• This topic has 1 reply, 2 voices, and was last updated 7 years ago by Rose.
Viewing 1 reply thread
New Forums
  • Author
    Posts
    • #50774
      Anonymous

      The plans are set, Halloween out at a local club with a bunch of friends.

      With a month or so to plan my wife and I start talking about what our Halloween costumes will be, I knew what I wanted to dress as (to the nines in my best dress of-course) but with all our friends being there I knew that would be a mistake, like most I try my best to hide my feminine side from my friends and family except my wife of-course, she knows EVERYTHING about me and likes that I’m not the typical me Dick you Jane kind of guy.

      With the day quickly approaching I start stressing about what to wear and of-course my wife’s got her costume all figured out, It’s a smoking hot devil to angel costume, beautiful white corset, short little red skimpy tutu, white stockings with red bows on the top, big white angel wings with devil horns and a halo on top of her beautiful long red hair and to finish off the look sexy 5″ black high heels. I know I can’t top that and I’m super jealous of her outfit and how good she looks in it. Now I’m really stressed, what to wear, what to wear, sigh! I start to think of the cliche costumes to go with, Witch, Princess, Vampire Girl, Spider Queen with all these beautiful ideas racing through my head I just knew it was a bad idea to show how convincing I could be to all our friends. I know, I know it’s the one day of the year most people don’t bat an eye at some guy dressed as a girl for Halloween but again friends are involved here and I didn’t have the courage to go through with it.

      Two weeks to Halloween

      one night the wife and I sat down to watch some TV and we saw a commercial for the new season of American Horror Story and we started talking about how much we enjoyed watching the previous season called American Horror Story Hotel, we both had a favorite character from the show, hers being the Countess who was played by Lady Gaga and mine called Liz Taylor (Liz Taylor was a bald guy that booked into a hotel in NY for business but loved wearing makeup and dressing in women’s clothes and got caught doing it there, long story short he stayed at the hotel living out his dream of being dressed as a woman in a sense) I told my wife that I could easily pull that off and she responded with, you would nail that look and I can be the Countess and we can do the whole couples costume thing. I felt bad that she was about to change all the work she put into her smoking hot costume for me but I wasn’t passing this opportunity up and said totally!

      SOLD!

      For the next two weeks the wife and I scramble piecing our costumes together, Her’s was simple yet amazing looking, she bought a sexy white silky nighty that sat just above the knees and made it look just like the Countess’, she’s crafty like that, got some long fake nails and ordered a long blonde wig, black long silk gloves, 5″ inch black low cut boot/heels with black fishnet stockings, again making me jealous of her beauty once she tried it all on. Now on to my costume, I ordered a green long flowing silky nightgown, tight skinny leather pants, black fishnet shirt, my wife gave me a long tight black tank top with spaghetti straps to go under the shirt, gold dangling earrings, gold bracelets to match, long red glue on nails and of course we found the perfect pair of 5″ black opened toe high heels.

      Halloween is here

      I wanted my look to be flawless so the night before I completely shaved my head bald to match the character I was trying to portray. The next day the wife and I spent a good two hours getting ready helping each other with our makeup and outfits. With my green eye shadow, black eyeliner and red lipstick applied I take a look in the mirror to see a bald man dressed in women’s clothes with some flawless makeup and long red nails, my wife can’t believe her eyes as we both agreed that I could be a stand in for the character. Now it was time to go out into the world and that’s when the fear starts to set in, I can’t do this, everyone is so going to laugh at me but my wife assured me that she’ll be by my side and you got this not mention your look is killer (The things she does for me are beyond amazing, Love you honey).

      We walk out of the room to get the children ready to go to the grandparents house and they see us for the first time in our costumes and say to both of us, you look so pretty! I giggled at this one. We arrived at the parents house to drop of the kids, here was my first test, they laughed and we showed them a picture of who I was supposed to be and they said WOW it’s perfect. Of course I didn’t have the guts to go in there with my heels on, like most girls I brought a pair of flip flops to drive in.

