A Sister's Revenge Ch. 05

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Michael gets a new look - a totally new look!
11.6k words
4.53
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Part 5 of the 7 part series

Updated 10/21/2022
Created 01/29/2010
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Johnboy9
Johnboy9
434 Followers

Here, finally, at the request of many of my readers out there, is Chapter 5 of this continuing saga of Michael's descent (ascent?) into womanhood begun by his sister, followed by his Mother, and now continued by a friend(?) Cindy.

I am sorry for having taken so very long to get back to this, but I was at such a loss as to how to continue. I was really angry at myself for having Michael faint at the end of chapter 4, because I could not, for the life of me, think of a way to get back from that situation and continue onward. I thought if only I'd ended it the moment Cindy had exposed herself, and begun here with Michael's response, it might have been much easier, but it was too late. Finally, I had an epiphany, and just recently have been able to come up with this continuation. I hope you all enjoy it.

Please note, this is a longer story than I normally write, and there is not really any sex here to speak of. Its sort of a realization of where Michael and Cindy stand, sort of. Its also sort of a build up of things to come. Lets just hope I don't take so long to get to the next chapter to finish the build up.

Please, 18 years and older. Thanks.

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"Besides," Cindy pointed out. "I wanted you dressed like that for a special reason. Do you want to see?"

"Uh, uh, sure," Michael said, although he was pretty sure he wasn't so sure.

"Come closer, little one," Cindy said. "Come sit here beside me."

Michael walked hesitantly over to the bed and sat on the side of it next to Cindy, who was lying in the middle of it, atop the blankets. When he was seated, Cindy began to gently, softly caress and stroke Michael's slowly hardening cock.

"Michelle," Cindy started. "Lift up my nightie, would you?"

"I'm sorry," he asked, wondering if he might possibly have heard wrong.

"I asked if you'd please, missy," she repeated. "Raise up my nightie, like a good girl?"

A bit hesitantly, though still hoping for some more fun and games, Michael did as Cindy asked.

Slowly, unerringly raising the hem of her nightgown, as though unveiling a masterpiece of famous artwork, Michael finally revealed what hidden treasures lay beneath.

"This, Michelle," Cindy said to a gawking Michael. "Is my gift to you."

"Oh my fucking god," Michael groaned, and then, immediately after spurting a stream of cum into Cindy's hand, fainted away at the mouth-watering sight of Cindy's 12 inch strap-on dildo that she allowed to pop up from between her legs.

"Well now," Cindy pondered, looking over Michael's prone, lifeless body. "I definitely wasn't expecting that."

Ch. 6

Unsure what to do, Cindy removed the strap-on and waited for about 2 or 3 minutes. When the boy did not awaken, Cindy began to worry some.

Then she got a wickedly devious plan that she thought the two would enjoy, or at least she hoped he would, because she was definitely going to have great fun with it.

Taking the dildo in hand, Cindy rubbed it gently against her damp pussy to try to get it even more wet with her juices of excited desire. When she had it at the right slickness and when she was shaking with readiness, she inserted it inside her cunt and moved it in and out about 6-7 times, until it was totally saturated. At that point she placed it just below Michael's nose, and slightly above his mouth.

Michael, in his deep oblivious and unsuspecting unconscious state, became suddenly aware of a familiar scent, a smell he'd come to truly love and enjoy, and one that he related to a female's cunt. Unconsciously, he stuck out his tongue and began licking the air, at least it was the air until Cindy lowered the tip of the dildo downward until it touched the searching organ, and when it did, it became like food to a starving man!

Cindy had to force herself to keep from laughing at the sight of this still unconscious boy who, out of purely reflexive and instinctive actions, began searching out and devouring the cunt juices off of that 12 inch dildo that had earlier so frightened the boy into a state of total unawareness.

Feeling it was time to up the ante, Cindy began to slowly, gently, push the dildo into Michael's mouth directly. Amazingly, she was able to thrust it gently in and out as Michael still seemed to have some truly baby-like need for this toy, as though it had become some sort of life-saving pacifier to him to get him out of the nether world into which he'd been thrust.

