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After you've finished reading, you might want to return to the DailyDiapers Story Index
Maggie May
By: UpseyDaisy
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.
Did you see this letter?" Carol asked. She was Maggie's new office assistant and sometimes caused Maggie to wonder. Part of her job was opening and sorting mail, making the chances of Maggie seeing a letter that Carol had just opened somewhat slim.
Maggie's business had grown to the point that she needed help with all the mail orders that were coming in. Almost all her products were shipped from a distributor directly to the customer, using mailing labels supplied to the distributor by Maggie. Her dad's garage had been a good beginning but wasn't near big enough to serve as a warehouse and Maggie had discovered that drop shipping from a distributor eliminated a lot of handling. But someone still had to process all those orders and get them out to the proper distributor.
It had quickly become a daylight to dark job if Maggie tried to do it all herself and take care of her dad at the same time. Her alternatives were to get help with her dad, or help with her business, and help with the business was deductible. In addition to Carol, there were also two high school girls that worked part-time handling catalog requests.
Carol always sorted the mail into one of four piles. One was for customers who were placing an order. The second was potential customers who requested a catalog. The third was for customer service issues, and the rest were letters or advertising - people who were begging or selling. The customers - the buyers - always came first and Carol processed almost all of those herself. Any customer with a complaint or question about a product, Carol helped if she could and passed to Maggie if she couldn't. The sellers and beggars were opened and stacked for Maggie to read, if and when she might desire to see what they had to offer.
Maggie had been busy all morning, working on a problem involving orders that were sent in with ISF checks and she wasn't in the best of moods.
"What letter and what do they want?" she finally answered.
"I don't know," Carol answered timidly. It seemed to her like Maggie wanted to bite her head off all the time these days.
"It's not an order and it doesn't seem to be about selling anything either. They just want some information about something I've never heard of. Somebody wants to know if we're sensitive to something. Might be political. You see if you can understand it." So Maggie had stopped and looked at the letter from some group that wanted to know if 'MM Medical, Inc.' was sensitive to the needs of AB's and DL's and if 'MM Medical, Inc.' wanted that information to be included in the group's newsletter.
"Who is this guy?" Maggie asked.
"No idea boss. All I know is he buys adult size diapers and plastic pants and was one of your first customers. I checked the name against the customer list." The mention of customers made Maggie look at the large pile of orders and it made her unusually flippant. Business was booming. She laid the letter on her desk, and hand wrote across the bottom, "Sure, unless your organization is looking for a contribution." Then signed it, printed her name and title, and gave it to Carol to mail. Usually, contribution requests were form letters and went straight to her trashcan. Since this one hadn't specifically asked for money, for some reason she'd decided to have fun with it.
Then to her surprise, she got a reply from the same guy a week later, addressed to her, and thanking her and letting her know that no contribution was needed but that members of the organization would be mentioning their affiliation with the BBC in their orders and hopefully, the gracious Ms.
Collins would find it in her heart to give a discount to future orders from BBC members.
"Isn't BBC the TV station in England?" Carol asked.
"Yeah, that's one BBC. But I think this is probably another. This guy is here in the states. I guess if we get a few orders from them, we can give them 10% off. We'll see." Then Maggie went back to placing ads in newspapers in new areas of the country. She was putting all profits back into the company's growth.
The first responses that mentioned BBC weren't orders, but a flood of requests for catalogs that came in on the '800' phone number Maggie used in her small ads. And unlike the catalog requests that came in from the small cities where Maggie advertised, most of the requests from BBC members seemed to come from large cities where her products should have been available locally. That didn't make a lot of sense to Maggie since her prices were about 10% higher than the chain drugstores. Her attitude was that business was business and the customer could spend his or her money where they wanted. Maggie was happy it was with her.
Over the next few weeks, they received enough orders with reference to BBC that Maggie had told Carol to give them the 10% discount and after that, hadn't paid any more attention to it. Then one morning she heard Carol say, "Oh shit"! Carol never cursed and Maggie nearly dropped her coffee cup.
Before she could ask Carol what happened, Carol stuck an order that she'd just opened in Maggie's face, telling her, "Look at the bottom"! Written across the bottom of the order were the words, "Big Baby Club member. Maggie looked confused and was trying to make sense of it when Carol gave her opinion.
"They're a bunch of sickos," she explained.
"They don't HAVE to wear diapers, they do it for fun and act like they're little babies.
My sister saw something about it on TV and she told me there were a whole bunch of grown-ups walking around in front of the cameras wearing these big old diapers." Maggie wasn't sure what to say in response. What she was thinking was, 'Don't look now Carol, but that would make the lady that signs your paycheck a sicko too.' Carol wasn't aware that Maggie often wore a diapers at home and sometimes to work. Maggie was glad now that she'd kept that a secret.
"Should I quit taking orders from them?" Carol wanted to know.
"Absolutely not!" Maggie told her, surprising the older woman.
"What I want you to do is go back and make a list of all the orders we've gotten mentioning the BBC, what they ordered, the average sale, and then find me the name and phone number of the guy that first wrote to us about the BBC.
No, wait, I've got a better idea. Just make a copy of every BBC order we have on file and put it on my desk. I'll study it tonight." The stack turned out to be much bigger than Maggie had expected. And Carol was still digging. Maggie studied it that night and about four more in a row before she made the first phone call. One of the things she'd discovered was that many of the orders didn't have a phone number and that a lot of the shipping addresses were contract postal stations. A lot of these people, it seemed, had reason to keep their interest in diapers a secret - just like Maggie.
The first person she called had been the man that had originated her connection with the BBC. Maggie kept the conversation very low-key and was amazed to find out there were a couple of thousand members of the BBC all around the world. She revealed to him that she too wore diapers for fun and relaxation and he explained to her what the AB and DL terms meant and gave her a lot of insight into the lives of BBC members.
"So there are over two-thousand of us," Maggie had concluded.
"No," the man explained.
"There are over two-thousand members of the club.
