time had come to tell Jane why she was doing so much shopping! She had been putting a lot of work into herself, so I decided to reward her. Honestly, she loved the thrill of going on adventures with me and going on bar crawls. It was all about meeting new guys and getting to flirt with them while passing off as a girl. So, I went around and set her up on a little blind date. Unbeknownst to her, I found a guy who was exactly what she was looking for. He was tall, tan, handsome, and very fit. I found her a Greek God of a man, basically, and a gym trainer too. So he would be able to help her work on the figure she worked so adamantly to maintain.

He was the perfect date.

And Jane was going to meet him all dolled up, full-blown sissy dress-up, and ready to fuck! But first, we needed to buy her a sexy outfit worthy of a wild first-night-fuck. The first thing we set out to buy was some lingerie. I took Jane to Victoria’s Secret and paraded her through the halls of the store.  The sales assistants watched and wondered, but I think they knew what Jane really was. They giggled among themselves as I picked out a little black lace corset for Jane. She blushed bright pink but continued shopping. After all, she kind of loves it when people giggle and realize she’s crossdressing. It all excited her even more so.

Finally, we took a stop at the fitting rooms. Jane hauled in all her sexy, delicate lingerie outfits. Of course, she picked out more than she really needed, but she wanted variety back in her wardrobe. One by one, she tried them on, checking herself out in the mirror and sweeping the door open. She strutted out in heels in lingerie like it was a sissy dress-up movie montage. I giggled and took pictures of her, all to send them off to her soon-to-be date. The store was full of people, ranging from girls to older women to their tag-along boyfriends. Even the guys couldn’t help but stare and peek in at the commotion in the fitting rooms. It was like every fetish phone sex fantasy Jane had ever had.

She was finally ready to go.

We picked out the lingerie, some stiletto heels, and a tight little dress that fit her figure perfectly. The black strapless lace corset that she wore peeked out just enough at the cleavage. Everything was set and done, so I sent Jane off to her date! He couldn’t keep his eyes off her physique; all dolled up in her sissy dress-up outfit. She donned red lips and a matching manicure and set off to do the job. What she didn’t know was that her date, Alex, was more than ready to meet up and fuck. Nearly right after they first meet, he took her home, and of course, I tagged along as part of our deal.

Alex pulled Jane, my little sissy dress-up bitch, onto the bed and yanked her skirt up. He bent her over it and spanked her ass, showing off her little bulge and the tight ass he’d be fucking all night. I sat by, sipping on a little drink I mixed up, taking pictures and recording them all night long. It was a night to remember. That night, Jane showed her sissy whore colors. It was the night she finally got ass-fucked by a bull I hired for her.

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