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The Progression of Crossdressing For Me

December 18, 2014

Throughout my life, my urge to crossdress seems to have included an urge to expand.  I went from living in fear that anyone might find out to going out in public and introducing myself to people.  I went from trying to be certain that any feminine clothes were either covered up or were androgynous to wearing skirts and heels in public.  There has been a progression.  Here is an attempt to express this progression:

The Thought – At first, I remember thinking about silky fabrics as a child.  Probably, I was 6 or younger.  Pantyhose and slips were the primary things that I thought of.

First Try – Somewhere around the age of 6 or 7, I found some discarded nylon hosiery and tried them on.  I kept them and would occasionally wear them.  As I recall, I also borrowed a bra from the bathroom.  No exposure.  No social.

Small Stash – I found several more pairs of stockings that I hid in my room.  At one point, my mother found my stash.  I threw them all away.

Borrowing – I started borrowing clothes from my mother and sister.  Normally they were items waiting to be cleaned.  Sometimes, I would visit my mother’s or my sister’s dresser.  I know this is an unpopular thing for someone to do.  At the time, it was my only choice and I did not perceive it as an invasion of privacy.  I never thought twice about it.

Just pantyhose – I know that I tried on slips and bras, etc.  But primarily, I was attracted to the feel of pantyhose.  With hose on, everything felt silky.  Slips on hose were particularly nice feeling, but I do not remember spending much time in a slip.

Sexuality/Puberty – When I hit adolescence I discovered my own sexuality while I was crossdressed.  This new part of life sort of invaded my crossdressing.  I feel like it polluted it.  Before, my dressing was rather innocent and tactile.  Puberty caused it to be more selfish and carnal.  For many years after this, if I ever needed to address my body’s urges, I did it in conjunction with crossdressing.  On the positive side, I think this outlet kept me from pursuing other carnal behaviors, whether physical or visual, to address this urge.

Other Clothes – I do not remember when, but I started branching out into other clothing items.  I wanted to be able to experience looking pretty.  I wanted to wear some shoes with my hose.  I wanted to try on a dress.

Night Outing – As I got old enough to be home alone, I dressed around the house.  I started to get the idea to go outside with something on.  I walked around the outside of my home with only women’s clothing on.  Our neighbors were far enough away that it was quite safe in the dark.  Almost no exposure.  No social.

Light Outing – I started craving going out in the daylight.  I believe that the craving to dress overpowered my fears about the risks.  I did not want to be found out.  I think I did not want to be seen.  However, altogether, this is not logical.  I wore skin-toned pantyhose with shorts for a walk/jog around my neighborhood.  When I came upon someone (100 yards/meters) away, I started jogging in almost a panic.  It was such a thrill to be seen by someone while I was wearing something, even though there was such a low probability that they would have noticed.  Low exposure.  No social.

Purges – Occasionally during this period, shame and guilt would result in me wanting to quit crossdressing.  I would throw away my stash of clothes (which were normally a collection of discarded pantyhose).  Later, I would regret purging and have to start collecting a new stash of clothes.  Sometimes this purge/replace cycle would be shorter than the trash cycle and I could retrieve my clothes from the trash can.

Confession – When I had my first serious girlfriend, I started feeling the urge to confess to her.  No one knew about my secret (assuming my mother had not figured it out).  I eventually confessed it to my girlfriend.  I confessed it as a bad thing I did.  She perceived it as a bad thing, too.  I stopped for a while for her, but I eventually gave in.  Later, I realized that telling her was a mistake.  After we broke up, she had a powerful weapon over me.  I do not know if she told anyone, but some subtle clues make me I fear that she did.

First Purchase – I went to a grocery store to buy some pantyhose for myself.  I was so scared.  I bought 20-30 dollars of unneeded groceries in order to buy one 5 dollar pair of pantyhose.  I started regularly purchasing my own pantyhose.  I grew more comfortable.  I stopped borrowing.

