by Gingerfred Man
A Pantyboy Profile
My name is Cheryl. I'm 20 years old and I'm a pantyboy.
My best friends, Judy, Amy and Sandy, are pantyboys too. Simpering little sissies made for the pleasure of nice men who treat us well.
Pretty little angels with mouths and bottoms eager for cock.
We've all been featured in our favorite magazine, Panty Boy, a celebration of all that is sissy and wonderful in the world.
I know it's your favorite publication too, Honey, or you wouldn't be reading this story.
I hope you've read "Service," where I told you all about my friend Amy and how she got to be the object of millions of men's stroke fantasies. If you didn't, that's OK, because this story about Judy stands alone. Just like your cock when you read my stories. But I'm assigning "Service" to you for homework. <giggle>
My friends gave me the task of writing one story about each of us, then one about our lives together as VERY popular sissies in New York.
You'll love this story about Judy. She's so sweet and pretty. Like me, Judy is a blonde. Her hair is long and straight, all the way to her shoulder blades. She has the prettiest three-and-a-half inch cock in the world and perfect erect nipples, framed by her bra-shaped tan lines.
But she wasn't always beautiful and desirable. Like the rest of us little cock-hungry pantyboys, Judy started life as an icky boy. Her name was even icky – Harold. If any of you readers named Harold are mad at me for saying that about your name, maybe I can make it up to you. <giggle>
Anyway, let me tell you all about Harold the Dull and how he became the little sexpot angel Judy. Get your tissues ready because it's a very stimulating story.
Chapter One – Dull
Harold's life before his 18th birthday was very dull. Contrast that with Judy's life, where she's being squired around the world by rich, beautiful men who give her things – expensive jewelry, bearer bonds, real estate, big cocks in her tight pussy. Being Judy is way better.
Harold Strokewood lived with his mother, his father having run off with his secretary or someone when Harold was quite young. His mother tried hard, but she couldn't seem to jump start Harold. He wasn't interested in girls, boys, men, women, school, movies, video games, sports or even recreational drugs. He had no friends to speak of and no ambition. Mrs. Strokewood hadn't even caught Harold whacking off or reading porn or sniffing her panties or anything that a normal boy does. A psychologist who knows which end of the telephone to talk into will tell you that there are two possible diagnoses. Either Harold had "pantyboy malaise," which meant he ached for the pantyboy condition, even though he didn't even know such an exalted state existed, or he was a jerk. Since Harold's mom didn't know about pantyboy malaise, she had concluded that the second diagnosis applied.
Harold graduated from high school the day before his 18th birthday and, since he rarely planned beyond his next meal, had no idea where he was going in life. And didn't seem to care.
Thank goodness for Mr. Stiffman.
Gerald Stiffman actually approached Harold's mother at graduation and asked if Harold would like to work for him. Mrs. Strokewood looked over her shoulder to see whom Mr. Stiffman could be addressing. Surely he didn't want Harold.
But he did. And he was insistent.
"Young Harold would be a great asset to my store, Stiffman Intimate Apparel, Mrs. Strokewood. Harold has a future in lingerie."
Well, no swami could have made a better prediction than that statement. But Mrs. Strokewood thought Mr. Stiffman was hallucinating or something about her Harold. When she realized that he was serious, she did what anyone would do when dealing with a rich person who was being careless with his assets. She took his money. Stiffman offered Harold's mom an employment package for Harold that made her eyes bug out. Though Harold was to reach his majority the next day, she knew he would do whatever she directed. Harold always took the path of least resistance, so he never argued with his Mom.
Chapter Two – The Job
The next day, Mrs. Strokewood packed Harold a baloney on Wonder Bread sandwich and drove him to work, since Harold had never gotten around to learning to drive. She kissed him on the cheek and said, "Happy birthday, Honey. Don't' screw this up."
Harold said, "OK, Mom." But what he was really thinking was, "Yeah, yeah, whatever," which is what all teenagers, pantyboy-malaised or not, think whenever a parent speaks to them.
Harold left the car and entered the store for the first time. And looked around. And felt a twinge in his gut. He didn't know why, but he was paying attention, full attention to his surroundings for one of the first times in his life. The store was immense. One floor, but as big as a city block. Like a Home Depot in size, but all girlie frillies.
Harold's cock was stiff. "How did that happen?" he thought idly as he scanned the huge room. On the left was ladies underwear – rows and rows of bras and panties and slips and camisoles and corsets and teddies. In every girlish color of the rainbow. On the right was ladies nightwear – dozens of racks of nighties and peignoirs of every size, shape, style and length. The middle was for stockings. Fully-fashioned, lace-top, patterned, fishnet, modern or traditional. With at least 100 different garter belt styles and colors. Not one pair of pantyhose. The back wall of the store was lined with shoes. The highest, spikiest, sexiest, girliest shoes on the planet.
Oh. Harold was perspiring and he didn't know why. Why was it so hot in the store? Wasn't the air conditioner working? Why did he have a funny feeling in his stomach?
His eyes weren't focusing either and he was trembling. Was he sick? He hadn't been sick before he entered the store.
He was about to run out of the store and see if he could catch his Mom for a ride home when Mr. Stiffman spotted him.
"Harold! It's wonderful to see you. Welcome to my store. Have you ever been here before? I guess not. You seem a bit overwhelmed. That's OK. Most new employees feel that way. Let's get your lunch in the refrigerator and I'll get Nancy to give you a tour.
Harold hadn't said a word. He wanted to leave. Feelings were unfamiliar to him. He rarely had feelings and they were very scary. But he wanted to stay too. He had never seen anything one-millionth as exciting as Stiffman's Intimate Apparel.
He gulped. Apparently, Stiffman was not put off by the lad's reaction. Had he seen it before?
Harold believed at that point that, as a young man at Stiffman's Intimate Apparel, he would be working on the loading dock or something. Wearing a belt with tools and a big ring of keys. He guessed that Nancy, whoever she was, would take him out back and introduce him to a burly guy named Jack or Juan, who would call him "Bud," complain about the "idiots" who ran the store, and make him do all the difficult work.
Not so. First there was the matter of Nancy.
Nancy was simply the most beautiful human being Harold had ever seen. His throat constricted when Stiffman introduced him to her and he was humiliated when he couldn't speak.
Nancy took it good-naturedly, saying, "That's OK, Harold. I get a lot of that."
Harold's eyes drank Nancy in. Long, lustrous red hair. Emerald green minidress that barely covered her stocking tops. Fabulous, long legs encased in silky, black stockings. Barely-there, strappy, black, mule sandals with an enormous spiked heel. The face of an angel. Harold's stiffie was still teeny, but it was hard and angry.
"I'm in charge of the sales staff, Harold," Nancy said. "I can see that you're going to be a valuable addition to our team."
Sales staff? Harold couldn't sell ice water during a drought. And he didn't know anything about lingerie, other than it made his dick hard. Where were the tool belt and keys? And the guy who called him "Bud?"
Harold managed to squeak out a "But, I…" but Stiffman interrupted.
"I'll leave you to Nancy now, Harold. You'll be happy here. I guarantee it.
"Follow me, Harold," Nancy said.
Nancy gave him a tour of each department, introducing him to magnificently feminine and beautiful sales associate after magnificently feminine and beautiful sales associate. Harold was reeling. How could he sell anything with them around? Customers would avoid him like nuclear waste. Was he the only man in sales? Was he an affirmative action case or something?
Despite the assault on his senses, Harold noticed two things that puzzled him deeply. First, maybe it was the time of day or something, but Harold only saw male customers. Second, Harold wasn't sure, but $175 for a bra seemed like a lot. Yet, the store was packed with customers.
When the tour was finished, Nancy asked if Harold had any questions. In response to his first concern, Nancy said that their clientele was mostly male because Mr. Stiffman had built a reputation by helping men pick out lingerie for their wives and girlfriends. Regarding price, Nancy said, "We stock only top-of-the-line merchandise here, Harold. Plus men are always willing to pay top dollar for service and consultation. Any other questions?"
Those answers sort of satisfied Harold. But there was something odd about the whole deal.
The rest of the day, Nancy spent with Harold, teaching him about the merchandise, showing him how to work the cash register and computer, and filling out his employment papers. Harold wasn't stupid, just malaised. And the new job seemed to be breaking that malaise up a bit.
Harold wasn't sure whether he preferred malaise to the sensory assault he underwent at Stiffman's. Being next to Nancy all day had him flushed and feeling a need he never knew he had. Or so he thought. Perhaps what had really excited Harold was the….merchandise.
From what Harold was able to observe, Stiffman's Intimate Apparel was a very successful enterprise. Salesgirls treated gentleman customers warmly and the gentlemen responded very well, by purchasing armloads of wildly expensive lingerie. The girls were all very beautiful, but would that be enough for all those men to open…and empty their wallets so willingly?
The last stop on the day's orientation tour with Nancy was the panty department. Thousands of panties in every size, style and color. Harold was feeling clammy and his digestive system seemed to be stirring his baloney sandwich the wrong way. Nancy was nattering on about stock and reordering and sales technique, but Harold could barely keep himself together.
The panties were wonderful!!!!
Being at the epicenter of world pantydom hugely excited Harold. In ways he could hardly imagine.
He held a gauzy little black pair in his hand and felt their silky texture. He saw the tiny red ribbons that adorned the waistband and noted the $150 price tag. And he quivered.
He heard his name and thought that a higher being was telling him something. "Harold!"
Oh. It was Nancy. She had caught him daydreaming and worse, being a little faggot who got excited by panties. She would fire him and he would never be allowed in this paradise again. For the first time in his life, Harold had recognized something he did not want to lose.
But he was wrong. Nancy was smiling. "Do you like those, Harold?" the beautiful angel said. "They're an excellent choice. Why don't you take them home? And these too." Nancy was holding up a pair of simple-but-perfect, pink, bikini panties trimmed with white lace (only $125).
Harold froze. On the one hand, he was thrilled to be able to take the panties home and "investigate" them. On the other, he was humiliated to think that Nancy would believe his first-hand thoughts were true. Did she think he was some kind of gay little dress-up princess? Well he wasn't, he thought.
Nancy seemed to be reading his mind. "It's OK to take the panties home. It's part of the orientation for new employees. We want you to be….familiar….with the products. In fact, we recommend that you try them on. Please take the tags off and use them as you see fit. They're yours. We want you get an idea of what you're selling. If you like the panties, I can fix you up with other lingerie."
Harold shuddered at the idea of wearing panties. His cock, which had been in major distress all day, was sending him a signal that he didn't recognize, but he liked very much. Still, his masculine self was obliged to say, "But I'm a man."
Nancy smiled. "Yes, but you're a Stiffman's Intimate Apparel sales professional too. And we expect you to be familiar with what you sell."
Poor Harold. He took in his breath and cried out softly. Harold didn't know what was happening to him, but Nancy did. Nancy looked away, busying herself folding panties as Harold shuddered through the first orgasm of his life. The agony almost equaled the ecstasy. He saw a bright light and walked toward it. He had no idea what happened to him or why, but he knew he liked it a lot.
Harold almost doubled over as spurt after sticky spurt drenched his underpants. In a fleeting thought, he was grateful that his mother had insisted that he wear dark trousers that morning. She couldn't have known he would……
Harold fought to regain his decorum. The last thing he wanted was to appear to be a nerd to his boss, who was also a world-class babe. Nancy seemed to be fascinated by the prospect of rearranging the panties on a rack several feet from where Harold was soaking his drawers.
Harold dried his watering eyes. There was nothing he could do about his soaked, sticky crotch except hope it wasn't too obvious. Nancy noticed when Harold was back among the living and said, "Let me wrap these samples up for you, Harold. Then you can go home. You've had a lot thrown at you today." Then she handed him her cell phone to call his mother for a ride home.
