How I started Cross Dressing and other first times


How I started Cross Dressing and other first timesI love to cross-dress! I love everything about it!Like most of us cross dressers, I love everything about ladies undergarments. I like seeing lingerie in ads, in stores, on models, on TV, on women, on men and of course on me! I love the feel when I am dressed up. I love the taboo of wearing them. I love the thrill of being “underdressed”, which is wearing lots of lingerie under your manly clothes, when I go to work. I especially love the incredible horniness and lack of all boundaries when I am dressed. But alas, I can only dress on occasion, not nearly as much as I would like to.I want to write this to record how I think I got started cross-dressing. It is my intent to also chronicle some of my real life adventures while dressed and maybe even take a shot at some fiction.As I sit here now starting to recall and write, I am wearing my favorite outfit. A white babydoll top with garters attached to white stockings. Lots of frills and bows, with baby blue lace trim. A matching, frilly white thong and under that a small white G-string for support and modesty (lol!), the thong is a see through nylon and a little too big for me. The babydoll and thong were a set and I don’t have to tell fellow cross dressers that it is impossible to get a top that fits with the correct sized bottom. This set reminds me of what a newlywed would wear on her wedding day, just a cheaper version. I am on my enclosed front porch, on very public display, should any of my neighbours care to look in while they pass by. I live in a very busy and large city, close to a subway, so there is a lot of foot traffic! Exhibitionism is great! I want to be seen, I want to be humiliated and I want to be caught and made to work my way out of trouble by being forced into sex!The first thing I can remember with regards to cross-dressing happened when I was very young. In fact it may be my first memory altogether. I was really young, three or four maybe. And, as to be expected, I wet my pants at some point when we were out. I think I ended up going home in a pair of one of my Aunts grey silky panties. This may or may not have happened, but it does stand out in my mind. Of course being that young, all I have is a slight image as memory but the feeling of humiliation and embarrassment remains real in mind.The next memory would be when we were at the family cottage with our extended family, Aunts, Uncles, and Grandparents etc. As was the norm on these occasions, the k**s had to put on a “show”. A little song and dance thing, the older cousins telling the younger ones what to do. I had to be about six. This time, we had our Halloween costumes box there so someone had the idea that we should get dressed up. They found in the trunk an interesting item. It was a dress or old fashion slip maybe. It was small. It used to belong to one of my Aunts, a very petite woman who looked like that actress in the Exorcist later in life. So the point is, I was the only one it fit on, so on it went! It has blue applique over silvery grey. The material was stretchy but tight! I love that feel! It came down over my knees and has built in cups and thicker maybe 1/2inch straps. I loved it, but did not know why. When they put it on me, I clearly remember feeling great and wanting to show off. We did a dry run of the bahis siteleri canlı “show” and someone decided to put make up on me. I was young so I did not object. I think I have a memory of looking in a mirror and not being upset with what I saw. So we went out to do the actual show, everything went fine, the adults were pleased with our efforts. Then things got weird. I guess I did not want to get out of the dress because I clearly remember my Dad getting mad and saying “get him out of that”, and then storming off. When my Dad said to do something, it got done . And that is the end of that memory. But every time I pass buy a vintage clothing store I try to do in and find something similar, no luck so far! The next memory is what I have always said was the true cause of my cross-dressing. It was right around puberty, so I must have been about twelve or thirteen I guess. Now I am sure there were many, less inpactful, incidences that occurred to me between the dress up play at six and thirteen, maybe glimpse of panties and bras here and there, or some summer swim suit things, but nothing stands out. What does stand out, is the red cotton underpants! Or were they panties? I shall explain. My Mom did the laundry. I have an older sister. One day, as I was getting ready for school, I reached into the draw for some underwear and pulled out a pair of plain red cotton…underthings. I know now they were bikini cut, with seams on the hips, no fly, no tags, but not something that you would look at and say immediately, those are girls. They were just plain. Kind of cheap looking, like a dollar store pair, which would not be unusual in my house as Mom was a great penny pincher. Being prepubescent, I had no trouble fitting into them. In fact, as I still don’t know if they were males or females, I’ll bet any boy of that age would have fit.So I put them on and WOW did I like them! They were tight! Super snug on the front and grabbed my ass nicely. I loved them! I made sure from that point on, after the laundry was done, they made their way into my pile, to be put into my drawer where I wore them immediately. No one made a fuss, no one moved them to my sister’s room, so I fell in love with the feeling of pressure on my cock and balls. It was right around here when I had my first orgasm as well.My friend across the street and I had been experimenting, as boys do. We touched and sucked each other’s’ penises, put our fingers in each other’s butts, harmless stuff, but no cumming. In fact, I remember one time when we were “crossing steams” in the toilet my friend called the bubbles that came up in the water cum! I laugh about that a lot now. I knew all about jerking off, but my penis was either too sensitive or I did not use enough lube to make myself cum that way. It was not until I had my red panties on and I was grinding my cock and balls into my bedroom’s shag carpet while looking at a stolen Playboy that I blew my first load! And man was that a mind blowing thrill as I am sure we all know. No hands, just the pressure of grinding. I was in love with that feeling and, like everyone, did it as much as possible. Somewhere around there the red panties disappeared. I am guessing they didn’t make it through the wash one day. I guess I wore them out! But that started my quest for that same feeling.At canlı bahis first I found I could replicate the feeling of my red cotton panties with a speedo