Chronology of a Crossdresser

[Miss Mandy]

Come with me on a journey backward into the dark recesses of time, many decades, and countless moments, to unravel the emergence of a crossdresser. Was I born this way or did my circumstances form me? I know not. My story is much like yours to be sure. Perhaps you will recognize many elements, perhaps you will not..

After reading this, please tell us your story!!!

The Story of Jessica

1975: Born in medium-sized city in the South.

1979: Mom dressed me up in my older sister's cheerleading uniform as a joke

1979-1986: Lived a completely normal boy's life: Football, baseball, playing army in the woods, hunting, fishing, hiking, etc

1987: Puberty hits; become interested in girls, look at girly magazines, yet strangely, one late night after playing Nintendo, I sneak into my mother's room and steal a pair of her pantyhose. I try them on. I love it!

1987-1989: Mom gets a job; I have the house to myself in the afternoons; start trying on her lingerie and make-up.

1990: I go to a local Frederick's of Hollywood store in the mall and sheepishly buy a pair of thigh-high fishnet stockings. The young, attractive sales lady only smiles as I pay for them. As I walk out of the mall, I unexpectedly meet my uncle there...he asks why I'm carrying a pink store bag... Later that year, I spend an afternoon at my newlywed sister's house for a birthday party; I sneak inside and ramble through her underwear drawer and discover a garterbelt. I put it and her stockings on and nearly get caught by her husband...

1991-1993: Work at a local grocery store as a bagger and checkout clerk. As I take out the groceries of an attractive 30-something women to her sports car, she lights up a Virginia Slim 120 and tells me that I bet I would like to smoke one and dress up as her little sissy girl...wow, what a thing to hear as a 16 year old boy.

1993-1995: Graduate HS; enter college; CDing takes a hiatus.

1995: Discover the Internet; start making CD search queries

1996: Mom gets a job at a local Bed and Breakfast; local scandal is created after B&B owner's husband is discovered to be a CD. I am secretly intrigued...

1997: On a January night, I make a secret 2-hour trip to Ritzy Rags (closed now) in Atlanta, GA to have a makeover. I am young, thin, and make a great blond. Not bad for the low, low cost of $100. On the way home late that night, I chose "Jessica" as my femme name; Meet my future wife (an only child) in late 1997 and tell her that I like to wear women's clothing after the third date. She is excited to finally have a "sister" to play dress-up with.

1997-1999: Courtship with future wife; play dress-up on multiple occasions (often with her sleeping parents just a few rooms away...he he)

2000: Married; move out of parents house, buy a collection of lingerie, shoes, and thigh-high boots; Wife dresses me up on our overseas honeymoon. Nothing like a corset, thigh-highs, forearm length velvet gloves, and full make-up on in a B&B in the British Isles...

2000-2003: Dress often, wife buys me a wig, build a secret "dressing room" in the dark basement of our first house.

2003: Wife grows cold to my obsessive dressing; only major purge (costing hundreds of dollars); resolve to "quit" ha ha

2003-2006: Move to New England; little to no dressing until I decide to walk into a near-empty lingerie store near Boston, MA around 10:00 AM. Ask for a Rago corsolette in 42 D "for my wife". Older sales lady smiles and then asks me if its really for me...I blush, break down, and admit that it is indeed for me and she shows me to the dressing room. I buy it and start dressing again off and on.

2007: Move back south; wife is only barely lukewarm to dressing now.

2008: Sneak off to Phoebe Cross in Atlanta, Ga for an overnight stay and makeover. Only tell wife about it two years later.

2008-2010: Occasional dressing; Children come into the picture: career hits high gear.

2010: Start to dress more frequently; buy more women's lingerie (with the consent of my wife)

2011: Buy make-up and wigs for first time in years; start cleaning and doing chores for my wife; she buys me a maids uniform. She amazingly becomes completely at ease with my dressing once again. She even suggests we take a trip out of town in the near future with me in femme. I begin to find a peace once again...