Comfort in Purchasing – Eventually, I would go to the grocery store and buy one pair of pantyhose and nothing more.  The cashier would seldom show any sign of interest or surprise in what I purchased.  Sometimes, the cashier would make a humorous comment because she assumed they were not for me.  I would joke around with the cashier about them.  I became comfortable enough to shop at the grocery store near my home.  I even bought higher-end pantyhose at department stores.  There, sales ladies would approach me.  I would not mention that the hose were for me.  They would not ask.  However, in retrospect, they probably had enough male customers to know they were for me.  Mild, selective exposure.  Mild social

Shopping For Myself – I discovered that in lingerie stores, I could buy pantyhose for myself and admit that they were for me.  I felt like the salespeople in those stores would be more open to crossdressing than in other stores.  High, selective exposure.  Mild social.

First Dressing Room – The first time I tried on women’s clothes in a store was while I was in another city.  I was in a women’s clothing store in a mall.  A salesperson had spoken to me once already, but she did not know I was shopping for myself.  After browsing the store, I nervously asked the woman if they allowed men to try on clothes.  She surprised me by how she immediately responded with an energetic, “Oh, sure,” and then proceeded to set up a changing room for me.  I had no idea that this was something salespeople occasionally dealt with.  High, selective exposure.  Mild social.

The Internet – Once I got onto the Internet, I started to discover that there were a lot of guys just like me.  I was on AOL and I discovered chat rooms where guys like me would discuss crossdressing.  One was called, “Wearing Hers”.  The conversation was almost always about what we were wearing and what we have done while dressed.  I learned that I was not alone. Low exposure.  High, indirect social.

First Major Purge and Stoppage / Accountability – I stopped dressing for almost a year.  I confessed my crossdressing to someone and they tried to help me be accountable.  I discovered that when I did not have crossdressing as an “outlet,” that I was susceptible to other temptations.  During this time, even though I did not put on any women’s clothing, I never stopped thinking about and desiring to wear them.

Web Presence – I created a web site about my efforts to stop crossdressing.  Other men, like me, were trying to stop.  I was astounded by how many hits I would get on that site.  I think it got 200000 a year, if I remember correctly.  I think many of the hits were from people searching for ‘crossdressing’ and ‘pantyhose’ topics.  I do not think they were interested in stopping crossdressing.

First Costume / End of Stoppage –  I had an opportunity to dress up as a girl for a costume.  My girlfriend, and eventual wife, helped me.  She did not know that I was a crossdresser.  I bought pantyhose in a department store near home and confessed that they were for me for a costume.  I went out in public for the first time in a dress.  My girlfriend was with me, in public, while I was dressed in a dress, pantyhose, a wig, and makeup.  She did not hate me.  I am way too tall to easily pass as a woman.  The general public saw me and, of course, read me.  Several people laughed, I received a lot of strange looks, but I did it and I loved it (but it was very scary!).  Slowly, after this event, I started crossdressing again.  High exposure as costume.  High social.

Confession to My Girlfriend – While I was still in the previously mentioned stoppage, I confessed to my girlfriend that I was a crossdresser.  I told her that I had stopped.  She did not like it.  She did not want me to crossdress.  She tried to be understanding.  I wanted to let her know about this before I asked her to marry me.  As I said previously, I eventually started crossdressing again.

Pantyhose and Shorts Outing – I drove to a town sufficiently far from my home.  I bought a pair of pantyhose for myself at a lingerie store.  I asked the salesperson if I could put them on in the changing room.  I put them on under my shorts (unshaved legs).  The salesladies said that the pantyhose were not noticeable.  I gathered my courage and walked out of the store and went to a clothing store.  I was so scared, but no one noticed.  I bought some pantyhose for myself in the department store while dressed like this.  I pointed out what I was wearing to the saleswoman.  She had not noticed.  I became slightly relaxed.  I went to a grocery store.  Even though a couple people appeared to notice what I was wearing, no one reacted other than by looking.  Mild public exposure.  Mild, selective social.

