Did you ever put on something really Girlie just trying to be funny for your gal

[Robbiegirl]

And 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 sweet nothings) 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 wrapped a towel around my head like she always did and 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

[Asew]

Not necessarily funny, but a result of "funny" comments my wife made that I should wear a skirt I acted on.

About 4 years ago my wife and I went on an anniversary we went to the Poconos and my wife was wearing skirts and dresses since she knows I like them. But many times she kept saying things like how she wears the pants so I should wear the skirts, and if I like them so much I should wear them. At least a dozen times something that implied I should wear skirts. About a week after we got home from vacation I decided to dress and wait for her to get back from going out with her friend. Well apparently the friend came back here since they decided they would hang out the next day too. So I cover with a blanket and she was wondering why I was covered up and pulled the blanket off to see. She was like why are you wearing that. I reminded her of her many comments and she was like I can see why you would get the impression but she didn't mean those comments that way and could I please take it off. Also with her friend being on the other side of the bedroom wall made it awkward.

Talking to her about it now that she knows, she says she was surprised and thought I was doing it for her and at the time didn't realize I liked it.

[Beverley Sims]

My girlfriends dressed me up so as I could attend a pajama party with other girls.

I had a shared house and was the only male with four girls as boarders.

They wanted a party and did not want to leave me out. :-)

[JUSTME]

Oh yeah.. I had a GF dress me in her bra and panties once or twice. There was alcohol and I recall pictures that we laughed about a few times. LOL... That was back when you still had to develop the film. I can imaging the looks on the guy/gal’s face when they processed them..

Years later I hopped into bed in one of my wife’s bras ready to surprise her. Sadly, I did not get the reaction I was hoping for.

[Majella St Gerard]

Somewhere there are pictures of me wearing white tights, a pink tu tu and ballet flats doing my best Swan Lake 😂😂😂

[Petra1]

Yep, did that with both my ex-girlfriend and my wife.

[docrobbysherry]

Yes. My ex and I swapped roles for a huge, bar, Halloween party. She dressed as a guy a joke woman. Balloon boobs, beard and stash, ripped nylons, low heels, cheap wig, etc. This was eons before I began dressing.

It made such an impression on me, I forgot all about that nite until after I had been dressing for 10 years!:brolleyes:

[Robbiegirl]

I do wonder sometimes, since women are now so aware of crossdressing if its as easy to pretend about crossdressing as it use to be ?

[Alice_2014_B]

Back when I was only into wearing heels around the house and married to my ex I did something of the sort.

She wore about size 8 and we had gotten her a pair of sexy platform heels, they were about six inches high.
So one time I squeezed into 'em and waited on the bed for her.
Now, I wasn't expecting anything, was just for whatever.
She didn't think it was hot or anything, but didn't freak out.
That was it.

Current wife digs me in heels, but only in the bedroom or just around the apartment.
Or out fully dolled up of course.
:)

[Barbara Black]

I had come home with a few pairs of heels. Seeing the four inch spiked heels, she said that I was never going to be able to walk in those. Well, I hadn't really been dressing in front of her, but she did know that I dressed. So I promptly sat down in the living room and strapped them on in front of her, and wobbled (quite successfully) out of the room. I never asked if my ass was wiggling as well. LOL

[dawn459]

When Dawn459 was about 6yrs old
She found her mother's stockings &her
White&Blue diamond shaped figures on
Her shoes puts on the shoes with the hose and started walking wrong in her
Heel's because they were two big well all at once the hose slid down my legs and when I tried to walk the hose got hung on the heels & shoes went one way&Dawn459& the hose went the other way my mother&GrandMother got
A good laugh at my little escapade.
This started Dawn 459 on herCD journey
Through the early days of my young life.
After Marrying I asked my wife to help
Make wearing panties during our lovemaking sessions so I had a pair that had a flaw right above the crotch so she
Took a pencil and drew a circle around the tear & cut the hole out and
We both profited from that experience.
Have wore panties to bed regularly for the last 26 years not ever night but most nights.
I

[Lacey New]

Back many eons ago when my wife was young and frisky, (and i was too) as a prelude to bedtime fun, I would sometimes take a pair of her panties, put them on and would would then appear in front of her in a bathrobe , open it up and ask her "Is this what I have to do to get into your pants?" I also had some remote hope that she would accept it and that somehow it would become a gateway to open up to her about my wanting to wear panties and to crossdress. But no, instead it was always, "Take those off! and finally, "Don't do that again!"

