Our Steven, Our Stephanie Ch. 05

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Steven begins his journey to become Stephanie.
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Part 5 of the 10 part series

Updated 10/30/2022
Created 10/20/2009
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Johnboy9
Johnboy9
434 Followers

This is the fifth installment of the "Our Steven, Our Stephanie" series, and I wish to give my thanks once again to the continued support and great feedback I have received for the chapters I have written and submitted thus far. You people out there have made it a joy to write for this site [as well as provided many great stories for me to have read on my off time :-)]and I hope you continue to enjoy this particular read.

*

Immediately upon hearing the second of the two commands, Steven's mind, though still in the trance, was once more dominated by his male persona, though now with the still-born desires for the girl's clothing. As such, he was at once shocked at what he was wearing and could not understand how he had gotten them on.

"What the hell?" He started. "How the hell did this happen? Where did these clothes come from, and why am I wearing them?" Then, seeing all the girls sitting around him and giggling at him, he blushed a beet red down to the roots of his California blond hair. "Oh God, this is so embarrassing."

"Steven," Diane interjected. "What's wrong? Is something the matter?"

"Well, duh!" he said, as though it was completely obvious. "These clothes! What am I doing in them?"

"Well duh, yourself!" she snapped back. "Don't you remember? You asked me if you could wear some of my nice things instead of your stupid old boys clothes. Said you never wanted to wear boy's clothes again.

"Why, is there something wrong with those clothes I gave you? You said you liked them, and we all think you look very nice in them. They are very pretty on you."

"Well jeez, Diane," Steven started. "Of course they're nice. I don't mean to say otherwise. That's not the point, though. I mean, these are girl's clothes, and I'm a boy, and boy's don't..."

"Don't what, Steven," Diane interrupted. "Don't wear girls clothes? What? Don't they feel nice? Don't they feel good on you, soft and silky and light and sensuous? Don't you feel good now that you're wearing them?

"Just because you're a boy, who says you can't you wear something that feels nice against your skin, eh?"

"Well gee, Diane," Steven moaned in reluctant agreement. "Yeah, I guess they do feel kind of nice and soft and silky, and yeah, I do feel nice wearing them like this. But still they're for girls and I'm a boy. I shouldn't be wearing them."

"Well gee whiz, Steven," Diane said contemptibly, angered now at the constant lip he was giving her. "If you dislike them that much, quit complaining about them and take them off. Change back into your own clothes and stop bothering me, see what I care!

"It's a free country, after all. No one says you have to wear those clothes, even though you like the comfortable feeling they give you. We're not forcing you to wear them, only suggesting that you might prefer them. But don't be coming back here asking me for more clothes if you change your mind again.

"In fact, don't be bothering me about anything now. I'm very upset with you. Go away, change back into your horrid boys clothes and leave me and my friends alone, because if you ever bother me again tonight, I'll take you over my knee and give you the spanking of your life, so help me!"

At that Steve left disconsolately to go back to his room and started to take off the offending garments, but suddenly found he couldn't. He began to fondle the silky, satiny material, caressing it softly, suddenly finding too great a fondness for the material and its feel against his skin.

Suddenly realizing what he was doing, he immediately stopped, angry at his actions and looking around guiltily to see if anyone had noticed.

He was still unable to stop feeling those sexy sensations and the longer he continued feeling them the more guilty he felt and angry he was at himself because he knew he was a boy and boys shouldn't be feeling or thinking the way he was about the clothes he had on right now.

Yet they felt so good it was as if he was now unable to remove the girl's clothing, as much as he felt he wanted to.

All of this fretful wondering only combined to make him feel more and more guilty each additional time he tried and failed to remove the sensual but offending feminine garment. The more he tried, the more he failed, and each failed attempt caused him to feel even more like such a waste as a human being, as a man.

He truly needed to be punished, severely punished, and he could only think of one person who might be able to accomplish that task. Realizing there was no other option, and wishing to rid himself of this terrible guilt he felt, he shamefully left his room approached his sister's, his head hanging low.

"Diane," he started, after arriving at her doorway. "I can't take off my clothes even though I know I should. The trouble is they feel too good and sexy on me, and make me feel well, girlish, I guess. And, even though I know I shouldn't, I like the feeling.

"So I'm all mixed up inside and feeling all guilty and everything. So I was wondering if you'd take me over your knee and spank me really hard, first on my panties, and then with my panties lowered?"