Marriage – I hoped that being married would help me stop crossdressing.  I thought that having a wife would burn off the sexual energy that I believed fueled my dressing.  That was not the case.  The first time I gave into my urges after being married was within the first few months of marriage.  I cried bitterly.  I had failed my wife.  I could not beat this.

Non-Secret Stash – I started keeping some pantyhose in my underwear drawer.  My wife knew about them.

Other Stoppages – The time line for this is intermixed with future events on this list.  I stopped crossdressing on two other occasions for significant amounts of time.  The crossdressing never left my mind even though my actions changed.

Dressing In Front Of My Wife – A few times in the first year or two of marriage, I dressed in my wife’s clothes while she knew about it.  We had a few good laughs.  Sometimes, I would wear pantyhose and shorts around the house.  At some point, she allowed me to wear whatever I wanted to while cleaning the bathroom.  High, selective exposure.  High, selective social.

Other (Somewhat) Public Outings –  My wife and I moved away from where I grew up.  After dark, a few evenings, I wore shorts and pantyhose and took a walk.  On some of these occasions, I wore hose that were significantly darker than my skin color.  I avoided people.  No one ever knew.  Low exposure.  No social.

Don’t Ask, Don’t Tell – My wife’s discomfort with my crossdressing grew.  I stopped dressing around her.  I started to hide it from her if I wore anything.

Halloween – One Halloween, we decided that I would dress like a woman and my wife would dress like a man.  I went shopping and the sales person helped me find a dress for my costume.  I tried on outfits and showed the salesperson.  I bought my first bra.  Halloween came and my wife and I went out in public.  We did not do much.  Eventually, we rented a movie and went home.  We showed our neighbors our costumes.  I think they knew I looked too polished.  Medium exposure as a costume.  Low social.

Halloween at Work – A couple years later, I wore a skirt and heels to work for Halloween.  I did not wear a wig or makeup.  High acquaintance exposure as a costume.  High social.

Public Invisible Outings – I went out of a few occasions wearing all women’s clothes as a man.  I wore a plain blouse, pants, and casual shoes.  No one noticed, but I was in public in all women’s clothes.  Low public exposure.  No social.

Leg Shaving – I started shaving my legs every winter.

Morning Walks – I started taking morning walks in shorts and pantyhose.  This became a regular event.  I transitioned from shorts and skin-toned hose to darker hose and eventually skirts.  Some evenings, I would take walks in pantyhose and shorts.  I would pass other walkers.  It was a non-event, but they did notice the skirts.  High public exposure.  No social.

Shorts and Pantyhose in Public – I started going to public places far from home in shorts and skin-toned pantyhose.  I even tried wearing some slightly darker hose with shorts.  I went to shopping malls, barber shops, restaurants, etc.  Most people never noticed, but some did.  The worst that ever happened was a couple people gave me disapproving looks.  Some of these times, all of my clothes were women’s.  I do not know why, but it is fulfilling in a different way to be wearing 100% women’s clothes than to wear partially women’s clothes.  Medium public exposure.  Mild social.

Shorts and Pantyhose Around Someone I (Barely) Know – I wore pantyhose and shorts to the office at my apartment complex a few times.  If the staff there noticed, they never mentioned it.  Medium, selective exposure.  Medium, selective social.

Christmas Shopping in All Women’s Clothes (shorts) – I did my Christmas shopping in pantyhose and shorts one year.  I wore all women’s clothes with pantyhose and shorts the next year or two.  It was not a big deal.  I loved it.  I was losing my inhibitions little by little.  Medium public exposure.  Mild social.

Shorts and Dark Pantyhose in Public – I went out in public in dark pantyhose and shorts.  People definitely noticed.  There were a lot of double takes, but no one said anything to me about it.  I went to a few stores, a restaurant, a couple shopping malls.  I was becoming more comfortable with being seen and noticed.  I was learning that I did not have to pose as a woman to wear women’s clothes.  High public exposure.  Low social.

