A Learning Experience Ch. 09

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Josie transforms. The young caterpillar becomes a dragonfly.
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Part 9 of the 10 part series

Updated 06/07/2023
Created 06/14/2013
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Joscelyn2tg
Joscelyn2tg
225 Followers

---

This chapter is dedicated to those of our Brothers and Sisters who have left us far too soon.

Thank you for waiting so interminably long between chapters. I am afraid I allowed my enthusiasm for editing wonderful new stories by other authors get a bit out of hand. But I have taken some time off to finish my little transition Biography. I would like to lovingly thank all of you that have provided me your wonderful comments and support during this time. I wish some of our Siblings were still with us to have seen the end as well as the beginning of the story. That is my most fervent wish, as the self-inflicted death of any Transgendered person should be considered a failure on the part of this society and the people who allow it to exist in its current bigoted and pathetically alternate gender phobic state. We can and must do better!

At this point little Josie has both rescued and been rescued, and after having her family traumatize her into a nearly manic state, has come to realize... family... is just a word. Discovering that she had the power to decide who gets to wield such a powerful title in her life, giving to those who deserved her love, every last ounce she had. From now on she would not waste a drop of that energy on those bigoted fools that caused her so much havoc, instead pouring her love, her soul, and her caring on her Siblings in this strange game called "life". Josie now becomes transformed, moth to dragonfly. One more chapter remains, and little Josie can move on.

The first step toward change is awareness. The second step is acceptance. --- Nathaniel Branden (Thanks to zetjester1)

Tight pants and lipstick,
She's riding on a razor's edge.
She holds her own against the boys
Yea, cuts through the crowd just like a wedge!
It's your one way ticket to midnight, call it: Heavy Metal!
Higher than high, feelin' just right! call it: Heavy Metal!

Desperation on a red line, call it: Heavy Metal NOISE! (Heavy Metal, Sammy Hagar)

---

We had been having a wonderful night of dancing, when the good Doctor and Dolores finally decided they'd had enough. It was early yet for the 'young folks' as he called us, but 10pm was as far as he could go. So I hugged him tightly and kissed them both before they said their good nights to Cindy and Andy as well, and left us. Cindy had been talking with Doctor Goldmann for most of the night and now she explained it was to discuss how to best get me re-enrolled at the community college as a female student. But before I could even process this information she asked me the craziest question I think I've ever been asked in my life.

"How well do you think you could pull off being a slutty nanny?"

Even after just two 7&7s I nearly fell on the ground laughing.

"Oh c'mon Cindy!"

"Now, I'm serious," she gathered me up and brought me eye to eye with her, "could you role play a decently hot nanny?"

"Um, gawd... wot... you have some old geezer that wants me to put him to bed with my tits in his mouth... I mean... I dunno Cindy... sure... I guess, why not?"

"Good, follow me!"

Sisters Nightclub was at that time owned by a group pf partners, as many businesses are these days, except in this case all of the owners were women, and it was actually stipulated in the contract they all signed, that while the nightclub was in business, it had to be owned only by females. This had begun as a group of lesbians, but had grown in scope to include 'straight' Mistresses that also belonged to the Sisterhood. It had now become a preeminent site for what is known as "The Lifestyle", or the S&M, or BDSM lifestyle. To help the various Mistresses that use the club for sessions, several rooms had been constructed on the bottom floor. Each had its own 'theme' and feel, and gave the Mistress a place to call home, so to speak, to use as her own dungeon. For every Mistress needed such facilities, and once the Sisterhood became involved, these rooms became sacrosanct... the Mistress ruled here, and to defile her lair... well, this was done at one's peril.

"I've booked one of the rooms for tonight," she told me as we walked down the main stairs, "I can't remember if you've had Mary's course on Paraphilic Infantilism yet?"

"Oh yeah, you mean the baby or diaper fetishes?" I replied.

"Right, oh great, that will help... we're right over here..." she said as we came around a corner and walked into what, at first glance, appeared to be a nursery. With a few moments study it became obvious that all the furniture was larger than you might expect. Quite a bit larger actually.

"Josie... Andy is convinced you simply hate him, and I haven't been able to change his mind, its something to do with his childhood issues, and I would really appreciate it if you would help me get him past this, because its beginning to really split us apart."

"Oh no! Oh Cindy!" I exclaimed, "you know I love Andy like a brother, where did this come from, or do you know?"

