I met my ex through my Domme. Well, she Domme’d us both for a few years. However, following a night out at the club where we laughed our asses off until they put us out, my ex and I started dating. As you’ll recall from one previous story, I was considered by some a late bloomer sexually because my sexual exploration excluded the penetrative kind. So, he and I had a lot of firsts together and this story is about one of them. This particular first involved an afternoon of expansive Easter exploration.

Expansive Easter Exploration

My tale of expansive Easter exploration starts on a muggy, partially cloudy Easter late in the morning. My (now ex but at that time) partner had asked that I come over for brunch that day because there was someone special, he wanted me to meet. He told me not to worry about dressing up since he had an outfit picked out for me (not abnormal for us, especially since my partner’s style is impeccable) but to arrive early so he could help me get ready before she made her appearance. When I got to his place, he was still wearing his bathrobe and the house smelled glorious. He directed me to hang my own coat up and meet him in his bedroom while he took some things out of the oven. Upon entering his bedroom, I saw that there were two sets of clothing laid out on the bed and immediately went to sort through the set of clothing that included high end shapewear, a dress, and hosiery. He finally made it to the bedroom and instead of getting dressed, he leaned back against his dresser and watched me…waiting. Confused as well as irritated, I stopped getting dressed to ask him, ‘What?’ He pressed a finger to his lips thoughtfully, before standing up fully, ‘This is my fault. I should’ve told you.’

Confessions and Crossdressin’

He placed his hands on my shoulders as if to draw attention to the fact that the dress was clearly too big for me. He helped me out of the dress and turned me around, so my back was to him. He asked me to hand him the shapewear that had been lying on top of the dress. When I did, he disrobed and stepped into the shapewear before pulling them up over his hips. He carefully tucked himself into them so that the crotch would lie (mostly) flat. His usually hard, muscular body was softened and curved at the hips and before I knew it, I felt myself blushing. After putting on the bra that was lying on the bed, I noticed that the cups were not only padded but the bra size was perfect. I helped him zip up his dress, an airy floral number, following the adjustment of his flesh toned control top pantyhose. He sat down on the end of his bed, taking my hands in his, and asked what I was thinking. ‘Nothing. I just feel a little silly. The dress didn’t even fit and those undergarments…?’ we looked at each other and immediately started laughing. ‘Don’t get me wrong, they look great on you, but I should’ve-‘ he pulled me onto his lap and reassured me that I hadn’t made him feel anything but amused. He took a few minutes to fully explain what he was trying to show me but once my reassurance was secured, he asked if he could help me get ready.

Mimosas with ‘Janet’

After learning how to properly tie a half Windsor and falling in love with menswear all over again, I helped my partner put the finishing touches on ‘Janet’. As I was finishing her hair, ‘she’ asked me to be a dear and pour us a Grand Marnier mimosa. While I was preparing the drinks she imparted her extensive knowledge of blush application to me, along with her controversial opinions regarding men’s facial hair. Janet was a real blast in a glass, and I was curious as to why she made such rare appearances. She informed me that she was more of ‘Limited Time Diva’ and only appeared when the atmosphere was festive and ripe for merrymaking with someone special. She complimented me several times, saying I was just the kind of ‘man’ she envisioned and asked if I’d be interested in seeing her in a more ‘physical’ capacity. Surprised, I let her know I was definitely open to more exploration. ‘Then it’s a date!’ she said, enthusiastically. We talked for hours. Mainly her answering my questions about her shapewear and which were better in her opinion: stockings or pantyhose? Then, we finally enjoyed the amazing lunch my partner had prepared. We agreed to meet up again soon before clearing the table together and I changed my clothes. and she saw me off promising to have my partner call me, ‘Around 7 tonight.’ I left as the sun was setting along with the realization that my partner was a crossdresser and a desire to understand what exactly it’d stirred up in me.

If you made it this far, Thank you so much for reading!

Also,

Happy concurrent holidays, horny peeps! To all you Easter celebrants, I hope you get something sweet in your Easter baskets and that your feast/dinner is an indulgent, sensory experience. For all my fellow subversives, enjoy getting the wind during your walks in nature today.

Yours Indulgently,

Your Midnight Masturbatrix

Goddess Meshelle

P.S.

This is just the tip of the iceberg in terms of expansive exploration. Tune in to Whore School tonight at 11pm EST where I’ll be discussing the consciousness expanding topic of Sexuality with Ms. Harper

P.S.S-

Check back here around this time next month. You’ll be really glad you did!