Cindy was pleasantly surprised that Michael was able to take the dildo into his mouth like he was doing, even slightly into his throat without choking and with no apparent difficulty at that, for it was about 1½ inches larger around this his own, and definitely not as malleable. Growing more worried of this however, she decided to try one more thing to wake Michael up. If that didn't work then she was really going to have to perhaps call an ambulance or something.

This time, once Cindy thrust the dildo about 5 inches into the boy's greedy mouth, she left it there, slowly closing off his breathing. To add to this, she also pinched his nose shut to completely shut it down. "Now let's see what happens," Cindy thought to herself.

Suddenly, with a cough and a sputter, Michael woke up and spit the dildo from his mouth. "Shit, Cindy," he shouted, though it sounded a bit funny because it came from a wide open larynx while it was slowly closing up. "What the fuck are you trying to do? Suffocate me? "

Cindy couldn't help laughing at the red-faced boy with spit and her cunt juices all over his face. She couldn't stop laughing and actually fell to the floor still holding her belly.

Slowly, forcing herself to regain her composure, because she knew the boy was embarrassed, she got up and back on the bed next to Michael, and tried to soothe him.

"Oh, oh oh...I'm so sorry, Michael," she said chokingly, still trying to calm down. "I didn't mean to laugh, really I didn't. I just couldn't help it. You were such a sight, that's all.

"Here," she said, bringing a hand-held mirror to his face, showing him the sloppy mixture of saliva and cunt juices that had by now begun to dry up around his lips and nose. "See what I mean. But really, believe me, I wasn't laughing at you, it was just the situation that was so funny. Please forgive me, won't you? Besides, I think I'm really laughing because I am so relieved that you're alright, because you've been unconscious for such a long time I was worried I'd have to bring you to the hospital to see if you were okay."

"Well..." Michael said pensively, while studying his reflection in the mirror. "Aw, fuck it!" he added, and then started giggling uncontrollably himself. "God, I am a sight, aren't I? And I am sorry for worrying you like I did, but hell, that dildo is massive, and you wanted to use it on me? On me, for goodness sakes!"

"Oh missy," Cindy decried his complaint with bemused scorn. "You already took 3 of my fingers into that oh-so-precious bum-hole of yours, so I know that that invasion opened you up more than 2 inches at least, and you loved every minute of it. And while you were unconscious, that mouth of yours sucked my baby here down like a pro and you enjoyed that as well. And you took at least 7 inches with no forcing or anything. So don't give me this 'Oh, oh its too, too big for little ol' me and my tiny, tender, precious holes!'. I know the truth about you baby, and the truth is you love the sex we have together, and I wouldn't have it any other way! And if I can get you hooked on this big daddy here, I know you'll start loving to have sex with certain well hung guys I happen to be familiar with. What do you say to all that, sweet-cheeks?"

Michael was totally red now because, looking at his reflection, and remembering the great fun he'd had with the ass-play Cindy'd given him, he realized all Cindy said was true, and the evidence was plain as the juice stains on his face, and the still-tender feelings in his ass. All he could do was admit the truth of it all.

"Fuck, Cindy," he started, almost contritely. "I'm really sorry for blasting out like that. I mean, I really had no right, because you're right, really right about it all...I know it now. Its just that its been so overwhelming and all, this sex bit, you know? I mean, I'm so used to getting yelled at and spanked and tormented that all this is really new to me, and it just so suddenly came upon me that to have it all and admit I love it and want it and even more of it, is sometimes something I don't expect to be allowed to have. Its just such a shock, I guess."

"I'm sorry as well, Michelle," Cindy said. "I sometimes get too carried away with some things, and this was one of those times, unfortunately. Its just that you looked so delectable and tempting, lying there all innocent and stuff. I just couldn't help myself. And what made it even worse was the sexy, lusty way you responded to my gropings and molestations. It is simply impossible to remember that you are so new to all this, and that I need to take my time bringing you along."

"Well, Cindy," Michael said. "I guess there's really nothing wrong with the way you sort of push me into things unexpectedly like you do. At least you do it with a loving kindness toward me rather than any sort of cruel intentions. And anyway if you hadn't played those sorts of games with me, how would I ever know if I'd have liked them or not? They would have gone by completely untried as I wouldn't have had the imagination or the guts to think to try them out on my own."

