Panty Fiesta

by Gingerfred Man

 

Chapter One – Panty Mistress

 

Rhonda Cummings was the headmistress of the Cummings Feminization Academy and she loved her work.

Mothers who wanted their reckless, wimpy, or otherwise difficult sons feminized relied on Rhonda. They found Rhonda's services to be wildly expensive, but her results were spectacular.

Little wonder, since she learned how to feminize young men by sissifying her own sons.

Rhonda had married Bruno Cummings when she was 18 and he was 27. Rhonda was (and is) a spectacularly beautiful woman. Tall and full-bodied, with 42-DD breasts and a wasp-waist, she is the Barbie doll come to life.

She was attracted to Bruno because he was the most masculine person she had ever met. Bruno was a successful, professional athlete who earned millions each year and adored his young, Playmate-quality wife so much that he never fucked more than one sports groupie on each road trip.

Bruno was hairy and muscular and always had a bristly, five-o'clock shadow. He fucked Rhonda at least five times every day they were together. He dominated their lovemaking, making Rhonda a willing, orgasmic slave to his brutish, though loving sexual mastery. Rhonda's days were a blur of multiple orgasms and she was very, very happy.

When Wilbur was born, in their third year of marriage, Bruno and Rhonda continued their sexual athleticism. In fact, Rhonda learned the pleasures of a ten-inch cock in the bottom during the post-natal period when vaginal sex was forbidden them. Her orgasms seemed to be even more intense whenever Bruno ravaged her lovely ass.

Nor were they deterred from their ongoing nuptial orgy when Orville was born during their fifth year of marriage, though tragedy struck soon after.

 

When Orville was four months old, true to Bruno's macho persona, Rhonda's husband's throat was slashed during a road-trip barroom brawl and, sadly, Rhonda was widowed.

Rhonda's heart was broken and for some time, there was a question whether she could continue. There were her boys to consider, however, and the proper spending of the $35 million Bruno had left her.

For the first time, Rhonda began to take motherhood seriously, giving her full, personal attention to her boys. Two-and-a-half-year-old Wilbur and six-month-old Orville were the right brothers to get her out of her depression. Unfortunately for the lads, they had the wrong mother for who they were.

Rhonda began to notice early on that neither boy was a true heir to her Bruno. They cried and whined. They never beat up weaker kids or took their lunch money. Both entered puberty as virgins. And they were hopeless at sports. Rhonda was terribly disappointed with them and saw only one option. When Wilbur was 14, Orville 12, and Rhonda a spectacular 35, she decided to feminize them.

Rhonda consulted the finest mentors at the American Sissification Institute and went about things properly.

She had long ago broken her boys' will to resist her, so she was easily able to change their names – Wilbur to Linda and Orville to Denise – and introduce them to their feminine sides. Since Rhonda was new to the feminization process, things proceeded slowly. But the boys accepted their lot. Somewhat eagerly, in fact.

Rhonda knew she was doing the right things when she saw the little pantywaists' cocks erect every time they put on panties or stockings. The sissies learned to walk in heels very quickly and before long they were mincing around the Cummings mansion acting like proper little panty boys.

Of course the feminization would only be complete when they became proper receptacles for men's loving juices.

The American Sissification Institute was firm on the requirement that sissies needed regular milkings by a man to ensure proper feminization.

Over the years, Rhonda had found comfort with several of Bruno's teammates, one of whom always seemed to be at her home for an overnight visit to ensure that Rhonda was getting along well. Rhonda's conjugal visitors were always eager to assist in the development of her sissy sons. So every morning, Linda and Denise would be milked to a monster cum by the uncle du jour. Often another uncle would stop by at noon, sometimes as a training aid for Rhonda's instruction to her sissy sons on cocksucking. Mother would demonstrate, then Linda would drain the brave volunteer's cock as Denise sucked the man's balls. Then the sissies would change places and suck the man to another ballbuster cum.

It was amazing how excited the men were about sexual activity with her sons. They were macho, intensely heterosexual men, yet, the panty boys seemed to excite them more then Rhonda did.

In the evenings, the boys' instruction would usually involve lying on a bed in a tiny nightie, taking an uncle's big rammer into their warm, tight places while screaming and cumming helplessly throughout the night.

The boys had no complaints and neither did the men.

When Linda turned 18, Rhonda married him off to a 40-year-old Texas oil baron. She and Denise cried at the wedding, though the biggest tears were shed by the uncles. Denise continued to take very good care of the uncles' needs (and his own) until he was 18 and Rhonda married him off to Butch Ferguson, Bruno's teammate, an enthusiastic uncle, hundred-millionaire, and owner of the biggest, thickest cock Rhonda had ever taken into her tight bottomhole. He made Denise very happy.

Both her boys were very happy, thank you, and she was glad she had helped them become who they really were. Rhonda's talent for sissification was obvious. It was a gift she needed to share with the world. So she applied for a charter with the American Sissification Institute and opened her Cummings Feminization Academy.

Four years later, as Rhonda turned a still-mega-babish 45, Cummings was the finest institution of its kind in America. She had a staff of six women and 20 men, with 45-60 sissies usually in residence.

Their mothers paid richly for Rhonda's services.

The sissies were always in different stages of their feminization, which made organization a constant challenge. Some of the pantywaists were eager to slip into heels and stockings and become a man's docile bedwarmer. Others fought back. Those were the ones Rhonda liked best

Rhonda wasn't big on physical punishment. Humiliation was a much stronger means to keep her sissies in line. As was praise for the little pussyboys' developing beauty and femininity. But she did enjoy an occasional over-the-knee session with a recalcitrant sissy who had not yet surrendered to his feminine feelings. The hard cases were the ones with the stiffest erections from wearing panties and the ones who ended up cumming whenever a man looked at them.

Rhonda enjoyed the first Saturday morning of each month best. It was the day she would choose the sissies from among her flock who would be "exported" for the weekend.

The "exports" were little pansies in the most delicious stage of their feminization. They were beginning to surrender to their femininity, cumming in their panties frequently, but still holding on to some of their masculinity. They were the sissies who were most susceptible to the tastiest humiliations, which was what "exporting" was all about. It was also a way to supplement Rhonda's already-huge income with the fees her clients paid for the weekend use of a sissy.

Few sissies returning from an "exported" weekend ever gave Rhonda much further difficulty.

It is one such weekend, and the sissies who experienced it, that this story is about.

 

Chapter Two – Full Panties

 

That weekend, Rhonda had a full slate of clients eager to initiate her panty boys into the secret worlds of their fetishistic desires.

Rhonda shuddered with anticipation as she thought of her clients and the sissies who would amuse them. Her clients expected lots of hard bulges and drenched panties and she knew that her pussy boys would not fail her or Cummings Academy.

Rhonda was especially eager to match up young sissy Susan with Rhonda's longtime friend and fellow filthy-rich woman, Estelle Brinkman.

Estelle adored her monthly session with a Cummings Academy confection, but Rhonda knew that Estelle would be especially pleased with Susan.

Susan was brought to Cummings Academy nearly four months ago in a sad, brutish state. His mother was at wit's end with him because of his unruliness, inflated ego and, worst of all, disrespect for women.

Yes, it was true that by some standards, Susan (Rhonda couldn't remember what his awful boy name had been) had been doing well as a boy. He was quarterback and captain of his football team, girls adored him and there were his…ahem….physical attributes.

Susan would probably have still been a boy had he not abused his gifts. Refusing to use "protection," the vile male had impregnated the youngest daughters of two of his town's finest families. Running wild, he had been arrested for two DUIs, the second time with no license to revoke. He was headed for Juvenile Detention, with the full concurrence of his mother, until the moment when, in a drunken state, he slapped and cursed his mother for rebuking him and his evil ways.

Susan's mother decided that Juvenile Detention would only make her son a viler example of the male species. His demonstrated lack of respect for women had to be dealt with immediately. And the best way to do that, Susan's mother decided, was to feminize him.

A wise woman, Rhonda reflected. Frillies and a diet of male cum direct from its source was what a specimen like Susan required. And Cummings Academy was the place where he would learn to crave both.

