Yes bliss! My GF loved when I would go out dressed in public and would hint to people that I enjoyed dressing up 'too much' ! We spent three Halloween's together, my favorite being a female flight attendant (she was a pilot with stick on beard). Navy Blue pencil skirt, hose and heels, white blouse, matching tight navy jacket and bobbed wig. It was the best !
After I was divorced after 23 years of marriage, a girlfriend wanted me to dress as The Church Lady because she wanted to go as Ross Perot. I had never dressed before that and never even considered it. I reluctantly agreed to it just because I thought I needed to shake myself out of my male oriented opinion not to dress as anything on Halloween. I had to purchase a pair of size 10 red high heels and she provided everything else. I agreed to shave my mustache, legs and under-arms. We had great fun with her helping me while drinking wine and getting ready for the parties we were going to. When she finished my make-up and placed a wig on my head, she stood back from the mirror and exclaimed, "My God! You really are Glenda". I just stared at myself in disbelief and realized that there had always been a female side of me that I never knew of. At the parties we went to that night, all of our friends told me how naturally I had adopted a female persona. I haven't grown a mustache since that day and have come out to almost everyone I know since then.
Had many offers, passed on them all. regretted them all too. The first time I decided I wanted to go out, I did. My SO didn't help with anything (she was working) but was amazed at how well I did everything. Many years later I told her and have been enjoying Halloween ever since.
Flip Flops were made for Beaches & Bath Houses, We have neither in 2017. Lose the flip flops!
Many years ago when I was 25, I had a girlfriend who did not know that I liked to crossdress. We went to a bar for Halloween one night, me as the Joker and her as a hula dancer.
Then on the weekend we hosted a costume party. My girlfriend suggested that we trade costumes. So she dressed me as the hula dancer with her grass skirt, stuffed bra, and halter top. I had a blast! My brother noticed and said I was having TOO much fun. I wonder if he really suspected. It was such a fun night for me.
I dressed myself once long, long ago and my wife dressed me once long ago. This was back before I was really into crossdressing although I did sometimes wear a stuffed bra when nobody was around. Both times it was a "joke" and I wasn't intending on passing.
I wouldn't want to do it now because I would want to do my best and friends and acquaintances would easily figure out that I didn't just dress as a woman once a year. Now if I found a party where nobody knew me or my wife, it would be a different story. Krisi would make a public appearance for sure.
Krisi
Not for Halloween, but on a dinner cruise in Hawaii, of all the males, I was chosen to be a female hula dancer. We went below. After I took off my trousers and put on the grass skirt, two girls did the rest: stuffed bra, wig and lipstick. Back to the party, I hulaed as best I could, including tush wiggles, and butt bumps with the real hula girls. My wife took many photos. As a reward, our drinks were free. I stayed dressed until the cruise boat started back to port. I was a very closeted CD at the time and had a blast!!
No, never have . I believe I would thoroughly enjoy that experience.
As a youngster, I would pester my mother well in advance to help me create a Halloween costume. She knew I got a kick out of Halloween, and we both put a lot of time and energy into making my costume as good as it could be. At age 11, I found myself looking through a bunch of stuff in storage in preparation for Halloween. I came across boxes with some of my mother's clothes in them, and decided I would dress completely as a woman for Halloween. I bounced the idea off mom and she gave me a "let's see what we can do" reply. Her thinking at the time was once of doubt. "Really...you want to wear everything? she challenged. "Sure" I answered, "I want it right, don't want anyone to know who I am, that's the fun of it." As luck would have it a couple of her things didn't fit all that well and couldn't be easily altered. An aunt came to the rescue with those items. Between the two of them, I was given lessons in deportment, (keep your knees together when you sit, stoop don't bend over, etc.) and how to walk in somewhere between a 3 and 4 inch heel as I recall.
The following year was a first for me, I wore the same costume two years in a row. Well not exactly the same, we did make some changes as I had grown. At the end of that Halloween night however, my mother suggested that although I had great fun dressing like that, I was getting too old for Halloween, and that it would be best if I stopped dressing like that.
Karen
I think that would be every crossdresser's dream - to be "forced" to dress as a woman for a party.Originally Posted by Jenny22
Krisi
The party that my wife and I went to, I got this comment a lot. I found it personally very small minded and rude. It was accompanied by comments to my wife to "watch out, he might like this too much!" Really frosted me.
Other than a couple of small minds and a bunch of handsy guys, it was a spectacular evening though and I'd do it again in a heartbeat.
"Too much fun,what's that mean,
It's like too much money, there's no such thing."
