We resume the story with our intrepid heroine about to enter her teen years and experience the joy of her first period, breast growth and discovering boys. In your mind you should now hear the scratching sound as the DJ hastily lifts the needle off an old LP record just before the crowd turns around to stare. Our unfortunate heroine had none of those delights to look forward to, but rather the twin tyrannies of massive height expansion and needless hair growth in places entirely unbecoming.
Not that I knew what to expect at the time, or even that what was happening was wrong. It was just what everyone had told me was supposed to happen. I never had the sense of identifying strongly as a girl when young – though honestly never really felt that I fit in as a boy. I was too big to beat up, too shy to find and too smart to get into trouble at school.
The computer in my room was the perfect distraction from all my social and romantic ineptness – it was something I could understand even as I failed to understand myself and my relationship with others. As it turns out this distraction would pay a key part in my future welfare – but we’ve jumped to far ahead already…
My First Pair of Pantyhose
Crossdressing - My First Pair of Pantyhose
When I was 12 or 13 I found myself obsessed with the idea of purchasing and wearing my own pair of pantyhose. I have no idea why that would be a good idea, and tried for many weeks to push the thought from my mind. Yet after fighting the anticipation for so long I finally broke down, and found both the courage and opportunity to purchase my first pair of pantyhose.
My mom, brother and I were out shopping and I found occasion to “browse the shops by myself”. I told my mom I’d meet her back at the car in a while, and off I went. I made a beeline to a store I knew sold pantyhose, but that was on the other end of the shopping center from where my mom and brother were shopping. I could feel my heart drumming a tune of nervous ecstasy in my chest as I circled the aisle where the object of my obsession was kept.
After what seemed like hours of mustering my courage I approached the forbidden temple – and panicked! What size was I? Where was the color I was looking for? My pending sweat gave me little opportunity to think straight and I grabbed for the first pair I thought might have a chance of fitting, hastily made my way to the cashier and then out the store.
I had a few more minutes left, and I could wait no longer – off I rushed to the public bathroom to put on my new stockings, only to discover that they were gray! Damnit. I imagined my legs encased by sexy black stockings, not gray. Not gray! It was too late though, the deed was done and I was half naked in a bathroom stall trying to figure out how to put on pantyhose when someone banged on the door.
My heart dropped to the floor, “How could this be happening?!”. I was about to hastily scramble and get dressed – sans stockings – when the person identified themselves as the cleaner. I mumbled something and pulled those stockings on as fast as I was able to. Anxious beads of sweat were dripping down my face as I realized I was late meeting my mom, and rushed out to the car.
I could feel the pantyhose brushing against my pant legs, and in the car ride home I kept pushing down my socks to feel the texture of these divine encasings, riding the thrill of a desire achieved for the rest of the afternoon.
I’ve never felt such a heightened level of excitement at purchasing woman’s clothes before. Perhaps the energy was sexual, but this was before I had any experience or knowledge of what a sexual experience would entail. I was a naively innocent pre-pubescent boy who had re-discovered the wonderful world of femininity.
I won’t bore you with all the details as to how this pair of pantyhose caused me so much joy and tension. Wearing them, sleeping in them, stressing because I had to wash them without being discovered, finding a place to hide them so noone would discover them – as it turns out my calculator case was a fabulous hiding place 
This was also the period where I began to derive sexual pleasure from woman’s clothes in one way or another. I won’t dwell on this, since just mentioning it has me blushing behind the luminescent screen of my laptop and anyway, this aspect is no longer an important part of my journey. I must admit eagerly looking forward to the time when the correct hormones are flowing through my body and such desires are under the controlling care of my mental and emotional faculties.
What do you recall about your first shopping experience for feminine finery?
I would like to clarify what I had written above concerning sexual excitement. I have never been sure in my own mind, weather wearing feminine items of clothing and becoming sexually excited, in any way took from my feelings of being feminine? I have read comments from others, that if you became sexually excited by wearing panties, etc..you were just experiencing a pantie fetish….you somehow were not on the path of feminiity. In addressing this, I feel every young boy, either before puberty, or after, who begins to feel himself directed towards femininty, will begin to experiement with different items of feminine clothing, and will become sexually aware, excited by the feel, by the knowledge of feeling comfortable as a female. This in no way, takes away from his true needs of becoming a female. I certainly agree with Vanessa in her wonderful acticle concerning this topic, where she stated, "In time these feelings will begin to be controlled." or to that effect. I would welcome comments from others concerning this.