There may be two hundred thousand non-members out there that aren't willing to join any sort of group, or don't know about us, but love to wear diapers anyway. You're a good example. For every one of us in the BBC, there may be a hundred more like you who still think they're the only adult in the world that enjoys wearing diapers for fun. But because they get some sexual satisfaction from it, they keep it a deep dark secret." Maggie didn't respond to his remark about sexual satisfaction. It would seem the man already assumed that if Maggie wore diapers for fun, she would masturbate in them too. Instead, she thanked the man for his time and information and then did a few randomly selected calls to BBC members, using the excuse that she was the president of the company and was personally following up on orders to be sure everything had been received to their satisfaction. Then she asked if there were any other products the person might need and she was astonished at the requests, usually in a timid voice, asking in particular for good quality, adult-sized baby clothing.
That got her to thinking. She couldn't add items like those to her regular catalog, but possibly there was a need for a small catalog of things for all those AB/DL people. Then she'd thought with a grin, 'I mean all of 'us' AB/DL people." That idea got put on a back burner while Maggie coped with the death of her dad and the growing business and somehow in that mix, another idea had been born of necessity. Maggie had gone without sex, even shunning masturbation, almost from the day she discovered she'd never have children to the night she wore and wet a diaper. Now, stuck in the back of her mind, was the information she'd just learned about people using diapers for sexual pleasure.
Laying in bed one night soon after, feeling her hot pee flow and soak into the diaper, had made her instinctively reach down to make sure the outside of the diaper was dry. The outer plastic of the diaper was warm to her touch and it felt good to apply a little pressure, squeezing the soggy inner part against her pussy. In a matter of minutes, Maggie went from wetting her diaper, to feeling the heat, to applying pressure, to squeezing the wet diaper firmly against her pussy, to all out masturbation and orgasm. It was her first orgasm in years and left her breathless. She had two more before taking the diaper off the following morning.
While Maggie was rediscovering her sexuality, she was also putting strict limits on it. Her hand, and whatever other inanimate objects she could find, would be all that would be allowed anywhere close to her pussy. Men, and women too, only caused problems and she couldn't see the need for either anytime in her future. After Carol left and was replaced with a younger woman, Maggie also added to her company staff. At the same time, Margaret Collins became the dragon lady, seldom smiling around the office, demanding perfection in everything, and building a wall to keep those closest to her at a distance.
As her private masturbation sessions increased, she discovered that finding replacements for the sex toys she'd used years earlier was impossible in a town like Millburg. Some of those, she remembered, had been ordered by mail out of ads in one of her ex-husband's magazines. But in Millburg, you couldn't find any sexually orientated magazines to find the ads to order the products.
"Wouldn't it be nice if people in small towns could discreetly order naughty things," she thought and from that, the idea for her "Nice and Naughty" catalog was born.
It was another year or so before Margaret added the two subsidiary companies and by then, her occasional 'business trips' had begun. The first had been a legitimate business trip to visit a new distributor. The marketing and sales VP she visited was a few years younger, very suave and handsome, and Maggie had been putty in his hands. Instead of visiting overnight and returning home the next day, Maggie had spent over 48 hours in bed with him. An occasional fling, she decided as she floated though the following week, was just what she needed to relieve the pressures of the business world.
And as a businesswoman who thought in terms of man-hours and time management, it made a lot of sense to her to use her 'business trip' time wisely. Instead of having one cock, nine times, over three days, she decided that having two or three cocks, three times in one day was MUCH more efficient.
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As Maggie related her story, Billi Sue was watching her, feeling intimately closer by the minute. He could imagine exactly how she'd felt that first time she'd put on a diaper at her dad's house and wet it and then used the wet diaper to masturbate. He could remember when he learned about the world of adult diapering and what an AB was and what a DL was and how sometimes people are both and that a whole lot of adult diapers are sold for recreational use and not just for necessity. He could imagine the surprise Maggie must have felt when she discovered people were getting sexual pleasure from the products she sold.
And he could certainly sympathize with her need for sporadic recreational sex. It wasn't any different in his estimation than the things he'd done - meeting guys into cross-dressing, diapers, or both - going back to his Navy days. Of the twenty-eight men that he could recall having sex with, there'd been only eight in the last five years and again like Maggie, he'd often had two or three of those eight at one time. He might have been drawn into a sympathetic melancholy if Kathy hadn't stepped in.
"So I guess what you're saying is, if you could find six guys at once, you could be home by dark"? Kathy teased.
Maggie laughed at her.
"Not that easy. I tried six one time," she told her, glancing at Billi Sue to see his reaction, "and I damn near didn't get home at all."
"Awesome," Kathy told her.
"I'm trying to imagine what it would be like to have six cocks, lined up and ready. Even the parties I worked I never did more than two or three of the guys and I never fucked any of them, but the girl that got me started used to gang-bang all the time. She knew I wouldn't, so she never asked me to work those parties with her."
"I think someone else is thinking about the same thing," Maggie told her.
The sudden silence caused Billi Sue to look around him at the two ladies and they were both grinning at him. He blushed and shrugged his shoulders.
"Yeah, I just remembered," Kathy said.
"You were going to tell us about your cock-sucking Navy days. With a whole boat load of horny sailors, you've probably had a dozen at once."
"I don't recall making that promise," Billi Sue told them.
Maggie grinned and reached to squeeze his hand. That gesture wasn't lost on him. He'd seen her do it several times now to Kathy and it always came with that same loving look.
"When we came in from the pool you began to enumerate the twenty-eight men in your love life and had just gotten up to two when you entered the Navy. Remember now?" He smiled back and returned the squeeze.
"All twenty-eight?"
"Try for half," she taunted him.
"and we'll see how it goes. And begin with Tony and Jimmy. I think Tony moved just before we started high school but I remember him because his mom wrecked their car at school. And I had a crush on Jimmy Kramer. I think I might be jealous."
