tagTranssexuals & CrossdressersOur Steven, Our Stephanie Ch. 01

Our Steven, Our Stephanie Ch. 01


This is the start of my second submission here on Literotica, or anywhere else, for that matter. I am pleased with the positive response I received for the first story, and I only hope you all enjoy this story as much.


Steven had just gotten home from school, hanging his coat up on the coat rack when his Mother had turned into the hallway coming up from the basement and, turning to go upstairs, bumped into him while carrying a load of washed and folded clothes in the laundry basket.

"Oh, sorry, dear," Vanessa said, a bit startled. "I didn't see you there. You just getting back? How was your day, honey?"

"Uh, that's OK, Mom, my fault really. I guess I should have made more noise." Steven answered. "And yeah, I just got in. School was good, got a B+ on the Math test I took on Wednesday. How was your day?"

"Ugh," She said. "Busy! I started spring cleaning today and I haven't had a break yet. Now that your back, can you give me a hand putting these clothes away? I have something I need to talk to you about anyway, a favor I need to ask of you."

"Sure, Mom," he said, while a worried crease burrowed across his brow, wondering what she could be wanting from him. "I've only got a small amount of homework to do tonight so I have plenty of time to give you. Why don't you let me take that basket upstairs for you?"

"Thank you, dear," she said. "It' all your sister's things, so bring the basket to her room. And before we start and I forget, let me say first how proud I am of you about your test score. I know how hard you studied for that test and how difficult a subject math is for you, so know truly how proud I am of you."

Unused to such high praise, Steven was blushing profusely when he said, "Gee, thanks, Mom."

"And don't think I didn't mean every word of it," She added. "Because I did." When they both reached Diane's room, she continued, "Put the basket on the bed and I'll hand you her clothes and you place the items in her dresser or hang them in her closet, OK?"

"Aye, aye, Capitan," Steven replied with a giggle and a mock salute.

As Vanessa was about to hand Steven a blouse to hang up, she noticed the disarray of his nails.

"Oh no, oh no, that will never do," She said despairingly, eyeing them closely. "If you try to handle anything here of your sister's with those hands, you are surely going to snag them on these ragged nails you have. We must do something about them at once."

"But Mom..." Steven started.

"No buts, sonny," Vanessa interrupted. Then, taking his hand, she said, "Come with me." Soon Steve found himself pulled into the pink flowery sweet smelling confines of his Mother's bedroom, seated at her vanity table.

"OK, let's see," she said, looking about the table. "Ah yes, this is what we need."

So saying, she picked up an emery board and started filing the boy's nails. While performing this task, she told him the reason for this.

"At least you don't bite your nails. However, in the future you must do a better job keeping them neat and presentable, especially when caring for delicate undies and lingerie.

"A good thing to keep in mind also - it's always better to file rather than clip your nails, because you get a more harmonious outcome with a file. If you break a nail, you can clip off the broken end, but then file the remaining nail down smooth.

"Also, filing the nails into smooth ovals instead of square edges like most men do will cut down on the risk of catching the edge of your nails on delicate materials or worse, of catching the edge on something hard and chipping or breaking them."

As Steven sat through this ordeal, watching his hands become more and more feminine, the words his Mother spoke strangely seemed to make sense to him, in a twisted sort of way, if you didn't look too hard for the logic to it. However, when she started to put nail polish on them, he pulled up very tense.

"Mom-" the frightened boy started.

"Don't worry, dear," Vanessa said reassuringly. "This is just a nail hardener to protect your nails. It's clear -- see? No color at all. No one will even know you have it on.

It's also nice to see how you've managed to keep your hands so soft and silky smooth. Not hard and calloused like most boys your age. It's probably from all the swimming you do for the school.

"But you know, with all the harsh chemicals in the chlorinated water that you spend so much time in, you really must watch out for the effects they can have on your skin."

So saying, she took a bottle of hand-lotion and squirted a dollop into his palm and began massaging it into his soft, silky skin.

Then she had him do the same to his other hand and then gave him the bottle of lotion and nail hardener to take to his room, telling him to be sure to perform the hand care maintenance routine she showed him on a daily basis.

In a daze, he followed her as she led him first back to his room to drop his new toiletries off and then to his sister's room to finish sorting her laundry.

As Vanessa handed Steven a pair of Diane's panties to place in her dresser drawer, she asked, "Doesn't the material of those panties feel so lovely, Steven? I could just imagine how you boys would feel if your underwear was made with that kind of sensuous material, eh honey? You boys would probably swap all your coarse, drab things for underwear like this in a flash, I dare say, right dear?"

"Damn, Mom," Steven said, amazed at the boldness of such a question and the strength of his response. "That's an embarrassing thing to ask a boy, really!"

