Sissy Tale Mother's Suffering Sheboy
Alan GlenDragon
Mother's Suffering Sheboy by TJ Ryder
Once the BlackRule Party gained control of the province, Terry felt it was just inevitable he'd be in the position he was in. But still, returning to home he left to go away to school with with his mother and twin sister near the newly renamed Makumba Beach it was still a shock.
Despite his years of Obeah-sponsored, Black-respect indoctrination, his cosmetic surgery and submissive socialization seminars for whiteboys, he found it hard to adjust to the twin demands of both his mother and sister, but the cultural demands for white sheboys.
For example, he was expected after almost a year away in school to resume being the family maid, that was bad enough in itself. But he also had to make some serious changes in himself to suit his dominant twin sister.
Sighing, he walked to her bedroom following his mother in her sheer shortie negligee. His beautiful voluptuous mother was only 37, and she had dominated since his earliest memory, along with his sister. Of course they were also BlackRuled like everyone was in this province, he still hoped for a social life on his own like what he enjoyed away at school, to no avail.
"Terri," his mom said, "come with me now, I want to see how your'e doing now!"
"Yes ma'am," he said meekly. He trembled, seeing the paddle laying across his sister's bed and her smirk as she sat on the edge looking up at him.
"Well, dear brother, have you been good?"
(Gulp) "Um, y-yes sis!"
"I wonder!" Both women sat on the edge of the bed, as he stood before them, wondering what was going to happen next.
"Hmmm," his mother said, frowning a little, "hairstyle not quite right."
His sister Traci mocked, "he can't pass at all for me, mother, nothing's right!"
Marya Redmond nodded, making Terri tremble. "Well, that's what wer'e here for, darling. Now, Terri, I know youv'e been away for sometime, but it seems youv'e forgotten many of our rules."
"Um, ma'am, I, um, couldn't help it. The BlackRule Master told me he preferred ponytails at the camp."
"Well, you know how important it is to pass as either your sister or myself when it's convenient. Just because your'e away doesn't mean you should be disobedient."
"He should be whipped for that, mother!"
"Let's take it one by one, dear, please write it down. Now, your hair of course. Restyled of course, but Traci's hair has gotten lighter with the sun. Make sure you take care of that tomorrow at the hairdresser, dear." Traci jotted it down on a notepad.
Standing in his french maid costume with his hands held meekly behind him, he also nodded. His mother looked up and down.
"Strip now, Terri, except for, mmm, leave the apron on for now!"
Swallowing he did so, even as Traci giggled. Soon he was standing in only heels, maid lace cap, lace apron and chastity belt. His large firm cosmetic breasts arched out as he put his hands behind his back, the big brown nipples already hardening.
"Hmmm," Marya looked him over critically. "Your ear rings don't match Traci's, or your nipple rings either. Wait," she said, standing up and picking up a tape measure. She measured his breasts, waist and hips.
"Well, waist is two inches wide, hips two inches narrow, but I suppose that won't show. But, look, darling, in the last year your breasts grew an extra inch since we had Terri's boob job."
"Oh, mother, that will definitely show. I want him to be changed, can't we do that?"
"I suppose, that shouldn't be too hard, getting an appointment this week."
Terri groaned, trying to keep silent. He thought his breasts were huge the way they were.
"Now, turn this way, sissy, no, now open your mouth. Ah hah, your sister has two tongue studs, you need one more, nearer the tip."
"It has to be the right size, mom, Tyrone will notice if it isn't!"
(Gasp) "yes ma'am!" He sincerely hoped she would at least inform her black boyfriends that he was just pretending to be her on dates but he wasn't sure she would.
"Now, hmmm, let's see your curtsy like we taught you!"
"Yes ma'am," he said, lifting up his apron and giving a curtsy, recovering and half smiling, only to see them both frown.
"You don't like it?"
"Something's not right! Do you agree, Traci?"
"Yes, here, let me stand to the side," she stood up and he trembled as she picked up her old riding crop.
He curtsied again, going deeper, but still they were not satisfied. After two more tries, his mother arched an eyebrow, and Traci smiled.
"Bend forward, sissy," she said. He did so, trembling.
"WHACK! AAAGGHHHH!"
"Now do it!"
He curtsied again, tears forming in his eyes.
"Does this please you, mistress?"
"Bend forward again, slut!"
(Gasp) "Y-yes ma'am!"
WHACK! MMmmfffff! It took several more tries before his sister put the crop down reluctantly.
"It seems better, mom, but something seems to be missing!"
"I know, but I can't put my finger on it. Anyway, take off the apron, sissygirl, and oh yes, we have to remove the chastity belt."
"Sissy wants to get hard I bet, " Traci smirked, and the combination of the cropping and humiliation was making his cock swell, and he immediately erected fully as his mother cupped his big testicles.
"These are bigger, fuller, I'm sure!" Traci also hefted them and nodded.
"Oh, and they have disgusting hair on them too. Look, hair all over her groin and testicles."
'Oh no,' Terri thought, trying not to panic. He never even thought of that, the possibility that his sister depilated her pubic area since he was last home. All he had to do was to use a hair removal cream before he came home.
"But,madame," he said, trying to placate them. "If it's just for show, nobody will notice because I'll be trying to pass for Traci anyway. If they take my panties off the jig's up anyway!"
