Wannabe Sissy Leah Comes to Visit: Part 1

Here is shy little Leah, a mature retired widower from western Pennsylvania. She had never been fully feminized, she said. Just panties and stockings and an occasional silky nightgown. Her pleasure in wearing women’s clothes started in childhood, but was kept on a slow simmer for decades, throughout a long marriage and several subsequent girlfriends.

Dating was tricky and tedious and expensive. She fantasized often of what fun it would be to play and explore en femme with a dominant woman, but finding someone through Match.com and OKC was difficult. And she didn’t want a “mean, scary domme in a dungeon” (her words, not mine, BTW—some of my most treasured friends are dommes in dungeons, and I enjoy that environment, too)

Anyway, Leah did a very smart thing. Instead of  continuing to struggle inside… instead of settling for recordings and phone domination…  instead of letting that dream die inside her… she came to me. I’m so glad she did. And so is she!

After we removed all her male accouterments, I let her choose some brand-new panties from my collection for her own. Her choice was sooo Leah… pink and flowery, with full coverage front and back. (She was rather timid at first in that regard.) Then I added a delicate white lace boy short over it.

My feet couldn’t resist the delicious combination of textures and colors, or poking around dear Leah’s dainty bits to monitor what was happening under the lace and flowers. I asked for a foot massage, and she surprised me with world-class skills! Her reward was to bathe my feet with her tongue. And once again, she impressed me—instead of diving for my toes like a hungry bass,  she first politely pulled a towel from her bag to wipe away any drool. What manners! What forethought! I think she’d been a Boy Scout… proactive and always prepared.

I loved the foot worship and melted into the couch. Leah couldn’t hide that she liked it, too. A LOT. Too much. (Leah may have a date with a chastity device in the near future.)

Leah has potential to make a truly fine sissy, but she does need training.

It was important for me to take her mind off of her clitty and help her learn to keep it better under wraps. So I pulled down those lovely panties, bent her over the dining room chair, and applied a hand spanking and the cane—while deciding whether to make her into a maid or a slut….

Read Part 2