"I don't think he ever got past that day he was affected by that damned Spanish Fly", she cried, "I could just shoot myself for ever giving it to him!"

I hugged her tightly and let her cry awhile, then asked what she had planned, because knowing Cindy and the good Doctor, THIS was what they were actually discussing tonight. During my first long weekend at Andy's house months ago, we had gone through an interesting night of S&M role-play that Mel and Cindy had set up for us. It turned out that Cindy put some Spanish Fly into our drinks for fun that night, but it had another effect on Andy entirely. Not only did it make Andy sleepy that whole night, it apparently also interacted with a mild anti-psychotic drug that Andy took on a regular basis for a psychological problem he had been dealing with since he was 8 years old when his mother was killed in an auto accident, leaving Andy open to his feelings of paranoia, and causing him to try and attack me in his car when he was bringing me home from the beauty salon.

We had all hoped Andy's dad could treat his problems and get him over the attack he'd suffered, and at first he seemed to recover completely. But he slowly became distant with me. Rarely interacting and then after the blow-up with Roy, we simply were friends in name only. By the time all the mess with his Dad and mine happened, things had grown very cool between us. And yet he had always had an obsession for me, so Cindy hoped maybe we could try and revive that passion tonight.

"Well, this is Andy's fetish, he loves diaper play, absolutely regresses into it," Cindy explained, "so I want you to take control of him, I'm usually his Mommy, so I'm going to pass control to you as Nanny tonight, and see if he responds... you'll probably need to be very physical, he won't be happy about you knowing at first... but I think once you show him you really do care, he'll see the light... at least that's what the Doctor is hoping... he's given me some tips, anyway... what do you think?"

"You know I'll help in any way I can honey, I owe you and Andy so very much." I said softly.

"Thanks Josie, I knew I could count on you," she seemed in control once again, smiled over at me and said, "lets get you all nannied-up!"

"Um... what about Mel?" I asked, puzzled how I would explain things to her.

"Oh! Gawd I'm so pre-occupied with my baby... well... you did promise her a punishment tonight, right? So... might be fun to be 'Nanny of the Nursery' for a night with your favorite sub VERY humiliatingly stripped, diapered and dragged off to be spanked by her nanny... hmm?"

Suddenly those images were everywhere in my head, and causing my Peter to react. "But Cindy, we've never discussed spanking or even any type of corporal punishment... how...?"

"That's okay sweetie... we have... and she has already committed to you as her Dom Josie, you know she loves you beyond anyone I've ever seen her with... you'll do fine, and I'll help you."

"Oh Cindy... you better be right about THIS!"

"I am, I am... you'll see!" she laughed, pulling open cabinets and yanking out supplies.

***

About a half an hour later, we were as ready as I thought we could be. Cindy had contacted the management to let them know we may be causing a small disturbance in the main lounge, two large bouncers, dressed in white of course, accompanied us, mostly in case a customer misunderstood, and tried to interfere, which rarely happened, as these events were quite common at Sisters. I had a couple ideas on where to start things off. But my appearance as part of his fantasy was the primary factor we hoped would get Andy 'in the mood' and out of this distant feeling he had for me.

I went pure vinyl, as in PVC plastic, for most of my 'Nanny' image. Which is not easy to pull off considering what I was about to do. However, it was by far the sexiest look I could engage in, and I wanted Andy totally knocked out and gagging for it before the night was out. My Music Club buddy was about to become my fuck buddy... in every sense of the phrase!

My costume was 1950s Nanny, and I started with translucent black, back seamed hose, and a black, six garter, garter belt, trimmed with pink bows, also needed was a black PVC gaff panty, with matching pink ribbons of course. I then added a black hobble skirt, that fell just below the knee, yet had a well thought out back slit that allowed me a goodly amount of movement for the kind of action I was expecting. My ladies were taken care of by a maidenform styled PVC push-up bra, in black and also with vibrant pink bows and trim. Topping the 'wet look' off was a translucent white PVC blouse that showed absolutely everything, but just barely, its puffed out upper sleeves giving just enough feminine flavor to match its strict lines, and finally, opera-length PVC gloves. Cindy pronounced me 'wet dream capable' and off I went to start a fight with a friend. Hopefully it would end peacefully, and extremely sexily.

