Maggie May

By Amber Fountaine

Published on Jul 12, 2006

Transgender

Amber Fountaine stories contain sexually explicit descriptions of consensual sexual activity and are not suitable for reading by anyone under the age of 18 or anyone offended by reading such material. These acts include gay and bisexual activity as well as water sports, diapers, cross-dressing and other fetishes and perversions that may please the author's whims. The characters in these stories are fictional, but are based on the author's true experiences, as well as the experiences of others he has met.

Maggie May

(TV, Bisexual, Urination)

by Amber Fountaine

Margaret May Collins, nee Maggie May Krukowski, had a gentle side. Few if any got to see it. At forty-two, she was well on her way to becoming a hard-nosed businesswoman who expected, and usually got, what she wanted. She probably deserved some of the nicknames like "Dragon Lady," but not one of the more popular, "The Black Widow."

While her ex-husband had disappeared, he hadn't been done in by the black widow as was rumored. Anyone with the courage to ask would have found out his disappearance had coincided with his secretary's equally abrupt departure and in fact, the two were very much alive and living quite well, enjoying their life together on the West coast.

A good part of Margaret's stern behavior was the result of an unhappy childhood, her Catholic schooling, and the defense she used with regard to men. She was an extremely attractive woman, but any man foolish enough to tell her that would be rewarded with a look so cold that even the most ardent suitor would turn tail and run. Her physical needs, where it came to sex, were met by a combination of toys and travel. She had a large supply of phallic devices of various sizes, shapes and styles, some battery powered, others simply manually operated, and all the toys in her collection were used regularly. In addition, she made what she described to her employees as 'business trips' that were actually mini-vacations.

Depending on her needs at the time, those trips might be for a day or two or several days and varied from a hundred miles to traveling completely across the country. What she was actually doing during those trips was sating herself with sex, usually men - sometimes more than one at a time - and occasionally women as well. If traveling by plane, it wasn't unusual for her to land with her first fuck in tow, and a few times, she'd had sex in an aircraft lavatory. She particularly liked to find men on those flights that lived in the destination city and who could provide her with some equally horny friends. It saved a lot of time and bar trolling. The very few people that had known her for all her life would have been amazed to know the truth about her sex life.

Compared to the beautiful woman she became, Maggie May Krukowski as a teen would best have been described as plain, bordering on homely. She'd started high school still wearing a training bra. She'd finished high school without one. Only two people knew that Margaret May Krukowski, class valedictorian, was totally naked beneath her graduation gown and that her nakedness was part of the reason for the rare smile on her face during her commencement address.

The other part of the reason behind her wicked grin had been that in a very short time she would be loosing her virginity to the same boy that had moments earlier sprayed her tits with his cum. She swore to her few close friends in later years that she could smell the heady aroma of cum as she spoke.

Maggie May was the youngest of five Krukowski children. The oldest was Alton Jr., then Mary, Richard, Pamela and Margaret. In relation to her age, they were ten, eight, six, and four years her senior. She'd grown up detesting the 'Maggie May' nickname everyone in the family except her father had used. Her father, from her earliest memories to his dying day had called her 'Margaret' or 'Princess' and for that, if no other reason, she'd loved him dearly.

By the time Maggie had entered puberty, her two oldest siblings were gone from home and her sister Pam had been the one to introduce her to female masturbation, girl-girl sex, and had put her wise to the often-strange sexual habits of the male species. When Maggie was old enough to date, none of the boys wanted to be seen with her. By the time she'd blossomed and they were vying for her attention, she didn't want anything to do with them.

It had been generally assumed that Maggie was a lesbian. That was caused in part by Maggie's fumbling advances toward another girl not long after Pam had shown her what fun two girls could have together. Maggie had tried to share her new knowledge with a girl she considered her best friend and the girl, instead of jumping in bed with Maggie, had gone to their mutual friends, telling everyone that Maggie had tried to seduce her.

As a result of that fiasco, and her early attitude toward boys, Maggie had gone through almost all of her high school years without a date. The most shocked student in the whole school had been Billy Wilson, the boy she'd barely beat out for valedictorian, when she'd walked up to him two weeks prior to graduation and told him, "You are going to be my date for graduation night."

Billy had asked her out a couple of times, but like the rest of the boys that asked, had always been rejected. So he was very surprised by her suddenly deciding to go out with him. He might have been much more shocked had he known the reason for his selection and her plans for the evening.

"Why do y'all call him 'Wee Willy Wilson'?" Maggie had asked some of the girls who had been joking about him during pep squad late in her senior year. That drew cackles from the girls and Maggie had persisted.

"For the class genius, you sure are dumb," one of the girls opined. "It's like the same way they call bald men 'Curly' and big guys 'Tiny'. Now do you get it? Wee Willy . . . . . think about it. He's got like three legs."

It had taken her a moment to realize that 'Willy' was yet another nickname for the male sex organ. "Is he really that big"? she'd asked, trying to picture in her mind a penis of leg sized proportion. She'd only seen two in her entire life - her brother Richard's and her latest brother-in-law Tom.

Again the girls had their fit of laughter at her expense. "No dope. No guy is really that big. But his sister Betty says he's bigger than any guy she's seen and she's fucked half the guys in school." Then another of the girls had added, "And he ought to be just your type. Betty says he likes to dress up like a girl and is always stealing her clothes and he dated Joann for a while and Joann says he has a great tongue."

It had been meant as yet another reference to her being lesbian, but the remark had instead given Maggie the beginning of a clearly defined plan. She'd seen her brother Richard go through a period of time when he would take some of Pam's lingerie from the bathroom clothes hamper and put them on to masturbate. She'd caught him at it and in exchange for her silence; he'd had to agree to dress in panties, bras, slips or nighties, and jack-off for her entertainment. She wouldn't get naked as he often requested, but numerous times had bared her budding breasts as a target for him to shoot his cum. Then Pam had caught them both and put an end to all that.