swimsuit I had! I was a competitive diver so I had to have them and these green and white ones were a size or two too small. After I had stretched them out too much, and in a quest for the tightness around my cock and ass, I would wedge them up my crack and pull on them. I even created a way to hang myself from two door knobs by the sides of the swimsuit for the ultimate pleasure, and had many orgasms that way. I would slip one side of the suit over one handle, pull the other door open and slip the other side over that handle, slide the suit into my crack and then lift my legs. Ecstasy! They were great, but I realized I could not wear them to school all day. I stopped diving so no more speedos for me, the green and white ones wore out as well and all I was left with was standard boy’s undies. Boring. One more incident happened around this time. We were swimming at of my cousin’s places. This family had 3 girls, all older than me. The middle girl was the hottest, I think she was about 17 at the time. Dark hair, cute face and a very hot toned body. She knew I had a crush on her. We were at the side of the pool, I was standing up and she, for some reason decided to jump up and sit on the side of the pool. As we were chatting, she was most likely making fun of her little cousin, she adjusted her body position. And I swear, she pretty much spread her legs for me! She lifted one leg up, put her foot on the side of the pool with the other leg still in the water while sitting. Then the arm moves from in front of her to the top of her knee, she stretches open and BOOM, full crotch shot for her little, impressionable cousin. Now she had her swim suit on, a dark blue one piece, but I clearly remember seeing little hairs poking out of the material! I was stunned into an embarrassed silence, and I think I was getting hard as well. At first I could not figure out what it was! And I clearly remembering just starring and starring. It was not until much later that I understood what pubic hair was, and I guess it makes sense that a girl in the late ’70s or early ’80s would have a lot of pussy hair! I still fantasize about that day. What would have happened if I was more mature. WHY did she expose herself like that? Was she just really comfortable and not concerned about a little k**, or was it the opposite? Did she know exactly what she was doing, trying to give her little cousin a hard on? Ultimately I don’t care! it was hot.At this point, puberty was fully on. I was grinding out loads almost every day. I had stolen Playboys and a couple of Penthouses that I wore the pages out of. I was always drawn to the pics of the ladies who had some lingerie on. It was here I first learned about the different types on lingerie. Thongs and G-strings were just starting to make appearances, but body suits, slips, stockings, gloves, and see through nylon bras and panties and string bikinis are the items that I recall. My prize magazine was an early 1980’s Playboy Lingerie Special. I loved everything in there, BUT I still hadn’t made the connection yet to actually putting on the lingerie myself. I recall around this time and older male cousin saying, “I love the pics bahis siteleri in those mags, but I really like a lady with a bit of clothing on” referring to lingerie. I guess it runs in the blood!As I had gotten older, I had more responsibilities around the house, this meant I had to start taking my turn doing the laundry and then BANG there it was, the confluence of all my preparing! My sister’s panties! Nirvana!She is one and half years older than me, but she skipped a grade so she was 3 years ahead in school and I guess girls of her year have to have a lot of panties. And they were magnificent. I had to handle them, folding them etc. I would estimate, in later years, she had over 50 pairs in her draw (and I wore all of them). Apparently her favorites, which became mine, where the silk floral print string bikinis. She had at least 6 pairs of these. You can find these under “vintage” style panties on line at EBay now. It may have been the first time I did the wash or I may have waited for a while, but at some point the black and red ones were the first ones I slid on. Down in the basement, they were fresh off the line and I was alone in the house. I remember quickly taking off my pants and boys underwear and hurriedly pulling those soft yet tight panties up my skinny legs. It took no time at all to adjust my balls and dick into the front, I could not believe they fit given these were ladies panties! (Now of course I realize the style back then was a high waist cut, which created a good sized front panel on the pantie. Thank goodness!) I gave my ass a quick feel and the front a quick rub. I remember just as quickly pulling them off getting redressed and sitting there wondering what had happened. Yes I was confused, but I was also hard as a rock. I left them there, went to my room and jerked off (I had figured it out by now) twice! I thought about what I had done for days, always making me hard, but confused. Then I remembered a story I had read in a Playboy letter, about a man wearing ladies undergarments. Once I had put that all together in my mind, that men can in fact wear ladies panties, it has been done before so it must be ok at some level, I allowed myself to explore. And then the fun really began!So here is a list of some of my adventures. Let me know if you would like to hear the extended story that goes along with any of them.Trying on the Neighbors’ mom’s bra in front of him.Through High School – just moms and s*s, trying not to get caught (fiction story, got caught in basement!)Polaroid with mom’ lingerie set on – burned itexhibition to other cousin at cottage – taken to the head Doctor after thatNothing in first few years of Uni – unit I moved into apartment – then the fetish really took offMany stolen from laundry roombroke into an apartment for some – feel bad about thatwearing roommates girlfriends stuff but still nothing of my ownfirst trip to sex shop lingerie storediscovering massage parlors – went in in lingerie for the 1st timeAs I mature I get more adventurous, and less cautious.Brought a guy home and met a guy in a hotel for mutual masturbation in pantiesStarted to experiment with ass play after a massage attendant slipped a finger in! Used everything I could find after that.Buying my own collection.Purging the collection only to replace it againFirst trip to a tranny – I chickened outStarting to show off more – night time walks – massage parlors etcSecond trip to a tranny years later – loved it.Hooked up with a CD – loved itDiscovered Omegle and other sites – on there all the timeDiscovered xhamster – awesome!

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