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.

Crown Girl – Part 2

By “Miss America” Sherry Greer

On January 27th I was finally able to go to my second session at Crown Studio with Heather. We had to reschedule a couple of times so I was SO excited to meet again! I was able to leave the house a little early and went to one of my favorite thrift stores. I casually shopped and made “small talk” with other patrons when appropriate. A teenage girl told me my boots were sooo cute! After spending about an hour in there I walked out with a tan lightweight top for $.75!

When discussing the session beforehand, Heather said she wanted to continue to work on my walking, diction, and go over my makeup routine. As I arrived Heather was just finishing up with another client so I waited patiently in the studio because they were in another area.

After they left I hung my dresses in the changing room and sat down with Heather to catch up on what has happened since my last session. We talked about my past few outings and future plans, how I feel when Sherry, and how my wife has continued to accept my other half more and more. I feel VERY comfortable talking with Heather and feel I can tell her anything. I told her how I feel more and more comfortable and confident being Sherry and when I am her I am mentally 100% woman. I want to totally pass and be viewed as “another woman” in the room. Wow… that was deep.

Before going into the studio I put on the olive dress I bought at Target. We started by reviewing the modeling poses and continued with new ones. She demonstrated them along with how to walk the runway. I walked behind her copying what she was doing. We took a break from that and sat down. She had me read some inspirational passages using my best female voice and making corrections where needed. She also looked at my makeup kit to see if I had everything I should have…I did! Next time she wants to do a full makeup tutorial. She then had me change into my blue dress I bought from We practiced more walking and she sat in a chair with her back to the mirrors and I had to walk towards her multiple times. The dress made me feel SO sexy and I went to a place of femininity I’ve never experienced. Every ounce of manhood was flushed away in a heartbeat. It was like I was having an out of body experience! All of these techniques she’s teaching me are for modeling which definitely interests me!

After the session was over we went to Vaccaro’s which is the restaurant/bar we have been to a couple of times and the reason I found the studio in the first place, Kandi had a Supper Club there. (Thanks, Beautiful). [You are welcome!] We each had a glass of wine and had a wonderful conversation about relationships. Our bartender was very nice and she recognized us from the last time. As we were leaving we both said we had a good time and hugged. Driving home I really reflected on the last few hours… what a day! Upon getting home I went upstairs and “tore down”. First thing I did when seeing my wife was give her a kiss and tell her I love her… I REALLY do!

Stay beautiful-Sherry

From Disappointment to Joy!

By Sherry Greer

As you may remember in my last post I talked about Crown Studio and how I was supposed to see the owner Heather. She was going to teach me about feminine movement and everything that goes along with being girly. Unfortunately, she had to cancel two hours before we were to meet because her father tested positive for COVID and she was around him. So…that was the disappointment.

Fortunately, she tested negative and dad is well on his way to recovery! Heather and I continued to text and came up with the Monday after Thanksgiving that worked for both of us. It was a horrible weather day with rain all day that was going to turn into a snow storm later that night and the following day (Yes, we did get about 13-14″ of snow! That’s Northeast Ohio).

I picked out my outfit accordingly wearing blue jeans with a mustard top and a tan fly away cover. I wore my brown below-the-knee boots and a shawl to keep warm. I actually forgot to take a picture!! Who does that?? As I was getting ready my wife was in our office working! I left the house about 11am and went to a local consignment store to browse. This store is in my hometown and I’ve always wanted to go in there. That is the first time I went to a store in my hometown. I almost bought a cardigan sweater but decided against it because I knew I would get a better deal at the thrift store I was going to next.

I then went to that thrift store and shopped for at least 90 minutes! This place has so much that you need that time. I found the leopard print dress, black jeans, and two sweaters for $5.60! Fortunately everything fit. When I got home I told my wife what I bought and of course she said jokingly that I didn’t need any more clothes! Upon leaving the thrift store I realized I still had some extra time so I traveled to a nearby mall close to the studio. Nothing really happened at the mall. I was just another woman shopping. I went to a few stores and in most the SA approached me talking about the sales and I chatted briefly with each, no funny looks from them, just natural conversation!

Now for the Joy!

