Caught: how is your experience evolved over time?

This month, I celebrate 50 years of crossdressing (age 13 to 63). I began by sneaking into my
mother's closet with the attendant guilt, shame, and secrecy. As my own feelings and practices have evolved, so have my feelings on getting caught. THe three most important things I have learned are: 1) the CD habit is rarely the problem. It's the lying and sneaking into her panty drawer that she detests. 2) Respect your wife, girlfriend, sister, room mate, etc. enough to stay out of her things. And 3) only shame will give an aggressor leverage and motivation to make a scene. If I own it, there is no drama.

THese days, I'm out to any new girlfriend by the third date. This has many advantages, most notably, she only has to deal with my crossdressing, not being lied to or whatever scenario her stimulated imagination can come up with. I'm also out to my neighbors, close friends, and anyone who needs to know.

My worst story was at 14. I had advanced to having my own stash and my mother found it. Niether of us wanted to have that conversation and she accepted my BS story of how I had found them and had been meaning to send them off to the thrift store for donation. Like most 14 yo males, I had 1000 times more faith in my ability to lie than was justified. I'm sure she knew but she didn't press the issue.

I really don't care who knows but I tell anyone close before they find out on their own. I generally find a way to piggy back it onto an existing topic of conversation. My attitude conveys: no big deal. The best reward is freedom. I come and go as I please using the front door, in broad daylight, while fully dressed. If I hire a woman for house cleaning off of Craigslist (online bulletin board popular in the USA), I tell her up front so if she finds an article of clothing, she won't feel akward about it. Likewise, I thank any cashier I meet for her understanding. All have smiled and said it was no problem 'sweetie.' These are fun and healthy ways to own what is. At over six feet tall (>183 cm), I am not passable. The truth is, no one really makes a big deal of it anymore, especially because I own it. I'm regularly out in public. I have attended events, used the ladies bathroom, checked into hotels, and even been pulled over by the highway patrol; all while dressed as a girl. Women find it far easier to talk to me when I'm in girl mode. Men often avoid eye contact. Beyond a few teenage boys who snicker, no one makes an issue of it.

Of course, my fantasy is to be caught by a beautiful dominatrix in high heels who will administer a firm spanking. Hasn't happened yet but I'm ever hopeful.

So girls, what's your best and worst 'getting caught' experience? How did you feel? How did you handle it? What mistakes did you make? What advice for the rest of us?

Women you hire off of Craigslist?

Err. Is that what I think it is?

Lol, I am guessing those are women hired to do chores of a non-soliciting type.

I was pondering this post to think of a time when I might have been caught. Oddly, I could not come up with a single event. There have been, however, many times when I have come out to friends and former colleagues (I have learned to keep work and my private life separate).

What I have found somewhat disturbing are my occasional failures to take an opportunity to claim ownership of my gender identity in situations where it might have been appropriate. Although in saying that I also am somewhat cautious about the possibility of using coming out simply for the thrill of it. That feels a bit like exhibitionism to me and something of an imposition on others.

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Originally Posted by CharlotteCD

Women you hire off of Craigslist?

Err. Is that what I think it is?

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Probably not. Just house cleaning.

Charlotte, I have hired a house keeper off of craigslist as well. Nothing nefarious.

Being ?caught? drove me deeper into hiding and into a storage unit. I became more careful and discreet. It encouraged me to learn better communication and detection of subtle clues.

Ha ing gone full time female dressing there is little I haven't done. There is no hiding it to get caught. Yes I've even been stopped by the police for a light being out but stopped none the less. One thing I haven't done is fly not out of fear but opportunity. That is going to happen in next week or two I believe. I am actually looking forward to this and have no intention of leaving any doubt what type of clothes I'm wearing.

I became a teenager in the early 1960's. Society's equation was cross dressing = homosexual. Totally confusing for a teenage boy who lusted after unobtainable movie starlets (Annette Funicello) and neighborhood young women. I had no access to women's clothing other than my mother's until I outgrew them. My parents had to know it was probably me who played in her lingerie draw, and, snap the strap on her black bra. They tried to catch me, and, almost did. They left our apartment together with my little sister. I quickly donned a sun dress and peaked out the window of the sixth floor apartment to watch them. I didn't correctly gauge how quickly the elevator could get to the sixth floor. Still wearing her dress I heard the key opening the apartment door, but the security chain stopped them from entering. I quickly striped and got back into my boy clothes. When I let them in, it was inquisition time, but, they did not have any evidence. If I had been "caught" I am sure my ass would have been pulverized.

I can understand why women are not appreciative of finding out their husbands are cross dressers. Call it what you may; cheating, lying by omission, out right lying. They do not understand the societal pressure put on cross dressing men; especially from learned experiences in the dark ages of the 1950's and 1960's.