So when the girls had let it out about Billy Wilson liking to dress up, Maggie had been interested and not for the reasons the girls would have expected. She'd seen the way that Richard's cock would tent the front of Pam's panties and could only imagine what Billy's might do to hers. Beginning that moment, she began to imagine it several times a day and at night in bed.

The night of graduation, Billy had picked her up and the two had driven around for several minutes waiting for Maggie's parents to leave for the commencement ceremony. As soon as the house had been empty, Maggie had drug the unsuspecting boy inside and told him her plan. She'd stripped naked, had him do the same, and paused to admire his cock. She didn't seem to think it was all that much bigger than the two she'd seen, but she'd never had the nerve to touch one and couldn't resist. She might even have put it in her mouth if her touch hadn't been more than poor Billy could handle.

She never flinched as his erection suddenly squirted out ribbons of cum, most of which coated her bare body from the chin down. Then she dressed him in her panties, bra, garters, hose and slip, ignoring both his questions and protests. She had allowed him to keep his shoes and socks and with the floor length gown in place, no one would be able to tell that Billy was wearing lingerie.

Then, not bothering to clean herself off, still wearing nothing but his discharge under her graduation gown, she put on a pair of flat shoes, grabbed some casual clothes for later, and hustled him off to the ceremony, promising him her pussy as his prize for participating in her plan. She was sure he'd be able to get hard again.

Whatever else her faults might have been, Maggie always made good on her promises. Not long after the ceremony was over, the two young lovers had locked themselves in a bedroom at a friend's graduation party and consummated their deal. Fucking, Maggie decided that night, was WAY better than any masturbation trick she'd learned so far and she'd tried a bunch. And Billy, as advertised, really did know how to use his tongue. He'd had her climbing the wall and very, very ready before slipping on a rubber and slipping himself inside her wet and willing vagina. And when he'd finished, she showed her first signs of the type of woman that someday she would become. She'd made Billy swallow the contents of his used rubber.

Maggie saw Billy several more times that summer and each time a scene similar to their first encounter had been repeated. Usually in Maggie's bedroom while her folks were at work, Maggie would dress Billy in lingerie and use him as her lesbian lover until she desperately needed to fuck. Then she'd have him mount her, urging him repeatedly not to cum too quick and when he'd finished and pulled out, she would remove his rubber, lick his cock clean, and drain the cum from his used rubber into his mouth. She could tell that Billy was no stranger to the taste of cum, but never thought to ask if he'd tried anyone else's besides his own.

Toward the end of the summer, Billy had given up on the idea of college and joined the Navy and Maggie had enrolled at Mid-State University with the intention of studying nursing. Almost immediately after moving into her dorm room, Maggie had gone to the campus clinic and had been one of the first new freshman coeds to get a prescription for birth control. For the next two years, she had enjoyed numerous bed partners, both male and female. After a few letters and postcards, she had lost touch with Billy Wilson.

Then, just before her twenty-first birthday, Maggie did several stupid things. She'd heard that problems always arrive in groups of three and she gave evidence to that theory. First she forgot to take her pills and got pregnant. Then she had an abortion that resulted in some serious problems. And no sooner was she over that and back on her feet, then she fell in love with a self-styled ladies man named Cory Collins and dropped out of school to marry him.

Coming from a large family, Maggie wanted to start a family of her own. Maggie's parents were usually quiet on the subject, but were beginning to show signs of being very upset that none of Maggie's older brothers and sisters had provided the aging Krukowski's with a much-wanted grandchild. While birth control was never discussed in the Krukowski's strict Catholic household, Maggie's parents were beginning to suspect their older children of that unspeakable sin. There didn't seem to be any other explanation for the lack of conception in what appeared to be four otherwise happy marriages.

Maggie, ever the one to try to please, had offered to try her best, getting smiles from her happy, but blushing parents.

After several years of marriage, so much connubial bliss that one evening, during their energetic coupling, a bed had been broken, and still no positive results to show from their efforts, the happy couple had sought medical help. She learned from a very thorough medical exam that the abortion had resulted in scar tissue and other complications that would pretty much guarantee she'd never bear a child.

Suddenly all the words of the nuns at what she referred to as the 'Sisters of Perpetual Guilt' came flooding back, "Sex without marriage is a sin!" "Sex is for procreation and not recreation!" "The seed of life grows only in the womb of the Holy!" Etc., etc., ad infinitum. She couldn't count the laps around the beads she'd had to do after revealing her 'impure' thoughts in confession.

From the very active sex life she'd led for the previous ten years, Maggie then turned 180 degrees in the other direction. Suddenly she couldn't stand for Cory to touch her and the sight of his rampant, ever-ready erection, which she perceived as the 'root' of all evil disgusted her. Unexpectedly cut off, not surprisingly Cory found the answer to his sexual needs outside the home. When he had finally asked her for and had been denied a divorce, he told her, "No problem." Two weeks later, taking only a few of his clothes and less than half the money in the bank, he was gone.

At almost the identical time, Maggie's mom was diagnosed with the late stages of terminal cancer. Maggie's older siblings were scattered across the country and weren't in a position to help. Maggie moved back home to try to lend a hand. Unfortunately, there was nothing anyone could do but accept the inevitable. Maggie's mom was gone almost before Maggie got her bags unpacked. And when her mom died, so did her dad, at least inside. It had been as if his spirit had left with hers. Her dad almost turned into the baby that Maggie had tried so hard to have for all those years and in some ways, she found that both ironic and pleasant. In the few short years it took him to finally fade away, she watched him become almost as dependant as a newborn. It also made her realize how difficult it could be to find home health care products in a small town like Millburg.

She started into her business almost by accident and more on the order of a co-op. She normally drove her dad's Buick around Millburg when she had small errands to run, but still had the Chevy Suburban from her marriage to Cory. She'd known of a couple of other families with invalids like her dad and offered to make a weekly, seventy-five mile run to the next major city to buy cases of diapers, bed pads, or whatever else they might need. Word spread and soon she had several calls a week - some from people she'd never heard of - and they all were offering to at least let them help with her gasoline costs.

Over the course of a few weeks, she figured out what products were most needed and not kept in local stores. Within a few months, her dad's garage had begun to resemble a medical supply house.

