The First Time

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The First Time

by Andrea Lena Dimaggio


He 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 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 Alice 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 really never mattered to her if anything 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 up in front of him, marveling at the simple beauty of its design. He let out a breath as he held all of the clothes in his arms. His mother wasn't due back for hours, but he 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 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. Any discovery would be disastrous he had thought. Once again, he worried needlessly. His brother was almost four years younger than him 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 the he had worn her clothes while he lived at home all the way up to when he left for college.

"Mothers always know" 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 just before she passed.

Feeling secure at last...or at least about half as nervous as when the night began, he slowly started to remove his own 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. And the only books that were available on the subject were either in university libraries or in stores with covered windows and the warning at the door about being twenty-one. So he had planned on this first exploration as a kind of rite-of-passage walkabout, but with rayon and lace taking the place of bark and berries.

The panties came first. He didn't know 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 looked 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. But he felt good.

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 was necessary. He figured the garment could be put on backwards 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.

Reaching once again into his pillowcase he removed the final key to this 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 she was nearly twelve. Apart from the kid-down-the-street dialog every day, he didn't have the courage 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 rummy 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 in 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. He bit his tongue as the tears began to fall as freely as the rain outside his bedroom window. He hated himself, and he gave up, laying his head on the window sill, weeping quietly. He was filled with shame and sadness, and he thought just how horrible his life had become. And he felt hopeless...

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