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- When I Was A Kid -

When I was six I was sitting on a swing at my cousin's house.My cousin and some of her friends had been playing jump rope when one of her friends came over pushing her new baby sister in a carriage.The girls gathered around and cooed over the baby for a while then the girl took the baby home.A few minutes later I noticed my cousin staring at me.Then she came over with an evil smile and told me she was going to dress me up like a baby.I called her crazy but she grabbed my arms and started dragging me along with her.One of her friends who was a lot bigger than her came to join her.The next thing I knew we were on the back porch,I was in my underwear,and they were holding me down.They put a cloth diaper on over my underpants,a frilly bonnet on my head and used the jump rope to tie me in an old stroller.They took me out front and played house with a couple of other girls.

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# 4273 - by Anonymous / February 24, 2009
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Anonymous

by Anonymous on Feb 28, 2009 at 3:34 AM

So what else happened? Did anyone see you dressed up like a baby besides the girls?

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Anonymous

by Anonymous on Mar 6, 2009 at 6:22 AM

Some neighborhood girls paid me twenty dollars to let them dress me up in a ballerina outfit when I was in third grade.Easy money I thought until they dragged me outside.

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Anonymous

by Anonymous on Mar 13, 2009 at 7:09 AM

LOL Anymore details?

One time I told my friend I'd pay him to change clothes with me for a few minutes, just to see what he'd look like. We were at another friend's house and changed in her basement. I didn't have any money and we walked to the store leaving him there in my skirt and blouse!
He was so gullible! LOL

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Anonymous

by Anonymous on Mar 13, 2009 at 2:11 PM

My cousin put me in that same situation, only she didn't offer to pay me. We were playing a boardgame at her house and she was fussing with her dress while sitting on the floor. I said something to which she suggested that we switch clothes to see what it felt like. I agreed, but just for a few minutes.

My aunt came in while we were back at the game but with me in the dress. She thought it was funny and I had to spend the rest of the day like that. My cousin kept trying to sneak peeks at my underwear to make me uncomfortable - and I hadn't been doing that to her!

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Anonymous

by Anonymous on Mar 14, 2009 at 2:47 AM

Sure you hadn't been doing that to her. =p

Hadn't she already seen you in your underwear when the two of you were changing clothes?

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Anonymous

by Anonymous on Mar 14, 2009 at 4:26 AM

Yeah, I probably was trying to peek. Maybe that's why I didn't object later when she decided I needed more than just the embarrassment of being in the dress.

She did see me in just my underwear when i took the clothes off, but then she took them into another room to change and brought her clothes out. So I never did get to see her in just her underwear.

My aunt had asked if we also swapped underwear. We said we hadn't, which she thought was smart (for hygenic reasons) but thought I might look cute in a pair of panties which she offered to get if I wanted them. They both laughed and I said nothing.

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Anonymous

by Anonymous on Mar 15, 2009 at 5:10 PM

Yeah,I made my guy friend strip down and give me his clothes.Then I went behind some stacks of boxes to change so he never saw me in my underwear either.I helped him into my skirt and blouse and then presented him to the other girl.He demanded his money after we teased and laughed at him.That's when I decided to walk with her to the store and leave him stranded in my clothes. LOL

We were in sixth grade and I got him into a white blouse and floral print ruffled skirt.

So how old were you and your cousin, and what did the dress look like?

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Anonymous

by Anonymous on Mar 16, 2009 at 12:22 PM

I was twelve and think my cousin was thirteen. This happened in the mid 70s when girls wore dresses and skirts most of the time and the designers tried hard to make dresses look like something else. This dress was supposed to look like you were wearing a blouse and skirt with a sweater vest over the top. It zipped up the back and had a single button at the top. She watched me try to zip it up first, then came around behind me and did the zipper before buttoning the button. I asked her how you get out of the thing once it's been zipped and fastened and she said you don't.

The skirt was pretty short as I recall - about halfway down the thigh although it seemed much shorter than that at the time. How long was the skirt you put him in? Did it have any fasteners you'd have to be a magician to get out of?

