Did you ever put on women's clothes on the pretence you were just trying to be funny

[Robbiegirl]

To kind of introduce your S.O. to your kinky side ?

About 20 years ago.

I was not sure when I was going to tell my live in Girlfriend of 2 months but one morning, she was doing what she always does. Which was blow drying her hair in one of her lacy bikini Bra and Panty sets (maidenform) while facing the mirror. I noticed she had several similiar Maidenform sets on the bed since she had just folded them. Since she is a bit curvy and I am skinny Her Babyblue lacy French Cut Panties & bra fit fairly well and I made sure to try and not look excited. Anyway I walked in wearing the same lingerie as her and asked with a limp wrist if I could borrow her drier. when she looked at the mirror and saw we were wearing matching sets she fell over laughing ! I could not get her to stop for several minutes ! Anyway when she came to her senses she started chasing me around the house with nail polish in her hands ! After that nothing was too shocking even though at that point she wasn't sure what it all meant

[texasm31]

Not for that reason, but yes to be funny. The summer after graduating HS, four of us (2 guys and 2 girls) were skinny dipping at my friend's house. No one was dating. We were all friends, but if I recall correctly, it was one of those situations where there was chance that we would pair off for some activities at some point, but we had no idea how the pairing would end up. So anyway, we finish swimming and are planning to play some drinking games and one of the girls puts on my boxers and heads up to the table. So I of course decide to put on her undies. Perfect opportunity for me . Too bad for my taste, they were giant cotton granny panties. What 18 year old girl, even in the mid 80s, wears granny panties out for the night when there is chance that they will be getting naked that night??? But I wore them anyway. The girls thought it was hilarious. My friend was appalled and disgusted.

[Beverley Sims]

It happened often when I was younger because my girlfriends were impressed with how I could carry off the girl image so well.

[Richelle423]

Yes I did! One day when my girlfriend was sick and in a depressed mood I was folding laundry and she said I should put on her her dress I was folding so I did (I don't think she was expecting it) when I walked into the living room it made her smile and laugh and at the same time she took a picture of me with her cell phone! ( I did'nt expect that) Then she sent the pic to her best friend. I thought it would break the ice with my CD'ing I was wrong but she knows what I do when she's not home.

[Karren H]

No.... apparently I wasn't smart enough to think of that... sigh....

[Tracii G]

Fun yes to be funny no.

[Kate Simmons]

Nope, I was always dead serious when I got dressed. Now I have fun with it though.

[reb.femme]

Now I wear my clothing for the sense of well being I achieve.
Back in the day, I was hormone charged and did it, as Wldaboutheels would say, '..for the Os'. Fantastic!

Rebecca

[kimdl93]

Things happened the other way around in my case. I was deeply repressing my desire to CD when my first wife and I married. A few weeks or months into the marriage we were playing around in the bedroom. One of the little fantasies we enjoyed as the idea of her making it with one of her girlfriends - she suggested one, then asked me to put on her panties, bra and pantyhose. I didn't protest one bit, and we had a wonderful time. Thereafter, I often wore lingerie when we were in a playful mood, which in those days was rather often. She pretty quickly deduced that I had more than a casual interest in wearing women's things and for most of our long marriage, was very supportive.

Fast forward to second marriage. While we were still early in the relationship, but serious, I came out to my then GF, now second wife. She was surprisingly accepting and a few weeks later, we were playing around and she pulled out a pair of her thigh highs and started putting them on me. We haven't turned back since.

[Robbiegirl]

Kimdl93, thanks, but you have to pretend to protest a little, don't you ?

Oh I did forget to mention that I wrapped a towel around my hair to look a litle more girly in the bra and panty set !

[Michelle_CD]

I had a fwb staying with me a couple nights as she passed through town. We went for a walk around the neighborhood and when we got back she was feeling a little frisky. So she takes off her shirt and unhooks her bra. At that point I grab it and put it on. I didn't even hook it in back but she looks at me and says that is soooo wrong. I took it off right after that. Funny thing is was that I was wearing a pair of black microfiber panties and she didn't even notice when things went a little further.

[MatildaJ.]

What 18 year old girl, even in the mid 80s, wears granny panties out for the night when there is chance that they will be getting naked that night?

I turned 18 in 1988, and I didn't own any sexy panties until a guy bought me some. Eighteen-year-olds have limited cash and other priorities. In high school you learn that wearing plain cotton underwear is best for avoiding yeast infections, so I didn't see any reason to wear anything else. I'd feel a lot more frisky in bed without a yeast infection; that's all I knew. And when we fooled around, we either kept our clothes on or we got naked pretty quickly. Just sayin'

[Terraforming]

I did an event in high school and went out a couple times dressed up and acted like it was a joke. It ended up being a bit problematic in the long run, though. When I started coming out, most people were supportive, but the people who thought it was just a joke and were introduced to it that way were a bit freaked out.

