Author's note:
When we hear the term "womanizer" we think of a Bill Clinton, a Ted Kennedy (or any Kennedy), a Donald Trump--some straight man who can't resist chasing women even if he has a wife or girlfriend. The term is both glorifying and preoperative, but only mildly so. Not exactly the male equivalent of "slut." At THE ESTATE--that extensive rural retreat that once was the private residence of a late nineteenth century robber baron--the term has a nearly opposite meaning. And THE ESTATE's use would never be pejorative--THE ESTATE does not pass moral judgment on its members, their guests or its staff. THE ESTATE recognizes that among its transvestite/transgendered clients and guests are many who desire and experience the lost of their anal virginity on its grounds. It is the final act of being a woman--to arouse the lust of a man to want them as women, to accept into their bodies the manhood of another, to draw from that manhood the seed of life. For that purpose THE ESTATE maintains on its staff a group informally known as the womanizers--men who specialize in the anal defloration of the transgendered. The readers of Nifty.org have met two such staffers: William in "Postcards from THE ESTATE: Deidre's First Day" and Jeff in "Postcards from THE ESTATE: Mrs. Townsend." As different in technique, approach, attitude and results as night and day. One smug, self-assured, arrogant, cruel just short of sadistic. The other the Phil Donahue of womanizers. The author now introduces the readers to another womanizer--this one a member of THE ESTATE.
Postcards from THE ESTATE: The Womanizers--Guy Hughes
by
Eugene Webber
The bus driver recognized Nathaniel as a guest of THE ESTATE the minute Nathaniel left the airport terminal. That deer-in-the-headlights what-am-I-doing look of many who arrive at this small regional airport in the middle of nowhere. Most first-time guests had never heard of THE ESTATE before being invited; none knew of the extensive nature and variety of services it offers. The bus driver watched as Nathaniel approached the bus, recognizing the brochure and voucher in the young man's hand as he reached the doorway.
"THE ESTATE, sir?" the driver asked. It was really a silly question. The bus was a fifty foot long scenicruiser with THE ESTATE in foot-high Roman letters on the sides and back, and also on the destination windows on the right side and the front. It was also the only bus, scenicruiser or otherwise, at the airport--on in the county. But the driver knew better than to assume anything. His job was to deliver members and guests from the airport to THE ESTATE--and heaven help him if he leaves anyone stranded. Nathaniel hesitated, looking at the bus, then the brochure then at the driver. "THE ESTATE, sir?" the driver repeated.
Nathaniel nodded and ascended the steps. The interior was much more spacious than he anticipated. It had less than half the seats a regular tour bus had. Behind the driver was a bar complete with bartender. Between the bar and the end of the bus were two horseshoe alcoves each of which could accommodate four people. On the right side of the bus there were three such alcoves, the first one opposite the bar.
"You may sit anywhere, sir," the driver informed him. Nathaniel took a seat in the alcove across from the bar, facing front.
"Drink, sir?" This time it was the bartender who spoke.
Nathaniel nodded negatively. He would have liked a drink--needed a drink. But he wasn't sure of himself and wanted to retain his wits. He looked at the brochure and the vouchers in his hand, thinking about the events which led him here.
Five weeks earlier, Nathaniel was surfing the internet, dismayed again at the websites about crossdressers. One after another they were about submissive sissies dominated by a bitch wife or girlfriend, forced to do housework when not being orally or anally raped by the wife/girlfriend's macho lover or/and equally bitchy girlfriends. Nathaniel had no desire to be raped. He had no desire to be dominated. While not aggressive, or even assertive, he was not submissive. But he was a crossdresser. Sitting at his computer in a slip, panties, pantyhose, and three-inch wedges was ample proof of that. He'd been able to dress this way for the entire Memorial Day weekend, giving himself an extra day to indulge himself. But that letter from Guy he had received on Saturday had unnerved him, and he was looking for reassurance and support. He wasn't finding any.
Nathaniel began chatting with Guy over the internet about a year ago. It had been two years since he'd began wearing women's clothes, progressing from panties and stockings to full ensembles. Thank God for the internet! As he got deeper and deeper into transvestism, he began to question his sexuality. Was he gay? Bisexual? Something else? All the books on the subject said crossdressing was quite common, and most crossdressers where straight. Not on the web! Sissies, T-girls, gurls, T-gurls, trannies, special women/girls/gurls--whatever they called themselves, they were the same: pantied, skirted, pussy-whipped cocksuckers!