To be continued,

Miss Jessica

[Anna Lorree]

Move the dates back 2 years, put it on the West Coast, have the 30 year old woman take your virginity without wanting to dress you, change it up so your wife doesn't find out about your dressing until 11 years after getting married, and make it so your wife still hasn't really accepted dressing. You do all of that and it pretty much fits my life. Oh, I never bagged groceries, but I did work for an interior decorator.

Anna

[Marleena]

Great post Jessica! I'm sure many of us can relate to some of this chronology. 2012 will be even better!

[miaTX86]

2003-2006: Move to New England; little to no dressing until I decide to walk into a near-empty lingerie store near Boston, MA around 10:00 AM. Ask for a Rago corsolette in 42 D "for my wife". Older sales lady smiles and then asks me if its really for me...I blush, break down, and admit that it is indeed for me and she shows me to the dressing room. I buy it and start dressing again off and on.


3 years in a lingerie store!!! Oh my, what a dream ;-)

I love that you are re-exploring this. I think that cross dressing is a thing that sticks with most of us and it is unhealthy to deny it.

[Karren H]

1975!!!! ...... Graduates from college and gets married... Sigh...

[Jenny Doolittle]

Amazing how similar your story is with so many others. I also had a few of the highlights, but you did not mention the self doubt about who you were as a kid, how weird you felt and alone until the internet came along.

I thank God I finally found my true identity and am happy as a person now, and that is because of a lot of friends I have met along the way in forums and rooms like this one.

[kimdl93]

I gotta say, I envy the way your life has progressed. I'm happy with my life and have a very supportive wife - but other than that brief lull - you've had tremendous spousal support and a great time!

[Sister Rachel]

Oh bless you, sweetheart .. good on you :-)

... but "many decades" ? I remember JFK's assassination :-S

[AlexisRaeMoon]

Alright - I'll bite. I've been thinking about doing this for a while, so you've given me a reason.

The Story of Arianna

1972 - Born in the Chicago suburbs

1977 - Start kindergarten. One of my good friends starts dressing up in the ladies clothes in the dress up area. I'm secretly jealous. One time, when playing at his house, we start shoving plastic balls in our shirts to pretend we're girls. Another time he decides we should look through his mom's drawers because she has "stuff that would fit us." I freak out and leave - too weird for me.

1978 - 1985 - Normal suburban boyhood. I'm a little bit of loaner and don't have a lot of friends, but a few are very close. I'll occasionally stuff some socks in my shirt to see what it feels like. Whenever a TV newsmagazine program has anything dealing with cross dressers or drag queens, I'm glued to the set. I remember loving a particular episode of Silver Spoons where Ricky Schroeder has to dress up like a girl to be his buddy's date. He was cute!

1985 - Junior high - cue ominous music! The summer in between 7th and 8th grade I discover that my mother's shoes fit me. I find a pair of panty hose and heels, and try them on while my brother plays outside with a friend. Minutes later, the postman delivers a mail-order Star Wars figure. Sheesh...I remember later on distinctly feeling like, "Oh god - I can't believe i just wore women's' clothes. I will have to live with that for the rest of my life!" As I started getting more time alone in the house, I began trying on more things.

1990 - I didn't go away to school, but even though I commuted to college, any interest in dressing subsided during freshman year. Until the very end of the year, when I very bad social experience sent me running for the closet at home. Sporadic dressing up continued until 1995...most of it was accompanied by significant guilt, and lots of dark thoughts. I would try to cure myself of dressing by trying to remind myself of how godawful it would make me feel afterward, but that never seemed to last - the urge was like a monster that would take control when the opportunity arose. I'll never forget the first time I looked in the mirror and thought I really looked like a girl. It was a rush like I'd never felt.

1994 - I got my own computer, and my first AOL account. First thing I look up? You guessed it. I suddenly began to realize that there others out there like me. Through chat rooms, I even met some local people that I might possibly have met up with but then...