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Billy had planned to find a way to let his mom know he didn't want to wear diapers any more after they had moved to Millburg. He was certain that he'd have other guys to play with and didn't want it to get out that he ran around the house in diapers. But for the first six months, there hadn't been a single boy in his new neighborhood. So Billy continued to let his mom diaper him at night. Unfortunately, his dad's new job allowed him to be home a lot more and Billy had a hard time hiding it from his dad. Wearing a wet diaper to bed was cool, but the neatest part was wetting it and running around the house in it before bed or after he got up in the morning. Now that his dad was home a lot, Billy couldn't do that and it was taking most of fun out of being diapered.
Then a new kid moved into the neighborhood and Billy was in awe. The boy's name was Tony and he had a mountain bike that Billy thought was the greatest. He asked his parents for one and got the sort of, "We'll see," answers that meant he might get one for Christmas if he kept after them.
Then he announced to his mom that he was going to stop wearing diapers and when he'd stayed dry for a week, she bought him the bike. He felt kind of guilty for getting his mom to buy him a bike for giving up something he didn't really need to do - but not that guilty. So the two boys started at the local middle school together with new bikes and a new interest as well.
They'd both discovered girls and had heard about what was supposed to be the most awesome feeling in the world - sex.
Somehow, the gangly, nagging, pain-in-the-tail, female members of their species had changed. Even Billy's sister was taking on a new and curvier look and it was embarrassing to him that she seemed to be developing faster than he was. He knew that to be a fact because he, and sometimes his buddy Tony, would peek through the bathroom window to watch his sister take her bath almost every night.
"Man, she's gonna be a fox!" Tony whispered.
"She's already got tits and hair on her puss and we ain't got nothing. I think I wanna fuck your sister when my dick gets big." Billy knew that fucking was having sex. But other than that, he still wasn't clear on how that was accomplished. His dad had finished a few beers the night his mom had told him it was time to have a man-to-man talk with Billy and the end result was not at all enlightening from a technical standpoint. Billy had screwed up the courage to ask his dad for details and was told, "Don't worry about it. The girls aren't going to let you any way." He was almost out of Billy's bedroom when he'd turned and added, "But if you get lucky, make god damn sure you use a rubber." The next day he'd asked his new buddy what a 'rubber' was and his real sex education had begun. Everything considered, Billy should have become a sexual genius. He was one of the brightest kids in school and all he and Tony talked about was sex. Unfortunately, a good deal of the information Tony was passing on came from Tony's older brother Troy - not the brightest bulb on the tree. If Troy Parker failed one more grade, he and Tony would be in the same grade together. But bad information, if you're starving for it, is better than no information. The boys took Troy's word for a lot of things they later discovered were wrong.
"Ever watch her pee?" Tony asked one night, the following summer, as they whispered at the bathroom window, waiting for Betty to make her appearance.
The question sort of startled Billy as he'd never really given girls pee a thought. He remembered, when his mom was potty training Wendy, that she'd taken off the little white plastic cup thing at the front of the potty seat and told him that girls didn't need to use that. Billy had understood since he was aware that Wendy didn't have anything to pee with and when he asked his mom, she'd told him girls had a hole between their legs for that and then changed the subject. Apparently girls had a whole row of holes for one reason or another.
"Why would I want to watch her do that"? He asked Tony.
"Peeing is cool dude. Some people even do it on each other." Tony's eyes were locked on the crack in the curtains so Billy couldn't tell if Tony was serious or not. Then Tony suddenly ducked and didn't say a word and Billy's curiosity got the best of him. He raised his head above the windowsill and was astonished to see his dad. Thankfully, his dad was about to take a leak and was looking down at the toilet instead of off to the side or Billy would have been dead meat. He wanted to duck like Tony had done but he was frozen in place by the thing in his dad's hand. It was a cock that was ten times the size of any of the boys in his gym class. Then Tony eased in beside him and took a look too.
They never did see Betty that night. Instead they slept out in the yard in Billy's tent and talked about sex. This time they got naked to add a new twist and in the dark, had fondled each other's peckers, using the excuse that it was too dark to see how much the other boy had grown and therefore they had to feel.
"You jack off yet?" Tony asked and when Billy explained he didn't think so (since he didn't know what that meant), Tony demonstrated.
He did it to Billy's pecker and had Billy do it to his.
In the early morning, when Billy was going to go inside to pee, Tony stopped him and told him, "Watch this." Then, still naked, Tony crawled out of the tent and lay on his back on the grass and peed straight up in the air, letting it splatter back down on him. Billy was hoping and praying that his parents were sleeping late, as usual on weekends, as he followed Tony's lead.
Just as the hot pee began to fall back on him, Billy felt Tony move beside him.
"Get some on me," Tony whispered.
"Me and Troy do it all the time." Back in the tent, Billy asked what else did he and Troy do and Tony told him it was a secret.
"Troy found out how to make your dick grow faster and we do it all the time but it's a secret." Billy had begged to know the secret and Tony put him off.
"I have to get Troy's permission to show you.
And if I show you, you have to get my permission before you can show anyone else." Billy had never heard of a secret that big and readily agreed.
A few days later, Troy came over while the house was empty and announced he'd gotten Troy's okay to show him, explaining they had to get completely naked and hard before they could begin. When they were both in that condition, Tony explained, "What you do is make your dick harder than it's ever been before and then the next time it gets hard it'll start from there and get bigger each time."
"How do you make it so hard each time?" Billy asked.
"Suction," Tony told him.
"Me and Troy been doing this for a year and we're both a lot bigger than we were last year. I'll do you for a while first." Billy was awfully suspicious that the suction thing that Tony was doing to him was very much like what he'd heard called a 'blowjob' and giving another guy a blowjob was supposed to be very wrong. But Tony was obviously sucking as hard as he could and not blowing on anything and it felt better than anything he'd ever tried and if it was going to make his prick get bigger .
. . . . . He was even more thrilled by this new 'cock enlargement' idea when Tony had swallowed his cum, following what had to have been the most intense ejaculation Billy had ever had.
Tony assured him that to make the procedure work, it was necessary to keep the cock in place, applying suction, even as it was spurting cum, and that Billy had been twice as big as ever before when it had happened.
