How I came to Cross Dressing

[Leslie Mary S]

I have read many stories about how many of you came to be here. I have thought hard about it and myself.
So here is the first part of my story.

I have reviewed my past.

I can recall no incidences where I dressed until I was 21 years old. Now you must understand that I have trouble recalling many things before I was 13. Thirteen was my age when my parents broke up. I had learned to square dance at the age of nine. Square dancing was a fun thing for me so I remember it.
I have just started, at the age of 65, to fill in some of that gaps in my life with some of the non-happy thoughts like spankings etc.

Anyway, I went into the USAF when I was 19. I met my wife when she and her folks came out to learn to square dance. I was one of the helpers to the caller. I married my wife in my 21st year (Dec 26th 1964).
It was during the square dancing that they had gimmicks, and gags, where they dressed up men in the female attire. I found that I always was trying to get the position of the one dressing as a woman. I liked the feel of the clothes. I also learned how to dance the female parts. Knowing how to dance the female parts was a good thing because when we did not have enough females to make a square (normally 4 men and 4 woman) I could fill in as a woman. I also liked to be twirled and swung.
For 36 years this is what we did for entertainment. I went on to become a Square Dance Caller for 15 of those latter years. Even called at several National Square Dance Conventions. Frequently the dancers liked to dress the caller as a female or wrap them in tissue paper mummy style while he was calling to see if they would hinder his calling, I never was hindered. As part of the training to become a caller, you were required to be able to envision the dancers dancing in your mind. At any time you had to know where each dancer was on in the square.

When my wife passed away 23 June 2000, I had to give away all her clothes, many of which I had sewn. I could not wear them even if I wanted to. I was 6’ tall and 200 pounds. She was 5’ tall and 95 pounds. I tried going to “singles square dance” clubs, but it was not the same. I did remarry but that fell through, I was still in love with my first wife.

I, through divorce court action, ended up giving my Alabama home to the second ex-wife. I moved to my TN home in 2005. I set up a photo studio in the garage. I adopted one of my models, model name of NormaGee, as a daughter. It was she and another model, Kimberly Diamond, who, to show the photographer what it felt like to get all dressed up, dressed me up. I found out that I liked it. The real seed was planted to start me into Cross Dressing.
Eventually in 2006, NormaGee set up an appointment for a makeover with Mrs. Cross in GA. Then we went to my first meeting in Atlanta of the Tri Ess chapter, Sigma Epsilon. It is there that I adopted the name Leslie Mary Shy. NormaGee adopted the name DarkAnGGel. She had replaced the single lower-case “g” with the upper-case “GG” to show she is truly a Girly Girl.

I will stop here. Maybe I will tell you chapters two and three.

[Beverley Sims]

Leslie a very interesting first chapter, I agree square dancing was fun for me too.

I had some lovely skirts and petticoats that I sold due to lack of space.

[Robbiegirl]

Love the Story, Can't wait to hear more. Have always wanted to try on a square dance out fit !

It was during the square dancing that they had gimmicks, and gags, where they dressed up men in the female attire. I found that I always was trying to get the position of the one dressing as a woman. PLEASE TELL ME MORE ABOUT THIS ??? Sounds so fun ! Are you saying that if i guy lost or won he ended up in an actual frilly square dance dress and even a petticoat ??

Where did the dress come from ? Who dressed him and How did the women react especially the ladies date ?

[Leslie Mary S]

some of the GGs were on the heavy side and provided the clothing which was normally worn over the guy clothes. is where the clothes came from. I could wear my size 2 wife's petticoats (I made them) because I put extra elastic in them.
In some of the gags the women dressed the guy on the spot. In skits the guy's wife normally helped him get ready in a bathroom or at home. Oddly enough I NEVER dressed as a female square dancer for Halloween.
Yes guys did end up fully attired. Sometimes it started with a side sports team bet, other times it might have been their birthday. Square dancers like to have fun even when not dancing. The one time they caught me truly off guard was at a square dancers camp-out. We were having a pajama party when they 'forced me' to put on a teddy with frilly undies over my PJs.

