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View Full Version : Halloween dress, a first for me.



insearchofme
10-26-2006, 04:30 PM
Due to my job I am almost never at home for the Trick or Treaters. After many years of answering the door by herself my wife has just turned off the lights and we've had no children come to the door. A few families have moved into the neighborhood (one is right next door, with two cute kids) and I know that this year we'll have to give out treats. I'm going to be home and told my wife I'd do the duty.

Last night I said I wanted to wear a costume and from the other room I heard her say "Why don't you dress as a cheerleader?" Now she knows and tolerates me wearing panties (we both wear size 7 but fill them out differently)but she doesn't know about my desire to CD. She still thinks, even though I've told her no, that CDs are all gay. One time she was going shopping for panties and asked if I needed any? I said she could pick me up a few pair and if she saw any bra and panties sets in my size she couild pick them up. In a VERY cold tone of voice she said, "Why would I want to see you in a bra?" I told her I was just kidding, I know when to take a step back.

Well this time I said OK but I wouldn't know where to get a costume. She said to go to Goodwill. I said alright I will. So this afternoon I drove to a Goodwill about 10 miles from here. I went in and told a young lady (19 or 20) what I was looking for. She said they didn't have any but we might be able to put something together. She took me up and down rows of shirts and tops. It was a lot of fun ( she really seemed to get into it)but alas there was nothing. I said I could maybe go as a bride or a vampire in a black dress. So off we went. Again there was nothing in my size. We also went and looked at shoes in case I found something elsewhere. Again no luck. She did tell me where another Goodwill was that wasn't too far. I asked about consignment stores but she didn't know of any near by.

So I drove to the other one and again found a SA and she said they probably had nothing on the cheerleading costume but they had plenty of bridal gown and bridesmaids dresses. I had decided that I was now going to go as the Fairy Godmother if I could find the right dress.

We went over and only found a bridesmaid's dress in a 5X. Now I'm a big guy but that looked too big even for me. So I asked her if she thought it's fit. She said go try it on. Off I went and while it was loose around the waist it did fit in the shoulders. I went out and a customer around my age looked up and said "Did it fit?" I said it did but now I need shoes. We were close to the rack and she helped me look for shoes. She was having fun and was very sweet to me. We didn't find any shoes so I put the dress back and went to the SA and told her I'd have to find some shoes and if I did I'd be back. She told me about a Pay Less about a 1/4 mile away so I went there.

I didn't want to spend much money so my wife wouldn't freak so I was thinking I might not be able to get the dress. I went in and told the manager what I wanted and my size. She asked what color the dress was (pink) and we looked at several shoes in my size. She left to take care of some other customers and I tried on quite a few pair. I told her that comfort was more important than color and she agreed so I got a black pair that was open on the heel. The heel is 2" so I can walk in them fine. Also my wife is pretty fashion conscious so she may make me take them back and get another pair, they do have a sale, the second pair for half price so she may be up for it. The manager and I chatted about her going to a party dressed as a flapper and I thought she'd look great since she was a good looking woman. Boy did I say the right thing! She really brightened up and even threw in 3 pair of knee highs. If I was single....

I drove back to Goodwill told the SA I had the shoes and now all I needed was a bra. I told her my measurements and she took me to the bra rack and I started looking (they were not in any order) I finally found a cotton white front hook soft cup in a 42 B. The SA was near by and asked if i had found anything yet. I showed her the bra and I asked that since it was already a bit streched out did she think it would fit? She said there was a good chance. I asked her if it would keep any "stuffing" in. She said that since I'm big through the chest it probably would. So off I went to the dressing room with the bra and dress. I had to make sure my bra straps wouldn't show since my neckline drops down a bit (not enough to show any cleavage, darn it!). The bra fit and the straps didn't show. I told the SA we had success and went to pay for it. I also mentioned that thanks to weight lifting I almost filled in the cup naturally. she said my wife would be very proud and laughed. While standing in line a couple of women said they thought the dress was pretty and asked what was I going as. I told them and they said the dress was the right choice. That made me feel pretty good.

Just before I started writing this my wife called on the phone. She's gong to have her hair done and we talked about dinner. I said, "Oh by the way I got my Halloween costume". there was silence on the line and then she said. "You did?" I said yes you told me to go and get one last night." She said that she was just kidding. I told her that I thought she was sreious and I decided to have some fun with it. She then laughed and said you know you're the on that has to open the door. I also told her I was going to have to borrow some things and she laughed again.I also asked if she wanted me to wear it when she got home or just show it to her. She said just show it to me.