"That's what makes it work so good"! Then Billy discovered it was just as much fun to do it to Tony as when Tony had done it to him.
They did it once more that day and three more times over the next two weeks and Billy was happy to discover that it had made his prick get a full quarter of an inch longer. By the time Tony's family moved again, both boys had added nearly two inches to their cocks. Long before then, Billy had figured out that the growth they were seeing was due to maturity and that the suction had nothing to do with it. But he wasn't about to tell Tony that, just in case Tony hadn't figured it out too. Billy had developed a taste for cum and truly enjoyed sucking cock.
With Tony gone, Billy's outlets for sex became limited to finding new ways to masturbate. He developed other friends in school but none that seemed interested in any sort of sexual experimentation or that were dumb enough to fall for the 'suction' story. Listening in on a conversation between his mom and Betty opened a new avenue for him to explore.
"Mom!" Betty pleaded.
"Maybe you like 'em but they look clunky. Panties like that are for babies and old ladies. Girls my age don't wear cotton.
They look more like something Billy should wear." It was part of what seemed to be an on-going struggle between Betty and their mom over Betty's choice of underwear. Their mom considered Betty's choices to be too wild and racy for a young girl her age and Betty thought her mom's taste in lingerie was archaic. Normally Billy ignored these discussions but this time his name had been mentioned and he'd caught a reference to babies. Betty was always leaving her bras and panties laying around in the bathroom and Billy had ignored them until now. For some reason, his interest was piqued by the conversation and the word 'sexy' being associated with lingerie.
That night before his shower, he got several items of Betty's lingerie out of the bathroom hamper and tried them on. He didn't understand why Betty thought their underwear looked the same. Hers were much thinner, had a tiny waistband, and his erection was very visible. It took several attempts before he found a way to put on the bra and when he looked at himself in the long mirror on the back of the bathroom door, he began to pose and pretend to be a sexy girl. That image was ruined when he pulled down the front of the panties to jack off.
As Betty's efforts to convert her lingerie to sexier things began to win out, Billy's enjoyment of those sexy items increased too. Dressing in her clothes before his shower became almost a nightly ritual and always included pumping out a load of cum. Then he discovered it was even more fun to take a few of her things to his room and wear them to bed. It reminded him of when he'd done that with her nighties and Wendy's diapers many years before. So the next thing he tried was keeping a few of her things in his room and that's what got him caught.
Their parents had gone out for the evening and all three kids were watching TV when Billy announced he was going to his room to read. As an avid reader, there was nothing unusual or suspicious about that excuse and as soon as he was alone in his room, he got out the things he'd taken earlier in the day and put them on. He was getting good at putting on a bra and kept a roll of toilet paper in his room to use to stuff it. He put on the matching panties his sister had gotten for Christmas and a really sexy baby doll nightie that he'd found in the hamper and was surprised his mom had let her buy.
What he didn't know was that his mom hadn't let her buy it. In fact, it wasn't even Betty's. Betty had borrowed it from a friend to wear at a slumber party. Earlier in the day, when her friend had come by to pick it up, Betty couldn't find it. When she looked later and found it and some of her things in Billy's room, instead of confronting him then, she decided to try to catch him red-handed.
So when she burst into his room that night, not only was Billy's hand red, so was his face and the head of his dick. Billy was trying to stop his eruption and Betty was trying to holler at him. Instead they both watched in silent awe as ribbons of white cum spewed from the head of Billy's cock.
Billy had no idea what to say in a situation like that. He was additionally dumbfounded when Betty's angry scowl turned instantly into a grin.
"How many people know you're a pervert?" she said, fighting back a laugh.
That made Billy relax and begin to laugh too. It was the kind of question that his buddies at school were always asking. Like, "Is my cock the best you've ever had?" or "Does your mom know you sniff her panties?" They were questions where any answer was wrong. He thought Betty's question was a good one and he intended to remember it and use it on one of his classmates.
Since she was laughing about it, he decided to go along with her pervert question, "Just you and me so far. Are you planning to tell any one?"
"Yeah, like I really want everyone to know my brother is a pervert. Stand up and put that thing away," she ordered, indicating the cock he still held in his hand. For the next few minutes, she kept her thoughts to herself as she had him turn around, looked him over, brought a gob of his cum to his lips and waited for him to figure out she wanted her finger licked. Finally she stepped back and spoke.
"Don't let Wendy see you like that. I'm sure she'd tell mom." Then she was gone, letting Billy stew over what had just happened.
This was a side of Betty that Billy had never seen before. She had every right to be pissed off over his wearing her clothes and instead she was almost sympathetic. It all seemed so strange to him. He'd almost wished she'd been the mad and intolerant sister he'd grown up with for years. He should have known there was a method to her madness.
Betty was to be allowed to begin dating in a few months when the new school semester began. How better to learn about boys than from her older brother who, because she'd caught him in her clothes, would be sworn to secrecy. At first her demands were simple. Usually she'd let him dress up for whatever length of time they had the house to themselves, often making him masturbate for her enjoyment. Eventually she worked a confession out of him regarding the things he'd done with his buddy Tony. So she demanded that he find a friend to give a blowjob while she watched. According to her friends at school, hand jobs and blowjobs were the way to go to keep a boy on the hook and not have to worry about getting pregnant.
Billy had one friend in mind as a potential replacement for the fun he'd had with Tony. Jimmy Kramer seemed to pay an awful lot of attention to Billy's cock in the gym showers. Even before he'd been caught in the nightie by Betty, Billy had begun to use a locker closer to Jimmy. As soon as school started again, Billy had made sure his regular gym locker was next to Jimmy's and they quickly became close friends. Betty had said she'd do whatever it took to make it happen and eventually the perfect opportunity arose.
Wendy had what appeared to be a lazy eye and Billy's folks decided to take her to a specialist out of town, leaving Betty and Billy to look after themselves.
"No parties!" his dad had demanded and Billy told him that Jimmy might spend the night but they had no intention of having anyone else over.
