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I have the best of both worlds when I am Crossdressing! – Crossdreser Society | An Online Resource for Crossdressers | Transgender

I have the best of both worlds when I am Crossdressing!

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I am a crossdresser. I have the best of both worlds when crossdressing.

My name is Lisa, and I’m a crossdresser.

Though I am a male physically and still enjoy lots of masculine tasks, on the inside I am also a woman who yearns for all things womanly.
To me, I have the best of both worlds simply because I get to experience life as both sexes since I am able to venture out into the world as a passable male to female crossdresser. This diary will chronicle my life  crossdressing and highlight my feminine side as Lisa.

My Early Childhood as a Crossdresser

Some of my very first memories in childhood have to do with cross dressing and my desires to be a female as I will detail throughout my diary. I also write about the major points in my life when I actually tried to abandon crossdressing altogether, but every attempt has failed as you can probably relate to. It is part of me and has been from the beginning, and I have come to not only accept it but enjoy it! There is just a different feeling inside of me when I transition into a girl, so this writings celebrate all of the great things associated with being a girl as a crossdresser.

Hopefully my diary is clean and tasteful and will give most readers exactly what they’re looking for including plenty of crossdresser pics. I hope you enjoy this website as much as I enjoy being Lisa.
Some of my earliest memories in life are of cross dressing bras and panties. In my preschool days, my family moved to the residence where my parents still live, so I know that if I remember things from our first house, I must have been four years old or younger. And I have plenty of crossdressing memories from that first house, so I know my history of crossdressing goes back to the age of three or four. In fact, I don’t ever remember a time in my life where I didn’t want to cross dress.

crossdresser Lisa photoThe first item I remember crossdressing with was my mother’s bra. When she was away, I sneaked it out of her dresser drawer and ran into my bedroom and locked my room door in order to change into it. I still remember my brother wanting to get into the room and pounding on the door to let him in, but I refused until I had the bra in place, clasped, and hidden under my shirt. I still remember the shirt I wore that day, and I remember when my mother came home running and jumping into her arms to give her a big hug. She obviously noticed I was wearing her bra but said nothing.
Perhaps these early experiences with bras is the reason that I’m still so picky about them still today.I also remember sneaking my older sisters panties from her drawer and wearing them frequently. One day I was at a friend’s house, and there was a big mud puddle in his backyard. We were so filthy after playing in it that my friend’s mother insisted on putting us in the tub. She told us to undress on the steps of the back porch before we went into the house. I still remember my dilemma because I was wearing a pair of pink nylon panties. Luckily my friend undressed first and bound into the house leaving me alone to take off the panties. I hid them at the bottom of my pile of clothes and ran into the bathroom for my bath. I don’t know if my friend’s mom washed the clothes at her house or returned them as-is to my mother, but it was known to both women early on that liked to I wear girls underwear.

Besides these incidents, I remember sneaking my sister’s socks and wearing them to play in the basement. You know how a child thinks he can run faster with new shoes; well, I thought I could run faster and jump higher when wearing my sister’s bobby socks as we called them. The socks were nylon and pulled up well over my knees, and I can still remember how thrilled I was when I wore them.

Once I entered elementary school, I can remember wearing my sister’s panties to school all the time. I never remember taking them off or if I replaced them back in her drawer at the end of the day, but I remember when going to the bathroom at school making sure no one ever saw my underwear. Aside from school, occasionally my sister would dress me and my brother up in her clothes, and we’d play house. Needless to say I had the time of my life.

As I grew older, I was rational enough to realize how dangerous it was to wear girl’s underwear to school, and that’s probably about the time I began creating my first stash. My initial stash consisted of panties borrowed from my sister and one of her bras. As she outgrew her underwear, I remember that it would be moved to the back of her drawer, and so I would carefully choose panties that I knew she no longer wore. She also had a bra that had a broken clasp in the back of her drawer, so I took that and safety-pinned it together and wore it that way.