Poor Harold did so. He thanked Nancy for the "samples," then rode home with his Mom, answering her questions with the usual grunts. When they got home, he hurried to his room and locked the door. It was time to examine the samples.
Chapter Three – Sampling
For the first time that he could remember, Harold was truly excited about something. So excited that he couldn't decide whether he should first clean up the mess he made in his trousers or devour his panty treasures with his eyes.
Harold's curiosity about what had happened in his pants won out. He stripped off his trousers and threw them on the bedroom floor. He looked at his underpants. Beige, thick stains covered the front of his Jockey briefs. How curious, he would have said if his name were Alice. He hooked his thumb in the front of his briefs and pulled the elastic forward, giving him full view of his little, drooping cock. His pubic area was drenched with a sticky fluid that matted his hairs and made his cock look slick. He reached in and felt himself. Harold knew the mess was what other teens called "cum," but until that day, he hadn't given it much thought. Harold rubbed his wet, sticky cock with the fingers of his right hand. Surprisingly, it felt very good. Exploring some more, he combed his fingers through the wet pubic hairs, then reached down to see if his balls were wet. They were. And the act of rubbing his cum-slick fingers against his little bag was exciting him very much.
Eager to see and experience the panties and confident that he had done himself no harm by cumming earlier, Harold stopped feeling himself. He did pull down his underpants, however, becoming naked from the waist down. He knew he would have to hand-wash his gooey Jockeys so his Mom didn't see them, but that was for later. For the moment, he was the consummate panty professional, examining the merchandise so he would be able to perform his professional tasks professionally.
Harold considered getting a washcloth and cleaning himself off "down there," but instinctively, he knew that there would be further messes that day. And, perhaps that night.
Harold's fingers quivered as he opened the bag of panties. He saw the black teasers. Ohhhh. Then he spotted the pink ones. They were delicious too. But then he saw…..oh. Nancy had slipped in a third pair – white, satin and thronged. $195! Had Nancy said he could take the tags off and do whatever he wanted with them? She had.
It's safe to say that at that moment, Harold had never been so excited in his life.
He arranged the three pairs of panties on his bed, pink, black, white, left to right.
They beckoned him.
His cocklet had pushed through the nest of sticky, matted hairs and straightened itself again. His balls were aching. What was happening to him?
Nevertheless, he made his decision. The black panties were going on first. Right after he took off his shirt and got naked.
Harold didn't have a full-length mirror in his room. Above his dresser, he had sort of a half-length one that his Mom had insisted he have. Had he looked in a full-length mirror, Harold would have seen a fine, potentially girlish body. Slender, with slim hips and good, shapely legs. A fine bottom that was plump in the cheeks and tight in the middle. A general absence of body hair. Long, straight, naturally blond hair tied into a ponytail. Lovely, dark, large nipples that would later be the object of many men's affection. But at that moment, Harold didn't even look at himself. He was fixed on the black, bikini, see-through panties with tiny red ribbons along the waistband and leg holes.
Carefully, he removed the tags. So expensive, yet the men in the store were making them fly off the shelves.
Tags off, the panties were in their natural state. And so was Harold – naked and as rampant as anyone with a three-inch dick could be.
Harold held the panties in front of him and felt their cool caress on his naked popsy. Ohhh. He felt a thrill of sexual pleasure. What would happen when he put them on?
Harold removed the panties out of "harm's way," away from their friction upon his prick, before "that thing" happened again. But he just HAD to try them on.
He sat on his bed and, for some reason, pointed his toes as he slipped his right foot through the opening in the pretty panties. Then he slid the left foot in. Harold's legs were practically hairless, which made the voyage of the panties from his ankles to his privates and bottom a very smooth ride. Harold shivered as the wispy black treasures passed his thighs. He looked down at the waistband front's six tiny, red roses as the center two rosettes tenderly scraped the sensitive skin of his little ballbag. Ohhhh.
Pressing on, Harold eased his first panties to the top of his scrotum, then along the short, but tender length of his red, fiercely throbbing prick. With one ecstatic pull, he encased his bottom, prick and balls in gauzy, silky elegance.
Harold breathed deeply, closing his eyes and trying to regain some measure of self-control. When he had calmed a bit, he crossed the room to his mirror.
Harold was drawn to his own image. A pretty boy in black panties. The panties were so sheer that he could see his erect penis, which was so red and hot that it was almost burning a hole in the panties. He turned his back to the mirror and saw his pink bottom through the black gauze of the sweet knickers.
Harold's life was divided into the times before and after that moment.
He knew that things would never be the same for him. Thank goodness!!!
Looking at his own bottom had him frantic with excitement. If he just petted his cock a little, maybe that would help. Harold kept his eyes on the mirror's lovely rectal reflection and softly slid his fingertips up and down the gossamer material covering his drippy, mushroom head.
An image flashed through Harold's head. Someone else, of undetermined origin and gender, a dream person, was stroking his penis through his panties. It felt wonderful!!! Then, in a flash of insight unparalleled in most lives, Harold realized that, any time he wanted, he could put on panties and, with little effort, find someone who would be more than willing to stroke his penis. And kiss him. Willingly. All day if necessary.
And that thought made him gasp, then cum until his beautiful first panties were filled with hot, sticky goo.
Harold's toes curled. His pretty nipples erected and he saw colors he didn't know existed. He saw himself as a sexual being for the first time in his life. And suddenly, his life was ablaze in possibilities.
As was his penis. His panties were simply DRENCHED with hot, sticky juices and, wouldn't you know it, his mother was banging on his door telling Harold that dinner was ready.
Harold croaked out, "I'll be there in five minutes, Mom," in a throaty, sexy voice he never knew he had. Had Mom noticed?
Harold was breathing in little gasps as he put his thumbs in the panties' waistband and slowly eased them over his spent prick and balls and down to mid-thigh. He considered his pubic area. What a gooey mess! What a wonderful mess. Globs of cum stuck to everything. The beginning of a journey Harold was eager, for once in his life, to take.
Hurriedly, Harold stripped off his panties and went to the private bathroom connected to his bedroom. With a soft washcloth permeated with warm water and soap, he gently cleaned his prick and balls. Oh, he was getting stiff again, just from that. After dinner, he would put the pink panties on and see where that took him. Harold filled his sink with warm water and soapsuds and lovingly hand washed his black panties. The cum seemed to be dispersed easily, but where would he hide the wet frillies from Mom's nosy eyes? Under his bed wasn't a great solution, but it would do. He dressed quickly and joined his Mom for dinner.
Mom seemed to notice that Harold was a bit flushed. Or maybe she didn't. She asked her boy some questions about his day at work and, shockingly, he gave her some answers. Already things were better, Mrs. Strokewood thought.
Harold was a bit surprised when Mom said, "Mr. Stiffman is a wonderful man. And so handsome. Don't you think he's handsome, Harold?"
"Why would Mom ask that?" Harold thought. "Does she think I'm gay or something?"
His reply to Mom was, "I guess." But then he began to think that Mom was right. Mr. Stiffman was handsome.
Harold blamed Mom when, after dinner, he put on the pink panties, lay in his bed rubbing himself and came four times thinking not only about how beautiful Nancy was, but also about how handsome Mr. Stiffman was.
Chapter Four – First Day in Sales
Harold awoke the next morning in pink panties that were stiff with multiple cums. He rushed around cleaning up the evidence, hoping that the black and pink teasers would be dry for his "pleasure" that evening after work.
Harold was apprehensive about being discovered when he slipped the white pair on to wear under his boy khakis. But no one would know he was wearing them. Right? And he just couldn't bring himself to wear men's underwear that day.
Mom drove Harold to work and she was pleased to see how eager he was to get inside the store.
Harold put his meat loaf sandwich with ketchup on white bread into the refrigerator in the break room, then reported to Nancy for his first real day of work. Since he had taken panties home the night before, he assumed he would be working in that department. But Nancy had other ideas.
"Did you have a good evening, Harold?" Nancy asked, as they walked to the stockings and garter belt department.
Was that a little smirk on Nancy's gorgeous face?
Harold said he had checked out the panties as she had asked him to do. Then he thought he saw that smirk again.
"You'll like the stockings department, Harold. Jane is in charge and her sales are fantastic. As I told you yesterday, we don't work on commission, but Mr. Stiffman gives big rewards to the best producers."
Harold shuddered at the thought of a "big reward" from Mr. Stiffman. What was happening to him?
Nancy introduced Harold to Jane, who was another absolute feminine knockout. No wonder men shop here, Harold thought. And he was partly right.
Jane was sweet too. During the half hour before the doors opened at 10, she patiently explained the various merchandise to Harold. Then things got interesting.
Jane said, "Our top-of-the-line brand of fully fashioned stockings is called "Girlish Dreams. It's our house brand and you can see that the name and logo are at the top of each stocking."
Harold could indeed see because Jane had lifted her skirts to expose her stocking tops, garters and panties to Harold's stunned gaze. He looked away, but Jane giggled and said, "Don't be squeamish, Harold. Take a good look at what you'll be selling."
Harold looked. He saw a set of long, perfect legs, encased in the silkiest tan stockings he had ever seen. He saw a long seam along the back of each stocking, ending in a reinforced heel. The toe was reinforced as well and each dainty foot, with its perfectly polished and painted toenails was enclosed in a black, five-inch-stiletto-heel sandal mule. He saw white, creamy, hairless thighs bisected by slim, black garter straps. And he saw opaque, pink panties that looked odd to him for a reason his mind couldn't grasp.
Harold took a long, good look. Then he looked at Jane and gulped, "Thank you. I see what you mean."
Jane smiled and lowered her skirts. "Wear this for the next few days, Harold," she said, handing him a badge that said, "Trainee." "We don't want the customers to be confused. Speaking of customers, the doors are opening. You stay with me today and I'll show you the ropes."
Harold thought that Jane had shown Harold quite enough already, but he did exactly as he was told. He WANTED this job like he had never wanted anything in his life.
At 10:10, Jane said, "That Asian gentleman is Mr. Hung. He's a Stiffman's Gold Card customer working his way to Platinum."
Gold? Platinum? Nancy hadn't told him anything about that.
Harold watched Mr. Hung pick out several pairs of $150 stockings. Over his arm, he also had a $395 black babydoll nightie and two $175 garter belts.
At 10:22, he brought his selections to Jane, who smiled brightly and greeted him. "It's wonderful to see you, Mr. Hung. You haven't been in the store in a whole week. We missed you. I missed you."
There was a thin layer of sweat on Mr. Hung's upper lip as Jane continued. "This is Harold, Mr. Hung. He's our new sales trainee."
Harold felt very strange when Mr. Hung looked at him. As if he were appraising him somehow. It wasn't unpleasant. Just strange.
Then Mr. Hung said, "Very nice. Welcome to Stiffman's, Harold. Very nice."
What did "very nice" mean?
Anyway, Jane said, "So, do you have some things picked out for your girlfriend, Mr. Hung? She's a very lucky girl. Isn't it wonderful that we're exactly the same size?"
Mr. Hung smiled. "Yes, wonderful. Can you try these on for me now?'
What? Harold did a double take. He wanted Jane to model the lingerie he was thinking about buying for his girlfriend? Was that done?
Yes, but, with a few important differences from most retail operations.
Jane took Mr. Hung's purchases and said, "These are some lovely choices, sir. Let's just ring these up, shall we?"
Another double take for Harold. Pay for them before Jane tried them on and modeled them? With a strict "no returns or exchanges" policy posted prominently all over the store? Huh?
