French-Maid-Dress-Costume“Maybe I can find me a maid’s dress in there,” Bill said.

His girlfriend laughed. They were driving to Target for dog food, but Halloween was nearing.

“You couldn’t handle it if I wore a dress, pantyhose, and shoes,” he persisted.

“I’d just laugh at you,” she replied.

Bill didn’t say a word.

He remembers too clearly his parents arguing, his mother loading him up and moving out of their house and then back in—repeatedly. He remembers his mother becoming protective of him when he was hit by a car and he had to have brain surgery, his dad calling him a “pussy,” and Bill comforting himself by feeling his mother’s panties while she was at work.

He remembers taking care of his mother as she lay dying with cancer when he was 21, and he remembers marrying soon thereafter. His wife behaved just like his mother had. She loaded up their child, left and came back, left and came back. Whenever his wife left, Bill dressed in her clothes. After they divorced, he started buying his own women’s clothing at Sears, Mervyn’s, and Walmart—anywhere a woman simply worked a cash register rather than tried to help the customer shop.

Bill’s a cross-dresser.

* * *

He and I met through, a website for men and women interested in practicing alternative sex. I wasn’t interested in practicing alternative sex. I was interested in reporting on it. At the time, I was working on a book that became Secret Sex Lives: A Year on the Fringes of American Sexuality.  

Secret Sex Lives by Suzy Spencer

Bill’s a disabled mechanic from the Texas panhandle. Or as Bill described it in an email to me, where cowboys are “just about every where” and “where you would more likey get shot if they seen you dressed up.”

That’s Bill’s spelling and grammar, not mine. Bill doesn’t understand why “everybody” thinks a man’s “a queer” just because he likes to wear women’s clothing. “i’am a straight guy that for some reason i like the fill of woman clothes.”

Again, Bill’s spelling, punctuation and grammar, not mine.

But Bill wasn’t on AFF to find sex, even though straight married men inundated him with offers: “male squirt would like to fill that ass up!!!!”

He was on there to meet transsexuals and straight women, specifically wanting to learn how the latter reacted to cross-dressers. No transsexuals replied, but married women who helped their husbands shop for women’s clothing did.

That’s something Bill yearned for—a woman to take him shopping, help him pick out his clothes, take him home and dress him up, “then put on the makeup, fix the hair an paint my finger an toe nails just to see what it would be like.”

After all, he shopped for his girlfriend, and he thinks men should do things like that for “their women.”

“she tells everybody at work … how lucky she is to have someone that buys her all her clothes.”

In fact, Bill says his “better half gets so happy when i buy her some clothes i think she has an orgasm over it.”

I wondered if Bill was projecting his feelings onto his girlfriend. The feel of women’s clothing on his skin made him orgasm “quicker than anything.” But as soon as he ejaculated, he felt guilty and wanted to shuck off his women’s clothing as fast as he could.

“Why do you feel guilty?” I asked.

“have you or one of your friend had sex with some one that you wish you didn’t or used a dildo or something to have an orgasm. that is [kind of] the way i feel. i just want to get out of them now, than in a little while i forget … an think how good they felt and i’am ready again.”

* * *

brasBill’s been with a lot of women, he said, but not one has understood his need to dress. The woman he’s now with, who’d been his girlfriend for 12 years, “like all the rest she won’t even consider it.”

Bill insisted that was true despite knowing that one Thanksgiving, while his girlfriend was at work and he was home cooking their holiday dinner, he felt like putting on a bra. Unexpectedly, she came home for lunch, and there he stood, peeling potatoes in a brassiere.

“what could i do but stand their with my breast sticking out under my T-shirt like a sore thumb.”

She smiled a little bit and didn’t say a word.

But Bill believed his girlfriend “would die” if she knew how many bras and panties he owned. Then again, Bill has no idea how many bras, panties, pantyhose, and shoes he’s thrown away “because i didn’t want to get caught with them, or said i was going to quit, or start a new relationship with a lady.”

“really, i can’t understand why people want to judge the cd/tv/ts/tg people they are just like you an me. to me its no different than a woman or man going to church an get out an then go to a bar or go to a strip club or just set at home an get to drinking watching a sex movie.”

* * *

Bill had emailed a lot of cross-dressing experts. “an they tell me that crossdressing is something you never get over or you don’t stop. they say its in your genes. an it get worse as you get older because your male horimones start to drop an as that happens your body starts esterogen take over. they say that a male body has more esterogen horimone when we get older than a woman has as she gets older. they say the change starts around 40 to 50.”

Again, Bill’s grammar and spelling.

But I’m not pointing out Bill’s grammatical and spelling mistakes to make him look stupid. I’m doing it to show how a man who admittedly has suffered brain damage and is doing something that makes him uncomfortable – cross-dressing – is smart enough to get on the Internet and do research to try to find help.