"Oh, it is not, now," she challenged. "It's just a question about comfort and sensuality asked between family members in the privacy of their own home. Come on, no one will know what we say here. Go ahead, tell me. Don't you think your friends would jump at the chance to wear something as sensuous as the underwear your sister wears if they made it for boys in the same material?"

"Mom! You are really a pip," Steven said. "All right, then. You swear this doesn't leave this room?"

"Yes, darling, I swear," she affirmed.

"Well, I can't answer for the other guys," Steven answered almost conspiratorially, "but I think if they made boys underwear in this material, I would wear them all the time. Shit, I can't believe I just said that to my own Mother, but you swore not to tell any one I said that, right?"

"Right, dear," she again affirmed. "But that brings us now to the favor I wanted to ask of you."

"Oh, I had forgotten about that," Steven said.

"Yes, well," Vanessa said, "You see, since your Father died, we've all been trying hard to make ends meet, and I want to thank you and your sister for doing your part in helping us get through these tough times and for not complaining when you couldn't get the faddish things that your friends come by so easily.

Our finances have been pretty much strapped lately, but both of you have behaved so responsibly you don't realize how proud you've made me, how proud your Father would have been of both of you. Now however, I have to ask you to make another sacrifice for the good of the family."

Having been so humbled by her praise of his and his sister's actions of late, Steven was near to tears when he replied, "Gee, mom, if it's for the good of the family, whatever I can do to help, I will."

"Honey," she started. "I need you to start wearing your sister's hand-me-downs for awhile. Diane has outgrown many of her things and since she is only slightly taller than you, those things she has outgrown should fit you nicely..."

"But Mom..."

"No buts, dear," Vanessa made clear. "And don't worry dear, not all of her clothes. Not her dresses or slips and stuff. But her jeans and boyish slacks, and you said you'd love wearing her underwear.

"So I don't see any reason why you couldn't wear her undies, T-shirts, blouses, socks, anything that's not really girlish, that's all. After all, pants are pants, aren't they, and whose going to look under your clothes to see what your wearing beneath them?"

"But...but Mom," Steven squealed in a high-pitched voice. "How can you ask me, your son, to dress up in Diane's clothes? I mean, It's...It's...sick! It's perverted!

If any of the guys found out, I'd be the laughing stock of the neighborhood, the school! You can't ask me to do such a thing, because I can't, I just can't. It's so embarrassing to even think of. Aaauughh!"

At that Steven ran from his Sister's room. As Vanessa watched his hasty departure, she smiled as she saw how swishy he ran through the door, so much like a sissy girl.

Yes, she thought, the hormones she'd been giving him for the past three months, telling him they were vitamins, were starting to work on his body as well as his mind, and she was pleased with his slow but steady progress into womanhood.

Already he was developing small nascent breasts which, so far, he hadn't noticed yet. But she had, and was dying for the day to arrive when they blossomed forth into B or C cups.

Yes, she may have told Steven that pants were all she had in mind for him, but it was a blatant lie. As soon as she could, she would have him in dresses, nylons, garters, bras, panties, high heels, girdles and/or corsets, and makeup.

She would have to get Diane involved now in the further development of Stephanie. She knew the dear girl would be thrilled.

It wasn't that Steven was a bad boy. Indeed, he was as good a boy as Vanessa had made him out to be -- a hard worker, a good student, always friendly, polite, and never any trouble.

But the course Vanessa was mapping out for Steven to follow, the path she was choosing for him to walk, though strange and highly unusual for most boys - many might think perhaps even cruel - she truly believed in her heart was actually quite the opposite of anything close to approaching cruel or wrathful.

Okay, yes, she was trying to turn her son into a second daughter, and yes, she was going to make sure there was fun to be had while going through the process of transforming Steven into Stephanie. She felt, however, that her reasoning had merit.

For, in addition to a deep, dark secret which she shared at this time only with her daughter Diane, Steven's 18 year-old fraternal twin and which was the primary reason for Vanessa's decision to take her son down this path, she also held a deep and endearing belief in both her heart and her mind, that she truly felt she was doing her boy the biggest favor of his life by doing this to him.

This decision came about because she, as well as anyone who saw him, recognized that Steven was a small, delicately featured boy who, because of his girlish features, would not make it far as a man in this world of manly men.

And although Vanessa hadn't noticed any feminine tendencies in Steven before she had taken it upon herself to start this metamorphosis, she still worried about him, that they would eventually take him over.

Thus she decided that it would be better for him to be a boyish girl than a girlish boy, if he had to be one or the other. Thus, for his own good, and because it pleasured her to do so, she planned his metamorphosis into womanhood.

to be continued...

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byJohnboy9© 14 comments/ 173418 views/ 53 favorites
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by Anonymous

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by Anonymous09/04/17

Wished it were me!!

I dreamed of becoming feminine! I prayed that I would wake up a girl.

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