-Tracy Bird
yes my mother did whan I was 9 and a couple of people thought I was a girl
Not since I was 11 years old. Though the wife and I have talked about it Kids take priority on Halloween
My very first time out dressed was after college, I was living in Tennessee. A volleyball playing girl friend of mine, Nita, wanted me to go to her Halloween work party with her as a Playboy Bunny. That's when I was young and skinny, and with a little beer, could be foolish.
She was tall, and her feet were pretty big, so she gave me a pair of blue Candies high heeled mule sandals that were on their way out. I cut the strap and laced some blue shoe laces through to make them a little wider, then wrapped the laces back around my ankles a few times before tying them. Having worn my mom's heels many times as a closeted high school cross dresser, they were actually very comfortable, and I was able to walk in them all night. (At one point later in the night, someone told me I could take off the shoes, but, NO WAY!) I've loved strappy heeled sandals ever since that night.
Nita bought me a blue leotard and tights and brought me a shoulder length brunette curly wig that matched the color of my hair perfectly. I cut up a white shirt to make my collar, cuffs, and bunny ears. The ears were made out of a coat hanger and other miscellaneous stuff to give the fit and strength. I bought a lacy apron to cover my other parts. I can't remember what I used for my puffy tail. (?)
I have such fond memories of sitting in her apartment dressed in my bunny outfit while she painted my nails and did my make up. Naturally, Nita went as Hugh Heffner (RIP) in jammies and a robe and slippers.
Why is the first time always the best? That was a great night. I spent much of it serving drinks, getting leering looks from the guys and jealous comments from the girls about my legs. Oh, and getting my ass pinched!
Years ago my then wife and I were invited to a neighborhood Halloween party. I was certainly a CD but early in my journey--owning no femme clothes and not out in the least. Brain storming ideas on the way home from a second unsuccessful costume hunting mall trip she, out-of-the-blue, suggested that I could dress as a woman. She saw a couple guys do this at a party a few years earlier (pre-marriage).
She worked Saturdays and I didn’t so that was my time to put together an outfit. Under the cover of Halloween I haunted the local thrift stores for the perfect “costume” trying on many looks in their terrifyingly not-so-private changing rooms. Thinking back, I had an amazing time and don’t remember any problems with the clerks or other shoppers. I finally settled on a red and white skirted, sleeveless majorette style uniform (yes a cliché by today’s standards) and red vinyl knee boots that were just out of style, so thrift store plentiful. I also purchased needed accessories—bra, panties, pantyhose and a thrift wig. I did all this with no previews and naively not expecting any problems.
The Saturday before the party I did the big reveal when she got home from work. I had even shaved my hairy legs and arms. I though I had made great choices and put in 100% effort but she just stood there in stunned silence. When she recovered she made it clear that I would not be wearing this costume as everyone (including her probably) would think I was gay. She didn’t consider for a second that I was just a crossdresser. Her idea of a man-in-a-dress costume was a flowered granny dress, rolled up shorts, hairy legs, red lips and tennis shoes. Not my look.
In order to make peace, I didn’t go as a majorette that year.
Last edited by Taylor186; 10-29-2017 at 08:52 AM. Reason: clarity, brevity
Not for Halloween but my sister had a Halloween themed wedding. My wife went as Charlie Sheen and I was the hooker. The girl that had been helping me with my makeup came over and worked her magic. As my wife looked on. she doesn't wear much makeup her self. I had a few people ask if my feet hurt in my boots? Being new they did so I did say yes. They would respond with oh good if they didn't I would have thought of you differently.All the clothes were mine since I have been on this journey for a long time. I loved being dressed but my wife wasn't thrilled with her costume. I would do it again in a hot min!!
Yes. My wife, who knows and supports my dressing. For several years, I off and on, dressed as a extravagant drag queen. A couple years ago, I/we decided to go for realism. Even though I have-an extensive wardrobe, we bought a beautiful black cocktail dress. We went the whole nine yards. Perfect makeup including false eyelashes, shaved legs, chest, armpits, hip pads, D cup bra, waist cincher, etc. I decided to wear my 3 inch heels...am still working on 4 “ 👠. I went in first and no one knew who I was. Loved it. Later, the wife of one of my friends told me how great I looked. I think (ESP) she sensed I didn’t get this way overnight. We’d all had cocktails and wine. She asked me if I’d chat with her....red light !!! I gave my wife all the credit...she didn’t buy it. Ha.
It was fun chatting with her about girly things. A week later, i bumped into her at the grocery store. She remarked again how pretty I looked. I just thanked her. As she left, she smiled and winked at me. I’m convinced she knows or highly suspects. I told my wife....no problem. Yes, I’ve worn the dress several times.
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