Monday, January 22, 2024

Second Time

After donning my mother’s nylon stockings and high heel shoes and discovering that I was able to emulate the shapely legs of a woman, I just had to push the envelope further. The next time I was home free to explore my mother’s wardrobe, I repeated my first time, that is, I slipped on a pair of her nylon stockings and high heel shoes.

I was well aware of the options available to women of the early 1960s to keep their nylons up and their seams straight. In my mother’s case, she used the garters that were attached to a girdle. I found her stash of girdles in a drawer of her bureau and had to choose from a variety of styles: open bottom, panty brief, long leg panty, high-waisted panty and high-waisted long-leg panty. I figured I needed all the help I could get, so I selected a high-waisted long-leg panty model.

I unzipped and unclasped the girdle, stepped into it and tugged it up over my legs, hips and waist. When I was finished squeezing into it, I closed its clasps and zipper with some difficulty. When I was done it felt like half of my torso was in the grips of a rubber vise.

After I attended to the nylons – straightening their seams and attaching them to the garters of the girdle – I swung open the closet door, viewed myself in the full-length mirror and concluded that the picture was incomplete.

The girdle had redistributed my “baby fat.” As a result, my waist was narrower and my hips were wider, but above the waistband of the girdle, a ring of displaced fat encircled my body and ruined the picture.

I was sure I knew how to fix it – it was time for my first bra!

My mother had a small selection of bras to choose from and they were all similar in style and size, so I randomly grabbed one and tried to figure out how to put it on.

I struggled unsuccessfully to close the bra’s clasps while wearing the bra with its cups in front. So, I slipped the straps off my shoulders, twisted the bra around with the clasps in front of me, closed the clasps, twisted the bra back around and slipped the straps over my shoulders – and that’s the way I have been putting on a bra ever since.

After adjusting the straps of the bra, I was astonished that my breasts nearly filled the cups of the bra! My “boy boobs,” which were the object of ridicule by my peers, now had a safe place to call “home.”

And when I revisited the full-length mirror, the picture was now complete; there was the body of a shapely woman in the mirror’s reflection.

By the way, recalling my second time crossdressing, I realized that the event occurred in 1964 – 60 years ago. 

And so time goes.


Source: Bebe
Wearing Bebe


Frederick Weller
Frederick Weller femulating in television’s In Plain Sight.

22 comments:

  1. I thought I was all alone when I went through almost exactly the same ritual so many years ago. Your story brought back two memories. One incident: my mother had gotten a new girdle that was a bit too small one day. She asked me if I would wear it to stretch it out. I thought for a second and told her no, as I was afraid of being found out and felt ashamed of my cross-dressing at the time. I wish I would've taken her up on the offer. The other thing that comes to mind from your post is 60 years. We've been doing this so long; it never goes away. It's always been there, which is really amazing. It's good to know that I'm not alone. Have a good day, sister. Paula G

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  2. Oh yeah, me too! The stories are usually similar, only the dates change to reflect the individual.
    Also, I watched every episode of IN PLAIN SIGHT but somehow missed Marshall in Drag. I have to go back now and find this one.

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    1. Season 5 Episode 5. Drag me To Hell.

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  3. In 1964 I was 16 an only child. Dad worked days so a lot of me and Mom time and summer vacation. My Mom looked exactly like the photo plus half or full white slip. From the only I knew then file. I would have done things different but it was the ‘60s I didn’t dare to even think those things. My Mom received a birthday gift from her sister a pair of rayon PJs. She needed a large size but embarrassed to return them to a local store. She said I could have them. Not like the cotton or flannel I had. For years I tried to get that same feeling again. Wasn’t till I retired I’ve had a chance to capture that feeling being married I’m cautious. Dabbling with some women’s clothing hoping to extend further

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    1. Only if that sounds so familiar! If I knew then what I know now. Story of my life.

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  4. Wow, we are almost identical in every way. But I was afraid to use the stockings for fear of making a "run" and I would be found out! Greatly appreciate our sisterhood.

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  5. I'll bet a lot of us thought that description was about us I know I did. I may have gone for the bra first and then the girdle to hide that unsightly bulge

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  6. Every time I see photos of "old-fashioned" underwear like this, I reminded of all.the time I spent looking through the Sears catalogs in the 70s as a boy, pretending to look at the toys and boy's clothing, but secretly admiring all the women's clothing and underwear and pantyhose...even at that young age wishing it was something I could wear.