As I reached the table we had been previously drinking at before Cindy and I left, I saw Mel had been keeping Andy nicely distracted. He loved to dance and so did she, but at the rate he was downing vodka martinis, his dancing was becoming much more erratic. I stood back behind another booth and watched as they returned to the table, Andy showering Mel with compliments on her dancing, it actually looked like my friend was making a play for my girlfriend! If I wasn't about to make a play for him, I might have been upset, but I took a last look at my costume and put on my best foxy smile.

Five steps in a PVC hobble skirt, brought a vision in six inch black patent leather pumps directly into view, with just about everything I was wearing glistening like times square after a rainstorm, I brought all activity anywhere near that particular table to a standstill. Shaking out my over-the-shoulder blond locks, leaning across the booth's table, supporting myself on PVC opera length gloved arms, as my ladies practically spilled onto the white tablecloth. I pursed my dark red lips and raised a black-lined brow to address my Melissa who sat stunned and seemed lost somewhere in my cornflower irises.

"You've been a very naughty little girl today... and you're going to have to be punished. Its past your bedtime little Mel... better come with your Nanny sweetie."

"J-J-Jo-Jo.... HOLY SHIT... Josie!?" I seemed to have also gotten my desired reaction from Andy.

"We were um... well, I mean... I thought we might dance one more song, you know... since its been so long and all. I just thought..." his thoughts were now starting to wander down my chest.

Now he actually got up and came around the table to me. He only stumbled once, which I kept an extremely close eye on, as I was gathering every piece of information I would need for any confrontation such as this. Standing toe to high heeled toe, we were within inches now.

"Look Josie, whatever she's done, there is NO reason to act," now he took a long look, scanning my PVC clad body carefully, "like this, anyway... if Mel doesn't want to go with you, you can't make her... punishment... jeez... that doesn't even sound like you!"

Just then Cindy walked up, also wearing a similar PVC Mommy Dearest outfit, grinning in her usual cat that got the canary style. And from behind her, the two bouncers were rolling a very large white painted crib with pink markings along the floor, one wheel making a constant squeak that could even be heard over the dance music.

I rubbed a PVC gloved hand over Andy's shoulder, smiling wistfully and staring directly into his eyes, as from just behind him, Mel was trying desperately to get his attention, shaking her head to make him step back from trying to defend her, as she knew me well. I was role playing, but I was the Mistress here, and Andy was challenging the ultimate power in this building... he was digging himself a hole, and I was providing all the shovels he could handle.

"I think maybe Andy-Pandy's a little over tired... is my baby needin' a sleepy-bye?"

I saw his annoyed reaction in such slow motion that I easily caught the right arm he planned on using to slap me with my left, and had it coiled and locked behind him so fast I heard Mel gasp at the speed of my reaction. With the stern look I now had on my face, I only needed one word for her, my Dom voice caught her mid-jump as she tried to come to Andy's rescue. I used my pointer finger with "Stop!" to freeze her in place. I now pushed Andy up against a support wall next to the little booth where Mel was an ice sculpture, mouth open and eyes searching for mercy.

"C-C-Cindy!? What's... uhhh!... whats hap-" Andy shouted, squirming in my strong grip.

"I never hated you sweetie... your Nanny loves you... and she's gonna show you... right now!"

My left knee was up between his legs, and the look in his eyes had fight left, but it was disappearing quickly as he saw Cindy again give him her most beautiful smile. I took the moment and used it to best effect, and as his mouth relaxed, I pounced. Kissing him hard, launching my tongue down his throat, easily overwhelming his own and running my PVC gloved nails up his back, feeling him arch it in response. A noticeable bulge growing over my PVC encased knee told me I was having a very positive reaction. I giggled madly now, watching him begin to understand... he was my target!

"Aw... such a naughty little boy... don't worry... Nanny's got all your pretty toys."

With my right hand I grabbed the tablecloth and cleared the table with a single yank, and with glassware flying off across the aisle and up against another support wall, I spun Andy around, kicking his only supporting leg out from underneath him. Cindy now stepped up and joined me as I laid Andy down onto the table. He tried to sit up but I easily flattened him with my left knee now keeping his back firmly attached to the table right in front of Melissa. As I pulled each piece of clothing off of him, making him ever more naked, his eyes were growing to the size of saucers.

