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I grew up in a small town. As a young boy I discovered that I really liked wearing a bra. I tried one on as well as a dress during a dress up game. This was due to a dare. I was about five or six at the time.whe I looked down at my chest I thought this is so cool I look like I have boobs. For some reason that thought really felt good. I quickly escalated to wearing young women’s clothes whenever I could. I found that I really enjoyed it. However, I always knew I was male when dressed as a woman.
I never really went all out in my cross-dressing as a kid or even as a teen. By that I mean no total dressing with makeup or in any presenting completely feminine. On the many Halloweens that I participated in as a young boy I saw other boys dressed as girls or woman. I was always jealous of them because I didn’t have the courage to dress as a girl that Halloween. I knew that I really wanted to. Maybe I was afraid that I would not look pretty or look too pretty while doing so. I didn’t want my friends to know how much I enjoyed wearing bras, stockings pantyhose, skirts, tops, and dresses. I didn’t think I could hide my feelings about loving being dressed that way if I did.
Life went on I continued to cross dress in my private moments if I could. As I grew older I noticed that my desire to dress as a woman had not faded. Eventually I married; and yes she knew about my dressing habits before our wedding. I told her about it and she seemed to understand. I hind sight I think I either failed a telling her how much I liked it. Or she didn’t get it. Now my wife varies between not approving and approving of this activity. During most of our marriage I really didn’t dress much until I was laid off.
An opportunity fully dress up came shortly after my first Halloween when I was laid off. I recognized the opportunity, seized it and. I choose to dress totally as a woman. It started after I had shaved of my mustache for a mock job interview. I came home and was alone in the house and I started dig my chores. While I was doing the laundry, I was folding the clean clothes. I took a bra off the hanger and thought ‘why not dress up?’ Then I just slipped my arms into the straps and fastened it on. My next thought was there is some cotton webs in the Halloween box that would fill out these cups. I finished folding the laundry.
Then I went to the costume box to get the cotton. I saw the wig that was left over from an Ozzy costume and I thought; “There is a wig and cotton, in the Goodwill box there is a skirt or two plus some tops. Maybe I can try to find some pantyhose and shoes too. I gathered everything up, went upstairs and found some pantyhose and sandals. Within a few minutes I was fully dress in women’s clothes.
I check myself out in my bathroom mirror. I thought I looked pretty good I put on the wig. Then wow, something happened when I saw myself looking more like a woman than I had ever seen. Then thought cane to me, “How about some makeup?” I went to the closet and grabbed the tray and watched a YouTube video and then thought, “’I’m doing it!”
So for the next thirty minutes I did my best to apply makeup. I did ok. I looked and saw myself completely dressed as a woman. My body was roughly hour glass. My wig was OK. My make was OK. However the sum total of those parts was an image that, in m eyes no longer looked like me, but a stranger. That stranger looked to me just like a Latino woman.
I was wearing a black dress from the Goodwill box, the black Ozzy wig, a white size 40 DDD Bali flower Bra stuffed out with cotton. My breasts did look more like a size H! Also I wore a black belt for the illusion of a woman’s waist, a pair of tan pantyhose, and black sandals. My makeup looked good enough to give the illusion of a Latino woman.
That day for the first time I saw in the mirror a woman image that did not remotely look like me in a dress. I thought that with some practice I might even be able to look more presentable. This dressing up went on for a while with some improvements and some mistakes and lessons learned. One of the most important lessons learned was me not wearing any of my wife’s clothes. After having some discussions with her about how wearing her clothes I decided I would get some female clothing. It occurred to me that doing so around Halloween would not arouse any suspicions about me being a CD.
In the meantime I had found a part time job and had been doing it for nearly five years. I thought my dressing skills had improved. Now I was only dressing in clothing that was rescued from the Goodwill. One year, three days before Halloween, I went to a thrift store to just browse the selection of women’s clothes. I was toying with the idea of cross dressing on Halloween so I thought may I would find an out fit. As I was browsing through the costume section a female sales associate came up to me. Her name may have been Linda. Then she asked what kind of costume I was interested in. I answered quite to my surprise that I wanted to dress as a sexy secretary for a party.