Jane and Mr. Hung appeared to know the drill. "That'll be $1,938.60, with tax, sir," she said. Hung handed her his platinum Amex, then said, a little sheepishly, "May I purchase the panties and stockings you're wearing now too?"
Jane smiled a "you naughty boy" smile, then said, "Of course, Mr. Hung. Let me just add that to your total. Oh, Mr. Hung. Just $2,848.96 and you'll be a Stiffman's Platinum Club member. Won't that be wonderful? I hope you'll remember little old me."
Mr. Hung was smiling broadly at the thought.
When Jane had rung Mr. Hung's purchases up, she asked him to sit down. She stood across from him, out of Harold's direct view, then lifted her skirts and pulled down her panties, giving Mr. Hung an excellent look, Harold imagined, at her pussy. She handed Mr. Hung her pink panties, still warm from her body. He accepted them as if they were the crown jewels. Then she unhooked her garters and slowly rolled her exquisite stockings down as Mr. Hung held Jane's panties to his nose and deeply and unashamedly breathed in their aroma. That didn't gross out Jane at all. In fact, when she handed Mr. Hung her stockings, she gave him a little kiss on the cheek. Then she grabbed his purchases and took them to the dressing room to in preparation for a show worthy of his status as a Stiffman's Gold Card member.
Harold watched discretely, but with fascination as Mr. Hung again smelled the crotch of Jane's panties, then the feet of her stockings. The poor perv was so stiff in the crotch area, Harold wondered if Mr. Hung's trousers were made out of some rubber alloy.
Within moments, Jane emerged wearing the black babydoll, a pair of the panties and a pair of the fully-fashioned stockings. She was so sexy that Harold thought that he and Mr. Hung would be riding in the same 9-1-1 van to the hospital.
For the first time, Harold noticed that there were large boxes of Kleenex next to all the seats in the store. Mr. Hung was well aware that they were there, because the customer's stiff, appreciative cock had made its way through his fly and was standing bare and proud as he watched Jane model.
Mr. Hung stroked himself softly, not wanting to cum until Jane had tried on all of his purchases. Harold watched the appreciative customer stop and take deep breaths several times as Jane turned this way and that for him in his new purchases. Jane announced when she was wearing the last outfit, so Mr. Hung began to stroke himself in earnest, assisted by a sweet, tonguey kiss from Jane, who touched Mr. Hung only on the lips and tongue and only with her lips and tongue (befitting, as it turned out, Gold Card status). When he blew his goo all over the nightie Jane was wearing, Jane didn't mind at all. Harold wondered how Mr. Hung's girlfriend would like getting a new nightie that had been creamed on. But then Harold thought, "Hey, maybe there is no girlfriend." Maybe not.
Jane scooted to the dressing room, letting Mr. Hung clean up his mess and put his big boy back in his pants. They had hardly noticed that Harold was there.
But Harold was processing what he had seen.
What did it mean to him?
The first thing it meant was pain. The stiffest and most painful erection he could imagine.
The second thing was sexual fear. Would they want him to do things like that for customers? Wearing girl clothes and kissing big, manly customers? Harold already adored panties and was thinking about cumming into his black and pink friends that night. But how could he, a man, show himself in public like that? And how could he kiss a man? With tongue?
The third thing he felt was fear for his job. The worst thing that could happen to him would be to lose the job that had given him the only reason to live he had ever felt. But, as a man, he knew he could never measure up in job performance to the set of 50+ ultrababes who worked at Stiffman's Intimate Apparel.
Out of the corner of his eye, Harold saw Jane kiss Mr. Hung goodbye, hand him his big shopping bag and approach Harold. He thought she was going to ask him for his reaction to what he had just witnessed.
Instead, Jane said, "Let me show you the dressing rooms, Harold. Follow me."
Numbly, Harold complied. He noticed that Jane was carrying packages of black and tan, fully-fashioned stockings, as well as a ruffled, black garter belt. He also noticed that the dressing rooms were unlike any he had seen at a store.
Each dressing room was soundproof and had a double bed, two wing chairs, a nightstand, a large closet, and an adjoining full bath with shower.
Jane led Harold into Dressing Room Three, leaving the door open as she said, "You need to try the merchandise, Harold. Take your pants off." She began to open the package of black stockings.
Harold shook with fear. He couldn't remove his trousers in front of this beautiful woman! But even worse, he was wearing those white panties and she would……..
"Come on, Harold. Don't be afraid. I know you're probably wearing panties. It's OK. You're just learning the job. Now I don't have time to waste, because the noon rush will be in and you need relief desperately."
Relief? Ohhh. Harold was distressed and blushed fiercely, but he removed his pants. "What Jane must think of me!" he thought. "Wearing white panties and my tiny, unmanly dick is stiff and dripping."
The panty issue was short-lived, because Jane insisted he remove his panties too, thereby permanently and totally humiliating him. And darned near completely emasculating him as well.
Which, as we know, can be a good thing.
Jane said, "You poor boy. I thought you were in this condition. Why didn't you say something? No one can work like this. Now come over here."
Jane sat in a wing chair and Harold stood in front of her. She turned him so that he was perpendicular to her, then she began to make him quite happy.
"You should never allow yourself to stay in this condition, Sweetie," Jane said. "A young man like you needs regular milking." To prove her point, Jane began to feel and cuddle Harold's privates with her right hand. Harold whimpered – something he could never recall doing before. Jane began to rub the drippy goo all around his pretty pink mushroom. "You could injure yourself. Does that feel good?"
Jane stroked Harold's pricktip sweetly for about five minutes and then, with a tiny, unmanly squeak, Harold began to ejaculate into a Kleenex Jane had positioned perfectly to catch the young man's sticky cream.
Harold was in heaven. He was orgasming while engaged with another person for the first time. And it was a job benefit.
Who needed a dental plan anyway?
Harold's face was flushed and his demeanor compliant when Jane had him sit in a chair. She instructed him in the proper wearing of stockings, including the sexy, teasing ways of rolling them up while a man is watching. "Why do I need to know that?" Harold wondered. But he did as he was told.
It put the poor, overloaded lad "on the verge" again. Rolling on, wearing and admiring one's own stockings constitute a sensual feast. And Harold was being nourished for the first time in his life. When he donned his garter belt and hooked the six straps to his stockings. Harold was needy and whimpering once again.
That time, he needed no encouragement when Jane offered relief.
Jane made things extra sweet by taking things a little further. As she caressed his tiny pole with her right hand, Jane wet the middle and index fingers of her left hand with her saliva and gently inserted the manicured digits, one at a time, into Harold's tight bottom.
Jane didn't even get to run her fingers in and out of Harold's pootie. The first anal visitors of his life threw him into a high elliptical orbit and made him cry out girlishly as he evacuated the boyish toxins from a body, awakening him to a whole new set of possibilities.
Harold loved cumming. He loved the tingles he got when sexual activity began. He loved the excitement of the acts themselves, the dirtiness of it all. He was flattered that another person would see him as worthy for a partner, especially one as dishy as Jane. He loved the warning pangs when his crisis was near, followed by the near-death experience of a full-throttle cum. The French call cumming, le petit mort, or the little death. And they would know about stuff like that.
What Harold didn't like was the way the events of the past two days seemed to be affecting his masculinity. Wearing panties and stockings, practically cumming just from putting them on, then cumming for real when he rubbed himself up a little while wearing girlie things. Those were unsettling to Harold's sense of masculinity. Even worse, he had sort of decided that he wanted to wear stockings and panties 24/7 for the rest of his life. Even in the shower.
That couldn't be a good sign that he would be the next big action hero after Arnold, Bruce and Sly were in the nursing home.
Then there was the matter of squealing when he came. Another bad omen. Real men don't squeal and cum in their panties, letting it dribble down onto their fully-fashioned stockings. Do they?
Still, even though it was emasculating, he had REALLY enjoyed every millisecond of what had happened to him thus far.
And he had a feeling that it was only the beginning.
While Harold was in his reverie, Jane wiped up his gooies and pulled his panties up. "I hope you're feeling better now, Honey. Don't you dare let yourself get so agitated without relief again. Just let me or one of the other girls know if you need a milking and they'll do it cheerfully and very skillfully. Now, get your pants back up, Harold. We have customers and there's lots more for you to learn about sales."
Submissively, Harold pulled his pants and panties up and over his stockings and followed Jane back onto the floor. The silky material of his stockings caressed his legs. The panties gently scraped his prickhead and balls. So far, he loved his job.
Harold watched Jane flirt and tease and sell a ton of merchandise to the lunchtime crowd, none of whom had achieved gold or platinum status yet. Jane and Harold took a late lunch, at 1:30, and returned to the floor by 2.
At 2:20, Harold met his first Platinum Club member – Mr. Rammer.
Jane treated Mr. Rammer as if he had just landed on the deck of a carrier and declared the quest for the perfect panty over. Mr. Rammer was clearly a VIP at Stiffman's Intimate Apparel, and he was gracing Jane with his purchases that day.
Harold was fascinated.
Mr. Rammer had a shopping cart filled with stockings, panties, garter belts, high-heeled shoes and "sleep"wear. Rammer was clearly a high roller.
Jane rang up his purchases (in excess of $4,000) then introduced Mr. Rammer to Harold.
Mr. Rammer looked Harold over very carefully, much as Mr. Hung had. But more as if he "owned" Harold or something. Harold shivered with an unknown emotion that he later understood to be sexual attraction to a man. The whole idea was so foreign to Harold that when it entered his head, his brain rejected it. But not his prick. His prick liked being looked over "that way" by a man.
Jane seemed to be wavering about something. Harold didn't know what it was. Mr. Rammer did.
"Bring your trainee along, Jane," Mr. Rammer said. "He'll learn something about sales."
Even Harold knew at that point that they weren't going to be in the back room discussing lingerie fashion trends.
He wanted to be there when whatever would happen would happen.
Harold carried the just-purchased lingerie, following Jane and Mr. Rammer to Dressing Room Five, which was an even nicer version of the room where, before lunch, Jane had made him cum and squeal – twice.
Jane felt she had to explain a bit of what was happening to Harold, so she did. Mr. Rammer seemed amused as she said, "Mr. Rammer is a Platinum Card member, Harold. That means he gets to "test drive" his new lingerie. Gold Card members get to see it on the salesgirl and they get a nice kiss as they're ready to cum. But the test drive is much more….extensive. For one thing, the member gets to watch the girl undress and put the clothes on. The rest, I think you'll figure out."
Harold was shaking visibly and he felt the beginnings of a cold sweat. He was going to see beautiful Jane naked? And so was that Rammer guy? Oh no. That feeling of intense need was back and Jane was too "occupied" to do anything about it.
Rammer said, "Try these first, Sweetheart," and he handed Jane a beautiful, wispy pair of pink panties with white lace. Suddenly, Rammer and Jane seemed to forget Harold was in the room.
Jane did an exquisite strip tease for Rammer (and almost made poor Harold, the innocent bystander, explode and implode simultaneously). Jane stripped to just her bra and panties. At that point, Rammer removed his pants and underpants, exposing a thick, wet, hard, muscular cock almost eight inches long and fiercely erect. Harold's throat went dry. But that wasn't the highlight of the interlude.
Rammer sat in a wing chair and considered the beautiful Jane. She was slowly, teasingly removing the tags from the panties Rammer had designated as her first costume. Poor Harold could have used a case of smelling salts.
Jane turned her back to Rammer and Harold, unhooked her bra, and then teasingly turned around.
The bra had been filled with forms! Jane was completely flat-chested, except for some lovely, puffy nipples that were erect with her girlish excitement.
Rammer didn't appear to be disappointed at all. In fact, it seemed to be exactly what he expected.
But then came the really big surprise.
