Although none of my family members besides my wife knows the extent of my cross-dressing I have actually been caught twice by relatives.
The first time was when I was 14. I had 2 sisters that were older and the oldest one liked to dress fairly trendy at the time. I had been regularly trying on her blouses and miniskirts for some time and I fit very well in my mom’s high heels. Any chance I got, I would put on various dresses and outfits. Usually, this would be when everyone was out of the house for ball games or when I stayed home from school pretending to be sick. I always got away with it, seeming to have a sixth sense as to when everyone would be coming home, and frequently got everything put away seconds before family members arrived home. I was starting to get more and more bold.
One evening I was home with only the one older sister. I was doing my homework at the kitchen table and she was in the basement doing hers. I figured she’d be down there for about a half hour at least and my super-powers would notify me if she was coming up stairs. I silently went upstairs, into her room and pulled out the black silk panties and bra. I knew right where she kept them. And I put them on. I put on some tan panty hose, a black and white blouse, and a black miniskirt that were my favorite outfit. I then went into my mom’s room and got her black high heels and put them on as well and went back into my sister’s room to look in her full length mirror. Just then I heard her open the basement door and start walking up the stairs. I was trapped! I prayed she would go into the bathroom and hid behind her door. When she entered her room and closed the door I gave a cheesy smile in a “ta-dah!” sort of way. I’m sure my face was beet red! She asked what I was doing and as I quickly undressed I said just goofing around. I was so flustered and embarrassed I took off all the clothes right in front of her getting completely naked so that I could contritely put everything back the way I found them.
I rushed back down to the kitchen table and tried to resume my homework but she sat next to me and wanted to talk. She asked if I was gay. She was very liberal and said it in a way that I knew she was saying that it was all right if I was. I said no. She asked if I had done it before and I lied and said I had not and that it was a spur of the moment idea. I made her promise not to tell anyone. She reluctantly agreed, again in a way that she seemed to imply that it wasn’t something to be ashamed of. But I was. The next few days I was walking on egg shells expecting the truth to come out but no one ever mentioned it. To this day she and I have never spoken about it again. I respect her very much for how she reacted and how she kept her promise.
I was also caught once by my daughter.
Only I didn’t know it at the time!
Once or twice a year my wife would go out of town for a few days with friends. Of course I would stay home to take care of the kids. And I would stay up as late as possible to dress and take photos. I would wait until I was sure the kids were asleep and start to transform. I have posted a few photos where there is a towel or robe at the bottom of the bedroom door to prevent light from seeping out or from wandering kids from peeking beneath it.
One such night I waited until about 11pm and started to get made up. I put on all of my makeup. Then I put on my panties, waist cincher, bra and my home-made play-dough breast forms. I put on nylons, and my blond wig. I put on a red dress that my wife had bought for me at a clearance sale (she liked it so much that she wore it a few times as well) and my red peep-toed pumps with 4 inch heels. As I put on the clip-on earrings, necklace and final touches I thought I was looking pretty good and was ready to take some photos. Then I realized I had left the tripod in the coat closet downstairs!
To get downstairs I would have to walk past the kids’ bedrooms and they usually slept with their doors partially open. I needed that tripod but could not bear to get all undressed and start all over. I decided to risk it. I turned off my bedroom light so that I would not be silhouetted with it shining behind me. Then I slipped out into the dark hallway. I crept downstairs, found the tripod and quickly returned to my bedroom. Completely undetected. Or so I thought.
Several weeks later we were all getting ready for church. I usually wear my soft soled black shoes but since I had chosen to wear a suit I put on the hard-soled dress shoes that I rarely wear. As I was walking down stairs to join my family my shoes made the clopping sound that high heels are known for making. Surprised at this, one of the kids remarked, “Whoa! I thought Dad was wearing high heels!” Quickly,(almost too quickly) my wife interjected, “That’s silly. Dad doesn’t wear high heels.” Then my daughter jumped in and declared, “Yes he does. I saw him wearing one of mom's dresses and high heels when she was out of town one night.” Luckily, this daughter is kind of a joker and everyone just laughed it off. She went on to describe how I was wearing a wig and went down stairs and back into the bedroom but by then no one was listening. Again, luckily, no one mentioned it again, even the one daughter. And there have been plenty of opportunities for her bring it up.
Years later after I had come out to my family I asked her about this incident and she said she had no recollection of it.
Although my wife knows all about my cross-dressing and my web page and online presence it wasn’t always that way.
My wife and I discuss my cross-dressing at times and we try to set boundaries that we are both comfortable with. I try to stay within those boundaries but a few times she has discovered that I’ve not always been successful.
A couple of times in the early days she had found photos or negatives that I was too careless to put safely away and they made for some very uncomfortable conversations. But the most memorable one was when I had returned from a backpacking trip and she had found my flicker and myspace pages.
She had known I had an online presence but it had been a few years since she had been curious enough to check it out. The last time she had seen my photos was in the beginning when I had the long dark brown wig and my makeup was really pale.
I came home and she greeted me warmly but there seemed to be something a little off. Then that evening when we had just gotten into bed she said she wanted to talk. My heart beat increased immediately. She said she couldn’t sleep while I was gone and decided to look up Heidi on-line. She said it didn’t take long to find me. Then she surprised me and said, “I was very impressed. You’ve come a long way. You look really good. ”
Holy crap! That wasn’t what I was expecting. She said she found the guys that comment on my photos rather creepy but she appreciates that I keep things pretty classy.
Then she said, “Um, about the lingerie photos…”
Uh-oh! Here it comes….
“I especially liked them and found that I was a little turned on by them.” Whoa!!!! “And I was wondering if I could meet Heidi some time.”
Holy Cow! I REALLY wasn’t expecting that.
Anyways, without giving too many details, we set a date for the encounter and she even got me new lingerie for the event. A red nighty with little black hearts and she suggested I wear the reddish wig. The encounter was enjoyable and a year or so later we had a more spontaneous encounter. But that’s been all. For the most part or love life is pretty darn good as husband and wife so the extra effort it takes for a fantasy encounter like that isn’t necessary. But the memories of those times are still special to me, not only because they were pretty erotic to me but also because I knew that she was trusting me and allowing herself to be involved in something that I appreciated so much.