Rhonda remembered fondly how Susan had been a hellish spitfire for his first month at her Academy. Oh the spankings he received from the on-staff uncles who loved their work. The many, punitive nights Susan slept with the big dildo, greased and slipped up his bottom, then secured and locked into place. Of course Rhonda was confident that Susan would become more feminine and docile. The first evidence was his cum-filled panties the mornings he awoke from a "big-dildo-punishment" night. Then his cum began to spurt whenever he wore something particularly attractive or he examined his new beauty after being shown a new make-up or hair technique. Like the rest of Rhonda's sweet creampuffs, Susan fell in love with himself and his own femininity.

And like the rest of the sissies to be exported that weekend, Susan had not known intimacy with a man. After export weekend, such intimacy would be rampant for the girls and her male staff. It was why she was able to hire the finest, hunkiest male staff at incredibly low wages. Rhonda enforced the no-men-before-export rule ruthlessly, but she was sure that several of the little angels were sucking each other's pretty little knobs and swallowing hot loads of sticky cream. Sissies will be sissies after all.

The male staff was commonly used to spank and milk the "pre-export" sissies. Even the cruelest mistress would not deny a sissy the minimum thrice-daily milkings by a man that his little peener and walnuts ached for.

Yes, Susan was coming along nicely and Rhonda couldn't wait to show him off to Estelle.

Estelle arrived, as planned, at 10 a.m. that Saturday morning and the two rich ladies exchanged air kisses.

Estelle was a slim, stunningly attractive woman of 45 years and a bosom of 44 inches. Her Chanel suit dampened her voluptuousness barely a hair and her long legs, encased in silky stockings capped by five-inch stiletto pumps cried out for sex.

"I'm hoping for something special this month, Rhonda," Estelle said.

Rhonda nodded and rang a bell. The door to Rhonda's office opened and there stood Susan.

Susan tottered in on his four-inch-stiletto, red mule sandals.

A thin layer of perspiration formed on Estelle's upper lip.

Susan was the proud possessor of a thick, ten-inch cock and it was erect and exposed to view.

Susan was already humiliated. It was bad enough that he had to expose himself to the people at this nuthouse, he thought, but who was this? She was older, but very dishy. Like that crackpot Mrs. Cummings.

Maybe his luck was changing.

Rhonda had specified Susan's attire. He was wearing full, evening make-up, with dramatic attention to his eyes; a filmy, black, mid-stomach-length negligee; silky, black, seamed stockings hooked to a satiny garter belt; and his red heels.

Before appearing in Mrs. Cummings' office, as happened far too often for him since coming to Cummings Academy, Susan had admired himself in a full-length mirror and could not help but spurt his thick cream. He didn't want to do it. He was just so darned pretty. Staff matron Mrs. Johnson, who was supervising Susan's preparations, had caught most of the mess in a Kleenex she had ready for such an eventuality. Around Susan, a full box of Kleenex was a necessity.

The second orgasm took them both by surprise and some drops even splashed Mrs. Johnson. Susan was worried that she would punish him but she only laughed at what a silly little sissy Susan was.

Neither orgasm had taken anything from Susan's erection. Ever since he had been at Cummings Academy, Susan was either cumming, or "on the verge." Even though he had cum twice in gut-wrenching fashion, Susan was erect and throbbing when he entered Mrs. Cummings' office and saw the strange lady.

The strange lady was looking at him as if he were the dolly she always wanted for Christmas. And that worried him.

Estelle looked at Susan, then at Rhonda. Then she asked, "Is he always…….?"

Rhonda smiled and nodded.

Estelle sighed, then regained all of her imperiousness.

"Thank you, Mrs. Cummings," she said. "Have him spanked and delivered to my home within the hour." Then she clacked directly out of the room.

I believe that was a bullseye, Rhonda thought.

Spanked? Susan thought. But I didn't do anything. Of course protesting got you double, so he kept silent. But why was he being "delivered' to that woman's house?

Rhonda looked at Susan with something he rarely saw from her – approval. The spanking was unjust, but he accepted it. He was growing up. Rhonda also did something she almost never did with her sissies. She explained her actions.

"Mrs. Brinkman wants you spanked so that you will be sweet and docile in her care this weekend. And the customer is always right."

It was little comfort to Susan's bottom, but he felt Rhonda's approval and he liked it.

Rhonda pushed another button and staff member "Uncle" Ralph appeared.

"Ralph, give Susan a good spanking, then milk him if he needs it. You need to get him to Mrs. Brinkman's by 11:05. If you have time, he can milk you too. Kiss him if you want, but don't mess his make-up so badly that he can't repair it."

Whooooaaaaaaaaaaa! Susan thought. That was new. He had grudgingly let those middle-aged thyroid cases spank and milk him, but kissing them? And milking them?

Susan didn't have time for much reflection, since Ralph was a man on the clock. It was a 15-minute drive to Mrs. Brinkman's. Getting the car, repairing make-up, another 15. If Ralph wanted to be the first uncle to kiss Susan and cum all over his sissy hand, he had better get spanking.

Susan was pissed about all this. Ralph helped him out of his nightie so it wouldn't get messed up, then removed all of his own clothes! He was going to spank Susan while he was naked!

Oh my goodness, Susan's big rammer was very excited. It was red and sore and throbbing as Ralph placed the sissy over his naked knees. Susan didn't want to look, but Ralph's stiff, big thing was rubbing against the left side of Susan's torso. It was disgusting. So much so that after two solid, cheek-warmer smacks, Susan shivered and came all over Ralph's thighs. Oh, that was humiliating!

Ralph kept spanking Susan until he had given ten firm strokes on each cheek and Susan was on the verge of another emission. They had 20 minutes of free time left.

Ralph helped Susan up and sat him on his naked lap. Oh, Susan thought, his thighs are so warm on my poor spanked bottom. Susan felt Ralph's thigh hairs rub against Susan's testicles, tickling them mercilessly.

Ralph took Susan into his arms and cuddled him, apologizing for the unjust spanking.

Susan didn't want to admit it to himself, but that felt awfully good. No one had hugged him since he had arrived at Cummings Academy.

Then Ralph kissed Susan.

Agggghhhh!

Susan's mind said, "Struggle! Fight back"

But Susan's body tingled and Susan's balls emptied all over both of them.

They kissed for several minutes until time grew short. Then Ralph placed Susan's hand on Ralph's stiff cock. Susan obediently stroked it to a gooey conclusion, kissing Ralph sweetly the whole time.

Oh no, Susan thought. What have I done? Susan prayed that Ralph would never tell anyone.

Ralph smiled at Susan, then kissed him.

Then Ralph was all business, dressing himself and getting Susan repaired for a weekend with Mrs. Brinkman.

Susan's ears burned hot with shame. Next thing you knew he would be sucking cocks, he said to himself. Then his resolve stiffened. And so did his cock.

Ralph drove rapidly to the Brinkman mansion and only said to Susan, "That was nice. We'll have to do more again soon."

Susan groaned inwardly. He couldn't do stuff like that with any man. Ever.

Or so he thought.

Ralph rang the bell at precisely at 11:05 and they were greeted by an English butler named Soames, who showed no surprise at the sight of a half-naked sissy with a 10-inch erection.

Ralph said goodbye and Susan considered begging him to take them away from all this. Instead, he sissied and minced behind the butler, up the grand staircase, to the master bedroom, where the mistress awaited.

Soames opened the door and there stood Estelle Brinkman, dressed exactly as Susan was – full, evening make-up, with dramatic attention to her eyes; a filmy, black, mid-stomach-length negligee; silky, black, seamed stockings hooked to a satiny garter belt; and four-inch-stiletto, red mule sandals.

Her pussy was dripping wet as she said, "That will be all, Soames." Soames closed the bedroom door.

Maybe the day wouldn't be a total loss, Susan thought. This lady was older, but her pussy was definitely more to Susan's liking than "doing it" with a man.

If Susan had any notions about being "the man" in what was about to happen, they were quickly dispelled.

"Kiss me, you little sissy faggot," Estelle demanded.

That was bossy and insulting. But a) the Cummings Academy sissies had to do as they were told or suffer and b) pussy is, after all, pussy.

So Susan kissed Estelle. Then Estelle took over.

Estelle pushed the sissy onto her bed, on his back, then leaped on top of him. After 30 seconds of foreplay, she grabbed his cock, gasping at its size and heat, then sat on it.

On top, Estelle ground her pussy up and down on Susan's big cock. Susan didn't feel very much like a big stud. He was being fucked, not fucking. The woman was squeezing his cock with her muscular pussy, kissing now and then, but mostly just enjoying the feel of a cock in her pussy as she felt lipgloss on lipgloss, lingerie on lingerie and stocking on stocking.

