Over the last eight years I've been asked by various friends to house-sit for them a number of times. One co-worker wanted me to water her plants while she was on vacation, a female friend in grad school was going out of the country for a month over the summer and asked me to keep an eye on her place, and I dog-sat for a buddy of mine on a number of occassions.

For the most part I'm a pretty loyal friend, and people seem to find me trustworthy. And I am, except for one tiny detail.

Once left alone in any woman's house, I can't resist trying on her clothes, expecially her underwear.

And that's exactly what I've done each and every single time I've house-sat for anyone. As soon as I'm alone, I get undressed and spend literally hours going through closets, dresser drawers, laundry baskets, basically anything that might contain clothes for me to try on.

Of course, that's only half the story. I go through their wardrobes until I get myself all dressed up in their clothes, and then I masturbate.

I've done this over and over and never been caught, although I'm extremely careful about keeping things clean, folding things exactly right and always putting everything back exactly the way I found it.

I feel guilty afterwards, but mostly I'm just afraid of being caught. Every so often though the payoff is so good the whole thing seems worth it.

Like when I see my buddy's wife wearing a blouse or a skirt that I've worn, it drives me crazy.

Or the time I housesat for my grad school friend, I actually talked to her on the phone, from her place, dressed from head to toe in her clothes. That was amazing.

Another example, the co-worker whose house I watched a few summers ago, she had a fantastic collection of dresses and skirt-suits which were all roughly my size. I wore them all, and masturbated in most of them (usually wearing her hose and her pumps at the same time). Now, whenever she comes to work in something that I wore, it gets me super-excited.

Also, I just love to walk by her in the office and think to myself, we literally wear the same panties.

Comments

Anonymous

by Anonymous on Aug 12, 2007 at 11:17 PM

You've worn their clothes? Are they big women, or are you a small man?

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Anonymous

by Anonymous on Aug 13, 2007 at 2:32 AM

Get some help before its to late.

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Anonymous

by Anonymous on Aug 13, 2007 at 7:28 AM

I'm a pretty small guy. 5'6", about 135lbs. Even so, there are usually things I can't get into. My grad school friend was a really thin girl. I did try to put on a lovely pair of her capri pants, with a rear zipper, but it wasn't even close. Sometimes I have to settle for leaving something unbuttoned. I have pretty small feet for a guy though, so I can almost always try on their shoes.

Speaking of that, my favorite co-worker has a habit of leaving her shoes in the office at night. I've held off so far, but I'm really close to "borrowing" a pair overnight. After my experience at her house, I already know that we have EXACTLY the same shoe size.

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Anonymous

by Anonymous on Aug 13, 2007 at 7:48 AM

Do you have any suggestions?

I'm not going to try to defend myself, because I know that what I've done is a total violation of trust and is completely wrong. I should say though, that I've only done this about six times (by my best count). I never seek out opportunities and only do it when someone invites me to watch their place. I haven't done it in a while.

I know there's nothing anyone can do to stop me from wearing women's clothes. I don't even need to borrow other people's, by the way, I have a full wardrobe of female clothing all my own. I think I became de-sensitized to other people's privacy over the years. I used to sneak my mother's and my sister's clothes when I was younger (which is typical for young crossdressers) and I tried on my cousin's cheerleader uniform and a few of her outfits when we visited with my aunt and uncle during my teens.

After a while I got so used to going through other people's drawers, it just became easy. Plus, no matter how many skirts or pairs of pantyhose I have of my own (and I have lots) there's just such a thrill to wearing someone else's.

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Anonymous

by Anonymous on Aug 13, 2007 at 2:58 PM

A thrill or not (I have a friend's old cheerleader uniform too), it's still a violation of their privacy and it's going to get you into trouble. If you have to, stop agreeing to watch people's houses.

If it's really that much of a compulsion you may need to see some professional help. It's not the crossdressing itself, it's your need to rifle through their things.

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Anonymous

by Anonymous on Aug 13, 2007 at 4:41 PM

I know, you're absolutely right. It's been a while since I've watched anyone's house. Two of the friends whose trust I violated don't live near me anymore. I still see them, but not as much as I used to, and they live too far away for me to have an opportunity to do it to them again.

My one co-worker though still lives pretty close, and even though she hasn't asked me to mind her place for a while, I'm still tempted when I see her shoes in the office. So far, so good I suppose. I know it's wrong and I'm not acting on the desires.

I'm thinking about buying a similar pair of my own, maybe that'll help.

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Anonymous

by Anonymous on Aug 15, 2007 at 12:48 PM

I love how women leave shows under their desks. One woman in our sales department leaves a pair of black pumps under her desk. She wears them all day at work and switches to sneakers to go home. They're size 10 and fit my feet perfectly!!

I know what you mean about seeing her wear the stuff that you tried on.

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Anonymous

by Anonymous on Aug 21, 2007 at 9:00 PM

Ever heard of the nany-cam. One of these days, one of the owners will have a few of them installed and your ass will be caught.

I think you need to get laid.

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