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View Full Version : Best halloween for me, 1966!



shayleetv
11-06-2014, 11:26 AM
:D This last Monday night my wife and I had dinner with our friends that introduced us to each other 49 years ago. Darrin was my friend and Kristin was my wife's. Both my wife and I and Darrin and Kristin got married the same year. Over the years we have regularly met and had dinner together. This last year and a half they have been serving our church in Texas so we haven’t had the chance of getting together. Lots of catching up to do.

Since it was close to Halloween Kristen had to talk about our first Halloween as married couples. My wife and Kristen worked at the same office so they had time to plan together. Kristin thought it would be fun if we all crossdressed. My wife jumped on the band wagon and started the ball rolling. I had purged before we got married so I was reluctant to start this ball rolling again, but she was so excited I gave in and submitted to her. (My wife didn’t know about Shaylee before we got married) We borrowed a suit from an old neighbor who had a son about my wife's size and my mother took one of her dresses and sowed the seams up the side so the dress would fit. My wife had a friend who was a cosmetologist come and do my makeup, a well done professional job. I emerged as this very tall beautiful girl and my wife was this short aristocratic man with a curled mustache and beard.

When we got to the party, Kristin greeted us at the door with this very puzzled look on her face because she didn’t recognize us. (By the way Darrin chickened out and they didn’t crossdress.) My wife spoke and said “I thought we were both going to crossdress”. That is when she realized the tall brunette was me. The costume was a hit and I became the center of attention. Everyone wanted me to do something girly. Darrin kept asking me to talk in a girls voice not knowing how hard a thing that is unless you have practiced a lot, I never have tried. I talked in falsetto and he went crazy with how I should have been a girl for real. Blake's’ date followed me around all evening asking strange questions about how I felt about being a girl. She had never seen a adult male dressed so passable as I was and was so intrigued she forgot about her date. Kristin was so taken at my impersonation, there haven’t been too many time when getting together that she hasn’t talked about it. That is why it has been my best Halloween ever!:D

Katey888
11-06-2014, 01:06 PM
Shaylee, that is a darling story and recollection... love it! :cheer:

And an interesting perspective on social behaviour too... perhaps things have moved on more than we realise...? :thinking:

Katey x

kimdl93
11-06-2014, 07:05 PM
Isn't it funny how the truth of a person can reveal itself? What a wonderful memory to share!

darla_g
11-06-2014, 07:07 PM
that was a very enjoyable story. my first experience crossdressing was for a Halloween as well

stacycoral
11-06-2014, 07:32 PM
Shaylee, what a great story, now you can do it again and surprise them again, now you will be feeling normal about it. hugs.

DebbieL
11-06-2014, 07:48 PM
Sounds like Blake's date, whoever he was, might have been one of us.

It's so great when you can go to a Halloween party as a girl and be accepted and appreciated. Congratulations!
Did anybody notice you walked a bit too well in heels?

JamieG
11-06-2014, 08:14 PM
Sounds like a great time. I don't suppose you have any pictures? I will always treasure my first Halloween dressed en femme too. Mine was a bit more recent though: 2003! It took me 11 years to do it again... dress for Halloween that is, obviously I've dressed many times since then for other reasons...

S. Lisa Smith
11-06-2014, 08:19 PM
What a wonderful story!!! It's a really great memory!! I the last time I dressed for for Halloween was 32 years ago...

Sandi Beach
11-06-2014, 10:48 PM
Going to a Holloween party is actually what got me started. My wife hated Halloween, and getting into costume, and was looking for excuses not to go one year. I must have given her 50 costume ideas, and she rejected them all. When I finally suggested we go switched (her the man, me the woman) she agreed. I didn't find out until the night of the party that the only reason she agreed to that, is because she thought I would never go out that way, and I would chicken out. Mif I chickened out, we would not have to go, and that is what she wanted. I had so much fun, and it felt so good with shaved legs, etc, that party is what got me started dressing afterwords. I never had a desire to dress before that night.

But, reading your story has left me wondering many things. You mentioned in your story that your wife did not know about your dressing before this party. Does she know now? If she does, how long after this party did you share? Also, do your friends also know about Shaylee now too?

shayleetv
11-09-2014, 04:19 AM
It was about 8 years later that she found out about my crossdressing. It nearly caused a divorce. How I prevented that was to completely stop dressing. This also had some great negative affect on our marriage because of some sexual hang ups I had with intimacy linked to my crossdressing. My crossdressing came back with a vengeance after I retired and my wife was still working. This time I found a therapist who knew what she was talking about and helped me over my guilt and my wife to understand me. She accepts Shaylee into her life and is sometimes the one who wants to have some time with her. I'm now 73 and since my crossdressing is out to her and she loves me for it we are now more loving toward each other.Only out to my three daughters and no one else.

Marcelle
11-09-2014, 05:59 AM
Hi Shaylee . . . what a great story! Thanks for sharing.

Hugs

Isha

Beverley Sims
11-09-2014, 09:18 AM
Sounds like a groundbreaking Halloween.

Valerie Sparks
11-09-2014, 06:18 PM
Halloween has good memories for me, too.

I'm not sure if my mom wanted me to be a girl or if she just recognized the tendencies in me, but at Halloween when I was 9 (1964) she dressed me up as you can see in the picture. It was an old fashioned-dress with a hoop skirt under it.

The subdivision we lived in had a costume contest and I entered wearing that outfit. The judges lined all the kids up in a circle and started scrutinizing us. There was to be a prize for the best boy's costume and a prize for the best girl's costume. They selected a boy first and I thought, oh well, that's that.

Then they come over and asked me my name. I told them and the judge said "Wait--you're a boy?" He then conferred with the other judges and I ended up winning the best girl's costume.

Looking back on it, it's not all that great a costume. But that adrenaline rush of positive reinforcement really sent me on my way to where I am today.