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Chapter 2

The first time we went to Atlanta we went in my F-150 Super Crewcab truck. DarkAnGGel’s boyfriend at the time was Mike, he was driving. We had left 2 hours early just in case we got lost or wanted to do some shopping.
We were southbound just south of Rome, GA, but north of the I-285 loop, when we had a tire blow out. We had a spare and a jack. The ‘L’ shaped tire iron that came with the truck could not loosen the tire nuts. They had been put on with an air powered wrench at the tire shop when we had the tires rotated and properly inflated for the trip.
There we sat on the left side of the road, we had been traveling in the left lane getting ready to veer off to the left when the tire blow, with no cell phones. Finally, a truck stopped who had a cross-bar type tire iron. We got the tire off, and changed it to the properly inflated spare. We offered the man $20 for having stopped and he declined it and he said. “Pass it Forward”.
We got to Mrs. Cross’ just 15 minutes late. DarkAnGGel went to the door and handed her
They sat in the truck while Mrs. Cross took me into her Studio and did her magic. She sat me down and did her make-up magic. When she was done a check straight off.my face and put a blonde wig on me, I looked like a movie star. She then had me put on a full corset, forms (DD), hose, and black Dress, and black heels. Then she used my camera and her camera to take some photos. Costume change time. Then came a red corset and a red boa. More photos on the bed for some sexy photos. She said I was the first that didn’t really want sexy bed photos. We shot them anyway.
It was getting close to going time so she dug around in the wardrobe I brought and came out with my brown wig and a black and red top and black skirt and matching heels. Then we went down stairs (oh the fun going down stairs in heels) to her other photo op area for more photos.
Then I went outside to her porch and had more photos taken. We got directions to the meeting hotel.
We went into the hotel at the registers desk, got our room and took our luggage to our room. DarkAnGGel (a model) redid my makeup to something more normal. I went down to the meeting room and met Phoebe, Sandy, and many of the other members for the first time. Interestingly enough, at the meeting, I was not nervous.
That night we went to a guy club that was having a Drag Queen show. I got to meet the Drag Queen host and talk to her for about 5 min. I later learned that the host was none other than RuPaul.

The next morning, I took the truck to a Goodyear store and got a new pair of tires for the front. We returned and I and DarkAnGGel went shopping with a group of girls. I wore a pair of 4” blue heels to match the blue outfit I was wearing. I got my second makeover for the week-end and my first blister on one heel. Those heels were not the shoe to wear to go shopping. DarkAnGGel also got a makeover.

That evening they had a 50s party. I had come prepared. I had a set of black and white saddle oxfords, white poodle socks, pink petticoats under a black felt poodle embossed skirt, White blouse emblazoned with a black poodle, a pink neck scarf, Pink framed American Leading lady cat eye shaped glasses, and a pink head band. I also had a 45 RPM record case with records and pink lipstick. A pink beaded tennis bracelet. Around my neck was a 21” chain with my Drab 1962 class ring. I know it was a 50s party but it was the best I could do for class rings. Sandy came as Sandy from Grease. She was a Sandy look alike. (She eventually transitioned). We had a lot of fun that night. We got Mike to act as the Prom King to Sandy’s Prom Queen.
Sunday morning was breakfast. Those in drab were not allowed to mix with those dressed. I looked over to the drab members and could not identify any of them from the night before.
When we started out for home, we stopped at a fuel station to fuel up the truck and for me to do a bladder call. The attendant behind the counter refused me the key to the only restroom and told me “We don’t allow your type in there.” I came out still needing to go. Mike went in got the key. I went around the building and met Mike at the door. Mike let me in and stood outside the door until I came out.
The rest of the trip was uneventful. Mike pulled the truck into the garage and Leslie Mary went into the house.

Still more to come.

[missjoann49]

Quite an interesting story Leslie. Mine started a little different when I was quite young maybe around 3yrs of age. I was an only child and my mother had always wanted a girl. My dad worked a lot of nights so whenever he wasn't home she would dress me as a little girl. This continued right through my junior high school years. Everyday when I would come home from school and my dad wasn't home she would have my clothes all laid out for me and I would have to change and become her daughter. As I entered high school things slowed down a little, but when nobody was around she would have me fully dress for her. Without going into a lot more detail it is who I am today and enjoy it very much now, I can say I am happy with myself

[Robbiegirl]

Thanks so much Leslie Marie. Who knew Square Dancers could be so much fun !

My last question is do you recall if the ladies got a kick out of seeing guys in their dresses and petticoats ? Women can be so much fun and in my experience get alot more of a hoot seeeing guys experience wearing women's clothing than men do ? Oh and I assume they didn't have to wear the ruffle butt panties ?

[Leslie Mary S]

Yes the GG really enjoyed it. And on occasion the victims DID have to wear the "Ruffle Butt Panties". It was a very strong requirement when doing a Can-Can type skit.

The third chapter is a very "dark" Chapter. It is why I went back into the closet and changed locations. I will have to be very careful wording it. It is an area that I am very quite about unless I am talking to you face to face.
Maybe I'll just skip over to Chapter 4.
That is where "Hippo is out and about" belongs.

[Jolene Robertson]

Thanks for sharing your story. Love reading it.

[Stephanie47]

A very interesting story. I extend my sympathies on the loss of your first wife.