Nathaniel was most confused by the stories of guys who had been straight for the first quarter to third of a century of their lives being turned into these sissies simply by wearing their first pair of panties, or dressing as a woman for Halloween or an office party or for some other reason. His own journey into transvestism was long and complicated. A couple of pairs of panties left over from overnight dates; no clean underwear but the panties, so panties under his work clothes. He enjoyed the feel of the material. If the panties feel so good, what about stockings? Slips? Hey, women have been keeping this a secret, all this smooth and silky feeling against one's skin all day long! It took a month of wearing stockings--and having them ruined--before he began shaving his legs. The slips didn't become part of his wardrobe until seven months after the panties. A skirt was nine months, and a dress a full year.
Thinking about actually going out in public as a woman brought on the crisis of make-up and wigs. While no ladies' man, Nathaniel did date regularly. And having women spend the night--or longer--at your place meant that you eventually you accumulate not only panties, stockings, bras and slips, but lipsticks, bottles of nail polish, compacts. He wondered how the sissies in the stories are able to use these things perfectly their first time and to be perfectly presentable as women immediately. His first time trying this made him look like a badly made-up clown. Worse, it was hard as hell to get the stuff off! He soon found out that he'd couldn't wear make-up later than Saturday night if he wanted to look male by Monday morning. And that was with a lot of face washing on Sunday!
So he never went out en femme. And he didn't receive much reassurance on the web. Sissies wanting to meet him, sissy lovers wanting to fuck him. Everyone assuming he was gay, or he wouldn't be a crossdresser. Especially Guy Hughes. Nathaniel thought the name was made up, a play on huge guy, like his own en femme internet name of Ellen. Guy had responded to a chat room posting Ellen had placed seeking responses from straight transvestites. Mostly what he got were responses from their wives or girlfriends assuring him that his habit was perfectly normal and that there was a woman out there somewhere for him. But Nathaniel noticed it was always the wives/girlfriends, not the crossdresser themselves, who responded. And these wives were never as many as the sissies who castigated Ellen for not accepting that she was gay.
And the sissy fuckers. They all wanted Ellen's virgin ass. Guy was the least crude of them. He was up front about his bisexuality. He had sex with women, and sex with men who were passable as women. He was always the male in the relationship, and he currently saw about three sissies at any given time. Not together, but he thought anyone involved with him should realize that monogamy was not his thing. He didn't consider himself promiscuous, just active. He didn't believe in the straight crossdresser. If you want to dress like a woman, then you want to be a woman. If you want to be a woman, then you want to be fucked by a man. If you want to be fucked by a man, you're gay. And if you're a gay crossdresser, you're a sissy.
Nathaniel didn't like that word. Nor 'bisexual.' Or transvestite, transgendered, trans, trannie, T-girl, T-gurl, or gurl. In fact, he didn't like anything about the world of crossdressers except the clothing. Guy was unapologetic. He liked fucking sissies and didn't see any reason to call them anything else. He lived on a ranch in Alberta, Canada, so his relationships with sissies was limited to weekends every two or three months at THE ESTATE. Gays weren't exactly welcome in the world of Canadian cattle ranching.
It took about four months of internet chatting before this was revealed fully. Ellen--for Nathaniel never chatted--then cut off Guy. But Guy was persistent, sending e-mail at least once a week. Ellen read them all, even archived a few, but did not respond for nearly two months. But Ellen wanted to go out in public as a woman. For this she needed help on two fronts. First, where to obtain make-up that was completely removable, and second, someone to evaluate her as a woman. The first she decided to ask on the web. Guy gave her the name of a few of his sissies, having obtained their consent first, respecting Ellen's wish not to be contacted by every flaming drag queen in North America.
The second she did not actually express, but Guy guessed. In their earlier e-mails and chats, Ellen had described herself and her clothing, asking Guy what he thought worked. Guy had developed a pretty good idea of her from all this, but imagination is not reality. He asked Ellen to send him pictures of herself en femme. Ellen hesitated for several weeks, but began sending photographs about five months ago. Guy's first comments were harsh: Ellen dressed rather dowdy, and the headshots were of a man in a wig badly wearing make-up. This was followed with a gift membership to an internet clothing store serving crossdressers, and one for a photofax machine. The photofax was so that Ellen could send photographs of herself to Guy rather than by mail, and Guy could comment immediately. Then Ellen could make the changes Guy suggested and send more photos.
