Back in the days of yore, when I was a shy young lad of 14 years, I was curious. About a lot of things, really. Of course, the surge of hormones running through me was intense, as with most boys that age. I thought about sex frequently.
As with many youngsters of that time, I had already seen my father's Playboy and Penthouse magazines, and had graduated to the world of self-pleasuring. Even back then, I had the feeling that I was getting gypped on the whole underwear thing. The girls I saw in those pages had the most delightful clothes, and they looked so nice in them. Panties, bras, garter belts with stockings, I'm sure you've seen the fairly soft core porn that was prevalent back then.
So one day, the immediate object of my curiosity was, did my mom have that kind of lingerie? Don't ask where that thought came from, some random firing of neurons inundated in fresh testosterone, no doubt. Of course, given where I am today, perhaps there was a wee bit of estrogen there, too.
On the day in question, my family had gone somewhere, I don't recall where. I stayed home alone claiming homework. Once I was sure my family wasn't going to come back for some forgotten item or such, I went to my parents' room and started looking through my mom's dresser.
Now my mom was not, of course, a Playboy or Penthouse model. She didn't have tons of garter belts, stockings, corsets, etc. in her dresser. But what she did have was very feminine. (Mom if you ever read this, please don't get mad... or course, if you're reading this, it's hopefully because I've come out to you, so hopefully you won't be too surprised.) I loved the way the undies felt and I thought they were very sexy.
Now at this time, there was no internet, no support groups for this sort of thing. There were, however, rampant rumors going about the school about guys who liked to wear girl's clothes. Of course, it was always someone that someone else heard about from their cousin's friend's mechanic's babysitter or something similar, and always spoken of as shameful and bad.
For some reason, that day, as I was rummaging, that thought came into my head. What would it feel like? They felt so soft and silky in my hands.. what would they feel like on me? Maybe those guys that did it, did so because they liked it.
So what the hell. I hurriedly picked out a few things, pair of panties, bra, slip, and pantyhose. (Mom was definitely a pantyhose girl, no stockings or frilly garter belts.) I headed back to my room, closed the door and changed my life.
Ok, ok, I just changed my clothes, but that changed my life. I found that I loved the feelings. Panties, then the bra, then the pantyhose and finally the silky soft slip. Mom had always been kind of petite, and I was already about as tall as she was, so the items fit pretty well (with the obvious exception of the empty cups of the bra, of course). Being a fairly imaginative kid, I took care of that with some socks strategically inserted.
I kept running my hands over the slip, and especially over my legs with the hose on. I felt the air against my legs in a whole new way, and the slip swishing around my thighs was so sensuous. I went back to my parents' room and looked at myself in the mirror. Of course, I had fairly short hair at the time, my parents weren't wild about long hair on guys. No facial hair yet, so I looked, not exactly efeminate, but given the lingerie, I certainly wasn't the popular conception of masculinity. And there was, of course, the predictable side effect. I had an erection that was harder than any I'd experienced yet.
Yep, the sight of myself was enough to completely arouse me (and incidentally, kind of ruin the slim line of the slip). I had to finish. I took one of mom's nice skirts and blouses and put them on. No makeup, I had no idea how that all worked. (I still don't for reasons that will become obvious later.) I felt my chest with my perky breasts stuffed into the bra, felt my bottom inside that skirt; and I just HAD to get off. I didn't even have to actually touch my cock, just rubbing the outside of the skirt with the layers of soft feminine material was enough.
Of course, what else are 14-year-old boys famous for? Not thinking things through. Once I had come, I quickly realized that there was no way in hell that mom would not notice that there was something odd about this pair of panties. The pantyhose I wasn't worried about, mom bought those all the time and I doubt she had a current inventory of them in her head. But the panties were a different story. I quickly stripped and took them off. I put everything back where I found it as best I could and ran to my hamper. I knew the basics of how to do laundry at that time (i.e., I knew where the washer and laundry soap were, and what buttons to push. Kind of), so I grabbed some clothes of mine and, after I got my own clothes back on, went to wash the panties along with my regular clothes. Of course, I had no idea about separating colors, delicate fabrics or anything else. I dumped the whole load in the washer and turned it on. Taking no chances, I put it on the Extra Soil cycle.
Half an hour or so later, I went to put the laundry in the dryer. Most of the clothes were just fine. The blue jeans were good, my underwear was good, my shirts where ok. Mom's panties? Kind of shredded. Apparently they got caught on the zipper of my jeans and sad to say, were no longer wearable. Or really recognizable.
There is a feeling you get when you KNOW as a kid that your whole life is over and that there is no way out of your current predicament. I had that feeling in spades. I dumped the rest of the clothes in the dryer and took the now shredded panties out to the apartment complex dumpster personally, and buried them under as much stuff as I could without climbing into the dumpster itself. And then I went back to my room and sweated. I sweated for days. Weeks. Then I started to relax. I'd gotten away with it. Then I heard my mom asking my dad if he'd seen where she put her blue lace panties. Of course, I just stayed in my room reading and said nothing. Mom never asked me about them. But that was one heart-stopping moment.
So. I'd gotten away with it.
Over the next few months, I borrowed mom's clothes again from time to time, being much more careful about making messes. I was having a wonderful time until... (Cue dramatic music, spooky sound effects) I was in my room, dressed up again, when the phone rang. Back then, phones were attached to the walls, portable phones were expensive luxuries, and cell phones were a fond dream of the future. So, I had to answer the phone. This time, however, I had gotten really daring. I was wearing a pair of mom's high heeled shoes. A very nice pair of black pumps.
With 4 1/2" heels.
For the very first time.
On the second floor of the house.
