How it Began - My crossdessing.
I 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” (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 merrywidow 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 made from see through nylon and a little too big for me. The merrywidow and thong were a set of course and I don’t have to tell my 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 either a dress or an 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 “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 impactful, incidences that occurred to me between the dress up play at six and thirteen, maybe glimpse of panties and bras here and there, in real life or in a magazine or on T.V, 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 hurt to rub to long. 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, my cock was actually pointed down between my legs at the time, just the pressure of grinding. I was in love with that feeling and, like everyone, from there on out, I 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 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. In a quest for even more tightness around my cock and pressure on my butthole, I would wedge the swimsuit up my crack and pull on them. I even created a way to hang myself from two doorknobs by the sides of the swimsuit for the ultimate pleasure. I would slip one side of the suit over one handle, pull the adjacent door open and slip the other side over that door handle, then slide the suit into my crack and lift my legs. Ecstasy! I would then rub the front of the Speedo. I had many orgasms that way (thankfully I was a light weight and did not break the door hinges, that would have been tough to explain, lol). The Speedo was great, but I realized I could not wear them to school all day and I really wanted to experience the full day of wonderful stimulation of tight underwear like when I wore the red panties to school. Anyway, shortly thereafter, I stopped diving, so no more speedos for me. The green and white ones wore out, I think I torn the side one day, and all I was left with was standard boy’s undies. Boring.
One more incident happened around this time. We were swimming at the pool 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 in the water 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, legs dangling in the water. 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 continuing to sit. 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 swimsuit 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. I think this incident also help extend my lingerie fetish to swimsuits! I love waring womens swimsuits! I currently own one one piece in red and one string bikini bottoms with side ties.
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 of lingerie. Thongs and G-strings were just starting to make appearances, but body suits, slips, stockings, garter belts, camis, merrywidows, long silk gloves (yes, I consider them lingerie), see-through nylon bras and panties and string bikinis are the items that I recall. My prize magazine at that time 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 lingerie on myself. Actually wearing it. I recall around this time an older male cousin saying, “I love the pics in those mags, but I really like a lady with a bit of clothing on” referring to lingerie. I guess it runs in the family!
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 in her year have to have a lot of panties. And they were magnificent. I had to handle them, taking them of the line, folding them, putting them in the laundry basket. I would estimate, in later years, she had over 50 pairs in her draw (and I wore all of them). Apparently, her favorites, which soon 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 online 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 because they were the “most manly” I foolishly convinced myself back then. 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 boy’s underwear and hurriedly pulling those soft yet tight silky 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. It was never about my sister, I was never sexually attracted to her (nor my mother) it was strictly thinking about the look and feel of the panties that made me hard. At some point during my consternations, I remembered a story I had read in a Playboy letter, about a man wearing ladies’ undergarments. Maybe it was stuck in my sub-conscious when I first pulled on the panties and that was why I did it. Wish I could remember that story but in the end it does not really matter, it does not take much to influence a super horny teen. Once I had put all of this together in my mind, that men in fact can and have worn ladies lingerie for sexual purposes, it has been done before, and it is something I think I like, it was like giving permission to myself to do likewise. I did not have to worry about the “am I gay because I like to do this” question because the guy in the letter had sex with a woman while dressed so it must be ok for straight people to do this. Right? (I would not call myself straight now, I love all and have all kinds of different sex! All great! I do not care for labels now-a-days but as a k** it was a very complicated and stressing issue as I am sure all would agree.) From then on I allowed myself to explore.
And then the fun really began!
I began to raid my sister’s room regularly. Racing home from school to try something on before she got home. Then, when I would hear her come in, run across the hall and return her panties to her dresser before she came upstairs. I was almost caught at least once a week but the drive was soooo strong I could not stop!
Not long after I began experimenting with her panties, SHE started to expand her lingerie selections. And my fetish expanded right along with hers. One day I found a garter belt and stockings in another one for her drawers! It took a few minutes, but not too long, before I figured out how to ware them. Then there were all the half slips that felt so good I started trying on her somewhat limited selection of bra. Can not remember her size but she must have been a “d” cup. I would stuff the bra with her panties at times. And not too long after that I was into her dresses, skirts, blouses, cut off jean shorts, bathing suits. What ever I could fit in, I tried on! She must have know what I was doing. The staining of her panties, the stretched out pantihose the fact you can never quite return everything to the exact same place. But God love her, she never said a word. She had to know but never let on. Wish I could tell you some fun sexy stories along those lines, but it would be fiction.
Of course my sister was not the only woman in the house! At some point I crossed the line and started to wear my Mother’s lingerie as well. She did not have the quantity of my sister’s collection buy she had variety and quality. All sorts of different styles of panties bras and slips. And all very sexy. No granny panties for my family! Bikini, lace briefs, french cut, usually all with matching bras, something my sister did not do. And it was my Mom’s silk body suit or teddy with crotch snaps. that really cemented the fetish for me. One garment that did it all. Tightness on the cock and balls, smooth silk caressing the ass and torso, the pull of the straps on the shoulders. How you could move about and lift your shoulders only to feel the pull on your balls! My god it feels soooo good. I love wearing body suits now when I can.