1995 - I meet and begin dating the love of my life. As soon as it was "official" I deleted the AOL screen name I used for CD chatting, but I'll never forget the moment of hesitation before I confirmed the deletion. Something just felt off about shutting that part of me away. But I'd always believed that cross dressing and a relationship were mutually exclusive. I know some strongly question how you can even enter a relationship with someone without disclosing your need to dress, but in my case it was something I was extremely ashamed and embarrassed of, and I never had any plans to tell another living soul about it. And now that I was in love, the urge to dress would just fade, right?

In my case it actually did. I wasn't able to go totally cold turkey, but after a few months of dating our relationship moved to a higher level, and my urge to dress was gone. I did not even think about it.

1996 - My girlfriend and I get engaged. We are totally happy and excited and life is good. We go out to celebrate New Year's Eve, and she's wearing these amazing T-strap pumps, that of course hurt her feet. When we get back to her apartment, she puts one on my foot. It fits almost perfectly. After not even wanting to dress for like 13 months, it's like getting hit by a lighting bolt. I nearly passed out! All the good feelings came rushing back in that one brief instant. Once I knew that her shoes fit, I couldn't wait to try them on again. After we started living together, I realized her clothes fit too. I was doomed.

1997 - 2001 - Wedded bliss, and lots of angst (on my part). The guilt is nearly crushing at times, but the fear of rejection is greater. I realize know that the main reason I was so convinced I would be rejected, is because I was ashamed of myself. Everytime I would dress, every single time, was going to be the last time. Hands down - no questions asked. I wish I had a dime for every last time I wore a dress. After my first child is born, I again successfully stop dressing. The pattern, I notice, is that the only times I successfully stop, is when I don't make a conscious decision to. It just happens organically. After the horror of the 9/11 attacks, though, I find myself back at it again. Screw it, I thought, life is too short.

2005 - My first weekend alone in the house, the wife and kids are away. I decide to celebrate by buying my own pair of black heels at Wal Mart, and a wig. I'm so nervous I can hardly stand it. My stomach feels like it has a pit of ice in it all day long. But at night I'm able to dress for as long as I want without the fear of getting caught. The next day, I'm so freaked out, I throw it all in the garbage can. This wouldn't be the first of these episodes, either.

2008 - I dress up as Sarah Palin for a Halloween party. I wear a black suit, heeled boots, wig, makeup, the whole nine yards. My wife helps me fix my hair and gives me jewelry, and tells me to carry a purse. It was one of the greatest nights of my life, and the perfect opening to tell her how much I actually enjoyed myself. Of course, I wimp out.

2010 - I reach a low point, when a musical project I've sunk my heart and soul into falls apart. After having many bands fail, this is the last straw. I begin retreating more into the online CD world, spending too much time looking at pictures and reading about it, when one night it finally dawns on me - this is who I am and it's never going to change. Part of what helped is a fantastic blog written by a Hope Alexander over at hubpages.com. Go there and search for her. She has written a number of great articles about men who like to wear women's clothes, and why it's not a big deal, and several articles on telling your SO. I make up mind that I will tell my wife about my crossdressing. Later in the year I begin taking pictures of myself, and find that it's a fun thing to do while all dolled up.

2012 - Unfortunately, I'm still searching of the courage to have an open and honest discussion with my wife about all this. I know it's not fair to her, and I should've opened up a long time ago. But first, I needed to accept that this is who I am, and not be ashamed of it. It's been a long road to reach that time, because even 5 years ago, I would never have dared even consider telling anyone I know about this. Now I'm considering telling the single most important person in life. It's coming soon, I can feel it.

To be continued...

[Foxglove]

Great posts, Jessica and Arianna! No need for me to add my own chronology. Spiritually and emotionally, it's so close to yours that it would just be mere repetition. It raises the question in my mind, how could all this be different? How could people avoid having to live their lives like this? Only if everybody--we on our side and they on theirs--would open up completely about this. It's really sad to look back on a life lived with such unnecessary psychological pressure. Yes, there are good times there, too, and some happiness as well, but you never really get to the bottom of things--and that's where all the difficulties lie.

