Did you Ever Put on a Gals Dress or Lingerie to kind of test the waters ?

In an atempt to 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 done laundry and 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

No, I never had that courage.
I did date a wonderful gal who wore pantyhose all the time. A few times while being intimate I would comment on how silky they felt on her and that they must feel wonderful to wear hoping she would take the hint and ask if I wanted to try them. She did not though and I never got to take that step that might have opened the door wider.

Hi Robbie,

I had a GF a long, long time ago who had a thing for dressing me up. She was totally into it. Sadly, I was never able to find someone who was open minded. All the women i dated were not all that adventurous. My wife knows and has gotten to the point where she doesn't care what i wear. I still tread lightly when she's around

When I was dating my now wife, she wore hose daily but, like many, couldn?t wait to take them off. One night I hinted that she leave them on. She heard me, but took them off. Surprisedly, she laughed, threw them at me and said, here, you wear them, you?ll see how uncomfortable they are. I took the leap of faith, went in the next room and put them on. They were small and ooops, I put a run in them. When I returned, I showed her including the run. She cracked up laughing, but could see I enjoyed wearing them. That opened the door. We talked and talked. For my birthday, she surprised me with pantyhose, stockings and thigh highs. That was the beginning. I?m now retired and dress most days, definitely hose, panties and bra. Her support and help has and continues to be appreciated.

Hi My journey started very much like NancySues. Loved nylons and always pestered partners to wear them then one night my wife complained of cold feet, I saw an opportunity to get her to wear them to keep warm but instead she asked me to wear them instead and she could snuggle up to me. This rapidly progressed to a full FLR and my position now as a full time 'housewife' As you can see by my photos she takes it very seriously.

I didn't do it to test the waters. But, I did tell her about 5 months after I started wearing panties that I really enjoyed them. She was not particularly keen on the idea. However, as I approach the 3 year anniversary of when I started wearing just panties, I'm sitting with her in our family room wearing thing highs, panties, bra, forms, and dress. This is now an almost daily occurrence after dinner. Like me, she doesn't understand the attraction I have to wearing women's clothing; but, also like me, she is accepting of it so long as I remain in the closet to family and friends.

Great Story. I was dating a girl and she had picked up a new one piece swimsuit. While getting ready to go out she threw it on the bed saying she hates how tight they are and I said aren't they stretchy? She grabs the suit, drops to her knees and says give me your leg. I strip down and stepped in. She slides this up on to me and then stood back smiling. Said I look good in it. Course we had an awesome make out session and I told her I really liked it. Totally opened the door for what was a great few years with her. Still, I think I miss that suit more than her....lol

When my wife and I had been recently married when I bought her a long white peignoir set in medium size. I did not know anything about women's sizes. She was 5'2" and 115 pounds. The gown swam on her. She laughed about the incorrect size. She had the habit of ditching the long gown after play time. I have an addiction to nylon so I decided to try it on. She walked in on my in the kitchen drinking a glass of water. "Why are you wearing my nightie?" she asked. I told her the truth that I loved the feel of the nylon. I did not tell her that my first foray into women's attire had been my mother's nylon full slips and one of her floor length nylon nighties. The short story is we ended up in mid-town Manhattan buying me a pink peignoir set and a black floor length nightie. It added a little kink or enhancement to the bedroom scene that included garter belt and hosiery after awhile. The entire "fetish thing" exploded about a decade later when our second born, a daughter, yanked a vivid red Vanity Fair bra out of the bottom draw of my armoire. "The Talk" ensued. It was a little rough after that.

Not too long ago my wife was cleaning out the back of her side of the walk-in closet. All the nightgowns that no longer fit her were headed to a thrift store, except for that white peignoir. Knowing that the only nightie of scores that was going to possibly fit me she told me to "take what you want" which floored me. I did take it. So, if you read the "What are you wearing right now?" section you'll read my comments about still sleeping in 50+ year old vintage peignoirs.

I too had a similar experience as Stephanie47.

One of the first experiences in wearing something feminine was a pink peignoir and matching panties that my wife gave me as an anniversary gift. Wow! What fun, especially when she wore her's at the same time.

