A Learning Experience Ch. 04

Story Info
Becoming Joscelyn, with bondage and heartache in the mix.
21.1k words
4.73
36.2k
26

Part 4 of the 10 part series

Updated 06/07/2023
Created 06/14/2013
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Joscelyn2tg
Joscelyn2tg
226 Followers

---

This is chapter 4, My apologies for the delay in getting this out, I only hope it was worth the wait. And I must also hope my readers understand that I have kept BDSM in the tags for this story because I have always had a serious interest in S&M, and this chapter begins my exploration of that new world. Sorry if this takes away from your enjoyment of the story, but it is a part of many TG's lives and therefore I believe its germane to this story overall. Cheers! -- Joscelyn

---

Chapter 04

----------

After admitting a long kept secret desire to become a woman to my three best friends at college, I've begun therapy with Andy's dad, a well-known psychiatrist, who feels that I should attempt to be a woman full time. I am staying the weekend at Andy's house while meeting with his dad and have just finished my first day of therapy. I crashed for a nap waiting for Andy and the girls to get home after an afternoon shopping trip.

As I am floating through space and time, I am slowly beginning to recognize voices around me, as if a long way off and I can only hear them as echoes.

"Aww, so adorable!" voice X says, "I can't wake her, I don't have the heart."

"We have to," voice Y says, "You heard what he said, she needs to keep up her meds."

There is a loud sigh, "Alright sister... but let me do it my way, ok?" voice X says.

"Whatever, just hurry up, dinner will be ready in 30 minutes!" voice Y exclaims, "I'll see you downstairs hun!"

Once again I am left in silence, and I begin to fall, slowly at first, like rolling down a hill, then faster, and faster, until suddenly I've fallen off the edge of a cliff! However, just before the edge, a hand reaches out and catches me. I'm dangling, looking down... my feminine form is unmistakable, my legs pedaling through a dark mist are blocked from view at times by my breasts, when I suddenly look up... clouds are flying by overhead, and now I can see the hand that has me in its clutches. It's strangely familiar, well-manicured, soft skin, and opaque coloring, but all is dark around me... 'Melissa', I call out softly, it's hard to breathe for some reason, and I can't get enough air in my lungs to yell for her to hear me. Now there is a sudden lightning flash, followed by a loud clap of thunder. I can see her figure above me for fractions of a second. I pull all my strength into one great scream to make her hear me, make her rescue me from my darkness... I scream – and I am suddenly bathed in light, but it's from the lamp next to our bed. Then I hear another thunder clap, it sounds like a thunderstorm outside.

"Jack?" Mel asked, "Are you ok Jack? You were yelling my name just now."

"Yes my darling," I answered, "I'm fine now. I think it was a nightmare."

Sitting on the bed next to me, she is holding my right hand in both of hers, stroking the tops of my fingers, then bringing it to her mouth and kissing each finger. I take my left hand and my fingers stroke her face, taking soft swipes of her cheeks.

"What time is it honey?" I asked.

"Oh... it's about 6:15, almost time for supper baby!" she answered.

"So there's a rain storm outside?" I asked, not sure if it too, was part of the dream.

"Mm-mm, yeah it's getting pretty bad, good night to stay home," she said.

"Mel?" I quietly asked, in more of a prayer than a question.

"Yes baby?" she replied.

"Mel?" I asked again, "Mel... I think... I think I'm... I'm falling in love with you."

"And Mel?" I quickly continued, "There's just so much going on right now... and..."

The tears in my eyes finally had nowhere else to go and I wrapped my arms around her beautiful torso, burying my head into her abdomen, I couldn't speak anymore.

"I know," Mel said as she stroked my long blond hair, "I know, and I love you too... so much baby."

"But..." I started to say, "Will you still love me... once I'm... when... oh hell..."

"Alright now... you have to listen to me about this!" she declared and held my head up so we would be eye-to-eye, "I will love you whether you decide to use the name Jack, or Joscelyn, or... Humpty Dumpty... ok? I'm in love with what's here my darling, not here," she said, pointing to my heart, and then to my crotch.

"How did I get so lucky?" I said shaking my head through the tears, "How did I ever manage to find you... you are... amazing... lovely... generous... beautiful... compassionate... and loyal," I finished each word by kissing her at a different point on her face.

"You must just live right, I guess," she laughed, "Now c'mon, Dolores has supper ready, and everyone wants to hear about your day, and I want to tell you about mine!"