I made my way to the studio and arrived about 10 minutes early (Yes Kandi, I was actually early!). I checked my makeup because I wanted to look my best. I brought two dresses and two pairs of shoes so Heather could pick. I also grabbed the items I just bought to get her opinion. Heather and I walked in together and immediately the connection that we started via texting continued! Walking into her studio I immediately felt a welcoming/inspirational feeling. As you will see from my pictures there are inspirational sayings stenciled on the walls. The girly girl feel was evident with pink in many places and chairs looked like high heel shoes. What a wonderful person. Heather showed me where to put my things and we sat down to get to know each other better. She asked me questions about where I want to go with Sherry. I really answered all her questions very honestly and accurately. After about 30 minutes of talking it was time to get dressed and to start the class. She loved the two dresses I brought but at the last minute I showed her the leopard print dress and she said wear that.

The lesson started with posing. She showed me how to properly hold my head, hands, shoulders and feet. We then progressed to walking. She made sure I placed my feet in front of each other in a straight line as I walked and had my elbows close to my body with my arms slightly bent with hands open. We moved on to properly sitting and facial movements such as smiling in various ways.

Throughout our time in the studio Heather took videos of me and I of her demonstrating the proper techniques so I could practice at home. The session lasted almost two hours but felt like 10 minutes! There is SO much to learn. She said I’m a natural and am better than many of the women who come in. She says I have the “look” and could model! I have never thought of that as a possibility but it is an intriguing proposition nonetheless. At least, I want to help her when she puts on shows. I also want her to come to Gina’s Salon when we restart our group that we started just before the shutdown in March. Heather is a model, pageant contestant, and actress. She is actually filming a Hallmark type movie with Dean Cain (Superman) as I write this!

After the session we went over to Vaccaro’s restaurant for a glass of wine. I needed to ask the waitress from Supper Club a question and she was meeting her boyfriend. We walked in with our outfits on that you see in the picture of us together. The bartender, Rosie, was wonderful and I felt amazing, natural, and fabulous sitting there as a beautiful woman! After my wine we hugged and said our goodbyes! What an amazing day, I can’t wait to continue my lesson!

Ladies, if you live near the Cleveland/Akron area and this is something you want to do I highly suggest you contact her. She is a beautiful person who wants to see happiness in people. Heather is on most social media, look up Heather Habura. Now onto Supper Club!

Stay beautiful-Sherry

Giving Back

By Sherry Greer

A fundamental need of all of us is to be supported in what we desire to do. When I first came out and searched for support I found it in a trans woman named Natalie as well as with Kandi. These two ladies showed me guidance and support (still do) that I am truly grateful for and has helped shape who Sherry is today.

A couple of weeks ago Natalie texted me saying she has been working with a trans woman who is just coming to terms with who she is and that she is very much in need of support and guidance. Thinking back to the help that I received I quickly asked if I could help with her. My wife was going out of town for a couple of days and I took the opportunity to meet her. After a few emails back and forth I decided to meet her for breakfast at a very LGBT friendly restaurant in the Tremont neighborhood in Cleveland. This was the first time that she was out with any type of female clothing on. She dressed in a t-shirt, black tights, and black mules with no make-up or anything else remotely feminine.

We had a wonderful conversation, I did a lot of the talking because she is reserved. We talked about her story, my story, deportment, make-up, what her end goal is, and more but I think the biggest one… Confidence. That takes a long time to get but makes all the difference. Regardless of where you’re at on the gender spectrum you need to be happy and confident with the reflection in the mirror (remember my past post about the (Wo)Man in the Mirror).

As we were talking I felt myself become more confident because I wanted her to see that! I really enjoyed our conversation and want to help her blossom to be the woman she wants to be.

I scheduled a hair appointment for that day as well and asked her if she wanted to come with me. We got to Gina’s Salon and Wigs a little early, you might recall that Gina and I had an open house at the salon just before the COVID shutdown. We looked at the wigs and talked about styles, length, and colors. After Gina was done with her appointment I introduced my friend to her and she gave some pointers and told her to come in to try some wigs on, hopefully that will happen! As I sat in the chair getting my haircut the three of us chatted like women would at a salon. I know I gave my friend a lot to think about and hopefully I can help her more in the future. Later in the day she texted me to thank me for a wonderful time and even suggested about coming to the Supper Club.