Then a check with the local Chamber of Commerce - virtually a one-man operation in a town the size of Millburg - had revealed that while the town was growing very slowly, the average age of the city's residents was climbing rapidly. The last census had shown a 4% growth in population and a 12% jump in average age. Further checking by way of the Internet had divulged that there were many, many small towns across the country in a similar situation. Using some money from her dad, some of her own, and some that she'd managed to beg from the bank, she started the first of her mail order businesses.

She picked one or two towns at a time - towns like Millburg that were big enough to have a weekly newspaper and not much else - took out a year-around, small display ad for "Discount Medical Supplies" and offered a free catalog. All the envelope stuffing, addressing, and postage licking, she did herself.

Her business compounded itself faster than interest. It took two years to reach $50,000 in sales. It took another eighteen months, to reach $100,000 and only a year after that, after putting on two subsidiary companies, they'd sold an additional $200,000 in six months. Maggie knew she was doing good when the bank started calling her to see if she needed more money for expansion or inventory.

It was right after her dad died, and she didn't have to split her time between work and taking care of him, that she began making her 'business' trips. A couple of years after that, her business seemed to peak at just under a million in gross sales a year. That's when she noticed that so many of her fellow aircraft passengers were traveling business people using laptop computers to promote their businesses.

That sparked another idea. She needed a website to reach all the people in towns that were too small to target for a catalog ad and those that lived nowhere close to a town. A farmer in the sticks, she determined, was just as apt to eventually need invalid care items as someone in the city.

And she was sure her two subsidiary companies, with their unique interests, could use sites of their own. By looking at the items ordered, she'd learned to distinguish which of her customers might have interests that went beyond a medical need and had correctly thought there might be a need for someone to answer that unique segment of the market. She was certain that using a website would greatly expand her exposure to that distinctive market.

Maggie had enough computer savvy to have set her company up right from the beginning with computerized inventories, ordering, shipping, payroll, etc. But she was clueless when it came to setting up a website. She knew how to use the web, but nothing about how to get on the web.

So using a search engine to find 'Web Site Designers' in her ZIP code area, she found two. Of the two, she picked the one that had a company name similar to her own. For her parent company, she'd used the name, "MM Medical" and the website design company she picked was "WWWebsites. Their website was very professionally done and after clicking on the request for information, waited to be contacted.

She never expected that the person to contact her would be "Wee Willy Wilson." And William 'Bill' Wilson certainly didn't expect Margaret Collins, the owner of "MM Medical," to turn out to be his old flame, Maggie Krukowski. After the shock had worn off and each had gotten their polite, "Good to see you" and "How have you been" out of the way, they seemed to try to outdo the other in their professionalism. An hour later, Bill departed with a deposit check in his pocket and a courteous handshake.

On his second visit the following week, Bill had her website home page up and running and was ready to begin putting in the catalog of items available. He explained the least expensive way would be for him to train her, or one of her employees, on how to add and set up the catalog pages; that for him to sit in her office doing it for her at his regular hourly rate would add greatly to the costs and be more than she might have expected. She smiled and told him that 'doing it in her office was fine' and seemed to enjoy seeing him blush.

At home that night, while digging out her 'toys', she tried to tell herself that she'd told him to, "do it in her office," to impress him with her ability to pay his rates and the fact that he'd nearly choked, blushing at her choice of words and the way she'd emphasized her expression had nothing to do with it. She also tried to tell herself that she didn't really care if he was impressed or not and that having him in her office for most of the day, working side-by-side with him, had nothing at all to do with her Freudian slip and that the reason her panties were so wet was because she hadn't taken a trip in a while. And it was probably pure coincidence that she selected a dildo from her collection that just happened to be the same size as she remembered Bill's cock had been those many years ago. Maggie had gotten very good at denial.

But try as she may, she couldn't think of a single excuse for why she whimpered Bill's name when she orgasmed.

The fact that he could just as easily do the work from his office as hers wasn't lost on her either. The second day they'd had lunch together and that's when they got into more personal reflections on each other's lives. She learned he had gotten started on computers in the Navy and had stayed in for ten years before getting out to join a computer software manufacturer. He'd spent almost another ten years with that company before starting off on his own. They laughed over the fact that they'd probably both been at the courthouse on the same day to file an assumed name for their respective companies.

They were both in a much lighter mood when they returned to her office and it didn't take long for Margaret's staff to notice and the eyebrows to start going up. Especially when Bill kept calling her Maggie, something none of her employees would have dared to do.

It was their third day together, a Thursday, when Bill, and Margaret - who still served as the company buyer and sales manager - began working on the pages for the personal hygiene items. The walkers and wheelchairs and oxygen equipment had all been so clinical, as had bedpans and dressings and things of that nature. It was when Bill got to the adult diapers, plastic pants and related items that he seemed to get flustered and nervous and Maggie noticed it.

"What's the matter Bill? You look like you've got a problem. Do those diapers come in too many sizes, brands and styles?" she teased.

"Uh no," he stammered. "There aren't that many price breaks. Just a matter of getting it in there right."

"Some people are surprised to find that those products even exist," she continued, watching him closely. "I know I was. My dad was in diapers day and night for the last few years he was alive. That's what got me started in this business. I can honestly say that my business began in wet diapers." Then she acted apologetic but continued to tease him. "Oh I'm sorry. I'm embarrassing you. You must have an incontinence problem. It must be rude of me to talk about diapers and such when you can't help it if you wee-wee in your panties." She'd been trying to find a way to bring up his former fascination of lingerie. She wanted to see if he still had that interest and it looked as if she'd scored a direct hit.

Bill began to turn to look at her, his mouth opening slightly as if he was going to speak and then stopped. It was enough of a move though, that she could see he was blushing heavily. She knew he wanted to make some sort of denial, but somehow couldn't. She loved having a man at a disadvantage and pursued it. "I told you I have two other subsidiary companies that I'm thinking about having you do web sites for too - after we get done with this."

