A Sister's Revenge Ch. 01

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"Well darling," Mary said. "I was going to wait a little while longer, like usual, but I wanted to give you this to wear along with your other undies so you wouldn't just be wearing your underwear to bed, and so I decided to do both and kill two birds with one stone, so to speak."

Then, taking her hand from behind her back, Mary handed Michael a very beautiful looking Black transparent silk Baby doll nightie. "I want you to put this on over you other clothes to wear to bed, sweetheart. They'll help you sleep better and keep you much more comfortable while you do."

"What is it, Mother?" Michel asked incredulously. "Are you sure this is necessary? I mean..."

"Yes, dear, I'm sure," Mary said almost commandingly. "Why are you always questioning me? Haven't you learned yet that I always know what's best for my little pumpkin? Have I ever steered you wrong, my little one, or given you any bad advice? No, I haven't, and you know it! So please, for once, will you just listen to me and do as I say...please?"

"Yes, Mother, I will," Michael answered contritely. "You're right, you've always known what's best for me, and I will try to remember that and not question your orders from now on. I'm really sorry, Mother."

After saying those words, Michael took the soft, silky nightie and slipped it over his head, and again shivered as he enjoyed the feeling of it slipping and sliding its way down over his body.

"Good boy, Michael," Mary cooed. "You look very nice in that outfit, really you do. If you had a bow in your hair, you would look cute beyond words."

"Oh geeze, Mother," Michael moaned as he tried to picture that image and was at least glad it was difficult to come up. "Puulleeezzz!"

"Well, trust me, honey," She said with a laugh as she rose to leave. "You really would, and I don't not being cruel when I say that either. After all, can't some boys be cute, or pretty? And tonight, you have become my pretty little son now, and you are becoming even prettier every day, aren't you?"

"Ah, gee whiz, Mother," Michael said, sinking his head into his pillow while tucking his knees under his stomach, unknowingly raising his cute, sexy ass high in the air. "Please, no more? Okay?"

"Okay, little darling," she said, patting and squeezing his butt for a short time before she walked from his room, closing his door. "Sweet dreams, precious one."could be heard from down the hall.

Finally, glad to be alone in his room at last, Michael turned over onto his back once more, raised his new and even more sensuous nightie up to his tits and began once again to pull his panties down to mid-thigh. Michael realized with slight amazement that he had enjoyed his Mother's teasing a little and didn't mind her insistence that he was becoming even more girlish with each passing moment, but he was really desperate to get himself off and was glad she'd finally left.

He quickly pulled a sock over his fairly rigid cock and began stroking it rhythmically with his right hand. Then with his left he started fondling his rapidly growing breasts through the lace bordered bodice of the silk baby-doll nightie, so transparent that he could see the greatly enlarged size of his nipples showing through. Pinching and pulling at them greatly increased the sexual pleasures he was feeling. The increased intensity of those pleasures pushed him into his second and most powerful orgasm of the day.

Thinking back to each of the items of apparel her son was made to put on and judging from his reactions after getting them on, Mary knew her son would soon be hooked on these new feminine feelings and desires. With a few careful nudges and well-timed prods from herself and Melissa, they would soon make Michael understand and accept this fact.

Satisfied that her son would in his feminine sleepwear and that he would soon be hopelessly lost in a world of feminine pleasures, Mary returned to watch the last of the news.

Michael now lay in bed getting ready to drift off to sleep when he realized he needed to pee and pee badly. So off to the bathroom he went, and for the first time since he was a child, Michael sat down to pee. The realization of what he'd just done didn't hit him until he'd gotten back in bed and then all it did was muddle his thoughts a bit more then they already were, as the boy, once back in bed, fell asleep while mindlessly fondling his ever-growing tits through the gloriously soft and. luxuriously feeling clothes in which he was delightfully enmeshed. Ah, the dreams of that night...

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AnonymousAnonymous9 months ago

I know porn isn't required to be textbook accurate and there's certainly nothing unprecedented about characters behaving like sociopaths and disregarding normal standards of consent and "decency" but some of what's stated in this story is just plain ignorant and harmful misinformation.

I get that cartoonish stereotypes can make erotic material more charged because they make liars out of the part of our psyche that wants everything polite and nice. The dumb bimbo, the clueless and oafish American male, the thug, the various types of nymphomaniac grouped according to ethnicity, there will always be places for these cartoons just as dirty jokes and junk food will always find their niche.

But when a character says thoroughly ignorant things and the implication is that they've done their research, readers forget to apply the same grains of salt they would hopefully apply to the snake-oil pitches of Dr. Oz or Goopeth Paltrow.

Just a brief summary: transvestite is someone who deliberately dresses like a woman and doesn't identify as such; transgender is not a "lifestyle"; hormones don't feminize adult or adolescent brains; progesterone is not the primary hormonal medication for anyone seeking to transition; feminization as a fetish is completely unrelated to being transgender; care providers do not get off on manipulating people into transitioning; and even if it were possible to brainwash someone into thinking they're trans, you'd need multiple conditioning techniques as people's brains and psyches aren't that pliable and you would likely need to isolate them both to control their environment and to negate the possibility of interventions from concerned acquaintances.

Also, transitioning would no more cure toxic masculinity or anti-social personality disorder than increasing one's melanin count would cure racism or make someone's dick grow. People who respond well to hormone treatments are most likely already primed to accept it at a neurological level. The likely outcome of this little stunt would be for Michael to violently lash out at his mother and sister. It may not be the erotic climax you've envisioned, but the likelihood that a male who feels emasculated will attempt sexual assault is very real.

It would have been less harmful if you'd relied on brainwashing techniques or just made up ridiculous magical pills or some other clearly fantastic method just to avoid giving the impression that this story bears any resemblance to real life transitioning.

It's worth bearing in mind that trans people don't feel like they're changing so much as assuming the identity they've always had. If you wanted to "turn" someone trans, you'd need to target them in the womb.

dreamer31adreamer31aabout 1 year ago

i am sure you could produce another page im so hard now

thanks

AnonymousAnonymousover 1 year ago

Really awful. Not well thought out and the writing was terrible. More like a comic than a story.

AnonymousAnonymousalmost 5 years ago
jerk off

i want be a gril so bad i will pay any thing to have a pair of tits and dress like a woman. this story want me cut my own privite parts off just to satisfy my mind i want to be a gril now not later.1UK8D9

AnonymousAnonymousover 7 years ago
Need Suggestions

I felt very horny anf even inspirational..I am a boy and some times wanted to become a girl,but i do like being a boy.I love women and f***** them.Can you please tell me what to do.

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