Jane turned her back again, this time to remove her only remaining garment – the black panties Jane had put on after Mr. Hung bought the pretty things she had worn to work. Poor Harold was trembling as his mentor wiggled out of her pretty panties, revealing a bottom far beyond the dreams of mortal man. It was a perfect, heart shape, firm but promising soft delights. Harold thought, "Omigosh, she's going to turn and I'm going to see her pussy.'
Harold was only right about the turning part.
The beauteous Jane turned and Harold saw….her cock!
Jane had a cock. Just like Harold's except, perhaps even smaller. With a pretty, girlish bag of pearls dangling saucily below.
Harold cried out and Jane and Rammer turned their heads toward him. Harold was scared and humiliated. And full of apologies.
"I'm sorry, I didn't know," he said to first Rammer, then Jane.
Rammer looked at Jane, who nodded in confirmation to Rammer, who smiled at the thought.
Then the two went back to ignoring Harold. Jane slipped on the pink dazzlers Rammer had bought, then sisssied over to his naked lap. The two entered into a deep kiss and Jane placed her soft hand on Rammer's huge cock. Harold was biting his lip to avoid crying out again, trying desperately to process what was going on.
Rammer's cock was leaking sticky fluid as the couple broke the kiss. Rammer drew the almost-naked Jane to him, then kissing licking and sucking her right nipple.
Harold couldn't help it. He made the tiniest whimper and Rammer stopped sucking.
Would Rammer complain to Stiffman and have Harold fired? Tears formed in Harold's eyes at the thought.
Apparently, Rammer had other intentions. He reached over and grabbed a pair of purchased black panties and held them out to Harold. "I have another knee and plenty of panties, little one," he said in invitation.
Harold gasped. He was being invited to strip nude, put on a fresh pair of panties and then sit on a naked man's hairy thigh. A rampant, naked man, upon whose other naked thigh rested a panties-only-clad co-worker, just revealed to Harold as a male wearing women's clothes. And "pretending" to be a woman. Pretending very well, actually. She was gorgeous. So many things to process and understand. Were some other saleswomen at Stiffman's really "pretty boys?" Were they <gasp> all pretty boys?
Questions for later. At the moment, Harold had to decide whether he wanted a man kissing him and stroking his little popsy.
Harold was certain that he wanted that very much. He didn't know why. But he knew.
So he stood and, as the amorous, kissing, caressing and licking couple resumed their affections, Harold stripped naked.
Harold was afraid, but resolute. When he was completely naked, he realized that Rammer and Jane had stopped their fun and were looking at him. Rammer looked as if he were very attracted to Harold, who remembered from his mirror examinations the evening before that he had a body made for panties.
Harold blushed, but he was flattered too as he rushed to get the replacement panties on.
Jane's make-up was smeared and she seemed very heated up when Harold caught her eye. She smiled and nodded at Harold, giving him some needed affirmation.
Harold sighed deeply, then sat his pantied bottom on Rammer's hairy, right thigh.
"You're very pretty," Rammer said. Then he kissed Harold deeply.
Holy, wet tongue! Harold loved that kiss. The first kiss of his life. And it was a man who was kissing him.
Was Rammer gay? Was Jane? Was Harold? Did it matter?
Harold listened to himself. He knew that he wanted men. He knew that, like Jane, he wasn't a man. He couldn't define himself yet, but he knew who and what he was.
And he knew he liked the feelings he was getting as Rammer held his naked torso and kissed his face, neck and shoulders.
Where was Jane?
Harold saw that Jane was on her knees between Rammer's legs. She had Rammer's big cockhead in her mouth and she was giving it a good polishing with her wet tongue.
Would Harold have to do that as part of the job? He hoped so.
Ohhh. Rammer's right hand was caressing Harold's back and his left hand had entered the front of Harold's panties. Rammer's huge hand was cuddling Harold's prick and balls as their tongues dueled.
Harold was totally enraptured. He held his head back and surrendered completely to Mr. Rammer's lust. The man was a great kisser. Harold was so excited and needy. Rammer's big hand was so gentle and loving. Rammer was so excited by Jane's tongue on his cock.
Involuntarily, Harold arched his back, squeaked and began to spurt his cream into Rammer's hand, drenching his panties in his ecstasy. Rammer kissed Harold and then grunted, launching his own, debilitating orgasm. Jane's face took rope after rope of the Platinum Card holder's hot man juice. Jane, like any self-respecting pantyboy, wore her facial frosting with pride.
Harold was in love. With Rammer. With Jane. With Nancy. With his life from that moment on.
And well he should be.
Chapter Five – Judy at Last
After their little ménage a three-way, Harold looked to Jane for direction.
She sweetly told Harold to get dressed in his boy clothes (with the enchanting addition of panties, garter belt and stockings) and get back to the floor, since their department needed staffing. She also whispered to Harold that she was pleased with his development, but she needed some quality "sales" time with Mr. Rammer.
Harold wasn't sure what he should do about the cum-drenched panties he was wearing until Rammer reached his hand out and said, "I'll have those, Sweetie. Just as they are."
Oh my. Mr. Rammer certainly had his appetites! Harold pulled his cummy panties down, exposing his naked charms to Rammer and Jane. He blushed fiercely, hoping they would draw him into their naughty business once again.
Alas, Rammer was completely focused on Jane, whom he was kissing and feeling up with some relish. He seemed to be delighted at the prospect of some time alone with Jane, whom he was to "entertain" that day until just before closing time at six.
Out on the floor, Harold was visited by Nancy, who said she had been "signaled" by Jane, who had given her a very good report on Harold.
Harold looked critically at the beauteous sales chief. Was Nancy a man? Harold was too much of a gentleman to ask, though the gentleman part of him was withering quickly.
Then Nancy cleared some things up for the girlish boy. "We all started out like you, Harold. May I call you Judy, which is Stiffman's name for you? He names us all, once we accept our femininity. Recruits us all too. The man's a genius at spotting pantyboys."
"So that's what I am," Harold/Judy thought. "A pantyboy." He/she liked that name. And the name "Judy."
"May we call you Judy?" Nancy asked again.
"Oh yes, please," Judy said.
Harold had had nothing going for him. Judy would have the world at her feet. The men in the world at least.
Nancy told Judy that for the next few days, her work time would be split between working on the sales floor and learning how to project her feminine self to the world – hair, make-up, clothes, manners, voice. The morning would begin with a makeover and the day, and every day, would offer all the milkings she needed to calm herself.
Nancy added, "This will be your last night as a boy, but maybe this will make it easier." And she handed Judy a bag filled with clothes and "other things."
Judy did what girls do when they're happy. She cried.
Starting the next day, she would be one of the girls. Taking care of customers. Making money for Stiffman. And for herself.
It sounded wonderful to Judy, whose personality was developing along a completely different path from Harold's. Judy was happy and optimistic. And chatty. And eager to please. Especially men <blush>.
Ninety minutes later, when her Mom picked Judy up, Judy was hesitant to tell Mom that her son had become her daughter. Forever.
She saw Mom's car in the parking lot and scurried over. She got inside and said, "Oh, Mom, I have so much to tell you. I….."
Mom was crying. She reached out her arms, hugged Judy and said, "Oh, Judy! I'm so happy! I'm so happy that you're happy! Stiffman called and told me everything!"
Judy was stunned and delighted. She added a tributary to the river of happy tears. For the first time in many years, mother and child loved each other completely.
They yakked like girlfriends and didn't even eat their macaroni and cheese dinner until nearly 8:30.
Then Mom said, "I'll clean up, Dear. I imagine you have 'needs' to take care of."
Judy blushed. Had Stiffman told Mom to expect that Judy would be "milking" herself as well?
Oh, well. There wasn't much Judy wanted to hide from Mom at that point, but she still locked her bedroom door.
For the first time, Judy opened the bag of femmy goodies that Nancy had given her.
Oh, such lovely things! Three pretty nighties. Eight delicious pairs of panties. Four garter belts and six pairs of fully-fashioned stockings.
And at the bottom of the bag, a wrapped package that said, "Open me when you're dressed."
What could that be?
Judy washed herself up and sat to tinkle. Then she walked around the room as sissily as she could manage. Make-up was not in her playbook yet, but she did pick out and put on the sexiest pink stockings, garters, panties and babydoll.
Oh, what a babydoll! Judy's first nightie reminded her of a strawberry ice cream soda. All pink and white and frothy. Her little clitty was so hard and needy just looking at herself, but when she started imagining a man in her bedroom with her, admiring her, then kissing her all over like Mr. Rammer did! Ohhhh. The poor pantyboy was "on the verge" again.
Then she remembered the package. Harold thought packages were stupid. But Judy decided she liked packages. So she opened it. How curious. It was a magazine in a brown wrapper that said, "Open me first, read me, then open the rest." The other stuff was wrapped in a second package.
Hmmm! Judy decided to play along.
Then she noted that one item was already unwrapped – a tube of personal lubricant. Even Judy knew what that was for.
Judy took the book and the lubricant and lay on her back on her bed. Was it porn? To some, perhaps. To others it's a book of dreams.
Judy peeled off the wrapper and saw her future.
It was a glossy, 80-page publication called "Panty Boy." The "P" in the logo had a single pair of pink panties draped over it. The issue was Volume 4, Number 11: April 1-15, 2001. The cover photo was a stunner!
A lovely panty boy was wearing an ensemble of white lingerie that would have cost almost $1,000 at Stiffman's. She was made up to bedroom-seduction perfection, and lying on her back atop a frilly, girly bed. Her delicious, red, bee-stung lips were parted and her darkly made-up eyes were closed. Her adorable panties, made entirely of the sheerest, white lace, were down to mid-thigh and her itsy-bitsy popsy was in mid-cum. Her perfect tummy was a lake of hot, sticky cream, and the photographer had captured her last, curly, gooey, string of cum in mid-air. He had also captured the panty angel's expression of tortured ecstasy as her "pink purse" emptied its girlish contents for the "reader's" delight.
Poor Judy! Like ten million regular "readers" of Panty Boy magazine, Judy discovered that no one could gaze upon that picture for the first time and keep his or her cum in its bag.
The sweet angel heaved her cummy load from her little balls, soaking yet another pair of expensive panties. She whimpered and moaned as she thought about the men who would look at that picture and lose their manly, liquid cargo. At that moment, Judy formed the intent to grace the cover of "Panty Boy" magazine someday. Which, as we all know she did. OK, twice. To my once. But mine was a lot better. All the men I take to bed say so.
Anyway, Judy's little nutsies almost blew off and she hadn't even opened the magazine or used the lube yet. The lube turned out to be superfluous, because, after the first cumstorm of the evening, there was plenty of moisture to go around.
When Judy had calmed herself a bit, she looked at the cover picture again. The magazine's sissy doll was doing something extra naughty. In her right hand, she was holding one end of a long (two feet, at least) cylindrical object that was made out of clear, gelatinous, and firm-yet-supple material. Judy looked closely. The end she could see appeared to be shaped like a <blush> cockhead! She couldn't see the other side because it appeared to have been pushed into the pantyboy's pretty bottomhole! Judy gasped! How was that possible?
Judy remembered fondly how Jane had put two fingers into her bottom earlier that day. It had been delightful and it made her cum hard. But Jane's fingers were slim and that "thing" appeared to be about the size of Mr. Rammer's cock!
Maybe it was an illusion. Maybe it was only in her bottom a little bit. Did men put their things into pantyboys "back there?" Did it hurt? Did the pantyboys like it?
Aside from being terrified that she would be halved by an overenthusiastic lover who wanted to run his business in and out of her "dirty place," Judy was very excited by the idea. Pantyboys could be fucked like women! On their backs with their men rutting and grunting. Surrendering to their men.
She was stiff again.
