Chastity and orgasm denial discussion

Warning: It’s quite long, but I hope you all will enjoy it; we certainly did! Mistress and I live in Nor-Cal near a famous city known for its acceptance of various kinky lifestyles. There’s a specific bar that holds “Girls Night” about once a month where GGs can go unescorted, but GURLS (who must be fully dressed En-Femme) can attend if escorted by a real GG. We had been discussing spending a weekend in the city and going for ages. Now we finally did. Mistress decided that I would have to stay fully dressed En-Femme throughout the entire weekend and switch into my full Locked in Steel belt, wearing it for at least one month, possibly much longer. (We planned this around a period with no scheduled travel, obviously.) We booked a hotel and drove up on Friday afternoon after work—the traffic was terrible—but arrived there about 7:00 PM. Checked in, and I promptly dressed in what my mistress had chosen for me. It was a great retro outfit: a knee-length medium gray hobble skirt, a starched pleated white blouse with a lovely Peter Pan collar and circle pin, sheer black stockings, and six-inch black patent platform shoes. She also had me wear my largest breastforms along with a very pointy bullet bra to complete the look. Additionally, she decided I should wear something I have never worn out of the house before: a highly realistic latex female mask that I bought in Germany. It has real glass eyes, although they distort vision slightly because they are concave; stained red lips; realistic-looking eyebrows; and an opening mouth (since we were going to a bar!) where the latex curls around my natural ones. The drawback is that the latex tension tries to constantly pull my mouth open into an “O” shape. I used my favorite wig, long black Asian-style hair that I can back-brush into a half ponytail or create a pretty darn good Sarah Palin “updo.” Personally, I thought I looked great—a bit “out there” due to the hobble skirt, bra, and shoes, but otherwise very much like a 1940’s Gibson Girl. I was feeling really hot now, straining against my belt. My wife dressed as an English country lady with ultra-tight lycra riding britches (she does actually ride), a severe fitted blouse and blazer, four-inch stiletto heels, and black leather gloves. She brought her riding crop; it’s the real deal, not just some sex-store toy! We were quite a sight walking out of the hotel; we stopped a few couples in their tracks. We walked the four blocks to the bar, and the fun started. We grabbed two stools at the counter and ordered two single malt whiskies from a very nice-looking female bartender who seemed to be about 25+ years old. She served them, and when she saw me actually drinking while wearing the mask, she was fascinated. It turns out she is a masker wannabe and wanted to know all about it. I let her feel it, see how the eyes worked, how my mouth moved, described the feeling of being encased in latex, etc. She took my card and has since called to get our company name and URL. Good luck to her; she wants to mask as a Japanese woman. About five minutes later, a very large and tough-looking woman (it took both of us a while to decide if indeed she was a woman at all or just another gurl) came over, and the bartender introduced us. She turned out to be a regular, known by the bartender. She was very direct: Why would I dress as a woman and look like a sissy instead of an Alpha Male? She explained that she is an Alpha Female who likes dominating sissy men and submissive females. Wow. Now I’m feeling a little nervous. She had a body like a football linebacker, except for the huge boobs and leather corset with breast cups—you could pour a full bottle of wine into them without filling them; however, she did fill hers. This look was completed with skin-tight leather pants (she had a huge butt) and heeled boots. My Mistress now interjected and said two things: 1) He’s my property, and 2) You’ll be happy to know he’s wearing a chastity belt since he’s a gurl, not a man. The (I assume this is an assumption) dyke stopped dead in her tracks and said, “Way Cool! I gotta see that.” Mistress ordered me to stand up, unhooked my skirt waistband, and pulled it down right there at the bar. Everybody crowded around to look. Wow, was I humiliated. It got even worse. Mistress pulled out her riding crop and made me hold the bar rail while sticking my butt out. She cropped it about 15 times and handed the crop to the dyke. She gave permission for her to deliver 20 strokes. It hurt like hell, and I had to ask her for another after every stroke. The bartender got to do the same too. Both were laughing hysterically. The dyke kept rapping my belt and trying to see if it would come off or not. It didn’t. Her passing comment was: “I gotta get one of those for my Bitch.” Finally, everything calmed down, although my butt still hurt like hell, and all attention drifted toward the GGs who were chained together by the neck with about two feet of chain between them. An Italian-esque domme seemed to own them. We did meet a neat couple whom we had dinner with later; they were just like us. We compared chastity belts; he had a vintage Tollyboy that he’d worn for over 10 years (Yes, with periodic cleanings and one supervised orgasm per calendar quarter) and was very nice. Too bad he got cropped later by both his mistress and mine! He was dressed in the classic “Sissy Pink” ruffled dress and wished he could be more “formal,” as I was. I agreed with him. It was now late, so we walked back to the hotel. I got cropped at least 10 times (skirt on) when Mistress thought nobody was looking, just because she could and wanted to. We went to bed quickly, but not before I spanked Mistress over my knee, at her request. More about Saturday coming up later. This is already too long. Fun though.