"I love you," I said.

"And I love you baby," she replied, "now c'mon!"

She finally got me awake enough to stumble out of our bed, being accompanied all the way down to the kitchen by massive thunderclaps and lightning strikes outside. Surprisingly we were right on time, and everyone was starting to sit down to a beautifully laid out table, Dolores had really out-done herself that much was clear.

"There's plenty of candles around," Dolores was saying, "in case the lights go out again, and I've made rack-of-lamb with my special mint sauce for dinner!"

There were Ooohs and Aahs flying from everyone's lips, as we all now remembered just how bloody hungry we really were! Finally Andy's father joined us, and Dolores served all the dishes, and sat down herself. The doctor then did the honors, opening the wine and letting it 'breathe', and then we each sent our glass around for filling. It was then, that I knew exactly what I needed to do. I felt it so strongly that nothing could have made me change my mind about it right then. Once we all had our wine, I took my butter knife and tapped it against the rim of my glass.

"My dear friends!" I announced, "My very dearest of friends, I want to raise a toast to the people who seem to care about me most, who care about me so much that they are willing to love me no matter what gender I may need to become, and are willing to provide any help I need in order that I might finally be comfortable with my self. What better definition of 'friend' could there possibly be? It has taken a seemingly long time to get to this point, but I can only count myself as the luckiest of people, man or women, that has ever lived on this planet, and I owe you all a great debt of thanks... Cheers!"

"Cheers!" all of my friends replied, and after everyone drank, there were claps as well.

We then chowed down to one of the best dinners I'd ever had. Everyone seemed interested in how I was feeling about my future. We didn't really talk about any of the specifics that were part of my therapy. I asked several questions of Dolores, about how she was able to transition, and how she went about making all the adjustments to her life, it was an amazing story!

"And so how did the shopping expedition go?" I asked.

This seemed to get a pretty good laugh, so whatever happened must have been interesting, but suddenly everything stopped with a lot of sideways glances and snickering remarks that I wasn't catching.

"Well... were you able to find what you were looking for honey?" I asked Mel.

"Oh you bet!" she answered, "We found some truly incredible stuff, you'll be really amazed baby, I promise!"

"Mmm, well I can't wait!" I said.

Mel smiled as she replied, "Oh yeah sweetie, its gonna rock your world!"

Suddenly I had Mel's hand working itself up my leg under the table, and wasn't sure that this was such a good idea right at this particular moment.

"Would you like some dessert Jack?" Dolores asked me.

"Aaaah, yeah... s-sounds r-really... um... grooo-great!" I tried to answer.

"Jack just loves sweet things, don't you Jack?" Mel asked between giggles.

Finally we were able to get through dinner, but just barely without causing a scene. When Mel dropped her napkin, and was under the table picking it up, she managed to get 'peter' out of his zippered compartment, and I nearly lost it right then. Andy and I volunteered to clean up the dishes after Dolores had cooked such a fabulous meal!

Once the Doc and Dolores excused themselves for the night, that brought my anxiety level down considerably. It didn't take us long to clean up the kitchen, and load up the dishwasher. Cindy and Mel then excused themselves to set up a private showing of what they bought that afternoon. I asked Andy if he had any idea what they were up to, because they had been rather secretive all during dinner, but he just said that he went and looked through some music stores while they were buying clothes, so he would be just as surprised as I was. A few minutes later, a dejected Mel showed up as Andy and I finished cleaning the last few things in the kitchen.

"I'm sorry Andy," Mel said in a sad voice, "we forgot a couple things that we'll need in one of the stores we went to. Could you be a dear and drive me over there?"

"Well..." Andy began, "it's a pretty ugly night, is it that important?"

"Oh please, please..." Mel begged, "I promise you'll love the result!"

"Oh! In that case..." Andy declared, "no problemo babe!"

"Keep yourself busy sweetie!" She said to me, "We'll be back in a half hour, tops!"

After Andy and Melissa had left, I wandered over into the game room, where Andy had a nice stereo system, a big-screen TV and several arcade style machines, as well as a few pinball machines, and one regulation sized pool table in the middle of the room. A few minutes later, just as I had cranked up the stereo with an FM radio station that was playing Abracadabra by Steve Miller, Cindy strode in and I was definitely spellbound!