"Okay then, little girl of mine," Cindy replied, giving Michael a truly welcoming, affectionate hug. "Why don't we try it out this way. I'll work hard not to go too fast to soon, but if I slip up sometimes, why don't we create a safe word? Then if you are really scared of where we're going, all you have to do is say that word and I'll stop right then and there, no matter what. What do you think, eh, Michelle?"

"I think that's a great idea, Cindy," Michael answered. "What word should we use?"

"Well," Cindy started. "It should be something uncommon, not used in everyday conversation. Let's see...how about Transylvania. We haven't said that word yet today, and I don't plan on saying it in the near future myself, either. How about it?"

"Transylvania..." Michael pondered. "I like it. I like it a lot."

"Good, good," Cindy began.. "Now, my little girl, like we were about to do a couple hours ago," she continued, as she walked Michael into his bedroom, "I think its probably time for us to get some much needed sleep before it gets too late. We'll wake up nice and refreshed tomorrow, talk some more about your future and see what can be done about your home life, if anything."

As she tucked him lovingly under his luxurious, sumptuous feeling satin sheets, Cindy continued, "Maybe I'll give your Mother a call and see just what's up and what's been going on with her and your sister. If they refuse to change their ways, we may have to get the authorities involved, but I'm hoping it won't come to that. Like I said earlier, it may simply have been a power trip gone terribly awry, and things just may need to be put back into perspective.

"I'd also like you to think and ponder over this very carefully,,,I know you wanted to get rid of your really enlarged breasts that your family caused you to grow, and I truly understand and support your reasons if you decide to do so.

"However, now that you have seen the love a person can show you, the love you can actually feel from someone else who actually loves you *and* your big, sexy breasts, I would like you to think really hard again and decide if you want to maintain that desire, or if you actually don't mind having them so much, anymore.

"Any choice you make, I will support you 100%. Just remember, though. Without them, could you ever get these feelings again?" At that she pinched and pulled at the tips of his sensitive, ever responsive and gloriously hard nipples, giving him a salacious wink, then walking away.

Michael shivered happily underneath his blankets and realized that since he'd been at Cindy's home and in her loving embraces, he had not once recalled to mind his desire to get rid of his once hated tits. He still had to think about what she had said, though. After all, it just might happen that she would not always be in his life, and what if there was never found anyone else like her? What if everyone else after her treated him like his Mother and sister?

Yes indeed, it was something he must really think hard about. The thought weighed heavily on his mind that night, but luckily, the exhaustion garnered over the past 36 hours finally enveloped him and he fell into a deep, peaceful sleep. The first in quite a long time.

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The sun was streaming its golden rays across Michael's bed early that morning when suddenly there was a loud orchestral rendition sounding up of the old "Miss America" song playing somewhere that awoke Michael with a start. Out of the blue Cindy came marching in wearing a lovely blue satin robe over white satin pajamas, out from which projected this obscene massive 12-inch obelisk which was obviously attached to her waist.

'Oh no, here we go again,' Michael giggled to himself, hardly able to keep from laughing at such a sight.

She began strutting around the room in an exaggerated male stride, thrusting the dildo outwards with great pride. Then she began to sing out, "Here he is, Mister America, here he is, he's your ideal..." And with that she fell over laughing at the sight she knew she must be presenting, while at the same time, Michael finally broke down, and then couldn't stop laughing at the absurd vision of this girl with the 12-inch cock strutting around like some proud rooster who'd just finished laying out some 10 or 20 hens.

"Well," she said with a loving smile, when she finally stopped laughing. "At least you didn't faint this time."

And at that, Michael realized she was right. He saw that same life threatening dildo come prancing out like that, again attached to that same sexy body, and it never occurred to him to be terrified of it. It was just an inanimate object that was really something you could have fun with and play with. Maybe he would enjoy getting to know it better after all.

Michael wasn't aware of the fact he'd been watching Cindy with something like a gleam in his eyes, unconsciously licking his lips while concentrating his focus on the shamelessly obvious and apparently desirable rod extending so obscenely from her groin, a focus so intent that it could only be interpreted as a stare of lustful desire.

