Mothered

by Gingerfred Man

 

Chapter One – Matty’s Mom

Some people said Annette Marlow was an overprotective mother, but there was no doubt that she loved her only child very much.

Fourteen-year-old Matty Marlow was easy to love. He was sweet and innocent. He was intelligent and cute as a button. Matty totally adored his mother and would do anything for her.

And Annette returned all of Matty’s love.

Annette was still a very beautiful woman, with an excellent figure that included very large breasts and long, luscious legs. Men noticed Annette and occasionally, Annette noticed men. She was a good woman, who cared about doing what was right. Although she did have her idiosyncrasies.

But who doesn’t?

Matty’s father disapproved of the way Annette was raising their son. That was why he gave up and abandoned them when Matty was six.

"You treat Matthew like an infant," Greg Marlow would say. "He’ll never be a man. Why don’t you cut the apron strings and let him grow?"

Annette never understood what her former husband meant by all that. Nor did she try. Mostly she was interested in keeping her boy safe and happy.

"Safe" was the hard part. Matty was always a very happy little boy. Always. But now that he was 14 and in high school, the caring mother was facing all sorts of new challenges.

Annette knew that she and Matty would jump those hurdles. They always had.

One afternoon, early in Matty’s freshman year, Annette was reviewing Matty’s situation. She was concerned about the other boys in school. In the lower grades, the boys had never been very kind to Matty, but the volume on that had been tuned up considerably over the past year. They called him a sissy. And worse.

Annette knew that Matty was their superior. In every way that counted. And Matty would end up living a better life than any of them. That was, indeed, the best revenge.

All the boys weren’t mean to Matty. Zack Lincoln had been nice to Matty since first grade. They weren’t best friends or anything, but definitely friends. And Zack, a big, strong boy with character to match, had often defended Matty from a variety of would-be bullies. Annette was grateful to Zack, but she knew that she would have to plan better for her son than just relying on Zack.

There were some teachers who were nice to Matty as well, especially that Mrs. Louis, who was young and beautiful, as well as being a kind, caring teacher. And Annette could always count on her sister Janice and Janice’s son Chrissie, who was very much like Matty in some ways, but was much more aggressive.

She would have to think about that later, because her little prince had just gotten off the school bus and was entering their home.

Matty’s sweet face and beautiful attitude lit up the room. He ran to his mother to embrace her.

"Did you have a good day in school today, Sweetheart?"

"Oh, yes, Mommy," the little angel said. "Did you have a good day?"

"Yes, thank you, Dear. Are you hungry for your after-school snack?"

"Oh, yes, Mommy. Very."

He’s so sweet, Annette thought. She sat on the couch and took off her blouse. Matty got himself into a comfortable position, lying on the couch with his head on Annette’s lap. Annette unhooked her industrial-strength bra and draped it over the arm of the couch. Matty opened his mouth hungrily and tilted his chin up to receive his mother’s wet, right nipple into his mouth. The lad sucked greedily as Annette cooed with motherly pleasure.

As her dear boy drained each breast in turn, Annette recalled that breast-feeding the boy at six was one of the reasons Matty’s father left. Annette wondered what he would think if he saw them still doing that when he was 14. Well, she didn’t care. They both loved the experience and Matty had never had a sick day in his life. Plus Annette had to admit that she liked the extra heft it had given to her titties all those years.

People could scoff all they wanted. What went on between Annette and Matty was their business.

 

Chapter Two – Matty’s Teacher

Stephanie Louis was one of the happiest people on the face of the earth. She had a wonderful, gorgeous husband who adored her. She was a skilled and effective teacher, a profession she loved almost as much as she loved her husband. And she was knockdown, drag-out babe-o-licious.

Tall and slender, with wide hips, tiny waist and huge gazongas. Long legs, tiny, perfect feet and an ass to carve into Mount Rushmore. And her face was angelic, but had the innocent-with-a-pinch-of-naughty look that men lie in bed and drain their balls dreaming about.

That day, like most days, Stephanie had arrived home an hour and a half before Blake got off the train from the city. As always, she used the time wisely, allotting 30 minutes to the preparation of a delicious meal and 60 minutes to the preparation of her delicious self.

When Blake Louis walked through his door that evening, he reminded himself that he was that lucky guy we always wanted to be, but never quite got there.

His Playmate-of-the-Year-worthy young wife was in full warpaint, with lingerie, stockings and very high heels that begged for a marital consummation.

He was weak. He chose stupefying sex over a brewski and a Seinfeld rerun and kissed Stephanie with equal parts love and lust.

Blake could be an animal. Stephanie was so happy when he was. He carried her up the stairs, and laid her on her back. He ripped his clothes off (fortunately, he worked for a clothing manufacturer and never paid retail) and flung his hard, delicious, naked body on top of his wife’s.

Stephanie squealed happily. She loved sex with Blake very much. The couple fucked at least three times a day, even though they had just celebrated their fifth wedding anniversary, and enjoyed every carnal moment.

Blake’s cock was at its red, throbbing, angriest and he rubbed it against his wife’s panties as he kissed her.

That motion always made Stephanie’s cock harden and throb too, and she was delighted when Blake pulled her panties down so they could rub their bare cocks, exchanging goo as they kissed sweetly.

Stephanie was anxious. She nibbled her husband’s earlobe, then whispered, "I lubed myself. I’m all ready for you. I want you."

Yum. Blake locked eyes with his angel, then placed her calves on his shoulders. As they had done hundreds of wonderful times before, Blake’s cock entered Stepanie’s perfect bottom. She gasped and panted with pleasure. Blake stroked Stephanie’s cock as he fucked her, kissing her, praising her beauty and lovemaking skill and telling her how much he loved her.

Stephanie wiggled a little so that Blake’s cock would clip her prostate just right. Then she did a "naughty." She reached around and entered her husband's bottom with her manicured fingernail and wiggled it as she explored. Blake panted a bit. Fucked his lovely angel. Held off from cumming until Stephanie’s eyes widened and she shot a big creamy load all over her perfect tummy. Then moaned and gave Stephanie the hot load he had been saving for her since their last lovemaking, that morning.

They kissed and talked about their days. At that point, they usually had dinner. But sometimes "round two" seemed a better option. It was that evening.

Blake was on his back as Stephanie knelt and licked Blake's cummy cock and balls. Blake saw Stephanie’s intent and he liked it. She got him rock-solid, then straddled his hips and sat on his cock. As she bounced up and down, Blake watched Stephanie’s big titties jiggle and bounce as they fucked.

Stephanie was in control of their lovemaking and she used every muscle in her bottom to caress and milk her man’s cock to another spermy explosion in her girlish "pussy."

Realizing his Baby hadn’t cum a second time, Blake beckoned Stephanie to straddle his shoulders and feed him her shiny throbber. He gave her pretty balls a sucking that had her on the verge, then took her off the cliff with some world-class tongue work on her cockhead.

Eventually, they ate dinner. Or you could call it refueling for the next round.

They were a very happy couple.

After dinner, they returned to bed. They were in no hurry that time and spent a lot of time cuddling, toying and sharing intimacies.

As Blake caressed Stephanie’s long, thin clitty, he thought about their early days. Blake and Stephanie had been boys together growing up. They went to the same schools, but Blake was two years older. Blake knew Stephanie was "different" from around age eight. Stephanie, then called Gilbert, had always been delicate and girlish. Rather than be repulsed by those traits, Blake, a very masculine lad, had feelings for Gilbert that troubled him deeply.

Blake skinned Stephanie’s foreskin back, a move that always made his lovely darling gasp and squeal softly. How could Blake have ever misunderstood his feelings for the most beautiful, feminine person on earth?

When Blake was a junior in high school and "Gilbert" a freshman, Blake worried that he was gay. Blake was able to convince himself that he wasn’t only by applying the logic that he was attracted to girls very much. And he was only attracted to only one boy in the world – Gilbert. Very attracted. Lie-in-your-bed-and-wank-yourself-dry attracted.

Stephanie was remembering their fear-and-guilt-challenged-but-ultimately-glorious courtship and resolved anew to help others miss some of the potholes she and her beloved Blake had encountered.

"That feels so good, Blakie, but my titties are so lonely. You haven’t sucked them all day!"

Men say they don’t like talk like that. But they do. They really do.

As Blake consumed Stephanie’s huge, brown, right nipple, while tickling her pink treasure bag, Stephanie brought up a subject Blake was a little tired of hearing.

"I know a boy who needs our help, Blake. He’s a sissy. I know he is."

Reluctantly, Blake’s lips left Stephanie’s titty flesh. "Sweetie, I would do anything for you, but you are not, I’m sad to say, a good evaluator of sissies. Remember Charlie?"

Stephanie winced. She had been sure that Charlie was a sissy. He was so troubled. But then she discovered that he was only depressed because his dog had died. Anyone could make a mistake like that.

Blake pushed on. "And let’s not forget Aaron."

Another mishap. Aaron’s parents were going through a divorce, she discovered after a false diagnosis of "sissy boy."

"Sweetie," Blake said, "Every problem a teen has is not related to his need to be a sissy."

He was right, Stephanie thought. Her man was always right. Especially in the sack. But she always managed to win every disagreement. Makes you wonder why.

Stephanie said, "You’re right, Sweetie. I was wrong and you were right. Would you just lie on your back? I want to make it up to you."

Blake knew he was in for the best blowjob ever given on this earth. When Stephanie wanted something, she always gave him one of those. And he always gave her what she wanted. Gladly. Willingly. And it was always worth it.

When Stephanie had swallowed the last molecule of cum in Blake’s body, then kissed and licked and sucked her man to another pounding erection, she asked him, "Can you help me help Matty Marlow be all the sissy he can be, Blake?"

Blake groaned. "You know I will, Baby. Now lie on your side and I’ll get in you from behind. Would you like that?"

"Mmmmmmm," Blake’s angel-for-life purred.

Men are so easy.

 

Chapter Three – Matty’s Friend

Zack Lincoln needed Blake Louis’ advice.

Unfortunately, neither knew the other existed.

If they had been able to communicate, Zack would have told Blake all about the feelings that were attacking him, shaming him, but most of all, exciting him. Blake would have told Zack the most important messages of all – "It’s all right. I know what you’re feeling. You’re not wrong. You’re not crazy. I’ve felt the same way, acted on those feelings and I’m very happy as a result."

But there was no such reassurance available for Zack at that time. Instead, Zack was fighting an incredible, consuming attraction he was feeling for another boy – Matty.

The idea of sex with boys turned Zack’s stomach. Zack often fantasized about making love to girls, but no specific girl of his acquaintance.

Ever since "that day," he thought about making love to Matty. A lot.

"That day" was a month earlier. The Saturday before high school started for both Zack and Matty.

Even though they were the same age, Zack had always been kind of a "big brother" to Matty and they had always spent several hours together each week. Zack was the youngest of five and the only boy, so he liked having someone like Matty to protect. Matty was a great kid too. Always happy and positive, even when the other kids teased him about being small and delicate and sissyish. Matty was smart and funny and Zack always enjoyed his company.

Zack was walking by the Marlow’s house at late afternoon "that day" when he saw Matty sitting on his porch waving Zack over.

They greeted each other in a friendly way, just as they always did. Zack sat to talk with Matty, who offered lemonade. Matty went inside and moments later, he and Mrs. Marlow appeared with a tray, glasses and pitcher of home-squeezed lemonade.

"Thank you, Mrs. Marlow," the polite Zack said.

"You’re welcome, Zack," Annette said. "It’s always a pleasure to see you." Annette genuinely liked Zack and thought he was great for Matty. She left the boys alone.

"So," Zack said to Matty. "Are you nervous about starting high school on Monday?"

Matty smiled. He was so darned cute when he smiled. "No. Not really. Are you?"

Geez, Zack thought. Here this poor little runt is going into a situation where the sharks will circle and attack him and he’s treating it like a walk in the park. Zack was always amazed at Matty’s self-confidence and serenity. It was as if Matty could always see beyond the troubles of the present to a better life ahead. For the thousandth time in Matty’s presence, Zack wished he could do that.

"I’m a little nervous," Zack admitted to his friend.

Matty loved the honesty. He got up, walked across the porch, and hugged Zack, saying, "It’s OK, I’ll protect you." And he giggled sweetly.

Good gracious. Matty had never hugged Zack before. He smelled like soap and youth and innocence. Matty only held the hug for a few seconds, then went back to his seat across the porch. But Zack had the biggest, hardest erection of his young life.

That was very disturbing to the fine young man. And embarrassing. Had Matty noticed? He was chattering on as if he hadn’t. What did it mean?