As a reminder to readers, I had the "great reveal" conversation with my wife on our second date, so, by the time we were married, we were both totally comfortable that CD'ing was going to be part of our life together.

Now, back to the nightie story. No matter how vintage those nightie sets have become, we continue to enjoy wearing matching panties and peignoir nighties for comfortable evening attire. There have been many memorable evenings when I would come home from work to find two sets of matching peignoir nighties, panties, and bra all laid out neatly on the bed. Hint, hint!

Later, as she came to understand just how much I enjoyed such evening surprises, she frequently added having all of my make up and wig of her choice all set out neatly on my bathroom counter.

Occasionally she would put a sticky note on the bathroom mirror with sweet suggestions or short notes that she hoped Teresa would visit. My favorite note was "I want my girlfriend to visit, NOW!" I put that note in plastic to save for ever and ever. Wouldn't you?

As you might guess, with this level of acceptance my wife has always treated Teresa as her girlfriend, and never slips by calling me by my male name. When Teresa is present, she treats me 100% as the girl I pretend to be.

We talk about every subject imaginable, including such subjects that only women share with other women. The more we share out thoughts and feelings about being girls, the more real the experience is for me as I pretend to be a girl when Teresa comes out.

I should clarify that I am not trans per se. I love being a man, but I also love "pretending" that I am a girl. I love the mere thought of it, the attire, and the feelings generated when I let myself feel and act like a girl. I am so lucky to have a wife that understand this.

She is not the least bit confused that on some days (and nights, and occasionally for weeks at a time) I feel like a girl. However, she totally accepts that. When I ask her how she its able to be so accepting and casual about my dual persona, she merely says, "Feeling and pretending that you are a girl is just part of you. It just is!" She has said more than once, "I know you are a very masculine man, so when you pretend to be a girl, I too pretend you are a girl. It's really quite easy!"

For those who are in shaking their head in disbelief let me just say that I know that I am the luckiest cross dresser on the face of the earth. It just doesn't get any better. Please understand that I share this with you not to brag but to explain that this level of acceptance is totally possible when a wife is able to accept her man, all of him, as he is.

The key to our success as a couple has been that we were both 100% honest with each other from the day we met. Getting started on the right foot make acceptance of CD'ing more possible than a wife finding out about it years later. I am a strong advocate of early disclosure. Yes, there is risk but there is also a better likelyhood of acceptance. Enough of my preaching.

If any readers wish to discuss my experience in private, please feel free to address your questions with a PM.

Thank you for sharing this wonderful life that my bride and I have enjoyed for many years.

Teresa

p.s. After drafting this tell all explanation of how we both enjoy somewhat old fashion matching peignoir nighties, panties, and bras, I am quite sure that my wife and I will enjoy a quiet evening together as two girls who love being girls. Night night.

Thank you, Teresa for this, I think it means everything:

"The key to our success as a couple has been that we were both 100% honest with each other from the day we met. Getting started on the right foot make acceptance of CD'ing more possible than a wife finding out about it years later. I am a strong advocate of early disclosure. Yes, there is risk but there is also a better likelyhood of acceptance. Enough of my preaching."

If you can be honest and truthful, it can only encourage understanding of your crossdressing. Also if your masculinity is without question, then that is an advantage because, as in my case, your SO will not "mistrust" your motives.

I started as a young adolescent; being "interested" in lingerie: my sister's and brother's gf's panties, (clean or used!), bras and stockings; trying them all on if I felt it was safe! My next exploit was to "kidnap" a beautiful black lace bra that a pretty german girl had left in our bathroom while going for a swim in our pool - she couldn't find it on getting out and I know I was a suspect, but really enjoyed the trophy for a long time; wearing it and sniffing her perfume!
From this moment on I took other "trophies" which gave me the idea later to start my own collection. This has now grown into a fascinating and exciting collection that I always enjoy going through.