So intense was this stare and Michael's subsequent actions that Cindy noticed and began to grin with joyous intent. 'Yes,' she wondered, believing this might be just the right time and, taking a chance, slowly began to approach his bed. Then, suddenly changing her mind, she stopped and turned around going back to her room, realizing there were more important, immediate concerns they needed to take care of. This could wait until later.

"Okay, lover," Cindy said as she was exiting. "That's enough fun for the moment. Time to get off your pretty little fanny and start the day. Why don't you take a quick bath and meet me in the kitchen for breakfast. We'll discuss the day's events once we get back together. I'm going to call in and take off work for the day, and since I'm off the next 2 days, it will give us a nice, long, 3 days together to get to know one another better."

"Okay Cindy," Michael said. "I'll do that. Besides, I love the idea of sinking into that tub of yours. Its really hard to keep me away from it after last night's bath."

"Good, baby," she replied. "And use a shower cap. No since washing your hair until we decide what to do with it."

"Yeeeaas mom," He answered jokingly, using an exaggerated tone of exasperation on her. When Cindy looked back at him in wonder, he responded by playfully pinching his nose and sticking out his tongue.

While fixing up a breakfast of bacon and eggs, Cindy reflected on the fact that at least Michael already had a nice long hairstyle that was sill in fashion for the boys in this day and age, although it was starting to get more popular to have it cut a bit shorter now. But at least the way it was didn't detract from the effeminate course his Mother had already started the boy on. She shuddered at the thought of the boy wearing a crew-cut and having to deal with all that he was going through on top of maybe having to wear a wig to keep from being ridiculed too badly.

Just as she finished, and was placing the food on the table to eat, Michael walked in clean and fresh smelling from his bath. He was wearing, Cindy saw, the lacy, see-through teddy and bra she gave him last night to wear, again without any panties. He also put on a lacy, see-through nightie on over it. It pleased her no end to see he did this with no prodding from her.

"Oh, don't you look gorgeous,dear," Cindy cooed lovingly, giving a blushing Michael a brief hug while directing him to his chair. "And you smell so very nice too."

"Thanks, Cindy," he answered. "I used a bit more of the bath oils that were there. They really feel nice on my skin, now that I don't have any body hair -- almost luxurious."

"Well, sweetie," she started. "I'm glad you like them, and you're right. They do make you smell nice and girlish, and luxurious is exactly the word I would have used. Now though, let's eat our breakfast and then settle down to the business at hand. We need to talk some things over, some very important things, but breakfast first. It's really simple, just bacon and eggs. I hope you like it."

"Yummy, Cindy," Michael said upon finishing his meal. "That was really good. I was still hungry from last night too, so that really hit the spot. Thanks a lot."

"You're welcome, Michelle," Cindy replied, while just finishing her own breakfast. "I'm glad you liked it. Now, why don't you help me clean up this mess and take care of the dirty pots, pans and dishes, okay?"

Pretty sure it was more of a command than a simple request, Michael replied, "Sure, I'd be happy to," while realizing that he actually was happy to help.

Before they started, Cindy walked into the pantry and, upon opening the door, took a couple aprons from a hook there and first put one on herself, and the other, a much lacier, flouncier neck to mid-thigh length apron, she placed over Michael's head.

"We must always protect our pretty clothes, dear," Cindy said instructively. "I really should have had you wear a bib while you ate to keep from possibly staining your precious things as well. That was my fault for being so neglectful. I'll remember next time. If I don't, you must remind me, okay? I have the most precious thing in here that you'll just love to wear, I just know it."

At that, Cindy reached down toward a drawer under the sink and pulled out the laciest, most sensuous looking satin bib that only a girl could want and desire to wear, and Michael loved it on the spot.

"I see you like it. That's good," Cindy said.."But that's for later, as I said, while we eat. For now, let's get back to the task at hand."

So it was that Michael and Cindy had at the dishes and pots, et. al., Michael washing, Cindy drying. While doing so Michael tried to get from Cindy all that she wanted to talk to him about, but was unable to garner any information from her. She wanted them to wait until they could get comfortably settled before they began to discuss the subjects at hand. So they talked about her business a bit and her job at the shoe store for a little while as well.

When they were finished, they put everything away. As they dd so, Michael noticed how stained his apron had gotten during the washing and was told to put it into the pile of clothes to wash.

Johnboy9
Johnboy9
434 Followers