(Cue Benny Hill music here)
I pulled up the panties, and started making my way to the stairs. I was doing all right until I started actually trying to walk down them. Of course, the heel on one shoe turned and I started falling down the stairs. I managed to catch myself, but for half a second, I could just see the TV news previews.
"Fourteen year old teenager found dead at the foot of the stairs in the family home, dressed in his mother's good dress and underwear. Film at 11."
I fell down two steps before I caught myself. I managed to slide down the rest of the stairs on my (pantied) ass and get to the phone. To add insult to injury, it was a wrong number.
I took off the shoes and made my way back to my room and changed back to my boy clothes, all thoughts of lustful pursuits quashed.
Of course, yet another thing teenage boys are infamous for. Not heeding warning signs. I figured, no harm, no foul. I kept on going, at least once a week after school I'd be in my room indulging in my favorite hobby, spurred on by being dressed in pretty clothes.
Then my father came home early from work.
Without going into details, suffice to say that my parents were from a culture where this sort of thing was, well... Frowned Upon (tm). Once again that feeling of my life about to irrevocably change and not for the better came over me. Images of military school (something my father had threatened in the past) combined with images of my ass and his belt danced in my head like hellish sugarplums.
I ran quietly for my bathroom (at least I learned that heels were a bad idea by this time), turned on the shower, and stripped madly. I stuffed the clothes at the bottom of the hamper in a wad (fortunately, I had put off doing laundry till I was out of clothes) and got in the shower.
The above paragraph was what I wrote initially. This difficult for me, but integrity compels me to be honest here. It wasn't nearly that easy and I didn't actually get away with it. The truth is... less amusing. While I won't get into sordid details, suffice to say that my father did catch me, and the humiliation he put me through was... intense. There are memories in our lives that are etched in our minds forever. For me, this is one of them, but not just the memory of the event. The horrible feelings of shame, of guilt, of self-loathing are stuck in my head. For the longest time, every time I looked at a pair of panties, every single time I ever bought a pair after that, they replayed in my mind like an endless loop of pain and shame. To this day, I can't hear the words, "faggot" and "queer" without becoming angry, and without that memory hitting me again.
This is why I'm so damn afraid to tell my wife. I don't want to live through that again.
And now, on with the story.
THAT incident scared me like the very real possibility of my own death by staircase had not. I stopped dressing for decades after that. I occasionally would purchase a pair of panties at the store ("They're for my mom."), only to feel incredibly guilty again and throw them away, occasionally without even wearing them. Things would happen occasionally to reinforce that guilt, as if the universe was trying to tell me something. A kid at school that I didn't know was caught wearing panties under his regular underwear at gym class. He was just a little too slow changing. He was ridiculed and shamed for months until his family finally moved away. He tried to say that his big sister made him do it, but she denied it all. It was quite the little scandal. So over the years, it became less and less frequent. The guilt did what guilt does and I eventually stopped. The last time was well over 30 years ago.
So, why am I doing it all again?
Well I came to a realization that I was having some bisexual desires. Maybe it's me getting older and such thoughts wandering in my head from time to time over the years. I started to enjoy bi and gay porn, and eventually found a video of a very pretty crossdresser enjoying the attentions of a guy. It turned me on a lot, so I decided that if I were to experiment, it would be with a crossdresser. Eventually, I did experiment, and found that I enjoyed it quite a bit from the single experience I had. I met a very pretty crossdresser at a local bar. Her name was Candy, and we hit it off really well. We talked at the bar till almost closing time, and she invited me home with her. I had already talked to my wife about possibly experimenting bisexually, and I was very comfortable with her, so I did. We went to her place and had very satisfying sex. Then, as we were cuddling afterwards, she asked out of the blue if she could dress me up. I was kind of floored! But I was feeling good, and safe, and secure, and I said yes. She didn't have much that fit me (she was kind of petite), but she did have a pair of black panties and some thigh-highs that fit, so she put them on me. I got very shy, since I wasn't shaved at all (legs and such) but she assured me I looked fine. We cuddled more and eventually we had sex again, and it was wonderful! I have long hair anyway, and she let it out of my ponytail and fluffed it up a bit and I felt perfect. I stayed with her till morning, and then I went home, happy and bouncy as all hell!
Now I'm not going to say that suddenly years of repressed memories burst forth or anything dramatic like that. I'd never forgotten about my dressing, but it wasn't something I thought about any more. Until that day.
So. Here I am. Doing it again. Wanting to learn the things I never had a chance to learn before, like how to walk in heels without experiencing sudden, violent death, and how to put on makeup. I've bought my own lingerie, and ordered my own pair of very modest heels (I'm leaving the 4 1/2 inch heels alone for now!) and here I go again. I plan on finding an online support group (which I wish I had had back then), and letting go of the guilt. I'm not hurting anyone, and it feels so right to me.
No, I'm not transsexual. I don't believe I'm in the wrong body. I know some transsexual people and they are wonderful people and I'm pleased to be friends with them, but that is not me. I don't ever want to be confused with them, not because I would be ashamed to do so, but because I don't want to cheapen their experience or their struggles. I'm sure I'll have my own struggles here and there, but they will be different. Maybe one of these days I'll come out to some of them and we can talk and learn more about each other.
What I want is to experience my own feminine qualities. I firmly believe that we are an amalgam of qualities. Many men deny it, but we all have a feminine side to us. It's part of the whole that is me. And I want to feel more of it.
I'm happy being male. I have children I'm proud of. I have a wife that I love dearly. Sometime soon I'll work up to telling her about this side of me. I trust her love for me and believe firmly that I won't lose that love just because of this. It will change things for us, how can it not? But I hope we can grow and love each other enough that we can get through this together.
So that's the end of my origin story. No radioactive spiders, no giant shelf of chemicals and a lightning bolt. Just a boy who was curious. And a man who loves occasionally letting the feminine side of himself out.