Not surprisingly, Estelle came first, followed closely by Susan, then Estelle, then Susan and yadda, yadda, yadda.

Two hours later, they both sank back, totally exhausted.

Estelle seemed to have had a much better time than Susan had. Susan just felt……used. He wanted some affection with his sex. Geez, even Ralph had given him more affection and shown him a better time.

What was Susan saying? Ralph was a guy! Ick.

Still, Estelle was not a lover. She was a self-satisfier.

And Susan didn't like it.

Susan fell asleep and so did Estelle. At 4 p.m. Estelle woke him up. Did she want more?

"I'm taking a break," she told Susan.

Whew, he thought.

Not so fast.

Estelle touched and intercom button. "Soames," she said.

Seconds later, Soames appeared. He didn't seem disturbed that he had been summoned by his naked, cum-drenched mistress and her equally naked sissy lover.

"Clean him up and have him back to me at 8 p.m.," Estelle said. "Do as you wish until then."

That got Susan's attention. The "do as you wish" part.

Soames was a man and he was going to do as he wished? Men wish a lot. Susan knew from his own experience.

Soames was about 50, not bad looking and in good shape. But he was a man. And an English butler. So servile. And stuffy.

Soames held the door open and Susan got out of bed. Estelle didn't even seem interested in a see-ya-later kiss. What a loser!

Apprehensively, but obediently, Susan followed Soames.

Soames said nothing as he led Susan to the third floor and to his bedroom.

He opened the door for Susan and the naked little creampuff entered the unknown.

It was a normal, masculine room, with a private bath. Nice, actually.

Soames smiled. Then he even spoke. He went into the bathroom, turned on the shower and invited Susan to clean himself off. Susan accepted.

The hot water felt wonderful after that strange sexual marathon. He closed his eyes and let the warm water hit his face. For the first time in Susan's recent memory, he didn't have an erection.

That changed very quickly. The shower door opened, then closed. Susan felt a naked body embrace him from the rear. Soames! Warm, gentle hands rubbed soap on his back. Then his shoulders. Susan trembled. This man was so much nicer to him than that awful woman. And the other awful women at Cummings Academy. Ralph had been nice to Susan too. Hmmm.

Soames hadn't done anything overtly sexual, but Susan was hard once again. He gasped as Soames moved closer and rubbed what felt like a substantial cock into the separation between Susan's bottom cheeks. Ohhhhhhh.

For a panty boy who hadn't felt affection in a long time, Soames was getting to Susan's very center.

Soames touched Susan's pretty cock, rubbing soap along its considerable length and girth. Susan whimpered most unmanfully.

This was more like it, Susan thought. Then he thought something like, "Too bad it had to be with a man," but that thought seemed to dissipate as Soames' gentle, loving touch brought Susan to orgasm's brink, then pushed him over. Unnnhhhhhh. Susan spurted thick globs of sticky, sissy cream. Soames rubbed his cock against Susan's smooth back and kissed his neck as Susan ejaculated.

Ohhhh!

Maybe men weren't bad as sex partners after all.

But there was much more research to be done.

Susan turned toward Soames and looked at him through the warm stream of water. He was a fine-looking, older man. Muscular. Hairy. And a very nice tongue that had found its way halfway down Susan's throat. Susan was panting as he felt Soames' cock rubbing against his own. Then he purred (actually purred) as Soames' loving hands explored Susan's pink bottom. Soames ran his fingers along the smooth, plump cheeks, enhanced as they were by the Cummings Academy "vitamin" shots resident sissies received every day. He cupped Susan's globes and lifted him gently to a height where Soames could kiss Susan's developing, puffy nipples. Then Soames entered Susan's bottom with a long finger as he licked Susan's wet left nipple.

Susan was only human. He squealed like someone's little sister, then began to pump out his cum in hot globs.

Trembling. Hungry. But most of all, surprised, Susan surrendered to his body and spirit to Soames.

Susan's new best friend hadn't even cum yet, so Susan decided to change that in a way that Susan never thought would happen. The sissy doll got on his knees in the shower and took Soames' velvet knob into his wet mouth. Soames groaned and murmured soft endearments as the shower poured warm water onto the loving couple and Susan worked toward the big, girl's reward.

The pretty sissy sucked and licked Soames with enthusiasm – and with some skill for a first timer.

It was certainly good enough for Soames. He held Susan's head, told him he was beautiful, then rewarded the panty boy with his first mouthful of cum.

The hunky butler eagerly emptied his nuts, then pulled the little sweetheart to his pretty feet. They kissed long and hard, then turned off the shower and emerged. They dried each other off.

Soames produced a lovely, black, lacy, short nightie for Susan. The little flirt put it on, then dabbed on some lipgloss and blush. Susan kept looking at the naked Soames, whose weapon had recharged. Soames was smiling like the kid who discovered ice cream.

Susan, figuring in for a penny, in for a pound, teased and sissied his way to the bed. He lay on his tummy and pulled his nightie to his waist, exposing his rosy bottom. Then he wiggled his pretty bottom at Soames.

That was when Soames was absolutely sure that this was his lucky day.

Soames got on his knees at the foot of the bed and positioned Susan so that he could kiss and lick that girlish bottom to both their hearts' content.

Soames planted soft kisses on Susan's bottom, marking his territory. Susan groaned, not believing how good it was. When Susan was a boy, he just wanted to get his nuts off. Few preliminaries. Nothing after. This was better.

Soames gently separated the pink globes with his palms, then kissed the inner folds of Susan's lovely buttocks. Susan succumbed once again to a seminal discharge of large proportions.

Soames loved it. He began to kiss the little bullseye that he would soon explore with his big dart. The pretty sissy squealed girlishly. That dildo, once he had gotten used to it, had turned Susan on more than he would ever admit. Anal attention from a nice, thoughtful, hunky man, was EXCELLENT.

When Soames' tongue had Susan loose and ready, he kissed the little sweetheart's neck, then placed his considerable thruster in position.

Susan thought idly, "I'm a little sissy faggot now. This man is going to fill me with his seed and all I can do is hope he hurries. And fucks me hard. Then does it again.

All of Susan's wishes came true. Soames pushed and Susan's bottom, trained as it was by artificial penises, welcomed the real thing with relish.

Susan squealed and pounded a fist on the bed. Then he blew another four-star load of sticky cum into a set of already-messy sheets.

It was heavenly.

Susan felt the last wisps of his masculinity slide away. Then he relaxed and enjoyed being fucked. Very much.

Soames enjoyed it too. They both regretted when Susan had to be cleaned, made-up, outfitted in a prescribed peignoir set and returned to Estelle at 8 p.m. sharp.

Susan would have much rather stayed with Soames. He was a lover. Estelle was just a fucker. Like Susan had been, thousands of years ago, when he was a boy.

Dressed again exactly as Susan was, Estelle rode Susan's big girl for another two hours. Susan thought about other things. Like why were they dressed alike? Did Estelle want to fuck herself? And, were other men like Soames? He was pretty sure Ralph was. He hoped Ralph picked him up the next day to take him back to Cummings Academy.

Estelle's energy flagged at 10 and she gave Susan back to Soames for 12 hours.

Wow!

They had a wonderful time and Susan was half in love with Soames by 10 a.m. that Sunday morning. Or maybe he was just a sissy in love with men.

Anyway, the old weirdo only had two fucking hours left in her, so by noon, Susan was back in bed with Soames until Ralph picked him up at 4.

Soames kissed Susan goodbye in the room, but was all English butler again when they left it to join Ralph.

They said goodbye formally and Susan shed a tear on his pretty face.

But the world was full of men.

When he got in the car with Ralph. Susan asked, "Want to take the long way back to Cummings?"

Then the sissy unzipped Ralph and sucked his cock all the way back to the Academy. The 15-minute trip took one hour and 32 minutes.

And the men of the world gained a delicious new companion.

 

Chapter Three – Panties Down

 

Annie's export weekend filled the little sweetheart with dread.

Annie was the most well-behaved sissy at the Academy. He was obedient and sweet. And cute as a button. Sex with men terrified him, but so did most things.

Rhonda almost felt guilty about taking Annie on as a student. But for $120,000, plus expenses………

Annie was a good boy. Respectful and dutiful. But when his mother met Ricardo, all she wanted to do was tour the world and relieve Ricardo of his plentiful cum.

So Annie became superfluous.

