It Happened To A Friend Of MineThis is a true story, but it's not about me. My mother may have suspected I had dressed up in her clothes, but she never caught me at it. Someone I know, a friend of mine shared a story with me about getting caught, and I would like to share it with you.
My friend Carrie is a crossdresser, and like so many of us, began experimenting with her mother's clothing at a fairly early age. Carrie was an only child and grew up living with her mother. There was no male presence in the home. Carrie's mother was a successful professional, made a very good living financially, and really dressed up to the nines. Because she had a good income, Carrie's mother had a lot a very nice, and rather expensive clothes.
Carrie grew up with around a very attractive mother who owned many designer suits, dresses, skirts, high heels, lingerie, etc. She was always dressed to the nines. Carrie's mom has gorgeous legs and always wore stockings or pantyhose, and sexy high heels. When Carrie was very young, she would often feel her mother's stockinged legs, and would put her head on her mother's lap while watching television. Carrie always seemed to appreciate her mom's clothes. As Carrie and her mom look back, the crossdressing was probably inevitable.
Carrie also found her mother to be gorgeous. I know that it's difficult enough to have a thing for wearing your mother's clothing, but then imagine being attracted to her as well.
When Carrie was 13, she waited until her mom had left the house for work. Carrie went ahead and put on one of her mom's finest skirt suits, along with a blouse, bra, panties, skip, garter belt, stockings and stiletto heels. And like so many crossdressers, once she got all dressed up, started to go about doing things around the house, enjoying the look and the feel of wearing women's fine clothing. She was playing piano, and didn't hear the door open.
Her mom was supposed to be at work, but for some reason, came home much earlier. Looking for her son, and hearing the piano, she walked into the living room. Low and behold, there was Carrie all dressed up, sitting there playing piano. The skirt was up around Carrie's waist, and her erection was exposed. Carrie's mom gasped. Carrie looked up and her heart nearly stopped. Before her mother could say anything, Carrie began crying.
I think this is every crossdressers biggest fear, being caught by mom or sis while wearing their clothes. As Carrie broke down, her mother quickly realized what was happening. Her son was a crossdresser, and she had caught her "in the act" so to speak.
Her mother's attitude immediately shifted from being shocked, to being motherly.
Carrie's mom knew that crossdressing was not that uncommon, and that Carrie needed someone who was understanding.
Carrie's mother sat down on the couch to comfort her son. As Carrie cried, her mother pulled her in closely, telling her that it was OK. Carrie held her mom tightly. Her mother has very nice sexy breasts, and Carrie's face was buried in her mother's blouse up against those lovely breasts. Carrie could also smell her mother's wonderful perfume, which made her smell so feminine. Carrie began to relax. She realized her mother was not going to go ballistic on her. Her mother held her, and rocked her back and forth, trying to comfort her.
But the feel of her mother's breasts against her face and the smell of the perfume also created a sense of arousal. Carrie's legs were brushing against her mother's stocking covered legs, creating a rather electrifying sensation for Carrie. As Carrie held on to her mom, her erection rubbed up against her mother's stockinged legs.
It was not intentional. It happened totally by accident. But all of the sensations were too much for Carrie. She became overly excited, and climaxed by ******* all over her mother's legs and skirt. This made her cry even more. Her mother knew how embarrassing this was for Carrie and just told her not to worry about it.
Carrie's mother gave Carrie complete access to her wardrobe. Carrie could wear anything she wants.
All this happened years ago, and I no longer keep in contact with Carrie, but I always thought she was very lucky!
BizSuitStacy 46-50, T 20 Responses 27 Dec 5, 2010