I caught a crossdressing boy wearing his moms dress, makeup and heels?

[seanmuscle]

I knocked on my neighbors door to inform his wife that I returned some tools. But nobody answered so I helped myself in and saw this beautiful lady in an evening gown, stockings, black stiletto heels and wearing deep red lipstick. I asked her if her and the husband were going out. She said yes and to just leave the tools on the table. However, she looked all shocked and was stuttering so I looked closer and realized it was the mothers son. I am guessing the kid must have been 14-15 years old but quite small in stature so the resemblance caught me off guard. I told him he looked just like his mom and he was all blushing. Was kind awkward so I just left.

Anyways should I tell his mother? What would you do in this situation?

[JohnH]

No, don't embarrass the son by telling his mother. I would simply say," I won't tell anybody and you really look great!" If you were in his heels you sure would not want the neighbor to tattle on you!

[Added section]
I also agree with the other members that you never should have barged in.

[Shelly Preston]

Say nothing, the kid was obviously not expecting company

Act as if it never happpened

If he mentions it just let him know you wont go telling anyone

[linnea]

Unless he was robbing the place, stealing from his mom's purse, or doing some illegal act, I would not say a word. At that age, I would have been totally shaken by having a neighbor discover me en femme. What would be the point of telling his parents? I can't think of one that isn't mean-spirited.

[dilane]

Another good reason not to let yourself into someone else's house (unless you think there's an emergency).

I'd tell the kid that you won't tell anyone -- he's going to be worrying about it something fierce, if he's anything like I was at his age!

-- Diane

[Michelle 51]

You did the right thing.Just leave it lay and forget you seen everything.Due to his age the last place you need to be is anywhere around him.Thats the society we live in.When he's an adult in a few years maybe then you can talk about it with him and laugh over a beer.

[JohnH]

I'd tell the kid that you won't tell anyone -- he's going to be worrying about it something fierce, if he's anything like I was at his age!

-- Diane

Exactly. Don't leave the young man worrying if you will tell his parents!

[JulieC]

...But nobody answered so I helped myself in ... What would you do in this situation?

I wouldn't have let myself in.

If you were crossdressed at home, and didn't want to answer the door, wouldn't you be right angry that someone let themselves in because you didn't answer the door?!?!?!?

[sterling12]

YOU should have never entered that House. You didn't have permission!

But, you did, and so now you have done harm. Don't confront The Child about how your not going to tell her Mother. Probably The Last Thing She Wants is to talk with you. Right now she's very worried, frightened, and if she's been reading TG "Literature," she probably thinks you will want something from her!

Somehow, leave her A Discreet Note and tell her that "This IS The End of IT!" You won't be talking to anyone, nor will you be bothering her unless she wants to talk....in A Public Place!. Remember, it's a Fourteen Year Old. Anything you might do at this point can be easily misunderstood! I hope you understand that this whole situation could have bad consequences.

Peace and Love, Joanie

PS. If this is some "Fantasy" that you thought would be fun to run on here, shame on you! You have at least raised an important point, and maybe somebody else will learn from it, but I have a lot of doubts about this Story.

[Karen564]

I wont say what you did by letting yourself in was right or wrong...because regardless, I'm sure you meant well...since years ago, this was a common thing to do before we had to lock our doors..not to keep neighbors out, just the criminals..

But please do not let that young man hanging wondering what you will or will not do...If your not going to tell his mother or anyone else about it (which I would highly suggest you keep this to yourself for the boys sake) Then go over their & tell him as such so he can start breathing again...Beleive it or not, you may be saving a life by doing this for him & saving a mother from losing a child...many before him have taken their own lives in similar situations because of the shame of being discovered.....others may not, but some do...so lets play it safe...

Good Blessings ...
Karen

[Jenny Gurl]

I don't know how well you know the boy, but I would either tell him in private, or give him a note. I would apologize for coming in on him. I would set his mind at ease by saying you would not tell anyone and his secret was safe with you. Maybe tell him you had a friend who crossdressed for years and you thought nothing of it and that it will never be brought up again. You should make this apology while dressed to the nines in full makeup and forms. Ok, just kidding about you dressing for the apology. You definitely need to set his mind at ease so he is not worried sick and if he wanted anyone including his mother to know, he would tell them.

[PetiteDuality]

Somehow, leave her A Discreet Note and tell her that "This IS The End of IT!" You won't be talking to anyone, nor will you be bothering her unless she wants to talk....in A Public Place!. Remember, it's a Fourteen Year Old. Anything you might do at this point can be easily misunderstood! I hope you understand that this whole situation could have bad consequences.