She walked over to a filing cabinet and returned. " Look at these two catalogs and tell me what you think." She handed him the two, smaller catalogs from each of her subsidiary companies. Then she went behind her desk where she could watch with amusement as he literally dissolved.

The top catalog was for sexy lingerie and adult sexual toys. He turned a darker shade of red paging through that one, but she'd told him to look at it so he had to at least pause at some of the pages. Then he got to the catalog for 'ABy-Baby World' and poor Bill turned purple. Maybe it was the lighting, but she swore she could almost see tears in his eyes.

"I thought you might enjoy the lingerie catalog," she told him softly, letting him know that she hadn't forgotten how much fun they'd had when she dressed him in her things. "You'd be amazed at how many business professionals like yourself order things from it. In fact, I was planning to offer you a discount if you're still into that. But it looks to me like it's the Adult Baby things that thrill you the most now. Am I right?" She found herself willing him to answer 'yes'.

Bill wouldn't even turn to speak to her, as if playing possum would make her go away. Unfortunately for Bill, his silence gave her time to suddenly think of another, more discreet way of getting an answer.

To throw him off and make him more at ease, she told him, "Oh well, if you're not going to talk to me, I might as well get to work." Since Bill was busy at the computer on the side desk in her office, she went to the computer on her secretary's desk and pulled up, by ZIP code, the mailing lists for both of the subsidiary catalogs. There was only one ZIP code for the entire county around Millburg and she quickly found what she was looking for.

There was a 'Ms. Billi Sue Walters' who received both the 'Nice & Naughty' and the 'ABy-Baby World' catalogs at the same PO Box number that was on Bill's business card. Coincidence? She thought not. Then she clicked on the customer number to have the computer check for purchases. If a catalog recipient didn't make a purchase after three catalogs, the computer automatically deleted their name. Either Ms. Billi Sue was a new subscriber, or . . . . a customer.

Sure enough, Billi Sue had been a customer as well, having ordered at least once from each catalog. After making a mental note, impressed with a few of the items he'd bought, she returned to her office to find Bill working diligently as if nothing had happened. The two catalogs had been set to one side, as if the subject had been dismissed, so she picked them up, opening each to a particular page.

Bill was doing his best to pretend he wasn't watching her every move. He wasn't sure what she had in mind but had an ominous feeling nonetheless. There was a strange tightness between his shoulder blades unlike any he'd ever felt before. When she pulled up a chair and sat shoulder to shoulder next to him, he knew his time was near.

She leaned into him so that their shoulders were touching and held one of the catalogs up in front of him so that he couldn't ignore it. "I think you'd look cute in this nightie," she whispered, pointing to a black baby doll she knew he'd ordered, "But I'd get it for you in pink or yellow. You could wear it with some matching panties and bras. Wouldn't that look cute? Or better yet," she said, switching to the other catalog, "Under your pretty nightie, you could wear these cute little ruffled plastic panties over some super-thick pre-formed diapers. People that buy these diapers brag about how many times they can wet them before they have to change and the plastic panties are guaranteed to be leak-proof." Billi Sue had ordered three of each and she waited for him to comment.

But again Bill didn't say a word, trying hard to continue working as if she wasn't there and the conversation wasn't happening. He had his fingers poised at the computer keyboard but they weren't moving - shaking maybe, but not hitting any of the keys. It was his trembling body and the look of panic on poor Bill's face that spoke volumes to her. Grinning at her success, she reached behind her to get a business card off her desk and scribbled her home address on the back.

"Billi Sue's secret is safe with me," she told him, passing him the card. "I wouldn't stay in this business long if I started divulging any of that sort of information. As I'm sure you know, it says right on the order blank that "Complete Discretion is Assured." But I would really like to see, 'Ms. Billi Sue Walters', in person at my house tonight as soon as possible after work. Like seven o'clock sharp."

While her voice and tone had been harsh and demanding, Bill turned to see that her eyes were soft and drawing him in. There was absolutely no sense in denying anything. If she had the 'Billi Sue Walters' name, she already knew way more information than he wanted her or anyone else in the local area to have. "Yes ma'am," he told her, no longer sounding like a computer-whiz businessman, but more like the bedwetting teen-age girl he liked to pretend to be as soon as he got off work for the day.

Then she remembered that his purchases had included bras and it suddenly made sense that he'd never taken off his coat at lunch or at any time in her office since they'd been working together. She deftly snaked her hand inside his sport coat and it didn't take but a moment to confirm that he was wearing a bra under his dress-shirt. "You wearing panties or diapers today?" she asked, and he told her softly that he was wearing panties. "I remember you liked that a lot," she said as she let her hand drop to his crotch. There was a bulge there but not a diaper bulge. "He may be scared shitless, she thought, "but this stuff still turns him on and I know just how to use him again."

"Where did the interest in diapers come from?" she asked, then suddenly changed her train of thought. "Never mind. Finish what you're doing. But I want you to wear diapers under your dress and tell me all about it tonight." Then she thought to ask, "Do you have a boyfriend or girlfriend that's expecting you?"

When he shook his head, she told him, "Good. I'll have my housekeeper fix us some dinner. Be sure to dress up real pretty for me and I'll have a nice surprise for you."

Before he could say anything else, as if there was anything he could possible say, she was gone for the day. He tried to work 'til five, but it's difficult to use a computer when your hands are trembling as badly as Bill's were at that moment.

Billi Sue pulled up to the address he'd been given, shut off the engine and looked at the house. It was mid- summer and the sun was still well above the horizon at 6:45. He was a few minutes early and it gave him time to gather his nerves as he sat in his car, looking at the house. For some reason he'd expected her house would be something other than what he was looking at. Maggie seemed the type to be in an older home with a well-aged landscape. Instead it was a newer house, away from town and somewhat secluded. It was a house almost identical to his own and he double-checked the address he'd been given to be sure he hadn't gotten it wrong.