Since my wife was out of town overnight I went out with Betty and Daphne from Supper Club the night before. I made reservations for the three of us at a restaurant none of us has ever been at. We got seated right away and ordered a drink but the place was so busy that food would have taken at least an hour to get. We decided to go to the same area where my friend Lori lives since it was close to where we were. This restaurant was not as crowded and there was live music playing. We decided to eat outside since the weather was so nice. There were multiple tables set up by the sidewalk and we could easily see people as they passed by. At no time were there any strange looks as we ate and enjoyed ourselves. We had a great conversation about many things female and made arrangements to go out again. I feel totally comfortable being Sherry and look forward to the next time I can get out!

Hope you like the pictures, the purple top was dinner and orange was breakfast and my wife bought me everything but the purple top!

Stay beautiful-Sherry

Kindness, pass it on! Pay it forward!

I’m Not Alone!

By Stephanie Julianna

I have loved girls’ clothes, then women’s, from my earliest memories, around 3-4 years old.  Yes, some people can remember that far back.  I am the youngest, a surprise baby, of a family of three older sisters and a brother.  I was born in early 1949 and spent my younger days admiring my sisters, mother, girl classmates, and the girls in my neighborhood on Long Island, NY with their amazing full dresses and skirts.  I attended a Catholic Grade School that did not require uniforms.  Boys had to wear dress slacks, white shirts and either a long tie or bow tie.  Oxford shoes only, no sneakers.  The girls had to wear dresses or skirts and blouses.  There was no rule about skirts being too short because they were all knee length or longer anyway.  Mini skirts had not become the fashion yet. 

In 1956 my family moved from a cramped 1 and 1/2 bedroom apartment (remember there were seven in the family) to a three bedroom Cape Cod style house with a full basement.  I was seven and that was when I was left alone without a babysitter for the first time and immediately took advantage of my sisters’ and even my Mom’s closet and dresser drawers.  My life started on the path of a crossdresser that, after 64 years, I am still happily traveling.  But I was alone, as a boy, and I knew it.  Society frowned on any male, young or old who would want to dress feminine unless it was a parody of one, like what Milton Berle or other comics of the 50’s did.

Fast forward to the fall of 1962.  I am now in another Catholic school, but now it is a boys High School.  It was a college Prep School in Brooklyn, N.Y.  We were required, from freshman year on, to use the famed 5th Avenue New York City Public Library to do research for any papers we were assigned to do.  I was now thirteen and still feeling like I was the only boy in the world who wanted to dress like a girl.  The weight of carrying this secret was truly heavy on my soul.  Things were very different back then compared to now.  Imagine letting a thirteen year old commute 2 hours each way to school and back home, via bus and subway today?  Then add to that, commuting into Manhattan to that phenomenal World Class NYC Library on the corner of 5th Avenue and 42nd Street on Saturdays to do more studies.  No parental monitoring.  At thirteen a boy was on the threshold of being a man in those days.  Amazing times to grow up in.

It was on one of those Saturdays that I finally found out that I was not alone.  You could leave your books and papers where you were sitting in the amazing Reading Room at the Library and return an hour later without a page being disturbed.  I would eat my brown bagged lunch in Bryant Park behind the library.  But one day, I wandered down 42nd Street toward Broadway and Times Square.  Everything seemed new and amazing to me.  But when I got to Broadway and looked down the street toward the Hudson River, it was like I was looking into the gates of Hell.  After all, I was a thirteen year old Catholic boy.  I could see movie marques hanging over the sidewalk for what seemed like forever.  And they all had XXX next to the titles of the movies.  Coupled with the signs that announced ADULT BOOKS all over the place, I thought I had just committed enough sins, just looking down the street, to go straight to hell. 

It took a few more Saturdays before my curiosity took over and I ventured past Broadway.  I remember it as clearly as if it was yesterday.  As I passed the Times Building and stepped onto the curb on the “sin” side it was only a few store fronts before I looked into a window and saw the Premier Issue of Female Mimics on display.  I was riveted to the spot.  On the cover was a guy on the left and a girl on the right.  In seconds I realized that they were one and the same person.  I was not alone.

I went in and grabbed a copy.  My face was burning red but I was not leaving without that magazine.  “How old are you, Kid?”, the clerk asked.  “Eighteen, Sir.”  No ID was asked for.  He slid it in a brown paper bag and I rummaged my pocket for the money to pay him.  I did not take it out of the bag until I got home hours later and in the privacy of my room I entered a whole new world where there were people just like me.  Well, I was not in their league yet but little did I know that I would be a part of that world years later, rubbing shoulders with some of the Royalty of the NYC Drag Scene. 