[JUSTME]

Yep, pretty similar story to yours Robbiegirl. Good times until the camera came out. That was back when they still used film. I did not go and pick up that roll. We had some interesting times.

[texasm31]

I turned 18 in 1988, and I didn't own any sexy panties until a guy bought me some. Eighteen-year-olds have limited cash and other priorities. In high school you learn that wearing plain cotton underwear is best for avoiding yeast infections, so I didn't see any reason to wear anything else. I'd feel a lot more frisky in bed without a yeast infection; that's all I knew. And when we fooled around, we either kept our clothes on or we got naked pretty quickly. Just sayin'

Very close to the same age. I understand the benefits of cotton and most of my GFs wore cotton. Sexy panties were not quite the norm yet in 88. Sexy at that time was a string bikini, or maybe had a cute pattern but these were beyond plain. They were huge too, like bloomers. She was not a big girl, but these came up to my belly button.

[tiffanyjo89]

Very close to the same age. She was not a big girl, but these came up to my belly button.

Maybe she lived in a kinda tight house? I don't know. My sister liked to wear thongs when she was in high school (she still does, I think, I'm not sure) but she didn't get a lot of them like she wanted because we (my mom, sister, and me) lived with my grandma and if my grandma saw a thong in the laundry or in my sister's room, she would freak. (Imagine if she saw me wearing a thong...).

[Chickhe]

Tried it a few times years ago when we were first married and it was fun although we were both too insecure and uneducated on it to really talk openly about it. I CD on Halloween now just because I enjoy it and in a way its my way to rebel against conformity the other 364 days of the year and my wife seems to be really turned on by it. I think it is the wild bad boy side she likes, but I don't think she could handle a full time thing (nor could I) and she has said she is not attracted to crossdressers (I think this means males who have visible feminine traits)...why do I find that really ironic? Anyhow, its purely for enjoyment when my wife is involved and other times its on my own for my own education and gratification. At this point, I could probably dress anytime and it would not phase her, but I am careful to keep it in the 'fun' category when it comes to lifestyle.

[Nikki Rich]

Yes I played a bride in a dinner theater at church on time, it was all in fun but I really enjoyed it, I got to play dress up.

[texasm31]

Maybe she lived in a kinda tight house? I don't know. My sister liked to wear thongs when she was in high school (she still does, I think, I'm not sure) but she didn't get a lot of them like she wanted because we (my mom, sister, and me) lived with my grandma and if my grandma saw a thong in the laundry or in my sister's room, she would freak. (Imagine if she saw me wearing a thong...).

Definitely not. Whatever the reason, I was just bummed that they were so boring, as I would have preferred something a little bit sexier. But then again, if it had been a string bikini or something silky or flowery, it probably would have freaked my friend out even more.

On a side note, I don't remember any girls back then wearing thongs. It was something you'd see at the strip club, or maybe on a really special occasion, almost as if it were a "costume" as opposed to everyday undies. Nowadays, so many more people wear thongs and sexier undies daily.

[Robbiegirl]

As far as choice of underwear was concerned I was very lucky ! Maidenform Bras & Panties had a line called Sweet nothings and believe me they were all very cute silky and satiny lacy bras and bikini or French cut panties ! She was not pleased that with a stuffed bra I looked better in them than her !

[MatildaJ.]

She was not pleased that with a stuffed bra I looked better in them than her !

Why would you say that? Was it funny to both of you? Or are you proud that you were able to make her feel insecure?

[NicoleScott]

You can't pull off "just trying to be funny" very many times before people will start to wonder.
"Do you have to dress up as a French maid EVERY Halloween?"
"And a sailor girl on Veteran's Day?"
"And a secretary on Secretary's Day?"

[Robbiegirl]

OMG! Jessm I would never say anything like that ! She said it when we were both having fun along with alot of other funny remarks !

I adore women and always make them feel good about themselves

[MatildaJ.]

OMG! Jessm I would never say anything like that ! She said it when we were both having fun along with alot of other funny remarks ! I adore women and always make them feel good about themselves

Oh my, thanks for coming back to reassure me! Sorry for jumping to conclusions; I should know by now that online communication often leaves out the important part. Glad it was a fun time for both of you.

[Cindia]

I couldn't do it to be funny. I'd need to do it right, that is try to look like a girl, not a guy in a dress.