My wife? We dabbled with lingerie (nightgowns and stockings) in the bedroom until my interests expanded and she discovered a bra. When it went from a little "bedroom kink" to more, she shut down; "If I wanted to be married to a woman, I would have married a woman." Ultimately, she gravitated into an ostrich. Although, she does not ever comment on any cross dressing, she was cleaning out some of her stuff. She put a small pile of totally lacy panties on my side of the bed that I never saw before; totally not her style anymore. Hmmm?

Since I only started crossdressing a short time ago, the only person that I was concerned about "catching" me was my wife. Trying to hide anything at all, much less something like this was a useless endeavor and caused way too much stress, so I came out right away and faced whatever consequences awaited me. Fortunately, things worked out fine.

So, at present I have not been caught. However, my adult children do not know and could conceivably catch me. Should that happen, that will be a story in itself!

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Originally Posted by JenniferMBlack

= One thing I haven't done is fly...

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Just realized I didn't include one of my fav ways to get caught. Flying pretty is fun but it can be akward to sit next to a stranger for several hours while dressed. To avoid this, I usually board in male or bybrid mode and bring my things in a bag. I sit near the back and after landing, duck into the rear restroom to change and appear as Heather. Cramped but doable. The flight attendants always notice and I shoot them a wink. I so love to click down the tile floors of the airport in a skirt and high heels, and if some of the passangers see me at bag claim, I just smile. ALso, renting a car and checking into a hotel as Heather has never been a problem. When flying for business, I like to stay over and have a Heather play day in a new city. Ah, life is good.

Heather, I agree enthusiastically. Staying for a play day is also part of my personal customs for successful travel. A good reason to travel, among several, is to enjoy the destination. I either show up two days early or stay two days beyond the purpose for the travel at hand. Drab or femme, my goal is to have a little fun. Staying two days beyond is better for places that are new to me because I will learn much about a place and what to enjoy there while first doing the business part of my travel. Two days is usually my limit before I must get back home and back to work.

My curiosity is killing me. How do you do it? There is usually little time between arriving at a gate and having an empty plane. The crew gets cranky with passengers who delay their quitting time. You must be quite a quick change artist. How do you deal with issues like makeup, shape wear, hosiery, etc?

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Originally Posted by abby054

My curiosity is killing me. How do you do it? There is usually little time between arriving at a gate and having an empty plane. The crew gets cranky with passengers who delay their quitting time. You must be quite a quick change artist. How do you deal with issues like makeup, shape wear, hosiery, etc?

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Hi Abbs. Well, the simple answer is timing has never been a problem. Planes are usually full which allows me about 20 minutes to change into Heather mode. I don't wear makeup or shape wear and on the rare flights that are sparsely populated, I can change during flight and sit in an empty row until landing. Cramped quarters and keeping my things off the dirty floor are challenging but timing is not an issue.

Started wearing my mother’s tights ( called leggings today), when I was 11 or 12. That was back in the mid 60?s when, as another poster pointed out, societal attitudes were much more restrictive. My mother knew and actually let me wear her tights for a while until she put the kibosh on it. I told my present wife (no cd was not the cause of my divorce) on our second date. She is ok, but does not want me to go too far. She is ok with me dressing but does not want to participate. Luckily I?m rather small for a guy, 5ft 6 135-140 so I can almost pull it off. My children in no way, shape or form would accept my crossdressing. I am very careful about getting caught and always carry a change of clothes and other sundries in my car.

I had been in the habit of wearing at least silk panties, vanity fair full cut are my favorite, under my male work clothes for a few years. I started wearing lace top thigh highs with them. Loved the feeling, I started bringing full sets of my feminine attire to work in a bag & get dressed in the bathroom stall.
I started finding it therapeutic for my day to go into the stall. Strip completely then get dressed, I loved the task of pantyhose first, then panties, then a slip, then skirt, blouse, heels. I?d sit there & stand up, I?d spend about 10 minutes dressed up then remove everything but leave the panties usually.
One day, in a more out of the way bathroom in the large office a guy walked in just as I put on the black pumps. On this day I had put on thigh highs over the pantyhose & had 2 slips, one half & a full.
?? he paused in front of my stall. I realized he could see my feet & legs!! Then I realized he could see in the crack??

I haven't been caught en femme but my GF found my stash of bras and panties and threw it out. Totally pissed me off. At first she assumed that I had kept trophies from previous relationships (which some were) but then gravitated to accusing me of some fetish that was subverting our relationship. I've gotten much more crafty in my hiding places since replacing some of the clothing. Unfortunately those "trophies" are gone. But not the memories that created them!