My Most Embarrassing Crossdressing Moment

I was about 15, maybe 16, when Mom and Dad arrived home a "little early"... There was I, sunning myself in the (very private) backyard when I heard my Mom asking my Dad something. I was wearing a brown skirt and some heels that almost fit.

Yeah, it was an embarrassing moment.

I have a thick skin so any embarrassment rolls off me.I enjoy my time out and about and refuse to be fazed by anything.. Wish others would carry themselves this way and enjoy their girl time as I do.

My embarrassment occured at 21(I'm 35). I had decided to finally purchase my first femme outfit. I was still wearing my mother's clothing(which I started @ 14). I was still living at home while going to a local community college. I didn't have the courage to go to a store, so bought the clothes from a crossdressing store online. The clothes were shipped with no problem and were excuisite. I still remember the outfit. 2" black platforms with 4" stilleto heel, black fishnet hose(control top); a black, faux leather mini-skirt with a white w/various size black dots silk blouse. The blouse was button down, with a ribbon tie at the collar. I even bought a lacy black thong & bra combo. The only thing i did own was a wig from an old Halloween costume. Any ways, I wore that outfit everyday for about a week, until I made a huge mistake. I knew my mom was scheduled to be home for around 6. Unfortunately, I lost track of time and heard my mother scream. I turned around in my new outfit, including makeup, to see my mom standing in the doorway to my bedroom. I sat there stunned in silence until my mom walked away. After I changed, we had a long talk which led to me going to therapy. It helped for a time, but after a few months I found myself dressing up again, buying clothes from Walmart. To this day, my parents & family believe I ended that faze. If they only knew how many times I've been in thongs, hose and painted toe nails right under their noses.

Can't say I've ever been embarrassed, but a few moments I have had.
Once while at a job (I had come out to most of my friends by this time, but not to anyone on this job) I was sorting paperwork, standing over a table where a lot of people walking past behind me when I realized that my panties were showing around the top of my jeans. They were white with pink roses on them, so obviously female underwear. The next day I overheard some people talking and some laughing. It didn't really bother me, I was not at all embarrassed. I think some of them may have been though. lol But I truely think they were okay with it, no one ever said anything to me directly or treated me bad. I seriously think they were afraid to embarrass me or hurt my feelings. Thing is that I don't mind people cracking jokes if they are not intending to be hateful. I always let people know that it is okay to joke about crossdressing/transsexualism in my presence. I don't want them to feel like they are going to hurt my feelings. If they do not mean it in a bad way, I won't take it in a bad way. I rarely take offense when people want to joke a little. It's obvious when peolpe are joking to be hateful, but I don't encounter very much of that.

Anyway, As I have explained before in other posts, I woke up in the hospital after an accident with nothing but a shirt and panties on. I don't know at what point they had taken my jeans off or who all had seen me in my panties, but that's also how my parents found out that I like to dress female. I am still working on trying to tell them the rest of the story, that I want to have surgery, but so far, years later, no one has ever even brought up the panties I was wearing in the hospital. But I know it needs to be discussed soon.

One other time, I woke up to get dressed and walk to the corner Walgreens for my Sunday paper and a few other items. I picked up the jeans I was wearing the night before and was looking all over for my panties and could not find them. So, I just went ahead and got a fresh pair out and put them on and then my jeans and shirt and walked out the door and down the street. Went in the store, got my paper and other things I needed, paid for them and as I was walking out of the store, I looked down and saw my panties I was looking for laying on the sidewalk. They must have been down in the pantsleg of my jeans or something and fell out after a little walking, Anyway, I bent down to pick them up and stuffed them in my pocket and a guy was sitting in front of the store in a pickup truck watching me and I kind of got a funny feeling that he may have thought I was just some kind of pervert. lol Oh well, they were some of my most comfortable panties, so I wasn't going to leave them there.

My most embarasing moment was several years ago. I had been in the garageand had taken a fancy to one of my mothers bras. I decided to try it on. After taking off my t-shirt, I put it on. I couldn't believe how good it felt. Next, to fill it out, I used newspaper, not the most comfortable thing to use, but it was what was available. Just about that time, here comes Mom and caught me red handed. Of course, the questions started, mostly why. I tried to explain why, but just couldn't get a reasonable excuse out. After that conversation, the subject was dropped and didn't come out again for a long time. When the subjecy did come up again, I was several years older and I was coming out to her, which went well. So I guess that an embarasing moment turned into a good thing in the end.

I remember a number of very embarrassing situations that occured many years ago, when I first started cross dressing. At the time, I was fairly insecure about the whole thing and was always very conscious of what other people might think.

I specifically recall a time when I spent the whole morning dressing up as Paula and then headed out for some retail therapy. I'd only just entered the first shop when I saw a young guy point at me and tell his friend "That's a Man!". I just wanted the ground to swallow me up. I was so embarrassed that I turned around and headed straight back home.

Since then, I've become a much stronger person and incidents such as these no longer phase me. There'll always be someone that has something to say, but as long as it's not threatening or harmful, I just brush it off.