"See that he's the only one that comes over," his dad told Betty. Already aware of what Billy had in mind, she replied that she'd be glad to do that.
After wiping out a few frozen pizzas, Betty joined the boys for some ice cream and then suggested some board games. After awhile the games got boring, but Jimmy had become aroused by Betty's braless tits. The plan of the Wilson siblings was to use Betty's well developed tits to get Jimmy aroused and that part worked beautifully.
Then Betty made the remark that it was too bad they couldn't play strip poker. Billy agreed and lamented it really was a shame. Of course Jimmy, who admitted he'd never played strip poker, wanted to know why and they told him it was backwards. To play strip poker properly, you had to have twice as many girls as boys otherwise it wouldn't work. Jimmy wasn't aware of that rule, didn't see how it could make any significant difference, but immediately began suggesting any number of girls from school that they might talk into joining them.
Billy and Betty both looked sad and told him that he was the only one allowed in the house while their parents were gone and that their aunt might drop by any time to check on them. Suddenly Betty's face brightened as if hit by a bolt of brilliance. Almost jumping in her seat excitedly, she asked Billy, "Remember that time I dressed you in my clothes for Halloween? We could dress you like a girl and then we could play." Immediately, Jimmy began begging Billy to do it and reluctantly, hiding his growing excitement, Billy gave in and followed Betty to her room, leaving Jimmy in eager anticipation.
When they returned to the den a few minutes later, Billy had become a young girl and Jimmy was in awe. Jimmy never knew the game was rigged, nor had he stopped to think about the fact that he had on fewer items of clothing than anyone else. Billy, was wearing panties, bra, slip, blouse, skirt, stockings and shoes; a total of seven items. He was ahead of his sister with six and poor Jimmy wasn't even wearing socks. He had on four items.
Billy and Betty controlled the game; often throwing away a good hand so they could loose and make a show of stripping off an article of clothing. They were afraid that Jimmy might quit if he got down to his underwear before they were nearly naked and had him worked up. So before Jimmy lost his shorts and was down to one item, Betty was sitting there in just a pair of panties and all Billy had left were panties and one stocking.
"If I loose one more hand, I'm out," Betty told them.
Jimmy panicked.
"Does that mean you have to quit?"
"Well no, not necessarily," she explained to Jimmy.
"Sometimes you can play it where after you're out of clothes, you do favors if you loose. Like if I'm out of clothes and you win and I loose, you could have me get us something to drink or dance for you or sit in your lap for a minute or something like that."
"Let's play that way," Jimmy suggested excitedly and the others agreed.
Somehow, Billy managed to loose the next two hands. When he stood to take off his panties, Jimmy couldn't help but stare at Billy's hard cock. Not that he wasn't just as hard himself. Then Betty lost and when she stepped out of her panties, she threw them to Jimmy. Then Jimmy lost and all three were naked and Betty told them, "Good, now the real fun begins." Betty won again and Billy lost and had to suck her toe for one minute.
Jimmy thought that was a funny favor until Betty stretched her legs out, pointing one foot to Billy and giving Jimmy an unobstructed view of her crotch. Poor Jimmy was sweating like a racehorse after a hard workout. Then Betty won again and Jimmy lost and she told him to put the panties on and dance for one minute. Jimmy didn't seem to mind that at all and gladly did as instructed. The next hand Billy won and Betty lost.
"Kiss Jimmy's cock," Billy told her, anxious to get things moving. If Jimmy thought the game was getting wild, he didn't complain and almost lost control. Then Jimmy won and Billy lost.
"You ought to make him suck you," Betty suggested and Jimmy immediately agreed, telling his friend that's what he wanted.
"Okay, but if I win and you loose, I'm gonna make you suck me too." Then he went straight for Jimmy's cock. He was really looking forward to doing it, had been ever since Betty had requested it weeks before, and didn't wait to hear Jimmy's happy, "Okay." That first blowjob he gave Jimmy didn't last long. They'd gotten him way too excited. But there were many, many repeat performances throughout high school and before Billy left to join the Navy.
6.
Billi Sue felt like it was his turn to get up and refill their tea glasses.
Besides, he was looking for a good excuse to waddle around in the thick, double diaper they'd put on him. He was drinking the tea as fast as feasible, trying to wet his diaper as much as possible, and both Maggie and Kathy seemed to be doing the same thing.
When he'd sat back down, Kathy told him, "Okay, now what about the Navy.
You never got to that part." Billi Sue reached across the table and put his hand on her arm.
"Sorry to disappoint you, but I really didn't take on a ship load of guys like you seem to think." He waited for a just a hint of disappointment to cross her face, then grinned.
"But computer tech school was fun! I don't think there was a single night that someone wasn't doing something with someone else somewhere in those barracks. I'd get up in the middle of the night to go pee and there'd be a couple of guys having sex in the shower. Or after lights-out on weekends when we'd had a few beers, in the dim light you might see one guy standing next to a bunk bed, sucking the guy in the top bunk, while the guy in the bottom bunk was sucking the guy standing."
"So where were you. Did you have a top bunk or a bottom bunk?" Maggie asked.
Billi Sue laughed at her.
"Top bunk. But when the lights went out, I liked to be the guy standing." The ladies seemed to enjoy the humor in that remark. Then he explained, "Seriously, there was six of us that swapped bunk assignments until we were all together in a back corner of the barracks behind the last set of wall lockers. None of us wanted to do it every night but there was always someone ready to eat some dick and someone willing to feed him. And it didn't take much, watching two guys doing it, before the rest of us would be wanting to do the same thing. So it really turned into an almost every night event."
"So if there were six of you, that's five guys plus the two you knew in school. That's seven. You have a long way to go just to get to fourteen," Kathy told him.
Billi Sue asked, teasing her, "What are you? An accounting major"? "You'd better learn that when Margaret asks for fourteen, Margaret expects fourteen," Kathy explained and when Billi Sue looked over at her, Maggie nodded her head and smiled at him.
"Okay. When I did the counting, I figured ten for that tech school bunch.