Annie's mother loved the idea of sissifying her boy, then marrying him off to some rich man. He wouldn't bother her ever again. Better than a military school. They didn't promise you a marriage partner like Cummings did.

Rhonda had ten times as many suitors for her sissies as she did panty boys, of course. Not all the mothers wanted their sissies married off. And not all the sissies wanted to get married right away either. But attendance at one of the many weddings held in the Cummings Academy chapel usually stirred matrimonial feelings in the little creampuffs. They would quiver with envy to see one of their fellow panty boys arrayed in the splendor of a wedding dress. The sissy bride was the center of the universe that day, a feeling that all the little angels craved, and the prospect of a honeymoon with a dominant, broad-chested, thin-waisted, hairy, big-cocked man set sissy hearts aflutter.

Annie, of course hadn't reached that stage of his pouffish development. He was still thinking of the boyish life he had been torn from, which included his sweet girlfriend Katie. Oh, how he missed her, and their long walks and serious talks. Katie and Annie had never done "it," or even kissed, but Annie respected Katie too much to take her virginity before marriage. Now that was all taken away from him too.

Annie's immediate problem, however, was getting through his "export" weekend. There were rumors around the Academy that boys who were sent out for those weekends had to do awful things with men! Annie had also heard that some of the boys who had been at Cummings Academy longer than he had were doing sex things with the uncles! There were even supposed to be some icky things going on between boys.

If only he could go home.

Annie had to admit that he looked very pretty in the make-up, lingerie and frilly clothes the overbearing women who ruled that place gave him. He was ashamed, horribly ashamed of his erections whenever he slid on his stockings and panties. And the disgusting way he would cum and even squeal when those "uncle" people would stroke his little willie three or four times a day. If all the other boys weren't doing exactly the same thing, he would have been triply horrified.

Sometimes Annie and his roommate, Jenny, would cuddle in bed at night and tell each other their troubles. That was nice. Jenny smelled very good and he was warm and soft and understanding. Lately, Jenny had been doing things that were wrong – reaching under Annie's filmy nightie and tickling his peener and little balls until he made cum. Annie wanted to tell Jenny to stop, but it did feel very good. And Jenny was Annie's friend. And Annie was very submissive.

To be a good friend, Annie had been returning Jenny's "tickles," and even returning the kisses Jenny had started giving him recently. They started out as friendly kisses, but then the tongues got involved and they both got erections. The night before the "export weekend, Jenny had taken Annie's penis into his mouth and that scared Annie. It also made him cum until his balls almost fell off. Jenny was so sweet and so nice and so girlish and it all felt so good. Was it still wrong?

Annie was troubled by all that, but even more so by his awful weekend. Mrs. Cummings told him to wear a horrible pink, little-girl party dress that was so short, you could see his white, ruffled panties. He wore big-girl make-up, but for the first time since he had gotten to Cummings Academy, no stockings, garters and heels. He only wore little frilly white socks and pink-satin Mary Janes.

He had a bad feeling about all that.

Then he met the person who had given Mrs. Cummings a ton of money to purchase his time.

Mrs. Stack was a very pretty lady. She dressed like a grandma, but was no older than her late 40s. Her conservative, long, loose dress couldn't completely hide a voluptuous body.

Mrs. Stack met Annie in the reception area and gave him a huge hug. Then she told Mrs. Cummings, "He's adorable. Thank you so much."

Mrs. Cummings smiled at Mrs. Stack, then said, "Do as you're told, Annie."

It was said with a flat intonation, but it chilled Annie's spine.

Mrs. Stack took Annie to her SUV, kissed him on his rouged cheek and once again praised his beauty.

Annie was wary, but relaxed a tiny bit.

"Tell me all about yourself, Annie," Mrs. Stack said. And Annie did, all during their one-and-a-half-hour drive to the Stack's home.

Mrs. Stack was a good listener. Almost as good as Jenny, but without the "funny business" Jenny had initiated lately. By the time they arrived, Annie almost felt as if he had an ally.

When they went into the house through the kitchen door and Mrs. Stack gave Annie cookies and milk, Annie was feeling better than he had since coming to that awful sissification institute.

Too bad it didn't last.

When Annie had eaten his cookies and drunk his milk, Mrs. Stack said, "Let me introduce you to my husband. You're going to like him a lot."

Another ally, Annie thought, as Mrs. Stack led him upstairs to the bedrooms.

"Today's his birthday," Mrs. Stack said as she opened the bedroom door. "And you're his present."

Annie froze in the door. He saw a large, nicely appointed bedroom, with a sofa, thick carpeting and a king-sized bed with a naked man on it. Stroking his huge cock. And leering at Annie.

<Gulp>

What could Annie do? He did the only thing he could under the circumstances. He began to quiver and cry. Hot tears stung his pretty eyes as he thought that he was acting like the sissy he did not want to be. He was praying that he wouldn't pee his panties with fear.

"Walter, how do you like Annie," Mrs. Stack asked.

"The prettiest birthday sissy you ever got me, Sweetheart," her loving husband replied.

Mrs. Stack moved to the couch, got herself comfortable, and took up her knitting. "Annie, go over to the bed and give Mr. Stack a kiss."

He couldn't! But Mrs. Cummings' words were ringing in his head. "Do as you're told, Annie."

Slowly, Annie approached the naked man. He was about 50 years old, but in top shape. And rather handsome. His cock was a wonder. It must have been nine inches long and the head was a good two-and-a-half inches in diameter. And leaking nasty, sticky stuff. It was horrible!

As Annie reached the bed, Mr. Stack grabbed Annie's hand with the hand he had been touching himself with. Annie winced as he felt the sticky stuff on his hand.

Walter smiled. "It's all right, Sweetheart. I won't bite. We're going to have a wonderful weekend. You're going to suck my cock and swallow my cum. And I'll do the same for you. Later today, I'm going to put my cock in your bottom and make a real girl out of you."

Fresh tears stung Annie's face and he began to shake and whimper.

"I know, Sweetheart. You're afraid. I understand. But I don't care. We're going to do all those things and more whether you want to or not. Now take your pretty panties off, get up here with me and kiss me."

Annie was trembling so hard he was afraid he would fall over. He looked over at Mrs. Stack, who had been so nice, for a final reprieve.

Mrs. Stack was getting up! She was walking over to Annie! She was putting her arm around Annie.

"Sweetie," she said. "This is my husband's birthday and he's been looking forward to fucking you the whole year. We don't have a lot of money, so we've been saving for this. You aren't going to be selfish, are you?"

Hot tears stung Annie's face. He moved a little closer to Walter, who was smiling and holding out his arms in welcome. But he was naked and his huge cock was sticking up. And dripping!

Mrs. Stack tried reason yet again. She pulled Annie's panties down and held his tiny cock in her manicured hand. "Look at this little thing, Sweetie. It's pathetic. You could never make a woman happy with this. One might marry you, but she would cheat on you, take your money and run off with someone like Ricardo."

How did this woman know about Annie's mother's boyfriend – the reason he was in this predicament?

Mrs. Stack saw his puzzlement and said, "Honey, Mrs. Cummings told me and you told me in the car, remember? And please don't bring up your 'girlfriend' Katie to prove that you're better off as a man. Mrs. Cummings had a detective take these pictures to show you what your fate would be."

Mrs. Stack produced an envelope and opened it. Annie gasped as he looked at the shocking photos. His virginal Katie was in carnal embrace with Rod Pushem, a huge-cocked football player. In various shots, Katie had a mouthful, pussyful and assful of Rod's huge weapon.

Annie was shell-shocked.

Mrs. Stack hugged him again as she said, "I hated to do this to you, Annie, but it's for the best. As a man, women would treat you evilly. As a sissy, you will be the object of every man's dreams. Men will treat you with reverence and shower you with love and gifts. They'll use your body to satisfy their sick needs, but they'll make you cum and cum as they do it. Now let's start on your road to happiness."

Could she be right? She seemed so nice most of the time.

Numbly, Annie removed his panties and climbed onto the bed. He lay on his back, next to Walter, closed his eyes and tensed his body. Mrs. Stack resumed her seat on the couch and took up her knitting.

Annie was totally emasculated and humiliated. And that was only the beginning. But a calm peace began to come over him. Maybe this was his calling.

Those were Walter's hands gently pushing him over to undo the back of his party dress. Then taking it off, leaving Annie only in his undershirt, frilly socks and Mary Janes. He was achingly erect.