Not that he really expected it to look like Count Dracula's castle from out at the curb. But for that matter, it was a large house for someone that lived alone except for a housekeeper. Yet so was his and he didn't have a housekeeper; unless you counted his alter ego. He always dressed as Billi Sue to do housework. Each of his three bedrooms was dedicated to a different purpose, and used depending on the mood he was in. So there was no reason she couldn't have a dungeon hidden in there someplace. From the way some of Maggie's employees talked behind her back, it wouldn't have surprised him if it did.

Just that day he'd heard her referred to by one employee or the other as, "The HBIC", which he assumed meant 'head bitch in charge', "Wicked Witch of the West", "Dragon Lady", and sort of generically as, "It". Instead of referring to Maggie as 'she' or 'her', most everyone was in the habit of saying something like, "Is 'it' back from lunch yet?" or, "I've got some invoices for 'its' approval." He wasn't sure how many people she employed, but there'd been at least six in and out of her office today and none of them had referred to her as Maggie or Margaret, though they always addressed her as, "Margaret" when they spoke to her.

Finally he had to get out of his little sports car and head for the door. He decided to take his purse and leave the other bags in the car, at least for the time being. After checking his hair and makeup one more time in the mirror, he got out of the little sports car, smoothed down his skirt, threw his shoulders back to accentuate his padded bra, and stepped around the car to the sidewalk. Hearing his heels click on a concrete sidewalk always gave Billi Sue a thrill and this time was no different.

He had no idea whatsoever how she would react to the way he was dressed, but it was at her insistence that she was being visited by 'Billi Sue' and not Bill. He remembered that when they'd had sex, back those nearly twenty-five years in the past, that she liked him to dress completely in her clothes, then would have them each slowly peel off layers until they were both down to panties and hot as a forest fire. The big difference for this evening was her insistence that he wear diapers under his feminine attire, something Billi Sue did often, but never in the local area.

For all extents and purposes, Bill led two lives. Bill Wilson, with sandy brown hair, drove an SUV to work every day. And the lady with the long blond hair, Billi Sue, would take her Mazda Miata whenever she left the house. Billi Sue was never seen in Bill's SUV and Bill never drove Billi Sue's Miata. In a town of 7,000 people, it wouldn't take long for folks to figure out that Bill and Billi Sue were indeed the same person. Like Maggie, Bill lived out on the edge of town without any nearby neighbors and had been getting away with his dual roles from the day he'd moved back home. While he would have loved the attention his long blond wig would have gotten him had he dressed as Billi Sue and rode around with the top down, he didn't want that sort of attention from anyone in Millburg. Between his house and the Interstate, he wore a scarf and kept the top up. But once out on the highway, or in other towns, he courted that attention.

In fact, this trip to Maggie's house was the first time he had been out anywhere at all to a local destination as Billi Sue. Normally, when Billi Sue left the house in 'her' little sports car, it was to make a beeline to the Interstate that ran between his house and the Millburg city limits and then on to some destination in one of the larger nearby cities. He had a few favorite bars and nightspots, some as close as thirty miles, but more often as far as another hundred miles. That's when the diapers became a big help. He'd usually have a couple of beers or glasses of wine at home while getting ready and the diapers allowed him to make the trip without a stop. Besides, he had a friend at one of his regular haunts that loved for Billi Sue to show up in soggy diapers. Carol Ann loved to suck on Billi Sue's piss flavored cock and Billi Sue loved the cock in Carol Ann's diaper just as much.

Coming home, it was the same thing in reverse, even at night. He'd go straight to his house from the Interstate, open the garage with the remote, and pull inside before getting out of the car. So walking down Maggie's sidewalk, even on the outskirts on the other side of Millburg, was a first.

Billi Sue was surprised to have a vivacious red head, half his age, open the front door before his hand reached Maggie's doorbell. He'd expected either Maggie herself or a Mexican maid, the standard area housekeeper, to get the door. Instead, a stunning red headed woman had startled him.

"You must be Billi Sue," the freckle faced woman, wearing a short loose dress, almost like a dashiki, told him when he didn't speak. "I'm Kathy. Margaret is in back at the pool. Please join us and I'll bring the drinks." Then she led him from the front door to a sliding glass door at the back of the house, indicating he should go in that direction.

If he was surprised when he met Kathy, he was stunned when he saw Maggie. She was wearing a pair of sunglasses, a smile, and absolutely nothing else. She'd gained a few pounds in the last twenty some years, but every single ounce of those pounds was in exactly the right place.

"Find everything okay?" Maggie asked, making no effort to cover herself.

Billi Sue looked at her in stunned silence for a moment, wondering exactly how in hell to answer her question; more specifically, how she meant it. Since he was obviously staring, he, guessed she was fishing for a compliment.

"I'd have to say that it looks to me like I found everything absolutely perfect," he finally answered in his soft, seductive, Billi Sue voice, as his eyes continued to appraise the view. He moved to the table and chairs near her chaise lounger and took a seat that would allow him to set his purse down and converse with her without seeming to be staring. If her nudity didn't bother her, he would try not to let it bother him. But he was sure glad he wasn't wearing thin panties or there'd be a very noticeable bulge in the front of his skirt right now.

"Did Mark Martin build your house?" he asked, looking for a subject that wouldn't get him in trouble. When she nodded, he asked, using a sweep of his hand to indicate the pool, "And Glenn's Pools?"

"Yes," she answered. "Right on both. How did you know?"

"Your floor plan seems to be almost a mirror image of mine. My garage is on the right of the house and the bedrooms are on the left. You've got your bedrooms on the right and the garage on the left. And my pool is a little smaller and more off the bedroom, but it has exactly the same ladder, board, and concrete and tile surface around it." Then he was out of conversational material and glad when Kathy arrived with their drinks.

"You've met my housekeeper," Maggie said, more as a statement than a question.

Billi Sue nodded and exchanged more polite smiles with Kathy, trying not to get caught looking down the loose hanging top as Kathy set drinks on the table. Then he watched in amusement as Kathy sat on the edge of Maggie's chaise and the two ladies held hands and began chatting.

Billi Sue watched in amusement, thinking, 'If she's a housekeeper, I'm the Queen of Sheba.' Enjoying the smooth, slush-like drink, he laughed to himself. He had no idea where 'Sheba' was, but he was dressed as a 'queen' and he found that amusing.