Besides the six of us, there were at least a dozen other guys that knew that if they walked back there and anything was going on, they could open their fly and get serviced. And most all of that happened the first year I was in the Navy. As best I can remember, over the next nine years, there were nine guys and it wasn't one a year like it sounds." Maggie looked at him smiling, "I think I can relate to that. You have one boyfriend or husband for several years and then a bunch in between. Did any of the guys like to dress up too?"
"Dwayne Benson," Billi Sue said without a moment's hesitation.
"Tell us about him," Kathy said, eager to hear more.
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Bill wasn't all that happy about getting orders for a second tour of sea duty. His first tour at sea had been on a ship where you had to share your bunk with some guy working a different shift. If you both happened to be off duty at the same time, you had to flip a coin to see who got the rack. By the end of that rotation, he had been ready to leave the Navy.
But he'd gotten a great shore assignment after that, made grade, and was offered a bonus plus some additional schooling if he re-enlisted. His second sea assignment turned out to be on a missile cruise ship and it was brand new and not bad at all. And best of all, he'd struck up a friendship with a guy named Dwayne on his first day aboard.
Bill wasn't sure that Dwayne was into any of the things that Bill had tried so far. In Bill's opinion, if Dwayne didn't dress up, it was a shame. In Bill's estimation, Dwayne was by far the 'prettiest' man he'd ever seen.
Over the last few years, Bill had developed a heavy interest in cross-dressing, even if he didn't get to do it much, and noticed things like men's features that would lend themselves to being feminized. Bill was certain that if Dwayne ever wanted to dress as a woman, he could pass with absolutely no problem at all.
But that was just more wishful thinking on his part. When you have sea duty, you might have one or two civvies outfits and only if you'd made some rank. Most guys couldn't bring any civilian clothes, much less a feminine set of clothes to play in. That was probably the main reason Bill hated sea duty.
He'd also found a few places at or near his duty stations where men that liked to dress congregated and Bill would try to observe as much as possible. He would notice the things that would give one of the women away as being a man and try to remember not to do that when his few opportunities came around.
They'd been at sea a few weeks when a discussion occurred that made Bill realize Dwayne may be more of a kindred soul than he'd hoped. There were five guys sitting at a table eating and one told the group that the Chief had caught two guys that morning in the infirmary having sex and they would probably be court martialed.
"What a crock of shit!" Dwayne had exploded.
"What does a guy's sex life have to do with saving the world from communism"? Then he'd realized that this wasn't the time or place to be defending gay sex and had settled down before he drew attention. But he'd certainly gotten Bill's attention. It was the first time Bill had seen or heard a word on the subject from his friend.
A few minutes later, when they were by themselves, Bill asked Dwayne, "Wonder why anyone would use the infirmary to have sex?"
"Probably because there usually isn't anyone in there at three in the morning," Dwayne answered.
Bill smiled and thought to himself, 'Bingo! No one at the table had mentioned a thing about what time the two had been caught.' Bill knew that Dwayne had knowledge of the incident that he hadn't declared. He decided to see how much he could draw out of Dwayne.
"When I was on the 'Presley' a couple of years back, the guys used to use the chain locker for that kind of action."
"That's the first place that bastard Cortez looks every night," Dwayne told him.
"He damn near caught the XO in there the second night out."
"No shit! The XO is gay? Who was with him?" Bill asked.
Dwayne smiled, blushing slightly and answered, "You don't have to be gay to enjoy sex with a guy. The XO has a wife and two kids but his wife doesn't go to sea with him." Bill took a guess.
"So you help him out"? Bill teased. He knew he was on target when Dwayne blushed harder.
"Don't blame you," Bill remarked before Dwayne said anything.
"Mr. Giles is a good looking guy." Then he walked away to give Dwayne time to think.
It didn't take long for Dwayne to figure a way to sound Bill out too.
"If you ever decide to do anything with one of the guys on this metal hole-in-the-water, you better know exactly where Chief Cortez is at." Bill knew what the sudden change in topic of their conversation was all about. Either he protested he didn't do anything with guys or let it pass, confirming Dwayne's suspicion.
"Cortez is a homophobe?" he asked, causing a smile on Dwayne's face.
"First Class," Dwayne told him.
"Probably sucked dick for his first ten years in, and now that he's close to putting in his papers, he's scared shitless his past is going to catch up with him." Bill laughed.
"He doesn't follow guys on shore leave does he? I'm looking forward to making port next week." He was hinting to Dwayne that he'd like his company.
"Naw, I think he's afraid to get off the damn boat. Know any good bars to hit while we're ashore? I've never been on this half of the world." Dwayne asked.
It was the reaction Bill had hoped for. He decided to have a little fun at Dwayne's expense.
"I found one last time that I really liked. The women there are gorgeous," Bill told him and enjoyed watching Dwayne's face sag a little before he added, "But they have the biggest clits I've ever seen on a woman."
"No shit!" Dwayne replied, his face brightening considerably.
"I've been to a few of those places in the States. You'll have to show me." A week later, the two of them were on the first liberty boat to shore and made a bee-line to "The Pink Parasol" with Bill praying silently that the place was still open and hadn't been put off limits. They were in luck. Like all bars in all ports around the world, nine in the morning was not too early to open when there were naval vessels in the harbor and sailors with American greenbacks coming ashore.
"Awesome!" was Dwayne's opening remark when they were greeted at the door and escorted to a table by two ladies who weren't making all that much effort to disguise their true gender. Several drinks later, Dwayne's lubricated tongue let the cat out of the bag.
"I can pass better than these broads," he announced proudly.
"I think I can too," Bill told him.
"The Pink Parasol" had served it's purpose for the two men and they both agreed they'd rather dress up and be with each other than one of the bar girls. It took them about an hour to gather a disposable set of lingerie for each of them, some makeup they could share, and get a hotel room. After that it was non-stop sex until they had to clean up and head back to the ship.