Best wishes, Annabelle

[Miss Mandy]

Thanks for sharing your history Arianna...I hope our other ladies will empty their hearts and give us a rundown of their secret lives. Such confessions are very cathartic...

[AlexisRaeMoon]

Thanks, Jessica. It is very cathartic! I notice when I compare our stories that they diverge when we meet our future wives. I respect you so much for making the right decision and just telling her about your crossdressing so early on. I wish I had had the courage to do the same, but I chose to spend the next 15 years convincing myself that the only choice available to me was to force myself to stop. I realize now that's not going to happen, and this forum has been an amazing source of encouragement.

[NicoleScott]

1991-1993: Work at a local grocery store as a bagger and checkout clerk. As I take out the groceries of an attractive 30-something women to her sports car, she lights up a Virginia Slim 120 and tells me that I bet I would like to smoke one and dress up as her little sissy girl...wow, what a thing to hear as a 16 year old boy.


My reply: "Well, I don't smoke but,....uh.......what was that other thing you mentioned?"

Similar to my fantasies at the age. I just finished mowing the woman's yard. She invited me in and offered me a shower while she laundered my dirty, sweaty clothes. She had a surprise activity waiting for me to pass the time while the clothes were in the dryer. Never happened to me, though. [sigh].

[darci.c]

only because you asked -


1985 - born, denver colorado

1990 - first time "stealing" pantyhose, legwear, dresses, etc. was in a situation where an older cousin of mine had her school twirling outfits & stuff and i could get to it. i found it irresistibly alluring. snuck into my bedroom with the stash, closed the door (it didn't lock) and pushed the dresser over in front of it in case someone tried to get in. although nothing fit me since i was so small back then, looking back i found it remarkable that i was able to have an erection at only 5 years old

1990-2001 - made friends with a lot of girls... if i ever got lucky i would kick their clothes under my bed hoping they wouldn't find them in the morning. came up with a small collection which i would wear underneath my boy clothes when i went to school

2002 - realized i was what they call "bi". was absolutely in love with a guy at school, wanted to be his girl more than anything. he was straight. i was celibate. and yet, i loved girls.

2004 - 2008 - went to college. spent a lot of time ashamed and hiding. started to spend hundreds of dollars a month buying women's clothing. half of my time spent on the internet was "window shopping." believed i was one in a million, and would never really know anyone else who felt like me. remembered one of my high school teachers who confided privately that mushrooms really helped him with psychological and personal issues.

2007 - was with a girl who was into lingerie. had a lot of fun with her. spent one night stoned and drunk... the next thing i consciously remember was that she was waking me up and making a big deal of the fact that we went to bed naked and i woke up wearing her lingerie...

2009 - ate 6 grams of psilocybin mushrooms. came back having shed all pretenses of insanity, self-deception, and fear. had my first multiple-partner sexual experience. there were six of us, and we were all out of our minds, and it was by far my most cathartic physical experience of my life.

2010 - moved to a real city (no lame-ass southern half-somewhere nowhere kind of place) and visited a few gay bars. met some queens, fags, hags, and had sex on both sides of the coin. learned a lot about myself, and humanity

2010-present day - dress publicly when being social, and at least half the time when at home. i don't dress at work but it's just not going to happen. otherwise... far more accepting and comfortable with myself.

[docrobbysherry]

Wow! I may have had DREAMS like u girls seem to. But, if I do, I can't RECALL THEM as well as all of u do!

[Vickie_CDTV]

Jessica, neat story, we are about the same age (I played a lot of Nintendo when I was a kid too!) Wow, I wish I had the courage to buy stockings when I was 15. I *so* wanted a pair, but didn't have the nerve to do it.

My first relationship was with an older woman too, though I was 21 at the time (it was my very first relationship, and the first woman I was ever intimate with.)

[Jaimie]

I saw this post and I wanted to make my own timeline so I did. To see my timeline click the link below. I think this is my 10th post too, so yay.

http://timeglider.com/app/viewer.php?uid=line_4f6cb30fc3eb920eca082e39a06495 0a

Jaimie