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  7. Sure looks like this story hit home with a lot of us 70+ guys remembering days before panty hose, letting the girdle serve two purposes holding up those stocking we dared to try on and at least reduced my boy part to a little bump and most of us put our bras on just like you said still to this day. thanks for the memory and a smile on a winter's day.

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  8. That's how my wife puts on her bra also!

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    1. I actually taught my wife to put her bra on that way!

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  9. I think when I was 12 and dressed up for the first time my mother was already wearing pantyhose. However, for that first time I raided a back bedroom closet in which I found a panty girdle and nylons. Quickly I rummaged around and found garters to attach to the girdle, and I put it on. The silky smoothness of the garment felt wonderful! Next I pulled on nylon stockings and clipped them to my garters as I'd seen mom do many times before. There was also a silk slip which I put on. Next was a bra which I struggled with and eventually figured out the "clip it on backwards" and bring it around method. I stuffed some socks into it and chose a dress to try on. It was an old silk and chiffon cocktail dress which fell a few inches below my knees.

    It all felt so perfect! I stayed in that outfit for as long as I dared. Fearing my parents would return I took everything off and carefully put the garments away. Deep shame filled my mind. I feared that anyone, mom, dad, and friends, would realize what I'd done as if I was The Scarlet Letter's, Hester Prynne.

    I swore I'd never ever don girl's clothes again. I believed since no one had ever seen me in feminine attire it had never taken place. I broke that promise to myself many times. It took years to stop feeling guilty for those desires, but it's still a desire over which I'm terrified people might discover. I don't think I'll ever shake off that feeling.

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  10. As a child of the 1950's and 1960's I grew up in a repressive society. I could not figure out why a young teen kept going into his mother's lingerie drawer. I routinely wiggled into one of her open-bottom girdles and attached a pair of stocking to it. One day I had an appointment for a physical for a job with United Parcel. I had spent the morning alone at home wearing a very snug girdle. When I took it off all the seams had made impressions on my body. Yikes! I kneaded my skin to get the impressions out. I did not know remember if they disappeared by the time I arrived for that physical. I did not have the guts to look down during the physical. Now? I have a nice collection of foundation garments. My favorites are two shaping slips in black and white. Unless I go out it's a garter-girdle with stockings under my dress and full slip.

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  11. Melissa RobertsJanuary 23, 2024

    My crossdressing life began when I was 8 years old. Beginning when I was around 12, I had the very fortunate luxury of having access to my friends moms wardrobe, her name is Rita. They had a vacation home and spent a great deal of time there, especially in the summer. They didn't always bring their dogs with them so I volunteered to house / dog sit. I could go there and dress up all day long if I chose to, which I often did. I could write chapter after chapter about this experience but for this post I'll hone in on my first girdle experience. So after about two years of wearing Rita's clothes ( mostly panties, bras and other lingerie) Up until this point I had only focused on the lingerie drawers of her dresser but then I got curious and started rummaging through her closet. In the back of the closet there was a plastic bag so I opened it up and discovered two girdles, some stockings and some very pretty nighties. Already wearing one of her bras and a pair of her panties, I took one of the girdles out of the bag. It was a white open bottom with a side zipper and had four garters. I unzipped it part of the way, stepped into it and slid it up my body. It went on very easily over the silky nylon granny panties that I was wearing. I pulled up the zipper and the feeling was absolutely amazing. It cinched in my waist and instantly made me look more girly. I ventured further and after a short struggle, I attached a pair of nude stockings. I admired myself in her full length mirror and felt like I was a pin up girl.

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    1. Hi Melissa, This is a wonderful story and reminded me of something similar that happened in my life many years ago that I had totally forgotten. I was a young teen and my neighbors, who had a daughter a few years older than me, were away and asked my parents if I could water their plants for them. I now recall spending so much time trying on the girl's clothes that my mother was worried there was a problem at the house. Thank heavens she didn't come over and see her son in a dress, nude pantyhose, and too big shoes!

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  12. As a 70+ crossdresser I vividly recall the ritual you so accurately described. There was just something about underwear back then that is hard to duplicate today, especially those girdles, they were uncomfortable and sexy at the same time!

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  13. It amazing how the bra cups gets filled up without much effort on us so called boys.

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  14. Does anyone happen to know the brand of the gorgeous bra and high waisted girdle?

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    1. Sorry, but I don't know. The photo was just a random photo I found on the Internet.

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  15. I suspect Sears or JC Penney! Bottom shaper with the power net?🥰

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