The First Time

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The First Time


by Andrea Lena Dimaggio



Donny stood in front of the closet across from the bathroom. At one time, it was used strictly for linens, but now held his mother's clothes as well. She and her husband no longer shared the marital bed, even though they had decided to stay together. This was the mid-sixties, and folks stayed married "for the kids," which proved to be a disaster in his parent's case because of his father's rage and their drinking.

The closet was an odd-looking one, with a door that reached from the ceiling to just about two feet above the floor, leaving the bottom of the closet almost like a bin. He opened the closet and looked inside, as he had many times before when he put linens away for his mom. The top three shelves still held the towels and sheets and such, but the bottom two shelves as well as the bin below were filled with neat piles of his mother's clothes. She had no dresser in the bedroom down the hall, so all of her "worldly possessions" as some might say sat neatly on the shelves in front of him.

He looked at the clothing, trying not to get too anxious. There was plenty of time; his father lay in a hospital bed nearly fifteen miles away, recovering from a heart attack; his second in two years. His mom had gone to see his dad and would likely be gone for hours. He had no immediate plans while leaving everything for later that night.

Reaching in, he probed where things were hidden, the hall light providing little illumination to the darkness of the closet. But what he sought was mostly in plain sight on the shelf just below eye level. He grabbed a pair of panties; white satin with a cotton crotch. A bra lay next to them, black with lots of lace and a front clasp, which would make it easier since he had never worn one. A white garter belt was found under his mom's undies. He was disappointed that nothing matched, but right then and there he would have settled for anything.

None of his mom's things matched. Maybe Aunt Agnes shopped at Bambergers or Sterns, but his mom was more likely to get her things one purchase at a time at Two Guys or Long John's Discount Clothing. It never really mattered to her if her clothes matched; she rarely wore anything remotely feminine, preferring drab slacks and loose sweaters instead of dresses and skirts. He would discover much later, after his mother's passing, just why she avoided looking pretty, but that's another story for another day.

Reaching in for the last time, he found the box that held her hosiery. This was a day when pantyhose was the "rage," but his mother usually wore knee-highs or socks. He grabbed three pairs of stockings that sat at the bottom of the box, trying to see in the dim hallway if they matched. When he replaced the box, his hand brushed up against the treasure; a find he hadn't anticipated. He pulled it out and looked at it.

A black satin full slip; its bodice covered by soft delicate lace, which was duplicated at the hem. The straps were thin and delicate as well. Feeling too embarrassed at the moment to hold the garment against him, he instead held it out at arms' length in front of him, marveling at the simple beauty of its design. He let out a breath as he bundled all of the clothes in his arms. His mother wasn't due back for hours, but he nervously hurried down the hallway toward his bedroom nonetheless.

His bed was disheveled; he and his brother rarely made their beds unless they had to change the linens, and then only reluctantly. He carefully rearranged the sheets and placed the garments in the pillowcase under his pillow and covered the bed neatly with his blanket. Moving over to his brother's bed, he remade that as well. The excuse would be that mom had been nagging him to make the beds. This way nothing would look suspicious, and his excuse was actually reasonable since his mother nagged him and his brother daily about it.



Night eventually came, and it was a time of anxiety as he wondered if his effort would be discovered. He worried needlessly. Even though he and his younger brother shared a bedroom, their sleeping habits were poles apart. His brother insisted on having a fan on at all times, even in the winter, finding the sound soothing. He on the other hand slept fitfully every night. He would discover much later in life the reason for his insomnia, which was born out of fear, but that is another story for another day as well.

He waited nervously for his brother to fall asleep; almost two hours just to make sure. He needn't have worried; his brother had fallen asleep within fifteen minutes after lights out, but he wanted to be sure. Donny understandably feared that any discovery would be disastrous. Once again, he worried needlessly. His brother was almost four years younger and rarely paid attention to him, preferring his own friends and interests. And he would discover, much to his surprise and to his mom's amusement that she knew all along that he had worn her clothes while he lived at home up to when he left for college.

"Mothers always know, honey," she had told him with a laugh on that late day in November. It was a secret that he treasured as a final blessing that she had given to him only weeks before she succumbed to cancer.