One of the things I'm going to have to borrow is one of her mother's wigs. I haven't seen any of them so this might be a bit of a risk. I'll write tomorrow and let you know my wife's reaction. This may be the start of something good or it might be a big mistake.

Sorry this is so long, wish me luck.

jessikasummerfox
10-26-2006, 05:58 PM
Okay...good luck, but it sounds like you've already had a lot with meeting a super-helpful SA though. I can't wait to hear more.

Ibuki_Warpetal
10-26-2006, 06:07 PM
That's a very confidence-inspiring story.
Kinda makes me want to go do the same. (x

NatashaWI
10-26-2006, 06:08 PM
Good luck Dana - your outfit sounds adorable. Will you be able to find some nice pantyhose and jewelry to help make the costume even more complete? How about makeup? I hope your SO will support you in getting fully girled-out.

Have a wonderful time. Halloween is a great outlet for us!

Natasha

Methos
10-26-2006, 06:13 PM
congrats sounds like you had a good time and hope to hear that the wife is cool with it also

MJ
10-26-2006, 07:32 PM
well you are on your way.. the problem is to inter-grate this in to cross dressing with your SO approval.. so think about it i hope it works out well for you .. hugs

Karren H
10-27-2006, 08:21 AM
All right Dana!! That's soooo cool!! You lucky girl!! You had better take some photos !! Maybe I'll have to dress up and come trick or treating at your house!! Hehehe. But I gget to try to pass as the male handing out candy this year! Again....

Love Karren

uknowhoo
10-27-2006, 08:31 AM
She then laughed and said you know you're the on that has to open the door.

Quite the double entendre!!!

Good luck, and keep us posted. ;)

Patty
10-27-2006, 08:58 AM
Have fun!!
Love reading about good sa experences.

Angie G
10-27-2006, 09:10 AM
Hi Dana good luck with the wife hope shelightens up on you I dress around the house the wife knows and is there A few weeks ago she told we I should dress for Halloween I go out with my grandkid trict or treating it my first time others will see me, i cant pass so it's all in fun they don't know I dress at home so hurry Halloween :hugs:
Angie

Daphne Renee
10-27-2006, 10:02 AM
congrats.. I must be going to the wrong goodwill stores.. thats never happend to me.. but I am glad you had such a great time.

insearchofme
10-27-2006, 10:17 AM
Now the rest of the story....

When my wife got home from the hairdressers I helped her fix dinner (we both like to cook). We talked about her day and a few other trivial things. Finally I asked if she wanted to hear about my shopping? She laughed and said go ahead. I told her all about it and she was laughing all the way through it. From her reaction I felt that I should play up the humor in it.

While at dinner I asked if she thought I could borrow one of her mother's wigs. She'd said she would call her. I then asked her if she had any clip on earrings and she said no but she knew my sister did. Later she called her mother and asked about the wig and she and mom had a great laugh. Her mom said she had 3 wigs but they were all white but I could borrow one. We're taking her to dinner tonight so afterward I'll go try them on. My wife also told me she had a magic wand she used in school for her students and it would light up when you waved it, that'll be cool. I showed her the dress, shoes and bra after dinner but she didn't want me to dress for her. She said her sides already hurt too much from laughing. i was dissapointed.

I called my sister and told her about what I was doing and she was really fired up about it. She said come over on Saturday and she and my niece would help me pick out some. She also said she had a princess crown or tiara I could wear. She also asked if I remembered when I was about 12 or so and I dressed up with her and some of her friends. She said my mom said that I would have made a pretty girl. My sister said that I told her if she ever told anyone else I'd whip her. Well I did remember but told her I didn't. I also said that we'd find out if I'd make a pretty woman (believe me I won't!)

My wife called out and said that we'd take pictures. Now that is something I wanted to do but I was wondering how I'd get her to do it. I asked her later if she'd take the dress in for me. She said she'd pin it up for me. While I was on a roll I also asked if she'd show me how to do makeup since she might not be home when the kids started coming. She said sure.

So far so good. I've been in my shoes ever since my wife left for work, just to get used to them, it really isn't that hard when you're motivated. I'm also in my bra just because it feels so good to wear it. I'll probably put on my dress again later also.

MJ you're right the tricky part is going to be to get her to be ok for me to increase my CDing. I'm going to go slow and try to think this through. Thanks for all you girl's kind words. I'll keep you updated.