When Walter pushed Annie's undershirt up and began to gently lick and suck Annie's nipples, Annie gasped and came so hard he shot a stream of cum from his belly button to his chin.

Walter laughed. And Annie smiled a little. It certainly felt good. But when Walter's tongue lapped all the cum off of Annie, including from places where it never went, like his little pink bag, that was fantastic. When Walter sucked his little sissy wee, Annie blew cummies again, this time with a squeal as Walter sucked it all down.

He looked at Mrs. Stack, who had interrupted her knitting and was smiling with approval,

For some reason, Annie liked that.

It was clear to Annie that he had little choice but to return the cocksucking favor to Walter.

He trembled as he got on his knees on Walter's right side. His pretty bottom was pointing at Mrs. Stack, which he didn't notice, but she did.

Annie held Walter's cock in his hand. It was warm and throbbing. Walter moaned with pleasure.

Annie had never really given anyone pleasure before. Except for Jenny. He liked that part of it so far.

Walter's cock was still dripping with that sticky stuff. Annie decided to cross that hurdle last. He kissed the spot between Walter's balls and Walter groaned. Wow! What power! Annie had never had anything resembling power before.

Annie kissed the lower part of Walter's big fuckpole, giving it a couple of nice licks in the process. And he didn't die. Or get hives or welts. Annie noted with some interest and pleasure that he was making Walter, who had, seconds earlier, seemed all-powerful, squirm. He did like doing that. Annie took a deep breath and licked the tip of Walter's big boy.

Not bad.

Salty, but pleasant. With a nice bouquet. And Annie was in his complete control. Time to go in for the coup de grace. Annie licked and sucked Walter's huge cockhead, running his tongue around the perimeter again and again. Walter was breathing very heavily. A glance at Mrs. Stack revealed that she had put down her knitting, lifted her dress and had her hand in her panties!

This cocksucking was interesting and not as unpleasant as Annie had imagined. Walter and Mrs. Stack were certainly enjoying themselves. Annie cuddled Walter's balls, gave some deep licks and that was it! Walter cried out and began to pump Annie's mouth full of his nut juice. Mrs. Stack screamed and came herself. Annie couldn't breathe, was gagging, then swallowed the tangy cream and all was well. He sucked and licked Walter clean, then lay next to him.

Mrs. Stack applauded. Walter kissed Annie again and again.

Annie loved approval.

Apparently he had a talent for cocksucking. But the thought of that monster in his bottom filled him with dread.

Walter needed a break. He kissed Annie for a while, then had Annie straddle his shoulders, facing his feet. Annie lowered his soft, pink bottom onto Walter's face. What was Walter going to do?

Annie found out. Walter kissed, licked, and tongued Annie's most tender and secret place, making it wet and making Annie cum, helplessly twice, all over Walter's chest and stomach. He was killing Annie with pleasure. He put his fingers, one, two, and then three, into Annie's tiny hole and poor Annie blew goo yet again.

Annie was losing the last of his masculinity very rapidly.

If he hated all this so much, the sissy asked himself, why was he spurting all that cream?

Good question.

Annie felt more open down there, but knew that rammer could never fit in his bottom.

Walter was apparently less skeptical.

He removed Annie's bottom from his face and with real tenderness, placed Annie on his stomach with three large pillows propping his bottom up as a pretty target of lust. Annie was scared. Fresh tears appeared on his pretty eyes. But Walter was on a mission. Annie's nipples, suddenly very tender, rubbed against the sheets. Walter grabbed Annie's hips and mounted him with his body. How degraded Annie felt. How unmanly. How scared. How effing excited.

It wouldn't fit. Walter was going to see. It was too big. Unnnhhhh. Annie felt the head seat itself in his crack. Ahhhhhhh. The drooling pole touched his anus. Eeeekkkk. It was pushing in. Annie yelped, but the complete insertion of the huge mushroom didn't hurt as much as it surprised him. It was going to happen; this man was going to fuck him. He was going to plant his seed into Annie and relieve him of all his manliness. Annie pushed back slightly to make sure Walter didn't fall out. Walter pushed forward and the whole darned thing slipped in. Annie gasped and cried out.

All in all, it was very nice. Annie had to admit. The intimacy. The rubbing on the prostate. The feeling of pleasing another person. And the two frantic orgasms Annie blew into the sheets before Walter finally deposited his huge load into Annie's ravaged bottom.

Walter kissed his sissy lover for a long time before he went limp and Annie's bottom rejected Walter's cock.

As Walter popped out, Annie felt something pop in.

Mrs. Stack said, "That's a butt plug, Dear. You wouldn't insult your lover by rejecting his load, would you? Plus, it will make you lubed and ready for the next time. Now come, Dear. We have to clean you up, fix your make-up and get you into this black, naughty Panty Boy's Secret outfit I got for you."

Annie arose from the conjugal bed in a much better frame of mind. He was a sissy and he could please men beyond anyone's imagining. If he had stayed a "man," women would have scorned and cheated him. He felt better about his future. About tomorrow, which as Annie knew, was only a day away.

 

Chapter Four – Wet Panties

 

For reasons he didn't know, Nancy was an exceptional sissy. The exact sissy for the Halloran sisters, Meg and Peg.

Mrs. Cummings was always on the lookout for a sissy of Nancy's "unusual" abilities. She was delighted when she got the reports from the uncles that Nancy was Halloran-worthy. Mrs. Cummings had to verify the diagnosis herself, of course, but she found it to be true.

A delightful development.

The Hallorans paid top dollar for a sissy to their liking – only two others had filled the bill thus far. It appeared that Mrs. Cummings' bloated coffers would be bulging even more.

Nancy was also exceptional in ways beyond that "attribute" prized by the Hallorans.

His mother was a dedicated feminist who cuckolded her sniveling husband repeatedly for years, then, when Nancy was 16, feminized his father. Too rich and too lazy to feminize Nancy herself, she dispatched him to the experts at Cummings Academy.

Nancy was probably the prettiest sissy to ever grace CA's pink halls. He had an angelic face, with glowing blue eyes and naturally blonde hair that, left to grow, had formed into dozens of enchanting ringlets.

Even before he had taken to stockings, heels, skirts and panties, Nancy had been propositioned by more than a hundred men. Heterosexual men, driven by a stiff cock and an obsession they could barely understand.

Nancy didn't seem to be attracted to men. Or to women. He seemed to be a young sissy looking to find his way.

Some of the other sissies wanted Nancy in their beds and all of the uncles did. Desperately. He would be fair game for the uncles after "export" weekend. And they were ready.

No one would force himself on Nancy. The hope was that export weekend would set him right about his future as a source of intense pleasure for the men Nancy chose to favor.

But that wasn't why the Hallorans wanted Nancy.

Uncle Rasheed drove Nancy to the Hallorans that Saturday morning. Like all the uncles, who were former teammates or opponents of the late Bruno Cummings, Rasheed was in awe in Nancy's presence. These were men who had sissies for breakfast, lunch and dinner and yet, they all wanted to be the first, second, third or 100^th to occupy what they imagined was a tight, beautiful pussy on a spectacular sissy.

Nancy sat in the passenger seat serenely. He had seen his Daddy feminized and saw that his Dad seemed to enjoy his new station. So Nancy had an open mind. He also knew what the mirror told him. As a sissy, he would rule the earth.

Rasheed sneaked peeks at Nancy's stockinged thighs. Nancy was wearing a pretty pink top; black, micro-miniskirt; seamed, tan stockings; lacy, white garter belt, and naughty, pink, five-inch-stiletto sandals. His six-inch cock and big, pretty ball sack were encased in tiny, lacy, white panties. His facial beauty would melt a steel girder.

Rasheed sighed as they arrived and he dropped Nancy off. Rasheed consoled himself with the thought that he would be spending a cum-filled afternoon with the lovely Nicole, followed by an evening and night with the sumptuous Heidi. Still, none of them were Nancy.

Nancy knocked on the Hallorans' door.

Meg opened the door and stood there with Peg. They were very pleased. This one was a knockout. And if he could do what they wanted…….

Mrs. Cummings had never let them down.

"Come in, Dear," Meg said. "You must be Nancy."

"Yes, ma'am," he said.

Peg said, "I'm Peg and this is Meg. Please call us that.'

Nancy nodded. Meg and Peg were about 40. Attractive. Shapely. Well-dressed in short skirts and heels as high as Nancy's.