Zack seemed to lose the thread of what Matty was saying, but his other senses were very aware. He noticed that Matty was wearing skimpy, cutoff jeans that barely covered his bottom and that his bare feet were small and pretty. Did he just think "pretty?"

Zack also noticed Matty’s sweet, tinkling voice and easy laugh. Matty’s tank top revealed smooth, creamy shoulders and a hairless torso.

What was happening to Zack?

A short while later, Annette joined the boys and invited Zack for dinner. Mesmerized by his feelings, and against his rational side, Zack accepted.

Zack and Matty played a video game, then joined Annette to enjoy a lovely dinner of meat loaf, mashed potatoes and green beans.

Zack was in no hurry to go home, so after dinner, he and Matty went back out on the porch to talk.

"I’m not going to turn the porch light on, boys," Annette said. "That just attracts bugs."

Sitting in the dark with Matty had Zack tingling in a strange way. A good way. But strange. Matty sat on one side of the porch and Zack the other. Everything would have been all right, but then the temperature dropped.

Even nature was conspiring against him, Zack thought later. Or for him. He wasn’t sure of which.

"Are you cold, Matty?" Zack asked his shivering, underdressed friend.

Matty nodded.

<Gulp> Pause for life-changing moment.

"Come sit with me," Zack said.

Matty zipped over and immediately sat next to Zack. Matty tucked his bare feet under him, then snuggled up to Zack.

Zack felt protective, as he always did around Matty. But his erection had returned, and was more insistent than the last time.

Zack put a brotherly arm around Matty. Matty made a sigh of contentment. Things were beginning to get out of hand. Zack decided to put a stop to things.

There was just enough light for Zack to see Matty’s face when he looked into his eyes. Zack saw need and affection. Ohhhhh. Zack saw something he had always wanted, but was terrified of. Unnnhhh. Zack saw Matty tilt his head up and part his wet lips slightly.

Zack’s heart skipped. It was wrong. It was gay. It was a mistake.

Zack kissed Matty right on the lips. Hungrily. Passionately. It was the nourishment Zack longed for, but could never have. He was so ashamed. He was so aroused!

Zack found Matty’s tongue with his own. They caressed each other’s warm young bodies as they kissed.

Zack had never been happier in his life. And he was frightened beyond measure.

But they kept kissing.

Zack couldn’t stop himself from putting a hand on Matty’s leg and stroking the warm flesh where Matty’s thighs were joined. Ohhhh. Zack’s cock was throbbing as he kissed Matty with his whole being.

Matty cooed and sighed with obvious pleasure, parting his thighs to allow Zack better access. Zack’s hand sought the bottom of Matty’s cutoffs and reached up to Matty’s most private parts. Zack felt two hot, tiny balls in a wrinkled bag, then a very stiff, but very small, tubular object that throbbed at Zack’s touch. Zack rubbed his thumb around the head and almost fainted with lust when he heard Matty issue a small squeal.

Meanwhile, Matty was not idle. He had managed to pull down Zack’s zipper and was feeling Zack’s thick pole through his Jockey shorts. Zack groaned with guilt and pleasure as he felt his friend’s soft, loving hand. When Matty excavated Zack’s cock from his underwear, freeing it to the night air, Zack grunted with joy.

Zack stroked Matty’s little jewel as they kissed, until the little sweetheart squealed a bit more loudly, kissed Zack harder, and spurted several thick, creamy globs of sticky goo over Zack’s loving hand. The dirtiness and pure pleasure of the situation seized Zack and he joined his partner in paradise, shooting thick strands of his manly gunk into the late summer air.

Zack was in heaven……and in its antithesis……simultaneously. His immediate problem was, what did he do next? Did he zip up his pants and pretend nothing happened? Did he blame Matty for being a little dick-teasing faggot and run off? Or did he keep making love with Matty and see what happened next?

His problem was solved for the moment by the slow, noisy, obvious approach of Annette Marlow. When he heard his mother coming, Matty jumped up and took his original seat on the other side of the porch. Zack covered his drooling cock with his hands as Mrs. Marlow looked out onto the dark porch and said, "You’d better get ready to go home, Zack. I told your mother you would be home by nine."

"Yes, Mrs. Marlow," the polite young man said. That was a close one, Zack thought, as Mrs. Marlow went back into the house and he tucked himself away.

Matty giggled as he produced a Kleenex and cleaned most of the cum stains off Zack and then off the porch.

Zack couldn’t help himself. He pulled Matty to his lap and kissed him thoroughly one more time.

What’s happening to me, the confused, but happy lad asked himself as he walked home.

Since "that day," Zack and Matty hadn’t talked about what happened. It hadn’t seemed to bother Matty at all. He was sweet and friendly to Zack as ever.

Zack melted every time he saw Matty, all the while praying that no one would notice. Except Matty.

And every night, he would stroke himself to a ballbuster cum dreaming of Matty in his arms. In his fantasies, Matty would be wearing make-up and dressing like a girl – with lingerie and dresses. And big, high heels. What did that mean?

Zack was determined to find out.

 

Chapter Four – Matty’s Aunt and Uncle

Rob Muller had spent most of his life in torment. Strangely, it was what he feared most that freed him.

His wife Janice, who was Annette Marlow’s sister and Matty’s Aunt, was a very attractive woman, and when she paid attention to Rob that summer before their senior year in college, it seemed to Rob that he had found what he wanted.

That was partly true. Janice was a good and faithful wife, who gave him 16 good years of marriage and a fine son named Christopher, whom everyone called Chrissie. Chrissie was 15 and an honor-student, high-school sophomore in their town, which was 112 miles from Matty and Annette’s home.

Janice didn’t deserve what had happened to her six months earlier. It pained Rob to remember.

Janice and Chrissie were planning to spend a weekend at the state capital for Chrissie’s debate team finals and Rob would be staying home to do some things for his job.

As fate would have it, Janice and Chrissie left at 8 a.m. that Saturday morning, but half an hour out of town, Chrissie realized he had forgotten some papers he needed. A bit peeved, but supportive, Janice drove home, arriving shortly after 9 a.m. She told Chrissie to wait in the car, because she knew the boy would dawdle if he were to go looking for the stuff himself. Janice killed the engine and let herself in the front door.

That was when she heard what would change their lives forever.

Moans. Grunts. Squeals. Bed springs.

Her husband Rob, to whom she had been faithful forever, was upstairs fucking some bimbo! In their bed.

This is why the NRA is wrong about keeping a gun in the house, dear readers. Rob would be dead today if he had been a gun-boy.

Janice was nevertheless pissed. She had sharp nails and was about to dig them into some adulterers.

She strode up the stairs, flung open the bedroom door, and saw – Jack Bistro’s bare ass rising and falling as he fucked a woman beneath him – a woman with long, blonde hair, black stockings, very high heels, lots of make-up and a black nightie.

What was Jack, Rob’s best friend, doing with a woman in their bed?

Then she got a look at the "woman."

Oh, please no, she thought.

But it was what she feared.

Rob was in full femme apparel, taking his best friend’s cock into his tight bottom. The bottom Janice had fingered for him during hundreds of staggering blowjobs. The bottom she loved to watch as he walked around their bedroom. Her husband was a faggot! And so was his best friend.

Disgust consumed Janice and she began to retch onto her bedroom carpet.

That was when Rob and Jack noticed her. And almost became cardiac patients.

The terror of that moment gripped Rob every time he thought of it. Even after six months.

Janice’s fury was immense. After she finished throwing up, she attacked them both physically, scaring Jack half to death and making him grab his clothes and exit via the bedroom window, a twelve-foot drop to the ground.

Rob wasn’t so lucky. He was able to protect himself from the physical attack, but what followed was worse.

Janice pulled herself together and announced, "My son is in the car waiting and I must take him to his debate. We’ll deal with this when I return tomorrow evening." And she left.

Oh, no.

Rob truly had the weekend from hell.

He considered just packing and moving out. But he didn’t want to leave his son. And he still loved his wife, despite having consumed Jack’s cock and cum every chance they had had over the past ten years.

When Janice and Chrissie arrived at home, Janice put on a good show for Chrissie until the boy went to bed.

Then Janice addressed her husband. "I’ve had some time to consider what I now know to be true. Goodness knows what drove you to do what I saw you doing. I don’t want to know, nor do I want to know how long it’s been going on, or whether Jack is the only one whose cock you’ve been harboring. I also want no promises, sincere or otherwise, that you and Jack will be stopping."

<Gulp> "Then, what do you want?" Rob asked.

Janice fixed him with a "woman-scorned" stare. "I want two things. First, I want complete freedom to have sex with whichever men I want, whenever and wherever I want. Agreed?"

<Gulp. Gulp> A bitter pill. A babe like Janice would be very popular and Rob didn’t relish the role of cuckold. But what could he say under the circumstances? "Agreed," he said. "What’s the second thing you want?"

"I want you to help our son. He obviously takes after you. He’s been telling me for over a year now that he’s really a girl. Ironically, I’ve been telling him that he must keep that to himself because the news would destroy his father. I don’t want him marrying some woman, then sneaking around on her, ruining both of them. I want him to blossom as a sissy, then marry a nice man and settle down."

Oh, my. Rob sat to absorb all that. He nodded in agreement.

Janice went on. "In return, you can dress whenever and wherever you want, including in our home. You can’t sleep with me anymore, but you can bring any of your faggoty fuck partners in and let them screw your brains out, because mister, that’s what’s going to be happening to me in the next bedroom."

It was equally horrible and wonderful and had been such over the past six months.

Rob dressed full time, except when he was at work, and he was looking for a way to do at-home consulting so he could do 24/7 femme. He was getting hormone treatments, electrolysis, piercing, waxing, tucking and scraping. That made him very happy.

But the lack of sex made him very sad. Despite Janice’s pronouncement that Rob could host any men he wanted, right in their home, Rob was averse to doing that for at least three reasons.

Rob lay in his solitary bed, clad only in his black garter belt, stockings and six-inch mules, and reviewed the sad tally.

First, as far as Rob knew, Janice had not "entertained" once since her announcement of sexual liberation from their marriage. Rob was perplexed by this, and held out hope for a reconciliation. He certainly didn’t want to get Janice riled by bringing Jack over.

Second, Rob was embarrassed to do such things with his son’s knowledge. Rob had undertaken an intensive sissification process with Chrissie over the past six months, all with Janice’s approval, and the boy was a sissy angel. He was a feminine treasure who would drive men and boys insane with lust. But Rob thought Chrissie was far too young for such things, so he set a celibate example. And his sore balls and full bag were killing him.

Third, Rob’s lover Jack was so scared that Rob didn’t think that the darling man could even get an erection in Rob’s bed. Jack was terrified that Janice would "out" him and was giving Rob very wide berth. Rob longed for Jack’s tonguey kisses and gentle caresses. He longed for the taste of Jack’s cum as Rob slurped down load after load of manly cream. He longed for the feeling of Jack’s cock in his sissy bottom as Jack kissed him and spoke of his beauty. He missed the feeling of Jack on top of him, covering his lingerie-clad body with his masterful presence. The feeling of giving himself to Jack. Rob remembered as he touched himself down there and he was almost going to……

The door flung open.

Rob stopped stroking himself.

Janice stood there in all her feminine glory. She had made up her face to perfection. Her big titties were held in a demibra that showed her erect, huge nipples. Her towering heels accented her delicious legs, encased in silky, white stockings and held up by a satin garter belt. She wore no panties and her pussy hair was sopping with arousal.

Huh? Rob gulped.

"I’m horny as hell and I want YOU! Not some man I half know. I know you’re mostly only a man in your crotch, but we’ve shared a life and love and I want you!

Rob’s eyes filled with tears. He sissied over to his wife and enclosed her with his arms. They embraced and kissed hard. Geez. Rob came in huge sticky spurts all over Janice’s tummy. He squealed as he let go and Janice began to giggle.

"I guess I still excite you," she chuckled. "Now let’s get serious."

And they did. All night long.

 

Chapter Five – Matty’s Cousin

Chrissie Muller shared some of his cousin Matty’s appetites, but very little of his personality.

Chrissie loved his cousin, but thought him to be way too babyish. Matty was like a little kid or something. And what was he anyway? A boy or a girl? Chrissie knew exactly who he was.

Matty and Chrissie got together three or four times a year and they always got along, but weren’t really close.

Chrissie was close with three boys he had known most of his life. He couldn’t be much closer than sucking their cocks and taking them up his bottom.