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Anonymous

by Anonymous on Mar 17, 2009 at 3:15 AM

"How long was the skirt you put him in? Did it have any fasteners you'd have to be a magician to get out of?"

The skirt was mid-thigh length and it just had an elastic waist, so he didn't need to be a magician to take it off. But he would have still had to wait on us to get back from the store or walk home in his underwear. He was trapped either way.

I do like the idea of the zipper and button on your dress though. I bet the look on your face was priceless when you asked how to get out of it and she said you don't. LOL

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Anonymous

by Anonymous on Mar 17, 2009 at 12:54 PM

I know that women's clothes were originally designed to have someone help the women in and out of them, but what a stupid concept! Putting a zipper that ends up where you can't reach it and then putting a button over the top of that. Dumb.

Yes, I guess I must have looked pretty scared when I realized that I had to wait until she let me out of the dress. Or her mother. It really was up to her what happened and how many people saw me dressed like that. I probably could have torn the dress off, but then I would have been in trouble for trashing her dress and she was still wearing my clothes.

After we sat and played games for a while it was time to switch back. Her mother had already made the joke about getting me some pretty panties and then my cousin got annoyed that I had wrinkled her dress with all the fidgeting and trying to keep her from peeping up the skirt. So after she undid the zipper and let me out of it, I still had to take a spanking before she'd give me back my clothes.

Is this something all girls think is funny? Did you either dress up another boy or try to? What would you have done as extra punishment if he wrinkled your skirt or spilled something on it? I'll guess that you're younger and grew up at a time when spanking wasn't as common. Still, wouldn't pulling up your friend's skirt and smacking his bottom make you feel good and him more embarrassed?

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Anonymous

by Anonymous on Mar 17, 2009 at 12:54 PM

I know that women's clothes were originally designed to have someone help the women in and out of them, but what a stupid concept! Putting a zipper that ends up where you can't reach it and then putting a button over the top of that. Dumb.

Yes, I guess I must have looked pretty scared when I realized that I had to wait until she let me out of the dress. Or her mother. It really was up to her what happened and how many people saw me dressed like that. I probably could have torn the dress off, but then I would have been in trouble for trashing her dress and she was still wearing my clothes.

After we sat and played games for a while it was time to switch back. Her mother had already made the joke about getting me some pretty panties and then my cousin got annoyed that I had wrinkled her dress with all the fidgeting and trying to keep her from peeping up the skirt. So after she undid the zipper and let me out of it, I still had to take a spanking before she'd give me back my clothes.

Is this something all girls think is funny? Did you either dress up another boy or try to? What would you have done as extra punishment if he wrinkled your skirt or spilled something on it? I'll guess that you're younger and grew up at a time when spanking wasn't as common. Still, wouldn't pulling up your friend's skirt and smacking his bottom make you feel good and him more embarrassed?

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Anonymous

by Anonymous on Mar 17, 2009 at 6:34 PM

Pulling his skirt up definitely made him more embarrassed and I liked that. I never tried spanking him. When we got back from the store he was still in the basement and we teased him a lot about how good he looked. I told him that I looked better in his clothes and that we shouldn't switch back. I did give in in the end.

I can't say that all girls think it's funny. But I think most find it funny to see a guy in a dress or skirt... especially if they are the ones that get the guy into them.

I tried to get some other guys to let me dress them up for Halloween and pep rally skits, but they wouldn't do it.

The only other time I dressed a boy up was a few years before this incident. I think I was 9 and the boy was 8 or 9. He was my cousin's neighbor, and a pain in the butt. Somehow he got his head stuck between the metal banister of my aunt's porch steps. My cousin and I squirted him with squirt guns and,come to think of it,she spanked him. When we figured out he was really stuck... and at our mercy, we took his shorts off and put one of her dresses on him.

We both got grounded and had to apologize to him and his mother. It was worth it though! LOL

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Anonymous

by Anonymous on Mar 17, 2009 at 7:40 PM

When he got his head stuck in the bannister you should have rubbed your ass in his face.