[phili]

I'm sure I am not the only one saying 'Keep the story flowing, Leslie Marie Shy! ' Keep adding detail. It's good for all of us. I feel like a kid saying 'Tell it again, Auntie Leslie!"

[Robbiegirl]

So I am still a little confused on where you stood with your wife ?

Did she have any thoughts on you wearing ladies square dance attire and did she know how much you enjoyed it ?

Loving your story, hoping their were a few Southern Belle Dresses in your experiences

[Leslie Mary S]

My wife understood what the community wanted and How I felt doing it. She never realized, to my knowledge, I had the compulsion to dress. So I guess I was still in the closet.

[Leslie Mary S]

Chapter 3
(This is the dark part)

A few weeks later Mike, who was now living at my house, asked DarkAnGGel to marry him.
DarkAnGGel reminded him that the only reason he was living in my house was because it was winter-time and his little one room 8’ by 10’ place, which he built by hand, out in his woods, only had a wooden stove, no running water, electricity, or even a bath room.
About 3 months later he moved out and back into his place.
For about 3 months, I provided a place for Kimberly Diamond with a place to live when she and her husband broke up. We had a good time. Then Kimberly got a boyfriend. They got married
and moved into his home in GA. Come to find out, her new man was a drug dealer and a pimp. He started having Kimberly turning tricks to cover the cost of her addition. They tried to get DarkAnGGel to move in with them.
Mike’s cousin, David, started to calling on DarkAnGGel. Mike started providing yard services and assorted maintenance services for the house. He considered DarkAnGGel his girlfriend. One day I went into town. When I got home, David was not around. DarkAnGGel was in her room crying. I learned that David tried to force himself on DarkAnGGel. When she resisted, he beat her up. Unknown to me David had a history of battering his girlfriends. I also learned that that wasn’t the first time had battered up DarkAnGGel. She had claimed to me that she had fallen down the basement stairs twice before while going down to do the laundry. I had believed her.
Come to find out, David had started advertising that he was a model photographer and had a studio. He had my address as his business address. He was using my studio and equipment when I was in town.

This time when she had a black eye and a badly bruised arm, she told me what had happened, I evicted David and got a court order that David was not to come within 1,000 feet of us nor was he allowed on my property. It was then that I learned from the police that he had a history of battering girlfriends, one of whom was still missing.
About three weeks later I had gone into town and DarkAnGGel stayed at home fixing dinner.
I got a call from her that he was trying to get into the house. He did because when He was living there, he had had a key made to the garage side door without my knowledge. I was on the road home when she called me. I called 911 and told the police what was going on.
In the resulting conflict David fought with the officer in my basement and tried to get the officer’s gun. The officer was trying not to get his head bashed in the head with a frying pan by David. DarkAnGGel was trying to stop David and was inches from the officer’s gun when the officer shot David dead. Shortly, there were over 14 vehicles in my yard. The officers mike had been turned on during. I was almost home when all the police showed up.
After the shooting, David’s kinfolk started threating DarkAnGGel and I, saying that we had set up David.
It got so bad that we had to move away. I moved DarkAnGGel twice. I lost the house to Foreclosure. I moved to AL. David had told his Kinfolks that I was a crossdresser. It also came out that DarkAnGGel and I got David to stat crossdressing. He actually did that on his own, He was Danial.
I have to stay away from that part to TN. I, or any of my family, can’t even visit my wife’s grave.
Since I then had AL auto tags his kinfolks knew I was living in AL. On several occasions they came looking for me. They asked around and my friends alerted me. They just didn’t know where in Huntsville AL I was living then. They even went to the house were I and my second wife used to live.

[BLUE ORCHID]

Hi Leslie Mary , So far this has been a very interesting read, Standing by for future chapters.

>>>>>>>>>>>>>>>>>>Orchid ..OO..

[Leslie Mary S]

Just one more to go. Then I will be into this year's posts.

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Your Private Message area is full.

Hi Leslie Mary , So far this has been a very interesting read, Standing by for future chapters.

>>>>>>>>>>>>>>>>>>Orchid ..OO..

[phili]

Wow,Leslie Marie Shy- that is one scary tale- You are pretty cool, calm, and collected, so I'd vote for you for sheriff.

And you and DarkAnGGel can start pitching your story for movie rights !

[Bellatrix]

I'm so glad I joined this forum. I get to hear such awesome stories from people like you. Thanks Leslie Mary for sharing you story. You should write a book!

[Leslie Mary S]

I am, but it is a romance novel and has nothing to do with my life except it starts out with an event from my life. Right now I am at a writer's block as to which path to take the book. The working title of my RN is "The Vault". My writing name is "Feather With Spots".
I have already written over 65% of my autobiography. I realize that I can not finish the autobiography and have told my son, also a writer, he will have too finish it because I will be dead then,

[BrendaPDX]

Thank you! You are a brave sole.

