tagTranssexuals & CrossdressersA Learning Experience Ch. 05

A Learning Experience Ch. 05



*** Warning: This chapter has several sections which contain rape, violence and physical abuse as major parts of the story. If these things would bother you, please don't read this and wait for chapter 06, it will be along soon. However if you wish to understand all of my transition and what was behind the many hard decisions I made... then it becomes imperative to read these sections and follow how they affected me, my friends, and my family.


After admitting a long kept secret desire to become a woman to my three best friends at college, I had been spending a long weekend at Andy's house with my girlfriend, Melissa and Andy's girlfriend Cindy. I 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 snuck 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. Andy's dad, the Doctor, has given him some fast-acting drugs that seem to have brought back the Andy we all knew and loved.

The Doctor has insisted that we have our therapy session, as planned this afternoon, and we have spent the last couple hours getting my head back where it should be after my scary ride. But it also had been a good 'catalyst' as he called this disaster (well, 'disaster' was my word for it), and he believes that I may have gotten some additional strength from this, that otherwise would not have had the opportunity to emerge.

"Oh, I dunno Doc..." I frowned in reply, "maybe, but I can't really see how..."

"Ok... On a scale of 1 to 10, 1 being least, and 10 being most..." he was saying, "What do you feel your confidence level with being a woman is right now?"

"I guess about an 8," I said.

"And before you left for the salon, so before anything happened there," he quickly continued, "what would you say your confidence level was then?"

I knew he wanted a quick response, "Well... a 4 anyway... maybe a 5."

I could feel his smile before I saw it, I just shrugged as I knew he was right, instead of everyone worried about me and how I was coming along, we were all worried about Andy and I'd suddenly had to 'make it work' in my new 'body'. I couldn't hang back and wait for everyone to deal with my life, I had to grab my own life back and force it to give me what I needed, as a woman. And I knew that without this whole mess happening, it would have probably taken a lot longer for me to feel this confident about who I was as a woman.

He also had some rather startling results from the tests that he'd done on me the previous day. It seemed that I did have 'some' attraction to men, what he called my 'latent' bisexual feelings. He felt that I should try to explore these feelings, as they may help me in my transition eventually. I did explain the little scenario that Mel and I tried out that morning, where she had dressed very 'butch' and had anal sex with me. I told him that it had made me very nervous, but that once I started, it seemed so natural for me and I thought I might really be willing to have a male sex partner. That is, if I could overcome the initial feelings of having my sexual role reversed so completely.

"Perhaps what's needed," he suggested, "is just a male to male... date, to start off, you know... nothing where you need to worry about your 'fem' side, and wouldn't that be a starting point anyway?"

"Mm-mm, yeah that might give me some idea then wouldn't it?" I said.

"Well, why don't you think about it this week," he replied, "then go slowly once you've decided on someone?"

"Alright Doctor!" I smiled trying to convince myself this was possible, "Anything else that we need to cover today?"

"Oh... no, I don't think so," he scratched his chin thinking, "I'll have your IQ and STOMAS test results for you next week... I imagine you've had plenty of occupational testing over your senior year of HS, and first year of college."

"Oh yeah," I said with little enthusiasm, "tons!"

"Well, we just need to see if your gender change will interfere with anything that you might have expected to progress normally," he continued, "or if it might be altered in scope, and I'll explain all that more next week."

Suddenly my right knee began bobbing up and down in nervous anticipation. I knew I had to broach this subject somehow, but for the life of me I didn't want to even deal with it at all. The Doctor saw it as well, and smiled as he looked on, waiting for me to finally find the words to get it out on the table.

"M-m-my p-parents..." I began with only two words, but they said everything.

It ended with a single tear from my left eye as I said the last word, "H-h-how...?"

"Would you like me to be with you when you confront them Joscelyn?" He asked.

I studied him for a long time, finally saying, "I think what I'm going to do is tell them one at a time, if you could be with me when I talk to my mother...?"

"Don't you think..." he began to reply. But I had thought long and hard on this.

"Doc, my Mom is a teacher, and she's really smart. My Dad is too, but he's really bigoted," I interrupted, "really bigoted... like beyond what you might even think possible! If we could convince my Mom, she'll take care of convincing him. The crux of this, is gonna be getting through to my Mom!"

He sat and thought for some time before simply saying, "Alright! Then that's how we'll do it, when will you need me?"