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Anonymous

by Anonymous on Mar 18, 2009 at 2:47 PM

When did you pull up his skirt? When you first left him or when you came back?

My cousin lived in the same town I did and we had lots of friends in common even though we went to different schools. She only told a few people about what happened but a lot of kids ended up finding out. A few years later in high school I had a girlfriend who thought it would be fun to go out for halloween as a boy scount and girl scout. I, of course, was the girl scout at her suggestion. She found a uniform from somewhere with a white blouse, green skirt, sash, hat and ankle socks with the little logo on them. He brother loaned her his scout uniform. That wasn't nearly as bad as the whole dress incident with my cousin because it was halloween, this girl was my girlfriend and it was all somehow more dignified.

Naturally my cousin heard how I was going out dressed and had to come over to see. She told my girlfriend that if I did anything rude or damaged the uniform that she'd come over and spank me like she had done before. That was pretty awful and my girlfriend thought that might make a cute picture - a boy scout spanking a girl scout.

Boys will do pretty much anything for a pretty girl they like, so if you're still of that age, don't give up on the idea if you're still interested. We don't agree to it unless we think there's something about the experience that might be fun. Personal attention from a pretty girl is always a good thing.

Your cousin's neighbor must have done something weird to get his head stuck like that. I'll bet he looked rather silly with his head stuck in the railing, sporting a dress and a freshly spanked bottom.

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Anonymous

by Anonymous on Mar 18, 2009 at 6:38 PM

I'm not sure how he got his head stuck in there. He did look so silly stuck that way wearing her dress. It was a real frilly peach colored one. His mother heard him yelling and came and got him free.

A boy scout and girl scout, with the roles reversed, I love it! I've always liked the idea of doing something like that for Halloween. Maybe a cowboy and saloon girl or a magician and assistant.

Did you carry a box of cookies with you? =p

Almost forgot. When I presented him to my friend she was giggling and he was of course embarrassed. He just stood there looking sheepish with his hands at his sides. I was behind him, so I yanked the skirt up. He couldn't pull it back down fast enough and we both howled with laughter!

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Anonymous

by Anonymous on Mar 18, 2009 at 7:29 PM

Did you guys at least leave the dress down over his underwear or leave it pulled up? It seems like you might have kept it up at his waist at least for a little while.

We only went out that one Halloween together. Before she settled on the scout theme she wanted to try a few others including a football player and cheerleader. I think she had trouble tracking down a football uniform for herself. She seemed rather pleased with herself for how well the skirt and sweater fit me. By the time she finished adjusting the skirt and making sure the briefs were on just right, they were getting a bit snug, which she thought was hysterical.

Anyway, no one had a box of cookies handy. My cousin did walk around with us for part of the evening. She'd occasionally ask people if they wanted a girl scout cookie, then say I didn't have any but I did have buns - and then she'd flip my skirt up. I pulled it down pretty fast too.

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Anonymous

by Anonymous on Mar 19, 2009 at 9:46 AM

The dress was quite short on him so there wasn't any reason to leave it pulled up. Besides, with him stuck like that it took a little while, and effort, to get the dress on him. He was exposed in his underwear for several minutes.

It sounds like your girlfriend was really into dressing you up as she put lots of thought into it. Your cousin must have loved embarrassing you because she took every advantage to do it.

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Anonymous

by Anonymous on Mar 19, 2009 at 4:19 PM

I'd imagine that this boy steered clear of you after that incident. I guess it could have been worse and you could have left him naked, or put him in panties, or put on hair ribbons or something.

My girlfriend and I weren't together all that long and once you get old enough anyway, you don't dress up and go out for Halloween. There was only one other occasion (the next Halloween) where we went to a party together in costume together. She didn't really suggest dressing me up very often. My cousin was much more into that than my girlfriend after the first time at her house. I tried to avoid spending time with her unless there was a lot of family around, but she did manage to get me into a dress or skirt a few more times before I finished high school and moved on to college.