One time I even found a pair of crotchless panties in her drawer! Not my cup of tea but you know, you always think of your parents as sexless but perhaps my father had a hidden lingerie fetish as well???
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. Was hoping he would get into it and try on some things himself, but no dice. His mother did not have the same sexy things I found in my house. Just plain beige or white bras. Never saw her panites but I assume they were likewise boring.
Through High School - just moms and sis, trying not to get caught (fiction story, got caught in basement!). One time I did have a pair of sister’s panties on when she can down the basement stairs. I quickly hid under a blanket and pretend to watch TV and she left. It was a bit of a rush.
Polaroid with mom' lingerie set on - burned it out of shame. The set looked a little like this but neither me nor my mom looked this good in them!
Exhibition to other cousin at cottage. I love exhibitionism. She was a little younger and I was looking after her down by the dock on our large property. We could not been seen by the adults. We played strip “fish” the card game. Well I played it and is short order was naked in front of her. When she did not flinch seeing me naked, I would then roll backwards on to back giving her a close up look at my asshole. This definitely cemented my exhibitionist tendencies. Not sure she liked it. But you see how early my recklessness started.
Friend’s sister galivanting about in panties at the top of the stairs. Still remember them. Shiny silver stain but an unflattering regular brief. Yet I still get hard thinking about her.
Nothing in first few years of Uni - unit I moved into apartment - then the fetish really took off
Many stolen from laundry room.
broke into an apartment for some - feel bad about that, but again, bad decisions and recklessness are a hallmark of “transvestic disorder”. Well the DSM5 calls it a disorder, I call it FUN!
wearing roommates girlfriends stuff but still nothing of my own
first trip to sex shop lingerie store
discovering massage parlors - went in in lingerie for the 1st time
As I mature I get more adventurous, and less cautious.
Brought a guy home and met a guy in a hotel for mutual masturbation in panties, wish we did more, but life is all about taking the little steps.
Started to experiment with ass play after a massage attendant slipped a finger in! Used everything I could find after that. Still do. Yet, anal virgin. I really want to lose it to a hot crossdress/tranny. Someone super fem.
Buying my own collection.
Purging the collection only to replace it again
First trip to a tranny - I chickened out
Starting to show off more - night time walks - massage parlors – nude beaches – nature walks – in public in a mini skirt that might pass a shorts etc.
Second trip to a tranny years later - loved it.
Hooked up with a CD - loved it
Discovered Omegle and other sites - on there all the time
Discovered xhamster - awesome!
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” (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 merrywidow 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 made from see through nylon and a little too big for me. The merrywidow and thong were a set of course and I don’t have to tell my 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 either a dress or an 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 “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 impactful, incidences that occurred to me between the dress up play at six and thirteen, maybe glimpse of panties and bras here and there, in real life or in a magazine or on T.V, 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 hurt to rub to long. 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, my cock was actually pointed down between my legs at the time, just the pressure of grinding. I was in love with that feeling and, like everyone, from there on out, I 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 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. In a quest for even more tightness around my cock and pressure on my butthole, I would wedge the swimsuit up my crack and pull on them. I even created a way to hang myself from two doorknobs by the sides of the swimsuit for the ultimate pleasure. I would slip one side of the suit over one handle, pull the adjacent door open and slip the other side over that door handle, then slide the suit into my crack and lift my legs. Ecstasy! I would then rub the front of the Speedo. I had many orgasms that way (thankfully I was a light weight and did not break the door hinges, that would have been tough to explain, lol). The Speedo was great, but I realized I could not wear them to school all day and I really wanted to experience the full day of wonderful stimulation of tight underwear like when I wore the red panties to school. Anyway, shortly thereafter, I stopped diving, so no more speedos for me. The green and white ones wore out, I think I torn the side one day, and all I was left with was standard boy’s undies. Boring.
One more incident happened around this time. We were swimming at the pool 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 in the water 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, legs dangling in the water. 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 continuing to sit. 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 swimsuit 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. I think this incident also help extend my lingerie fetish to swimsuits! I love waring womens swimsuits! I currently own one one piece in red and one string bikini bottoms with side ties.
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 of lingerie. Thongs and G-strings were just starting to make appearances, but body suits, slips, stockings, garter belts, camis, merrywidows, long silk gloves (yes, I consider them lingerie), see-through nylon bras and panties and string bikinis are the items that I recall. My prize magazine at that time 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 lingerie on myself. Actually wearing it. I recall around this time an older male cousin saying, “I love the pics in those mags, but I really like a lady with a bit of clothing on” referring to lingerie. I guess it runs in the family!
