Mother Son Crossdressing Stories
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Published May 27, 1998 5:10PM (EDT)
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M y son is a cross-dresser. Most mornings he gets up, puts on a hand-me-down dress stolen from his sister, wraps an old white pillowcase around his head with a ribbon (his "long blond hair") and prances around singing, "The hills are alive with the sound of music." My son is 3 and a half years old.
At the toy store, he does not want Batman. "I want a Batgirl doll," he cries. When he begs to play with his friend Margo, it is not because he likes her better than his best friends Billy and Andrew; she just has more to offer -- like an extensive collection of Barbie dolls and a whole wardrobe of little clothes he can dress them in.
He loves preschool -- partly for the teachers, somewhat for the other children, but mostly for its wonderful selection of tutus, fancy party shoes and pretend jewelry. His grandmother (my mother) received the shock of her life when she went to pick him up one day and he was wearing a blue tutu with beaded gold slippers. The other mothers laugh and tell me he is such a thespian. The teacher tells my husband and me that he is "highly in touch with his feminine side."
If we only had to worry about preschool, life would be fine -- but his grandparents (on both sides), his aunts and uncles, his baby sitter and just about everybody else are up in arms. "Boys should be playing baseball, not Barbie," my mother-in-law exclaims. "I was so embarrassed," complains my mother after the harrowing tutu incident. "He keeps taking my daughter's Cinderella slippers!" my neighbor told my other neighbor who told me. The older siblings of his friends have called him an oddball, a weirdo and generally not normal. Adults tend to be more subtle with questions like: "So when do you think he will grow out of it?" or "How does your husband feel about it?"
I have tried to explain to each of them that my son approaches life with a unique flair. While he loves soccer, he often plays it wearing a silk cape that flutters in the wind when he runs. Playing with his cars takes on new dimensions when he acts out both the "damsel in distress" and the "sheriff to the rescue" role, alternating hats to represent each character. My husband can't wait for Little League to start because he sees a little slugger in our son who can already hit the ball out of our relatively large backyard. Our son also can't wait to play baseball, but for a different reason: He says that cleats "are just like tap shoes."
Thankfully his preschool teacher has assured us that he is simply "evolved." "I wish all of my children were as well-balanced as your little boy," she told us at our first parent-teacher conference. "I love the way he plays cowboys and Indians wearing his favorite ballet slippers." She credits our "nonjudgmental and accepting parenting" for his creative expression. Frankly, I was a little relieved. So he is not a weirdo -- he is "evolved." I wish I could take credit for this, but it is all of his own creation.
Interestingly, no one seems the least bit disturbed about our friend (I will call her Gillian). At 5 and a half years old, she refuses to wear dresses, plays T-ball and soccer and is proving quite skilled at climbing trees. She has more cuts and bruises as a result of roughhousing with her older brothers than my husband claims he ever received playing varsity college football. Gillian, I am told, is a tomboy. "Isn't she cute," a friend exclaimed to me when we were at Gillian's house for a Sunday barbecue. (My son was inside watching "Pocahontas" with two girls.) And my son is not cute when he dresses up and reenacts the glass slipper scene from "Cinderella"?
If Gillian is a tomboy because she likes to do boylike things, what then is my son who likes to do girl-like things -- a janegirl? As far as I can tell there is no equivalent in the English language (at least there is not one in my Webster's Dictionary). More important, there is no acceptable behavioral equivalent.
I have begun to ask myself what is normal? My son loves trucks, cars and trains. He plays for hours with his Brio train set while wearing his sister's striped dress. He is very affectionate and will frequently tell his friends he loves them with a hug. Last fall, during those terrible twos, he was accused of being a bully because he bit a girl at the playground. How can a child go from bully to sissy in a mere nine months?
I am coming to realize that while our sex-role stereotypes have expanded for girls, they have not for boys; there seems to be no acceptable cross-gender equivalent. A gay friend of mine claims all of the uproar is a homophobic response to my son's actions. "I remember loving to dress up and put on makeup, too," my friend tells me with a knowing glance. He is only 3 and a half years old, I remind my friend -- a little early to be defining his sexual preferences.