Feeling secure at last...or at least about half as nervous as when the night began, he slowly started to remove his clothing under his covers. He hadn't worn any socks, so he began by peeling back his tee shirt. He pulled off his underpants and used his foot to push them further under the covers out of the way. And then it was time...he had waited all week for this.

He wondered what the attraction was, but he never questioned it or looked into it; at least as a teenager at home. And where would he have gone? The libraries would have had nothing to offer for a boy who wanted to wear his mother's clothing. His sister enjoyed a special relationship with his mom, maybe that was it, but he didn't know.

Apart from the rare articles in old copies of Life or Look, the only information that was available on the subject was either in university libraries or in stores with paper-covered windows along with a warning posted at the door about having to be twenty-one to enter. So he had planned on this first exploration as a kind of rite-of-passage dressing walkabout, but with rayon and lace taking the place of bark and berries in a remote outback.

The panties came first. He didn't understand at the time, but it seemed natural to tuck his penis back between his legs before pulling the panties all the way up; the front looked odd, missing his normal contour, but something about it felt right. The bra came next. Even with the front clasp, he still fumbled putting it on, more out of nervousness than inexperience. He grabbed two of the pairs of stockings and filled each cup. Another odd feeling; he looked and saw that he had breasts; albeit soft and pliable instead of firm, leaving him with a feeling of comfort.

He grabbed the last pair of stockings and put them on. At fourteen he had leg hair but it was minimal and fine. He put on the garter belt; no experience seemed necessary. He figured the garment could be put on backward and turned around. As he fastened the tabs, he felt the hose twist and turn on his legs, which made him feel odd and warm and comfortable. His penis began to push ever so gently at first against the panties. He had experienced erections before, of course, but this was different and somehow felt special and shameful at the same time.

Reaching once again into his pillowcase, Donny removed the final key to his adventure. He pulled the slip over his head, making sure to align the cups with the bra, and he smoothed the garment down his body, the hem reaching just below his nylon-clad knees. It felt good, but it provoked more nervousness, and he peered over at his brother's bed. He forgot where he had left his glasses, and he strained in the dark wondering if somehow he was missing his brother's waking stare. Again, he needn't have worried. His brother slept through the night and many other nights for the remainder of the year, blissfully unaware of his older brother's newly acquired habit.

It had started to rain, and the wind caused the raindrops to play a staccato rhythm on the window next to his bed. His cat had hopped up and positioned herself on his back while he lay on his stomach, her claws alternating digging into his shoulder. He propped his head on his pillow, which lay against the window frame as he looked out and down the street. Her house was about fifty yards away, and he wondered if she was sleeping. What had she worn to bed?

He was fourteen and Liz was nearly twelve. Apart from the kid-down-the-street dialog every day, he didn't dare to talk to her. Even if he did, what would he say? He didn't have a clue. And of course, what would she think of him now? Sitting in her dining room playing cards with her sister and her was one thing. What would she say if she saw him now? Playing stickball in the apartments across the street had to be entirely different than sitting across from her wearing a dress or a skirt. Would she laugh? Would she shout and tell him to leave? Would she still want him as a friend?

He reached down and found his glasses that had fallen into one of his sneakers. Putting them on, he looked once again down the block, straining to see the light from her bedroom. He loved her, such as it was for a fourteen-year-old boy in his mother's slip and panties on a Thursday night in early October. He bit his tongue as the tears began to fall just as freely as the rain outside his bedroom window. He hated himself, and he surrendered to the shame, laying his head on the window sill. He was filled with guilt and sadness, and he thought about just how horrible his life had become. And he wept.

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Comments

Sad

It's sad,in keyword is "Auto-Biographical Non-Fiction" and that mean that really was in you past?

It's not easy

having feelings that you can't talk about; back in those days, there was no information, no guidance.

This is not living; it is merely existing.

Andrea, you sum up so well all the feelings of self-loathing and hopelessness that beset many who suffered similar agonies. It makes me respect, all the more, those who had the courage to leave that life behind, set out into the world and search for fulfilment of their dream, often against immeasurable odds.

Susie

'Drea,

I grew up in the Sixties too. If I could have, I'd have been there for you.

    Stanman
May Your Light Forever Shine
    Stanman
May Your Light Forever Shine

Wonderfully well written

That was a very sweet and well told tale. I loved it.

