Dressing for a friend?

[Heather76]

My wife is heading out of town Tuesday and will return Saturday. The one lady who knows about my cross dressing will be working both Tuesday and Friday. She works parttime where I volunteer. She has never met Heather. I believe I am going to stop by her workstation (outside) and ask if she would care to meet my more feminine self. If she would, I can head home, get dressed, put on makeup, etc. and return within 90 minutes. I'm really hoping she is game for it. Mostly, I would like her critique; good, bad, or indifferent. I could just surprise her, but I don't want to force Heather on her. She's always been super supportive and understanding when we've talked about it, but I know seeing me dressed as a woman and talking about it are 2 different things. I am rather nervous just thinking about this.

[Raychel]

Sounds like fun Heather. I hope it works out for you,

[Bruce64]

That will be fun, made me remember a Writer story and fantasy. It started like this, she knew about my dressing up and invite me over.....

[Kris Burton]

Sounds very interesting indeed Heather. Sounds like you are experiencing anticipatory butterflies too. You are quite right about asking her about a meeting first too, a surprise could be a bit much. Without throwing a wet blanket over all this tho I must ask is your wife OK with you meeting another woman? As supportive as my wife is I know that would be a big red line for her, but everyone's boundaries are different.

[Crissy 107]

Good luck Heather!

[cdinmd206]

As Kris said you had better make sure your wife is ok with you meeting another woman, or all hell is going to break loose

[Helen_Highwater]

You're doing the right thing in asking first. Hopefully she'll want to meet your alter self and as you say, a bit of a critique of your dressing could be very valuable going forward.

[docrobbysherry]

Sounds weird to me, Heather.
Why not just show her photos and see how she reacts? Then, think about meeting some other time and place?

And, after running this all by your SO!?

[countrygirl]

So how did it go? Tell us all the details.

[Heather76]

To answer a few questions. This woman is the only person who knows I CD. She works, I volunteer, at what is basically a wildlife preserve. My wife does not know she is aware zIM CD. As some may recall, she saw me in the store the day I purchased my first dress (ROSS). A few days later when our paths crossed, she asked how my wife liked the dress I had bought for her. I will NOT lie and told her the dress was for me. She has been super supportive and does not understand why my wife has an issue with it. We've had many nice conversations about my hobby and she has seen numerous photos. My wife has never asked if anyone else knows I CD. If she were to ask, I would tell her the truth. I believe my wife would be okay with this lady as she is not a relative or someone who knows our circle of friends.

On to today. After dropping my wife and her friend at the airport, I drove by the nature preserve and did not go in. I knew she was working at the admissions gate in a booth by herself. I also knew she would be off work around 2:00. When I got home, I put my makeup on and got fully dressed. I looked at my watch and it was about 1:15 p.m. I arrived at the admissions gate about 1:30. She did a double take but did recognize me. She got off work at 2:30 and we agreed to meet in a particular section of the nature preserve. It was wide open with other people able to see. We sat on a park bench and talked for over an hour. Topics were several and varied - not just about my cross dressing. I made sure she knew how much I appreciate that she is non-judgmental. BTW, she isn't a young lady. She is 60. Well, to me that's young.

Anyway, between waiting for her and the time I spent with her, I enjoyed a good 2 hours of walking around and talking all the while out in public. There weren't many others in the area, but there were others. I loved every minute of the afternoon. At my request she took a couple photos with my phone. Here's one of them.

20250520_152809.jpg

[Rhonda Darling]

Heather, you chose a very pretty dress for your meet up. I'm in no way surprised that Noone in the preserve paid you any inordinate attention. You look great. I'm glad it went well.

Like others, I urge caution. Your wife may well take this activity as an affront to your marriage. Jealousy and fear have no bounds, and trying to explain it after the fact will likely be difficult. Be careful.

Best regards,
Rhonda

[bridget thronton]

Nice picture

[Fiona_44]

Nice story Heather.

[audreyinalbany]

hmmmm...I dunno seems to me like a bit of hair splitting with 'I won't lie'. We can ( and many have) debated the actual definition of lying, but it sorta seems like meeting another woman while dressed and not telling you wife is pretty darn close to lying.

[Debs]

Its something you have to do, otherwise first youll regret not doing it, then if you dont a "what if only" question will buzz round in your head for the rest of your life. Thats why I tell peeps to get dressed get out there in the real world, its fun, otherwise when your 90 years old sat in your care home thinking "what if only" will buzz you, now I'll be sat in that chair with a big smile on my face with lots of happy memories of going out dressed 20241031_172813.jpg

[alwayshave]

Heather, That is wonderful. I'm glad that you had a good outing with your friend.

[Julie York]

Sounds weird to me, Heather.
Why not just show her photos and see how she reacts? Then, think about meeting some other time and place?

And, after running this all by your SO!?

Ditto. Sorry but I've seen Road Runner cartoons with less chance of going wrong for someone. Think this through very carefully and then don't do it. You're welcome.......
Well I suppose if I was a coward I could delete my post after now reading of your good outcome. The page suddenly updated about 2 pages so I didn't see the update initially! But wow......OK. I was wrong. But I still feel that maybe you are setting up a really big problem. If it isn't a problem then have you told your wife about this great adventure?