[adam7476]

I wore stockings and a garter one time while making out with my wife. She isn't to keen on the idea of me wearing lingerie or women's stuff. She believe that should be for the women. So all I get to wear from time to time is panties that we bought. Every time I bring up about wearing her lingerie she says NO!

[Rayleen]

Adam, best to buy your own panties and stuff, women don't like we borrow their stuff.

Rayleen.

[adam7476]

I do have panties that we bought so I don't take her's, and I do have some lingerie. She just doesn't like the idea of me in the stuff with her around, so I have to be alone.

[jacques]

hi,
laughter is a good ice breaker - unintentionally - the first time I wore a skirt in front of my wife I was really nervous until she burst out laughing when it fell down to my ankles!
luv J

[Krisi]

I do wonder sometimes, since women are now so aware of crossdressing if its as easy to pretend about crossdressing as it use to be ?

Where do you get the idea that "women are now so aware of crossdressing"?

I don't think women are any more aware of crossdressing now than they were in the past unless their husband or boyfriend is a crossdresser. Remember, this crossdressing forum is not a slice of real life.

[HollyGreene]

Adam, best to buy your own panties and stuff, women don't like we borrow their stuff.

Rayleen.

Not always the case.
I had a girlfriend for about 3 years, who lived about 20 miles away. When I went to her place for the weekend, while I was in the shower she would hide my underwear and lay out a pair of her panties for me to wear.
When she came to my house for the weekend, she'd bring extra pairs and put them on me while we were in bed, and I'd wear them the rest of the day.
When she wanted to buy new ones, we'd go together so that we got ones we both liked.
Eventually I suggested we always buy two of each so that we could both have a pair and wear matching underwear, and I stopped wearing hers except when she wanted me to wear them.

[Vanessa maria]

My wife has known from day one before we ever gotten married i was am still am a gurly girl crossdressing male. In fact since we been married she has bought me dresses panties garter belts corsets bra and panty sets pantyhose make-up on top of what i already had before we got married. As she also insisted i go out fully dressed in dresses and all and said as long as i was happy and comfortable doing so she was also and she supported me being myself. And now i am taking hormones to make my breasts grow and my skin smoother. I cannot wait to have 44DD breasts.

[Krisi]

Vanessa, what sort of hormones are you taking that will give you smoother skin and 44DD breasts? Did you get these from a doctor or from the Internet?

Most actual transsexuals taking hormones under a doctor's care only see a small increase in breast size. Perhaps a "B" cup at best.

[Janie Jane]

It started three years ago when my wife went out to do the laundry and took all of my underwear with her, but was nice enough to leave a pair of hers on the pillow just to be a smart-aleck. I put them on and when she came back she was both surprised and delighted. She went out that day and bought some for me, and I've worn guy boxers maybe two-three times since then, and only for doctor visits.

[Glenda58]

Had a girl friend who knew I crossdressed. Came to her house one day to go out. She said she could see my underwear under my pants. Told me to take my off and gave me one of panties that didn't show thought told me to keep them. Later on she bought me a silk cami and tap pants to wear under my cloths and at night with her. That when I started underdressing. Bought her a Black dress with matching bra panties and slip. She gave them back to me saying they looked better on me and she knew I like them. It was all in fun when it started but she had a temper that I couldn't handle.

[Laura28]

Vanessa, what sort of hormones are you taking that will give you smoother skin and 44DD breasts? Did you get these from a doctor or from the Internet?

Most actual transsexuals taking hormones under a doctor's care only see a small increase in breast size. Perhaps a "B" cup at best. your going to be dissapointed 44dd I doubt hormones will give you those. But hey some is better then none. I am a full 38B

[Laura912]

Yes, I put my wife’s bra on my head with the strap under my chin and sang the theme song from the Mickey Mouse Club...M-I-C-K-E-Y etc.

[StevieTV]

I was in the wedding party for a female friend of mine. The night before the wedding we, meaning the others in the party, were in the hotel room. I put on a pair of her heels (same size) and came out of the bathroom saying "I'm ready for the wedding". She laughed.