Sherry’s Excellent Adventures

By Sherry Greer

It’s been a few weeks since I have written about my adventures. I have had a busy couple of weeks (not Kandi busy) to get out as Sherry and like always, I encountered some firsts! A couple of years ago I had the opportunity to meet Kandi at the Men’s Chorus gala that she volunteers for (it was the first time I wore a dress in public) and I have wanted to go back ever since. This year was the year so I texted Kandi saying I could volunteer and of course she put me to work helping with the silent auction and wine ring toss game!

The people that I worked with were amazing! Prior to the evening I went out to buy some needed items. Since this was a Carnaval theme, I bought a lacy and ruffled top and skirt to give me that Latin flare. All of the stores I visited I portrayed a confident, and I hope, convincing woman. (You have already seen the pictures that Kandi posted from the event.)

The day of the event I made arrangements at a local Sephora to get a makeover. I needed some new foundation and a few other things so I easily spent the needed $50 to get the makeover for “free”. I went to Sephora in skinny jeans, a camisole top, fly away sweater, booties, no makeup, and my real grey hair in a ponytail with a hairpiece. I again was confident! I enjoyed myself getting pampered and talking with the makeup artist the entire time. As always, no issues. The male, heterosexual manager even came over a couple of times to see how we were doing and even asked what the occasion was for getting a makeover.

I then visited Gina at my favorite salon to get my long black wig styled in a tight bun and bought some flowers to accessorize the look. She was extremely happy with the job she did on my hair and so was I. This was the first time I ever wore the black wig and had a theme to my outfit. I absolutely LOVED the earrings I bought to tie everything together.

The evening was fabulous and I met many lovely and caring people. I received many compliments on my outfit and hair. My wife knew about the evening and asked if I would be home by midnight so I definitely wanted to make sure I was home on time. She has come a long way so I need to be considerate of her wishes. I did help with some of the cleanup but then left to use a hotel room that a friend and her wife got for the night. It was an adventure walking from the parking lot in my 4″ heels while carrying 2 bags and my purse to the busy downtown hotel! As I was getting on the elevator Lindsay, a friend of mine and Kandi’s, was getting off so we hugged and chatted briefly. I made it home on time so my wife was happy. Whew!! The next day my wife asked how everything went and I gave her a brief synopsis of the evening.

Kandi and I have both mentioned my Wine, Wigs, and More event on her blog that took place on March 1st but the real story took place on leap day! I was supposed to go out with a co-worker but she came down with the flu and my wonderful and supportive sister was busy as well so I went solo for the night. I did some window shopping at the mall where I got my makeover the previous week and tried on a few things along the way. I talked to store associates and other patrons in the stores I went to with no issues. I then went to a Dollar Store to buy some hangers so I could eventually hang up my Sherry clothes in our home office closet. I had my clothes in garbage bags shoved in the bottom of my closet which was a pain in the … Before walking into the store I was approached by two people asking if I could sign a petition to get an issue on the ballot but after some discussion I couldn’t because I wasn’t a registered voter in the county I was in. At no time did it appear either person “read” me. I then went to one of my favorite restaurants that Kandi took me to and that’s where the real story begins.

As I entered the restaurant I was immediately welcomed by our favorite bartender Leah. She is one of the most beautiful (internal and external) people I have ever met! When I sat down at the bar she told me I might have to move down eventually to make room for more patrons (a bit of foreshadowing!). We asked each other how things have been since it’s been sometime since my last visit. She told me I looked beautiful and that she loved my hair (I had my blonde wig on), the comment wasn’t superficial but a genuine, heartfelt one meant to make me feel good (it did just that).

I ordered an appetizer and a Lemon Drop Martini and chatted with Leah. The bar started to get busy so I moved down one stool to accommodate a couple waiting for a table. I chatted with the wife a bit until they were seated as well as another couple doing the same. A gentleman came in to pick up a take out order and ordered a glass of wine as he waited for it to be ready. He was a “regular” because he knew Leah and she asked how things were and he told her how his dog was dying of cancer and he was extremely sad about it. You might recall from a previous blog post that someone bought Kandi and I a drink so I paid it forward and bought him his wine.

When he got his bill Leah told him I bought his wine and that started a conversation and my attire was a non issue. After he left another gentleman sat down and this is where it gets interesting! Another group of people came to the bar which necessitated another move in seats next to this guy. The two new couples were wonderful and of course the guys were having a conversation and the ladies sitting next to me were having their own. I interacted with the ladies for a bit until the gentleman on my other side introduced himself. He mentioned that he was supposed to go to the Cavs basketball game but his friend couldn’t go so he went to another restaurant but couldn’t get in and ended up at Taste. I told him a similar tale and we had something in common! Throughout this time I was doing my best to act and sound as feminine as possible and I was succeeding because at first I think he believed I was what I was portraying. He told me I had beautiful eyes and his body language suggested an increased level of arousement towards me. I am good at sounding feminine for short bursts but I am not able to sustain a prolonged discussion with a good female voice. We had some light conversation and I could tell after a while he wanted to ask me a question. He was apprehensive but I told him he could ask me anything. He started by “Are you a…” he hesitated and I said “Yes I am”. His reply was “Really?” I could sense his mind was racing and the level of intrigue rose exponentially. As we continued to talk he twice did the cheesy “stretching the arms” move to reach my shoulders so he could rub them. Now, I have thought about what I would do if I was ever hit on but this was the first time it truly happened. After talking for at least 30 minutes he finally asked “What now?” My reply was “since we’re both married, nothing” When he left he gave me his business card. As we were talking I thought about how women have total control over a situation like this, the guy is basically begging for sex and the woman controls if that happens or not. After he left Leah looked at me and asked if I was okay. I was but I was shaking from the situation and excited at the same time. I asked her what she does in these situations and she said you must be in control and assertive at all times. In the end, I was extremely flattered by how he was attracted to me. My goal has always been to study every part of femininity so I can use that knowledge to portray the best woman I can to pass. Everytime I go out my confidence grows!

The next day was the Wine, Wigs, and More event that Gina and I planned. We wanted this to be a networking/open house event to gather individuals together. We didn’t know what to expect but for our first effort it turned out better than we expected! About 14 people showed up with a few of the ladies bringing a supportive person with them. I arrived early to help Gina set up and we had to go to the nearby grocery store to get a few things. When we arrived the store was crowded and the two of us went about our business to get the needed supplies.

At no time did I feel uncomfortable even though I was over dressed for the grocery store! As people arrived at the salon we greeted them. It was wonderful to see everyone who came, one couple drove over an hour to come! Most ladies were CD’s but one was a transsexual who is having her surgery in a month! We talked for awhile about it and I commented on her beautiful long brown hair. She told me that most family members disowned her when she came out…that’s sad, I told her we were here for her. Everyone mingled with each other and it appeared all enjoyed themselves! We are already planning the next one. Since this was a “trial” run it was more of an open house but the next will have demonstrations with makeup, nails, hair, and voice exercises!

After the event was over my sister and I went to a restaurant for dinner. The entire time I was greeted in a feminine manner and one server even commented that she liked how my eye makeup, glasses, and dress matched! All in all a wonderful weekend! On Monday when I went back to work in male mode I was a little depressed getting dressed putting on my boring male clothes.

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