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 in her year have to have a lot of panties. And they were magnificent. I had to handle them, taking them of the line, folding them, putting them in the laundry basket. I would estimate, in later years, she had over 50 pairs in her draw (and I wore all of them). Apparently, her favorites, which soon 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 online 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 because they were the “most manly” I foolishly convinced myself back then. 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 boy’s underwear and hurriedly pulling those soft yet tight silky 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. It was never about my sister, I was never sexually attracted to her (nor my mother) it was strictly thinking about the look and feel of the panties that made me hard. At some point during my consternations, I remembered a story I had read in a Playboy letter, about a man wearing ladies’ undergarments. Maybe it was stuck in my sub-conscious when I first pulled on the panties and that was why I did it. Wish I could remember that story but in the end it does not really matter, it does not take much to influence a super horny teen. Once I had put all of this together in my mind, that men in fact can and have worn ladies lingerie for sexual purposes, it has been done before, and it is something I think I like, it was like giving permission to myself to do likewise. I did not have to worry about the “am I gay because I like to do this” question because the guy in the letter had sex with a woman while dressed so it must be ok for straight people to do this. Right? (I would not call myself straight now, I love all and have all kinds of different sex! All great! I do not care for labels now-a-days but as a k** it was a very complicated and stressing issue as I am sure all would agree.) From then on I allowed myself to explore.
And then the fun really began!
I began to raid my sister’s room regularly. Racing home from school to try something on before she got home. Then, when I would hear her come in, run across the hall and return her panties to her dresser before she came upstairs. I was almost caught at least once a week but the drive was soooo strong I could not stop!
Not long after I began experimenting with her panties, SHE started to expand her lingerie selections. And my fetish expanded right along with hers. One day I found a garter belt and stockings in another one for her drawers! It took a few minutes, but not too long, before I figured out how to ware them. Then there were all the half slips that felt so good I started trying on her somewhat limited selection of bra. Can not remember her size but she must have been a “d” cup. I would stuff the bra with her panties at times. And not too long after that I was into her dresses, skirts, blouses, cut off jean shorts, bathing suits. What ever I could fit in, I tried on! She must have know what I was doing. The staining of her panties, the stretched out pantihose the fact you can never quite return everything to the exact same place. But God love her, she never said a word. She had to know but never let on. Wish I could tell you some fun sexy stories along those lines, but it would be fiction.
Of course my sister was not the only woman in the house! At some point I crossed the line and started to wear my Mother’s lingerie as well. She did not have the quantity of my sister’s collection buy she had variety and quality. All sorts of different styles of panties bras and slips. And all very sexy. No granny panties for my family! Bikini, lace briefs, french cut, usually all with matching bras, something my sister did not do. And it was my Mom’s silk body suit or teddy with crotch snaps. that really cemented the fetish for me. One garment that did it all. Tightness on the cock and balls, smooth silk caressing the ass and torso, the pull of the straps on the shoulders. How you could move about and lift your shoulders only to feel the pull on your balls! My god it feels soooo good. I love wearing body suits now when I can.
One time I even found a pair of crotchless panties in her drawer! Not my cup of tea but you know, you always think of your parents as sexless but perhaps my father had a hidden lingerie fetish as well???
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. Was hoping he would get into it and try on some things himself, but no dice. His mother did not have the same sexy things I found in my house. Just plain beige or white bras. Never saw her panites but I assume they were likewise boring.
Through High School - just moms and sis, trying not to get caught (fiction story, got caught in basement!). One time I did have a pair of sister’s panties on when she can down the basement stairs. I quickly hid under a blanket and pretend to watch TV and she left. It was a bit of a rush.
Polaroid with mom' lingerie set on - burned it out of shame. The set looked a little like this but neither me nor my mom looked this good in them!
Exhibition to other cousin at cottage. I love exhibitionism. She was a little younger and I was looking after her down by the dock on our large property. We could not been seen by the adults. We played strip “fish” the card game. Well I played it and is short order was naked in front of her. When she did not flinch seeing me naked, I would then roll backwards on to back giving her a close up look at my asshole. This definitely cemented my exhibitionist tendencies. Not sure she liked it. But you see how early my recklessness started.
Friend’s sister galivanting about in panties at the top of the stairs. Still remember them. Shiny silver stain but an unflattering regular brief. Yet I still get hard thinking about her.
Nothing in first few years of Uni - unit I moved into apartment - then the fetish really took off
Many stolen from laundry room.
broke into an apartment for some - feel bad about that, but again, bad decisions and recklessness are a hallmark of “transvestic disorder”. Well the DSM5 calls it a disorder, I call it FUN!
wearing roommates girlfriends stuff but still nothing of my own
first trip to sex shop lingerie store
discovering massage parlors - went in in lingerie for the 1st time
As I mature I get more adventurous, and less cautious.
Brought a guy home and met a guy in a hotel for mutual masturbation in panties, wish we did more, but life is all about taking the little steps.
Started to experiment with ass play after a massage attendant slipped a finger in! Used everything I could find after that. Still do. Yet, anal virgin. I really want to lose it to a hot crossdress/tranny. Someone super fem.
Buying my own collection.
Purging the collection only to replace it again
First trip to a tranny - I chickened out
Starting to show off more - night time walks - massage parlors – nude beaches – nature walks – in public in a mini skirt that might pass a shorts etc.
Second trip to a tranny years later - loved it.
Hooked up with a CD - loved it
Discovered Omegle and other sites - on there all the time
Discovered xhamster - awesome!
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