Back aboard, one of the guys that worked with Dwayne and was headed for shore, commented, "Hey Benson, your lips look a little puffy." Then he'd winked at Bill and continued to tease Dwayne, "Maybe it's because I haven't been to shore yet, but I swear you look prettier every day."
"Thanks for the compliment Adkins," Dwayne shot back.
"But I still aint gonna marry you. Try the girls at the 'Pink Parasol'. They're just your type."
"No shit? Thanks. I will," Adkins told them and ran before he got left behind.
"He into she-males?" Bill asked his friend as soon as they were alone.
"Yeah he is. Big time. But he can't keep his mouth shut unless he's got a cock in it. I'm certain his big mouth is what got the infirmary shut down at night. When I heard someone had been caught, I thought sure it would be him.
But don't worry. I told you I know a place where we can get it on anytime you want. We can't dress up but . . .we can still have fun!"
"Where?" Bill asked again, wondering why his friend was being so secretive.
Dwayne smiled and looked at Bill.
"Let's just say the Chaplin is a friend of mine," he said, holding up his new Bible.
Bill caught on. He'd been amazed, as late as they were running, when Dwayne had insisted they stop in town at a bookstore and find two Bibles printed in English.
"You got a lot to learn about the Navy, Wilson." Then Dwayne had told him, "First thing you do when you go to sea, is wait until you're too far out to get put on a chopper back to shore. Then go to the Chaplin and tell him you think you might be gay. Unless you've killed someone or something like that, the Chaplin can't tell anyone and either the Chaplin is looking for a little action himself or he'll put you in a workshop or something with other guys with the same 'problem'. Either way the Chaplin helps you solve your need for cock. Sort of a twist on the 'God provides' routine." Bill laughed and shook his head, looking at the new Bible in his hand.
"Maybe there really is something to this Religion thing. I remember from Sunday school when I was a kid they said that, 'God helps those that help themselves'. I suppose in this case it's true for sure!"
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"Wow! I'm surprised you ever wanted to get out of the Navy," Kathy said.
Billi Sue smiled and shook his head.
"There were some good moments I'll admit. But a year has 365 days and the whole time I was in the Navy I never averaged more than five of those three-sixty-five dressed like this," he told them, indicating his feminine attire.
"That had a lot to do with it.
And the offer Royce sent me was too good to pass up."
"Royce?" Maggie asked.
"Remember when I told you there were six of us that gathered in the back corner of the barracks when I went through computer school?" Billi Sue asked. When both girls nodded, he went on, "Royce was one of those guys. He got out after four years and went right to work in the valley - Silicon Valley. When the company he worked for offered a thousand dollar recruiting bonus to any employee that recruited someone that lasted over a year, Royce began writing to every guy he'd ever met in the Navy that worked on computers. I think at one time, we all decided that we'd indirectly bought and paid for Royce's new car."
"And what did your old cock-sucking buddy do for you guys in return? Besides get you jobs I mean," Maggie teased.
Billi Sue nodded and smiled.
"Yeah, you're right. There was some of that.
Anytime you have a room full of computer nerds, you can bet there are a few knob polishers in the bunch. But remember, we weren't all that far from Frisco and AIDS was a huge concern for all of us. Seemed to me like half the guys you met admitted to being positive and you had to wonder if the other half was lying. So maybe I was in the center of the gay universe, but I had to be very careful what I did and with who. I made contact with a bunch of TV's right after I got there and then a few of us other bi TV's in the valley started our own little splinter group and we kept our sexual activities to ourselves. We'd party on weekends or holidays with the rest of the group - go to Tahoe or Frisco or someplace and stay dressed up for the whole time. We even flew down to San Diego one weekend. A couple of us were ex-Navy and it was sort of fun to go back to some of the places we'd visited in the Navy only this time we were dressed in drag. But we only had sex with each other."
"You didn't try to get on the base dressed like that did you?" Maggie wanted to know.
"No. We weren't that brave. And we talked about going across the border but decided not to do that either. We just hit a few of the bars that were still there and then went to the Zoo and flew back. But that's pretty much an example of what I did while I was working out there. We had a little clique of guys that liked to dress up and we turned to each other when we were horny. We were sort of considered the 'sissy fairies' of the bunch, but we stayed healthy and the gay guys that teased us were dropping like flies."
"So how many boyfriends or 'girlfriends' did you have out there? If I counted right, you were up to 21 when you got out of the Navy," Kathy, still keeping score, wanted to know.
"Five. There were more that came and went. I never did everyone in our little group. We all seemed to have our favorites. Not many got in our clique. Over the ten years out there, there were a few that dropped out and a few more that joined - maybe ten total. I told you we weren't a big group."
"How many of them wore diapers too?" Maggie asked with a smirk.
"Well if you want all the details . . . ." Billi Sue told her, feigning exasperation and getting affirmative nods from both women.
"There were as many as fifteen guys in our cross-dressing group. We had a little clique within the clique of guys like me. That's the five or so I told you about.
Some of the rest were straight, and some were gay and way too promiscuous.
Of the fifteen, I think there were five or six that also enjoyed diapers but only one other guy from the group of five that I played with all the time.
And one of the guys that wasn't into diapers, but was in our little group, was the biggest piss freak of the bunch. We couldn't get him to try wetting a diaper, but he'd damn sure wet his panties or anything else and he didn't care where we were at the time. And if we weren't wearing diapers or they were full, he loved for us to pee on him." Then he turned to Maggie and told her, "If you ever hear from your college friend, 'Crazy Alice', let me know.
I think 'Donella' would be a perfect match for her."
"Sounds like it," Maggie told him.
"Sometimes I wish I could find Alice and other times I'm thankful that I can't."
"Okay, what did the five of you do when you got together?" Kathy wanted to know.
"Depends on which of the five got together," Billi Sue answered. After pausing a moment to be sure he remembered the names correctly, he told them, "Lisa and Jimi were the two that dressed up and that's about all. They were both married and one of them used to bring his wife all the time. She didn't join in on the sex, but would get hot as a pistol watching her husband suck cock. Donella I told you about and Michelle was the other guy into diapers.