The feminist revolution appears to have successfully helped foster an environment that makes it "cool" to be a girl. Much research is being done to ensure that girls are encouraged to excel in math and science, overcome the repression of adolescence and, with luck, one day be more than tokens on boards of directors across the land. I am thrilled. Trust me; I have a 1-year-old daughter. I want her to understand and respect her power, her opportunity, her femaleness. But what about my son? I would like him to be able to respect his power, his opportunity and his maleness even as he explores his feminine side.
It's not just in my house that the days of "boys will be boys" are over. A few months ago, the Wall Street Journal ran an article that claimed prescriptions for Ritalin were at an all-time high and increasingly, boys are expected to be less rambunctious and more docile (that is, more girl-like). And a guest commentator on an NPR program about youth violence expressed concern that the rise in the births of boys would result in a coming "deluge of testosterone-laden young men" creating havoc in our society. My mind reels: Is the conclusion that a 3-and-a-half-year-old should be more like a boy but a 12-year-old should be more like a girl?
I have to admit, sometimes I am embarrassed by my son's behavior. His declaration to my father-in-law that he wants to be a ballet dancer when he grows up almost created a family feud. When the father of one of his preschool classmates unintentionally called him a girl (he was wearing the favorite blue tutu, mind you), I cringed just a little. And I am often confused about the messages I'm sending him. I don't mind if he wants to wear lipstick to a birthday party -- "Mom, you wear lipstick when you dress up!" he reminds me -- but how do I protect him from the inevitable taunting that will occur as he ages?
I come back to my original question: what is normal? Sadly, my husband and I are learning all too early that the constraints of normality are very narrow indeed. Happily, my son, who at the moment is pretending to be Belle from "Beauty and the Beast," adorned with his favorite pearl necklace and earring ensemble I gave him for his birthday, does not yet know this. With luck and a little parental intervention, he won't for a very long time.
Lisen Stromberg lives in the Bay Area.
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They say mothers and sons have a close relationship, but this story may take the cake.
Taking to internet forum Reddit, a woman only known by her screenname of ‘u/chewbawkaw’ explained that she’d been seeing her 30-year-old boyfriend for about a year and recently went on holiday with him and his family. It was one of the first times she’d had a chance to get to know her in-laws, who live in a different state.
While the parents were warm and welcoming, the woman couldn’t help but notice her partner’s mother was very touchy-feely towards her sons . Most parents are fond of a cuddle and a kiss, but she explained that it was nothing compared to what she experienced on the holiday.
For example, her partner would be in his bathing suit and his mother would come from behind and wrap her arms around him, caressing his chest and nuzzling his neck.
“She also did that once while my boyfriend and I were kissing,” the woman added.
Another time, the couple were sharing a cuddle in bed when the mother came out of her room and laid on top of her son, exposing her underwear. However, she said the mother was even closer with her other son.
“He would be in his little twin bed napping in just boxer briefs and she would come up in her nightie and spoon him,” she explained. “She would stroke his chest, thighs, back and arms. He would pull up her shirt to stroke her belly and would rub her body as well.”
The brother would regularly tell his mother how beautiful she was, although the woman said it would be sweet if she wasn’t rubbing her naked body on her son when he was saying it. The woman said no one in the family seemed bothered by the touching and even noticed the husband paying his wife plenty of attention.
“I also want to reiterate that I DO NOT think that this is a sexual thing (hopefully) between his family,” she wrote. “It just doesn’t seem like they ever updated their personal boundaries. Like if her kids were 4 years old instead of 30 this probably wouldn’t look as weird…right?”
She acknowledged that normal is subjective and that it’s just the standard people are used to, but questioned if it would be weird if she was in bed wearing a bikini with her own father spooning her.
“Most of me feels like I should just keep my mouth shut because he has two parents and a brother that love him to the moon and back,” she continued. “On the other hand, if he was raised in an environment where what would be typically considered sexual touching was used as non-sexual affection, it makes sense that he has been struggling with physical boundaries now that he lives away from his community.”
Other Reddit users offered their opinions and advice for the woman.
One person wrote: “This is very, very weird and inappropriate, and the mother is the one instigating it.”