[Leslie Mary S]

I am still working on Chapter 4.
Some one wondered about my having had a woman's cloths. Here are two photos taken in Okinawa at a teens Square Dance. This time I got away lightly.
500 PICT0279.JPG Attachment 301641
Back then I was more of a stick instead of the Hippo I am now. My white long sleeved shirt is on the ground to my right. I didn't get any photos after this with bra and pettie-pants. All worn outside of what you see me wearing.

[Robbiegirl]

Thanks for the pic

[Leslie Mary S]

Chapter 4

After staying tightly in my closet until 2015 I started dressing again. My Closet is my 4-bedroom mobile home. One room is the craft/sewing room. I sleep in the smallest bedroom. A mere nine feet by eleven-foot room. My bed is 4 feet up 7 feet long and only 30 inches wide. Built it myself. I keep 10 totes under the bed with my drab clothing and assorted items in them. I have never rolled out of bed. I do not toss or turn in my bed. Also, in the room is a table 72” x 30” where I keep my computer and assorted shelves.

I have sublet the master bedroom room out to a personal friend of my #1 daughter. That friend, Debra, was having a hard time of it. She is a divorcee who is has filed a bankrupt case. Debra knows about my cross dressing and is supportive.

Her #1 daughter borrowed her car, it broke down. The #1 daughter had it towed to her apartment not here. Since Debra’s daughter could not afford to fix the car, and Debra could not afford to have it hauled here (broken right front axle), it sat where the tow truck left it, taking up two parking slots for two weeks. I could have fixed it but the apartments where the car was at has a strict policy of “No car repairs are to be done in the parking lot”, I could not fix it there. The landlord then had it towed to an impound lot. Debra lost the car because of the spiraling impound lot fees.


Since Debra had no transportation, I was taking her to work at 1 pm. She worked at a fueling station with 18 pumps for one of the big food stores. I would come home and dress. Then I would drive dressed to pick her up a midnight.
At first, I didn’t get out of the car. Eventually I was getting there about 15 minutes early and if there were no customers, a frequent occurrence, I would get out and take a few photos and then quickly get back into the car.
Debra was paying me rent, but with the loss of her car she was spending her money on paying off her bankruptcy, she can not pay her rent to me, which makes it a bit rougher for me.

She had to buy another car and the insurance. There went my rent money.

Debra’s #2 daughter had a baby. Debra now spends most of her “free time’ looking after the baby while her daughter is at work and seems to live with that daughter about 6 days a week. She comes back here to get some rest and away from her grandson.

So, I have my house to myself most of the time. I tried on all of the Leslie outfits and took photos of them in my living room where I have a set of backdrops hung.
I started visiting a local gay bar while dressed. At 11PM they had Drag Queen shows. I got permission to take photos. I started taking photos of the Drag Queens on a regular basis. I would then print out a few head shots and give them to the DQs for promotional use. Soon I was invited back into the dressing rooms. They talked me into performing in the Sunday talent shows I did it 3 times. I never won, other people had better talent than I but it was fun. I did this almost weekly for almost a year. I never ate before I went, I would have one mixed drink when I got there then switch to a non-alcoholic soda drink, because I knew I had to drive home. Sometimes on my way home, still dressed, I would go through a fast food eatery’s drive through, the dinning room area was closed, and get myself something to eat.

I then turned one bedroom into a combination storage room/studio by painting one of the walls of the bedroom pure white and building shelves to hold foam heads for my wigs and hang bags of jewelry off the shelves. I still need to get rid of the ceiling fan/light fixture and replace it with just a flat light fixture.
After awhile the DQs started cycling back through their costumes so I decided to take a break. That is about 2 years ago.

I recently made contact with two trans-gender groups. I have rejoined one which I was a member of in 2008. I have as of yet made it to a meeting of the other group.

I still do not go out dressed due to the nature of the community where I live.
That is the basic story of what I am doing. I have other posts that tell you about what I am doing.

[Maria in heels]

Leslie....
thank you for sharing your story with all of us. You have surely had some ups and downs, and that Chapter 3 was definitely very dark. Its great that you never appear to loose your "spirt" and have made your life what you want it to be, which is truly wonderful!

[Leslie Mary S]

I am thinking of going into the studio and doing a shoot barefooted because I can't wear any footwear due to an injured toe.
I might even try one in full make-up and wig. Maybe even do a makeup job like I used as an amateur DQ performer.

Then again most likely not.

[BostonBrenda]

I went to a store that did full makeovers, this was back when I was in my mid twenties. Seeing myself in a full length mirror as a woman changed me forever