In my junior high school days, I finally discovered pantyhose. This was back in the 80’s when women still frequently wore pantyhose as part of their everyday wardrobe. My mother would wash batches of her pantyhose and hang them up to dry down in the basement washroom, so of course I helped myself to a pair here and there. My mother preferred Sheer Energy pantyhose by L’eggs in suntan color, so it’s probably no coincidence that that is my favorite brand and color as well even today.

crossdressing manMy mother was the type of person who never threw anything away, so she kept boxes of old clothing in the basement. This was a goldmine for me, and it also provided places for me to hide my crossdressing stash. Speaking of the old clothing in those boxes, my brothers liked to dress up in girls clothing as well from those boxes, and often when we’d play games late at night, the loser would have to dress up like a girl and show everyone else. I wanted to lose as bad as they did, so it was funny to see everyone pretend to want to win but really want to lose. We had friends and cousins sleep over often, and we always made dressing up like a girl the penalty for losing, and out of every boy that slept over and participated in the games, every one of them loved to dress up like a girl. I don’t suspect that any of them have taken cross dressing to the extent that I have, but from that experience, it is my belief that a majority of men would love to be a crossdresser if they had the chance. If men weren’t attracted to women’s underwear, there’d be no need to make it so sexy. But I digress.

When I entered high school, I got my first part-time job at a department store. It goes without saying that I quickly located the area in the stock room where they kept the women’s lingerie. I still remember picking out the items that I wanted and then throwing money in the cash register. I’d change into the lingerie in the bathroom and just wear it home. I’m sure I threw off the inventory numbers at the end of the year, but I did purchase the items in a round about way. This helped me build up a great stash of bras, panties, slips, and pantyhose. I could still fit into my mother’s clothing as well, so I was in cross dressing heaven during my high school days. It also didn’t hurt that my older brother with whom I shared a room went away for college, so I had a room to myself and slept nearly every night in bra and panties, pantyhose, and a full length slip as a nightie. My cross dressing during high school was largely confined to my bedroom.

After graduating from high school and going to college, I had a decision to make. I didn’t know how I was going to take my clothes and lingerie with me, so I finally decided that I had grown up enough to the point where I no longer needed to be a crossdresser. I gathered everything up into a plastic garbage bag and threw everything away the night before I left for college hoping this new change would cure me.

My new found freedom lasted for about two months until I could no longer bear it and bought a pair of pantyhose at the grocery store. Around the same time, I happened to get a part-time job for the same department store that I worked for during high school. I already knew the routine and had built up a nice collection of lingerie and pantyhose before I knew it hiding items at the bottom of cardboard boxes I used to store all of my old papers and books from school. If one of my roommates ever discovered my cross dressing, they didn’t tell me about it.

My desires for crossdressing would come and go in college and usually evolved around whether or not I was dating anyone at the time. It’s always great to fall in love and experience those initial stages of romance, but I can still remember after dating a girl for a month or two that I’d begin to yearn for my cross dressing ways. The most serious girlfriend I had during college went home one summer and moved out of her apartment in the process. I was staying in town, so she asked if she could store some boxes at my place. I of course agreed and kept several boxes for her in my closet. I never opened them to go through them, but she also had me hold onto a handful of dresses as well that I hung in my closet. If only she really knew! At the first chance, I tried on all of her dresses and still remember dressing up in them and walking around campus. I’d always venture out at night of course and kept my distance from anyone.

About two months before I graduated from college, I secured a job and knew that I had another decision to make. I’d be going far away from home to live and reasoned with myself once again that it was time to abandon my cross dressing. I determined that the big change in my life and new city would provide the opportunity to forget about the past and start anew. Of course I was wrong again as it took me about three months in my new location to purchase a package of panties along with some groceries from the supermarket. I methodically added pantyhose along the way, and when I came home for Christmas that first year, I took one of my young nephews and headed to Walmart as if we were father and son out doing some shopping for mom. I purchased bras and panties as well as sundry items to make it look like I was just running an errand.