Today I try on my wife's panties and bras and if she likes what she sees she will compliment me, saying how they suit me! She is being kind and nice to me, but also truthful. We often chose her lingerie and mine together and she will help me selecting what we both like and making me at ease in "her" department. I am a lucky man! :):)

Yes. With my second wife. she had me wear one of her satin nightgowns to bed one night. It was amazing sex that night however it scared her and we basicaly never had sex again after that night. I got my needs met outside the relationship till I came across a woman who was so totally amazing that we both wanted more than a fling and have been living together now for 3 years happily with me underdressing daily and wearing my maids uniform to do house chores.

Robbie, I guess the only reason why GGs haven't already posted in this thread is because they finally tired of repeating the same things over and over along all this years. I'll try to say it for them: you are not testing the waters. In the situation you described, your wife (like most wives in the same situation) just takes it as a joke and not an attempt to hint her at some secret tendency you have. If you like to crossdress just tell her.

Really Diane ! I was wearing a very frilly bra and panty set ! If it was just a dress i think most women would just laugh but I do think women are smarter than that

and in this day an age would certainly have some questions about my manhood !

Trust me it took alot of courage to model matching underwear !

I've never worn my significant other's clothing without permission, but I _have_ tried items on while in relationships.

When Lularoe first hit the market, my wife insisted that I try on a pair of her new leggings to see how soft they were. She mostly accepts my dressing, but it was still a bit of a jolt to have her be so direct and open with it.

My first time wasn't as positive, though. I'd reconnected with an old acquaintance, and we'd been together a little over a year and had just started living together. She was a Mary Kay rep and I'd volunteered as a model for her to practice techniques she was learning without letting on that my enjoyment was deeper than just being a supportive boyfriend. One Halloween, she took it to the next level and suggested that we swap clothes to hand out candy in our neighborhood, and I finally let it out of the bag that I had crossdressed before.

She was initially intrigued by the revelation, as she was studying for her Masters' in psych en route to becoming a sex therapist, and we had a REALLY fun night after we shut off the porch light. Oddly, the dress she picked out for me was a much better fit on me than it had ever been for her, which was an unfortunate harbinger of doom for both the relationship and her career. She was never able to get over the fact that I looked better than she did in her own clothes (HER admission, not mine) and also realized that she wasn't nearly as open-minded as she thought she was.

My biggest regret as that relationship ended, however, is not leaning in to my crossdressing after the breakup.

I did this to get my wife's attention. It's grown into a full on her dressing me and saying how I wear her clothes better then her.

I told my current gf right after we met that i like dressing up. At firs she was not thrille but we keept talking.7 years later we are still dating

Just a few weeks before High School graduation, my long term girlfriend and I were taking a bubble bath together in her tub and we were starting to having a strange conversation about body part swapping and I thought it was going to lead to me trying her bra and panties on in front of her. But as luck would have it we heard a car pull up and had to do a mad dash to get dressed before her aunt came barging into the house. Me half wet and sudsy met her at the back door while the gf ran upstairs trying to find a bra and top to put on. Lol. Was kind of embarrassing (but not as embarrassing as the time we came into her house one night after rolling around in the back yard in the dark and her mother noticed that her top was on inside out!). Need less to say we never did finish that conversation and I was off to college the end of the summer then we broke up.

My litmus dressing test was with first ex wife. On Halloween I did just that, I put on the the pull up nylons and garters and snuck into the bed. What came next was, "what are wearing, why and OMG , they look better on you then me.". A few years later, she got tippsy, which was a lot and teased me in front of another couple at Dinner party. It still annoys me to this day, she would betray me to tease like that.

I used to date a woman who was older than me, she was the gorgeous secretary and fit the role perfectly.
For some reason after her & I became close it came about that she wanted me to try & wear pantyhose since I always commented on how sexy her legs looked and felt.
One day she brought pantyhose in a little bag for me to try on at work.
I agreed, took them into the bathroom stall & there in the bag was a pretty pair of white satin panties to go with the nude pantyhose. I wore them under my pants to show her I?d go along & the rest is history.
This went on for about 4 years!
She would bring in full wardrobes, I would get fully dressed in the stall!
The sex was amazing & she would wear whatever I told her to wear also, we got very very daring in our office fun.