      Off to the club we go, at this point I would bight my nails right off but I didn’t want to ruin my pretty nails. We arrive at the club and I tell my wife I’m wearing my flip flops instead, (I know, I know, coward!) we get out of the car and she says to me suck it up Sally, if I’m wearing them then so are you, time for you to see what we go through to look so damn good for guys, she had me there so on the heels went. We start are walk to the club from the parking lot which felt like the longest walk EVER, as we walk up the side of the building there is a window looking inside, I see that it is PACKED, my mind starts racing, run for the hills! My wife grabs my arm and tells me there’s nothing to be worried about and calms me down quickly (I could never do any of this without her) we round the corner to the entrance, deep breath and all of a sudden I hear this ohhh my god I love your guys costumes yelling out loud at us, well that quickly helped with my nerves. We walk into the club to meet up with our friends as we walk over to them I can see the expression on one of my family members face, it was of complete and utter disgust just shaking his head with embarrassment. I shook it off rather quickly as tons of people started coming up to me and telling me how perfect my costume was, of course a nice Martini helped take the edge off as well, most of my friends were pretty cool with it and just laughed and said no way you did nail it once they saw a picture of Liz Taylor.

      As time went I started to feel so comfortable and natural my wife even made a comment to me that I’ll never forget, She told me that I’ve never seen you look so happy and content before, she really couldn’t stop staring at me, she knew I was loving every minute of it. As the night progressed on people keep coming up to me and asking if they could take a picture with me, this blew my mind! My wife and I stepped outside for a quick break from the loud music, two ladies approached us and asked if we had entered the couples costume contest yet and we replied no, they said well we entered you both hope that’s okay, we laughed and said sure why not.

      As my wife and I walked back into the club we joked about how funny it would be to win the costume contest, we opened the doors and entered back into the packed club, about ten minutes go by and they announce that they will be doing the costume contest in a few minutes. At this point everyone is joking with us saying watch you guys win, I dismiss them all quickly, “tap, tap on the mic, time for the contest to begin” for some odd reason I just got like 500 butterflies in my stomach.

      First up is the couples contest, “lets have the Pirates couple up on stage, next the Facebook profile couple (my heart is racing now) and the Rum and Coke couple (whew, my butterflies are gone) and the winner is the Facebook couple. ”

      Next up was the women’s contest, they had a belly dancer, Adele from the song Hello and Alice in wonderland, you know the really skimpy hot version, and the winner is Adele, it was funny and cute.

      Now for the last one of the night the Men’s costume contest, “StarLord from Guardians of the Galaxy” which was my friend and I admit he did a really great job with his costume “next up is Jonathan from Hotel Transylvania” (which was a very clever costume) “last but not least the guy from American Horror Story Hotel” (wait WHAT, they can’t possible be talking about me) sure enough it’s me as my wife starts pushing me towards the stage go honey, the butterflies are back times 5000 now as I make my way to the stage, “drum-roll and the winner is! We have a tie between StarLord and the AHS Guy, sorry Jonathan” Is this really happening I thought to myself. “okay everyone we need to have a tie breaker, we want everyone in the club to cheer their loudest for their favorite and we’ll base the winner off your reaction” “StarLord” Crowds roars! “AHS Guy” Crowd cheers about the same, “this is a tough one to call, one more time, StarLord” Crowd Roars louder, “AHS Guy”, CROWD ROARS INSANELY LOUD THIS TIME it’s like the whole club is cheering for me “and the winner is American Horror Story guy”. At this point I am so caught up in the moment of what just happened I can only cheer, laugh and smile. I just freaking won the men’s contest basically dressed as women the only thing I was missing was a wig, the prize was nothing special just an ordinary bottle of cheep wine, but let me tell you, it was the best tasting wine I have EVER drank, it was like drinking victory in every glass and what girl doesn’t enjoy a nice glass of wine.

      The night continued on with my wife and I dancing the night away while taking the occasional photo with a random couple.

      As we left the club that night my wife told me that she was super jealous that I won (hehe, shes jealous of me now).

      I will say one of the best parts was watching my cousins reaction to me winning the contest, I think at that point he knew he had to swallow his pride and give me props on the costume, why not everyone else in the club did.

    • #50785
      Rose
      Lady

      Wow, what a story Mason!

Viewing 1 reply thread
  • The forum ‘Personal Crossdressing Stories’ is closed to new topics and replies.
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?