If I were the kid and I receive a note saying "This IS the end of it" I would shit my pants. It sounds like a death treat or something!. Please don't do that...

[Rhonda Jean]

I don't believe this. I've been the 14 year old crossdresser, and if someone had come to the door I would have been hidden so far in the back of the house that a German Shepherd couldn't find me.

If it is true, you've got a lot of nerve "helping yourself in" to your neighbor's house. Tell on the kid? You better hope the kid doesn't tell on you! What's worse, a kid dressing up or a person entering someone's house when they're not there.

[KellyCD]

FAKE.

Idk, this just seems like BS to me.

[Ozark]

I guess it depends on what part of the country you live in.
I was sitting on our screened in back porch, dressed in VF lace noevau panties, VF pajamas and matching robe, sipping a nice vodka martini watching television.

I had showered and put cetaphil moisturizing cream on and I felt wonderful!

I looked up and the neighbor's daughter and her live in walking up the driveway and looking in at me.

They waved and said, "Hi Ozark"

I turned off the tv and the porch went dark.

Then I hollered back at them, "Hey, I sure do like my martinis!"

They laughed and never a word was said.

But now, they always announce their presence as they come up the driveway.

My wife is supportive of me, but she doesn't like me to stay in my nightclothes in the morning, so I always put on sweats to go out and get the paper.

[Nicole Erin]

An Erin agrees -
Let him know you are not gonna say a thing, and of course don't go spreading anything around, I mean stuff like this, for someone young, it usually a fiercely guarded secret. Unlike those of us who are older and can handle things, he probably thinks he is the only one in the world.

[JohnH]

I guess it depends on what part of the country you live in.
I was sitting on our screened in back porch, dressed in VF lace noevau panties, VF pajamas and matching robe, sipping a nice vodka martini watching television.

I had showered and put cetaphil moisturizing cream on and I felt wonderful!

I looked up and the neighbor's daughter and her live in walking up the driveway and looking in at me.

They waved and said, "Hi Ozark"

I turned off the tv and the porch went dark.

Then I hollered back at them, "Hey, I sure do like my martinis!"

They laughed and never a word was said.

But now, they always announce their presence as they come up the driveway.

My wife is supportive of me, but she doesn't like me to stay in my nightclothes in the morning, so I always put on sweats to go out and get the paper.

I put the trash can to the alley while I'm wearing a nightgown. Sometimes my wife, wearing pants, and I, wearing a dress, go for walks in the evening. So I don't keep anything a secret!

[Cassandra Lynn]

Just for the record folks, there are some ppl, in some places around this country that have developed a close enough bond with their neighbors, that
it is ok to enter their home, for instances like this. That said, it seems the OP would have had some prior knowledge of a teen living there
and possibly being alone in the house. Curious, indeed.
As to what to do in such a situation? When it's safe and appropriate, let the youngster know nothing will be said, and leave it at that. Like it was mentioned,
todays teens are a little different, telling her about yourself and your thoughts on CDing would just be too much.
mj (Cassie)

[girlygirl152]

I certaintly wouldn't tell his parents. I think we all know its a sensitive subject for those who are closeted

[CatAttack]

Well think of it this way. If that happened to you when you were 14-15, would you want the guy that caught you to tell your parents?!

[jjjjohanne]

Sounds fake.

[Gina X]

Sounds fake to me too, there are too many loose ends.

Love Gina x

[suspender]

Its a bit of a rhetorical question. Deja vu comes to mind, as most of us have probably been in the boy's shoes (stilettos whatever) sometime in our life, so why would you want to out him to anybody? Depending on the authenticity of the recount (remarkable detail included), the poor kid would want to be invisible for a while if he didnt already slip through the cracks in the floor! Best to say nothing to no-one, including the kid, unless he raises it with you. Just greet him in passing as you always have. He knows you know, so just saying hello as usual and letting it pass may be best at this time. This will assist his confidence and let him get on with his life without stressing on what the handyman neighbor will do next.

[Sara Jessica]

It's always fun when other's bs meters go off before I see the thread. Tells me mine is still working just fine.

[nvlady]

When I was fourteen, I was the only one in the world that wanted to wear his mothers clothes.
Had I gotten caught I think it would have helped to hear "I won't tell anyone about it because I wouldn't have anyone to know about me when I was your age".