"Well, Steven", Diane answered. "I can see your problem, I guess. I mean, I don't know why you just can't accept those beautiful clothes as the gift they were intended to be.

"Even you like them and agree they're nice to wear, but, what the heck -- that's water under the bridge, I suppose. Since you can't accept them like that without feeling guilty about it, well, of course I'll help you deal with your guilt, and in the way you suggested.

"I'll help you out even moreso, so that these strange deviant dress-up issues of yours may hopefully be dealt with more permanently. I'll get my crew here to help with your punishment so that it will be really severe and becomes a punishment you'll not forget for a long time to come.

"That way, in the future, you won't find yourself dressed up in clothes you don't seem to want to wear, yet can't seem to want to change out of, okay?"

"Gulp." Steven swallowed hard, beginning to wonder if he'd chosen wisely. Finally, accepting there was no alternative, he braced for the worst and continued, "Well, if you think it best, I suppose then."

"Good, good," Diane continued. "Here's what I propose, then. Because your guilt is so horrendous and your need for punishment so obvious, I propose that each of the four of us girls take turns giving you 10 swats apiece on your pantied ass.

"When that round of spanking is finished, you will remove your panties and then I will finish off by giving you 15 more swats on your naked backside. What do you girls think?"

"Yes, yes, we agree. We agree wholeheartedly." The girls chortled happily. Steven could only groan in anticipation of what he reluctantly came to accept was something he deservedly needed.

Diane then pulled the chair from her vanity table and placed it in the middle of her room facing the bed where her girlfriends were sitting and sat down in it.

Then she had her girlfriends sit on the edge of the bed in a row facing her, so that they would have a grand view of the proceedings and so that the next girl in the row would be ready to take her place on the chair when she was done, then so on down the line. She then motioned for Steven to come to her and lay down over her lap.

Steven's face was chalk-white after listening to Diane's pronouncement of what his punishment was going to be. He'd had no idea that she could be such a harsh disciplinarian.

And he saw in her eyes that she relished the power she held over him, and especially so because she'd both gotten him to ask her for it and because he was allowing it.

Yes, he realized, she was going to be loving this moment as she gave him these spankings. And he imagined that if that was the case, then the rest of the girls were probably of like mind. Therefore, he was definitely starting to get very frightened thoughts about this as he hesitated laying over Diane's lap.

"If you don't come here right now, Steven, your punishment will be even more severe." Diane promised.

Finally, though, he realized he really had no alternative. For some reason he was wearing girl's clothing which he had to get out of at all costs. Yet for some reason he was unable to do so, no matter how hard he tried.

Diane said she could help, but because he had upset her with his bad temper and foul mouth, she wouldn't until he was satisfactorily punished. He knew he was in the wrong, and especially so because he had asked to wear her clothes and then turned around and told her he didn't want to wear them, no, couldn't wear them.

As nice as they were, and even though he wanted them, as a boy, he knew he couldn't wear such things. And acting in such a way, he'd hurt Diane badly.

For that reason, and because he wasn't man enough to remove the feminine garments himself, he knew he needed to be punished, and needed to be willing to accept it, needed to at least be man enough to accept his punishment, especially if it would help get him out of these offending garments.

Thus, being so thoroughly confused and bewildered, Steven stepped up to Diane and lay across her lap. Diane raised his slip, nightie and peignoir above his panties to his waist and held it there with her left hand. She then raised her right hand high in the air and brought it down hard with a vicious sounding CRACK! At the first spank, Steven winced with the pain it brought him, especially as it shoved the butt plug deeper into his anal passageway. Still he was able to take it without complaint. It told him, however, that if the number of spanks yet to come were as hard as this first one, then his ability to withstand his remaining punishment without embarrassing himself in front of his sister and her friends was going to be sorely tested.

Again, SMACK!, as Diane brought her hand down a second time. Then SMACK! CRACK! CRACK! Came three spanks in rapid succession and by then Steven was writhing about in his sister's lap, moaning in pain.

The movement of the butt plug might have made the ordeal pleasurable had it not been for all the other surrounding pain. SMACK! SMACK! CRACK! SMACK! CRACK! The last of his first 10 spanks were delivered in a rapid tattoo on the poor boy's upturned bottom. By now Steven had begun to cry and was begging for Diane to stop.