She was just smokin' hot! Dressed in a black calf's leather corset, the scent was delicious and the cups just barely covered her tits. Her skirt was also made of calf's leather, but had no 'back end', and just a 3-inch strap went around the bottom of the skirt's 'hem'. It was barely covering her magnificent ass, and this was combined with a 2-inch black leather belt that had a 6 or 8-foot leather whip coiled up and hanging from it. She also wore a leather dog collar, with a set of D rings at the cardinal points. Black fishnet pantyhose and black thigh-high calf's leather boots with 6-inch heels finished the look. And what a look! The most deadly looking wet dream that anyone could possibly have put together, and there she was, standing in front of ME!

Suddenly I noticed something vaguely familiar, Cindy's hair was 'up' in a bun on top of her head. But... I had seen this before...

"Wait..." I said, "It was you, wasn't it? You! Yes... It WAS you that day!!"

It had been just a few days into September, I was desperately late for my second class of the afternoon and the halls were empty. Just as I rounded a corner before a teacher's office door, I saw 'her' coming out of that door. She hadn't had a chance to close her long coat yet, and she was lighting a cigarette. Under her coat she was wearing a complete dominatrix outfit, and it was 'exactly' the same one that she had on tonight, she even had her hair the same way.

Cindy's face now had a red sheen to it, as she smiled, then almost skipped over to me, crouched down, and in nearly a whisper said, "Yes Jack... it was me, I thought this might finally jog your memory, I kept wondering when you might remember me, as I knew it was you that saw me. I was just finishing up a job for a teacher that wanted a silly little fantasy fulfilled, so for a passing grade, he got his wish. Don't worry, it was nothing really sexual, he just wanted to be paddled by a 'teacher'."

"Wow, you do look incredible by-the-way," I said, "I had so many fantasies of my own come up after seeing you in that doorway... wait... Oh! That's why all the 'looks' you had been giving me... You must have thought I was trying to play some kind of game or something, you didn't know that I never recognized you!"

"Yeah," she replied, "I was so pissed that you wouldn't say anything, then about the third day after we first met, I realized you just didn't know that it had been me!"

"I could not figure that out," I said, "Sometimes it looked like you were shooting arrows at me with your eyes! Its made me feel uneasy around you ever since!"

"Now Jack... I need one favor..." Cindy asked, "We each know something rather... well, embarrassing about the other, right? So please don't tell Andy, hmm? He knows I used to do stuff like that, but it won't help anything to tell him about it now, ok?"

"Ok Cindy," I agreed, especially since it happened long before she and Andy had become friends, "You've been a good friend to both Andy and I, that's not too much to ask. So now what?"

"Well," Cindy continued, "I set this up so Andy and Mel would be gone for a little while. I thought maybe you and I could clear up my 'identity' and perhaps just get... a little better acquainted?"

Cindy then sat down on the couch next to me and got comfortable. She looked as sultry and sexy as any woman I've ever seen, and if I wasn't as in love with Mel as I was, I might have been sorely tempted to cheat on her right then!

"Ha, ha!" Cindy laughed, "Oh Jack, that's not exactly what I meant, but thank you for undressing me with your eyes, always makes a woman feel good to be desired!"

"Oh," I said rather timidly, "and so what did you have in mind?"

"Jack..." She continued, "What do you know about sadomasochism?"

Now it was my turn to blush, "It's a type of fetish, isn't it?" I said.

"Mmm, yes, it is that," she explained, "and a good deal more. I've talked to Mel about you and she feels that you have some interest in the bondage aspects of the S&M 'lifestyle'. There's a lot to this lifestyle Jack, more than I think you're really ready for with everything else you're dealing with right now. So I've been hesitant to bring it up with you, but I would like to get some idea of what parts of S&M you find exciting, and also what you might find a 'turn off'. Do you mind...?"

She paused to light her cigarette, and did so after I shook my head to show I didn't mind. Then crossing her fishnet covered legs, and taking a deep drag, she again settled back into the couch, giving me a truly exotic image, one that was burning into my mind just as vividly as any playboy centerfold I'd ever stared at while trying to get off.

"You see Jack," Cindy continued, "I've been Mel's mistress for the past year or so, ever since she discovered her own 'needs' within S&M. She's hoping that you might become her mistress, once you have become Joscelyn. I've agreed to help with this, if you are agreeable, first to see if you are 'top' material, then to train you to become a responsible dominatrix, and finally to bring you into our sisterhood. This will all take time and effort on your part, which won't begin until you're well into your transition, but which should also help your transformation into Joscelyn, as well as other benefits."

