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It Happened To A Friend Of Mine

This is a true story, but it's not about me. My mother may have suspected I had dressed up in her clothes, but she never caught me at it. Someone I know, a friend of mine shared a story with me about getting caught, and I would like to share it with you.

My friend Carrie is a crossdresser, and like so many of us, began experimenting with her mother's clothing at a fairly early age. Carrie was an only child and grew up living with her mother. There was no male presence in the home. Carrie's mother was a successful professional, made a very good living financially, and really dressed up to the nines. Because she had a good income, Carrie's mother had a lot a very nice, and rather expensive clothes.

Carrie grew up with around a very attractive mother who owned many designer suits, dresses, skirts, high heels, lingerie, etc. She was always dressed to the nines. Carrie's mom has gorgeous legs and always wore stockings or pantyhose, and sexy high heels. When Carrie was very young, she would often feel her mother's stockinged legs, and would put her head on her mother's lap while watching television. Carrie always seemed to appreciate her mom's clothes. As Carrie and her mom look back, the crossdressing was probably inevitable.

Carrie also found her mother to be gorgeous. I know that it's difficult enough to have a thing for wearing your mother's clothing, but then imagine being attracted to her as well.

When Carrie was 13, she waited until her mom had left the house for work. Carrie went ahead and put on one of her mom's finest skirt suits, along with a blouse, bra, panties, skip, garter belt, stockings and stiletto heels. And like so many crossdressers, once she got all dressed up, started to go about doing things around the house, enjoying the look and the feel of wearing women's fine clothing. She was playing piano, and didn't hear the door open.

Her mom was supposed to be at work, but for some reason, came home much earlier. Looking for her son, and hearing the piano, she walked into the living room. Low and behold, there was Carrie all dressed up, sitting there playing piano. The skirt was up around Carrie's waist, and her erection was exposed. Carrie's mom gasped. Carrie looked up and her heart nearly stopped. Before her mother could say anything, Carrie began crying.

I think this is every crossdressers biggest fear, being caught by mom or sis while wearing their clothes. As Carrie broke down, her mother quickly realized what was happening. Her son was a crossdresser, and she had caught her "in the act" so to speak.

Her mother's attitude immediately shifted from being shocked, to being motherly.

Carrie's mom knew that crossdressing was not that uncommon, and that Carrie needed someone who was understanding.

Carrie's mother sat down on the couch to comfort her son. As Carrie cried, her mother pulled her in closely, telling her that it was OK. Carrie held her mom tightly. Her mother has very nice sexy breasts, and Carrie's face was buried in her mother's blouse up against those lovely breasts. Carrie could also smell her mother's wonderful perfume, which made her smell so feminine. Carrie began to relax. She realized her mother was not going to go ballistic on her. Her mother held her, and rocked her back and forth, trying to comfort her.

But the feel of her mother's breasts against her face and the smell of the perfume also created a sense of arousal. Carrie's legs were brushing against her mother's stocking covered legs, creating a rather electrifying sensation for Carrie. As Carrie held on to her mom, her erection rubbed up against her mother's stockinged legs.

It was not intentional. It happened totally by accident. But all of the sensations were too much for Carrie. She became overly excited, and climaxed by ******* all over her mother's legs and skirt. This made her cry even more. Her mother knew how embarrassing this was for Carrie and just told her not to worry about it.

Carrie's mother gave Carrie complete access to her wardrobe. Carrie could wear anything she wants.

All this happened years ago, and I no longer keep in contact with Carrie, but I always thought she was very lucky!
BizSuitStacy BizSuitStacy 46-50, T 18 Responses Dec 5, 2010

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Now would love to have had a mum like that!

She I'd very lucky. Wish I could put some white stuff on her stockings

Thanks for your comment.

yes carrie was a lucky girl my mom did go ballistic and i had to become more secretive

Sorry to hear that about your mom. One never really knows how a mom will react to this sort of thing.

Thank you, im trying to find a friend to teach me how to dress as a women without judging me i live in texas a hard place to finds friends who understands this i wount know the first thing about makeup or clothing i have stayed in the closet trying to find myself for a long time trying to be someone im not, im built like a man "big" but want to look pretty as a woman can this happen, thank you for your kindness

Thanks for your comment!

I wish i had a mother like her, my mother beat me and didnt speak to me even on her death bed, i do want to dress up again, at 50 years old.

I am so sorry to hear that. No mother should shutout her son, just because he enjoys dressing in women's clothing. You should dress up again if you want to.

What a toching, lovely story. And you wrote it in a wonderful way. Than-you for sharing it.

Thank you - very much appreciated!

Dearest Stacy, what a wonderfully positive story you've shared with us, even if it is second hand, I loved every bit of it! You now have me wondering just what my life might have turned out to be had my Mom discovered my love and obsession with wearing her exquisitely feminine silky lingerie, nightgowns and dresses. I've shared more of this in my replies below so will not repeat here. After posting my replies and then re-reading your story, I'm now thinking that my Mom may very well have known of my feminine love of her things! This now helps me to better understand why she always wanted me to lay in her lap to watch TV after she'd changed into her satin long nightgown and robe! She eventually maneuvered my head so that I was nestled very nicely on her lovely breasts. This occurred for many years until she was diagnosed with breast cancer and had to have a double mastectomy after which it never happened again.