"You going in?" Maggie asked Kathy. "Just us girls here."

Kathy shot Billi Sue a glance and then nodded. "Might as well. I'm sure I'll get my hair wet later anyway." Standing, she slipped out of the shirt-dress and was every bit as naked under it as Billi Sue had suspected when he'd followed her through the house a few minutes earlier. Then she turned and dove in the pool, slipping effortlessly into the water in as beautiful and graceful a dive as Billi Sue had ever seen.

"Wow," he said, putting a word to his thoughts.

"The girl or the dive?" Maggie asked, watching him watch her.

Turning to Maggie, he smiled and told her, "Both. That was quite a dive and except for the hair color, she's almost your twin."

Maggie chuckled slightly. "Some people think she's my daughter and I hate to admit I'm old enough to be her mom. But, no, like I told you over lunch, I couldn't have any children. I met Kathy on a business trip last Christmas and we've kept in touch. She's out of school for the summer, so I hired her to be my housekeeper for a couple of months. And you're not the only one impressed with her diving. She drives a hundred and fifty miles round trip, three times a week, to practice at the nearest natatorium with an Olympic platform. She's won just about every college level competition she's entered and will be competing for a spot on next year's Olympic team."

"Wow, " he said again, beginning to sound like a mindless idiot, as he watched her climb out of the pool, walk to the diving board, and complete some sort of twisting, spinning, tumbling dive, again entering the water with barely a splash. " What was that?" he asked, again turning to Maggie.

"Damned if I know. She told me one time and it sounded more like a drink you'd order at a bar. She called it a 'one and a half something with a twist' as I recall." Then Maggie finished her drink and handed him the glass. "Be a sweetie and fill this for me would you please? There should be a whole pitcher of this stuff in the fridge. And if you'd like to go for a dip, you're welcome to go in like us or I've got an assortment of lady's bathing suits in the cabana."

It suddenly occurred to Billi Sue that maybe Kathy wasn't aware of his real gender, although as close as they seemed to be, it was unlikely that Maggie hadn't told her. "What about Kathy?" he asked, wondering what part she might be playing in whatever happened tonight.

"Not a problem. I told her what to expect and she's completely trustworthy. So do whatever you like. But AFTER you bring me another drink," she answered. "Actually, why don't you just bring the whole damn pitcher and leave my glass here. You've got some catching up to do."

He assumed her plan was to give Kathy the night off and have Billi Sue do the fetching and housekeeping in her place. That sounded like fun, especially since he was being encouraged to drink on the job!

Billie Sue soon discovered that the catching up he was supposed to do was only partly in the 'drinks consumed' department. Almost as soon as he was back with the pitcher of whatever it was, and had quickly downed a second one, Maggie began to press him for more details on his sexual fetishes. "How did you get from dressing in dresses to diapers?" she wanted to know. "Surely it's not something you learned in the Navy."

He took a deep breath, glanced from one woman to the other and decided to begin in the beginning. "Well really, that's backwards," he started; trying to think as both bare-breasted ladies joined him at the table. "I guess you could say I went from liking to wear diapers, to dresses, and then back again to doing both and it started in elementary school long before we moved to Millburg."

Kathy had been standing off to one side, toweling herself. When she moved to sit at the table across from him, Maggie got off the chaise and joined her. He was caught in the 'headlights' of four beautiful tits and his mind was turning to shit. He tried to gather his thoughts by looking down at the tabletop only to discover it was clear glass and no help at all. Both women had sat down with their legs spread, the cleft at the base of their pubic hair tantalizingly visible. "Uhh. . . And as far as the Navy, not being able to uhh . . . dress up was one of the main reasons I got out. Well that and the bucks the software company offered me."

"Did you always want to be a girl?" Kathy asked. "I'm not trying to be nosy. Margaret told me about when you were in school and about you wearing her clothes and I've never known a guy that was into that."

Billi Sue was studying her face as she spoke and believed her sincerity. "Sort of, off and on," he told her.

Then he launched into the story of his childhood and being jealous of the attention his youngest sister got. "You probably don't remember Wendy. She was a lot younger than us back then. I was just starting elementary school when she was born. My mom and my two sisters seemed to stick together and sort of shut me out and I guess that's where I got the idea that being a girl would be better than being a boy. Especially if I could be a baby girl like Wendy.

"My dad was gone a lot and that was before we moved here and there weren't any boys my age to play with where we were living. So I was hanging around the house a lot, either watching TV or my mom and Betty take care of Wendy. For some reason, Wendy's wet diapers - not her poopy ones - fascinated me. When my mom would take one of Wendy's wet diapers off, I'd steal it and take it to my room, stuff it inside my underwear, and wet it some more. And I'd take one of my older sister's nighties and wear that too and pretend I was a baby girl."

He saw the two women exchanging glances and wondered what that was about. He was sure he'd find out soon enough and went on. "Then my mom caught me wetting one of Wendy's diapers and wearing Betty's nightie and she decided to punish me by keeping me dressed like that. She knew that my Aunt and her two kids were coming by to visit, but that was supposed to be part of the punishment for trying to be a baby again. Her kids were boys a little older than me and my cousins teased the shit out of me for wearing stuff like that. But my Aunt thought I looked cute and told me I was too pretty to be a boy.

"Anyway, that night my mom put some plastic under my bed sheet and told me I was to stay in wet diapers all week and wouldn't even change my sheets. The diapers would leak so bad they'd wet the bed every night, but she just let the sheets dry and made me sleep in the stinky sheets again the next night. She didn't make me poop in my diapers, but that was the only time I got to take them off. She'd gotten some big plastic pants and a pile of larger size baby diapers - maybe from my Aunt - and I think I went through them twice before my dad was due home. She told me if I promised never to wear my sister's diapers again, that she wouldn't tell my dad what I'd done. So I promised and never did."

Billie Sue paused to think and finish his drink and Kathy asked him, "So you didn't wear diapers again until when?" She was really into his story and Maggie was watching them both, amused.