Teens! I was babysitting and had tried on this fabulous pair of panties. Silk with rose appliques on them. Wouldn't you know it the mother came home early. I ended up leaving with her panties on and had to change out of them on my way home so my mother wouldn't find out. I also got caught driving my parents car while they were both out of town. No drivers license dressed in one of my mother's shifts and appropriate undergarments. Fortunately the shore patrol let me off the hook. My parents would have killed me if they found out. My father was an officer in the Navy. I spent the rest of the night in the house in one of my mother's night gowns.
That obsession to wear pantyhose and the "electric" sensation the texture produced is etched in my memories. I was confused, bewildered, and guilt-ridden. But i needed those pantyhose, I wore them under my pants all day and "love the feel" as they rubbed against my thighs. It was cyclical in nature, with long-ebbs in my compulsion but over the years the down times faded,
Although I’d been aware of my fascination for dressing in feminine clothing for nearly as long as I can remember (being tempted by my sister’s dresses is an early memory from age 5 or so), my first cross-dressing experiences were in my early teens. Fortunately, I was frequently alone at home, and able to borrow my mother’s and younger sister’s clothing without them knowing (or maybe they did know, and just didn’t say anything). I remember the first time was my sister’s ballet leotard with her denim skirt. Later, I tried more elaborate outfits, with panties and a training bra, sheer pantyhose, a slip, my mother’s gold sandals with two-inch heels (my feet were already too big for any of her closed-heel/toes shoes), one of my sister’s formal dresses (or a skirt/blouse combo), clip-on earrings and other jewelry, and lipstick (I hadn’t figured out any other makeup yet, but I still get a wonderful rush when I apply lipstick as the finishing touch after putting on primer / foundation / powder / blush / mascara / eye-liner & -shadow). I was never caught (borrowing clothes without permission is the only thing about my cross-dressing experiences I’m *ashamed* of), but there were a couple times I could hear someone walking into the house as I was frantically replacing items in the lingerie drawer.
A few years later, after my first girlfriend confessed having a bisexual inclination, I admitted to my urges, and we wound up shopping for lingerie together (sometimes for her, sometimes for me) to wear underneath when I put on her clothes. I think my first solo shopping experience was a pair of modest black patent leather pumps (which I still have, along with most of the late-80s lingerie I bought with my long-since-ex) at Target, late on a weeknight, so I could try them on for size without too many people around (before I figured out that 95% of size 9.5 shoes will fit me OK).
I’ve gone through on/off periods of cross-dressing since then (which seems to be very “on” right now, at the moment I’m wearing a black and white floral Ann Taylor sundress – it’s hot in the Bay Area today), but I love browsing through racks of dresses, skirts, and other pretty garments (and shoes, and jewelry, and makeup, and fragrance, and purses, and …). Even during “off” times, girlfriends have been impressed that I never complained about them taking too long while shopping.
The times I had crossdressed growing up was either with what I could find laying around or what I could borrow. I grew up with three older brothers (I was the youngest of the 4 of us) and I wasn't really into my Mothers style, although when I was really young, I was caught many times putting on her panty hose. lol Sometimes I would have a chance when my brothers had their girlfriends over for a visit, or when they moved a girl in and they left something laying around that I would try on when no one was around. I also had girlfriends of my own later on and would sometimes put their things on when they were not around if they left it here laying around. Never went into their drawers looking for anything, but if they left something laying around, it was fair game. lol
When I was a little older, I had some female friends that would let me borrow something if I liked it, but it was usually something that went with the 80's rocker look, never a skirt or dress unless I had an excuse like for halloween or something. But I did have a couple of friends that knew
The first time I actually went out to purchase any female items of my own I was about 22 years old. I had met my ex-wife. We had our first apartment together and it was before we were married and before I came out to her. She had asked me one day if she could wear my underwear because all of hers were in the laundry and she had to get to school. I told her "No problem". So she got a pair and went on her way. This happened about 3 more times and I told her jokingly that if this kept up that I was going to have to start wearing her underwear when I went to work. She told me to feel free, pick out anything I wanted and wear it, so I did.