Emily Ann Brown
10-27-2006, 11:31 AM
Dana hun,

There is no trick to getting to increase your CDing. My wife will let me dress all I want....just as soon as I move out and sign it all over to her. I'm thinking............

Emily ann

MJ
10-27-2006, 11:42 AM
hi Emily

it is sad if it comes to that. but lets face it there are a lot of gg who will never accept there mans cding.. cant you try and talk to her there must be a way its just sad i wish you well .. hugs

insearchofme
10-27-2006, 01:30 PM
I am afraid that my wife's reaction will be the same as Em's wife. Even if it is I always have memories of this week.

PS
I'm sitting in my dress and heels wearing lip stick and some mascara. I really feel good right now!

paulaN
10-27-2006, 02:37 PM
Your on a roll for this holloween. I am glad you are having such a great time with this. I know I would be. Savor the moment for it may be a long time befor you get to do any thing like this again. Unless this opens the door to acceptance, I hope so.

insearchofme
10-30-2006, 10:39 AM
It's time to update you on what's transpired since I last wrote. On Friday we took my wife's mother to dinner after her hair appointment. They stopped by the house to pick me up and I showed her my dress, she said it was "beautiful", I looked at my wife and we laughed, after all my mother-in-law is in her late 80's. After dinner we stopped by her house and picked up one of her wigs. It's an Ava Gabor style. I think it's a little short for me but what the heck.

On Saturday I went to my sister's to pick up some clip on earrings. She only had one pair, they're a bit small, I was hoping for dangly, but they will go with the dress. It's seems that my niece who's in high school was really getting off on this. I took my wig and she styled it for me. it's a good thing since at first they both said I looked like George Washington (not a look I want). My niece also got my a tiara to wear. She offfered to come over and help me with my make up on Tuesday. She wanted to come over with one of her freinds but I said she should come over by herself.

Later when we were alone I asked my sister about my dressing when I was younger. She told me all about it (it filled in some of the blanks in my memery of that event), I asked her if I had fun and she said definately. I then told her that I may be a repressed crossdresser since I was having a good time right now. Sher said matter of factly that I may very well be one. I told her laughlingly that my wife may be calling her about it one of theses days.

Yesterday my wife said she'd take in the dress for me if it needed it. Before she started my sister dropped by to leave some things with us. I showed her the dress and she said the it was really beautiful, I asked if she meant it and she said she did. After she left I asked my wife and she said it really was pretty even though she wouldn't wear that style. I tried it on for her and she laughed a bit, I thought it need taking in and she said well we need to see it with me having boobs so I went and got my bra. She kind of looked at me funny when I put the bra on, I'm not sure she liked it too much. She then had me stuff it with some white socks. She said I didn't need too much since my pecs filled most of it up. She said that it really was ok but I told her I thought it made me look fat, at that she really laughed and said ok. She gave me a half slip that she said I needed since you could see my panties though the dress. It was a bit tight but it gave the dress a much better look.

I took the dress off and was just standing in front of her and she said hastely to ge those things off. I pulled off the slip and while I was standing in front of her in just a bra and panties she said, "It's looks like you're really enjoying this, you may have to wear a jock strap!" I laughed and said I don't own one but I was enjoying it. I offered to let her take care of things but she said get those things off! I really took my time taking the bra off. I removed one sock and then the other and rolled them together wearing my bra as long as I possibly could. I really wished I could have worn it the rest of the day.

She's going to help me with the make up but I'll probably have to wait until Tuesday. This is going to be fun and I'm taking a lot of mental notes of her reactions so I'll be prepared to convince her "let" me take this crossdressing to another level. I am going to take this slowly but I am so excited about it.

Sorry for the length and hopefully I'm not boring you girls.

uknowhoo
10-30-2006, 09:29 PM
It's the most... wonderful time... of the year!!

Great news Dana, that the rest of your family is so enjoying this with you. It sounds like you may have a confidant in your sister, and that's a verrry good thing! Your wife asking you to get out of the femme apparel so quickly is not quite so encouraging a sign though. But what counts right now is tomorrow! I'm sure you'll have a wonderful time, and with the perfect "excuse" too. Savor this while you can, sweetie... AND DON"T FORGET THE PICS!

xoxo

Tammi

insearchofme
10-31-2006, 09:07 AM
Tammi

I agree with you that asking me to get out of the dress so quickly is not good.

This morning she showed me what makeup of hers I could use and showed me how to put it on. She wants me to not use a lot, just some blush, eye shadow, mascara and lip stick. I am going to paint my nails and we'll see what she says.

