More of Jill Bradley…
I know you panty boys enjoy these stories, ’cause you have told me so! Surprise, here’s another awesome story by panty boy, Jill Bradley! I hope you enjoy the element of surprise as much as I did…and, thank you, Jill!!
The very first recollection was when my mother thought it would be cute to dress me up as a little girl for a Halloween party when I was 5 years old. She had long boasted that I would make a lovely girl. She talked often with other women about what a pretty girl I would have been, and dressed me as a girl to take me shopping as a small child.
So when she dressed me for the Halloween party, she knew exactly what to do. She put my hair in ribbons, put me in pink panties, a petticoat and a taffeta dress. She put on lipstick and rouge, pink socks and Mary Jane shoes. I won first prize. No one recognized me. It was a church Halloween party. She was so proud of her little girl. I am sure that made a big impression on me.
My dad was overseas, serving in the Philippines, so he didn’t know about the party until he got back. If he had a reaction, I don’t know what it was, but although she didn’t dress me that way any more, she really enjoyed telling the story and of her pride in what a pretty girl I was that day.For years, I had spent long summer hours when at my grandparents house, I perused the Montgomery Wards and Sears and Roebuck catalogs. I would be staying at their house, waiting for my Granddad to get off work at the railroad. My Grandma was a semi-invalid, so I had little I could do. The pictures in women’s clothes really captured my attention. I was most curious about the panties, girdles and nylons with garter belts.
When I reached puberty, at about thirteen and my hormones didn’t know what to do. There was no real sex education in those days (The fifties). I began to really want to do something about the panties, girdles, slips and garter belts I saw in those catalogs. In each of the catalogs, there were sizing charts. I learned that Marilyn Monroe’s figure was 36-26-36 and that was the ideal figure. I wanted to have that figure! So I often borrowed my mother’s tape measure and went into the closet to take my measurements. I was 36-28-33. Wow! I would draw outlines of my “curves on large pieces of paper comparing me to Marilyn.
When my dad got orders to go to Alaska, we were to join him, but spent 3 months in Seattle in preparation for our reunion. There I met a girl my age, now 14, we were both smitten. I told her about my “curves’. We measured each other. One day, as we were playing in the front yard, she ripped her shorts, revealing pink, nylon panties.. When she came back out to join me after changing shorts, I told her that I wished I could wear panties like that.
Instead of saying something like, “Boys don’t wear panties”, she said, “Do you want to see them?”, She turned down the side of her shorts to reveal the top band and the pink nylon panties. “Go ahead and touch them! She said. I felt the smooth nylon and was immediately hooked. I had to get me a pair.
In those days, teenagers did not have any expectation of privacy, like many do today. My mother inspected every square inch of our rooms, not to be snoopy or intrusive, but to teach us neatness and organization. It was a military family, after all. One time, I bought a copy of “Battle Cry” because there was a sexy scene in it that would be nothing today. My mother found it and confiscated it. So I knew that there was no way to keep any women’s underwear. By now, her expectation of me were all about being a real boy, so there was no playing on that.
We moved to Alaska and lived in a cabin in the deep woods until my dad could secure quarters on the base. We were there for my entire 9th grade year. It was great, because I was left alone on several occasions while my mom walked over to visit with a friend of hers in a nearby cabin. From her bedroom window, I could see her walking over to that cabin and back. I invaded her lingerie drawer. Everything was white, no pink available. But it was almost all nylon and a perfect fit for me. I don’t have to tell my fellow panty boys what that moment was like, when I first donned those panties. It was ecstasy! Putting on a bra and a full-length slip was even better, because of the sliding of the materials over one another. I soon began donning garter belt and hose (this was before the day of pantyhose).
I could always tell when mom was coming back from the neighbor’s cabin. There was no cleared path, except by her footsteps, so it took a full 10 minutes for her to return, and I could see her the whole time. So, if I was even fully dressed, I had sufficient time to remove the clothing, fold it up carefully and place it back in the drawer or on the hangers in the closet.
I was never sick, but I feigned sickness a few times, just so I could invade that drawer and closet.
After we moved on base, my opportunities to dress were very rare, that is, until my mom set me up with babysitting jobs to obtain spending money. Here is where I got very daring! On several occasions, after putting the children to bed, I would go into the parent’s bedroom and dress up in the clothing of the lady of the house. Most of the time, these were officer’s wives, Captains, Majors, and once, the Base Commander. I don’t know how I did it, phenomenal luck, with no one coming home early might be one, but I am grateful, because, my father was an enlisted man. He would have caught the brunt of it and passed it on to m. At school, I would be ridiculed beyond belief. It retrospect, I should have been more frightened, but it just goes to show how strong the drive can be.
We moved back to the lower 48, and I had only a few rare occasions there. By the time I met my wife, I had decided to give up my “fetish” as the library books I found called it. Or, worse yet, it was often called a “perversion” in the literature.
A little over a year into our marriage, I discovered, quite by accident, a garter belt. I was cleaning out a room in the Student Union of the campus where I was a custodian. I immediately such it in my pocket and took it home at the end of the day. I had no idea how I was going to explain this to my wife, but the desire to wear women’s clothes had returned with a vengeance.
That night, while in bed with my wife, I told her about my strong desire to cross-dress.
Her answer must be the answer that every panty wearer or lingerie-loving man would want to hear. She hugged me and reassured me that it was fine. We were on a very limited budget, so I asked if it was OK that I buy a pair or two of panties. She said yes, and suggested that if I wanted any outer clothing, we might try the Goodwill Industries in the town.
All of the time the kids were growing up, I was very discreet about dressing, usually just dressing in all male attire. I purged a few times, but my wife had a way of hiding the purged items until I changed my mind and they reappeared.
After years of guilt for my feelings, I finally went to see a professional counselor. He was very understanding, and accepting. He assured me that there was nothing wrong with my feeling and behavior, he saw that it made me a more sensitive person and that I would make a good counselor myself.
I began to be able to enjoy my “hobby” guilt free. It was more than a “hobby” however, I am convinced it is a part of me, just as my love of baseball is a part of me.
Since retirement, I have more fully embraced my feminine side. I wear women’s jeans, shirts and slacks, and always, yes always wear panties underneath–no male under wear. I always sleep in silky nightgowns and wear girdles and hosiery under my clothes in the winter time. I also take jewelry-making classes with my wife. She is my wife, my lover, and my sister, all wrapped into one.
As many young people do, I went through a period of blaming my parents for my own shortcomings. But I want to say this; I am so grateful to my mother for the Halloween party. Not only was she proud of her “little girl”, but she was proud of every one of my achievements in my male life, whether in music, sports or my career. She is gone now, but I love her very dearly, and my feminine side came from her. I am sure that now she is equally proud of this boy and this girl.