"The next week," he told her, resuming his story. "Somehow I'd gotten so used to wetting those diapers all the time, that when the weekend came and my dad was home, I wet the bed every damn night even though I wasn't trying to. My mom figured it out the following week when she did the wash. She gave me a spanking and told me she thought I was doing it on purpose. I cried and told her I wasn't and she checked me and discovered I really was wetting while I was asleep.

"Then I guess she felt guilty because she thought her punishment had backfired and that she had been responsible for turning me back into a bed-wetter. So it became our little secret. She got more of the big plastic pants and larger size diapers and put it all in Wendy's room. She told Betty that it was for Wendy to grow into, but Betty knew it was for me. Every night when mom put a diaper on Wendy, she'd put one on me too and if my dad was home, she'd sneak in my room just after I'd gone to bed and diaper me then and . . . well . . . . I really got to liking it a lot.

"So if I woke up in the morning and my diaper wasn't wet, which was most of the time, I'd pee in it before I took it off so my mom wouldn't stop putting me in diapers. Then I tried peeing in my diaper before I went to bed and that was even better. That way I could enjoy it for a while before bed and I got to sleep in a wet diaper all night. And since it was easier to diaper me if I was wearing a nightie instead of my PJ's, my mom gave me one of her old, short, nightgowns and told me it was mine to keep until my wetting problem stopped.

"I didn't want it to stop. I guess at first it was the attention I got from my mom. But after a while it was the diapers. Even then, wearing a wet diaper felt so good to me. I'd try to get my mom to diaper me as early as possible in the evening. Then I learned how to do it myself and in the mornings, if my dad was on the road, I loved to run around the house in my wet diaper and nightie until my mom would make me change."

"How long did it take for you to stop?" Maggie wanted to know.

"Are you wet now?" Kathy asked with a grin, letting him know she was really enjoying his tale.

He answered Kathy's question first by blushing, nodding at her, and saying, "A little." Then he turned to Maggie. "Don't know exactly. I guess I was about seven or eight when she caught me wetting Wendy's diapers and I was nine - maybe even ten - when I stopped," he said.

"Why would you want to stop?" Kathy asked and the way she said it made it sound to Billi Sue like she meant he was a fool for doing so.

"I don't know if there was any one big reason. My dad changed jobs about then and was home more. I guess I was growing up and thought diapers were too babyish. We'd moved here from Crain where I was born and I had new friends. Tony Patton's folks bought a house near us and I had a guy to play with. I know I hated the way my cousins teased me about it and I'd be going to the same school they did. I was afraid they might start telling kids at school. No one reason that I remember.

"What I do remember is that one night I told my mom I didn't want to do that any more. She told me to put a diaper on anyway and that if I went a whole week without wetting, I wouldn't have to wear diapers anymore and she'd buy me the new bike I wanted. I couldn't really tell her that I didn't need diapers, that I'd been wetting myself for fun for quite a while. She'd have been pissed and I wouldn't have gotten the bike. So I just quit and that was the end of it."

"So when did you get to start again?" Kathy wanted to know.

Billi Sue looked off like he was trying to remember an exact date or something, but his mind was on something else entirely. The way Kathy had asked, why he wanted to stop and when did he get to start again sounded like he'd gone through some period of deprivation. He filled his glass from the pitcher and made like he was looking at it. Instead he was looking at Kathy's crotch through the clear glass tabletop. When he realized that Kathy had a hand in her lap and had been playing with herself, he couldn't help but stare. That called Maggie's attention to what was going on.

"Kathy? Could we control ourselves at least until he's finished?" Maggie asked her.

"I'm sorry," she said, pulling her hand away from her pubic area. "I thought you were pulling my leg about being turned on by a guy in woman's clothes. But it's getting me turned on too. I can't wait until we get started.

Billi Sue sensed that Kathy had probably, and inadvertently, given away something and a glance at Maggie confirmed it. His mind raced as he thought about what might be in store for him. Suddenly he couldn't remember if he'd been asked a question or had been in the middle of explaining something and if so, what he'd been talking about. It reminded him of his few experiences smoking weed.

Maggie seemed to sense his dilemma. "When did you get back to wearing diapers?"

"Oh, yeah. I guess that was right after I got out of the Navy and started working in Silicon Valley," he told her. He didn't want to leave out any pertinent details, but wanted to curtail this narration as soon as possible. "I saw a story in a Men's magazine about guys that have unusual fetishes and they even had the names and addresses of various organizations for guys into cross-dressing and that liked to wear diapers and be big babies. I knew about the cross-dressing clubs, but the diaper stuff was a surprise to me and it got me thinking about it. Then one day a few weeks later, I saw some adult diapers at a store and . . . sort of as a lark - not that I was thinking about doing it again all the time or anything - more like just for the hell of it, I bought them. But before long I was wearing diapers to bed almost every weekend. And then it was two or three times a week and sometimes all day and night on weekends - Friday night to Monday morning. So then I joined one of the diaper groups and . . . . . I've been doing it pretty regular ever since."

"And the nighties and panties and stuff?" Maggie asked.

Billi Sue smiled. "I guess you could say where that's concerned that I never quit. I couldn't do it hardly at all when I was in the Navy, but I still managed to wear lingerie whenever I went on leave. Maybe for a few years when I quit diapers as a kid - around ten to twelve or so - I quit wearing girl's clothes too. But I know by the time I got interested in sex, I was dressing in Betty's clothes again. I nearly died when I found out that my sister had told a bunch of you girls at school about me wearing her clothes and I hoped that was all that she'd told y'all. So I was really surprised when you told me that knowing I dressed up was why you wanted to go out with me. I didn't believe it at first. I thought you were just planning to make fun of me like my cousins. But when we used to get together and . . .you know."

He paused, trying to be discreet and not embarrass Maggie and discovered he was the only one embarrassed by the mention of their teenage trysts. So he went on. "When we used to get together, you seemed to really like it for me to wear your things. You dressed me like I was some sort of giant living doll that you were playing with and I really thought that was the greatest. I've met a few women since then that liked for me to do it, but not very many and none of them wanted me to do it all the time. And I've read about or talked to other guys that have tried to keep it a secret from their wives or girlfriends and that's even worse."