Wearing a Skirt as a Man in Public – I went to a clothing store and to a mall in a skirt, blouse, black pantyhose, and flats.  I did not wear makeup or a wig.  I was a man in women’s clothes.  Anyone who looked at me could tell.  Many people saw me.  Only a couple teenage girls laughed.  Some store clerks talked to me and they were completely professional.  I realized that I can wear skirts and go out in public.  Highest public exposure.  Low social.

Pantyhose and Shorts on a Trip With My Wife – My wife and I went on a road trip.  For two days, I wore pantyhose (shaved legs) and shorts and did whatever I would have done otherwise.  My wife was basically comfortable being with me in this outfit around other people.  It was the first time I was with someone in public while dressed in something other than a costume.  Mild public exposure, high friend exposure.  Mild social (with the public).

Two Year Stoppage – At some point around here I purged and stopped for two years.  The thoughts never left me.

Flying in Women’s Top, Pants, and Shoes – I flew in all women’s clothes.  I wore slacks, a plain blouse, and non-remarkable shoes on one leg of a flight.  A few people could tell.  At this stage, I was subtly crossdressed around people in a situation I could not escape.  Medium public exposure.  Mild social.  Low control situation.

Christmas Shopping in a Skirt as a Man – I drove an hour away from home and dressed in a blouse, skirt, pantyhose, and ladies’ shoes and did all of my Christmas shopping.  I went to malls, stores, etc.  This was crossdressing with a purpose.  This was so much better than what I had ever done before.  Purpose made a big difference.  I was more in public by doing this.  I was not just going to women’s clothing stores.  I was standing in line with other customers, etc.  Very high public exposure.  Medium social.  High and low control situations.

Volunteering in a Skirt – A store where I occasionally shopped that was over half an hour away from my home allowed me to come in and help out for a day.  I wore a skirt, blouse, hose, and heels.  I had control of the situation because I could sneak away with my emergency bag and change if I needed to.  Here, I got to know people and work with them while crossdressed.  They were free to talk openly to me and get to know me.  High public exposure.  High selective social.  Medium control.

Flying in a Skirt – I wore a skirt, blouse, hose, and flats on a plane trip.  I wore this from the rental car facility, on shuttle buses, through security, to the gate (a long walk past a lot of people), on the plane, at baggage claim, and on the shuttle bus to my parking lot.  I was absolutely out of control.  I think I did not have men’s clothes in my carry on bag.  I had no ability to hide as I walked to the gate.  I had to use the men’s room this way.  I had to sit by someone on the plane this way.  This was very risky, very public, and included holding conversations with the woman sitting beside me on the plane.  Very high public exposure.  High social.  Very low control situation.

Barber Shop in a Skirt – While a good distance from home, I went to a salon/barber shop and had my hair cut.  I was comfortable enough to get stuck in a room with mostly women, and stuck in a conversation with one woman.  Again, I was in a situation where I had little control and I was allowing myself to have a conversation with some arbitrary person.  Very high public exposure.  High social.  Medium control.

Becoming a Known Regular at a Store – I started shopping in the same few clothing stores enough that the staff began to know my name and what my style was.  I was forming relationships with people who knew a little about my identity.  Very high semi-public exposure.  Very high social.  High control.

Attended a Non-Crossdressing Meeting in a Skirt – I attended a couple meetings with about a dozen people who, I felt, were rather accepting of uncommon people.  I did not mention I was a crossdresser when I signed up to join the group.  I participated in the discussion during the meetings.  I formed shallow relationships.  I was comfortable forming relationships with the public while crossdressed.  Very high public exposure.  Very high social.  High control situation.

Attended a Crossdressing Meeting – I do not know if this is well placed in this progression.  I wanted to go to a crossdressing/transgender meeting to see how normal I was.  I wanted to get to know other crossdressers.  Many crossdressers do this long before the go out in public.  This was a low risk, moderately high control situation.  I formed no real relationships.  However, I got to meet other crossdressed people.  Unfortunately, most were transgender and, therefore, unlike myself.