The experts he’d communicated with identified her – Bill often goes by the name BeeBee and signed her emails to me “love BeeBee” – as a transsexual, since he wears a bra, panties, pantyhose, and high-heeled shoes.

TransGender butterflyBill strongly disagrees that he’s a transsexual.

He doesn’t wear high heels in public, he said. He just slips them on at home after his girlfriend goes to work, although he used to wear women’s panties under his work clothes, and he worried what people would have said if he’d ever been injured on the job and they’d had to take off his pants.

After he had to quit working, he had a similar worry when he drove around at night with a bra, panties, and pantyhose beneath his jeans and a pair of women’s sandals on his feet. Still, he’s never wanted a sex change, he said. “i’am a full blown guy.”

It’s just that women are so beautiful, so sexy, with their breasts and nice round butts and nothing hanging between their legs that he wants to be like them. “but i know that won’t happen so i dream about being with her.”

* * *

Sometimes, Bill longed to see his breasts grow larger, so he swallowed back his girlfriend’s discarded hormone pills. “i start seeing my breast get more full, than i quit. i’ll stay off of them for a couple months, because i don’t want them to get large because my better half might notice them. hell i don’t know why i try to hide them. i sleep without a T-shirt on an she see’s that their a little larger. …. she has not ever said a word about them, but at night sometimes she start rubbing them. i would like to hear your respondance is about what i have told you. an please if you want more let me know what you want.”

Bill was so nice I almost couldn’t take it. I almost felt like I was hurting him, as though I was taking advantage of an innocent. He wanted and needed a friend. I wanted and needed a source. I left him be … for a while.

* * *

Milton BerleWhen I did check in again, Bill said he’d been wondering if I’d forgotten about him and found “another weild, kinky old man that loves woman clothes too.” He lamented his cross-dressing and the lack of women who were understanding about it. “maybe you could answer why women are so afraid of us wearing women’s clothes. most men still love there wife even if they wear there kind of clothes. we still have the same old sex drive, or maybe a lot more of a sex drive.”

Bill and his girlfriend had watched a television news story about a transsexual. After the genetically born male became a female, she still loved having sex with women. Bill’s girlfriend couldn’t understand that.

“you must be smart,” Bill wrote me. And for the second time, he said, “tell me why women are so afraid for a man to wear their kind of clothes, shoes … around the house and under their own clothes. most women think we are sick perverts and a lot of other things, but we are really the same old boy inside.”

I had—and have—no answer for Bill as to why women don’t like to see men in women’s clothing. Maybe if I knew why men preferred seeing women in dresses over slacks, I’d know. Then again, I just thought men liked seeing women’s legs. Did women not like seeing men’s legs? I know a hard male thigh turns me on. But I think I like to feel it under a pair of jeans or stare it bare and tanned, not covered in nylon pantyhose. Or maybe it’s because when I think of a man in drag, I don’t think of those beautiful female impersonators. I think of Milton Berle—old and out of shape with overdone makeup, hair, breasts, and jewelry.

But I kept those thoughts to myself. I only told Bill that I was going to have to think and research that.

Bill sent me an email, thanking me for listening. “i’am afraid to even ask my better half, half the things i’ve asked you. i keep dropping hints to her, but she don’t respond.  … and i don’t want to ruin what we have.  … about a month ago we were out shopping and we went by a women’s dept an i dropped one of them hints that i needed a pair of those panties an she said you have some in your drawer, an she just laughed an that was the end of it.”

The next day he wrote, “she knows what my childhood was like. she wants me to go to a head doctor to talk it out. i feel like i have lived this long without going to one of those nut head doctors, why should i go now.…

“i guess what i am saying is that i would like for her to except me when i want to crossdress. i thank most crossdressers that was in a relationship, or married, have ended in a devorce or broken up because the lady could not except it. that’s why i asked you why can’t a lady except a man wearing her kind of clothes. i see women wearing mens jeans, shirts, boots, shoes, socks, even there underwear and we thinks it’s cool.”

I sat in my Levi’s 501s and thought about all the men I’ve known who’ve objected to me wearing men’s jeans. I wish more of them were as accepting as Bill.

* * *

Bill emailed another cross-dressing site and gave them basically the same information he’d given me, including the confession that he took his girlfriend’s hormones. He closed his email to them saying, “i don’t know what you would call me. a cd/tg or tv. what do you think?”

The respondents – a cross-dresser and genuine woman – warned Bill that he was “really playing with fire” by taking his girlfriend’s hormone pills. Doing such could cause a heart attack, stroke, liver disease, “as well as eventual loss of your male function.” And to his “what would you call me” query, they said, “From one letter, it is hard to say, but you sound like a very confused cross-dresser.”