So very sad

I know all too well the furtive dressing of a teenager when she has the house for a few hours, so this did indeed resonate with me - very melancholy but well written - take care - Jay


That which does not kill me only serves to delay the inevitable. My blog => http://jaym.angelblogs.co.uk/

That which does not kill me only serves to delay the inevitable. My blog => http://jaynemorose.wordpress.com/ <= note new address

Dressng !

ALISON

Andrea,I am so pleased that the comments echo your lovely,little story.You can add me to that list.Thank you so much
Alison.

ALISON

Relating

terrynaut's picture

I can relate to this story all too well. I spent many, many days and even whole weekends dressing in my mother's clothes. I'm an only child and my parents often left me alone while they went off to work on a vacation home or a friend's vacation home. In a way, I was lucky to have so much free time alone. But I also had a lot of time to think.

I felt the same sadness, wondering if I was a freak and imagining what friends and neighbors would say if they knew. I also felt intense sadness when I had to change back to my boy clothes. The more I dressed up and the more feminine I looked, the harder it was to change back. I tortured myself, but I couldn't help it.

There's one difference between your story and mine. My mother never knew, not until I told her not all that long ago. I think she must have had her head in the sand but she didn't have a clue.

The onle one in the family who knew about me was Porky, my dachshund. At least I think he knew. The first time he saw me completely dressed in my mom's clothes, wig and makeup, he thought I was her. He gave me his happy dance that he used to welcome my parents home after they'd been gone all weekend. I can look back at that particular incident and laugh now, but it was awkward at the time.

Thanks for sharing a very personal moment and showing me once again that I'm not alone.

Hug

- Terry

don we now our gay apparel?

laika's picture

My first times were when my mom had gone to the store, real rushed experimentations. I remember I hated my mom's clothes, but they were what was available. The brassieres were nice because they gave me boosums, but she only had a few things that I liked, that didn't seem square. I didn't wanna look like some housewife but ....... I dunno. Bridgette Bardot? Goldie Hawn? Definitely not Ruth Buzzy! (Guess who else grew up in the 60's...). Did I feel guilty and weird about it? Hell, I ALWAYS felt ashamed and weird, so this didn't seem worse. Probably better in fact. Somehow I aquired a nice white cotton peasant blouse with rich colorful embroidery, and a neat funky necklace, and her skirts didn't seem so bad with them, which was great because when I turned 15 or 16, like Terry's folks they would go off (to Vegas) for the weekend and let me babysit myself. I had developed a taste for pot and beer by then, so these dressing sessions were combined with that and these nonsensical "conceptual art" projects. I was a weird kid in plenty of ways, and if I were to write a story about this time of my life (although there's a little of it in my Jackie Kaiser stories), my identity development, it wouldn't make much sense to anyone, even me. But I like this one, Drea Dear it's basic and honest, and if I had a time machine I'd love to go back and tell the kids we were there was nothing wrong with us, all that, but I don't seem to have one so I'm telling you now:)