About a year on the new job, I met the girl who would become my wife. Just like past girlfriends and acquaintances, I didn’t dare tell her about my cross dressing desires although I greatly regret it now. I’m quite sure she would have been as understanding as can be expected, and we could have even had some fun with it while we were dating, but I won’t get that chance again. Speaking of dating, she knew that I shaved my legs and often trimmed other body hair, and I told her that I did this mainly to stay cool in the summer, which was partially true. We dated for two years before we married, and while I abandoned cross dressing at first during our courtship, I just couldn’t suppress that need to dress and did it secretly. We didn’t live together before our marriage, so hiding my stash was never a problem then.

Once we did tie the knot, I was of course faced with the same decision that I had experienced over the years….what do I do with my stash? I threw it away once again hoping that married life would finally be the catalyst to help me stop cross dressing, but it had always been a part of my life and always would be.

The first urges for crossdressing came  again after our wedding came about six months in. When I could no longer resist the feelings, I remember stopping by a Walmart about 8 AM on my way in to work one morning. I walked directly to the women’s area and selected a white cotton blouse. I next headed for the lingerie section and luckily (I guess) they were holding a staff meeting with all the employees gathered a fair distance away, so I was free to browse for a bra and some panties with no one else around. I selected a seamless bra in 38B and grabbed a package that included three pairs of nylon panties. I next headed for the hosiery section and picked out a pair of suntan and a pair of nude pantyhose. I didn’t care about any sundry items; I just headed for the register with my contraband not caring what the lady at the register thought. I purchased the items and stuffed them in the spare tire compartment beneath the trunk in my car. Over time, I of course found ways to increase my stash and add shoes and a few more articles of clothing. When my stash become too large to fit in with the spare tire, I moved everything to the inside of a speaker that connected to my stereo. It was one of those massive stereos from the eighties that came with giant speakers that were essentially big wooden cases with little inside.

My crossdressing went on like this for the first few years of our marriage with me using every means possible to hide it. During this time, I racked my brain for ways to tell me wife because I knew from past experience that this would be something that I’d have to deal with my entire life.

My break–if you can call it that–came while on a business trip to Korea in late November. I underestimated how cold it would be in Seoul and was completely unprepared in terms of warm clothing. I spoke with my wife nearly every day and would comment about the cold when finally it dawned on me that this could be a chance. During one of our phone conversations, I mentioned to my wife that I purchased a pair of tights from the convenience store to keep my lower body warm. This was partially true because while I did purchase a pair of tights from a 7-11 in Seoul, I did so because I wanted them…not only to keep warm. My wife’s response was, “oh, that’s a good idea,” and that was the first seed. I had of course brought my own pantyhose, panties, lingerie, etc. on the business trip, but now I could actually take some tights home in my suitcase that she could see.

I ended up packing two pairs of tights and one pair of active support pantyhose in my suitcase and told my wife that I had worn them under my suit at work, and I of course told her how much I liked them and thought they were very practical to wear during cold weather. She agreed, and that was that. I now had a small collection of pantyhose and tights in my sock drawer that I would wear on cold days with no reaction from my wife. I’m also an avid fisherman so I began wearing pantyhose and tights under shorts inside of my fishing waders “to keep warm.” This also made sense to my wife, and this was a time when I began openly purchasing new pairs of pantyhose and tights to add to my collection.

When my wife was pregnant with our third child, my biggest break came. She had just received an order of maternity clothes that she’d purchased online at the Gap. When we were going through the box, she picked up a sweater and said, “hey, this might even fit you!” I of course took the bait and said, “let me model it for you.” I put on the sweater and pulled on a pair of maternity capris and modeled them for my wife. She got a huge kick out of it, and so did I of course. The next time I modeled the outfit for her; I borrowed one of her maternity bras and wore pantyhose beneath the capris to give my figure a better shape. It became sort of customary that I would try on her new maternity things and model them for her, and it even got to the extent where she wanted me to model her clothes in front of our good friends!

Riding the wave, I told her that I had a great idea…I should dress as a woman for Halloween. She thought that would be fun, so I began to gather the items for my costume. When I say gather, I mostly mean pulling items from my stash and bringing them home in shopping bags telling my wife that I had just purchased something new as I put my costume together. I did this with a bra and panties set, some more pantyhose, and a wig.

