Dressing, Meeting Friends (Part 2)

In preparation for the first get-together, I bought some makeup and the wig I'd worn for the makeover at Lee's. I packed the lingerie and shoes I had and headed to Bobbi's place.

Bobbi was clearly experienced at dressing, including in public, while I was nearly a novice. I borrowed some stuff he and Steve had and Steve took some photos. The ones here are the only ones I have left from that time (I don't think they're from our first session, actually, since the auburn pageboy I'm wearing is the wig I bought a month later.)

During this same period, I learned a little more about the "scene" and discovered the existence of professional dominatrices, women who specialized in humiliation and punishing men who got off on it. Many of them included forced cross-dressing as part of their services. I splurged and made an appointment with "Belle de Jour". At that first encounter, Belle dressed me in a maid's outfit, set me to work washing her undies, and then masturbated me to a climax. I was excited, but more by the whole secretness of the thing than anything else.

I also learned that Belle hosted a weekly "show" displaying her services and invited members of the audience to participate at the end. I began attending those shows about once a month, usually wearing my lingerie under my male clothes. When she invited the audience up, I would volunteer for a spanking, lowering my pants to reveal my panties, garter belt and stockings.

A few months later, Bobbi and Steve told me about a "club" they would be going to in Greenwich Village that had a TV night. (It was actually a local bar that rented space to the organizers.) Bobbi would be attending in drag and they asked if I wanted to come along. Having said "yes", I realized I'd need clothes...and Bobbi agreed to go on a shopping trip with me.

I'd done some surreptitious shopping outside of Lee's...learning I could buy stockings at Macy's--even talking to a clerk about them--without anyone raising an eyebrow, and getting shoes at another store's clearance basement. But I had no idea how to guess my sizes in blouses, skirts, or dresses, and trying them on in the store was out of the question. With Bobbi's help, I found a blouse, a knee-length denim skirt, and a dress. I decided to wear the skirt and blouse to the club, along with a pair of boots I borrowed from Bobbi.

I had one other surprise for Bobbi and Steve that night. I splurged again and bought a real corset at Lee's. I had actual curves! (I think I'm wearing the corset in these pix.) By then I had the auburn wig, too.

Still more to come on this phase of my life....