I am presenting pictures of the first issues of that awesome publication.  It was one of the first magazines devoted to professional female impersonators. I am also presenting an early picture a few years after I became very active in the Drag scene from the early’80’s and one a few years ago.  The last 20+ years I have simply moved my dressing into the public domain mixing comfortably with the general public.   It has been a wonderful journey with many adventures in female mode that I hope to share with Kandi’s readers in the future.  I am so thrilled that Kandi has invited me to share my stories here and would also love your thoughts and comments.  


Stephanie Julianna

I love and miss you, Steph!

My Weekend

By Sherry Greer, our Miss America!

(And I add parenthetically, a few weeks back.)

My wife loves to gamble and goes out of town periodically with her two friends to do so. A few weeks prior I was looking on the internet to find something to do and noticed a local artist, Michael Sherry, was having an art show at a restaurant/hotel in downtown Cleveland. When I saw his last name I just had to go! The place is called The 9 and I have been there before (in both modes) so I knew it was good. Kandi also had the very first Supper Club there. I asked Kandi and Annie if they wanted to go.

I made reservations for 6:15 for dinner and we would meet a little earlier to view the artwork. Kandi said she would meet us there. A few weeks earlier I told Annie I wanted to do her makeup so today was the day! I mostly got ready but still had my eyes to do when she arrived. Annie came to my house about 2:00. We first had a drink and then we went to the bathroom and got started. I sent Annie a few still pictures from a few videos I watched and she picked her favorite. I tried my best to duplicate the look. It’s really hard to do someone else’s makeup and it’s only the second time I’ve done it, I actually did my wife’s before! It was wonderful to be surrounded by femininity.

The two of us talked about what I was doing and how excited we were to go out. Annie brought a couple outfits and we picked out the best one. I like matching eye makeup to my outfit so I tried to use the same or similar colors for her eyeshadow. She said she learned a few tricks watching me so overall it was a success and she liked the look I created! I finished my eyes quickly as she did her hair. I asked her to pull my hair back into a loose ponytail and it looked beautiful. I couldn’t wait to wear my dress because I’ve been waiting for just the right occasion.

We drove together and it was wonderful talking about female issues with her. She’s definitely one I feel comfortable talking to and like my friend Heather I feel I can tell her anything. The temperature in Cleveland that night was in the high 20’s and felt quite cold on my bare legs. We valeted my car and it was a wonderful sound as I heard my 4″ stiletto heels click on the pavement. They really are very comfortable despite being that high! We arrived before Kandi and were viewing the artwork and having a complimentary glass of wine when we met up with her.

The event coordinator was nice enough to give us a tour of the artwork on another floor. After 30 minutes or so we went down for dinner. The food and company were tremendous and our waiter was extremely knowledgeable and nice and made our experience memorable. After dinner we went to the Vault which is downstairs and actually inside an old bank vault. There’s multiple private rooms plus the bar area. The entire area has a Speakeasy vibe. After one drink we called it a night. The entire night was amazing and the feminine feeling and spirit running through my body and the experiences that I am having as Sherry is something that continues to build into something I’ve never imagined. As I was driving home Annie and I reflected on the evening.

The next day my weekend continued! At the last Supper Club I told my friend Jessi that I would take her makeup shopping. Annie decided to join us after she got off of work. I left my house early and went shopping to a few stores around the Ulta we were going to. I bought a top at Rue 21 from the clearance rack for $3! I arrived at Ulta early and I of course was approached by a sales associate. I explained to her about Jessi that she is a mtf who is just starting to transition.

Jessi arrived and then Annie a few minutes after that. The SA was doing color matches for foundation and concealer and kept on asking me to get my opinion. I truly felt like the SA thought I was a woman. I know Jessi needs help and I am happy to help her and want her to build confidence in who she wants to be. After buying a few things in Ulta we went to Target to buy a few more products. It’s amazing that the more I help Jessi build confidence the more I build confidence! What an amazing two days! The picture with the purple top is from Sunday.

Stay beautiful-Sherry

I go back and look at pictures from our early outings and Sherry has blown past me in terms of her presentation and overall view of things. And that makes me happy!