"Let me get my bag," Peg said. "We're going to take a walk."

Nancy didn't expect that. If he knew, he would have worn shorter heels. Still, Nancy liked high heels. They made him feel sexy. And he walked easily in them.

Nancy didn't expect the ladies' bags either. While Nancy carried a tiny, frilly sissy handbag, the ladies each carried big, full contraptions. What was in them?

They walked, chatting about nothing. A city park was three blocks from the ladies' home and the three sexy babes found a park bench. Men would slow down as they walked by. Meg and Peg were watching Nancy to see how he reacted to men's interest. After a few minutes, they got the reaction they wanted.

Nancy had a stiffie.

Then things got moving.

Meg did. Peg talked.

Meg lifted Nancy's skirts as Peg spoke.

"Those were some cute men, weren't they, Nancy?"

Nancy nodded.

Meg eased Nancy's delicious panties up and over his stiffie.

Nancy looked at the ladies with a silent plea. This was a public place. People will stare. They were staring.

"Do you see the way those men look at you, Nancy? They want you."

Tell me something I don't know, lady, Nancy thought. Meg eased Nancy's panties over his garters, down his shapely legs to his ankles, then off completely.

Nancy's stiff cock was exposed to passers-by. He was humiliated. And beginning to get very excited.

"Look how they look at you, Honey," Peg continued. "Those men want to throw you over their shoulders and take you home with them. They want to grab you by your blonde curls and drag you home, as a caveman would."

Meg wrapped Nancy's panties around his cock and used it to wank him most deliciously.

"They want to throw you on their beds, pull their cocks out, get on top of you and put their big things in you. In that little hole. The hole you want to protect. But the men, won't stop. They'll get on top of you and dominate you. They'll tell you how beautiful you are, but they'll have only one objective. To push into you and leave their sticky seed in you. Violating you. Look at them walking by. They're violating you now in their minds. Do you want men to do that to you? Do you want their cum in you?"

Nancy looked at the men passing by. Sneaking looks at his beauty and his cock. Wanting him. Needing him. Meg's hand was so skilled. The things Peg was saying. The humiliation. Ohhhhh.

Nancy squealed and began to pump his sticky spunk into the panties wrapped around his cock. A passing-by man or two fainted.

And Nancy pumped some more. A whole lot of goo.

Meg and Peg smiled to each other, then began to giggle. The panties were absolutely DRENCHED in sticky cum!

THAT was the attribute they wanted.

Meg reached into her bag and pulled out a plastic, zip-loc bag and a Sharpie pen. She marked the bag with date, time, location and circumstances, put the panties into the bag, placed the panties back into the big handbag, then withdrew a fresh pair of little pink dazzlers.

Huh? Nancy thought. Well, at least he would be getting some panties back on.

Not so fast.

This time, Peg manipulated his pink popsy with the panties as Meg did the narrative.

"Look at those men, Nancy," Peg said. "They saw you cum and they're imagining what it would be like to have you in their beds, making you cum for them."

Nancy was stiff and panting again, just as Mrs. Cummings promised. He was permanently humiliated, yet aware of everything that was happening with the leering men.

His ears were flaming with shame and his balls were boiling with lust. And then they exploded. Into the new panties. Lots of cum. Hot and plentiful. And incredible sound effects from Nancy, Meg, Peg and the crowd.

The soaked panties were catalogued and slipped in the bag, with a fresh pair produced. Nancy slipped on a pair of black, satin, thong panties with a pouch for Nancy's privates and the three babes got up and wiggled out of the park.

 

The show was over for that location, but the 20 or so men and boys who had observed the best sex show west of Bangkok murmured amongst themselves. Then they hurried home to relieve their "tensions."

The public library was at the edge of the park. Meg and Peg led Nancy inside.

"That was fun, wasn't it, Nancy?" Peg asked.

Nancy only whimpered. He wasn't sure what it was, but he had another hardon, which pleased the sisters very much.

Nancy had been hard almost 90 percent of the time since he had been in girlish frillies. There was just something so thrilling about being a sex object, even for the uncles and the other sissies.

Nancy faced the inevitable. He knew he would have to start sharing his feminine sex attributes with some of the people it drove wild.

He was acutely aware of the stares from male book patrons as he clacked around the library. They weren't undressing Nancy with their eyes. They were impregnating him with their eyes. Planting their seed into him. Wanting to own him.

Oh. To be possessed by a man.

That thought was putting Nancy "on the verge."

Quick-witted Meg noticed, dragged Nancy to the stacks area, then pulled his panties to his ankles. As Peg watched, Meg stood behind Nancy, reached around his right hip, lifted his skirt, and, using another pair of panties, massaged his tingling prick to a gusher greater than the last.

The sisters were delighted. This sissy was a treasure! Beautiful, hot as blazes and an ocean-like reserve of hot, sissy cum.

Poor Nancy was in the sweet agony of cumming when he saw a man in the adjoining stack watching the whole thing. More embarrassment!

The sisters saw him and, horror of horrors, spoke to him.

"He's awfully pretty, isn't he?" Meg asked the young man.

Nancy's eyes were watering from shame and lust, but he was able to see that the man was quite attractive, in his mid-20s and very interested in Nancy.

The young man said, "The most beautiful, most feminine person I've ever seen. And he has a cock. How wonderful!"

Poor Nancy. The praise and shame were giving him another throbbing stiffie.

"Are you always erect like that?" the young man asked Nancy.

Nancy was too mortified to speak, so Meg answered.

"This is really his first sojourn in the world since his feminization. I'm afraid it's all too exciting to him."

"My name's David," the young man said. "Before I can ask you to marry me, I have to know your name so I can put it on the license."

Nancy blushed hotly and his cock twitched. That was just a pickup line, wasn't it? Was he serious?

Nancy looked at the floor and said, "Nancy."

David said, "What a pretty name."

Even Nancy knew that was a line.

Meg said, "I think it would calm him down if a man made him cum. You can do it if you like. Just catch his cream in this pair of panties."

David looked delighted as he accepted the pink bikinis from Meg. "Is that OK with you, Sweetheart?" he asked.

Nancy looked at Meg and Peg, who were nodding approval. He sniffled out an "OK," but the idea had his cock throbbing.

David surprised them all by kissing Nancy sweetly, then tonguily, as he stroked Nancy's excited cock. David was a good kisser. Though it was Nancy's first kiss, he did a great job of giving back all that he got.

Then Nancy unzipped David and pulled out his cock.

That made the Hallorans very happy. And Mrs. Cummings even richer. The way this was going, they would double her fee.

The two unlikely lovers kissed and stroked each other's cocks. David reached the Promised Land first and it was a good thing that Meg slipped Nancy a fresh pair of panties to catch his cream. It was a deep, satisfying cum for David and he kissed and stroked Nancy to a creamy emission equal to his own – caught yet again in fresh panties.

Nancy didn't want to leave. Neither did David. Neither did the six library patrons who saw the whole thing and came in their own boxers.

But the Hallorans had an agenda. Meg spoke privately with David for several moments. Nancy fretted about the unfairness of having given himself to his first man, then being forced to watch that man walk away.

David kissed Nancy deeply, then said, "I'll be back," thus not terminating their relationship. Would he really? Nancy hoped so.

The ladies said lunch was the next agenda item, so the three lovelies walked to a nice restaurant called "Les Trois Jeunes Filles,"

Nancy was distracted, thinking of David and the events of the day thus far, but he had to admit, the food was good.

So were the cummy handjobs administered under the table first by Meg (8.47 fluid ounces of cum), then Peg (8.75 more ounces).

When the bill came, Meg asked to speak to the manager, who appeared moments later – a nice-looking man of about 40. Like every other breathing heterosexual male, the manager was in carnal shock at Nancy's beauty.

Peg said, "Sir, I'm afraid we don't have any money to pay the $53.45 tab (plus tip), but our beautiful, sweet young sissy friend would love to suck your cock and swallow your cum to cover the bill."

The manager's face twitched, almost imperceptibly. Then he said, "Certainly, Madam. Please follow me, ladies."

Resigned to his messy fate, Nancy docilely followed the group to the restaurant's storeroom.

Peg produced a soft pillow from her bag and thoughtfully positioned it on the floor for Nancy's knees. He assumed the position.

Nancy looked at the manager, who was staring at Nancy as if it were the luckiest day of the restaurant man's life.