The WEIRDEST thing I ever did with clothes didn't involve crossdressing. I was in Jr. High and I really yearned to get laid by a guy. It was common schoolyard knowledge that queers wore Hawiaain shirts and white socks, so one time I dressed like this and went out hitchhiking, expecting some chicken hawk to read my "gay" outfit, give me a ride and wind up screwing me. Didn't happen. Talk about a lack of information in those days. I'm glad the schoolyard rumor wasn't about wearing snowshoes and a lampshade on your head! Embarrassing but somehow hilarious to me, that I was that dumb about things...
~~~hugs, Laika

.
The closest approximation to what it's like in my brain:
https://www.youtube.com/watch?v=u08E7c-FRbU&t=4s

"Troll?" the ancient yuletide carol...

Andrea Lena's picture

...We were okay, weren't we? This story seems to have struck a nerve with some. Someone close to me had asked me how I got started...and after weeks of other ideas and stories and comments, this came back to me, as a lot of memories have been recently. And I wept today as I wrote it, because it isn't nearly as sweet as I remembered it. The girl down the street ended up marrying me...we were together as neighbors..then boyfriend/girlfriend..childhood sweethearts... then engagement...then marriage...then sad and cruel behavior to her...then divorce...and only then did I get help. She remarried a great guy just about the time I met my wife. And she's the only person on earth besides my counselor in RL that knows about Andrea.

This one was very hard to write since everything I remembered was sad and disappointing and shameful instead of exciting and new and wonderful. But one thing has changed, and it is big and wonderful and a blessing. I have hope!

By the way, something came to me today about our relationship as friends and sisters. Even though I've only known you a short time, it feels as if we go WAYBACK!

Special thanks to everyone who commented. This was a story I wrote more for me than anything, but I'm glad if saddened by our similar experiences that you were blessed by this. But like Laika said, we were really okay, weren't we? God Bless!

She was born for all the wrong reasons but grew up for all the right ones.
Possa Dio riccamente vi benedica, tutto il mio amore, Andrea

  

To be alive is to be vulnerable. Madeleine L'Engle
Love, Andrea Lena

Dear Sis...

I am so proud to know you and to have you in my life. Your bravery and courage have no bounds and what you write strikes something deep in all of us...well...maybe MOST of us. You never fail to surprise me with your total, and sometimes brutal honesty.

May We Share In Your Courage...

Your Lil' Brat Kelly

P.S. I love your blouse...

I Identified So Much.

jengrl's picture

I remember those feelings so well growing up. I was so scared that others would think less of me if they knew my secret. I lived in fear that my brothers would not take it well either. My Paternal grandparents were deeply religious and I just knew they would never have accepted me. I had to wait until they passed before I was able to be my trueself. I wish that they could have met me as I am and loved me as their granddaughter. My Maternal grandmother has been wonderful to me. My first Christmas fulltime, she sent me some steamy romance novels for my reading pleasure LOL! This story is told with heartfelt emotion and I appreciate you sharing it with us Drea'

Hugs,

Jen

PICT0013_1_0.jpg

I do agree that it is sad

that society places such narrow rules about gender behavior and dress. But if we are proud of ourselves, if we know who we are, and we stick to the belief that everything we do is right for us, then that is what we must do. I am writing the second book in the Chrissie trilogy. When it is finished you will see just what happened to a lot of teens in the 60's because of prejudices, misunderstandings, and total bigotry.

This was written very well, and the guilt and hesitations are normal for a boy and still are today even though society's attitudes are changing in our favor. Thank you for sharing.

"With confidence and forbearance, we will have the strength to move forward."

Love & hugs,
Barbara

"If I have to be this girl in me, Then I have the right to be."

"With confidence and forbearance, we will have the strength to move forward."

Love & hugs,
Barbara

"If I have to be this girl in me, Then I have the right to be."

You Knew Me!

joannebarbarella's picture

How well you have captured that torrent of emotion and misery and mixed feelings and compulsion and shame that were our lot when we first discovered ourselves.

In those days and earlier (in the fifties) there was no-one to confide in or talk to. I know I thought I was probably the only such freak in the world,

Joanne

All Dressed Up. . .And

Not only were we taught that people like us (different) were horribly bad and destined for Hell, we also were made to believe that everything was linear. Every action was a route to someplace. The United States was on an ever bettering course. No one faltered, but us.

Our dressing had to have some purpose . . . something. For those of us who knew that trying to get laid, like Laika suggests, would mean eternal damnation, the dressing was especially forbidding.

It would be over forty years after my first experiences before I could find peace in simply allowing my feminine sprit to flourish. When I looked in the mirror at WHO? I wanted to now WHY? I wanted to know WHERE all this was going. There was NO ONE to tell me and EVERYONE to hide it from.

We all stared into the rain and felt the wetness on our faces.

Beautiful writing that stirs the ashes of a singed youth.

Angela Rasch (Jill M I)

Angela Rasch (Jill M I)

So Alone Among So Many!!!

Ole Ulfson's picture

It's such a shame, Andrea, that none of us knew each other back in the '60s, '70s or before. We are all here now and can provide the support we needed when we were kids. That's when we needed it the most. But we all carry the children we were with us. Like most of us I knew about myself when I was very young and got caught early and often. but you're right, it was always gleeful anticipation followed by letdown and sometimes, self loathing. Oh how we punish ourselves!

You and many others here have suffered so much more than I. It makes me want to help but I don't know how. You're a wonderful person and an inspiration to us all.

God bless you,

Ole

We are each exactly as God made us. God does not make mistakes!

Gender rights are the new civil rights!