November Supper Club, Sherry Style

On November 11th I met Kandi and Annie for the Supper Club. It was supposed to be five of us but two people couldn’t come. As I pulled into the restaurant parking lot I parked in a spot right in front of Crown Studio (in Fairlawn, OH). On the storefront it said that the studio specialized in movement, etiquette and image consulting among other things. As I was reading this I couldn’t believe it, this is exactly the kind of place I’ve been looking for! As you may remember, I’m a very detailed oriented person who wants to pass as much as possible and I couldn’t wait to call to book an appointment. I was so excited as I walked into the restaurant! Annie and I walked in at the same time and found Kandi waiting for us and talking to a wonderful bartender.

We made our way to the table and ordered a drink from our equally wonderful server. We had an amazing time eating, drinking, and having a great conversation talking about a number of topics. The three hours seemed like 30 minutes! Time flies when women start talking! I asked if anyone was available on the following Friday and luckily both ladies were. We agreed to meet at a favorite restaurant of Annie’s.

So… the next day I made an appointment with the studio for the Friday before meeting for dinner. The owner Heather and I exchanged multiple texts and she asked me probing questions about what I want to accomplish, I sent her a few pictures and she said I was gorgeous with nice hair and beautiful coloring! I sent her my blog post titled The (Wo)Man in the Glass [which we will be rerunning soon, which Sherry doesn’t know until right now!]. I asked if she knew I was male before reading that and she said she didn’t! I also made a manicure appointment at a close by beauty school.

Friday came quickly and I arrived for my nail appointment at 11am and was taken right away. I could tell that my nail tech Michelle was nervous as she started trimming my cuticles, I told her to relax and it would be just fine! I mentioned my favorite poem to her and told her to be confident and she thanked me for that and said she would look up the poem. We talked about our Thanksgiving plans and I told her my son, his wife, and my parents were coming over. We talked about that she used to be a bartender but needed a change so that’s why she’s in beauty school. We talked about relationships and that she has an 11 year old daughter. She mentioned a friend that is rather promiscuous and isn’t a good role model for their daughter and I agreed. She said, “you’re a mom, you know how it is!” when being a good role model for your child.

She also mentioned that I have beautiful hands and I should have been on a Dawn dish soap commercial [I was thinking Palmolive, but I am aged]! I must say that I’ve had better manicures but the conversation was the most real one I’ve had. It was definitely two women talking about issues that are important to women. I can say with 100% certainty that she thought I was a cisgendered female! I left the salon about noon feeling amazing and SO looking forward to my appointment with Heather. I went to a nearby mall and did some window shopping until my appointment with Heather.

Now comes the disappointment… Heather texts me about two hours before we’re supposed to meet. The text starts out “So…I have a change of plans…” Noooo…turns out her dad just tested positive for COVID and she was around him so she needs to quarantine and get tested. Talk about disappointment! Obviously I texted back understanding and wishing everyone well. She said she was equally disappointed and that we would definitely reschedule. I did more shopping and went to a couple thrift stores until I met Kandi and Annie. In the one store I commented to a woman that I liked her boots and she replied “Thanks, I actually bought them here”. I spent $3 on a cream colored shawl to throw over my shoulders when chilled!

I walked in the restaurant to find my two BFF’s sitting at the bar waiting for their drink [Yeah, that Kandi is a lush!]. All of the workers knew Annie and our bartender, Kat, was a doll! She took great care of us and another worker was wonderful and took our food orders. At no time the entire day was my attire an issue.

The three of us sat there for 2 ½ hours talking and having a great time until Kandi had to leave. After [we got rid of Kandi] Annie and I continued talking for almost two more hours! It really felt natural and I really enjoyed my entire night. Annie asked me questions about my dressing and I was really honest with her. I have (Kandi has also) developed a great relationship with Annie and feel like I am a girlfriend to her! We left just before 10pm because that’s when our governor who issued a curfew says we lose our glass slipper and turn into a pumpkin. I look forward to the next time out and definitely look forward to meeting Heather. Hope everyone is well and Happy Thanksgiving [a few days ago, but the Thanksgiving week posts were already written]!

Stay beautiful-Sherry

[Editorial comments by yours truly….]