Nancy considered the man's cock, which was breathing free air since the man had dropped his drawers. Nancy hadn't seen many cocks close up and had never touched one with his pretty lips. Both streaks ended simultaneously.

Nancy gave the delighted man's prick a tentative little kiss. It was just skin, he told himself. But when he saw the man's ecstasy, Nancy knew it was very important skin. Nancy was in charge of the restaurant man's happiness. The little doll could take him to heaven or put him into a state of disappointed despair. A little lick wouldn't hurt. Then a bigger one. The man was drooling sticky goo, just as Nancy did when he put on his tiny nightie and looked at himself in one of the hundreds of mirrors at Cummings Academy. The goo tasted nice and Nancy was making the man happy. Then it occurred to Nancy that men would do anything Nancy wanted if the sweetie would just submit to them as he was to the restaurant man. Kneeling. Sucking and licking. Mmmmm.

The manager was in paradise. Looking down at a kneeling, magnificently gorgeous, feminine treasure. Feeling the lovely's tongue massaging his thousands of cockhead nerve endings. Listening to the narrative of the wacky, middle-aged babes.

"That's it, Nancy," Meg said. "Lick it softly, then pick up the tempo. Lick around the rim of the mushroom. Mmmmm. He liked that."

"Tongue his peehole," Peg said. "Men adore that. Now take these panties and stroke your own business as you suck his big thingee. Good girl. Use your other hand to cuddle his balls. He likes that too. Are you going to cum? Catch it! Oooohhh! Good girl! Another gusher! You're amazing. Look. He's going to cum too. Catch it in your mouth. There it goes! So much! You excited that poor man very much. How does it taste? I'll bet it's delicious. Mmmm."

Nancy swallowed the man's spunk hungrily. It was very tasty and Nancy was proud that he had done such a good job. He loved approval, even if it came from Meg and Peg.

Nancy realized that he would have liked to have sucked David's cock better. What an odd thought.

The restaurant man helped Nancy to his feet and gave him a long, grateful kiss that had Nancy gasping and cumming into the blue bikini panties that Peg was rubbing around his cockhead. Another soaking!

The three beauties bade farewell and walked to Meg and Peg's home without incident.

Then things got odd.

Meg and Peg escorted Nancy to what appeared to be a bedroom they shared. They stripped to their lingerie, including bras, garterbelts, stockings and big heels, and insisted that Nancy do the same.

No cocks sprang out when Meg and Peg removed their panties. They were genetic women. No tgirls would be that strange.

Peg walked to the east wall of the bedroom and began to string a long, pink-ribbon clothesline from a hook to a similar hook 15 feet away on the south wall. With Meg's help, they began to hang the panties drenched by Nancy's cum on the line. It appeared that the line was about 40% filled.

Nancy knew that he was mixed up in odd business. The humiliation had been intense. But the orgasms had been awfully good.

"We have 23 more hours with you, Honey," Meg said, "You're going to be the only sissy who ever filled that line."

Nancy shuddered, then lay back with his head on a pillow as Peg directed. Meg straddled his shoulders and lowered her sopping pussy onto his face. Peg took his cock into her expert mouth, with several pairs of fresh panties at the ready for Nancy's drenchings.

Nancy learned fast how to eat pussy. And when David showed up at 8 p.m., as invited, to pork his pretty bottom all night long while the sisters licked each others' muffies, the sisters had to put up a second clothesline.

 

Chapter Five – Panty Partners

 

Rhonda was not entirely sure what the best postings for Amanda and Jeanette would be for their first "export" weekend.

Amanda was a very enthusiastic sissy who creamed the first pair of panties he ever put on and almost every pair since. His mother could have saved herself $120,000 in "instructional fees" by taking Amanda to a lingerie department, then to Elizabeth Arden for a makeover. Rhonda mused that Amanda would have been on his knees, in make-up and frillies, sucking the biggest cocks he could find in no time.

Jeanette, on the other hand, was a problem sissy. Jeanette was absolutely positive that he was a boy, a real boy, and that his mother would release him from what he called "this madness," once she realized what a mistake she had made. Rhonda knew that Jeanatte's fate was sealed, even if he didn't.

Jeanette cringed when the uncles pulled his panties down three times a day and masturbated him to glorious, spurting, gut-wrenching cums. Anyone would cum if wanked like that, Jeanette assured himself. He was a heterosexual male whose circumstances, while unfortunate, were only temporary.

Rhonda noted with distaste that Jeanette didn't participate in some of the "cuddle sessions" that many of her sissies engaged in with each other. She had found that frequent ingestion of a fellow sissy's sticky juices eases the way for the inevitable complete submission to a man.

She had considered just renting Jeanette out to Arthur Shockley, a sissy enthusiast of some note, who spanked sissies' pretty bottoms when they resisted the insertion of his enormous cock in their bottoms. Once they had experienced his strict, but satisfying love, they never needed their bottoms warmed again. Except by his cum.

But that was too direct. And Rhonda prided herself on her subtlety.

Amanda and Jeanette were summoned as the last two sissies to be exported that lovely weekend.

Amanda looked hot-to-trot and ready for a weekend of hot cum on his face, in his mouth and, oh yes, in his bottom. Like the rest of the sissies in his training group, however, Amanda's bottom or mouth had not been visited by a man's cock. The naughty uncles had slipped their fingers into his deep hole many times during the heavenly milkings. And during the cuddle sessions with Cynthia and Melissa, tongues had gone where no man had gone before. Now Amanda was ready to take a big, stiff, penis, attached to a strong man, into his sissy hole.

Jeanette just wanted all of this horrible stuff to be over.

Amanda and Jeanette were tasty little confections, especially, ironically, Jeanette. Despite his misgivings, Jeanette's long, straight, black hair framed a lovely face, perfectly enhanced by Jeanette's expertly applied make-up. He was a bit heavy-handed on the eyes perhaps, but that gave Jeanette a slightly tarty look. Even Jeanette saw a beautiful, slim girl when he looked in the mirror. A girl with long, delicious legs, walking easily in skyscraper stilettos.

Amanda was jealous. While he was blonde and an easy "10," Amanda knew that Jeanette was an "11." A pity that Jeanette was so stuck up. Amanda's cock petrified every time he saw Jeanette. But Jeanette wouldn't even kiss the other sissies.

Maybe that would change that weekend.

Rhonda brought Amanda and Jeanette to her office for a bit of a pep talk before sending them off on their sodomistic sojourn.

Amanda stood eager and ready, with a clear lump in his tiny skirt. Jeanette looked frightened and angry, but also sported a sissy woodie tenting his pink, plaid, pleated miniskirt.

Rhonda smiled and said, "Ladies, I'm sending you out together for a lovely weekend with two delightful men. Mr. Paul Brown and Mr. Bill Evans are long-time friends of Cummings Academy and I expect that you will show them respect and AFFECTION for the entire weekend. They have a deep fondness for our 'girls' and I have never disappointed them. And I never will. Is that clear?"

Amanda eagerly agreed. Rhonda chuckled. That one would have his panties off when the first man smiled at him.

Jeanette was miserable. But he whimpered out a "Yes, ma'am."

Rhonda was certain that the little strategy she had worked out with Paul and Bill would help Jeanette resolve his silly issues.

"Being a sissy is all about submission to men and the enjoyment of feminine pleasures," Rhonda told the unmatched pair. "It's to be enjoyed, not dreaded. Amanda is enjoying himself, as have all the sissies I've trained. Jeanette will too. I'm certain because I see Jeanette's feminine beauty and how femininity excites him. Adoration by men will do you both a great deal of good. Now go and have a wonderful weekend."

Jeanette was sniffling as they left the office. Amanda hugged him and said, "Don't cry, Sweetie. It's going to be wonderful."

Jeanette knew that was false, especially since that obvious sissy faggot, Amanda, was saying it. Still, for a sissy faggot, Amanda was kind of pretty. And no one had hugged Jeanette in so long.

Jeanette was understandably worried about how stiff his cock had been since he arrived at Cummings Academy. He remembered with shame how he had cum hard the first time he had put panties on. And the second time. And most times since. It was his parents' fault for circumsizing him. With no protective foreskin, his unhooded little cockhead was no match for the silk, satin and nylon little dazzlers those perverts kept giving him to wear.

He also couldn't help getting stiff and often cumming when he put stockings and garters on. They felt so smooth on his shaved, lotioned, powdered legs that big, sticky spurts just seemed to happen.