Judy opened the magazine. The first "pictorial" was called "Your Cheatin' Heart." Yes, it was a Hank Williams song, but it was an odd name for a pictorial.
It was a story in pictures, beginning with a young man who was a college student, sitting in class, then going home to an apartment no college student could afford.
Slowly, lovingly, the pictorial showed the transition from 18-year-old male student, to the dazzling pantyboy depicted on the cover. Picture by picture, it showed him strip to a lovely nude, then sit at a vanity table and make himself up into a pantyboy the magazine called Anne. Even nude, Anne oozed femininity. The first full-frontal shot where a stockinged, heeled and gartered Anne is hooking on a white, lacy bra, the reader could see the girl's tiny tinkler. It looked erect and needy to Judy, who was finding that she was attracted to her sister pantyboys, though not nearly as much was she was to men.
Judy, who had yet to suck a cock, ached to do so.
Anne dressed completely in a white lingerie ensemble. Judy thought that Anne must be about to "entertain" a man, since it seemed like a lot of trouble to do all that for oneself (notwithstanding the fact that Judy was guilty of that, less the make-up, that evening).
But Anne seemed to be meeting another friend. A plastic one. The huge, long cock-substitute from the cover photo appeared and Anne took it to bed with her. After carefully lubing seven inches of one end, Anne gave clear evidence of the disappearance of all seven inches.
Judy's eyes were wide as she saw Anne take the entire business with ease. No, beyond ease. With relish.
Could Judy do that? With a man's real cock?
The next six photos showed the gut-busting orgasm depicted on the cover, spurt by cummy spurt. Then Judy added four thick spurts of her own. Thank goodness she had removed her panties. They were already at maximum permeation.
Judy's head was filled with visions of real men with real cocks putting them into her – to their mutual delight. If it didn't kill her first.
Judy moved on through the magazine. After the monster cum, the phone rang and dialogue was added to the story. Using a "split screen," Anne was on the left and a strikingly handsome and manly fellow was on the right. The man was in what was obviously a hotel room. He was wearing blue silk pajamas, but had fully unbuttoned the top, revealing a hairy chest and six-pack abs. He had unbuttoned the crotch of the pajama bottoms to reveal – oh my – a painfully erect cock that went up to and PAST his belly button. His hairy balls were almost the size of a brown lunch bag. And he was seriously CUTE!
Whew! Judy was erect again. "Shouldn't this magazine come with a warning label?" she thought.
The panty princess in the magazine asked, "When are you coming home, darling? I miss you so much."
The man said, "Day after tomorrow, Honey. I miss you too, Baby. I love you so much. All I can think about is making love to you."
The two engaged in some mild phone sex for two pages and then, "Wham!" Anne spurted her cream all over herself, as she professed her undying love for "Brad." Then Brad winced and flung man-sized globs of thick juice all over himself. Judy, of course, joined them.
If she could only meet someone half as cute as Brad, she thought. (Later, when she did her first shoot for Panty Boy, she and Brad had a white-hot, little, three-week affair. So did I. He was great, but Judy and I knew we could do better.)
The picture story concluded with a lot of phone kisses and promises. Anne hung up the phone and the full page went back to pictures of her. She removed the big toy from her bottom and threw it away. She held her arms open and…..[turn the page], was joined by a very good-looking, very naked gentleman who climbed atop Mount Anne, hoisted her legs and gave her what pantyboys crave. A good, stiff fucking! Judy wondered, where did that "Brad pinch hitter" come from? Did Anne have men lined up around the block, waiting to fuck her should the opportunity arose? Apparently so. And how did she get mystery man's huge cock into that tiny hole. And why was she cumming all over herself as he fucked her?
Questions that Judy was pretty sure she would enjoy answering as soon as possible.
She turned the page and saw that Brad was also a cheater! A tasty little Asian doll with a stiff, two-and-a-half-inch popsy, a lovely smile, miniscule black babydoll, and black, fully-fashioned stockings had joined Brad on the bed. In the next picture, she was kissing him and her petite bottom had consumed the entirety of Brad's fat friend.
How was that possible?
If she could do it, couldn't Judy?
The other package!
Judy got out of bed, drooling cum down her belly as she crossed the room to retrieve the package from the box. It was flat and long. Judy opened it and saw – a replica of the two-foot-long, dual-headed, prick-like toy from the magazine.
She could lube it up and slowly insert it into her tight, pantyboy-virgin pussy. Just to see if it fit. Sort of a science project.
What if it didn't fit? Judy would be drummed out of pantyboydom. Her panties would be confiscated and she would have to wear cotton Jockey briefs for the rest of her miserable, manly life.
Maybe not, but Judy knew she would feel a lot better if she could get about five inches or so of that sissypleaser into her pootie.
Judy was trembling a bit when she washed the whole, big sausage in the sink, with soap and water. One must take some precautions with what one sticks into one's "special place." She dried her imminent deflowerer with a towel, then took the "instrument," the tube of lube, and "Panty Boy" to bed, placing them at her side after she lay down on her back.
Judy set up the pillows just as she liked them. Her room had to look its best for the crime-scene photos and the nightly news: "Pantyboy halves self with ridiculously long, ersatz cock – film at 10."
Judy lubed about six inches of the end with the smaller "cockhead." Then she opened the magazine to check out the positioning and grip Anne used to impale herself.
She placed the intruder at the wrinkled gate to heaven, drew her breath in, then eased the head past the tight ring.
Kind of nice.
She pushed in an inch and gasped a little. A little discomfort, no pain.
Another inch. A big pinch. The first real unpleasantness. Judy rested. Her cock, which had drooped from her fear, was starting to twitch in appreciation.
Slowly, Judy pushed with steady pressure, embedding the other three lubed inches. That hurt a bit, but it passed. Judy held the other end of the penile simulator and decided to do her own test drive. She pushed and pulled the hard-gelatin material in, out and sideways, simulating a good fuck as well as one can without a man in the room.
That, she liked. So did her pricklet. It stiffened. Her breathing quickened. She closed her eyes and pretended that a man like Brad was on top of her girlish body, pushing and grunting as he worshipped and adored her. She was close. Her dream man was close. Her dream man cried out! Judy screamed! Loudly and shrilly. But her sticky juices didn't come out. Had she broken something down there? She was in sexual distress but wasn't cumming. Where was …..ahhhh…..the big thing in her bottom, rubbing on her prostate, had delayed the juices. But hadn't abated them. All of a sudden, the impediment collapsed and her cum was gushing as Judy doubled over in sweet anguish.
Actually, in one way, the timing was perfect. Judy's mother, who responded to Judy's orgasmic scream, thinking that she was being murdered, flung the door open just in time to see her "son" in full pink lingerie, anus stuffed with a cock-like device, gushing cum from a tiny, stiff prick.
We all need material to tell our psychoanalysts. Why should we bore them?
Chapter Six – Employee relations
Judy's career and the "real' part of her life began in earnest the next day.
Mom kissed the still-boy-dressed Judy as she dropped her off at work. Judy had no regrets about the fact that she had put on boys' clothes for the last time that morning. When the boy clothes came off, the whole lot was going to charity.
Judy was tingling with excitement and curiosity. How would she look after the makeover? Would she be up to Stiffman's Intimate Apparel standards?
Oh yes, ladies and gentlemen.
Stiffman's ran a beauty parlor operation for its "girls." Open two hours before work and four hours after, it was an employee benefit that had a direct impact on how many customers came through the door and how much they spent. So it was a first-class operation.
Delma, one of Stiffman's ace beauticians, was on overtime duty (during Stiffman's retail hours) to do a makeover for Judy, the new girl. Delma gave Judy "the works" and instructed her in how to do her make-up and touch up her new, blonde hairstyle. It took five hours, but the results were spectacular.
Judy herself was astounded at her girlish beauty. She was made-up, manicured, pedicured, ear-pierced, powdered, perfumed and dressed in a perfect little black dress that highlighted her body's assets. Judy could only manage two-inch heels at that point, but they still made her bottom begin to jut out the way men adore.
When Judy stepped out on the floor, even her coworkers stopped what they were doing to admire Judy's beauty. I'm not exaggerating. Only four girls have ever been on two Panty Boy covers – one was Judy.
Judy was feeling completely on top of the world when she reported to Nancy for an assignment that would cover the last three hours of the day.
Nancy gasped. "Oh my, Judy," she said. "Stiffman will be able to build a new wing on his mansion from all the lingerie you'll sell for him."
Judy blushed. She ADORED being the complete center of the universe. What a change from Harold's life.
"So where am I selling today, Chief?" good-soldier Judy asked.
Nancy said, "Nowhere today, Honey. Mr. Stiffman always gives the new girls an 'orientation' on their first girlie day, right after their makeover. Don't worry, he called your Mom and explained. He'll also be with you for breakfast, if you get my meaning."
Judy got it. Mr. Stiffman was going to give her several good, stiff fuckings most of the night. That sounded wonderful to her.
Nancy asked, "Did you use all the stuff in that package I gave you last night?"
"Was it OK? No bad pain?"
"A little, but then it was all pleasure."
Nancy hugged Judy and wished her good luck.
Then she escorted her to Stiffman's office. "Always knock before you go into his office, Judy," Nancy said. "Sometimes he's 'consulting' with the sales staff. He often 'consults' with the sales staff."
Judy blushed. What a great place to work.
Nancy hugged Judy and left. Judy knocked.
"Come in," a manly voice said.
She entered and was delighted at Stiffman's reaction. Even he, who had selected, employed and bedded dozens of panty boys over the past 18 years, was impressed by Judy. More than impressed. Smitten.
"Judy!" the astonished, delighted and stiff man said. "You're incredible! Can I pick 'em or not?"
Just like a guy. Giving himself credit for Judy's beauty. Though it was true that almost no one in the world would have seen Harold as anything other than Harold.
Judy knew that she owed a huge debt to Stiffman. She was more than happy to pay her debt.
Stiffman's eyes were still wide a minute after he first saw Judy. Was he drooling? He seemed frozen, so Judy said, "Mr. Stiffman, you've made me a very happy girl. How can I ever repay you?"
That's what men call, "Something we like to hear."
Stiffman said, "Just come over and sit on my lap, my dear. Let me drink in your beauty as I smell your perfume."
The fly was eager to join the spider, but she had an idea first. "But it's so hot in here, Mr. Stiffman. Can I take my dress off, please?"
"Nice," Stiffman thought.
"Of course, my dear," he said. "If you really want to make me happy, I would love to see you in just your Stiffman's Intimate Apparel, high-quality, European-import panties."
In answer, Judy giggled and bit her knuckle. Then she asked Mr. Stiffman to unzip her. Slowly, teasingly, Judy stripped to her sheer, black panties, which were imported from Wisconsin, cost Stiffman $3.56, and sold for $185, a tidy 5,197% markup.
Stiffman liked his girls in just their panties. They were so girly and submissive when they were reduced to the bare essentials. It was also good for their morale, helping them understand that it was their beauty and personality that made them girls, not their clothes.
Judy looked very girly in just her panties. Her feminine confidence was growing, and her red toe- and fingernails, gave her an extra burst of sissiness.
Veteran pantyboy lover that he was, Stiffman knew that Judy was special. She looked dazzling, even without those overpriced clothes he sold.
She looked so good that Stiffman changed the plan. Judy had almost reached the sitting Stiffman when suddenly, he stood. "Come with me, Sweetheart," he said, taking Judy's hand.
Submissively, Judy complied.
Stiffman took Judy through a door and into a lovely, manly bedroom where Stiffman had spilled a few gallons of goo over the years.
Stiffman said, "Do you trust me, Judy?"
Judy nodded. She was very excited.