"I think sissyslut is a little scared, mother!"
"I think so too, darling! Why are you acting so skittish, Terri?"
"Um, w-well, I-I wasn't... I mean I was just saying that, you know, it isn't really important. But, um, you know, if you think, um, well, I'll just have it all depilated by tomorrow. I saw some hair removal cream in the medicine chest."
Traci smiled, exchanging a sly look with her mother.
"But of course, dear," his mother said, "naturally you could do that, but that wouldn't really teach you a proper lesson, now would it? Do you think, darling?"
"Not at all," Traci said breathily, licking her full lips. "And I think Terri really needs a good lesson too, mother."
"Yes of course she does!" She agreed. "Now, before we get to that, do you want to see how tight she is too, dear?"
"Oh yes, " Traci said, getting excited now as her brother saw so clearly. Turn around and spread your cheeks, sissyboy!"
Groaning, fearing the worst, he did so, blushing as he bent forward as far as he could, reaching back and spreading his cheeks, exposing his pink anus in his buttcrack. He trembled as he felt his mother's smooth warm hand over them.
"You look tight, too, sissy," she said. "Don't you think, darling?"
"She sure does, mother. What happened back east, brother dear? Didn't your black boyfriend have a big cock or what?"
"(Groan) Ah, w-well, he didn't do that, um, too much!"
"But you should have worn your buttplug then. You know how important it is to be able to accomodate a black penis anytime anywhere, sissy," his mom said, frowning a little. "That's what we thought we taught you, and now it looks like you need another lesson still."
"I want to use the strapon for him, mother! We can do it tonight!"
"Have some patience, dear. Now, sissy, turn around and face me!"
Terri slowly turned around, noting his beautiful mother had already slipped off her short nightie, her big firm orbs swaying with hardening brown nipples, and saw her sister also slipping off her top. Unable to stop himself even knowing what was to come, or because of it he wasn't sure, he erected fully, the thick veiny phallus standing out at a 45 degree angle.
"Ooh, my, naughty shegirl gets a big clit over the prospect, doesn't she?"
"Pl-please, mother, d-don't..."
"But it must be done, and Traci so looks forward to it!" Terri thought that was as if his mother didn't love it just as much but kept silent.
"Why don't you lie across my lap, on the edge of the bed, Terri. That's a good girl. And darling, just do his ankles with the straps, and we'll do his hands in back of his head this time."
"Ooh yes," his sister grinned, "your'e going to be sorry now, sissy!"
Soon his ankles were manacled so he couldn't lift them or even move his legs together, lying over his mother's warm smooth thighs, her big swaying breasts inches away, as she smiled down at him, even as Traci handed her a pair of tweezers, keeping one pair for herself.
"Oh my, Terri," she sighed, licking her full lips in anticipation, even as her soft hand moved over his genitals, stroking him harder, and lightly pulling on the dense curls of blonde pubic hair on his testicles, "it does seem forever since I had the pleasure of doing this."
"Its been ages," Traci agreed, her eyes bright, meeting her brother's frightened eyes, "but let's take our time, mother. And then guess what, Terri dear, I'm going to ream you nice and long and hard. But you'll be well broke by then, I assure you."
Squeezing his thick cock, moving it a little, Marya smiled down at him, lightly pulling a few pubic hairs form his genitals, making the skin stretch.
"Oh yes, Terri, get nice and big for us, stretch all the skin out so we can do a nice proper job."
"Ooh, don't let him cum, mother, that would spoil it!"
"Oh, don't you think I know, dear? Mmmm, that's it, sissyboy, mmm, get hard for your mother, but you won't cum, ohh no, we can't have that! Yes, it feels so good now, but soon, yes, soon, you'll be screaming like a baby!"
Terri gasped, unable to not stiffen in her hand stroking him, seeing the big breasts and thick nipples swaying above his face. Traci looked down at him arrogantly, licking her upper lip, smiling smugly.
"Ooh yes, sissyboy, and afterwards I think I'll put some pincher clothespins on your big nipples too. I'd whip your breasts if you didn't have to pass for me in a few days."
"Pl-please, (gasp)," he stiffened, feeling panicky now but unable to stop even his own body from responding.
"Do you want to go first, darling," she asked, leaning forward to kiss her daughter on her lips, their tongues swirling together.
"Mmm, (smack) ooh, you go, mother, I want to watch his face for now!"
Feeling his cock almost contract, his balls tighten, Marya shut his strong approaching youthful orgasm down, and then put the tweezers with her right hand on some hair near his testicles, making sure the hairs were tightly squeezed, she sighed, looked at Terri's flushed face along with her daughter, and slooowwwly pulled upward.
MMMMPFFFFFF! Terri squealed, trying to arch his groin but kept back by the straps and Traci's weight on her hand on his chest, until the fiery pain made him scream out! One by one each hair caught in the tweezers popped free of its roots, making the scream long and drawn out, sweat popping out on his face chest and big breasts. After the last hair popped free, he sank back on his mother's thighs, as both women took a long sighing breath.
"Now, stop crying already, sissy!" Marya said with satisfaction.
"Yesss, " breathed Traci, "we have so much more to do yet, (giggle)!"