• This topic has 3 replies, 4 voices, and was last updated 6 years ago by Anonymous.
Viewing 3 reply threads
New Forums
  • Author
    Posts
    • #26812

      Someone asked this at http://www.crossdressers.com and I had to post my response here too with some updates.

      Did Dressing as a Female At Halloween Help with your “coming out” to your wife/SO?

      My response:

      It was a major icebreaker.

      My wife has dozens of wedding dresses from her job (it’s a long story). We keep them up in the attic.

      I had never dressed in front of her or outside at all.

      Well, a couple of years ago we needed to put some up in the attic and I’m not exactly sure how it went down but either her or myself said “any of them my size for halloween?” Which lead to me slipping off my jeans and trying on 5 or so dresses. (Really tough to hide the excitement in my briefs.) She bought me a bra, makeup and various other stuff. I found a wig. So that year we went to the neighborhood party as a married couple, both in wedding dresses. It was very exciting on a personal level, but my male neighbors were really asinine which tempered my thoughts about doing it again. Mostly getting felt up by guys and me telling them “dude, that’s a pair of socks, you know?” But I won the custom prize, $50.

      The next year, I went with some cartoon outfit that truly sucked.

      But 2015, thank you Caitlyn Jenner! We went as the Jenners! My wife as an early version of Bruce and me as Caitlyn. Pink fog time. Got to shave my legs, chest, pits and got my back waxed. Bought breast forms to glue down with a couple of other bras. We did a trip to a resale shop to find an outfit (really freaked out some teens looking for prom dresses) where I probably had 3+ women throwing dresses over the fitting room door for me to try on. Had a trip to a nail salon where I got a mani-pedi with deep red color. Heels from Sears. TOTAL DIVA!

      As this was a different party, much younger crowd, I got felt up by a bunch of women (and reciprocated). Had long chats about leg shaving and boobs. Had one woman do a heart to heart about her transgender brother (don’t know if she was trying to get me “out” or not.) The weird thing was several woman made the remark to my wife (with me in ear range) “What if he likes it too much?”

      I won a trophy for best costume that party too. (Plus we were invited to several other parties that unfortunately we could not attend.)

      So several months ago, my wife is sizing some wedding dresses to loan to a friend for an event and she says “hey, try this on, and this one too. And this one.”

      And it comes down to this, with my Caitlyn wig is hanging prominently in my closet. My wife said to me the other day, “you know, the other month when I had you try on those dresses… you really liked it didn’t you?”

      I am going to turn these two halloweens into a ladies night out dinner in Philly this fall. I’m planning it in my head now.

    • #27107
      Patty Phose
      Duchess

      The first time I dressed fully fem was also at a Halloween party at college when I was 18. I also found girls and guys like to flirt and touch me. It was great with the girls and strange with the guys. It really was a wonderful and life changing experience including what girl power is. I went to many other dress up parties over the next four years and loved each and every one of them, including the getting hit on and being touched.

      I had been dressing and partying for a couple of years before I met my wife. When we met we were both  wearing pantyhose with short shorts and noticed each other. She liked how my legs looked so nice, shiny and smooth.

      The first time she cam to my place she noticed lots of girls clothes. I had closets full of dresses, shoes, wigs, and drawers full of lingerie, bras, panties and pantyhose. She thought I lived with a woman and was visibly upset. I was thinking of what to tell her and decided to just come clean. I told her I didn’t just wear pantyhose. I dressed up a lot in other girls clothes too. She asked me to show her.

      I chose one of my favorite outfits, went in a bedroom and put it on. It was everything. Dress, heels wig, bra with breast forms, makeup and of course pantyhose. When I walked out she was stunned. She couldn’t believe how pretty and sexy I was. She got a kick out of it and liked it a lot. I told her she could come to my next dress up party if she wanted. She went with me to many of them and we had a great time. It was also a lot of fun to go shopping with someone to pick out outfits and get help with my makeup.