Chrissie wasn’t gay and neither were the boys. Chrissie was a girl; of that he was sure. Chrissie insisted on being en femme when he made love with boys – from the very first time he swallowed Johhny Henry’s creamy load to the time Greg Grissom fucked him so hard he had trouble pooping for three days. "No girlie clothes, no pussy" was Chrissie’s policy and after unsuccessfully trying to get around the rule in school locker rooms and dark closets, Chrissie’s lovers knew that girlish attire and mood were prerequisites for the best sex any of them had ever conceived.

Chrissie didn’t do gang-bangs. It was one boy at a time, and the nicer they were to him, the more and better pussy they got. Had any of them dared to kiss and tell, they would have had to go back to manual relief or worse, to genetic girls. So they kept their mouths shut, to the point of not even being aware of each other.

Chrissie invited his lovers to make love to him. Chrissie spread his legs and opened his mouth. Chrissie ran the show. Not that Chrissie wanted to run the show. He would have loved a big, strong "Daddy" to dominate him and discipline him and take him to new erotic lands. For the moment, though, he was stuck with Johhny, Greg and Adam.

His own Daddy was a fairy crossdresser, not a real girl like Chrissy knew he was. From the very first time he swallowed Johhny Henry’s creamy load, he knew. Chrissie liked that his Dad was finally "out" but he thought less of him because it took 40 effing years for him to get up the moxie. Then Daddy only did so after he was caught with that "Jack" friend of his. To think that Chrissie had once dreamed of Jack making love to him. The prick deserted his father at the first sign of trouble.

Chrissie and his Dad had grown very close over the past six months. And Chrissie was amazed at how wonderful his Mom had been about Chrissie’s femminess. He was sad about Mom and Dad’s deteriorating relationship, but from the vigorous sounds of last night’s fucking, they appeared to have reconciled.

They were both beautiful, feminine people, just like Chrissie.

Daddy had taught Chrissie a lot about make-up and fashion and even about <blush> boys. Chrissie had no idea that his Daddy knew so much about girlie things and so much about relationships with boys. What Daddy didn’t know, but surely suspected, was that Chrissie was sexually active – really active – with his boyfriends nearly every afternoon.

After school the day before, Chrissie had invited Adam Casey to the house for some fun. Now that Chrissie was "out" at home, he was able to choose from a variety of sexy outfits, each openly displayed in his girlish room. Chrissie had just finished dolling up when Adam arrived at his appointed hour.

As usual, Adam’s eyes bugged out when he saw the femmed-up Chrissie, who was utterly scrumptious in pink lingerie and big heels. Chrissie liked Adam because Adam adored eating out Chrissie’s hot little pootie, which always made Chrissie squeal and cum at least twice before Adam got about the serious business of fucking.

Chrissie gave Adam the usual four-star fuck session, then kissed and licked Adam’s cock until the boy was hard and spewing in Chrissie’s pretty face.

Chrissie thought his life was just about perfect.

Lately, Daddy had been taking Chrissie all over town, both of them openly en femme, to buy lovely things and make admiring men’s cocks hard and dripping as they lusted after the lovely, femmy pair of tgirls.

Chrissie wanted Mom and Daddy to start referring to him by female pronouns, let him cease the public fiction of his "boyhood" and let him begin to live full time as a girl.

That was something he resolved to bring up that evening, but he was preempted. Big time.

Mom, Daddy and Chrissie always dressed for dinner – pretty frocks, stockings, heels. That night, Chrissie could tell something was up besides just Mom and Daddy’s reconciliation. So he asked, "What are you not telling me?"

Mom smiled at Chrissie, then at Daddy. Daddy had worn his prettiest dress that evening and had done his hair perfectly. Daddy said, "We’re moving, Honey. To a house only two blocks from your Aunt Annette and Cousin Matty. I’ll be getting a great new job, where they’ll know me as Lisa Muller. And you and I are going to be 24/7 girls!"

Huh? Chrissie thought the 24/7 part was wonderful. But being around his aunt and twitty cousin was a poor exchange for Johnny, Greg and Adam. He decided to bargain.

"Can I take hormones and get big breasts? Can I get my ears pierced? Can I be a blonde? Can you call me "she" and "her?" Can I have a Mercedes?"

Daddy giggled. "Yes, yes, yes, yes and you’ve got to be kidding."

Chrissie smiled in satisfaction. She guessed she would be able to find some boys just as good as Johnny, Greg and Adam in the hick burg where the Marlows lived.

There were always men if a sissy wanted them.

 

Chapter Six – Matty’s Principal

Gary Milford was a 45-year-old, attractive, single, well-liked, well-respected high-school principal, who would have continued to live the dull ache of a G-rated life if it hadn’t been for "that magazine."

One day nearly two years earlier, Gary was at his favorite newsstand, looking over the educational journals, when fate grabbed him by the nuts and twisted hard. Mixed in with the painfully dull professional material was a misfiled copy of "Panty Boy" magazine. Like all men, Gary had heard about that piece of wretched, pornographic, trashy filth, but had never held one in his hands. Until that moment. At that time. Then.

He looked at the cover and his ears heated up. The logo was filthy in itself, with a pair of pink panties draped over the capital "P" in the title. Then, drawn to the flame, Gary saw the picture of the cover "girl." Someone named Gloria. A boy named Gloria. Imagine that. With make-up and big, red, painted lips. Parted for a kiss. Ohhh.

Poor Gary’s size-32, white, Jockey briefs had never been so crowded. It must have been fate, he thought. He was supposed to buy the magazine. He grabbed up his copies of "Nerdy Principal" and "Education Geek," and paid for all three magazines.

When he got home to his one-bedroom condo, Gary asked himself what the heck he was doing. He stripped naked, found the Vaseline in his bathroom, lay on his bed, applied three big, oily dollops of Vaseline to his large, thick, but mostly unused cock and ripped the plastic cover from the Panty Boy magazine.

He held the magazine in his left hand as he rubbed slick comfort onto his enflamed cockhead. In the first pictures, "Gloria" was a boy who stripped naked, then rebuilt himself into a staggeringly beautiful, made-up, stockinged, lingeried angel. The picture story was huge and each picture brought poor Gary closer to doing "that bad thing" all over himself. The last ten pictures in the series were his downfall.

Gloria was looking into the camera as she stroked her tiny, but beautiful cock and gorgeous little balls. The caption said, "Make me cum, Daddy. I want to cum for you!"

Oh, it was incredible. Then he turned the page and the boyish/girlish masterpiece was in the full agony of a stunning orgasm. Thick spurts of sissy cream were gushing from that itsy-bitsy cock, one-third the size of Gary’s rammer. Gary had never seen anything half as sexy in his life. The poor man arched his back and actually cried out as his guts attacked him. His balls evacuated with a wrenching motion and he must have produced a quart of thick cum. He may even have passed out.

Gary’s life after that was one of joy and torment. The joy came from finally knowing who he was and what he wanted and from acquiring a complete set of a magazine that had him cumming at least four times each day. The torment came from the notion that he would probably never share bed and joy with a real panty boy.

Gary was quite wrong about that notion, but for two years, he was right. Worse, he found himself looking at sissyish boys in his school, wondering if they were panty boys. Not gay. He thought that was disgusting. He wanted girlish boys. Boys who wanted to be girls and have a strong man to guide them. And discipline them, using humiliation if he must. And to fuck their little bottoms until they squealed and screamed with joy.

Some of the boys he saw, and they weren’t always sissyish, stirred his testicles. Were they sissies? Did Gary have the power to recognize a sissy from a pack of normal-looking boys? Of course not. And what was that strange attraction he had to that Mrs. Louis? A fine teacher and a beautiful woman, not a sissy. Why did she, a mid-20s, married woman, harden Gary’s big sissypleaser?

Another puzzler.

Of course, dreaming of something and acting on it are very different things.

But cosmic forces were moving in the right directions to make Gary’s dreams come true. And lots of other people’s as well.

 

Chapter Seven –Matty

Matty Marlow had a great outlook on life. When males acted like jerks to him, he forgave them.

The males were just following instinct. When a woman comes across something she doesn’t understand, she tries to "join" with it. When a man faces something he doesn’t understand, he tries to kill it.

Matty was unclear about a lot of things in his life, but he was certain of three things. One – he loved, respected and practically worshiped his mother. Two – he passionately, romantically and erotically loved his friend Zack and would marry him someday. Three – he loved being who he was, even if he didn’t fit any conventional pattern.

Some called him a "faggot." His mother told him that a faggot was a mean thing mean people said to nice people. Matty wasn’t stupid. He knew a faggot was a mean name for a male who had sex with other males.

Like the fun he had had with Zack on the porch that night last month. Matty loved what happened that night. He loved Zack and he loved that Zack was beginning to express his physical love for Matty. Matty knew that Zack was a wonderful boy and he and Zack would fall in love and live happily ever after.

Matty also knew that Zack wasn’t one of those "faggots." And neither was Matty. Matty was something or someone that even he couldn’t define yet. But Matty knew who he was.

Matty knew that he thought a lot about being in bed naked with Zack. Touching his beautiful body. Kissing him. Rubbing against him. Taking Zack’s perfect, hard cock into his mouth. Swirling his tongue all around the head. Making Zack pant and groan and make that creamy stuff into Matty’s soft, wet mouth.

Matty knew that the creamy stuff was "cum’ and that boys made it when they got excited, then got that wonderful feeling.

Matty loved that feeling, especially that night when Zack gave it to him.

Matty knew that cumming with someone you love and making that someone cum are the two greatest feelings in the world.

He was pretty wise.

Matty and his Mom had always shared their experiences. Always. So, of course, after that wonderful night of kissing and cumming with Zack, he told Mommy all about it.

Annette was interested but not surprised. And she was very pleased. Zack was the sweetest, nicest boy, except for Matty, that Annette had ever met.

Her little boy was growing up. Falling in love and cumming his little balls dry.

The afternoon after his wonderful night with Zack, Matty was having his "snack" at Mommy’s breasts, when Annette introduced something extra nice and extra intimate. As her sweet boy suckled Annette’s right breast, she said, "Pull your pants down, Matty. And your underpants."

As always, Matty obeyed Mommy without question. The little angel was sucking his mother’s breast gently and was completely exposed below the waist. He wasn’t scared or worried. Completely submissive to his mother, Matty was expecting something good.

And he was right.

As Matty nursed at his mother’s breasts, Annette reached down and began to stroke her son’s genitals. Expertly.

Matty wiggled with pleasure.

"Sweetie," Annette said, "You’re growing up now. Boys your age need to be milked. Frequently. Like Zack did for you last night. Does this feel good?"

Matty sucked harder and shuddered in impending ecstasy. Annette was an EXCELLENT milker. Before long, Matty’s pretty face scrunched up, he squealed, and began to spurt globs of his hot cream all over his mother’s hand.

Annette hugged Matty, wiped her hand with a towel, and kissed her son lovingly.

From then on, a nice milking was part of their daily nursing session.

Instead of cooling Matty off, it seemed to heat him up. And want Zack more. But Matty was still a patient boy.

About a week after Matty and Zack’s cummy encounter, Matty discovered something different when he went to bed.

Mommy always laid out his pajamas when he went to brush his teeth and wash his face and hands before bed. That night, when he returned to his room from the bathroom, a pretty, yellow, cotton nightie was on the bed instead of his boy’s sleepwear. He looked at the nightie, then at his adored mother.

"I think you’ll find this more comfortable, Sweetheart," Annette said.

"Thank you, Mommy," Matty said. Then he stripped naked and slid the nightie over his head.

"You look adorable," Annette said.

Matty considered himself in the mirror and agreed. He was adorable.

Matty got on his knees and said his prayers. Then he hopped into bed. His mother tucked him in and kissed him. "Thank you for the nightgown, Mommy. I love it. And I love you."

Annette beamed. How could anyone not love this child, she thought,

When Annette turned off the light and left the room, Matty’s head was filled with conjecture.

Why did he look so good in the nightgown? A girl’s nightgown. What would Zack think if he saw Matty in the nightie?

Matty drifted off to sleep and began to dream.

Matty dreamed that he was asleep in his bed in his pretty nightie. He dreamed that he awoke to a room filled with morning light. He looked at himself and was pleased to see that he had a pretty set of cute, but tiny titties, with puffy little nipples. He still had his boy’s privates, though. Wasn’t that odd?

He looked at the door and Zack was standing in the doorway, naked and hungry for Matty. Matty liked the dream already.
"You’re the sweetest, prettiest girl in the world, Matty," Dream Zack said. "You’re my very own princess and I love you with all my heart."