"Shhh! Mommy's here for you sweetheart!" Cindy was cooing to as I stripped him to nothing in under a minute, then Cindy began passing me items and now it was Mel's eyes that bulged. I quickly used some baby wipes to clean him up, lifting him as Cindy slapped an adult diaper under his clean bottom, and I then sprinkled some talcum powder on his crotch, and fastened its tape strips, followed by a pair of frilly locking retaining panties to hold the diaper and keep little hands from trying to remove it. Once pulled up and locked over the diaper they weren't coming off any time soon.

White stockings were rolled up his legs next, quickly followed by black patent ballerina slippers that attached and locked around the ankle and would keep his toes pointed straight down and available for dancing, but little else. He was determined to talk again, as all overly tired children get, so Cindy passed me a pacifier that would keep the old motto 'silence is golden' true... and mandatory. Its strap slipped around his neck and merged with a blue baby bonnet that went over his head, keeping a nice little rubber dildo locked into his mouth for him to suck on. I then pulled slippery PVC mittens over each hand, hearing them lock around each wrist with a light snapping sound, making his hands both pretty and useless. Finally a blue 'boys' pinafore, that wrapped around and tied with a large bow in back, and also locked his elbows behind him to keep prying little hands at bay. Andy was now quietly sucking on his pacifier as I kissed his cheek and lifted him gently into the white crib that our two bouncers had nicely opened for me. He was quite incapable of doing much else.

The look on Mel's face was absolutely amazing, she had long ago left us and was deep into her 'sub zone' as I gave her my hand to stand up with. We helped her out of her little black dress and lingerie, with Margret and at least a few dozen onlookers watching in rapt attention as my double was diapered and put through all the same humiliation Andy had just been through, and seemed to be absolutely enjoying. Once we had her pink bonnet, mittens, and pinafore locked around that lithe beautiful body, she also seemed to regress... becoming a 19 year old baby... sexiest damned baby I'd ever seen as I lovingly picked her up and placed her in the crib with Andy, they hugged each other as best they could in their pink and blue mittens and looked about as cute and adorable as anything I'd ever seen. Cindy put her arm around me and I kissed her cheek, and hugged her back, as we slowly rolled our 'charges' down to the nursery.

Once downstairs, we bid our bouncers goodnight, brought the crib into the Nursery room and locked up for the night. First we brought the children over to the playpen for some quick stimulation before bedtime. The play pen was about four times the size of a real one, and a soft mattress on the bottom gave us a nice soft play area. Mommy Dearest and I took off out top layer of PVC, mostly just to cool off 'cause that stuff gets stinking hot, especially the layers we had on. Cindy donned Andy's favorite strap-on and gave me a little of the Spanish Fly that caused Andy such distress, but it helped my Peter feel stronger, and that's who was needed tonight. Cindy began lubing Andy's backside, and I went over to my darling Mel to see how she was doing.

"Hi sweetheart," I said happily, "I think you've had all the punishment you need, don't you?"

She nodded, and tried to say something, so I unfastened the strap of the pacifier and bonnet, and removed it, then I began massaging her back and neck. Then removed her panties and diaper. While on the other side of the playpen, Cindy was doing the same for Andy.

"Would you like your Nanny to give you your reward now sweetie?"

"Yes! Yes Nanny... please fuck your little Mel... she needs you so bad!"

"Okay... baby," I laughed, "your wish is my command."

I stroked her gorgeous labia and soft mound of pubic hair, licking it softly as she began to writhe on the soft mattress, her soft mittens surrounding my head as I began to get her off. I pulled off my gaff panty and the Spanish Fly was doing 'its thing'. My beautiful Melissa was ready for me and I brought my Peter over her dripping young pussy, laying it onto hot labia as she sucked in a deep breath, and arched her back to gain access. I smiled down and held her hips tightly, then an small thrust drove me in easily, she was incredible! Fireworks exploded behind my eyelids as I realized just how incredible she was.

Cindy had prepared Andy for his penetration and he and my Mel were now head to head, as I took Mel from one side, and Cindy was thrusting into Andy from the exact opposite corner of the playpen. Gradually our combined thrusts were pushing our partners together, with Mel being on her back, and Andy being taken doggie style. Andy's head was now right over Mel's face and they began kissing each other as Cindy and I continued our manic thrusting. After a few more minutes, it was obvious we were pushing them into a "69" position. Andy's was kissing Mel belly button and Mel was nearly able to claim Andy's rock hard cock.

Joscelyn2tg
Joscelyn2tg
225 Followers