Sherry’s September Supper Club

By our Girl About Town, Sherry Greer

September 14th marked another supper club dinner. Since I had to work all day I rushed home to get ready for the night. I made sure I picked out my outfit and did any prep work I could on Sunday. The blouse I picked out my sister purchased for me on and the skirt I bought at one of Kandi’s favorite consignment stores. My wife was home as I was getting ready just like she has been the last three times. It’s been amazing how supportive she has become. I know it’s very hard for her but her effort has not gone unnoticed. My friend Lori was going to come but had car trouble the day before. Since my top had silver and black in it I did my eye makeup to match, I really like to match my makeup to my outfit! I wanted to wear my natural hair so I pulled it back into a ponytail, used a matching hairpiece for more volume, and put a matching flower in it to add that girly touch.

Since my wife’s birthday was on Tuesday I needed to get her a card so I stopped at a Rite-Aid store before dinner. As I walked around the store I loved hearing the clicking of my heels upon the floor and the feeling of calm and comfort. I picked out the card and perused the isles a bit before paying. I was excited that my sister would be joining us for dinner. We went out together for dinner in January and she came to the open house that I helped organize at a local salon in March. She has been wonderful and is glad to have a big sister!

We both got to the restaurant at the same time so we walked in together. I almost fell flat on my face because I didn’t see the step I had to go up because my mask impaired my peripheral vision, now that would have been embarrassing! When we walked in Kandi and Susanne were already there. My sister sat next to Kandi and they immediately started talking and catching up from the day of the open house. It really made me feel good that my sister is so comfortable with our community. They talked like they were BFF’s!

Susanne and I talked until everyone else arrived. At last months’ dinner I met Betty and Daphne, they make a wonderful couple. Betty sat next to me and we immediately started talking. She is the founder of a local county LGBT group. We talked about educating people about the Trans community and also about me and how I got to where I’m at today. I opened up to her like we’ve been girlfriends for a long time, what a wonderful conversation. A new couple was there, it is nice to see how the supper club is evolving into an open and welcoming environment. Thank you Kandi! [You are VERY welcome!] The food and the rest of the night was wonderful, it just flew and seemed to end too quickly. I look forward to the next dinner, can’t wait! Hope you like the pictures.

Stay beautiful-Sherry


By Sherry Greer

In past posts I have talked about the relationship that my wife and I have had when dealing with me being Sherry. It obviously hasn’t been easy with us going to counseling, the arguments, the not trusting, etc. As time has gone on and being quarantined situations have come up where I (we) have had the opportunity to discuss Sherry. Through those talks I have regained her trust and she has realized that I am still the same person (her loving husband).

Recently we were talking about me going out and at the end of the discussion she said that she wanted to take me shopping, my jaw dropped!! I was amazed on how she could go from just about hating to look at me in the beginning to saying that, WOW. I truly don’t know if I could do that.

So…my wife received a 30% off coupon from Kohl’s and the weekend of August 7-9 there was a no sales tax in Ohio. I figured this was a great opportunity to remind her of what she said! On that Friday we went to Kohl’s. We first went to a jewelry store where I bought her some jewelry for our 30th wedding anniversary. She wanted to exchange what I bought her for an addition to her wedding ring.

After leaving it was my turn! We walked into the local Kohl’s and went to the clearance section. We took about an hour looking through the racks picking out multiple tops, cropped pants and even a cute romper. As we were pulling things to potentially buy she would make comments like “this would look cute on you” or “this is beautiful”! She also said that when she’s shopping for herself in the future she’s going to want to get something for Sherry. After picking out the clothes we moved over to the jewelry section to look for a wedding ring that I could wear when out but couldn’t find one in my size.

We also looked in the “Intimates” section for a waist cincher but couldn’t find one that I wanted. Upon getting home my wife asked me if I was going to try my new purchases on! She was genuinely excited to see the clothes on me. As I tried each article on my wife made positive comments about each and everything fit except one black top. We decided to take that back on Sunday.

After breakfast we went to another Kohl’s to exchange the top. We couldn’t find one but she picked out the rust colored top and beautiful LBD! We had to do some grocery shopping so we went to the nearby Walmart to do that and we found a ring there as well. Obviously the ring is fake and was only $10 but in reality it’s priceless because she not only picked it out but it’s a symbol of our love and her willingness to be open to Sherry.

After getting home I again tried on the new purchases and when modeling the LBD she asked me to turn around and jokingly said “you bia…” because it looked really good on me! When we were walking out of Kohl’s on Sunday she asked me if I was happy and my response was “no, I’m astonished”. My outing with my friend Lori and dinner with Kandi to follow soon.

Stay beautiful-Sherry