In real life, Matty’s little cock was very stiff.

Dream Zack pulled back Matty’s sheets and looked at Matty’s privates, which were exposed because his nightgown had ridden up.

Zack got into bed with Matty and surprised Matty by kissing and licking Matty’s cock. Then he began to swirl his tongue all around Dream Matty’s balls and the real Matty’s teeny cock exploded, spurting six creamy glops all over Matty’s sheets and new nightie.

There was something very exciting to Matty about dressing in a nightie. One’s balls often admit what one’s intellect will not.

Over the next three weeks, Matty wore three pretty nighties his mother had purchased for him and he blew cum into every one he wore, every night. His dreams of sex and love with Zack grew more vivid, draining Matty’s balls vigorously and thoroughly, while re-assuring Matty that his dreams would come true.

If Annette could help Matty achieve those dreams, she was willing to do whatever it took.

 

Chapter Eight – Testing, testing

Early the next day, Stephanie Louis called Annette and asked if they could confer about Matty. They made an appointment for that afternoon after school and got together in Stephanie’s empty classroom.

Annette was a little uncomfortable about having Matty wait for his afternoon snack of breast milk, but Stephanie had stressed the meeting’s urgency.

"Mrs. Marlow, first, let me say that it has been a pleasure to be Matty’s teacher. He’s the sweetest, nicest teenager I have ever met and I’m honored to meet the woman who helped make him that way.’

Annette smiled. That was a great way to begin.

Stephanie continued. "I’d like to give Matty a battery of tests called the Gingerman Test."

Annette had never heard of that. "What would be the purpose?"

"It considers gender orientation and tells us where the test-taker fits regarding gender."

Annettte bristled a bit at that. "I think I know my boy, Mrs. Louis. Why should he take such a test?"

Stephanie was losing Annette, so she got personal. "I know the pain of gender misplacement, Mrs. Marlow. I’m trying to save Matty that pain. It’s only a test. He won’t even know what it’s for and you don’t have to do anything once you get the results. But if you do, I can help you."

Annette asked, "How would you know such things, Mrs. Louis?"

Stephanie hesitated. It wasn’t something she wanted known, but Matty’s happiness was at stake. "I began life as a boy, Mrs. Marlow – 14 years worth. Changing to my real gender saved my life."

Annette considered Stephanie, then said, "You’re a very brave and kind woman to tell me that, Mrs. Louis. I’ll keep your confidence and have Matty take the test." Then she got up and gave Stephanie a huge, grateful hug.

Some days it’s worth being a teacher, Annette thought.

Two days later, after Matty had taken the Gingerman Test and Stephanie evaluated the results, Annette returned to confer with Stephanie.

"So?" Annette asked.

"Matty’s off the charts, Mrs. Marlow. They’ll have to change the scale. He’s the most feminine boy ever tested. And also one of the kindest, sweetest and most innocent. It’s a miracle he’s still alive in this world of sharks and charlatans. Again, it’s a great tribute to you, Mrs. Marlow."

Annette wasn’t surprised at all. She knew Matty. But she was, and this was very rare for Annette, stumped as to what to do about it.

"I would appreciate your advice and counsel, Mrs. Louis," Annette said.

Stephanie smiled. "Let me tell you my own story."

"I guess it all started when I was about seven. I wasn’t an unhappy little boy, but I didn’t know how happy I was supposed to be. My mother was a very beautiful, feminine woman, who enjoyed dressing as a woman. She took her time and care with her make-up and her dress. She wasn’t very modest, and would often leave the door open when she was at her vanity. Mother would sit on the stool, wearing only her panties, bra, garter belt, stockings and big heels as she brushed her beautiful hair and painted her lovely features. I would watch her and didn’t hide my interest.

"I remember asking Mom one day, ‘Mommy, how old do I have to be before I wear make-up and pretty things like you?’

"Mom smiled, but didn’t ridicule me. ‘I don’t know about that, pumpkin. Most boys don’t dress like me.’

"I was hardly discouraged. ‘I’m not like most boys, Mommy.’

"Mom’s sweet laugh tinkled. She was definitely laughing WITH me. She hugged me and gave me a big hug and kiss. She smelled wonderful. I wanted to smell like that.

"Daddy would have been very upset if he had heard that conversation. So we didn’t tell him.

"When I was ten, Mom bought me my first panties. She watched me hold them against my skin, then tremble as I eased them up my legs and across my little cock and balls. I was hard as nails and blushing with shame from letting Mom see me like that. But I loved those panties!

"Mom bought me pretty nighties and other panties, but we hid them from Daddy. When I was thirteen, Mom bought me my first stockings. I remember they were tan and sheer and heavenly. But so embarrassing! I was shuddering with pleasure when I snapped my satin garter belt to my stockings. Then, <blush> I started to cum. Right in front of my mother. Big, sticky spurts. The first cum of my life. And the most humiliating.

"I adored my stockings and the sexy way my legs looked in them. And I loved cumming, even though I wished my mother wasn’t watching. Her reaction was not what I expected.

"’It’s about time you made sissy cream, Sweetheart. I was wondering when your girlish feelings would make you spurt and squeal. Oh, I can’t wait to dress you in pretty things and watch all your sissy excitement jump from your little sissycock.’

"Well. That was good, I thought. Wasn’t it? ‘What about Daddy?’ I asked.

"’ I give Daddy everything he wants, Baby. He’ll do what I want. Everything I want.’

"Mama was right about Daddy. She tuned up the sex dial on their lovelife and all he could think about was Mama’s charms. She must have told him about my feminine side during one of Daddy’s weak moments. Around Mama, he had several of those. I was so nervous the first time I dressed as Stephanie around Daddy, but he glowed with love for me and accepted me as his daughter from the first moment.

"I still wasn’t ready to go to school as Stephanie. But I had a much higher priority anyway. Winning the heart of one Blake Louis. Blake was two years older than me, the dishiest boy on the planet and, I thought, already totally in love with me, although it scared the living poopie out of him to be in love with someone he thought was a boy.

"Blake was always hanging around our house. He helped Dad clean our pool and work in the yard and all. But he was too shy to make a move on me, because of that gay phobia stuff. I decided to see how a little shock therapy worked.

"One Saturday when Blake’s parents were away for the weekend, Mama asked Blake over for dinner and a sleepover. He accepted eagerly, bringing the videos we asked him to under the pretext that since he and I were boys, we would watch car chase movies all night. When Blake showed up, I was upstairs. Mama and Daddy knew him very well, so they chatted easily.

"Mama yelled upstairs to me that Blake had arrived. Five minutes later, I walked downstairs to join the group.

"Mama and Daddy greeted me as if everything were normal. Blake was in shock. I guess it was because I was wearing full make-up, a purple, ribbed top, 13-inch miniskirt, silky, black stockings and four-inch stiletto sandals. I was gorgeous, though I wished my hair had been longer.

"Blake was speechless. I guess he was especially surprised because Mama and Daddy were acting so normal about me being a girl. They were calling me ‘Stephanie’ and ‘Honey.’

"I walked over to Blake and gave him a little welcome kiss on the his cheek. And I smiled when I saw his crotch swell <giggle>. It took a little while for Blake to get his bearings in the situation, but by the time dinner was ready, he held my chair, passed me everything I glanced at, and called me ‘Stephanie.’

"After dinner, we all did the dishes. Then Mama and Daddy went to bed for their usual 12 hours of sleep mixed with pounding sex. That left Blake and me to our own devices.

"Blake wanted to ask me all about what was happening with the girlish clothes, not that there was anything wrong with it. But I just asked if we could watch those movies he brought. Befuddled, but very aroused, Blake set up ‘Hot Rod Hell’ on the VCR, then sat on the opposite end of the couch from me. I remedied that by getting up and sissying over to his side of the couch, then plopping my soft, sexy body next to his. I snuggled next to him, putting my head on his shoulder. The poor boy was shuddering with excitement and fear, but he put his arm around me right after the opening credits of the movie. His poor crotch was all lumpy, so I did what instinct told me to do. I put my soft hand on his crotch and rubbed gently.

"Blake groaned. Then he looked in my eyes, seeing a girl’s love, and he made the biggest and best leap of his life. He kissed me. Very well. And very passionately. And for a very long time. Long enough for me to free his cock from its confinement and administer the first handjob of my life as we kissed. As Blake’s thick, rich nut juice spurted from his cock, I knew he was mine.

"Oh, Mrs. Marlow, I’m so sorry," Stephanie said. "I’ve been far too explicit. I don’t know what came over me. I guess I just thought being Matty’s mother, you would understand. I’m so flushed too. Is it warm in here?"

Annette Marlow shared Stephanie’s feelings about the heat. "That’s a very exciting story, Mrs. Louis. I don’t mind hearing it. And I must say, it excites me too. I just have a couple of questions. Do you still have your….umm….male things?"

Stephanie smiled. She liked this woman. "Yes I do. And they still work very well. What was the other question?"

Annette gulped. "Do you like women…that way?"

Stephanie connected the dots. "I adore nice women. Especially if they’re as attractive as you, Mrs. Marlow."

Their eyes locked. Annette thought idly, too bad I won’t hear the rest of that story. Then she removed her blouse and unhooked her bra, showing Stephanie her wet, dripping nipples and large, milk-gorged titties. Stephanie gasped. Then, without a word, she began to drain each jug, taking small, baby sips. Annette orgasmed halfway through the second tit-full, from the sheer intimacy and dirtiness of the situation.

Then each lovely woman stripped to her lingerie. Annette peeled Stephanie’s panties down, shuddering with pleasure as she held her first shemale cock and the first cock of any variety that she had held since her husband left.

The ladies kissed with whimpering ardor. Annette’s pussy was drenched, so it made no resistance as Annette grabbed Stephanie’s clitty and inserted the head into its moist folds. Stephanie pushed and began to fuck Annette with a slow motion. In college, Stephanie could have fucked every girl in her sorority. Wait a minute, she did fuck every girl in her sorority. And in neighboring sororities. A she-male stirred sexual feelings in those girls they could barely understand, but wanted desperately. But she hadn’t fucked a woman, or another man, since she and Blake were married.

Annette was a great piece of ass. Tight. Hot. Needy. Loving. And great boobs. Best of all, Annette was a good person and very appreciative of Stephanie’s attentions.

Stephanie fucked Annette through multiple orgasm on multiple orgasm, made a big, messy cum of her own, then licked up all of Annette’s juicy juices. When Annette was able to stop screaming, she took Stephanie’s shemale weapon between her red lips and sucked her very lewdly, making Stephanie slick and hard and wondering how she would explain to Blake that evening about the reduced creaminess of the tasty loads he would swallow. But a stiff cock thinks only of the moment. And the hot ass Annette was wiggling at Stephanie, begging for an anal consummation of their new friendship.

Stephanie drooled with lust as she put her pink cockhead at Annette’s back door. "Are you sure, Mrs. Marlow?" she asked.

Annette could only groan and wiggle her bottom in lusty invitation.

Taking that as a yes, Stephanie pushed her girlish cock into Annette’s hot, extraordinarily tight ass.

Annette screamed and came yet again. This show of appreciation enflamed Stephanie, causing her to give Annette the ass-fucking of her dreams. Actually, the first ass-fucking of Annette’s 37-year-old life. But not the last.

No. Not the last.

As Stephanie’s knees buckled, gut clutched and balls emptied into Annette’s needy bowels, Stephanie knew that Blake would be tolerant of Stephanie’s little indiscretion. Especially when she told him about her plans for Blake and Matty.

Stephanie was certain Blake would want to be part of that.

 

Chapter Nine – The Muller Ladies

Janice. Lisa, and Chrissie Muller arrived in the Marlow’s town three days before Thanksgiving, exactly one month after Lisa, the family’s Dad, announced the big changes in their lives.

As their movers toted couches and refrigerators across the lawn and through the door, nosy neighbors speculated about the family structure represented by two sensationally attractive grown women and a tartily dressed, sexy, little teen babe whose skirt was too short and heels far too high.

Moving was exhausting and for three days the Muller parents worked hard to put things in order while Chrissie enrolled and began to attend the high school at which Gary Milford was principal and Matty Muller a cute little freshman.

Chrissie was, as ever, extraordinarily hot to trot, flirting with every cute boy in sight in a sincere effort to gain a "reputation."

She was so busy wiggling her bottom in front of a whole new legion of boys, that she didn’t even cross paths with her cousin Matty. No problem. They were scheduled to spend Thanksgiving together at Matty’s house.