"Then lie on the bed, on your back, with your arms over your head, and let me make you happy."
That sounded awfully good. Judy did so. She wanted to give herself, completely and submissively, to a man.
Stiffman looked at the almost-naked, submissive angel with great anticipation as he stripped naked.
Judy whimpered with lust when she saw Stiffman's hairy chest and big cock.
Her hands remained above her head when Stiffman joined her on the bed. He lay on his left side, his large, right hand rested on Judy's tummy as he kissed her sweet lips. Judy was hungry for his kisses, but her balls ached for release. The poor pantyboy hadn't cum since Delma the beautician milked her by cuddling her babyballs four hours earlier.
Stiffman offered Judy his tongue and she reciprocated. Then he went "panty-fishing" for Judy's pretty little "worm." He kissed her tonguily as he gently tickled her pricklet. Judy felt a tingle in every pore of her body. Especially her nipples.
Her little nubbies were erect and aching as Stiffman licked her tonsils. His fingers were giving her an excellent feel-up, even though her panties were still on. She wanted to feel Stiffman's excellent prick, but her arms were still submissively positioned over her head. The poor pantyboy was gasping and panting as the man took charge of her completely.
Stiffman stopped kissing the panty angel. What would he do next? Judy was powerless to stop him!
The nipples. He was going for the nipples. Every pantyboy's vulnerability. Judy's nips were as stiff as tiny pricks and alive with need when Stiffman began to adore them with his lips and tongue.
Judy screamed. Thank goodness Stiffman's door was soundproof.
He was….oh….so brazen and so masterful. He could torment her nipples for hours if he wanted and she couldn't stop him. She was just a weak little girl who needed a man to show her the path to paradise.
As you can see, Judy and Stiffman were both living out major fantasies.
Judy's only thoughts were of Stiffman's hand doing whatever he wanted in her panties and his lips and tongue commanding her nipples. Was such intimate pleasure possible?
Judy was moaning and whimpering for several minutes, trying to hold back her cum. Enjoying the process too much to rush to climax. Stiffman was sensitive to that. He would bring her to a leaky peak, then ease up. He would take her near the edge again; then draw back. She held her head up, eyes wide, to observe her carnal master. He was magnificent. Lean and fit. Handsome and hung. And so skilled.
Her first man. Rammer was an appetizer. This, she hoped would be seven courses.
No one can hold back from an erotic onslaught forever. Judy's whimpers told Stiffman that this was the last go-round for teasing.
So the bad boy did something Judy never expected. He pulled only the front of her panties down, exposing her pricklet and little bag. Then he straddled her knees and gently and lovingly took her fiery popsy into his wet mouth and began to run his tongue around her little velvet knoblet.
Poor Judy. That was all she could endure. She squealed and began to pump hot girly juices into her boss's loving mouth. Stiffman devoured the creamy treat greedily, tonguing Judy's privates throughout her ecstasy to prolong her pleasure.
Judy liked Mr. Stiffman.
And Stiffman liked Judy.
Good employee-employer relations are an essential part of business success.
Stiffman licked Judy until her spasms quieted, then he moved up to give her a big, cummy kiss, holding her in his arms and encouraging Judy to do the same for him.
Their kissing was exquisite and lengthy. And very exciting to them both. Judy's prick was stiff and red again as Stiffman rubbed his thick, hot weapon against her pretty jewel.
Judy realized that the poor man had had no relief, so she begged for the privilege of taking his cock into her mouth – her first.
Stiffman insisted that the privilege was his, then he sat on the side of the bed and spread his legs wide enough to allow the kneeling pantyboy complete access to his considerable assets.
Judy blushed as she thought about her situation. She was kneeling before a man's cock. Her panties, which were her only garment, were soaked with her cum and had been pulled to mid-thigh. Her bare bottom was resting on the back of her calves and her pricklet, despite some recent, delightful, sticky explosions, was throbbing with want.
Well, that would have to wait! Judy's priority was to relieve her poor boss/lover's obvious needs.
It was a big step, taking a man's cock in one's mouth for the first time. Big step. Judy gave the object of her affection a good look-see. Big and hot. Lots of goo leaking from the pretty peelips. Two blue, prominent veins. Big testicles in a large sack. Heavy with juices.
Judy knew her destiny. A pantyboy always knows, though she may deny it for some time.
She pressed on. Judy rubbed and inspected and fondled every square centimeter of Stiffman's first-rate equipment. Stiffman demonstrated amazing cum-control as the pretty sweetheart's gentle fingers caressed his parts. But even a cocksman as experienced and skilled as Stiffman couldn't endure too much more.
Fortunately for them both, Judy began to involve her mouth in her pubic explorations.
The lovely angel kissed the pink, sopping arrowpoint of Stiffman's weapon. For the thousandth time, Stiffman thanked his father for retiring early and putting him in charge of what was then a tiny, subsistence lingerie store that catered to (if you can believe it) women! And Stiffman thanked his own common sense for "repositioning" the store the way he did. He was making nearly a million a year and fucking the world's prettiest pantyboys whenever he felt like it. Which was all day every day.
Why do men play golf when there are pantyboys everywhere eager for "attention?"
Judy extended her tongue and began to lap up the copious juices that had formed along Stiffman's thick knob and the long shaft. Her tongue was wet and enthusiastic and she was delighted when she made Stiffman moan. It's good to get feedback and reassurance.
Judy cuddled Stiffman's balls with her left hand as she kissed and licked and sucked her man's cock. Almost as one would scratch an itch, reflexively, she began to stroke her own little business with her right hand.
Stiffman said, "So good, Baby. So good. You're a natural. And so beautiful!"
A line? Maybe. But it enhanced an already delicious experience for Miss Judy.
The intimacy and dirtiness and tastes and smells drove Judy to savage her own peener as she sucked Stiffman's mushroom with her great aplomb.
Was she going to………… Was Stiffman going to………
Yes and yes. Judy's mouth was covering Stiffman's knob as he cried out and came. Judy tried valiantly to swallow the entire "girl's big reward," but some dribbled out of her mouth onto her cheeks. That man could cum!! He spurted his juices five times by Judy's count and her face was coated with about half of her man's evidence of excitement.
Judy's own popsy began to explode during Stiffman's third spurt, and she pumped thick ropes of hot cummies onto Stiffman's bedspread.
In that instant, Judy achieved a moment of clarity that few of us ever attain. She knew the kinds of things she wanted to do the rest of her life. Judy wanted to be a pretty, girlish, hot-dressing, sexy, submissive, teasing, pleasing, man-loving, little pantyboy creampuff.
And she hadn't even had a big, hot visitor in her bottom yet, though it appeared that visiting hours could begin at any moment.
Stiffman collected Judy into his arms and spent the next half hour kissing her and telling her how precious and beautiful she was.
No pantyboy can resist a loving man in full kiss-and-praise mode.
Nor one who has decided to enjoy the pretty pantyboy's anal recreation facilities.
Stiffman began the sweet doll's deflowering process by laying her on her stomach and removing her pretty panties completely. Judy lay there, naked and wiggling her plump bottom provocatively. Would Stiffman just mount her and fuck her immediately?
Nothing so crude. Stiffman was a gentleman. He would eat her pussy first.
Stiffman knelt between Judy's spread legs and rubbed her bottom with his massive hands. He was so big and strong, but so gentle. The man knew how to love a sissy.
Judy was panting and rubbing her re-stiffened poppet into the mattress as Stiffman kissed her pretty bottomcheeks. When he parted her soft globes with his manly thumbs and began to kiss and lick the warm inner folds of her bottom, Judy squealed and thanked fate for delivering her to Stiffman's tender care. When he dug his wet tongue into her anus, Judy left the planet, just as her sweet cream left her pink bag.
When Judy's pretty pussy was sopping from Stiffman's saliva, the considerate gentleman entered the virginal pantyboy's pootie with two thick fingers. Running them in and out. Stretching her. Opening her for his cock. Then rubbing his fingers against her tender, girlish prostate.
All the air left the room. Judy's throat constricted. Her body stiffened as yet another sticky load left her sissy body. As she hurled juices from her poppet, she felt her man mounting her from behind. He was going to put his big thing in her! Right then. While she was cumming for goodness sakes.
Judy felt Stiffman's weight on her then his cock was rubbing between her plump buttocks. He rubbed his rammer to wet it with her sopping anal regions. Then he aimed his weapon at Judy's magnificent anus and PUSHED.
Judy screamed with equal parts pain and rapture. That big dong was so much stiffer and hotter than that "simulator" she had used the night before. And so much better. Stiffman paused to let Judy adjust to her new "guest." When she croaked out a "Please sir, may I have more," Stiffman twisted and pushed and pulled and made Judy and her bottom very happy.
Judy loved being fucked.
She couldn't wait to see where her new everything (name, gender, clothes, personality, desirability, sexiness, sexual-orientation, and girlishness) would take her through life.
Chapter Seven – Further Development of Retail Skills
The next morning Judy's bottom was full of cum and her heart was full of resolve to be the girliest girl and the best salesperson in the glorious history of Stiffman's Intimate Apparel.
It had been an exhausting night. Stiffman was a totally naughty boy. Five times poor Judy's formerly virgin hole had been stuffed and creamed.
It was heavenly!
But Judy was eager to show the world her new femininity, just as she had shown a smitten Stiffman when she took his last big, sticky load in her face at 7 a.m.
Stiffman liked money almost as much as he liked pantyboy pussy, so he would not detain Judy from her sales duties. In fact, when Judy had showered, shaved, powdered, perfumed, accessorized and dressed, he pulled her panties down and gave her a lovely, good-luck clitty-sucking to set her on the path to sales success. Far better motivation and affirmation than one could ever get from a lecture or an infomercial.
Judy strode out onto the retail floor that morning with new, girlish confidence. There was a whole world of men out there who wanted to take out second and third mortgages so they could buy hugely overpriced lingerie from a pantyboy, and she wanted to be the creampuff to sell it to them.
Of course, Judy needed to call her Mom first and reassure her that she was still in one girlish piece after a night with a master cocksman. The two giggled like schoolgirls as Judy told Mom about the strange little noises Stiffman made when he was cumming.
"They're all little boys at heart, Judy," Mom said. "And we're their toys."
One of the nicest things about Judy's acknowledgement of who she was would be a real bonding with her mother.
Even the other salesgirls' heads turned when Judy clacked onto the floor in her first three-inch heels. She hoped the seams on her fully-fashioned black stockings with reinforced heels and toes were straight. She had inserted a tampon in her cummy bottom and hoped that it wasn't leaking mannish juices onto her purple miniskirt.
Oh well, she thought. She had earned those mannish juices, so she had the right to display them.
When she reported to Nancy for her day's assignment, she was happy to hear that she would spend the morning in the stockings and garter belt department, and the afternoon in femininity instruction. Judy liked Jane and she was eager to hone her sales skills.
Jane greeted Judy warmly, with a sweet kiss and darned if that lumpiness didn't return. It seemed to Judy that randiness and erections would be her constant, lifelong companions. How lovely!
Judy thought that Jane was about to take her back to the dressing rooms for some "relief," but the store's doors were opening and it was time to focus on business.
Business. Judy was all business.
Fridays were a busy day at Stiffman's. Guys buying lingerie for their girlfriends for the weekend, perhaps? Guys buying lingerie for themselves for the weekend? Or guys just wanting to ogle the lovely pantyboys?
Anyway, by 10:45, Judy had sold over $3,000 in merchandise to guys who just wanted to breathe the same air as Judy.
Then Mr. Footman arrived.
Jane greeted Mr. Footman very warmly. He was a Platinum Plus member, having achieved platinum status the past 18 consecutive years, which meant he had spent at least $2 million at the store. That's more than 11,400 pairs of stockings, garter belts and panties, the only items he ever bought. Judy thought, "That's two items a day for 18 years. He must have a lot of girlfriends."