You know how boys are about girls - we like to show off and do weird stuff to get attention from them. That's why kids in our class would jump off swings, drop off the monkey bars and land on their heads and do other dumb stuff. We like girls to notice us because when we're kids we're too shy to talk to them. My cousin wasn't exactly ugly and even though we're related, it's always good to get attention from a pretty girl. If you let a girl dress you up in something ridiculous you're still getting her attention and unless it's just to be mean, it's also an indication that the girl likes you. Isn't it?

When you bothered to torment the boy with his head stuck, didn't you like him at least a little bit but you wouldn't have told him? The first boy you dressed was a friend and you two obviously trusted each other. I'll bet you liked him at least a little too.

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Anonymous

by Anonymous on Mar 20, 2009 at 6:20 AM

Actually the first time was the boy with his head caught in the banister, and no I really did not like him. He was just a pain whenever I was at my cousin's and he pestered her all the time. It was just fun to get to torment him for a change.

My cousin and I were 9 and 8 at the time so we didn't have make up to put on him. Hair ribbons would have been a nice touch but he could have just pulled those out. I knew we were going to get in trouble but if we stripped him naked it would be much worse. The thought to put the dress on him came when I remembered my cousin and I had to wear those awful peach colored things to another aunt's wedding the year before, and he had laughed and made fun of us.
You're right about one thing though, he steered clear of us after that!

I did like the boy that I tricked into changing clothes with me. He must have trusted me, poor guy. =p
It was a mean trick but he didn't stay mad for long. My friend and I were the only ones who saw him and we didn't tell everyone. We just teased him between us. Besides, I only left him stranded for a little while and the look on his face was priceless! LOL

So what is the deal with your cousin and these other dress up incidents?

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Anonymous

by Anonymous on Mar 20, 2009 at 8:50 AM

Yes, revenge does seem like a good motivation but if you really just hated him you wouldn't have wasted the time on him.

I didn't have a sister growing up and my cousin and I were like brother and sister. After the first time which was completely unplanned, she decided she liked it. It was uncomfortable for me but not so much that I wanted to take away her fun. The other incidents were harmless things like helping her hem a dress she made.

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Anonymous

by Anonymous on Mar 20, 2009 at 9:35 AM

I didn't say that I hated that boy, just that I didn't like him. Anyway that incident put a stop to his pestering, so I never wasted my time on him again.

Your cousin sounds like she just had a thing for seeing boys in dresses. I guess you were a good sport playing dress-maker dummy and such.

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Anonymous

by Anonymous on Mar 20, 2009 at 9:38 AM

My cousin is VP of a decent sized company now, so perhaps she just likes being in control. I thought I was being a good sport.

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Anonymous

by Anonymous on Mar 20, 2009 at 3:29 PM

It sounds like your cousin is good at being in control since she's made VP of a company. Good for her. :)

When you see her, does she ever bring up those times of dressing you up and teasing you?

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Anonymous

by Anonymous on Mar 20, 2009 at 4:52 PM

Not so much any more. It was a long time ago. The last time it came up was when her parents moved from the house and they had to pack everything. She found the dress in a box of old clothes. There were also some old faded polaroids from Halloween and such that she hung onto. She called me that night to catch up, talk about the packing and to share her finds.

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Anonymous

by Anonymous on Mar 22, 2009 at 7:42 PM

Cool. I wish I had pics of the boy I conned into switching with me.
Oh well, Halloween is coming up. Maybe i can talk my boyfriend into something. =p

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Anonymous

by Anonymous on Mar 23, 2009 at 6:45 AM

Make it sound like fun and he might go for it. Offer to do something in return that he likes and you don't normally do - go fishing or hiking or something.

Let me know what happens!

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Anonymous

by Anonymous on Mar 25, 2009 at 1:55 PM

I casually mentioned to him yesterday that Halloween is coming up. I asked him what he thought about going as a magician and his assistant. He enthusiastically asked,"Do you mean like with the skimpy little costume and high heels?"
I told him yeah, but he'd have to shave his legs. He just scowled and said,"Very funny."
So, we'll see. I'll keep your suggestion in mind.