She said, “OK the. I can help you. Let’s see what I have here.” So within ten minutes she had picked out a black skirt, two floral printed tops, a bra, pantyhose, a pair of black heels, a blonde wig, and a red and black bodycon dress. She then directed me to a dressing room where I tried on everything. When I walked out she asked what outfit I wanted, I said “I can’t decide I like them all.” She smiled and gave me a bag. Apparently there was a bag sale that day fill up a bag with ‘create your own costumes’ supplies for $20. She asked me if I want anything else and we filled the bag.
On Halloween I had the day off. The Kids were at school. I gathered my new outfit, wig than got my padding, homemade breast forms and other items I thought I was going to need today. I stared to dress; I put on my undergarments then I padded my form into an hourglass shape. Then I dressed in my new outfit oce I was done I thought I looked great from the neck down.
Next I did my makeup as carefully as I knew how. I added my accessories, ear rings bracelets, a watch and a necklace. I opened my new blonde wig put it on, brushed it. Then I looked myself over, I saw a tall thin, yet curvy buxom blonde woman staring back at me. She/I was smiling with delight! I knew I had done it achieved the goal of looking like a woman. I was blown away a how good I looked. I looked like a thin busty blonde attractive blonde MILF.
I felt brave so I went out and grabbed the mail in broad daylight while dressed as a woman. While I walked to the mailbox and back I thought I looked so good that the idea of going back to the thrift store to thank the woman who helped me pick out the clothes. I was wearing. I put the mail on the kitchen table. Then I got my purse. I put my keys, wallet, phone, and mini makeup kit in it. I went back out and got in my car and drove to the thrift store.
I walked in and looked around for a minute, I didn’t see her. An associate came and asked me “Can I help you ma’am?” I was floored she called ma’am!. I told her that I wanted to thank the other woman Linda for helping me with my costume. She said she would but she wasn’t here today. Then she asked me, “What is the costume I was going to wear to your party tonight?” I told that I was wearing my costume and that I was a guy dressed as a sexy secretary.
She was shocked and told me that she would have never guessed. She also mentioned that my wife or ‘who ever’ did my make up I had done a great job. Your eyes, lips, and foundation are perfect! Your boobs look so natural! Not like most guys when the do drag for Halloween. “She called over her three other coworkers to check out my costume, my makeup and padding. I thanked them for the compliments and then left the store.
As I left the store I heard them say, “There is no way he hasn’t done this before!” The second one “He is a full fledged cross dresser.” The manager lady said “He looked too good! He has defiantly done this before!” The last one said, “I hate it when guys look better in a dress than I do! It isn’t fair! ” The first said, “He is walking in those high heels like a pro!” I thought Wow they think I am good at this!
On my way out a couple walked in, the guy opened the door and held it for me, and then the woman remarked “Your ear rings are lovely”. I was happy because my first time out dressed and I passed. I took some pictures of me in my costume when I got home. I looked good!
Over the years following I would like to think I’ve gone from just passing to being completely passing as a woman. Now I dress in my own clothing with a store purchased butt shaper, a corset and real breast forms. I’ve gotten better at makeup and even wear a quality wig. I think that now I can present a fairly good illusion of a woman; albeit a tall woman.
I truly love dressing in women’s clothes, yet I have no desire to be anything other than a man. My temporary expression of a woman feels good to me. Cross-dressing is more like a fun hobby lifestyle than anything else. My posts are true but the names have been changed to protect the innocent.
Thanks for sharing your wonderful story. I really enjoyed it. As I’m reading through, I can relate similar experiences I have had. it brings back the feelings I had when I did them, like seeing myself fully femme in the mirror the first time, going out to get the mail or walking to the car, and going shopping.
The excitement, thrill and rush is incredible. I can only get that from dressing and going out. There is nothing else like it.
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