Another comment read: “If you are an intuitive person than it would be a good idea to press your bf [boyfriend] a little bit about how far the mother goes. Gauge his reactions and figure out what to do next. He may need some help.”
A third added: “I was thoroughly disturbed by this post. That woman is creepy. Mothers don’t cuddle their barely clad adult sons while they’re wearing little nighties. And neither do adult sons lift their mother’s top to stroke their belly. Ick. In what reality is this all NOT sexual? If you and your boyfriend take your relationship to the next step, be prepared for creepy mommy to view you as competition that needs to be eliminated.”
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Published December 24, 2013 11:00PM (EST)
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I tore open the Santa paper to find a short red cocktail dress. “Try it on,” mother said, holding it up in front of me. “Just try it on once for mummy.” She stared at my offending Giants baseball cap and T-shirt. I grimaced. An inveterate tomboy and a closeted lesbian, I felt like an impostor in a dress. And in a red dress with the words “Santa’s Helper” bedazzled on the rear, I felt like an idiot.
I grew up in the ’90s, with a mother who wasn’t exactly the Angelina Jolie to my Shiloh, defending my boyish sartorial choices. Quite the opposite, my mom waged a war to get me into more feminine attire. Every week in high school, mother assaulted me with a new article of clothing. She was a middle-aged female Liberace, whose tastes veered toward the laughably eccentric and: a pink shorty robe spackled with butterflies, Lilly Pulitzer skirts, and various camisoles of varied levels of transparency.
Maybe the use of “assault” sounds melodramatic, and I admit that being plied with finery was an extremely first-world problem. But whenever my mother put me in a dress, I felt as if she were taking a scalpel to my identity, trying to slice out the parts she didn’t like. And the holidays were the best opportunity for her to operate on me. Weekends in December became forced marathon shopping excursions in which I tried on skirts and gowns that would later become my presents.
Her tactics were notorious with my high school friends, who’d come over after Christmas to survey my loot. “Has she met you?” my friend Amanda asked, laughing as she stared at the rack of multicolored miniskirts and then back at me, a 16-year-old in cargo pants and a breast-obscuring hoodie. “It’s like your Mom wants you to wear slutty clothes,” my friend Julia said, holding up a sequined tube top.
Perhaps my mother did. It occurred to me that she sensed I was gay. (At a young age, I already had “Xena Warrior Princess” collectable figurines.) I’m sure my mother thought if boys were more attracted to me I’d get straightened out, so to speak.
When I was young, my mom’s anger toward my style of style was so marked that I knew I wasn’t the child she wanted. I wasn’t a real girl. I was something twisted. I wanted to like dollhouses and frilly outfits but, no matter how hard I tried, I didn’t. By middle school, I thought I was a boy born in the wrong body. I tried on my father’s after-shave and cologne. I envied my older brother’s pants and crisp white-collared shirts. I’d often sneak into his room to try them on, tying my father’s pocket watch to the belt loop and twirling it around, pretending I was an old-timey gumshoe. “See here missy, we can’t take the case and that’s that!” If my mother caught me, she’d turn beet red and yell at me to go to my room and change. I knew something about me was wrong.
By high school, I realized I didn’t truly want to be male. But I didn’t want to be the type of girly girl my mother’s narrow sense of femininity mandated, either. It didn’t stop her from trying. Every family occasion became knock-down verbal warfare, with me fighting for my right to dress as I chose.
“You’re so ungrateful,” she said, as I opened a full-length purple ball gown on Christmas my senior year of high school and promptly frowned, tossing it to the side.
I can see where she was coming from. My mother grew up financially strapped in Kansas with a strict puritanical mother and a dying father. She could never afford the skirts and dresses that she lavished upon me. Her childhood princess dreams went unfulfilled. The adult ones had come true. With a home in the Bay Area, a career in editing and a successful husband in finance to boot, mom had it all. Buying me dresses was a way for her to fix a past tarnished by the scarcity she lacked now; but it was also her way of fixing me.
Two holidays ago, my mother started giving me gifts I would actually wear: a pin-striped blazer, a men’s wallet, and even a skinny tie. Gone were the multicolored miniskirts of yore. After the festivities wound down, I asked her what prompted the change.
My mother surprised me by admitting she’d been self-absorbed, only seeing m
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