Jane introduced Judy to Mr. Footman and she blushed as she saw the naughty look in his eyes.
Jane said, "I believe Mr. Footman would like you to model his purchases for him, Judy dear."
That certainly appeared to be his intention as Jane rang up his purchases.
Judy was blushing when she led Mr. Footman to Dressing Room Five. The way he was looking at her! Where did she get such power to cloud men's minds?
When they closed the door, Mr. Footman removed his trousers and took a seat in the wingchair. Judy shyly peeked at his cock. It was cut, red and very stiff. A nice, average, six-incher.
Unsure of what was expected of her, Judy asked, "Would you like me to try these stockings on for you, sir. Or is there some other way I can help you."
Footman smiled. "Just strip to your bra, panties, garter belt, and stockings, Sweetheart, and sit on that chair across from me. I've bought the stockings you have on too."
Judy gulped a little. She was excited and a bit scared, though she knew that all she had to do was scream and a security alert would activate, flooding the room with assistance. She doubted she would need that kind of help, though.
Judy made her stripping into a little tease show, pointing her foot for him as she stripped, showing little bits of herself at a time. Footman enjoyed it very much.
When she was down to her "undies," Footman beckoned her to sit across from him in the other chair. "You're very lovely, my dear," the Platinum Plus member said. "May I just hold your pretty feet in my hands and caress them?"
"No" didn't seem to be in Judy's vocabulary. Shyly, she extended her stockinged feet to Footman's eager embrace.
"Beautiful, just beautiful," he said as he stroked the seam along Judy's right sole. "Has a man ever done this for you before?"
"No sir," Judy managed to squeak out. It was amazing how aroused Footman's loving attentions had made her. Footman was very good at foot massage. Maybe he did have enough girlfriends for 11,400 items of lingerie.
"My dear," he said, "I wonder if you could do something for me. I would very much like you to rub my penis between your warm, stockinged feet until I spurt my juices all over your little pretties. Would you do that for me? I promise I'll make you happy after you do."
That sounded so DIRTY! Just what Judy liked.
She eagerly agreed, then got herself into a comfortable sitting position where she could extend her legs and rub the man's stiff soldier between the smooth nylon that covered her warm feet. Judy loved how Mr. Footman reacted when she tentatively touched his hot shaft with her right toes. The man loved it. When she added the other foot and rubbed the shaft between them with a horizontal motion, she loved how he grunted and closed his eyes.
It was fun!
And Mr. Footman certainly seemed to be enjoying himself as well. When Judy moved her feet up his shaft and began to slowly, sensuously rub the gooey knob between her stockinged soles, Footman cried out. Big gushers of goo leaped from his peehole and drenched Judy's toes and feet. His sperm was so hot that Judy almost pulled back, but she was a professional sales representative of Stiffman's Intimate Apparel. So she rubbed the man's big mushroom between her feet until the entire pint of hot juice had been expended.
Judy kept rubbing until Footman's eyes opened and he asked her to stop. "That was delightful, Darling," he said. "You're a perfect angel, made for love."
Wow. A few days ago, she had been Harold, a perfect loser, made for failure.
Footman took Judy on his lap and kissed her deeply, with lots of tongue. He reached into her panties and, feeling her neediness said, "Please take your stockings off, Honey, and give them to me. Then I'll make you happy, as I promised.
Judy hoped that Mr. Footman would fuck her. Goodness knows, she felt as if she needed it. But he had other plans.
Mr. Footman had a special bag for the cummy stockings. Judy was about to put on a fresh pair when he said to her, "No, Dear. Just lie on your back on the bed."
Judy would have felt girlier if she had worn her stockings for the anticipated fucking, but Mr. Footman WAS a Platinum Plus member.
Like the little tramp that Sandy, Amy and I know Judy is <giggle>, she spread her legs in invitation to Mr. Footman. But he stood at the foot of the bed and began to caress her bare, right foot.
"So delicious," the foot connoisseur said. "An excellent manicure and a lovely shade of nail polish."
Then he brought her foot to his mouth and began to kiss, lick and suck….no make that "adore"….. each toe.
Holy moley! What was the number of the truck that hit Judy?
What was that crazy, wonderful man doing? He was worshiping her feet. VERY well. It felt so……. Oh. Judy couldn't be cumming just from that. But he was so……… Oh. She WAS cumming. Hard. Wrenching. Filling her panties with hot, sticky spurts. How scrumptious! How unexpected.
When Judy had calmed down, Footman asked that Judy remove her panties. She scooted out of them and he bagged them for "home use" as well. Then, finally, he did something "normal." He licked and sucked up every drop of cum from Judy's privates and then gave her a thoroughly delightful prick licking until she came, squealing, in his mouth.
Judy figured that there was no limit on the time a Platinum Plus member could "occupy" a salesgirl, and she was right. The nice man only asked that she put on a pair of tan stockings and, while lying on the bed on her stomach, reach back with her feet and give Footman's cock a good rubdown, as he viewed her seamed soles. That went on very pleasantly for about 20 minutes until Footman gasped and blew another gusher onto the pretty girl's footsies.
Same drill. Bagged cummy stockings. Big kiss. Then Footman went home and Judy went off for her lunch break.
It was an odd place to work, but it had its rewards, including the two one-hundred-dollar bills Footman slipped into Judy's bra as he kissed her goodbye.
If you have to work, Stiffman's is a good place to do it.
The afternoon was spent with Karen, a lovely sales associate from "sleep"wear, who gave Judy some excellent instruction in make-up technique and hair styling.
She also gave Judy some useful answers to questions Judy had been pondering.
"Of course we're allowed to date the customers, Judy," Karen said during a mid-afternoon "milking break."
Karen waited until Judy had finished tickling Karen's testicles and stroking her knoblet until she spunked. Then, as Karen began to run two lubed fingers in and out of Judy's sweet little "pussy," she said, "We're encouraged to date customers. The girls, management and the customers are all part of a wonderful community here. The customers are very good to the girls and we're good to the customers. Some of the girls even marry the customers. Most of them."
Oh. Judy's pricklet twitched at that. She had never thought about how wonderful it would be to be a man's bride! His possession for life. Complete submission to him as her lord and master. And to be in a wedding gown – the beautiful center of the universe's attention. Followed by a honeymoon where she would do every dirty thing her husband asked.
Judy's poor balls exploded as she pictured herself as a wife. Someday, Judy will marry a man. Amy, Sandy and I all will. Goodness knows we've had thousands of offers. Sooner or later, we'll each accept one.
At that moment, marriage was a lovely, exciting idea for Judy.
That night, Mrs. Strokewood set a pattern for their future together by helping Judy practiced her make-up technique and gave her some good tips on feminine mannerisms.
Mrs. Strokewood was deliriously happy to have a sweet, lovely daughter, instead of the schlumpy son she endured for many years. Mother and daughter took to each other as they never had as mother and son.
Judy even encouraged Mom to "girly herself up" a bit too. She let Mom borrow some of her pretty lingerie and darned if Mom didn't look good in it. Surprising that a woman would make the effort to look girly, isn't it? But Judy was a good influence on Mom too.
The next day, a Saturday, Judy worked her first shift in "sleep"wear (as if there were much "sleeping" going on when that lovely stuff was teasing some poor man's libido).
Her supervisor was the lovely Mary, who told Judy that she was sure that her department's revenues would go up with Judy working there.
And how true. The men were drawn to our little heroine like oversexed flies and the babydolls were flying off the shelves. Judy was doing straight sales, teasing the customers, but not pleasing any Gold or Platinum Card holders
At around 11:30, Mr. Hung arrived. Judy watched him shift overpriced item after out-and-out ripoff into his shopping cart, then wheel it to a checkout station.
Judy mentioned to Mary two very different observations about Mr. Hung from the last time she had seen him. "He's smiling, Mary. And he's very pale."
Mary whispered to Judy, "When he makes those purchases, he goes into Platinum Club status. He's dreamed of that for years."
That made sense to Judy. "But why is he pale?"
Mary said, "The rumor is he's been selling everything he owns to go Platinum. Including spending a LOT of time down at the local blood bank."
There was a man who really loved pantyboys.
Mary rang up Mr. Hung's purchases, then presented him with his Platinum Card. The man was crying. Bawling. And his pants were severely tented. Judy wondered where he had found enough blood left in his body to produce such a stiffie.
Judy felt as if she were part of the store's history. Especially when Mr. Hung said, "I would like Judy to 'test drive' my purchases, please."
As always, what a salesgirl at Stiffman's did with a customer or refused a customer was her call.
Judy's panties bulged as she gave Mr. Hung a kiss, grabbed his arm and escorted him to Dressing Room Two.
Her first test drive for a new Platinum Club customer. Judy was very proud, but she hoped that poor Mr. Hung didn't overexert himself.
Mr. Hung's aspirations for his first test drive proved to be quite modest. He handed Judy a perfect, tiny, pink babydoll; pink, fully-fashioned stockings; the world's frilliest, pink garter belt; and pink, strappy, sandal mules with five-inch stiletto mules [panties were conspicuous by their absence] and asked her to put them on for him.
Judy was blushing a little about getting naked in front of a man she hardly knew. But then she thought, "I'm a pantyboy. I show men my goodies and then invite them to enjoy me."
Even then, Judy understood the Pantyboy Code.
Mr. Hung watched the disrobing with great interest and removed his shoes, socks and trousers concurrently.
Since I've known her, Judy has been the biggest pantyboy teaser in the world. So I'm sure she gave Mr. Hung a great show that day. When she got her outfit on, she twirled this way and that, showing Mr. Hung what financial ruin brings a man if he plays his cards right. She was stiff and drippy and the babydoll was so short that Mr. Hung could see her pink goodies. Her pretty bottom was exposed to the lustful man's attention as well. Remembering her training, Judy saw where she was standing in relation to the button she would push to call the paramedics if needed.
Mr. Hung held out his arm and beckoned her to sit on his bare lap. He had a very nice cock and he was an attractive man in his late 40s. Like many Asian men, he was not overly hirsute, so few hairs tickled Judy's soft bottom.
Mr. Hung shuddered with pleasure when he felt Judy's bottom cover his thigh. He had waited for this so long. Judy wanted to make the poor man's first test drive one to remember. So she threw her arms around him and gave him a sweet kiss. With lots of tongue. Mmmmmm. He liked that.
Unfortunately, he liked it too much.
Mr. Hung groaned, shuddered and covered Judy with a quart of hot cum. He must have spurted seven thick ropes of creamy goo. Thinking quickly, Judy put he warm hand on his shaft and pumped him sweetly during thee last four globs.
The poor man was so embarrassed.
Judy was very consoling. Asked if she could "be with him" the next time he came in" and all that stuff women say to guys who drop their cargo before they get to port.
She even rubbed his balls very nicely and asked if he wanted her to "kiss his red knob" for a while.
The man was very grateful, but said, "Thanks, but I need to rest a minute."
Moments later, Mr. Hung was on the bed, on his back, snoring peacefully.
Judy was a little miffed that she was all dressed up and didn't even spurt her own cream, but it was all in a day's work.
Keeping her voice down, she telephoned Mary from the room to report on developments.
"What are you wearing, Sweetheart?" Mary asked Judy.
Judy told her.
"I'm on my lunch break," Mary said. "Dressing Room One is open."
Judy got the hint. And she got two lovely ball-drainings (and gave two in return) from her supervisor.
Labor-management relations do not have to be contentious, people.
Chapter Eight – Ob-la-di, Ob-la-da, Judy's Life Goes On
Judy settled in very nicely to life at Stiffman's. She's told me many wonderful stories about her adventures as a successful salesgirl.