"Please (sob), stop, Diane" he choked out. "That's enough, isn't it? (sob, sob)."

"You're right, Stevie," Diane said. "That was quite enough, at least from me. Now it's time for your darling Sarah to take my place for the next ten. Don't worry about it, Stevie. We all know that this punishment is for your own good, right? That is why you asked for it, isn't it? Well, tell us, isn't it?"

"Yes (sob), you're right, Diane," Steven said, even more choked up at having to admit to wanting more of this. "I do need this punishment and I did ask for it. Please girls, (sob), give me more. I need it, I want it."

"I'm glad to see you've finally come to your senses, Stevie," Diane replied. "I'd hate to be accused of abusing you physically sometime down the line when we all knew this was what you always wanted and needed. Okay, Stevie, up you go, and Sarah, you take you're seat here. Now Stevie, you lie down over Sarah's lap for your next 10."

Humiliated, yet knowing it was for his own good, Steven did as he was told and lay down on Sarah's lap. He hoped she would be lenient with him because of his secret love for her. He had no idea however, that this love he felt for Sarah was in no way reciprocated.

Even though the young lady was aware of his feelings toward her, he had never openly expressed them and she would have turned him down if he had. She was more into the bigger jocks at school, the football and basketball players.

She found Steven rather wimpish, even on a good day, though he was fun to tease and string along. She so loved to have him wrapped around her little finger.

Sarah looked down at the feminized boy, and you could almost see her salivating at the sight of his willing helplessness. She had two older brothers at home and they made her life miserable.

Being in control of her best friend's brother like this, having the chance to wallop him good even if for no good reason, gave her a sense of power and authority over him that she could never feel at home over her brothers.

It also gave rise to a number of delicious fantasies that she'd hardly ever before dared dreamed to imagine, and at the same moment, it provided her the chance to act upon those fantasies, which she was about to do - with a vengeance.

CRACK! WHACK! SLAP! SWAT! CRACK! The first five spanks rained down on Steven's rear-end in a furious rapid non-stop beat.

Steven was crying hard now, believing that if his sweetheart felt this strongly about disciplining him this severely, then he truly must be deserving the punishment he was getting for not being able to remove his lovely yet hated girl's clothes.

Even moreso, he knew that even though the punishment was so painful, he would need to have to receive even more, he was that bad. He hardly believed it was his voice, but suddenly he heard himself telling Sarah,

"Thank you (sob) for (sob) spanking me, Sarah. I know I needed it (sob). Please give me the rest (sob) that I have coming."

"Well, I'll tell you, Stevie," Sarah started. "That was very good of you to ask so nicely. But I won't continue until you ask me to keep going and say 'Pretty please with sugar on top'. Now say it, dearie."

"Sarah, (sob)," Steven started. "Please keep spanking me. Pretty please with sugar on top?"

"Why of course, dear" Sarah answered. "If you want it that badly, how can I refuse?"

CRACK! WHACK! SLAP! SWAT! CRACK! Sarah laid the last of her 10 spanks down as hard as she could on Steven's pantied ass, and just as she finished with the last blow, she came hard, nearly passing out from the enjoyment of inflicting such pain on Diane's hapless brother while imagining it was one of her own brother's, taking the beating.

Once she caught her breath, Sarah raised herself up and said, "Okay, Julie, you're up. Take your turn with the sissy-boy here."

Julie then took her place on the seat vacated by Sarah and forced the weeping Steven onto her lap. She had felt sorry for the boy as she watched him get ruthlessly manhandled by his sister and then again by Sarah.

She had planned to take it a bit easier on him until the moment he lay across her lap and suddenly she was hit with the same feelings of revenge that had hit Sarah. Julie, however, had no older brothers who mistreated her.

In fact, her only sibling was her twin sister, Elaine, with whom she had no real difficulties. What she did have, however, was a boyfriend who had recently dumped her for a new girl to the school and she had not yet gotten over his mistreatment of her on that point.

Now, with the sissified Steven over her lap like this, all those sympathetic feelings Julie had felt for him as she watched him get his spankings flew out the window when she remembered what her ex-boyfriend had done to her, and just how miserably he had treated her.

CRACK! WHACK! "You know you deserve this, right Steven?" SLAP! SWAT! "You know these spankings you're getting tonight hurts all of us girls here more than it does you. Right, Stevie? Because we don't really like to beat on you, Stevie.