Now I knew I'd probably have my work cut out for me, since I knew it would have to be soon, VERY soon! Because she was exactly what I said she was, very smart, and she already knew something was going on. The longer I waited to tell her, the harder it was going to be to make her see it my way.

"How about tomorrow morning?" I asked, between raised eyebrows.

"WHAT?" he exclaimed looking me up and down, "You mean..."

"Yeah..." I was continuing, "I want her to see me just like this..."

"The last time she saw me in female clothes," I said, "I was 6 years old, and she told me it was perverted... because it LOOKED perverted! But tomorrow morning I'm going to look like a queen... She can accept me, or wish for the rest of her life that she had! It will be a perfect time, my Dad will be leaving early, and her school has the day off, so if you would be so kind as to drive me home... we'll gang up on her and make our case!"

"Well, we don't want to surprise her THAT badly, do we?" he was laughing.

"Pfft! You don't know my Mom," I said, "she'll be dressed and ready for company by 9am, or at the latest 10am tops!"

"Ok Joscelyn..." he said finally, "you've convinced me, I hope you know what you're doing, this could backfire you know!"

"Don't I know it?" I replied, "It's just the only way I know how to get through to her!"

"Alright... can you let Dolores know..." he started, but I already knew what was up.

"Don't worry Doc!" I laughed as I interrupted, "We'll be sure you're called for dinner!"

He smiled as I got up and I waved my good-bye, then after blowing him a kiss, I began the long walk back to the kitchen. I had made sure to mention Sid's recommendation for a Trachea Shave, and he had sent a note to his secretary to set up an appointment for me with a throat specialist. While we were going into that he also brought up the issue of my male 'Philly' style vocal accent not really going with my 'valley girl' body now. So he also asked her to set up an appointment with a female vocal coach. In the meantime, I took his warning to heart, making sure my voice stayed at least an octave above what I normally spoke with, luckily once again, my musical background came through and I found it easier than I had thought it would be to 'place' my vocal sounds a full octave above what I normally found comfortable.

As I got to the kitchen area, I found Dolores taking something heavy out of the oven, and ran over to lend a hand. Whatever was under the covered lid smelled like heaven and I made an effort to see what it was, perhaps even sneak a taste, when my hand got a pretty hard slap off of the handle of the lid!

"Ouch!" I yelled, in obvious mock pain, "Wow, and all I did was help!"

"Aww!" she cooed softly, "Here let me help you feel better..."

She took my hand between her two hands and gently sucked each digit into her warm mouth, as my mind spun off into some alternate reality I said, "Mmm, Oh my God..."

"Mmmm, better?" she whispered, "We'll take good care of you girl!"

I wasn't sure how I felt exactly, as I knew I was very attracted to Dolores, but also knowing she was like me brought out a couple very different feelings. Eventually she saw my hesitation and stopped.

"You're right," she giggled and then sighed, "it's like... well, it's almost like you're my sister on some level... I dunno... do you feel it too?"

"Yeah," I replied as I smiled back, "it is something like that, but I can't quite place it... I guess I better ask the Doctor, huh?"

"Ha ha! By all means," she said, "although I have to tell you I do feel a bit jealous of all the attention you've been getting from Cindy! It's very unusual for her to be so directly involved with the training of a novice... and I'm not the only one feeling that way, you may want to be just little careful!"

I immediately looked around to see if anyone was within earshot, then taking her by the hand she had just been 'attending', I guided her over to the pantry, and closed its door behind us.

"Ok Dolores," I said, "I need information. When I hear warnings now, I take 'em seriously. What's going on with Cindy? I know she wants me to be Mel's Mistress eventually, although I don't really even know what that means yet. So why should I be worried about her attentions for this?"

"I'm sorry Joscelyn," she replied, "I'm not trying to scare you, and there's no reason for you to be... it's just that... Cindy is a matriarch of the 'Sisterhood', and when she shows an interest in someone, especially a novice, it may draw more attention to you than you might otherwise like to have... if you know what I mean."

"Like from who?" I asked nervously, "Someone I know, or someone new?"

"Well, like..." she continued, "the other Matriarchs for example, I heard one of them telling her on the phone to 'get her priorities straight' when she was discussing you earlier today after the whole mess with Andy!"

"Wow..." I said quickly, "Do you have any idea why she's taken such an interest?"

"Mm-mm," she replied, "It began after you told her about your very difficult history and all the tough breaks you've had. Not that it was any worse than other's had, I think it just reminded her, at some level, of herself!"