Sometimes, when Jeanette was looking in the mirror at his pretty face, watching his bare, pink bottom jut back from the precarious perch created by his five-inch heels, he had bad thoughts. Jeanette would imagine that he was a girl and that a man was looking at him as he was posing and teasing. That very bad thought always ended the same way. A knee-shaking orgasm, followed by hours of shame and remorse.

Why did he even have thoughts like that? He tried to stay away from those faggot "uncles" who milked all the other sissies (he called them his fellow prisoners). But the uncles would milk poor Jeanette the required three times a day. Some of the "cellmates" let the uncles kiss them and even let the uncles finger their tight bottomholes as they were milked. The sounds that emerged from the sissies' throats when those sissies came made Jeanette very ashamed for them.

Thank goodness those milking "extras" were voluntary.

When milked, Jeanette would lower his panties, hold his skirts up and look away as those bad men with skilled hands made him cum so hard he almost fainted.

Despite Jeanette's best efforts, he almost enjoyed being milked.

Just as he was almost enjoying Amanda's comforting embrace outside Mrs. Cummings' office. Amanda smelled awfully nice. And looked like a girl. And Jeanette liked girls.

Amanda broke the clinch, but held Jeanette's hand as they clacked along through the front door to the van that would take them for their cummy weekend.

Amanda wiggled into the back seat, as full of expectation as Jeanette was of misery.

After a 30-minute ride whose silence was only broken by Jeanette's soft sobbing, they arrived at a very nice, large, white house.

Amanda was delighted to see them greeted by two VERY hunky, handsome, buff men in their late 40s, obviously Paul and Bill.

Jeanette was trembling and holding onto Amanda for support. The Cummings Academy van drove off and Paul and Bill introduced themselves.

"Thank you for coming, girls," Paul said. "Can we get you something to eat or drink?"

Jeanette seemed too scared to speak. Amanda's eyes glowed with lust as he said, "No thank you. I already see everything I want."

Men love that talk. They really do. The cornier the better. Men are simple creatures after all.

Bill said, "Let me show you the master bedroom then. You'll want to strip to your bras, garter belts, stockings and shoes. You won't need your skirts, slips, tops or panties."

Jeanette groaned and clutched Amanda harder.

Paul and Bill escorted them to the bedroom, then Bill said, "I hate to do this to such beautiful ladies, but Paul and I have a business thing we have to attend to before we join you. Please let us know if you need anything."

"Thank you," Amanda said. Jeanette looked as if he had gotten a temporary stay of execution.

They entered the huge bedroom and closed the door.

Amanda was in heaven. His little sissy pussy was about to be worshipped and penetrated by the kind of older men – daddies – he had always dreamed of. He removed his top, skirt. slip and panties quickly and sissied into the bathroom to fix his make-up.

When he came out, looking sassy and slutty with a nice stiff poker ready for anything, Amanda saw Jeanette still fully dressed.

Taking pity, Amanda clacked over to Jeanette and hugged him. "Now, come on, Honey. You have to do as they say. You know how bad things would be for you at Cummings Academy if Mrs. Cummings got a bad report.

Jeanette knew. Hard, naked spankings would only be the beginning,

Still, he said, "I can't."

Amanda tutt-tutted, saying, "Of course you can. Let me show you." Amanda removed Jeanette's top, then skirt and slip, then panties.

Amanda said, "Give in to the pleasure, Sweetheart. You know your beauty makes you hot. It makes me hot too. Look.

Through his stinging tears, Jeanette beheld Amanda's very nice woodie and pretty balls. He looked at his own package and noted a similar stiffness.

Amanda hugged Jeanette and gave him a tiny kiss on the lips. "You're so beautiful. Can you stop crying for a minute? For me?"

Jeanette sighed, collected himself, and stopped sobbing.

Amanda smiled, then kissed Jeanette full on the lips.

"You're a very brave girl, Jeanette." <Kiss> "We're going to get through this together." <Bigger kiss>

Jeanette liked those kisses and even kissed back a little. Amanda was so pretty and feminine. And he smelled so good.

Amanda said, "Can I have a little smile? Just a little one?"

Jeanette bravely offered one. Then Amanda kissed him more passionately, open-mouthed, with tongue.

Jeanette was startled, then kissed back. It was very nice.

And even better when Amanda began to rub his wet peehole against the underside of Jeanette's cockhead.

A brief, "This is wrong" thought flashed through Jeanette's mind. Then he helped Amanda by rubbing back.

They kissed sweetly, mixing sticky goo. Two pretty girls with stiff cocks. Being observed by two randy gentlemen in the next bedroom who were watching them on a hidden-camera feed.

Paul had won the coin toss and had selected Jeanette as his partner for Saturday. They would switch at midnight and Bill would give up the lovely Amanda. Or maybe they wouldn't, if everyone was happy. They were both sissy treasures. What a great idea Rhonda Cummings had had to leave them alone for awhile so Jeanette could dismount from his high horse.

Bill noted with delight that the sissies were now on the bed.

Jeanette was on his back with Amanda straddling Jeanette's hips. They were still kissing rubbing sticky cocks and good things were very imminent.

Jeanette was gasping for air and, from somewhere, came a girlish squeal as he began to spurt a very large quantity of sperm. Amanda tongued Jeanette's tonsils as he answered Jeanette's ecstasy with huge globs of his own.

Ohhhhhh.

Jeanette felt something leave him. Something he didn't need. Something he should have never had.

Then he felt Amanda licking all the cum from his hand, tummy and chest. Amanda was reversed on him and Amanda's cock was inches from Jeanette's glossed lips.

Jeanette accepted the penile invitation. He took Amanda's gooey clitty to his pretty lips and kissed it lovingly. He licked up Amanda's cum, surprised at the pleasant taste, then began to lick and suck Amanda's cock with a purpose.

The sissy angels sixty-nined each other to heaven. In the afterglow, they kissed and cuddled and toyed. Licked and sucked. Every now and then there would be a gasp, or a tiny squeal, and another tribute was paid to the gods and goddesses of love.

Paul and Bill watched two-and-a-half hours of their Sapphic love – a much greater show than the Super Bowl – and more…..satisfying.

Then the men joined their weekend darlings.

Jeanette was so happy. He welcomed the men and their loving attentions. But he got his sissy back up when Paul wanted to take him to another room for the fucking every sissy needs. Jeanette would not be separated from Amanda.

The men kissed and teased and sucked and licked the dolls for over an hour. Jeanette was delighted to have her bottom eaten by Paul's long tongue. He squealed and came twice, just from that. But it also excited him to lock eyes with Amanda as they were both being eaten out by dreamboats.

When the time to be penetrated came, the girls lay next to each other on their backs and held hands as Paul mounted Jeanette and Bill mounted Amanda.

Jeanette screamed with pleasure as the last wisp of manhood left him and a man's wonderful cock injected him with the very essence of life.

Amanda's grip on Jeanette's hand tightened as Bill heaved and bucked and filled his bottom with sticky seed.

"There's no turning back now, Honey," Amanda said to Jeanette.

Jeanette kissed Paul with lots of tongue, then said to Amanda, "Lead on, Darling."

And Amanda did. When the guys wimped out and fell asleep after depositing only four loads in each sissy's bottom, Amanda and Jeanette kissed and cuddled and spurted their sissy cream on each other all night long.

When the men woke up, everyone was ready for more.

It was a great weekend.

 

Chapter Six – Panties Back On (Temporarily)

 

On Sunday afternoon as the last exported sissies walked, bowlegged, sore, but happy, back into Cummings Academy, Rhonda greeted them all warmly.

"I've received magnificent reports about all of you. I'm very pleased. You've crossed a bridge, ladies. From now on, your lives will be filled with feminine pleasures as you submit to men. They in turn will they adore you and do anything to please you. Your mothers sent you here as punishment or just because they didn't want to deal with you. You will have the last laugh. Men will lay riches at your feet and your lives will be filled with pleasure.

"Beginning now, from the looks of those uncles standing behind you."

The sissies turned to look. Ten naked, hunky uncles stood stroking their cocks.

Jeanette moved first, moving to Uncle Jack, stopping to remove his panties, then walking off with Jack to Jack's room.

It's always the slow learners who end up the randiest, Rhonda said to herself.

 

If you liked this story, didn't like it, or have an idea for a story, please contact me at gingerfred99@yahoo.com

 

 

 

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