"Our first and most important rule," she then declared, "is the SSC rule, and that stands for Safe, Sane, and Consensual. Mostly this is so each party knows, ahead of time, what activities are expected, that's the 'consensual' part. The safe and sane parts should be pretty self explanatory!"

"I see," I began saying, "but before you go any further, I think that I need to explain myself a little better perhaps. When Mel and I had our 'talk' about S&M, I did tell her something about my own desires relating to that, but I also stopped the conversation as soon as I could. The reason is... I get terribly embarrassed after having an orgasm using bondage, almost as if I can't really control myself. I worry about wanting to tie others up and I have this awful feeling that I might end up hurting someone... is any of that normal, or is this all just my own fears?"

"These are very normal feelings Jack," Cindy explained, "and it's the reason the SSC rule came into being, so that people wouldn't be hurt, or at least not hurt in any way that they are not expecting... now, like I said, this is a lot to 'take in' all at once, so I thought we might start you off tonight with some simple 'role play', as Mel and I take you down the path of feminization."

"Really?" I asked, "I love role play, but I'm not sure I understand... feminization?"

"Yes... as Joscelyn honey," she again explained, "we're going to create a scenario where we will want to 'bring back' Joscelyn, and while you probably won't really mind going through the 'conversion', we'll use it as a kind of 'test case' to use S&M within the scenario and see how you react to it in that environment. And if you like it, then we can move forward perhaps with more involved aspects... ok?"

"Oh... wow, yes... I definitely would like to try that!" I exclaimed.

"Ok, now," Cindy continued, "so you know how SSC works, we'll go through what you can expect for this scenario, we will only use basic restraints, nothing that you probably haven't already seen, or even used yourself. We may use some minor tickling and massage on you, but only for your own sexual excitement. Does this sound acceptable?"

I really didn't know what to say, although I knew I'd probably say yes to just about anything this gorgeous creature asked of me. But then her eyes narrowed and she said, "But this is absolute... during the scenario, and while you are under my control, you MUST refer to me ONLY as 'Mistress', and you must comply with my demands on you instantly and without question, to refuse is a matter of discipline, and may be dealt with quite severely. If you feel I am taking you beyond your 'comfort zone' Jack, you will have two 'safe words'... 'White' will mean a temporary 5-minute stoppage in our role-play, if you feel that you just need some time to recover. 'Red' can only be used to stop the role-play completely... Once you use 'red', the role play ends and we will have to re-consider whether you would be a good 'fit' for our S&M lifestyle... do you agree to these terms?"

"I-I... um..." I was stuttering again (well, wouldn't you?), "Sure... um... I'll agree Cindy... white and red, right?"

Cindy was smiling at my naiveté, and tried to speak soothingly, "Alright then, oh... one more thing to remember, if for some reason you cannot speak, contracting one leg, or 'jerking' it up and down, will be taken for 'white'. If both legs are used, that will be taken as a 'red'... ok?"

I couldn't imagine what that really meant, but no doubt I would end up finding out. At this point my cock was rock hard and straining for release. So I knew that whatever happened from here on tonight, I was going to be ready for it!

"Ok Cindy!" I declared, "Where do we go from here?"

"Once Andy and Mel get back," she explained, "just get Andy in here and wait for the 'play' to begin, ok?"

"Does Andy know what's going to happen?" I asked.

"Oh no, not at all!" she laughed, "I'm sure he'll love everything we come up with though, so don't worry about that."

"Well, I just want to make sure he'll be ok with it, he's been incredibly nice to me and I wouldn't want to do anything to upset things, ya know?" I said.

Now Cindy went very quiet, sighing and shaking her head slightly, she finally spoke up and said, "You really don't have a clue, do you?"

I gave her a surprised expression, and simply shook my head in confusion.

She gave another huge sigh before saying, "Honey... remember Andy's bi-sexual?"

"Um... yeah, sure but..." I replied.

"He's been infatuated with you, ever since he first laid eyes on you," she continued, "Mel told me that you really had no idea, but I just feel like you should know this."

"Oh!" I replied, "Oh jeez, Cindy... let me put your mind at rest on this one, Andy and I have talked about our feelings for each other, and he feels exactly the same as I do, we both feel a brotherly love for each other, and that's all... really!"

Joscelyn2tg
Joscelyn2tg
226 Followers