I used to purchase my clothing from Charity Shops but after one incident in a YWCA shop when the old girls behind the counter refused to sell me a dress saying " this is a nice dress far too good for a man to mess about with" (what magazines had they been reading?) I then started shopping at "Second Time Around " Dress Agencies, shops where the commercial acumen took over, they where keen to sell and cross sell with " have you got a nice slip to wear" and "a foundation corset would help you achieve a good figure" needless to say they just happened to have the required items in a drawer, thus boosting their sales and my satisfaction with the whole shopping experience. Needless to say I revisited those shops time and again, there was no pretence ( no little white lies to tell "er its for my girlfriend" or "its for a "Fancy Dress Party") the seller and the buyer both knew who the frock was for. In one city I lived three or four shops and eager assistants would "look after me with what I wanted and some things put to one side for me to look at" I was asked if I was Gay on several occasions ? my reply would be with my love of all things feminine and my devotion to women , why would you think I was Gay ! 1 in 4 men are supposed to be Gay, But in the Transvestite-Cross-dressing Community the average is 1 in 7 so girls with a TV-CD you are less likely to be dating a Gay man ! strange but true.!!!!!!! Be honest and careful !

I also have a thicker skin. I was not embarrassed per se getting caught a couple times wearing female attire. It was an annoyance mostly because I wasn't ready to come out.

My most embarrassing moment happened when I was 38 years old. I was home alone one day cleaning up the house. I was wearing a black micro mini skirt, panty hose, baby blue stockings above the knee, a baby blue top, and black high heel Mary Janes. Anyways I had a bag of trash and stepped out in the back yard and walked to the side of the house to toss the bag in the trash can, my backyard is pretty private. As I walked back to the house feeling very sexy I began to panic because I had the feeling that I lock the door! When I reached the door knob and tried to turn it, it was lock! I didn't know what to do, so I went to the side of the house and saw that the rest room window was open. It was kind of high so I placed a milk crate in front of the window and tried to heave myself through the window. I strained with all my might and finally was able to stick my head and shoulders through the window. My butt was now in clear view of any one walking or driving by my house. I started to crawl through and realized that my short skirt was not concealing anything. My stocking clad legs were dangling in the in the air. The vision I envisioned was my panty butt was fully exposed, and it was. Just as I started to go through the window I heard someone yell, "Hey baby you are looking fine". I went through the window and fell on the bathroom floor. They didn't see my face but my heart was racing a hundred miles an hour. My panty hose was torn and my baby blue stockings were ruined. That my friends was my most embarrasing moment.

Hello,

I am still shy about going out in public do to the fact I want someone to go with me so that I can feel very comfortable.

Thank you

Terri Virgil

I was caught in my older sisters clothes, panties, bra, slip, dress, and heels. She called me names, teased me about being a sissy, and told me she was going to tell our mother. I begged her and she didn't tell, but several weeks later, she took me into her room and made me dress up again. She put eyeliner and lipstick on me and combed my hair in a feminine style. Then she told me to wait a minute and left. I was admiring myself in the mirror when she walked through the door with our mom. "See, Daryn dresses up like a girl." she told my mom. I was in tears, but my mom just smiled and said. "Yes and he makes a very cute girl too." As she walked out she said "Play nice." My sister was mad that I didn't get in trouble and told me to get out of her things. Over the next few years until she graduated and moved out, she would occasionally make me dress up and do my makeup, and then tease me. I continued to dress in the things she left behind and moms things. I was never confronted by mom and she never mentioned my being "caught", but now my sis is very supporting of me and allows me to come to her apartment and dress. She has taught me a lot about being feminine and has even taken me out in public with her roommate girlfriend, (she's gay). We have gone out to bars a number of times and they tease me about hooking me up with a guy, or trying to get me to flirt. The rush is so exciting, but I really would prefer a woman like my sister as a lover/husband, rather than a man..............

Years ago, I was in my favourite restraunt, sitting at the bar, having a steak dinner. I heard a commotion behind me, but didnt look round, as that might call attention to me. Well anyway, about a half hour later the manager came over and apologised about the commotion. I said no problem, but what was going on? It seemed some macho dude said some wise crack to his girlfriend about me, and the manager caught the remark. He got into a commotion, and threw them out. I felt proud they would support me.

When I was about 10 years old I ordered some very sexy panties from mail order. Normally when they arrived I was home in the summer from school and got to the mail first, but this time my mother got there first. There were three very sexy panties in a black box. She embarressed me but than gave them to me anyway. I think she already knew as one time she refered to me as her special child.

Hello,
My most embarrassing moment was a few times for me, but the one that does stick out in my mind now would be the time I was catch going into the boys bath room when I was a boy.

I was ten years old and had to pee. Just when I was about to go into the boy's bath room to pee my teacher stopped me and told me that girls cannot go to the bath room in the boy's bath room.

My teacher marched me into the girls bath room to pee, then she marched me to the Princlipales office where I was punished for trying to use the boy's bath room. I would like to point out that this was in the 1960's and there was standared to follow.

I tried real hard to explan that I was a boy, but noone would even listen to me. i was told that I should never of lied saying that I was a boy when everyone could see that I was a girl.

I was even told that I must start wearing dresses and skirts, and not to wear any more pants. I told everyone there that I had no dresses and skirt. So the next day my teacher brought me some dressess and skirts to wear, and she made me change into a dress that very same day, and to take the rest home.

From the moment on I used the girls bath room to pee, and got away with it. Here is one thing even my classmates thought that I was a girl.

Here is one thing not even my parents knew that I was told about that and they did not know that I was even being passed as a girl in grade school.
Here is one thing I never took the dresses or skirts home.
The same year we where having a school play, and guess what, I was given a girls part in the play. It was the main or lead role I had to sing and kiss a boy.

Here is what my parents thaught about me play the role of a girl. They said that it was nice to see me play the lead in the school play. They did not say any thing. I found out late on in life that they thaught that it was normal for a boy to play the oppisete riole in a play and it was good that I had to learn how to be a girl, and it would not hurt me.

To this day none even knows that I like to cross-dress.

Love.

Terri