What Might Have Been

[Author's Note: This story almost wrote itself. A dear friend of mine's brother died suddenly and I was helping her clean out his apartment. Almost hidden away in the back corner of one of his dresser drawers I discovered he had a secret. A secret that was definitely the sort of things you'd never want a family member, let alone a stranger to find. That kind of embarrassment would kill someone. (Sorry. Bad pun.) I knew enough about him to know that he and his wife divorced a few years ago and had been living by himself. So these things most certainly had belonged to him and no-one else. Not wanting to hurt or shock my friend by revealing her brother's secret, and as there was no value to what I found, I quietly and discreetly stashed the neatly folded items into my bag. I would deal with it back at my house. Once home, I found that I could neither destroy nor dispose of my find. Not without closer examination. From a what looked to be a page torn from an old personal journal (No doubt kept as a reminder of his younger days.) along with the other 'special' objects I was now in possession of, this story was born.]

What Might Have Been

I was bored. And when I become bored my mind gets busy. I was in a mischievous mood and looking to break things up a bit.

I was hanging out at my girlfriend's house. Her parents and sisters were out who knows where so we had the place to ourselves. But instead of taking full advantage of our situation, she was gossiping on the telephone with her best (girl) friend leaving me to my own devices.

Wandering into her bedroom I saw, fresh from the drier, a pile of her clothes lying there. As a teenager who had no sisters and virtually no prior intimate interaction with girls these were too interesting to resist further inspection. Most especially the bras and panties.

Barb and I had been dating for a couple of months. We hadn't gone "all the way," but things had been progressing nicely between us. So here I was, staring at this mishmash of white and pastel "unmentionables" knowing full well that we had the house to ourselves for at least the next hour or so and it was evident she would be on the phone for a while to come.

As someone who had no sisters or other female relatives near my age, curiosity and a devilish nature told me I shouldn't pass up such a golden opportunity for exploration. With trembling hands I picked up a pair of panties, surprised at how soft they felt then by how light they were. These were your normal, average, everyday cotton briefs for girls, yet they were still lighter than my Jockeys. But how thrilling it was to be touching and examining them, some with dainty little flowers or butterflies.

After inspecting several other pairs I moved on, to her bras. I took notice of just how soft the tiny, slightly padded cups were compared to what seemed to be unnecessarily stiff and somewhat scratchy straps and elastic banding. All the same it was very thrilling. I even took the time to figure out just how the hasps worked.

Also spread out on the bed were a couple soft, lightweight blouses plus a short skirt.

My girlfriend was on the kitchen wall phone still fully involved in their girl-talk and I figured it was about time she pay some attention to me. Best to cause a distraction.

It took her a moment before she looked over to where I was standing, and then almost dropped the receiver. There I was bare chested -- other than wearing one of her bras. A little snug around my ribs and the shoulder straps adjusted far too short, I know I looked absolutely ridiculous.

Caught off guard she allowed a guffaw to burst out before catching herself not wanting her friend know what I had done. In high school rumors spread quickly.

After doing a few poses while beaming from ear-to-ear I headed back to her bedroom.

Evidently I had not caused enough of a distraction because the gossiping resumed. It was time for drastic measures. And I was in just the mood to provide them.

Off came my sneakers and jeans. I gotta tell you, 18 years old and standing in my girlfriend's bedroom wearing nothing but my briefs, socks and a bra was kinda scary. And quite exciting too.

On went the frilliest blouse over the bra then I shimmied into the skirt. Though the blouse had some stretchiness it was still snug and showed the bra underneath. Fortunately my hips were about the same as hers so the skirt fit okay. The reflection looking back at me from her dresser mirror was shocking. But in a spooky, good way.

Just as I was about to make my big reveal I had an "oh, what the hell" moment. I slid my briefs out from under the skirt and pulled on a pair of her panties. (My parents always said, if you're going to do something, do it right. Thank goodness they weren't here to see this.) I knew what I was doing was SO WRONG yet it gave me such a thrill -- and one powerful erection.

Without thinking I twisted my hips back and forth a few times while watching my reflection and feeling the skirt swish brushing my legs. NEAT!

As quietly as I could I snuck down the hall to the kitchen. The hairs on my exposed legs tickled as the air and skirt brushed against them. The hairs on the back on my neck stood at attention. For some unexpected reason, being dressed in in girls clothes was ... thrilling!

Barb had her back to the doorway, her feet up on the chair next to her. When I was ready I sauntered over to the refrigerator, opened the door, bent over, and removed a soda. The room went silent.

There before her disbelieving eyes was her boyfriend, not in his own clothes, but wearing her things! A frilly blouse and a skirt!

Opening the soda and looking at her as if this was all quite normal I watched for her reaction. At first I thought she was mad, possibly disgusted with me. And who could blame her. She's been dating a guy and suddenly he's dressed as a girl. [Uh oh, I've made a very big mistake.] I began to panic, my mind a whirring jumble formulating an excuse, when she suddenly gets this giant grin while stifling laughter. It turns out she thought it was hilarious. She just didn't want to let on to her friend what she was witnessing.

Feeling a bit of relief, I timidly did a little dance for her. Barb's smile only grew bigger. Now my head was back in the game, and enjoying a euphoric rush. And before heading back to change I flipped the back of the skirt to show her I was even wearing her panties. My heart was racing, but that was all it took. As I headed back to change back into my clothes I heard her tell her friend she had to go.

Even though a little part of me hoped she would stop me, I hastily changed clothes knowing that her family could return any moment. (At this point, we still had not seen each other naked so I changed behind a closed door.) But that didn't stop us from laughing and joking as I changed.

But what about those strange feelings I had? Were my emotional and physical responses due to putting on girls clothing instead of the clothes that matched my gender? Was it because of the texture and feel of girls material? Did it have to do with the snugness of the bra, the incredibly soft panties and airy freedom around my legs? Or was it strictly because I was doing something that was out of character for me and would be shocking to my girlfriend? All I do remember is that it caused such a rush of adrenaline along with a variety of feel good endorphins that had me feeling pretty high at the time.

Sadly, that was the one and only time I ever came close to cross-dressing while we were together. Three-and-a-half years after that day we married. And as funny as she thought what I'd done was, and the unexpected physical effects it had on me, in the 16 years that followed that day, the subject never came up again. As such, cross-dressing was never explored again.

Only in the years since we parted ways, I have 'played' with several pairs of panties and a couple thongs. (Nervously, I told the cashier they were for my wife.) I often dream of going all with bras, blouses, shirts, and high heels, but could never work up the nerve to actually go clothes shopping for women's wear that would fit me. Sometimes I even wonder what I'd look like with makeup.

Anyway, these panties I did buy are all very sheer and kind of showed off my little man. (I have this twisted dream of being forcefully placed in some sort of social setting, my lower half covered -- but not really -- by these semi-transparent panties. Everyone noticing and commenting on my lack of endowment.) Masturbation heaven!

Hmm!? Could I really be and exhibitionist who desires to be humiliated? It sure seems to light my fire.

This all leaves me to wonder if at some point, especially after we married, had I just once more thought to surprise her that way again, would she/we have decided to play that game more often? I have a feeling that just maybe she'd have encouraged it. She was, especially in the early days, a bit adventuresome. It's fun to imagine that she would have gotten me my very own training bra daring me to wear it to work under my suit. After that you know it would have led to me also wearing panties, possibly full time. And back then I was still wearing my hair fairly long. Who knows what she might have done with that? Would I have ended up with a closet half filled with men's wear and the other half...? And just where might any of that lead from there? It's almost too painful to think about now.