Halloween Ballroom Dancing in a Dress –  One year, my wife and I both crossdressed for Halloween, but we did not change our faces.  I wore a black dress, and heels.  We went ballroom dancing.  I was fully dressed, in public, with my wife, around people who know me.  I learned that arbitrary women will dance with a man in a dress on Halloween.  My wife enjoyed herself with me while I was crossdressed.  High exposure as a costume around acquaintances.  High acquaintance social.  High control.

Becoming a Regular at a Restaurant in a Skirt – Some days during lunch from work, I would drive about twenty minutes away from my home and my work and eat lunch in a restaurant.  This was a moderate exposure, low control (I could not leave without first waiting to pay), slight relationship situation.  One man on staff served me a few times.  He always seemed happy to see me.  Very high exposure.  Mild social.  Mild control.

Dancing in a Skirt – I went swing dancing in a blouse, colorful skirt, black hose, and flats.  Most of the other dancers were much younger than me.  I found that women will dance with a man in a skirt even if it is not Halloween.  Very few mentioned my clothing.  I was even asked for a dance by a woman.  This was the most social experience I had ever had while crossdressed and it was not Halloween.  Very high public exposure.  Very high social.  Medium control.

Becoming a Regular at a Barber Shop in a Skirt – I started driving about twenty minutes from work to a hair salon on a recurring basis.  I formed a social relationship with my hairdresser.  This is a low control situation, and it is a recurring social experience.  Medium public exposure.  Very high social (with friendships forming).  Medium control.


So, where is this heading?  My wife would like for there to be no progression.  I would like to become content at some point as well.  I think that the most likely progression would be toward me becoming a regular in a class or group that is not crossdressing related.  I would not be surprised if I eventually taught a class or something while dressed.  I do not want to become a full-time crossdresser in my normal life.  I do not feel a draw to high exposure with my friends.  I would like to have friends who know I crossdress but do not care and are not necessarily crossdressers themselves.

The progression seems to drive me to go from secrecy toward public and from hiding from the public to engaging them.  My progression does not seem to be driving me toward changing my gender.  Neither does it drive me away from my exclusive heterosexual relationship with my wife.  I feel like I am approaching living a boring pattern of reasonable behavior for a married father of young children, but occasionally in a skirt.

I hope this was interesting and informative.  I am interested in hearing how my progression differs from other crossdressers’ progressions.


From → Information

One Comment
  1. Your progression is similar to my own and in spots almost identical. For example my first outright purchase of pantyhose was “No Nonsense” brand at a supermarket. As a kid I would on occasion invade my mother’s closet when the opportunity arose. As the oldest I sometimes would babysit my sibs and would look for an chance after they went to sleep and my parents came home.

    I often describe my “coming out” as a CD as the slowest in history. I am almost of retirement age and still progressing.

    In the 1970’s I had a job that had me working both inside and outside. In winter I found the long johns rather uncomfortable. I had had my wife dress me on a few occasions early in our marriage until my liking it really put a scare in her but she had some old tights that she gave me to wear under my pants.

    Also back in the 1970s and into the 1980s I did a bit of jogging. Nothing worked better for me than wearing pantyhose or tights under my running shorts. There was something special and unique knowing what I was wearing and knowing that if anyone paid close attention to me that they would figure it out.

    In the 1980s I got my current job and back then we wore suits. I would have a long walk to and from the train to the office and wore out the suit pants well before the jacket and vest got much wear. I started to have my slacks lined with nylon. I also found that wearing pantyhose under my slacks prevented thigh chafe and extended the wear of the suit pants. As such I have been wearing pantyhose under slacks for decades. In recent years, except when exposure would spell major issues, I will wear my hose without covering them with socks. If anyone looked closely they would be able to tell that I was wearing hose but other than my wife I doubt this has been noticed.

    I do admire your getting out and about in your dressed mode. I hope to give it a try.


    PS: I also find it amazing that I have such a precise memory for so many of my CD milestones

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