"You know we really like you, so this is very painful for us when we have to use these corrective measures on you. But you must realize, don't you, that you do deserve this punishment?" CRACK! "Isn't that right, dear boy?" SPLAT! WHACK!

"Yes, Julie, (sob) I was bad (sob) and I deserve my (sob) punishment. I (sob, sob) know this." Steven replied brokenly.

WHACK! "Good sissy-boy." CRACK! "I'm glad you know this now." SLAP! Julie spanked the poor, sobbing boy as hard as she could, giving him all ten spanks with no break.

"Your turn now, Elaine."

Julie's twin sister, Elaine, now took her place on the "spanking chair", and took Steven over her lap. She was absolutely breathless in her desire to start, and was picturing him in diapers instead of girl's clothes. Maybe after this, if she could get him alone, she thought with a mischievous twinkle in her eye.

And with that thought, she had an inspiration. Remembering what Diane had done when she was dressing Steven, Julie reached into Steven's panties and pulled out his butt plug and smeared it on his clenched lips.

At the same time, she pinched his nose shut using the index finger and thumb of her other hand until he was forced to open his mouth to breathe, or suffocate. Triumphantly, she jeeringly pushed the plug into his mouth.

"Here, Stevie, suck on this while I spank you," Elaine told him. "Maybe it will take your mind off the pain."

Then CRACK! SPLAT! WHACK! "Poor wittle Stevie. Did the big, bad girl hurt you? Hmmm?" WHACK! SLAP! SWAT!

"Oh Stevie, you're not going to let the wittle, bittie girl beat up on the big, stwong boy, are you? What would all your fwends say if they knew that a wittle bittie girl spanked a big, stwong boy like you and made you cwy? What would they say, Stevie?" CRACK! SPLAT! WHACK! SWAT! "Tell me, what would they say!!??"

"Oh, oh, (sob, sob) Elaine," Steven chokingly began. "They would call me (sob) thithy-boy, (sob, sob), and queer bait, and puthy boy, (sob) and girly boy, and thithy-pantth, and, and...(sob)"

Hearing Steven lisp just like a little kid because of the butt plug in his mouth had all the girls rolling on the floor in laughter, laughing so hard they had tears in their eyes, especially hearing the childish way Elaine was talking to him.

Finally regaining her composure, Elaine continued, "There, there, sissy-pants. I get the general idea. It wouldn't be a pleasant experience for you, would it?"

"No, Elaine, it wouldn't."

"Then we'll just have to make sure we don't tell anybody, won't we. If you keep doing as we tell you here, then I don't think anybody else should need to find out, do you?"

"No, Elaine."

"Good, I don't think so either," Elaine replied. "Now it's time to conclude your punishment. You must now remove your panties and lie down over Diane's lap for the last of your spankings."

His ass still burning painfully, Steven, still sucking on his butt plug, carefully removed his panties, trying to keep them from rubbing against his deeply reddened and swollen cheeks. The he slowly lowered himself down over Diane's lap.

Diane had earlier stepped out of the room for a short time to gather a couple of things she'd picked up for the night and then returned to finish up Steven's punishment.

"It's nice to have you back again, Steven," Diane said. "My, my, your little butt cheeks here have certainly taken on a deep shade of red there, haven't they? If we all didn't know better, we might even think you'd been doing some nude suntanning. Of course, we do know better, don't we, girls?

"I just want to say how proud I am of how well you have taken your punishment, dear. You have been a good girl and done very well here. Now I'm just going to finish up here with the last of your spankings, and then we will be finished, okay?"

"Okay, Diane," Steven choked out.

At that, Diane slowly raised his slip, nightie and peignoir to his waist, exposing his bare bottom, and held them there with her left hand. She then raised her right hand high in the air and and brought it down hard with a vicious sounding CRACK!

Again, SMACK!, as Diane brought her hand down a second time. Then SMACK! CRACK! CRACK! Came three spanks in rapid succession and by then Steven was writhing about in his sister's lap, moaning in pain.

Diane noticed quite a difference in the feeling between the first spanks on his panties and these now on his bare bottom, and really enjoyed the sensation of flesh against flesh much more than the earlier flesh against cloth spankings.

Johnboy9
Johnboy9
434 Followers
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