On Turkey day, the Muller ladies showed up with lovely dresses, perfumed, powdered bodies, smiles, hugs, yams and creamed onions.

Kisses all around with an admiring Annette. Janice had told her sister all about her husband’s 24/7 femininity, a pleasure also enjoyed by her son Chrissie.

"Lisa and Chrissie, you’re lovely!" Annette said. And she meant it.

Janice asked, "Where’s Matty?"

"Just a moment," Annette said. Then she called up the stairs, "Matty. Everyone’s here!"

"OK, Mommy," Matty called.

Seconds later, the room blazed with beauty as a delicious vision of feminine loveliness descended the staircase.

The Muller ladies gasped.

Matty Marlow was wearing a long-sleeved, lacy white dress. His stockings were silky white. He walked easily in four-inch-stiletto, strappy white sandals. His hair was short, but girlishly styled. His lips were skillfully glossed and begged for a man’s soft kisses. Her eyes were mascaraed, lined and shadowed to feminine perfection.

Chrissie and Lisa sprouted serious woodies. Matty Marlow was a major dish!

Janice regained her wits first. She stepped quickly to Matty and hugged him.

"Matty, you’re an angel."

Matty beamed with pride.

Janice turned playful. She lifted Matty’s skirts and felt his bulging erection. "What’s this hiding in a pretty girl’s panties? Is that supposed to be there?"

Matty giggled as Janice stroked him playfully. Then she pulled his little popsy from his panties and gave it some very nice strokes. "Your mother said she’s been milking you, but sissies in femmy things need to be milked often. You’re very excited, aren’t you, Sweetheart?"

Matty nodded, gasping a little. "Yes, Auntie," he said. "That’s very nice."

Janice persisted in her strokes, and said, "Annette, you need to have this pretty girl milked by a man, or at least a boy, and often. Her boyish goo has to come out of her so she can flourish as a girl. Plus, a sissy in pretty things is always on the edge of orgasm, right, Matty?"

Matty panted, made a girlish little squeal and began to spurt sticky cream from his tiny tickler. Chrissie, who was horribly excited, groaned and filled her panties with sweet goo. Lisa had a bit more control, but only a bit. She began to think about a good, hard fucking from a man (but not that coward Jack), something she missed terribly. Then she filled her panties with a copious cum as well.

"We go through a lot of panties in our house, Annette," Janice giggled. She held up a small shopping bag and said, "I always carry several extra pairs for both of them. Chrissie, as he finally admitted to us, has for some time had quite the lovelife as a girl. And you know about my ‘husband’"

Annette said, "We’re transitioning Matty. He’s not 24/7 yet, but I’ve been getting excellent advice from a teacher of his who is a lovely, married shemale. Her husband has volunteered to ‘assist’ Matty with some areas only a man can teach him."

Matty blushed. He had met Mr. Louis last week. Mr. Louis was very sweet and very handsome. But he was married and Matty loved Zack. Mommy said that Mr. Louis could teach Matty some things that would help Matty with Zack. Girl and boy things. Sex things. Matty liked sex things and Mr. Louis was practically drooling over Matty.

Matty loved when men and boys admired his feminine beauty and wanted to cum with, for, in and on Matty.

If Mommy thought "lessons" with Mr. Louis were a good idea, then they surely were. But for the moment, he had to deal with the fact that his sissy uncle and cousin had just creamed their panties because of him.

The five lovely people had a wonderful Thanksgiving dinner. When everything was cleaned up, Mommy suggested that Matty show cousin Chrissie his room.

The little sweethearts held hands as they walked up the stairs in their very high heels. "I love high heels, don’t you, Matty?" Chrissie said. "They make me feel so girlie and the men’s tongues hang out when they see our legs and protruding bottoms."

Matty blushed. "I’m still getting used to them and I haven’t been outside dressed as a girl yet."

The idea of walking en femme, in big heels, in a public place had Matty’s teenie weenie all hard again. Chrissie noticed. And she was most randy about it.

"You know, Sweetie," Chrissie said, "Your Mom was right about that milking thing. Girls like us can’t walk around with too much ball juice in us. It hurts us and makes us less feminine."

Matty was trusting, but wary with his "fast" cousin. "How do you get rid of your cummies, Chrissie?"

Chrissie said, "In our last town, I had three boyfriends who gave me everything I needed and I gave them back double."

Matty had no idea. His little thingee was stiffer and throbbing visibly.

Chrissie said, "I see you’re in pain, Honey. Let Chrissie help. Let’s just ease those panties over your stiffie and down to your knees. Stand just like that and I’ll get on my knees."

Chrissie admired Matty’s cock and balls at a distance of three inches. Matty’s package was the smallest one she had seen. And the girliest. But some sissies can produce a lot of thick, sticky cum, regardless of their equipment size. Chrissie looked up at Matty, who was holding his skirts up and watching Chrissie with great interest. Matty whimpered a little with real need.

Chrissie kissed the velvet head of Matty’s little tickler and Matty squealed sweetly. Chrissie was a great cocksucker and she was delighted to be able to show her pretty cousin a good time. She had never kissed a sissy cock before and she was fascinated at how different the whole experience was. With a boy, she had some hope, though never realized, that the boy would dominate her, ruling her sexually and making her give herself to him completely. With her cousin Matty, she knew no such thing would happen. But that was OK. She loved giving her nerdy, but beautiful cousin pleasure.

Matty certainly appeared to be enjoying Chrissie’s girlish kisses on his cock. Matty was erect and wiggling, barely able to stand on his high heels. Matty was a pretty sight. His stockings accented his long, delicious legs. His garters and sinking panties added to the general naughtiness of the scene.

Matty knew he shouldn’t be letting his cousin lick and suck his stiffie like that, but Mommy hadn’t forbidden it and it felt very good. Matty was pretending that Zack was on his knees licking Matty’s balls the way Chrissie was. Oh, Zack, your tongue on my tee-tees feels wonderful, Matty thought. Zack would be manly and forceful, Matty knew. Zack would show Matty heaven, Matty was sure of that. Just like the gates of that wonderful place that Matty and Zack glimpsed that night on the porch.

But Chrissie was sure doing exciting things, even though she wasn’t Zack. Poor Matty was stiff and excited all the time since Mommy started dressing him whenever he was home. What if Zack walked in one day and saw Matty in pretty frillies. Matty was sure that poor Zack would be very excited. Maybe Matty would have to do to Zack what Chrissie was doing to Matty. So nicely. Swirling her tongue around Matty’s tinkler head. Ohhhhhhh, Chrissie. Ohhhhhhhh, Zack.

Matty shuddered, squealed prettily and began to helplessly spurt glob after sticky glob of his sweet nectar onto Chrissie’s pretty face. Ohhhhh, it was wonderful and Matty knew that it would be even better with the boy he loved.

As Hannibal Lector said, "Quid pro quo, Clarisse." It appeared that Chrissie expected a good clitty-licking from her pretty cousin as well. Matty was all for it, although he wasn’t sure about technique. Chrissie’s throbber was so hot, all Matty would have to do would be breathe on her peehole and Chrissie would make a big, cummy mess.

Matty removed his dress, to avoid stains, he said, and Chrissie followed suit. Chrissie was just beginning to get some definition to her titties, maybe an A-minus-minus cup. Daddy was giving her some powerful hormone treatments, and her boobies showed real promise of substantial growth later.

Chrissie noticed that Matty’s lacy bra was covering a flat chest, but his nipples were puffy and looked very tempting to Chrissie. Chrissie had never sucked titty, but Matty was the world’s leading expert.

The cousins lay on their backs, next to each other, on Matty’s bed. Matty took the initiative by kissing Chrissie, as he rubbed her tummy with his soft, girlish hand. Chrissie was painfully excited already and made little gasps of pleasure. When Matty reached into Chrissie’s satin panties and pulled out her substantial cock and balls, it was Matty’s turn to gasp. Chrissie adored the feel of Matty’s lovely hand on her cock and was expecting Matty’s lips on her tickler at any moment. What happened was even better.

Matty pushed up Chrissie’s bra and began to kiss, lick, suck and even <gasp> bite Chrissie’s sensitive, developing nipples. Matty continued to massage Chrissie’s hair-trigger cockhead and in a few agonizingly erotic moments, pleasure slammed into Chrissie and her cock exploded with her cream.

Holy beginner’s luck, Batman, Chrissie thought. Either that, or we have a natural here. My cousin is turning into the ultimate sissy. A feminine treasure who will stiffen cocks in a three-mile radius and cause empires to rise and fall.

Surprisingly, Chrissie wasn’t jealous. She just wanted a share of the wonder that was Matty.

Anyone who ever calls this one "he" or "him" again is batty, Chrissie thought. So we won’t either.

Matty was delighted that she had made her cousin and friend cum like a nuclear explosion. Somehow, she had a sense of her gift. It was something she would be sure to share with the world.

But especially Zack.

Lots more would have probably happened, but Lisa, Chrissie’s Daddy, called upstairs to announce that the Mullers were going home.

Matty always obeyed Mommy’s orders instantly, but since it was only Uncle Rob or Aunt Lisa or whoever-the-heck that was, the little doll delayed obedience just long enough to lick all the gooey cum from Chrissie’s privates, including her <blush> balls. It was so intimate and so achingly erotic that Chrissie ended up gasping and cumming all over again. Prudently, Matty capped Chrissie’s popsy with her mouth and swallowed her big load neatly.

I just have to arrange a sleepover, the panting Chrissie thought. Or maybe I’ll just move in with Matty and make love to her all the times that there are no boys around.

Too bad, though. The little sweetheart party was over and the girls had to get dressed.

As the Marlows bade the Mullers goodbye at the front door, Chrissie also thought, that sissy will be a force of nature when she’s released on the world.

 

Chapter Ten – Pleasant Detention

Though Matty Marlow was as demure and sweet a sissy as you would meet, her cousin Chrissie was a flirty little cockhound.

By the second week after Thanksgiving, Chrissie had a well-earned "reputation" around school as a skilled and willing cockpleaser. She hadn’t given her big secret away yet, but her cocksucking skills had brightened the day of several hunky boys. Unfortunately, one late afternoon in the third-floor janitor’s closet, as Andy Donavan was groaning loudly and spurting his creamy essence into a kneeling Chrissie’s lovely face, they were busted by Principal Gary Milford.

Gary had heard rumors about the new, big-city freshman girl, but that wasn’t why he followed her that day. He was getting the same kinds of feelings from Chrissie that he got in the presence of Stephanie Louis. How odd!

Regardless, girls can’t just give blowjobs on school property whenever they get cum-hungry. There are rules. To be followed. And enforced.

When Gary burst in the door, Andy, of course, finished his cum. No guy interrupts a cum. No matter who catches him. Even if the building is burning down. The odd part was that Andy was shameful and scared, but Chrissie, despite being caught in the act, continued slowly polishing Andy’s velvet knob with her tongue until he was thoroughly cleaned.

Sissies have standards.

And she didn’t appear to be the least bit scared or upset.

Andy picked up his pants and panicked, pushing past Gary and running out the door and out of the school.

No matter, Gary thought. I’ll deal with him later.

Truth was, Gary was wildly excited to be alone with this cum-faced, defiant girl who was making his sissy-sense tingle.

"Follow me, Miss Muller," Gary said. "We’re going to my office."

"Yes sir," Chrissie said.

Gary handed Chrissie a handkerchief and asked that she clean her face. She did so, slowly, carefully and in a teasing way that made poor Gary hard and needy.

Silently praying that he would not cum and humiliate himself, Gary marched the offender to his office.

Chrissie was wearing five-inch heels and stockings, Gary noticed. And noticed some more. She had a short skirt and great legs. And a great ass that wiggled as she walked. The other girls dressed for "comfort," which meant they looked like the boys. Chrissie must be a panty boy, Gary speculated and fondly hoped.

It was late in the afternoon and it appeared that Gary and Chrissie were the only people in school. Matty had been home for an hour, had had his afternoon nursing and milking, and had changed into girlish gear. But Chrissie had stayed at school to suck cock. And now she was about to be punished for it.

Punished.

Chrissie wanted that big, strong man to punish her. She liked boys, but oh – the pleasures of a man.

Mr. Milford was a sissy lover too. Chrissie was sure of that. She noticed his hardon when she was licking the goo from that coward Andy’s cock. Mr. Milford appeared to have a fine package between his legs.

Scratch that Andy off the list, she thought. He had no guts.

Mr. Milford hasn’t taken his eyes off my bottom once, she thought. This will be too easy.

The pair entered the principal’s office and closed the door.

