ADDOLESANCE…..The years of confusion and discovery

Early Teens

Very early in my teen years (12-13), I started to expand my dressing experiences. With a sister a couple of years younger, it was fun to “play dress-up” with her. I could just fit into some of her stuff and my mom’s cloths where starting to fit better. This was also the time I discovered make-up and started to learn how to apply it…..let’s see, mid 70’s (ugh, that long ago?), lots of green or blue eye shadow, (shudder) and bright red lipstick…there I look hot, well that’s what I was

There was one time when my parents were out for the evening; my sister and I were playing dress up, makeup and all, when they dropped in at home between parties. I scrambled to get changed, came downstairs……”what’s that on your face?” my mom asked…I had forgotten about the makeup….”umm, we were playing dress up…(?)” “Well go clean it off”, nothing else was ever mentioned.

In my attempts to look more feminine, I started wearing my mom’s bathing suit that had quite ridged cups, which I quickly found would keep their shape if I put some socks in them while wearing her clothes. This quickly changed to a bikini with the same properties, but then I thought, “why don’t I go straight to a bra and panties?”  There was no looking back from there.

What’s that strange sensation? Onset of confusion.

One of my favorite pieces of clothing was a body suit, the type with snaps at the crotch. I would pretend to be a gymnast, but while attempting to do handstands by sliding off the bed, I became aware of a strange sensation from my groin area. I think we all understand what goes on with a young boy’s body at this stage of life. Initially it just felt too got to question, but as the months went by and turned into a couple of years, I started to wonder what the heck was going on, what was “wrong” with me? This was not something anybody else did, I was pretty sure. But despite these thoughts, I continued to dress.

At about the age of 15, there was a curious occurrence at school. One of the other boys in my class happen to mention he had read an article were a man had had an operation to become a woman! This was the first I had heard of such a thing, but my interest was piqued, but a worrying thought crossed my mind, was this what was in store for me? (As an aside, this guy was a bit different, and went on about this story for a long time. If I have ever unknowingly met anybody who might have TS tendencies, my guess would be that he could have been one).  But I stilled enjoyed being a guy and those sensations when dressing, so what gives? It wasn’t until years later that I would have access to reading material on the subject. So in the meantime, I continued on dressing, but now with a twinge of guilt and uncertainty, along with the pleasure.

The High School years. More discoveries and the purge.

I never had a real girlfriend during high school, had a crush on one, but was too shy ever to ask her out….had friends who were girls, ”so I must be normal, somehow, as I still have an interest in girls”……”oh I like what she is wearing, wonder what it would look like on me?”…….lol. “I’m confused, but I bet it would look good”.

I had the chance to be home alone more now with both parents working and my sister doing her own thing after school. We lived in the country with a really good view of the 2 miles of gravel road that lead from the main highway to our small farm, plenty of time to recognize one of the vehicles and get changed. It’s amazing how fast you can get changed, remove makeup and straighten things away with practice.

This was also the time I discovered an alternate use for Duct Tape. Ouch, but great results with practice. It wasn’t, again, until years later I read about how others have used this taping technique.

There was one weekend I was able to dress from midday Saturday until late Sunday. I went all out. With the butterflies in my stomach, I rid my legs of hair with a depilatory for the first time and found how sexy bare legs can feel. Full make-up, of course, try and styled my long hair more feminine,  then pretty much go through everything of my sisters and mothers stuff until late in the evening. When you have the chance, you have to see how everything looks on you, can’t stay in the same thing for more than 10mins..haha. I slept in my sisters room, in her nighty, got up the next morning and dressed 100% in her barn clothes and went and did chores…all the time, heart pounding, wondering if a neighbour might drop by unexpected, not that they had ever done that in the past. Is this anxiety something that heightens the experience?

With afterschool and weekend employment, I had my own extra money so I started to order my own clothes from the Sears catalogue, mostly nylons and underware. I would pick it up at lunchtime from the local catalogue store, stuff it in my back pack and hope I didn’t need anything out of it during the bus trip home, heart still pounding again, knowing I was carrying this secret on my back.

This was also the time that the PURGE raised its ugly head. A staple of the cross dressing experience, it is usually accompanied by a great feeling of guilt and a hope that this will be the end of the crossdressing “torment”. And of course, for those who have gone through this, we know that’s not the case. Most of us have experience the purge more than once, a costly lesson that could have been avoided if only we had known what the future held, or at least for myself, if I had more understanding of what I was and that I was not alone .

Some of the very first photos I took of myself.

Thanks for reading. I hope it is entertaining and maybe even stimulate your own memories of your early experiences.




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