Oh hun...First off, let me say that I am so sorry to hear that your mother had to go through a double mastectomy for breast cancer. I realize this may have been long ago, but still, it is so difficult when a loved one has to go through something so traumatic.

Indeed, there is a good chance that your mother knew you liked wearing feminine things. I've talked to a few women on this subject, and they all repeat the same mantra, "mothers know these things." There is probably considerable truth in that statement. I suspect what varies is how mothers deal with the situation. Assuming my own mother knew...her course of action was not to say anything.

Thank you very much, BizSuitStacy, I truly appreciate your comments and thoughts. Berta

wonderful story ,my mother caught me only iin pantyhose but 40 years ago, iwas wearing he stockings and suspenders ,bra,camisole and her shoes also...what a lovely daysin my mom clothes

would you mind if I ask how your mother reacted when she caught you in pantyhose?

it was winter i said its very cold she said OK and next time for skiing she give me her pantyhose then usualy then i go to skiing i wear her pantyhose it was my own always the same but PH was 60 den the feeling of naylon on me was perfect ,winter is the bets time to star wearing pantyhose

This is the among the best stories i have read about crossdressing.<br />
so natural as u said this is true incident.<br />
but really touching.<br />
every ex<x>pression is so clear.<br />
thanks to you to get me a chance to be your reader for an extra natural story!

Thank you.

I remember that question when I was caught by my mom as well "are you gay do you like boys?"

I think that's a common "mom" response. In the future, I hope women growing up today will be more aware of and informed in the event they have a crossdressing son.

Thank you everyone who has commented on this story. And I'm thankful to so many other TVs and CDs who have told their story about "getting caught." This only re-emphasizes the fact that women experience a very wide range of reactions and emotions when they discover their son, their brother, their boyfriend, their husband, etc. is a tranvestite. <br />
<br />
We also have to understand that Carrie's mom very much enjoyed the look and feeling of women's clothing as well. And it's because of that fact, that Carrie's mom instantly realized if she loves how the clothes look AND feel, then why wouldn't her son, or any other male really. <br />
<br />
A woman on EP made a comment that really drives this point home. She said she loved being feminine. All of it, the clothes, lingerie, hair, makeup - everything about it. She talked about how much she loves the feeling of her clothes, and then said (I'm paraquoting) "I really don't understand why there aren't more transvestites." <br />
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I think we should look into her statement more. Thoughts?

Oh how I'd love to have a woman like that in my lengthy closeted CD'ing life! My wife wants no part of it and is barely tolerating finally. No hope that she'll ever help me go fully feminine. Guess I'll never know what Berta might look like. )&gt;: We definitely need to support her statement, do you have the link to it?

Sorry...I don't have the link.

What a wonderful, well written sotry. Thanks.

Thank you!

Oh My, what a very sweet story!!! And to have such a wonderful, caring Mother!!

She is a very caring, sweet and understanding woman.

Carry is lucky with his mom. Wish I have a similar mom.... She aways say: "I accept you, I accept you", but the last time, when I wisit her, I got the "You *****!" thing... She want to me to have a relationship with a woman, but when I luckily start one, she ruin it almost immediately...

I'm so sorry.

That is so sad! )&lt;:

My Mom caught me too. I was 27 and still living at home with my parents since I had a job but it didn't pay enough for me to move out. I went up to bed around 9:30pm and got all dolled up in black lingerie. (I have been crossdressing since I was 7). My Mom walked in on me and just smiled and let out a little giggle. I left the room and walked down the hall and went into my room. She didn't follow me and she never said a word about it!

That's a good experience.

@homerg2b: I have good reason to believe the entire story to be true, and that I didn't get "Carried" away with details. LOL! Granted, I was not there, and am simply repeating the story it was told to me. So take it for what it is.<br />
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@PHSensei: Indeed, Carrie is very fortunate. Her mother is a medical professional, and is very astute. She already had an understanding of transvestism, knew that it is not uncommon, knew that it wasn't some sort of deviant behavior, and was happy to let her son openly embrace this aspect of his/her femininity. <br />
<br />
Though I have lost contact with her, I'm sure Carrie is happy today.

Very touching story, Carrie was very lucky to.have her mom accept her dressing so quickly and realize what was going on. Sounds like part of carries fetish is wrapped up in the guilt and humiliation aspects of getting caught. And if it wasnt before that experience took her down that road somewhat. <br />
<br />
Hopefully Carrie has found a happy path for her life. I wish her well.

I think this story was "Carried" a little too far.

I disagree and think it was wonderful of "her" to share it with us. There are so many "anti" crossdressing comments on the web that reading a positive one is like a breath of fresh air! IMHO!!