Chrissie seized the initiative. "I know I was bad, Mr. Milford. Are you going to punish me?"

Gary gulped. This was all new to him.

"Of course you’ll be punished, young lady. And I’m telling your parents. What you did was disgusting."

Chrissie looked down and acted sorrowful.

Then she said, "You’re right. You should spank me. Bare bottom. I deserve it."

Poor Gary’s woodie grew even bigger. And his balls ached with need.

Gary began to say, "We don’t have corporal punishment in this school district. You and Mr. Donavan will be suspended." But all he managed to say was, "We don’t…."

Chrissie had dropped her panties and freed her substantial cock and balls to Gary’s needy eyes. It was a dream come true for him. "Panty Boy" come to life. And, perhaps, the worst thing that ever happened to him. Or the best.

Gary sat to hide his hardon and to get his wits about him. Chrissie sissied over to him and laid herself across his knees, bottom up, skirt pulled up to reveal two plump, perfect, pink, rectal globes and the hint of a scrotum peeking between her stockinged thighs.

No man can fight something like that. It isn’t fair. If it’s your dream and you don’t act on it, you should just jump into a hole and pull the dirt over yourself.

 

Gary sighed and did what he had to do. He rubbed Chrissie’s bare bottom with his hand and said, "You shouldn’t be going those naughty things in school, Miss Muller. Shouldn’t be."

Chrissie’s cock stiffened as Gary caressed her pert bottom. "I know, sir. I deserve a spanking. And whatever else you give me."

Gary felt Chrissie’s clitty rubbing against his thigh. He clamped his knees together to hold her throbber in his thighs’ embrace. Oh, my. She was rubbing her cock between his thighs. Gary raised his hand to spank the little panty boy then SMACKED it down on her right bottom cheek. Chrissie cried out, then moaned, "I’m so naughty. Spank me, you big strong man!"

Gary’s lust was fired. He raised his hand and spanked the she-teen’s left cheek, then alternated swats, gaining fury as Chrissie’s cries became moans of lust. Finally, with a loud squeal, Chrissie emptied her balls all over the frantic man’s thighs. She shook. She cried real tears. She whimpered as Gary wondered if they needed any disgraced school principals in Greenland.

Chrissie turned her pretty head to look at Gary, locking eyes with the terrified man. Showing him a girl with a woman’s needs and a boy’s sex drive. A girl who needed him.

Caution got up and left the room quietly.

Chrissie stood in her big heels, rubbing her red bottom and her tearful eyes. Her pricklet was dripping cum.

Gary trembled and thought, "I’m ruined. This girl’s parents will be hanging me by my balls. I have to make amends."

Gary said, "I’m sorry if I hurt you Miss Muller, but those naughty things you were doing, they…."

Chrissie sobbed softly. Gary stood up, walked over to her and stood facing her. In her heels, she was almost as tall as he. She tilted her head upward and parted her red lips. Gary hesitated a micro second, then engulfed her with his arms and pressed his famished lips to hers.

They kissed with animal need. Wetly. Toungily. Completely.

Chrissie grabbed Gary’s pants at the beltline and pulled them and his underpants over his hips and down to his ankles. Gary’s cock was hugely erect. His balls dangled, full and achy.

Chrissie gasped when she saw them. She smiled at Gary, then fell to her knees and took his cockhead into her slurping mouth.

There was no explaining now. No quibbling. No way out. Only straight ahead.

Gary had wanted the loving caresses of a panty boy and now a pretty one was sucking his ready-to-burst cock.

He decided to enjoy it.

So did Chrissie. She had never had a man before and she wanted all of him, beginning with a bellyful of his hot cum. She uncapped his steaming cock and took a moment to lick his large, beautiful ball sack. It was dark and hairy. Chrissie could almost taste the cum she knew was on the other side of that wrinkled flesh. She decided to sample the flavor, so she resumed long, wet tongue swirls around his apple-sized cockhead. Chrissie began to wonder if her tiny bottom would be able to accept that monster. She decided to find out or die trying.

Gary was groaning with lust and shaking with fear for his future. As Chrissie’s soft, warm hand caressed his nuts and her red lips and tongue adored his cock, Gary gave himself over to the greatest pleasure of his life. He opened his mouth to warn Chrissie of the impending cum storm, but darned if it didn’t spurt out before he could articulate. Half of the gooey cream went into Chrissie’s wet mouth, the other half over her pretty face.

Where was all this cum originating, Chrissie wondered. The boys she had sucked off never had half that much. Mmmmmmm. Having a man was wonderful!

Gary’s knees buckled and he had to sit. Chrissie plopped on his lap and began to kiss him. Gary’s cum smeared both their faces, but neither was deterred.

Their hot kissing had both lovers panting with lust. When Gary’s cock stood tall as ever, he began to consider a very naughty possibility. Chrissie would never….. It would be wrong…

Chrissie whispered in Gary’s ear, then gave it a sexy lick. "I’m all lubed in my sissy pussy," she breathed. "I want us to make love now."

Holy moley! Gary wanted to fuck this teen sissy more than he wanted that red bike for Christmas when he was eight. He should walk away, though and deny anything happened. Because it didn’t, really. It was only "oral," which isn’t sex. Right?

Instead, his mind searched through the positions in which he had seen the lovelies in "Panty Boy" taking large doses of cock. Finding the appropriate posture, he took the initiative for the first time.

Gary asked Chrissie to remove her dress. Wow! She looked fantastic in her lingerie! Gary stripped naked, then had Chrissie sit on his desk. He asked her to spread her legs and raise them. Chrissie eagerly complied. She was glad he was being the man.

Gary supported Chrissie’s legs with his arms, his forearms under her calves. He kissed her deeply, then took his big hand and aimed his cock at Chrissie’s tiny pucker.

"Are you sure?" he asked her.

"Fuck me," she demanded.

Gary pushed slightly forward and Chrissie experienced a brief second thought. That cock was big. Bigger than anything that had ever been in her little pussy. She wanted to take it all or die trying.

Gary felt Chrissie’s sphincter strain against his peehole, protecting the fortress from invaders, welcome or unwelcome. He sort of wiggled and pushed at the same time and the guard surrendered. You can’t get good security help these days. Chrissie yelped as she felt a large, blunt object deliver a little pain and big pleasure.

To reassure Gary, she whispered, "More, Mr. Milford. Please!"

Gary pushed again, getting the head and two thick inches well-seated within the walls of paradise. Gary’s libido went into overdrive. Fucking a panty boy was ten times better than he had fantasized. And he had several inches, fifty pistoning pushes and dozens of sweet, coital kisses to go.

In that position, the lovers could kiss. So they did. Gary pushed again and again along the walls of a cave thoughtfully lubricated with vaginal jelly. Had Chrissie been hoping to be caught or was she going to let that Andy do this to her? Gary thought. Then he said, the heck with it and resumed his fucking.

Chrissie squealed when Gary’s big meat was fully engulfed. She was totally filled with manly meat and her own cock was rubbing against Gary’s hard, hairy belly. The kissing, the beautiful fucking and the exquisite sensations assaulting her prick put the sweet sissy in a cum-promising situation. She grunted twice, then screamed as she doused Gary’s belly and chest with her sticky juices. Oh, that was grand!

Gary became a fucking machine, kissing the shuddering lovely as he pushed and strained toward his own orgasm. It arrived with the force of an idea whose time has come. Gary’s breath grew short. His vital signs flickered. Then he bellowed with joy as his boiling cum blasted into the tiny space occupied by his cock.

Chrissie counted five hot blasts entering her bowels. The cum enema made her feel a cramp of need for voiding, but she held on and the moment passed.

Gary kissed the lovely, whimpering Chrissie with a joy he had never known. Chrissie’s anal muscles involuntarily expelled the limp invader and a flood of cum soaked her thighs, dribbling to her stockinged knees. What a mess!

Gary broke the clinch with Chrissie and felt another wave of guilt. Yes, Dear Reader. Gary was Catholic. He sinned, but really didn’t enjoy it the way others did. But he was working through that.

Following the Sissy Code, which does not allow a sissy to send her man home with a dirty cock, Chrissie eagerly hit her knees again and tongue-polished off all the poop and cum remains of their delightful union.

Gary was 45 and couldn’t possibly get another big stiffie after two monster cums. And even if he did, his guilt would prevent him from bending Chrissie over his desk and fucking her from behind until she could barely walk in those big heels.

Right?

Wrong.

Though oddly matched, it appeared that Principal Gary Milford and high-school freshman, panty boy and budding she-male Chrissie Muller had become an item.

 

Chapter Eleven – Matty’s instructor

Blake Louis loved his wife Stephanie dearly, but thought she had lost it when she suggested that Blake teach high-school freshman Matty Marlow about sex with men.

Stephanie didn’t play fair. The night she asked, she was wearing a killer perfume, those fully-fashioned, black stockings, garter belt and seven-inch-stiletto, fuck-me pumps. She had spent about three hours on her make-up and she almost made Blake cream his pants when he walked in the door.

But that night, before she would even kiss Blake, Stephanie wanted to discuss "important matters" related to the sissiest boy in history. Matty Marlow.

"This boy needs the sexual attention of a man. A man who knows how to satisfy a sissy’s needs. Just as you can satisfy mine after you agree, Blakiekins. He needs instruction and milking. He needs a man’s cum in his belly. But it has to be a nice man. A loving man. You. Then he’ll have the self-confidence to go after his boyfriend, Zack Lincoln, and live happily ever after."

Stephanie’s titties jiggled a little as she said all this. Had she rouged those nipples? She was stroking her clitty as she spoke, then pulling up little strands of pre-cum to make a string up to a foot. Blake was naked and his cock was outrageous. His balls were aching. He hadn’t cum in TWELVE HOURS!!!

Blake tried reason. "But Stephanie, Honey. First, it would be cheating on you, which I‘ve never done. Second, it’s very illegal. Third, it’s weird."

Stephanie smiled. "First, I don’t consider it cheating. It’s therapy for someone in need. Second, legal, schmeagle. That little sissy needs help. Third, it’s not half as weird as going days, even weeks without sex." She smiled again and waited.

Who do you think won the argument?

The next evening, through arrangement with Matty’s mother, to whom Stephanie had gotten VERY close, Matty was to go to the Louis house.

Since they had no secrets from each other, Annette had told Matty all about her growing affection for Mrs. Louis. She also told Matty that Mrs. Louis had been very much like Matty when she was growing up – a boy in name only – and that she had developed into a beautiful woman, with a devoted, hunky husband. As well as a full, working set of male "things" that Annette was enjoying very much.

Mrs. Louis had found her "Zack" in Mr. Louis, now Mr. Louis was going to help Matty learn all about men’s bodies so she could give Zack the pleasure that drives men insane with lust and impels them to buy engagement rings.

Matty was a little nervous about being at the complete, helpless mercy of a big, hairy, overheated, animalistic man, but Mommy said it was the right thing and she had, as always, complete trust in Mommy.

Matty was also a bit worried about "cheating" on Zack with that big, hairy man, but Mommy told Matty to think of Mr. Louis as an instructor, not a lover. Matty’s tiny pricklet still stiffened at the thought of her "instructor," a man she had seen several times. A man who stirred her sissy balls every time she had seen him.

That Friday afternoon, Matty had her usual after-school snack of breast milk, but Annette omitted the usual milking. Annette wanted Matty to be sexually on edge and full of girlie cum for a wonderful night of instruction.

Annette dressed Matty in the prettiest "big-girl" frillies she could find. A lacy bra covered Matty’s pretty little nipples, which seemed to be tingling since Mommy had started those shots a month earlier. Skimpy silk panties rubbed against Matty’s over-excited pink knob and there was a big, cummy "accident" even before Matty and Mommy left the house. Mommy laughed with Matty and said a sissy’s excitement about wearing pretty things and submitting to a man made things like that happen. There were always fresh panties and lots more sticky cream where the last gooey load came from.

Matty had the perfect Mommy.

Meanwhile, Blake Louis was a complete wreck. He was worried that one day, even though Stephanie had even used the ultimate threat (no sex!!!) to get her way about Blake fucking little Matty, Stephanie could throw this night back at him somehow. Such a thing is not without precedent within a marriage, it is rumored. He was also worried about Matty’s mother accusing him of something and police sirens at 3 a.m., busting down his door and throwing him in jail. And he was worried about Stephanie spending the night fucking Mrs. Marlow. What if Stephanie decided she liked women more than she liked him. In college, Stephanie fucked half the coed population. And one man. Blake.

Then there was that nagging fear that the kid wouldn’t want his attentions.