And remember, this was spread out over years. I met Michelle right after I went to work out there, and we lived together for a couple of years, but then he started his own business and dropped out for a while. I wore diapers with some of the others a few times but for one reason or another, I didn't have sex with them. Donella got us an invite to a piss party in Frisco that was wild. There was a whole bar full of guys pissing on each other and drinking piss. They put a chair in the middle of a plastic kid's swimming pool and sat it on what was supposed to be the dance floor and guys would take turns sitting in the chair and letting everyone pee on them. Like I said, it was wild. But Donella and I went back to our room for sex. And for that matter, Donella didn't join our 'Clitty Club' until after Michelle had dropped out."
"Clitty Club?" Maggie asked, still smirking.
"Yeah. I don't know who started that, but that's what we called our little group. It had been going a while before I got there. I guess I'd almost have to do a spreadsheet or something to explain it exactly. During my time in the valley, I knew about fifteen, maybe twenty other cross-dressers but never more than ten or so at a time. And the 'Clitty Club' was our little sub-group that had maybe eight to ten members during my time there, but never more than three to five at any one time - plus the wives of a few that were married. We were the guys that were bi and only had sex with each other. That's where the 'Clitty Club' thing came from. We got together to suck each other's 'clitties'. That's what we called our cocks when we were dressed up." Then Billi Sue realized that Kathy was hanging on every word he said but Maggie seemed to have drifted off, like maybe she was formulating a big question. So he paused and looked at her, waiting.
"Sorry," Maggie said when she realized they were watching her and waiting for her reaction.
"I had my mind on business. I was just thinking of ways I could use what our sweetie here has told us about his friends to improve our product lines. I know we have a lot of guys buying women's things out of our 'Nice & Naughty' catalog, but maybe I should think about putting out a catalog and product line that's just for cross dressers. Maybe we could even call the catalog 'Clitty Club'." Then she reached to hold Billi Sue's hand again in the way she did to show affection and got a serious look on her face.
"I'm sure you've got plenty of business, but if you could find time to work with me on that idea, I'm sure I can figure out a way to make it worth while for you if it succeeds. Let's talk about it seriously some time next week." Just as quickly, she got the grin back on her face and her lapse into the business world was gone - almost.
"Anyway, I know what you mean. We're both in the Chamber here and probably both on committees and we've never run into each other. There's probably 50 members or more in our little Chamber and no more than 10 or 12 that ever get together at the same time. I guess all clubs or groups are about the same way in that respect."
"Tell us about Michelle," Kathy told him, wanting the discussion to stay focused.
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Billi Sue looked at the information packet and membership roster from the diaper club and wondered what the chances were of any of the members of the club he'd just joined being people he knew at work. He was aware of at least one other guy in the company that liked to cross-dress and had been told by him that there were a few others. Don had caught him the first week with the remains of polish on his nails. After that, he'd made a habit over the few months he'd been living in Silicon Valley to study other males for feminine features as well as spotting several females that he was almost certain, for one reason or another, were really men. He'd attended a party for transgendered men in San Francisco the previous month and had been amazed how many of the guys that he'd talked to were from the valley. But he really thought there couldn't be any other guys like him that liked both cross dressing and wearing diapers. Don told him he might be surprised.
Looking at the membership list, he found it was sorted by Zip Code and he scanned to the back where his area would be. Besides his own name - he'd dropped the 'Sue' but had spelled it 'Billi' and had indicated an interest in girl's clothes - he found several others in the area and if he counted in the names of those as far North as San Francisco and Oakland, there were well over a couple of dozen. Studying the list closer, he found that like a lot of the cross dressers he'd met or written to in recent years, their interests were varied. There was a mix of gay, bi, and straights. Some were into being babies and some just enjoyed being in diapers. Almost all seemed to like to wet their diapers, but some were into messing in them too.
He scrutinized that list for a couple of days, trying to decide if, and whom, he should contact. Then he got a better idea: contact them all.
It wasn't an entirely original idea. One of the 'girls' at the San Francisco gathering had contacted all of the TV's & TS's in the valley and had formed a social group where the 'girls' could get together every month for a small party.
"All dressed up and nowhere to go" had been the single most common problem expressed by everyone. Patty's group was called the 'Valley Vamps' and was for the stated purpose of social get togethers. His plan was do the same thing for the diapered community by writing to all these people between Monterrey and San Mateo and see if there was any interest in having a party in diapers.
If Billi Sue had been amazed at the list, he was even more amazed at the response he received to the letters he'd forwarded through the club. He'd hoped to be lucky enough to hear back from half of them and there were a few that didn't respond. But he'd gotten back more answers than letters he'd sent out. Several were from people he hadn't forwarded a letter to and that had surprised him.
What he'd done was write a letter, asking if anyone was interested in getting together socially for a day/night/weekend with others in diapers and he'd mentioned that if any of the letter recipients knew of someone else in the area that also wore diapers, to pass on his mailing address. He'd run off more than enough copies to mail out to everyone in the area that was a member of the diaper club and had sent the club a large package with all the letters to be forwarded inside. It seemed most of the members of the club already knew someone else in diapers and word of a possible event had spread like wildfire. He even got a letter from a couple in Chicago that both wore diapers and promised to fly out for any party he held.
And among the responses was one signed, 'Sissy Baby Michelle'. Billi Sue's biggest surprise was that the TV 'Michelle' he'd recently met had yet a third persona he enjoyed as a young girl. When Billi Sue saw the return address, he was pretty sure it was the same person. When he saw the enclosed picture and read the letter, he was certain. Michelle had an interest in being diapered and wanted to meet someone that could help him with his fantasy. Since 'Michelle' was an old friend of Don's - a college roommate as it turned out - Don had been helpful in putting Billi Sue and Michelle together for a night in San Francisco.
And within a few weeks, they were sharing a small, two-bedroom house. The fun part was that they didn't each have their own room. Instead, one bedroom had a queen size bed and was for the 'girls' and the other was set up to be a nursery.
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