If anything happens I think I will start a new thread, maybe in the anything goes section.

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Anonymous

by Anonymous on Mar 27, 2009 at 3:15 PM

That sounds like a good choice. I'm sure you can talk him into it. Get yourself a hat and a stuffed rabbit too!

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Anonymous

by Anonymous on Mar 29, 2009 at 8:52 PM

He said he'd rather dress as a rabbit and let me pull him out of my hat. LOL
When I first mentioned it to him he got excited because he thought I was going to be the assistant in the skimpy outfit.

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Anonymous

by Anonymous on Mar 30, 2009 at 7:50 AM

It might help if you offer to wear the outfit afterwards. If the outfit turns him on as much as the idea of him wearing it does to you, then you both win.

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Anonymous

by Anonymous on Apr 1, 2009 at 8:16 PM

I'm thinking of dressing as a sheep, if I can get him to go as Little Bo Peep!

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Anonymous

by Anonymous on Apr 2, 2009 at 6:15 AM

Considering that Bo Peep is probably dressed from head to toe with leggings and a longer skirt, that's more likely to fly. It might help his comfort level that you'll look pretty silly and he'll be mostly covered up (even though there's a dress involved).

Good suggestion. You can save the magician/assistant for next year.

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Anonymous

by Anonymous on Apr 2, 2009 at 10:44 AM

What kind of underpants was he wearing and why didn't you take his underpants off? You could have seen his bum hole.

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Anonymous

by Anonymous on Apr 3, 2009 at 7:28 PM

I didn't want to see his bum hole, and didn't take his underpants off for other reasons. I knew we'd really get into trouble if I'd done that and I wanted to embarrass him not scar him for life!
He had on white briefs, he was like 8 or 9.

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Anonymous

by Anonymous on Apr 4, 2009 at 3:43 PM

I would like to see your bum hole and if you let me see your bum hole I will kiss it and lick it.

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Anonymous

by Anonymous on Apr 7, 2009 at 5:04 PM

Oh, if I can convince him to go through with it and find a costume to fit him, he's going to look pretty silly himself.=p
I'm thinking a pastel pink ruffled dress, petticoat, pantaloons, white lacy socks & mary janes, a blonde curly baby doll wig & bonnet.
My sheep outfit will be real cute!

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Anonymous

by Anonymous on Apr 7, 2009 at 9:32 PM

Did you ever see his bum hole or even his buttocks? I bet he had a cute bum.

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Anonymous

by Anonymous on Apr 8, 2009 at 4:42 AM

It will help if you look even sillier than he does. Good luck and please keep us posted!

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Anonymous

by Anonymous on Apr 8, 2009 at 11:27 AM

Make him kiss your ass wearing nothing but your panties.

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Anonymous

by Anonymous on Apr 15, 2009 at 7:18 PM

He's going to be Bo Peep! ;-)

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Anonymous

by Anonymous on Apr 17, 2009 at 6:05 AM

Very cool. I'm sure you guys are going to have a lot of fun. Will this be for a party? I'm assuming you're a little old to go out ringing bells for candy.

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Anonymous

by Anonymous on Apr 17, 2009 at 10:28 PM

Yes, a party some friends are having. He's going to be such a hit!

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Anonymous

by Anonymous on Apr 18, 2009 at 4:24 AM

If you find a way to post some pictures anonymously, we'd love to see them! Have fun with this. It should be awesome!

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Anonymous

by Anonymous on Apr 18, 2009 at 9:27 AM

The word awesome sucks.

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Anonymous

by Anonymous on Apr 19, 2009 at 5:30 AM

Jeepers Beav, why do you say that? I think 'awesome' is neat-o keen. It's the cat's pajamas!

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Anonymous

by Anonymous on May 8, 2009 at 8:30 AM

Sorry, I promised no pics on the internet. It was very funny, though. He looked so silly, and we had fun. Our friends couldn't believe he went through with it.

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