Did you ever surprise a Gal by modeling her lingeire pretending to be funny

[Robbiegirl]

To kind of introduce her to your fun, kinky side ? How did she react ? Did it help to open the door ?

About 30 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. I just decided to go for it !! Since she is a bit curvy and I am skinny I knew Her Babyblue lacy French Cut Panties & bra fit fairly well and I made sure to try and not look excited once i put them on. I then stuffed the bra and wrapped my head in a towel just like she always did . 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 !
At the time she mentioned she didn't like the fact that I looked good in her underwear but never seemed interested in talking about it again. No Teasing, darn ! I was hoping she would want me to model other things at a future date but no such luck

[Alice92]

I surprised almost all of my girlfriends by wearing some of their clothes in front of them. They all reacted like it was a joke, asked me to stop acting like a fool and give them their things back. I never think it was a good way to confess my penchant for crossdressing but their looks and little remarks were interesting to observe. A way to test the waters... None of the reactions gave me the confidence to go any further.

[Kris Burton]

LOL! That was my introduction to the wonderful world of CDing! Many years ago, I surprised my girlfriend - later to become my wife - by putting on her nightgown. I was just joking around, I thought she would get a good laugh over it. She did...and asked me if I liked it. I said no. I lied. And so it began.

[kimdl93]

No, never as a joke.

[Majella St Gerard]

The second time me and my second wife were intimate she got up to use the bathroom, her panties were on the floor, I picked them up and put them on and got back into bed. She came out and saw me and just smiled, I told her that I was into wearing panties and she was more than cool with it. I was not going to hide this part of me anymore and figured I might as well get it out in the open early before we got too involved. She was just as kinky as I was and we had lots of fun. She helped me explore my cross-dressing and helped me accept it and not hide it and I helped her explore her wild side, she was a bit of a nymphomaniac, which eventually led to our breakup.

Peace & Love
Gerri

[alwayshave]

No, never. The only person whom I have opened up to about my hobby is my now wife and she was introduced after we had the talk.

[ChrisP]

Yep. In grad school. When we broke up she told every mutual friend we knew. To this day (more than 30 years later) I?ve had friends joke about it.

[ziggie]

Back in grad school I had a friend who wanted some pictures of herself in a new dress she had recently bought. I don't remember exactly how it happened, but some of the pictures ended up being of me wearing the dress. She sent a copy of one to a professor we had both studied under as undergrads. Unfortunately, I have lost track of the photo.

[Christie ann]

Only once. You know how to fly a balloon made of lead?

[Wendy-Lyn]

Her lingerie? No.
But I did surprise a girl once by going upstairs and changing into a matching set comprising black bra, cami, half-slip and panties that I'd recently bought.
I came back downstairs, not really expecting it to go well - and it DID!
We never had a real relationship, more 'friends with benefits' - but we are still good friends 30+ years later.
She visits regularly, and actually visited for a couple of hours yesterday evening - and we sat like an old married couple watching TV and chatting while she did her needlework - and yes, I was dressed.
In fact, one of my bras was gifted to me by her some years ago - I keep it, and sometimes still wear it, although it's too small for my forms.

[DianeT]

The first testimonies prove, if need was, how much crossdressing is remote from women's experience and how little chance there is that they will get a hint of the sort: they simply think it is a joke, not a message.
Which makes these attempts at testing the waters using very indirect methods very ineffective. Before my coming out to her, I asked my wife to watch the movie Crossdressers (a French documentary). I didn't do it to send a message, but I thought it may raise suspicion and decided that if it did it would simply be time
to think of having a conversation. It is worth noting that my wife at the time already wondered why I remarked a few things about women attire and makeup that the ordinary male did not (in my opinion this is linked to my curiosity not dressing but on second thought my dressing could very well stem from my curiosity so chicken and egg matter there). We watched the movie and it didn't raise any suspicion (I know because I asked her after my coming out). The idea of her husband being interested in crossdressing was simply out of the equation. Like for most women.

[britskye]

Yes, i've been with my wife for over 18 years and there were several times where i'd be joking around. once i was bringing the clean clothes up to the bedroom and one of her nude bras was laying on top. i put it on and walked into the bedroom holding the rest of the laundry. she laughed. couple other similar instances in the past with her.

the comfort of those memories helped push me to open up to her. she doesn't find it humorous anymore.

[Sometimes Steffi]

Ha, ha, ha. No way. There's no going back from that.

But one Halloween a long, long time ago, I did talk her into going to a Halloween party as a French Maid and a butler, with guess who being the French Maid. I don't think she had any clue at all, until I started talking about padding my bra and makeup. I used socks for padding. That's what all the girls who developed later used in school (so I've been told). And makeup was kind of a red alert for her. Since I had a mustache at the time, it didn't make any difference.

I do think that she might have thought that I liked crossdressing a little too much.

I did win the bet costume (for men) prize at that party.

[docrobbysherry]

Heck no! I began dressing after we'd been married nearly 10 years. By then, she couldn't fit into any of her sexy things anymore.

So, I fit into and looked better in her pretty things than she did! That would have pissed her off beyond belief!

[SaraLin]

No. Her stuff is HER stuff. I wouldn't do that.
Besides - they wouldn't have fit me anyway.

[Jane G]

Nope, never happened to me.

[GretchenM]

Long, long ago I did. She didn't think it was funny at all. Maybe on someone else, but not on her husband.

[missjoann49]

My late wife used to put beautiful lacy nightgowns on me. What started off to be somewhat of a joke , soon became
a reality and so it goes

[Cheryl T]

No I never did that.
I did hint a few times to a girlfriend about her pantyhose. She wore them all the time and when we were intimate I would tell her how silky they were, how they must feel incredible to wear and such, but she never took the hint to ask if I wanted to try them. I so wish she had, I was dying to do it with her. It would have been such fun.

[JocelynJames]

No, although I had a gf that I once remarked how incredible she looked in a particular piece of lingerie. She offered to have me try it on later , which I blushed and said no. That one was adventurous. I do sometimes wonder what life would have turned into if I stayed with her. It is pretty damn great how it is , though.

[Glenda58]

No, I didn't my girlfriend surprise she surprise me while shopping for her. She went into the changing room to try on a skirt. Called out to me that she needed a size larger to bring it in to her. When I did, she held it up to me then said to put it on. She knew I was wearing panties. Try on the skirt she then put a top up to me and said It looked cute. That was the first time in a dressing room.

[giuseppina]

While I've never been in a relationship, that's not something I would do.

[Debbie Denier]

Yes in the early days. She thought it was funny then but not now.

[Paulie Birmingham]

Many times when i was younger with many different women. Always led to fun times
Noone was wvwr upset or angry

[Lacey New]

Many years ago early in my marriage, I would occasionally take a pair of my wife?s silky nylon panties out of the hamper, put them on and then wearing nothing but a bathrobe, I would flash her and ask ? Is this what I have to do to get into your pants?? Of course, I was trying to initiate two things, the first and most obvious was some sex. The second was to test her reaction to me wearing panties. Whether she thought it was sexy and fun and if she was in any way tolerant to the idea. And while I was often rewarded with the first objective, the screech of TAKE THOSE OFF! told me that I had no chance with the second objective.