"Would you like to do it all the time if you could?" Kathy asked.

"I do," he told her.

"No," Maggie interjected. "I think what she means is, would you like to live full time as Billi Sue and not as Bill at all?"

"Oh. Well . . . . . no I don't think so. I have thought about it and did it a few times for as much as a week or two while I was traveling where I had to stay feminine the whole time. Most of my vacations I've taken as Billi Sue. But for some reason I think living full-time as a woman would take some of the fun out of it. One big mistake people make is thinking that all guys that wear women's clothes are the same. They're not. Some guys are like me that do it for relaxation or recreation. And other guys feel like they should have been born women and they do want to do it full time and a lot of them do." Then he paused again to try to put his feelings into words so that they'd know he wasn't putting the feminine gender down in any way at all. The women waited expectantly while he gathered his thoughts.

"My business is kind of unusual," he resumed. "I could do what I do just as easily from home if I wanted and save the expense of the office I have rented in the old Manor Building in town. But I do that to keep it separate. And nine out of ten of my customers I never meet face to face. We connect by email or phone and all of our business is done on the net and for the net. So really it would be no problem at all for me to live as a woman full time if I wanted. But then how would I relax?

"See, my business is not at all physically demanding. If I didn't like to ride a bike and have a small gym built into one of my bedrooms, I wouldn't get any physical exercise at all. But my work is mentally pretty rough sometimes and that can be even worse. So when Bill gets done with a rough day at the office, he goes home and becomes 'Billi Sue'. Bill has one bedroom, there's a gym in another and Billi Sue has her own room with pretty white furniture and a big canopy bed. Sometimes Billi Sue wants to be a grown up lady and sometimes a bed-wetting teenager and sometimes acts like a baby girl."

Maggie was nodding her head. "Makes sense to me," she told them.

Kathy agreed. "Yeah, I think I understand too. I know at school there are times I get all stressed out from the tests and swim meets and my parents and having to be so perfect for everyone and I just go off someplace where no one knows me and become a slut for a few days."

They all chuckled at that and Billi Sue was the first to speak. "I don't think that sort of therapy - or mine either - is ever going to be approved in any medical journals. But hey, if it works, don't knock it." Then he thought of something else and tried to look serious. "There's one question I want to ask y'all." When he was sure he had their attention, he asked Maggie, "What agency do you go to, to find a housekeeper like her?"

After the laughter had died down, Maggie got to her feet and took Kathy by the hand. "I think Billi Sue would like to look at the 'maid's quarters', don't you?"

Billi Sue, carrying the empty pitcher and glasses, followed the pair of women and thought he'd never seen a more beautiful sight. There was something so intensely erotic and picturesque as he watched the setting sun highlight their perfect forms and thought, 'Two beautiful asses. Four gorgeous ass cheeks. Wow! Just plan fuckin' Wow!" I have no idea where they're leading me or what they have in mind. But I'm in. I don't care if Maggie's turned into a full-blown lesbian and Kathy is too and I never get to fuck either one. I'll be happy just to dress like this or any way they want as long as I can be around them. I don't care if she does have a dungeon. I'm ready for the rack.'

He carried the pitcher and glasses to the kitchen sink and rinsed them without being told. Then he turned to see both naked women were smiling and watching him, so he did a sort of little curtsey move that got them laughing.

"There seems to be something you haven't mentioned," Maggie told him.

"About being a housemaid?" he quipped.

"No. But it's nice to know you're not a slob that expects to be waited on," Maggie told him. Then she went back to the subject on her mind. "What I'm wondering about is 'men'. You mentioned reading about the diaper club you joined in a men's magazine. I've tried advertising 'ABy-Baby World' in men's magazines like 'Playboy' and 'Penthouse' and it didn't do much good. But the ads I've put in men's magazines for men that are into men have done much better. And unless my memory is failing, the code on your customer number tells me that you answered an ad in a gay magazine."

Billi Sue was both blushing and speechless so Kathy jumped in.

"What she wants to know," Kathy asked giddily, "is if you're into guys only and how many times have you sucked cock?" The pink slushy drinks seemed to be affecting her more than anyone else.

"No to the first and a few to the second question," Billi Sue was finally able to answer.

"A few as in five or six or a few as in a few hundred?" Maggie asked, trying to narrow it down to something more specific.

Part of Billi Sue wanted to bolt for the front door but he knew he wouldn't nor would he try to lie. Instead he stood proudly and told them, "Somewhere in between. And if you're worried about disease, I don't do it that often, I seldom ever let a guy fuck me, even with a condom, and I always get checked a few weeks later.

"Now if you're asking how many different guys have I been with, it's just under thirty. I actually sat down one night a few weeks ago to see if I could remember them all. It just happened to be the thirtieth anniversary of the first time I did anything with another boy and I came up with a total of twenty-eight. And if you want to know how many times did I do each one? I have no fuckin' idea. I'm sure it was as often as possible under the circumstances," he said, getting another laugh for his honesty.

Then he started to enumerate. "Starting with Tony Patton, I'd guess we did it a couple or three dozen times over two years. Then remember Jimmy Kramer in High School? He and I got together at his house almost every day after school for over a year or two and that could be more than a hundred easy right there. And when I went in the Navy, I . . . ."

"Hold it!" Maggie said laughing. "I wanted something a little more specific than 'a few' but not this much detail. We could be standing here all night before you get done with the other twenty-six."

"Aw shit!" Kathy told them. "I was enjoying his 'blow-by-blow' account."

After they all stopped laughing at Kathy's play on words, Maggie told him, "I'd love for you to resume your story later. Might be a lot of fun if sometime I tried to remember each guy I've known. But let's show you the house first and you can tell us all about your cock-sucking Navy days later."

Then each of the women took him by a hand and led him toward the front of the house.

To be continued. Comments appreciated: amber_fountaine@hotmail.com

Next: Chapter 2: Maggie May 3 4


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