       

    • #29164

      Oh yes, I certainly attempted to use the “Halloween costume” angle to come out to my past girlfriends over the years.  A couple of them laughed it off and it didn’t go any further, but most of my past girlfriends jumped at the chance to get me dressed up.  While we had a blast, I never admitted to any of them that for me this isn’t a costume it’s a part of my identity.

      Enter my wife.  While we both are Halloween junkies, we had some elaborate costumes involving heavy makeup and stuff over the years, I never brought up the concept of dressing in a female costume at all.  Then one day, she comes home from thrift store shopping with this gorgeous long burgundy medieval princess/queens dress (in my size) and lays it on the bed and says “you should wear this for Halloween this year”.  This was when we were still dating and before I had come out to her.

      I was absolutely shocked and didn’t know what to say.  Had she figured out my secret?  Did I screw up somewhere along the line and leave evidence of my dressing??  Turns out no, but as we reflected on it years later she told me that she knew somewhere deep inside of herself that when she saw this dress, she immediately knew that she needed to buy it for me.  I guess a part of her already knew.

      While I didn’t take her up on her offer that year out of absolute nervousness, I came out to her later that year and we were engaged a few months after that.  I did get my chance to wear it the very next Halloween!

      So yes, I very much have to say that dressing up for Halloween definitely helped me not only come out to my wife, but her insanely intuitive offer to dress me up for Halloween solidified in my mind that she was the one for me and that I needed to come out to her.

      <3  Lauren

    • #85065
      Anonymous

      2016_personal stories: oh to be rachel original post: 

      Someone asked this at http://www.crossdressers.com and I had to post my response here too with some updates.

      Did Dressing as a Female At Halloween Help with your “coming out” to your wife/SO?

      My response:

      It was a major icebreaker.

      My wife has dozens of wedding dresses from her job (it’s a long story). We keep them up in the attic.

      I had never dressed in front of her or outside at all.

      Well, a couple of years ago we needed to put some up in the attic and I’m not exactly sure how it went down but either her or myself said “any of them my size for halloween?” Which lead to me slipping off my jeans and trying on 5 or so dresses. (Really tough to hide the excitement in my briefs.) She bought me a bra, makeup and various other stuff. I found a wig. So that year we went to the neighborhood party as a married couple, both in wedding dresses. It was very exciting on a personal level, but my male neighbors were really asinine which tempered my thoughts about doing it again. Mostly getting felt up by guys and me telling them “dude, that’s a pair of socks, you know?” But I won the custom prize, $50.

      The next year, I went with some cartoon outfit that truly sucked.

      But 2015, thank you Caitlyn Jenner! We went as the Jenners! My wife as an early version of Bruce and me as Caitlyn. Pink fog time. Got to shave my legs, chest, pits and got my back waxed. Bought breast forms to glue down with a couple of other bras. We did a trip to a resale shop to find an outfit (really freaked out some teens looking for prom dresses) where I probably had 3+ women throwing dresses over the fitting room door for me to try on. Had a trip to a nail salon where I got a mani-pedi with deep red color. Heels from Sears. TOTAL DIVA!

      As this was a different party, much younger crowd, I got felt up by a bunch of women (and reciprocated). Had long chats about leg shaving and boobs. Had one woman do a heart to heart about her transgender brother (don’t know if she was trying to get me “out” or not.) The weird thing was several woman made the remark to my wife (with me in ear range) “What if he likes it too much?”

      I won a trophy for best costume that party too. (Plus we were invited to several other parties that unfortunately we could not attend.)

      So several months ago, my wife is sizing some wedding dresses to loan to a friend for an event and she says “hey, try this on, and this one too. And this one.”

      And it comes down to this, with my Caitlyn wig is hanging prominently in my closet. My wife said to me the other day, “you know, the other month when I had you try on those dresses… you really liked it didn’t you?”

      I am going to turn these two halloweens into a ladies night out dinner in Philly this fall. I’m planning it in my head now.

Viewing 3 reply threads
  • You must be logged in to reply to this topic.
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?