I picked out her pair of pink and black playboy underwear and put them on and wore them to work that day. That was a huge turning point for me. I not only was wearing a pair of panties, but to work, which I had never done, and wearing them all day long and feeling very in touch with my feminine side. To top it all off, I was not having to hide it from my then girlfriend/fiance. Not only did she know, but she told me to feel free to do it. That was more freedom than I had ever experienced up to that point. That was a great day and everyone at work was asking me why I was so happy that day.
Later that night, when I got home from work I started dinner waiting for her to get home. She asked me how my day went and then she asked if I had enjoyed wearing her panties to work. I told her how much I really enjoyed it and that not only were they comfortable, but they fit great. Not just the size, but that I really feel like that was what I should be wearing all the time.
She told me that I could wear her things anytime I wanted to. I joked about "What if I want to wear your skirts or dresses?" and she said "If that's what you really want to wear, I guess it wouldn't bother me, go right ahead!" I was floored to discover that the girl I was engaged to was so open and okay with all of this. I had always imagined that if I ever had the courage to come out to a girlfriend or wife, that I would be having a hard time telling them that I liked to dress in womens clothes and expecting them to totally freak out and thinking the worst of me. But she actually offered this opportunity to me. Over the next few days we had talked a little more about it and I told her I had always liked to wear womens clothing, but it was a rare chance for me to be able to when I was growing up because the items were just rarely ever there. She told me once again that I am welcome to wear anything she has, as long as it fit and I didn't stretch it out. I am 6'1" and she was barely over 5'. Some of her things I could get into, but not much.
I told her that I really appreciated her allowing me to crossdress and even use her clothes, but that I wanted to start buying my own things and find my own style and identity, so just a few days after first wearing her panties to work, we went shopping together so I could buy my own panties. We wenty out and looked around and I found a nice 3 pack of satin string bikini type panties. I was originally just going to get the panties, but then I saw a skirt I liked, so I bought that too. Of course, my first time shopping and we were pretending it was for her. But I was still nervous feeling like everyone was watching and knew it was for me. I tried them on as soon as we got home. The panties fit, but had to get used to doing a little adjusting with the style, if you know what I mean. So I finally had my own panties to wear. And the skirt fit nice too. I was so happy to have someone that understood and was so supportive. It was easy to talk to her about anything.
After a few weeks of wearing my new panties around and coming home to wear my skirt and a few of her things and feeling all those feelings and the memories I had growing up, I had to talk to her and explain to her that all of this had made me realize who I really am and what I have known all my life, that I needed to go all the way and become a female. At first she wasn't wanting me to have surgery, but said that if that is what I wanted, I should do it because she wanted me to be happy and she would still love me. But it didn't take very long until she told me one day that she now wanted me to have the surgery because after getting to know me since I started crossdressing and getting to know my feminine side that she could only picture me as a woman. In her eyes, even when I was in a shirt and tie going to work, she still could not see me as a male, but only as a woman.
We got married and were together for nearly 10 years before divorcing over money troubles.
She made my first experience shopping for feminine items (even if I was nervous) a wonderful experience. We did a lot of shopping together and I also was shopping for things by myslef in no time.
When I was 16 my girlfriend helped bring out my feminine side. She dressed me up in panties,dresses,make up and wigs and it was fun and we would have sex. One day we were up in her bedroom and I was just in a cami and panties with a blonde wig and make and we were in bed getting ready to have sex when her older brother walked in on us,he was 21. He looked over and seen me and said how good I looked but he had caught her in bed with another girl 6 months ago and now threaten to tell their parents and tell them about me and so on. She begged him not to but he said on one condition that”your girly boyfriend must give me head” Now I love to eat pussy and she said no but I told her I’d do it for her, so he unbuckled his pants pulled it out and I got on my knees and performed oral sex a guy for the first time. As I said I like women a lot but I have to admit I did kind of enjoy it. He ended up spraying my face giving me a facial which made me fel so effeminine. After that I serviced him 12 more times with last time he brought a friend and my girlfriend and I serviced him. Her brother went away in the service after that and her and I went our separate ways after high school. I am now happily married to a woman who accepts my crossdressing and has helped me along expressing this side but if wasn’t for my girlfriend back in 1981 I may have never discovered it.