I actually went to a thrift store and purchased a 100% polyester white blouse mostly because I wanted my bra to show through it, and then I picked up a couple of skirts…one an A-line ankle length skirt in yellow with a flower print and the other a knee length skirt in black with small white flowers. I modeled everything for my wife (seen in the three pics below) and finally determined that I’d wear the yellow skirt due to the season. I was so excited on the big day that I wore my bra and panties to work along with the pantyhose that I’d wear that night. My wife was used to me wearing pantyhose by then, so she thought nothing of it…probably because she didn’t notice the bra beneath my turtleneck.

When I got home from work, we quickly ate dinner and then headed to the bathroom so my wife could put on my makeup. You can’t imagine my thrill sitting there on the edge of the tub fully dressed with my wife applying makeup to me. Once my makeup was set and my wig on, my wife commented that I looked quite beautiful. I agreed of course. I took our two small children and we headed out to trick or treat. It was dreadfully cold that night, and I still remember the wind howling up my skirt, so I came back into the house and borrowed a navy coat from my wife that happened to fit me. We only managed to go to a few houses because it was so cold, and my kids wanted to go home, but the reactions on the faces of the neighbors were priceless as they didn’t think anything of this woman but then looked at my kids and realized that the woman with them wasn’t their mother…it was actually me.

At the end of the night, I told my wife that sometime it’d be fun to go out shopping dressed as a woman. She suggested that I go right then and fill the car with gas and see if anyone noticed. No one did, and that provided the spark within me that I could actually pass as a woman. Up until that point, my adventures while dressed up comprised mostly of staying indoors or short walk at night through a park or a distant neighborhood without much going on.
After that Halloween, I would occasionally dress up at night after putting the kids to bed when there wasn’t anything else to attend to. My wife and I called this our fashion shows as she’d usually mix and match outfits of her own with both of us fighting for time in front of the mirror. The next spring when my wife took the kids home to visit her mother, I dressed myself up and went out to the thrift store for the first time. I was so nervous, and my makeup was terrible, and it was likely a dead giveaway, but when I called my wife the next time, I told her that I ventured out dressed as a woman and bought a few things. She laughed at the thought, and when she came back, I held another fashion show and modeled my new purchases. This was the way things were for two years or so, but as I got more and more carried away, I think my wife began to worry, so I cut back on my open cross dressing in the house. My children were also getting older and more perceptive, so that was a reason as well.

We have never sat down and really discussed my crossdressing, but I told my wife some of my memories of being dressed up by my sister and how fun it was. She also knows that I love panties and pantyhose, and while she probably doesn’t understand why I love to be a crossdresser, it has never been an issue in our marriage, but that’s largely because I pick my spots cautiously.

Now that our kids have gotten older, it’s becoming harder and harder to dress so openly when they are around. Yes, I am a crossdresser and always will be, but I have to be a responsible husband and parent first, so that means less and less adventures for me. I still wear panties and pantyhose all the time to bed during the cold months, and it’s never an issue with my wife even when we get intimate, but I haven’t dressed up with people in the house for years. Perhaps that is why I have decided to put together this diary. With my adventures happening with less frequency, this may be my way to continue to express myself as a woman.
By: Lisa.


About the Author:

Hi, I’m Marcy Simpson, the founder and creator of Crossdresser Society. I have been a crossdresser for over 25 years and I am also an author, photographer, entrepreneur, and admirer of the feminine realm. I currently work and live in Los Angeles, California.


  1. Rachel  January 29, 2013

    Loved the story.
    Took me back to the days of wearing leotards or womens one peice bathers under my clothes
    My wife an daughters often see me dressed up, and also a lot of Aucklanders


  2. Rachel  January 30, 2013

    Loved the story.
    I found as my girls reached an age of 13 or so, they were mature enough to let them know about my hobby without telling their friends.
    Now I can freely walk around the house with them home

  3. places to buy dresses  February 13, 2013

    Its like you read my mind! You seem to know so much about this, like you wrote the book in it or something. I think that you could do with some pics to drive the message home a little bit, but instead of that, this is fantastic blog. A fantastic read. I’ll definitely be back.

  4. acne  April 19, 2013

    Loving the information on this web site, you’ve carried out outstanding job around the posts.