I'm practicing with the makeup now and think I need a darker shade of lip stick since I have thin lips and the pink just seems not to show up. I am sooo excited about today.

Wire Road
10-31-2006, 09:40 AM
I agree with you that asking me to get out of the dress so quickly is not good.
This morning she showed me what makeup of hers I could use and showed me how to put it on. She wants me to not use a lot, just some blush, eye shadow, mascara and lip stick. I am going to paint my nails and we'll see what she says.
I'm practicing with the makeup now and think I need a darker shade of lip stick since I have thin lips and the pink just seems not to show up. I am sooo excited about today.

and youre doing all this just to pass out candy to a few kids?
I hope I'm wrong but I can see this going bad for you and you getting into an argument with your wife.

insearchofme
11-01-2006, 09:46 AM
Last night was a really fun time for me. I got dressed after dinner doing my own makeup, my wife added some more blush. She didn't have any lipstick that was really dark enough but that was OK. She pinned my dress so it wasn't as baggy around the middle. She then put the wig on and styled it. She also gave me a strand of her pearls. I was set!

My sister and her daughter came over on their way to a friends home and we took some pics. When my sister saw me said that I kind of looked like her. My wife and niece agreed, I feel sorry for my sister! She also said she really liked my shoes and where did I get them? I said if they fit her she could have them but she wears a size 10 and I wear an 11. We had a lot of fun taking pics, but the roll of film had 24 exposures and my wife only took eight so who knows how long it'll be untill I get to see them. My sister took some on her camera so hopefully I'll get to see them soon.

It was a lot of fun passing out treats to the kids. I wish you could have seen their faces when I opened the door and said "Trick or Treat", some of them were priceless. The first groups of kids had their mothers standing off on the street. When I opened the door and the mothers started laughing, one yelled that I looked hot, it was dark and I'm sure she needed glasses. A father came to the door with his little girls and when he saw me said "Bitchin!" and called for his wife to come look at me. He said that it was pretty cool! A two teen girls brough their little sister and they were all dressed, they thought it was fun and I said that I bet I was the best looking Fairy Godmother they saw tonight. They giggled and said I was the only one they saw.

I only had 2 negative reactions, one was a preteen boy who couldn't wait to get his treats and leave (I thought he was a bit old for Trick or Treating). Another was a mom who was dressed as a vampire who hustled her daughters away as fast as possible. The funny thing was that her husband thought it was pretty funny.

At one time my wife and I were sitting talking between Trick or Treaters and I looked at her and said, "You pretty much hate this that I'm sitting here all dressed up." This was based on some of her reactions to my enthusiam. She said she really didn't like it. I acted a bit too serious a couple of times on purpose just to see how she'd react. For instance she didn't want me to put on nail polish. She thought that was too femme. She wanted me to play this for laughs only.

I know now that she probably will react very negatively if I want to increase my dressing. So I'm going to proceeed with extreme caution. What the heck I'll always have memories of last night and she said we should save the dress, shoes and bra. So I may do this next year.

All in all it was fun, and wait until next year!

Karren H
11-01-2006, 10:12 AM
What an adventure, Dana!!! I'm really glad you got to pull that off.. Lucky girl!! Hope things continue to roll your way!!

Can't wait to see the photos!!!

And you never know......next time I'm out your way maybe we can go out shopping enfemme, your getting to be a quite a pro!! .....barring another huricane that is. Hehehe

Love Karren

Charleen
11-01-2006, 10:40 AM
Good for you girl! I got dressed last nite myself,see my thread, and had a blast.
I can relate to your situation with the wife. I hid for our 30 years together. She was more important to me than dressing.
On the up side, you have a bra now! Enjoy! But be careful.
Love and xxxx, Lily

insearchofme
11-01-2006, 03:29 PM
Lily

Thanks for your encourgaing words, I did read your thread and it was great. I've been hiding this from my wife for almost 40 years and would really like to "come clean" but as you said she is much more important to me than dressing. As far as having a bra, yippppppie!

Karren

You're the ultimate pro, I knee in homage to your skill and nerve!!!!

MJ
11-01-2006, 06:11 PM
wow i am glad you had a good time. you know once you start !!! i hope you get your dream just find a way take it slow . thank you i enjoyed you story ..
please keep us informed
oh Karen love your avatar would you like to come to Hamilton Canada and I will teach you how to play hockey ... :D :devil: