I work in an office environment and several years ago it was decided we would all dress for Halloween. I procrastinated on purpose so I had little chance to come up with a costume and could convince my wife to let me dress as a woman. We decided I could go as Ragetty Ann. I underdressed in bra, panties, and pantyhose. My wife said she never saw a Ragetty Ann with breasts but I convinced her to let me pad my bra. I wore a semi-sheet white blouse underneath a navy blue jumper I borrowed from my wife. I wore white knee socks and black Mary Jane heels. My wife helped me style a wig with pigtails and she advised me on my makeup. She said I looked cute for a last minute costume. I was one of three men in the office and the youngest. There were about a dozen women in the office with three of them about my age. When I arrived at work they couldn’t believe I would dress up like a girl. Everyone paid me compliments and I was soon invited to join the three younger women for lunch. I had such a good time that day. At lunch the other girls asked me lots of questions. They were so curious. They never came out and asked if I was a cross dresser and I never told them I was. But I never told them I wasn’t and I’m sure if they used their female intuition and read between the lines they had a pretty good idea I enjoy dressing as a female. A couple of years later I dressed as Little Bo Peep and by then I’m sure they had no doubt but I never confirmed their suspicions.
Reply To: Have you ever dared telling someone at work about your cross dressing?
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