Or even that Blake would be unable to perform his manly duties. Imagine how humiliating that would be!

Blake almost jumped through his skin when the doorbell rang at 7 p.m.

Stephanie answered the door. She was all tarted up for her night of Sapphic pleasures with that Annette Marlow, who, Blake thought, was quite a babe and clearly needed a man’s sexual attention.

When Blake saw Matty, his heart skipped. He felt as if it were Blake and "Gilbert" and he was a teenager all over again. Blake saw a pretty, sexually eager, but totally innocent and totally feminine person.

Matty saw the kind of hunky guy she imagined sometimes when she had those dreams that messed her sheets. Blake Louis was six-foot-two and weighed about 205 hunky pounds. With a 48-inch, hairy chest that tapered to a 32-inch waist. Blake was rippled with athletic muscles that came from fucking his sweet Stephanie more than twelve hundred times each year. He was rugged and manly and Matty couldn’t help thinking about what was then in his underpants and soon to be in Matty’s tight sissypussy.

And Mommy said it was all right.

Stephanie kissed Matty in greeting. She smiled when saw the high-voltage spark that had already passed between her husband and Matty, the ultimate sissy.

Stephanie introduced the two tongue-tied lovers for the night, then kissed Blake goodbye and whispered, "Remember, the two of you can do everything! I want you to teach Matty everything you can teach someone on one night. I’ll be by with the hearse for your body at nine tomorrow morning."

Blake smiled weakly at Stephanie, then said, "This will be the first night we’ve been apart since we married."

Stephanie breathed, "I know. And I plan to make it up to you. And to reward you for doing this for me and Matty."

Blake thought, so I get to fuck this incredible doll all night, then my wife rewards me?

OK, it could happen.

Stephanie kissed Matty, noted how serene and submissive she was, then departed.

As the door closed, the strange bedfellows faced each other.

Blake cleared his throat and studied Matty’s classically beautiful face. He wondered, as he did with his wife, how a boy could look like that. He loved Matty’s cute, though short hairdo, her silky white stockings, pretty dress and sexy stiletto sandals.

"Would you like a soda or something, Matty?"

Matty smiled. "No thank you, Mr. Louis. Mommy says I should sit on your lap and kiss you for a while, then do whatever you say all night long."

<Gulp> "OK, Honey. You’re very pretty and sweet and feminine. Kissing you will be a great pleasure."

Matty blushed and thanked Blake.

Blake sat in his easy chair and beckoned Matty to his lap.

She placed her bottom on his right thigh and her legs over his left. She was light as a feather and smelled like spring flowers. Poor Blake was hard already. Matty, the little minx, rubbed her left thigh against Blake’s stiffie as she put her head on his broad chest.

Blake was intensely excited. His khaki pants were severely tented. Matty loved feeling that iron bar rubbing against her stockinged thigh. Blake loved looking at Matty’s skirt and seeing the tiny tent her stiff weenie had created.

Blake said to himself, "My wife wants me to do this. Matty’s mother wants me to do this. Matty wants me to do this. And I certainly want to do this."

So Blake put his right arm around Matty, lifted her pretty chin with his left hand, and kissed Matty’s sweet, red lips.

Sparks flew.

They kissed again. With hunger and need. Matty gave herself over to the man and the emotion. Blake fell in love for the second time in his life.

Lips. Eyes. Throats. Tongues. Cheeks. Tonsils.

The temperature in the room went up twenty degrees.

Their clothes were too warm. Had to get them off.

Blake stripped to the buff; Matty to her stockings, bra, panties and very high-heeled sandals.

But it was still hot in there.

Matty sat back down on Blake’s naked lap and was in awe at the wonder of his naked body. Especially his <blush> drooling, iron pipe of a cock.

Blake eyed his sissy prize. She was sweet, beautiful and totally submissive. Her little nipples were hard with excitement. Her little sissy cock, which was the size of Blake’s little finger, was skinned, pink and very hard. Her tiny balls were encased in a pretty pink bag and they looked delicious.

Matty was naughty first. She rubbed the pink, drippy head of her little popsy along the length of Blake’s big rammer.

Blake’s cock exploded, spewing boiling cum all over Matty’s hands, privates, tummy and thighs. The hot cum on her balls and the joy she felt at giving Blake pleasure made the lovely girl shudder and lose her own goo. She squealed like the sissy she was as Blake continued to empty his balls all over her.

For a man used to cumming three or four times a day, a man who knew his orgasms, his first ejaculation with Matty was an exceptional spermblaster.

Matty thought so too. She was whimpering with lust and ready for whatever her man suggested next.

Once Blake got his leg strength back, he picked Matty up and, kissing her as he carried her, took her upstairs to his bedroom.

Blake placed Matty on the bed and joined her, lying by her side.

"You’re incredibly beautiful," he said in all honesty.

Matty beamed. What girl doesn’t enjoy hearing that?

Blake kissed Matty as he explored her body with his rough, strong hands. Matty wiggled with pleasure and her little peener was hard once again. Matty wondered if she would be able to get even the head of that monstrous sissypleaser in her mouth. He couldn’t possibly expect to put it in her little bubble butt, could he? That was scary! And very exciting. Mommy warned Matty that men want to "shove their business in you." Was that what Mrs. Louis was doing with Mommy? Shoving her business into Mommy? Well, Mommy knew best about such things.

Blake was a bookworm standing at the door of the Library of Congress. The general manager with every draft pick for the first round. A guy with a sweet tooth locked in an ice cream store overnight.

He chose his flavor.

Blake lay on his back and asked Matty to straddle his shoulders. Blake wanted to suck Matty’s pricklet and swallow her sweet cum.

Matty complied, squealing softly when she felt a man’s lips on her prick for the first time.

Blake knew his art, swirling his tongue around Matty’s wee just the way Stephanie liked it. That seemed to be just fine for Matty, whose head was thrown back in ecstasy. Blake tickled her balls with his left hand and tickled the tiny rosette of her anus with his right.

Oh.

Matty felt that first little signal and surrendered to it. The second one was right behind it. Then the point of helplessness was passed and big globs of sticky cream spurted into Blake’s hungry mouth. Blake sucked lovingly through Matty’s spasms and soft squeals, then licked her clean. Her cum was delicious and Blake wanted more.

But Matty knew her duties as a sissy. She kissed Blake in gratitude, then moved to his right side. On her knees on the bed, she began to kiss Blake’s cock along its hot length. What she lacked in experience, she made up for in beauty, sissiness and enthusiasm.

Blake enjoyed it a lot. Matty’s hot, red lips and tiny tongue explored and caressed each sensitive pore. She made little lick-ups of the drooling semen, purring with contentment as he moaned with lust. Matty spent ten lovely minutes licking and kissing Blake’s big, heavy balls. Then she began her final assault on the hundreds of erotic nerve endings on the cockhead, which, we all know, also encases the male brain.

Blake was in sissylover heaven as Matty’s plentiful saliva bathed his knob. The little angel stretched her tiny mouth and got the whole head in. Blake trembled and felt his spermstorm approach.

Matty tongued the sensitive underside of Blake’s cock. Licking things just right. Making little grunts of pleasure as she tormented him with her sweet tongue.

Blake surrendered to his orgasm. Thick, cummy globs nearly choked the sissy princess, but she held on bravely, swallowing the mannish goo with pride and need.

Matty had come into the evening thinking of it as a dress rehearsal for her seduction of Zack, but she was enjoying herself tremendously.

As was Blake. Maybe Stephanie would need to bring that hearse after all. His balls had pumped out a small ocean of cum. His chest was heaving.

Matty swallowed the last of her hearty meal and licked her lips. A born cocksucker, she was eager for more.

Blake drew the angel to himself for more kissing. Mmmmmm.

Matty began to tease Blake’s chest hairs, especially around his nipples. No one had ever done that and Blake enjoyed it very much. So much that he had a quarter of a hardon again. How did that happen?

Then Blake decided to investigate little Matty’s nipplish regions. Looking at her little nubbers for the first time, Blake saw that Matty’s breasts showed signs of development. He remembered when his darling Stephanie’s were in that stage and he sighed with nostalgia. Matty’s nipples were pointed, pouty and in need of some masculine attention.

Blake kissed and licked Matty’s right nipple. Shocking them both, Matty arched her back, squealed and spunked herself for the third time that glorious evening.

Wow. Talk about sensitive.

Showing no mercy, Blake continued to kiss and lick Matty’s little puffies as she whimpered and begged for him to stop. Of course, when he stopped, she begged for him to continue until she shuddered and came yet again,

The little creampuff was a cummy mess until Blake went down on her and licked her clean, with special attention to her cum-drenched balls. Matty was moaning and mumbling. Then Blake lay on his back again and placed Matty on his manly body, rubbing his hairy chest against her hair-trigger nipples and kissing his little angel lovingly.

Matty continued her mumbling until Blake was overtaken by curiosity. "What are you saying, sweetheart?"

Matty blushed. Then she said, shyly and very sweetly, "I love you, Daddy."

Oh my. That had three immediate effects on Blake. First, it made his cock engorge with hot blood. Second it filled his heart with joy. Third, it filled his head with complications. He was married. She was, well, who she was and not for him. But, like most men, Blake was able to suppress logic when the immersion of his cock in a tight, warm place was imminent.

He kissed Matty tenderly and said, "I love you too, princess. You’re a perfect angel."

Matty glowed with love and hugged Blake very hard.

Blake kissed her for a while, then rubbed the pad of his right middle index finger against Matty’s anal ring. Matty squealed softly, then pushed against his finger for more. In addition to being beautiful and sexy, this girl was a little cockhound as well. She really was perfect.

Blake entered Matty anus with his finger to the depth of a nail and she squealed more loudly and wiggled against him, kissing his neck as she lightly pinched his left nipple.

Wow.

Blake slipped the entire finger in and began to rub it up and down Matty’s anal pussy. Matty was clearly eager for a full, knock-down-drag-out fucking. She panted with passion and rubbed her stiff sissy wee against Blake’s big boy. "I want you, Daddy," the little teaser said.

Blake realized that without preparation, that tiny, gorgeous, tight bottom would suffer under his attack. So he had Matty straddle his shoulders while facing his feet. He then coached her into lowering her perfect little bottom onto his mouth.

A feast of love was begun when Blake’s practiced tongue licked the inner folds of Matty’s bottom cheeks. Her bottom was pink and warm and very tasty. Blake’s tongue tipped Matty’s pink rosebud of an anus and Matty cried out, "Daddy!!!"

Blake pushed his tongue past the heavenly gate and tasted Matty’s sweet anal juices. Matty began to whimper loudly and verbalize. "Oh, Daddy. Please keep doing that. Oh, please." Blake eagerly complied, putting his hot dart in farther and drawing more frantic wiggling and cries from his angel. He needed her to be wet and open so he could fuck her properly, so he showed no mercy. Matty’s poor little balls were empty, but she orgasmed anyway, screaming, "I love you, Daddy," as her cocklet twitched and a small, watery drool ran from her pink peehole.

Blake loved every carnal moment.

He took inventory. Matty was wet and willing. Blake was stiff and willing. Let’s fuck, he agreed with himself.

Blake really wanted to fuck Matty on her back, in full submission to his manly needs. But he thought that it might hurt Matty that way. So he decided to let her ease herself on to him at her own pace.

Blake turned Matty around and said, "Do you want me to fuck you now, Sweet Baby?"

Matty bit her pretty lip and nodded eagerly. She was hot, wet and ready for anything.

Still on his back, Blake pointed his stiff monster skyward and showed Matty how to straddle his hips and face him as she sat on her impaler.

Matty showed no fear as she got into position. Blake placed his wet peehole at her tight opening, then watched in amazement as the eager sissy’s crack opened and she made his cock disappear into the tightest, hottest place it had ever been. Once again, she was amazing him! When she was totally stuffed, her eyes bulged and her weenie was stiff yet again. Blake told her he loved her, then held her hips as he moved her up and down his cock. Her squeals and gasps and pants and whimpers had the man reeling with pleasure.

Blake was able to hold off from cumming, but only because it was his third gooey load of the evening. When Matty’s bottom was loose and her anal juices produced a smooth path for Blake’s hot piston, Blake maneuvered her, without withdrawing his cock from its delicious confinement, onto her back.

Matty loved being fucked like a woman. On her back. With her legs up and toes pointed. Wiggling. Helpless under the hairy man who covered her. Dominated her. Made her squeal. Kissed her and rubbed his stubbly face against hers. Pushed his "business" in and out of her. Treating her like a toy for his pleasure. Matty couldn’t cum again. It was impossible. But when Blake’s snorts and grunts signaled his impending crisis, Matty threw her legs around Blake’s back, dug her nails into his back, screamed with animal lust and emptied her tiny balls yet again.