The camera was quickly replaced by a videocam. Within a week they were conversing face to face over the internet. Guy's appearance surprised Ellen. He was bigger than she had imagined. Not taller, just heavier without being fat. Guy read her surprise, and had to restate that he was a rancher. Ranching is not a job for skinny people. No rancher's wife is smaller than a 12, and many are 14s and 16s, with 18s and 20s not uncommon. Guy also had a full beard and mustache, more hair than Ellen had imagined. Guy pointed out that Ellen was seeing the real Guy Hughes, while he was only seeing Ellen, although he liked what he saw.
That first conversation ended awkwardly, but Guy e-mailed Ellen the next day, sans videocam. He wouldn't put himself on camera again unless she wanted to see him, but he did want to see her. For the next two weekends they spent about two hours each day with Ellen trying different make-up, wigs, and clothing for Guy and Guy making suggestions. Guy then said he had exhausted his expertise on the subject of make-up, and sent Ellen a gift certificate to Chrysalis, the online store for the transgendered. The videocam was extremely useful as Ellen received make-up tips from Chrysalis' on-line make-up specialists. Of special importance was the advice on easily removable make-up and the return to a masculine appearance. Now Nathaniel could become Ellen every night rather than just on weekends. After one week, Ellen was so pleased with the result that she insisted that Guy turn his videocam on so that she could see his reaction. He was very, very pleased.
Ellen was not aware of the cost of all this until an invoice was mistakenly e-mailed with one of her purchases. Nathaniel then realized that Guy had made a substantial investment in Ellen. When Ellen confronted Guy, he reiterated to Ellen their earlier conversations. Guy dated passable crossdressers, and, to Guy, all crossdressers were gay. He had seen the possibilities of Ellen in the first photographs, and was glad to help Ellen become not only passable, but desirable. And desirable Ellen now was. He wanted to fuck Ellen. More importantly, he wanted to be Ellen's first man.
Ellen was shocked back into being Nathaniel. He had thought of Guy as a man experienced with transvestites who was only interested in helping him become passable. He had not considered that Guy might have other motives. For his part, Guy was confused by Ellen/Nathaniel's reaction. He had never hidden his sexuality or his views on Ellen's sexual orientation. If Nathaniel wanted to keep Ellen in the closet, that was Nathaniel's choice. The clothing, the cameras, the make-up assistance--these were gifts. If their only relationship was by the internet, then so be it.
Ellen did not appear for three weeks, nor did she answer Guy's e-mail. Then two weeks ago, Ellen e-mailed Guy to thank him for all he had done, but also to confess that she didn't know what to do next. She really wanted to pass as a woman, to shop in stores as a woman, to have lunches as a woman. But she didn't want to have sex with a man. She just didn't see men sexually.
What Guy wrote next nearly caused her to faint. He told her to contact him in two hours as Nathaniel--as a man! When Nathaniel contacted Guy, Guy gave him a very close scrutiny--or at least his image on Guy's computer screen. Then Guy propositioned him: there is this private club called THE ESTATE which indulges its members various preferences, sexual and otherwise. Guy was a long-standing member, and was inviting Nathaniel/Ellen to be his guest for the Fourth of July weekend. Guy would make all the arrangements. He would e-mail Nathaniel a plane ticket and further instructions on the week before the Fourth of July.
The instructions were simple. Go directly to the airport after work, taking nothing with him. He was to go as Nathaniel, and return the evening of the Fourth as Nathaniel. For the rest of the time, Ellen would be Guy's guest. And while the choice would be wholly Ellen's, Guy hoped that he would make Ellen a woman that weekend.
For the next week, Nathaniel could barely concentrate on his work, earning him some stern words from his supervisor. He couldn't believe he was seriously considering Guy's offer! He was actually thinking about spending a weekend with a man as that man's girlfriend! He wasn't sure he could do it, but at 4:40 p. m. Friday, July 1st, he found himself in a cab headed for the airport. And now he was on a bus headed for THE ESTATE, unsure whether Nathaniel or Ellen would be returning on Monday.