I asked Bill how he felt about their answers.

“i have known for a long time that i had to except my crossdressing, i just got to have my better half except it.”

Just that day his better half had asked him if he’d bought any more panties. He’d said no, but he needed to.

I thought his girlfriend had been throwing out hints that she wanted to talk about his cross-dressing, and I told Bill that.

“i’am taken it slow with her. i guess i should have told her from the start, but i didn’t because she had two little children at home. i helped raise them an now they are grown an one is married an the other is in college … so its about time i do what i want to do.”

* * *

Several days later, I heard from Bill again. For the third time, he asked me why women don’t like cross-dressing men.

White knight

I guessed – and I emphasize guessed – that women weren’t attracted to cross-dressing men because of the white knight fantasy. “You know, a white knight is going to ride up and sweep them off their feet. But the white knight shows up dressed in women’s clothing and not a suit of armor, and it’s confusing. They don’t know what to think. They were never taught that the knight might be wearing women’s clothes and that wearing women’s clothes is fine or that it doesn’t take away from his ability to be a knight.  So they dismiss that knight and wait for another to come along.”

My answer didn’t satisfy Bill. He wasn’t asking about single women, he said. He was asking about women who have been married to the same man for 10 or 20 years. “if you have been together that long, she ought to know he’s not going any where. she also ought to know by now that he loves her. she ought to except a little change in their sex life. … you are supposed to know all these things. your smart an must be young an single an i bet your very cute.”

Bill started flirting with me and asked, “would you ever have a relationship with a crossdresser, or a transgender if he rode up on a horse in shining armour.”

I told Bill I had to think on his question. “But in a way, it’s irrelevant because I’m not looking for a life partner. Just friends. And as a friend, I’d have no problem with it.”

That was a lie. Well, at least a partial lie. At the time, I didn’t know whether I’d have a problem with it in a friend. But were I to know my lover was a cross-dresser, I probably …

* * *

As Bill and his girlfriend walked out of Target and through the parking lot, she turned to him and said, “We forgot to look for you a maid’s dress.”

Bill thought her tone of voice was serious. “One of these days,” he said, “you’re going to come home for lunch and I’m going to be decked out in a dress, pantyhose, bra and high heel shoes.”

“That would be okay,” she said.

The next day, Bill got up, put on a bra, then pulled on his t-shirt. When his better half left for work, she rubbed his back, kissed him, and said, “I’ll see you at lunch.”

“you know its great to get up in the morning an be able to put on a bra an not have to worry about getting caught,” Bill wrote me.

He wrote his better half too. He told her he’d been wearing women’s clothing for 30 years and he wished she could try to accept it. Then he anxiously waited for her to come home from work. He handed her the letter. She read it.

“You’re gay!” she screamed. “You’re bisexual! You’re a faggot! You want a man!”

“I want to talk about it, but after you calm down,” he said.

They didn’t discuss it that night.

The next morning, she yelled again. “You’re a faggot! You want a man!” She thought he wanted to leave her.

They fought. He plead again that he wanted to talk to her about it, but after she calmed down. She walked out the door for work.

Bill sat down and wrote her another letter, explaining that he didn’t want to have sex with a man. He didn’t want to have sex with anyone but her. “this is so hard for me to tell you this. i wish you would read up on crossdressing.” He gathered up the information he’d gotten from the various cross-dressing websites. When she came home from work that night, he handed her the second letter and the emails from the support groups, showing her that most cross-dressers are straight. He and his better half ate dinner, and he went into the living room to watch TV, never saying another word to her.

She didn’t say a word to him either when she left for work the next morning. But before she got to work, she phoned Bill. “I love you,” she said, “and I’m going to try to work on this with you.”

“i picked her up for lunch,” he wrote me. “she was so nice an has been every since.” If he hadn’t had the email information from the cross-dressing support groups, he doesn’t know what would have happened. “she said she would try to help, try to understand that we have a femminin side to an it is something that we don’t get over. i think she is seeing that i am still the same man that she has had all along. i guess time will heal her feelings. time will tail.”

* * *

The following summer, I was going to be passing through Bill’s town. I emailed and asked him if I could see him. He said yes. I asked him for his phone number. He never replied. Never.

But I think of Bill every Halloween. And I’d love to see him in his maid’s dress, because I want to tell him how beautiful he is—inside and out.



Suzy Spencer is a New York Times best-selling author and journalist.
  1. laurie known as leanne. Reply
    I have been wearing female clothing sense I was 12 years that I am 70 years old. I still wear their clothes, and I am a full time pantie wearer. And I can not see any harm in a man wearing women clothing. And no one should judge a man for crossdressing.

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