Blake made three hard, fast strokes, then reeled with the force of his mother of all cums. As good as any he had ever had with his dear wife Stephanie. Maybe better. Who cared? It was great.

Matty’s bottom felt a man’s hot goo for the first time. She whimpered and cried with joy. She was a complete sissy now. Had given herself completely to a man. Had taken his seed into her. Had eaten his cum and taken it as a suppository. And was overjoyed that she had done so.

The lovers spent the next ten hours making sure that Matty’s sissy inoculations were complete.

 

Chapter Twelve – Parental Involvement

A few days later, Principal Gary Milford received a most disturbing message. Chrissie Muller’s father wanted to see Gary, in Gary’s office, at 5:30 p.m. that day, on a matter of great urgency.

Since Gary had been thoroughly fucking Mr. Muller’s sissy son three or four afternoons every week, Gary suspected that he had better get his affairs in order before the meeting. He wondered what life in the Big House would be like. Maybe he would meet some nice sissies in there. Or maybe Mr. Muller would be bringing a large-caliber weapon and such notions would be pre-empted.

No matter. Gary accepted his fate with the fatalism of one who has, despite huge potential consequences, chosen to live his dream, regardless.

At the appointed hour, the school was empty, except for Gary.

Gary’s office door opened and he braced himself for an onslaught, first verbal, then perhaps violent. Stoically, he stood. And looked at his visitor.

An extremely attractive, feminine masterpiece. Late thirties, but very well dressed, made-up and put together. So Chrissie’s mother came instead, was Gary’s first thought. His second was, what a dish! Why did so few women take the care this beauty had taken.

Then he looked a little more closely and felt his sissy-sense tingle.

Could it be?

The lovely babe said, "I’m Lisa Muller, Chrissie’s father. Are you Mr. Milford?"

Apparently, things weren’t as bad as Gary had imagined. "Yes, ma’am," Gary said.

"My son Chrissie tells me things about you. Good things. She likes you a lot. Do you like her a lot?"

Gary nodded. Lisa sat on the edge of Gary’s desk. Her mid-calf-length skirt was deeply slit and a pair of gorgeous, tan-stockinged legs was revealed to a very interested man.

Lisa noticed Gary’s attention and slowly raised her skirt to reveal first dark stocking tops, then creamy white thighs. Though she was silent, she was communicating her intentions quite well.

Gary was very relieved. And very excited.

Lisa said, "I’m married, you know, Mr. Milford. A wonderful woman whom I love very much. But I need a man too. A real man. Hard where it counts. Gentle, but firm with me. A master when I want one. A man who can climb on top of me and drive me to paradise. I haven’t had one of those in months. The pantywaists I work with aren’t worth my attention. They’re not real men. Maybe you’re a real man. Chrissie tells me you are. Are you, Mr. Milford?"

Gary knew the exact, subtle move for that situation. The move we all have dreamed about making, but never have. Silently. Gary Milford pulled down and removed his trousers, then his underpants. His huge, erect cock, hairy balls and manly legs spoke eloquently.

So did Lisa’s next move. She fell to her knees and kissed, frigged, sucked, licked, wanked, stroked, tickled and caressed Gary’s big meat until he coated her face in a thick layer of hot, manly balljuice. Then she got on her back on Gary’s bare desk, frantically pulled her panties down and off, and spread her legs. Gary hit his knees and ate out her delicious bottom until she begged for a fucking. On the first stroke into her tight hole, Lisa screamed and came. And on the 46^th stroke. And on the 102^nd, at which time Gary joined her in ecstasy.

Sometimes things just work out.

And in and out and in and out.

Lisa and Gary became very good friends from that moment on. And Gary only read "Panty Boy" for the articles after that, because he had all the sissy pussy he could handle.

 

Chapter Thirteen – Zack and Matty’s Lucky Night

Three days before Christmas, Annette was very pleased with her sweet Matty’s progress.

Matty had gained in confidence and was ready to take the two biggest steps in her life. She was going to reveal herself as a girl first to Zack, then to the world. Of course Matty was planning to reveal a LOT of herself to Zack.

What a lovely girl Matty was. So sweet and feminine. So submissive to her Mommy and to a man during lovemaking. But with such backbone for one so small.

Annette smiled when Matty asked for another "confidence-building" night with that hunky Mr. Louis. And another session after that. Of course Matty couldn’t get enough of that big cock and hairy balls. What sissy could?

And Annette surely loved the nights she spent with Stephanie, the poor displaced wife. It was wonderful to feel a thick cock in you as you kiss a beautiful, lipsticked mouth and feel stockinged legs rubbing nylon-to-nylon against you. Wonderful and confusing. Annette wasn’t sure whether she wanted a man or a woman, but she knew that she had been celibate long enough.

Annette was so happy that her brother-in-law Lisa had arranged things for Matty with her principal, Mr. Milford. He had agreed to give the administration’s full support to Matty beginning after the new year to dress as and become a full-time girl. Mr. Milford was unusually cooperative about everything. Lisa had apparently done the right kind of groundwork to convince Milford that he would be doing the right thing.

That night, Annette had invited Zack for a tree-trimming and sleepover. It would be the first time that Matty and Zack had been alone since "that night," a fact that was not lost on Zack.

Looking at Matty and wanting someone Zack still thought of as a boy was torment for Zack. A thousand times since "that night" Zack had wished that Matty was a girl.

He was about to get his wish and so was she.

Zack arrived at six p.m., as invited. He was nervous, confused and terribly eager to see what would happen during a night alone with Matty in a bedroom.

Annette greeted Zack warmly. "Merry Christmas, Zack. I’m so happy you could come. Let me take your coat."

"Thanks, Mrs. Marlow. Is Matty in his room?"

Annette smiled. "Yes, Zack. She’s in her room waiting for you. Why don’t you go up and see her. Take all the time you need."

Zack froze. "She?" "Her?" Could it be?

Annette said, "Scoot, now. And don’t worry about me. I’ll be downstairs minding my own business."

Zack gulped. His heart pounded so loudly he thought Mrs. Marlow could surely hear it.

Zack took the stairs two at a time, stood in front of Matty’s door, sighed heavily, then entered.

It was a good thing Zack was young and had a strong heart. Matty was on her back on her bed. Her face was made up perfectly. Her hair was beautifully coiffed. She was wearing only seamed black stockings. And her little peener was stiff, dripping and throbbing.

Matty whimpered and held out both arms toward Zack.

Somehow, between the door and the bed, Zack lost every stitch of his clothing. And all his inhibitions about "gayness." Zack’s dream was coming true and he was determined to see where it took him.

Zack mounted his Love, covering her with his hard, naked body. He kissed her full on the red lips and she threw her arms around him. After a deep, delicious kiss, Zack paused, moved his head back to gaze in Matty’s beautiful eyes, and said, "You’re a beautiful, kind, sweet person, Matty. I love you. I’ve always loved you."

Matty’s eyes leaked with happy tears. "I love you too, Zack. We were meant for each other, right from the beginning. I’m going to be a girl from now on. Your girl."

Zack was stuffed with joy. And his cock was stuffed with blood.

What an exciting sexuality Matty had. She was beautiful and giving and loving and innocent. And she was Zack’s for the taking.

Zack began to make love to Matty by kissing her on the forehead. She purred sweetly. Then he began to explore her entire body with his kisses, all the way to her pretty toes. Matty was squealing with pleasure. When Zack kissed a trail back up to her inner thighs, then gave her tiny balls a good licking, Matty’s eyes widened. She grunted, arched her back and spurted her sticky cream all over her tummy. Zack was delighted that he could give her such pleasure. The eager boy licked Matty’s cum from her popsy, but used his fingers to pick up the cum form her stomach to her little wrinkled tulip. Using the natural lubricant, Zack entered his love with his fingers. She moaned loudly, then insisted on some kisses. The naughty boy continued to kiss the sweet sissy as he rubbed her cum along her anal passage. And rub. And nip her prostate. And kiss. Matty was inarticulate, but her gasps of pleasure told Zack that she was near another sweet crisis. So he kissed and rubbed more furiously until Matty squealed with gusto and spurted four more big, thick, creamy globs of sissy juice.

Matty was in heaven. But she wanted to please her man as well as he had pleased her. Matty slipped her body down and took Zack’s thick cock into her warm, wet mouth. Zack shuddered with pleasure. But after ten or twelve delicious sucks, Zack pulled Matty gently away.

"I want to spill my seed in you and make you mine forever," Zack said.

Matty glowed with love and anticipation. Her experience paying off, Matty wiggled onto her back and raised her legs, offering her tight love passage to her man.

Zack was fatally excited, but his cock was strong and ready. He mounted Matty, putting her calves on his shoulders. She was trapped! And about to be fucked by a snorting, rutting stud. Goodie!

Matty knew she could take Zack inside her, since Mr. Louis’ larger weapon had been a frequent flyer in her pussy. But she knew that every man wants to believe that his girl can barely accept his big weapon. So she grunted and squirmed as Zack entered her slowly. She even said at one point, "Maybe it’s too big," which to a man translates to "Push harder, Big Boy."

When Zack was all in, Matty felt every bit as stuffed as she had with Mr. Louis. And twice as happy. Zack was her man; Mr. Louis was Mrs. Louis’ man.

Her man was enjoying himself immensely. It was his first fuck and his eyes were bugging with pleasure. Nature told him to push back and forth. Matty’s sounds of pleasure reassured him that he was doing it correctly.

Zack was able to lean over and kiss Matty as they fucked, which added oodles to the experience. So did Matty’s proclamation that "You’re making me cum again, Baby. What a man you are!"

Matty was right on both counts. She screamed to wake the dead as her valiant balls produced yet another big load. His ego stroked as well as his prick, Zack’s guts clenched, his toes tingled, then curled, his nipples erected, and for the first of thousands of times, he emptied his nuts into his partner-for-life’s hot, tight pussy.

Matty felt each titanic surge. She clutched her Zack and shook with sexual fever. Zack pumped and groaned. And fell in love for life.

And so it began.

Four hours later, after many cummy permutations of Matty and Zack’s lovemaking, Annette decided to "check on the kids."

She entered the room and saw a naked Zack on his back. A cum-soaked Matty was on her knees sucking Zack’s good-sized cock hungrily. How sweet! Annette had heard all the noises and the cum smell had wafted downstairs, but it was good to see their fun in person.

Zack, who in his joy had completely forgotten about Mrs. Marlow, almost fainted when he saw her.

He recovered when she said, "I’m so happy for you two. You’re doing that very nicely, Matty dear. A little more attention to the peehole with your tongue, I think."

Matty stopped sucking, said, "Thank you, Mommy," then resumed, with more tonguey attention to the peehole.

Zack wasn’t sure which planet he was on, but he wasn’t going back to earth.

Annette sat in a chair, smiling sweetly, until Zack gave up his seventh and wateriest load of the evening. Matty lapped it up, cleaned him off, then kissed Zack soulfully.

Annette said, "Matty, dear. Would you and your boyfriend care for a nice warm, snack?"

Matty grinned. "Oh, yes, please, Mommy." Then she stood up.

Zack wasn’t really hungry, but playing along had worked very well so far with the Marlows, so he stood too.

Annette put additional pillows at the bed’s headboard, then propped herself against them into an erect position on the cum-drenched bed. She removed her blouse, then her bra.

Zack’s eyes were filled with wild surmise. Matty lay next to Annette and with a practiced grace, took a nipple into her mouth and began to take little sips.

"Zack?" Annette invited.

Zack thought, when with the Marlows, do as the Marlows do. He lay on Annette’s other side and took her huge nipple into his mouth. Oh my. It was tasty and wildly intimate. He felt he was connected to Matty, who was sucking greedily on her snack, through Annette.

Zack’s cock was stiff again.

Annette said, "Zack, you’re getting me very excited, would you please reach under my skirt and pull my panties down as far as the garter straps allow?"

Oh. Zack did so. His fingers brushed against Annette’s pussy, which was hairy and sopping.

"Keep nursing, Zack, but please rub your fingers against this little nub right here. No. Not that. This one. That’s it. Keep….uhhhh….doing that. Lovely. Very nice. Ohhhhhh."

Zack rubbed and rubbed. And nursed and nursed. Annette squealed and squealed. And came and came.

And they all lived happily ever after.

 

 

 

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© 2002 by Gingerfred Man. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.