She was especially proud of the way her Mom perked up and became the sexy, attractive woman she could be. A woman with men circling her. Asking her out. Making love to her. I'm getting ahead of the story, but Mrs. Strokewood met and married a very hunky and nice man who fully appreciated a woman who wore make-up, perfume, fully-fashioned stockings and big heels.
Sissies are a good influence on women. They raise the bar.
Judy met a few nice men too. The same kind of men her Mom met. The kind who adored her femininity.
The store seemed busier than ever and one night when Mr. Stiffman was giving Judy's perfect bottom a good porking, he told her that he was convinced that she was a big part of the reason for making him even richer.
Stiffman and Judy got together every three weeks or so for all-night counseling. It would have been more frequent, but Stiffman couldn't disappoint the other employees.
Judy continued to excel in customer relations. Mr. Hung was worth a snicker from all the salesgirls because he was known as the fastest gun in the West. He would get himself naked and settled for a lovely test drive with Alice or Emily or Helen, the girl would sissy up in her new frillies, sit on his lap, touch his Johnson, then suppress a giggle as he lost his load. Then he would stagger over to the bed and fall dead asleep.
Mr. Hung needed a blood transfusion almost as much as he needed pantyboys.
I won't bore you by telling you about all of her experiences with customers, but let's just say that they weren't all as passive as Mr. Hung.
There was Mr. Buffley, for example. That Platinum Card holder bought only very high, strappy, stiletto mules, and asked his "test drive" pantyboys to wear only the shoes.
Judy was a bit apprehensive about that, since she wasn't totally confident as a "girl" and thought she needed girlish stockings and lingerie to excite a man. Mr. Buffley seemed to think that a lovely, naked pantyboy, augmented only by her make-up, earrings, nail polish, sexy shoes and delicious, budding femininity, was all he needed.
I've seen Judy like that, Honey, and it certainly took the wrinkles out of my popsy.
It revved up Mr. Buffley too.
Judy told me that the first time she stood almost naked (except for her pink heels) in front of Mr. Buffley, she was blushing all over her scrumptious body. Her usually pink knob was almost purple with all the hot blood that had engorged her tiny pricklet. Being naked was so DIRTY. And it made her feel so submissive. A magnificent combination,
The "bad" man called her over and sat her on his naked lap, asking her questions as he tickled her poppet and her "pink purse."
"Are you a good girl?"
"Do you like older men?"
"Does it feel good when I rub you like this?"
"You're so lovely. Your nipples are so beautiful. May I kiss them as I fondle your girlish 'pink parts'?"
<Spurt> "Oh!!!" <Spurt> "Mr…. <Spurt> "Agghhh" <Spurt> "Buffley" <Spurt> <Whimper> <Spurt>
There was also Platinum Card holder Mr. Dickson, who brought his 18-year-old son Rodney along for a test drive with Judy.
A bit weird, huh?
Yeah, but not as weird as you might think. Mr. Dickson bought a LOT of frillies that day, settled in to watch Judy strip and put her first outfit on, then left Rod alone with Judy.
Judy was a bit apprehensive for three reasons. One, she had never been with a man that young. Two, she was apprehensive about someone that young not knowing how to treat a delicate flower such as herself. And three, she KNEW Rod, from high school. "Harold" (remember him?) and Rod had been in some of the same classes in high school. Did he recognize her?
Apparently not. All Judy saw in Rod's eyes was lust. No recognition. Lots of lust.
No wonder. Judy no longer looked like Harold. She no longer was Harold.
Still, it was fun to watch someone from Judy's previous life aching to fuck her.
Judy was wearing a lavender bustier with garter straps that connected to naughty, tan, seamed stockings. Her matching lavender panties were stretched with her girlish excitement as she sissied back and forth in her lavender, stiletto pumps, modeling herself for her "Platinum Prince."
Steam was coming out of the young man's ears as he asked Judy if he could see her pricklet, thus satisfying his curiosity about whether someone that feminine could have a little "piece of pork."
The poor young man was probably sincere when he asked "just to see it."
Of course, when the little doll giggled and "reluctantly" peeled her panties, Rod reevaluated his priorities.
"Its..I mean, you're so beautiful," the stupefied lad said. "I never thought….."
A man's first sissy can imprint on his consciousness in ways he never imagined.
Judy was enjoying Rod's adoration…and his discomfort. She remembered how Nancy wisely predicted things would go with a man new to sissies: He would begin with, "Can I see it?" followed by "Can I touch it?" and climaxing with "Can I suck it?" A man's curiosity about a sissy's popsy will not be easily deflected.
So far so good.
Judy moved more closely to Rod. He was a nice-looking young man. And very grateful to be with a sweet baby like Judy.
"Do you like me, Rod?" the little teaser asked.
"You can touch me if you want, Rod. I'm just a helpless girl and I couldn't stop you from doing ANYTHING!"
Despite his father's wise counsel about the endless delights of making love to sissies, Rod was wrestling with the notion that consuming the feminine darling inches in front of him would somehow be "gay." Then he got smart.
Rod laid his hand on Judy's teeny prick. He almost fainted when she gasped with pleasure. He rubbed it a bit, then gasped when creamy, sticky stuff oozed from her peehole.
Judy was sexually aroused, but otherwise calm. Rod was becoming frantic with desire for the submissive sweetie before him.
Rod was surprised when he took Judy's pricklet in his mouth. Judy expected it. But she liked it very much. The young man didn't know much about cocksucking, other than what he had learned from observing Ashley Hoover, his former girlfriend. He was already proud of the fact that, if squeals and whimpers mean anything, he was more accomplished than Miss Hoover.
Judy loved the fact that she was Rod's first "special girl." She liked his youth. And she especially loved a job where she got a six-figure salary (plus tips) for wearing lovely clothes and getting her penis sucked.
Judy was shuddering and cumming in very short order. Young Rod Dickson seemed quite proud of himself for swallowing a full pint of sissy cream. Judy, ever the polite one, returned the favor, then sucked her new friend to a new stand.
Judy got on her back, lifted her legs and told Rod where the lube was and where it went. And what she hoped would follow his lubed fingers in her pussy.
That dream came true. And then, because Rod was 18, her dream came true again. And again.
It was a good thing most of the Platinum Card customers were in their 40s or older. If they were all Rod's age, the salesgirls would never be on the floor making sales.
The older men gave the girls nicer gifts – pretty things like bearer bonds and fully paid condos. But the young guys could certainly "bring it" in the multiple-cum department.
Judy decided that she could enjoy either younger or older men. But a two-carat diamond was a nice tiebreaker.
You're probably wondering whether Judy dated when she was working at Stiffman's? Does Rush Limbaugh mock liberals?
Judy was a very popular young lady, though she limited herself to three or four date nights a week. She wanted to spend an evening or two with her Mom, though Mom had gotten so popular with men, they had to coordinate their schedules carefully. A night or two each week, she would "date" one of the girls from work. Like many sissy relationships, Judy would be in a white-hot love affair with Cindy in "shoes," for a week or two, then pick up with Petra in "panties."
Judy didn't just date customers. She loved to test the theory that she could have just about any man she wanted. So she seduced a high-school English teacher whom she had admired, the owner of a jewelry store (who contributed significantly to Judy's ability to accessorize), then a man at motor vehicles, who gave her a license to drive anything with wheels even though Judy had no clue as to how to even turn an ignition key.
Like the other girls at Stiffman's, Judy was pelted with marriage proposals from all sorts of men. Rich men and poor men. Beggar men. Thieves. Doctors. Lawyers. Even an Indian chief.
The men, being men, all wanted to "possess" the pantyboys. The pantyboys, being pantyboys, all wanted to be possessed. But by the right man. And on the pantyboy's schedule, not the man's.
In the year that Judy was at Stiffman's, there were 20 weddings. Stiffman took to closing the store at three on Saturday afternoons because almost half the time, there was a wedding to which all the staff were invited. Seeing an opportunity, Stiffman opened a bridal department, knowing that an eager groom would be more than willing to buy his sweetie the $6,000 gown that Daddy couldn't afford. A lovely side effect for Stiffman was that a lot of Gold and Platinum Card holders bought gowns for test-drives with their favorite sales professionals.
Stiffman just couldn't lose.
And, of course, every bride wanted her bridesmaids, who were almost always fellow pantyboys. Judy had been in five weddings already when Nancy asked her to be her maid of honor.
Nancy. The fairest of them all and the head of the sales staff, she had finally, at age 24, accepted the proposal of a suitor. Jeremy Bumworthy was a self-made, 35-year-old, multi-millionaire who would have gladly signed a pre-nup giving Nancy 99% of his assets. Nancy insisted that she only get 80%. She did, after all, love him.
Nancy's selection of Judy as her maid of honor suggested to the pantyboy community that she considered Judy to be Nancy's successor as the prettiest single pantyboy in a 1,000-mile radius.
Judy was thrilled and flattered. She loved weddings and wanted one of her own. But not until she was around Nancy's ripe old age. Judy was only 19, for goodness sakes.
Nancy was a lovely bride – angelic almost – and she seemed supremely happy. The most unusual aspect of the wedding proved to be the arrival of a guest who created a major stir among the pantyboys – and among the many admirers in attendance.
In the rear of the church after the ceremony, Judy heard the other bridesmaids buzzing about a handsome middle-aged man who took his seat just before the ceremony began. Accompanied by two exquisite young women (?) in summer Chanel suits, the man was Nick Nickerson, world-renowned publisher of Panty Boy magazine.
Rumors were flying: Nick was looking for his next cover girl. He was in love with Nancy and was upset that she was marrying. He was there to see his old friend Mr. Stiffman. He was thinking of marrying a pantyboy and wanted to see what a pantyboy wedding was like. He was looking for a pantyboy wife among the Stiffman's staff.
The truth was that Nick just loved all things pantyboy and, having heard of Stiffman's Intimate Apparel, asked Stiffman if he could visit. Rather than travel alone, Nick brought along two creampuffs from his stable – Lisa and Janet.
Judy was somewhat attracted to Janet, a delicious little doll who was only five-foot-four, but stood five-nine in her heels. Judy was thinking about how sweet it would be to see Janet on her back with her pricklet stiff and dripping and then…..Nick spoke to her.
The other girls were boiling with envy as Nick went directly to Judy and said, "I couldn't take my eyes off you, Maid of Honor. You're an exceptional beauty."
Judy gulped. Well. That said it all. No guile there. Judy had never been so flattered in her life. That was like Pavarotti calling you a great soprano. She was blushing crimson when she thanked him. Then she went off to join in the orgy of photography that marks a wedding.
At the reception, Nick pressed his attentions on Judy again. Judy enjoyed the envious stares of her sisters. Nick was cute and if he was half the lover his reputation claimed he was……
Well, of course they fucked. Lots. In fact the whole weekend. And on Monday, Judy asked Stiffman for two weeks vacation so she could accompany Nick to Fromage. She was going to be in a "pictorial" in Panty Boy, then hang around the Panty Mansion for a while.
Stiffman granted Judy's request, of course, but with some sadness. He knew she would never return to her job. She was going to be a Panty Boy star.
Well she should be; and well she has been.
If you've been following along, you know that, Judy, Amy, Sandy and I have since helped millions of men spill barrels of cum, then moved in together to a huge apartment in the best part of New York.
The next story, "Sissy Stepmother," will tell you all about Sandy. Then you'll get to FINALLY hear all about me, Cheryl, in "Slacker Moms." The fifth and last story, "Sissies and the City," will be about our lives together.
It'll be a very "draining" experience, I guarantee it.
Please let me know what you think email@example.com
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