"Ok then Dolores," I finally responded after a short pause thinking it through, "I'll try to keep my head down, but I'll need help, so if you hear any more, please tell me, ok?"

Now Dolores' smile broke through so brightly it nearly lit up the little pantry all by itself, "You know I will honey, I told you I would take care of you, and I meant it!"

Turning off the hanging lamp, we walked back into the dining room, with nobody seeming to have noticed our absence.

"Need any more help hun?" I asked Dolores.

"Nope!" she replied, "Not right now sweetie, see if you can round everybody up, and let 'em know dinner will be ready in about a half hour, ok?"

"Alrighty then!" I responded quickly, leaving to search upstairs for everyone.

As I reached Andy's room, I saw Cindy and Andy lying next to each other, Andy's eyes were closed and Cindy's looked over at me with a finger quickly coming to her mouth to keep me from saying anything right then. She carefully got up off of the bed and came around to me, looking back to make sure Andy was still asleep, then she passed me going into the hall and I turned to follow her. As we walked over to Mel's and my room, I saw Mel asleep on our bed and smiled at such a beautiful scene.

"Cindy," I began to speak but she again shushed me.

"I know..." she whispered as she focused on our problem.

"I'll need some nicotine for this," she said as she eyed my determined jaw, "c'mon - follow me downstairs and we'll talk outside for a few minutes."

She quickly stepped back into her room and grabbed her purse, then again walked by me as she skipped down the stairs and quickly walked out the back door, headed for the little garden behind the kitchen. It was cool, but still comfortable as the sun was fading fast by this time. There was a small iron bench along the garden wall that was just barely hidden from the view of the kitchen window. Cindy sat down and got out her cigarettes and lighter, I sat down next to her as she tried to get the old tired lighter to actually do something like create a flame. I took it from her trembling hands and forced it to produce a flame and lit her cigarette for her, then dropped it back into her purse. She nodded, and smiled in appreciation of my mechanical ability.

"Thanks!" she said pulling a long drag into her lungs.

"What's happening here Cindy," I said in a complete monotone, "I mean... what's happening here... to me... and why?"

She looked me over for a few seconds, then said, "Ah... The Sisterhood!"

"Yes, but first, what was your warning about Andy all about," I said, "and I feel like such a fool for how I ignored you... is there anything else I need to know?"

Now she seemed to get very serious, "Oh Joscelyn! That had absolutely nothing to do with what happened to you today! My 'warning' was the most benign of things next to that... it was simply to let you know that Andy was very much enamored with you, almost from the very first day he saw you, and I only wanted you to be aware that he may hit on you... that was all there was to it!"

She seemed rather flustered now, "My God honey, I never dreamed that his meds would be screwed up so bad by that stupid Spanish Fly shit I gave... to... h-h"

I had never seen her like this, her cigarette fell from her hand and both of them were grasped around her head now. Softly, she had begun sobbing, as if not sure what she should do, only knowing that she felt responsible somehow. This wasn't at all what I'd wanted to have happen, I had only seen the superwoman, that never seemed to have a worry in the world, and she was now sobbing and I couldn't figure out what needed to be done for her, I only knew I had to do something!

"Cindy, I..." I said tentatively, "Look, as the Doc said, it just wasn't anyone's fault, and you can't allow yourself to feel like it was!"

She seemed to calm down a little, but as I looked down at her, I saw a frightened little girl staring back, so I immediately moved closer and put my arms around her.

"Ok, I think I understand a little better now," I continued, "so your warning was a very simple little 'FYI' to let me know Andy liked me a little more than he was letting on, right?"

"Yes, oh yes Joscelyn..." she was starting to recover now, "never in my wildest nightmares could I have seen what was going to actually happen to you!"

"Alright Cindy," I continued to try to make sense of things, "now let's talk about what you have tried to talk to me about for a while now, specifically Mel, her wanting me for a Mistress, and of course, the Sisterhood."

After a small sniff and a large intake of air, she began, "Well... The Sisterhood is modeled along the lines of a large political organization. Each branch is run by a quorum of matriarchs, who decide what happens to the money taken in, hands out rewards and penalties, and decides how any particular member rises within their ranks. When you are asked to take on a party that finds itself in need of a Mistress, you will take care of their needs, then produce a bill for services rendered that must be paid directly to the Sisterhood. There can be no other method of payment or recompense. Understand?"

I had listened carefully, and yet it was still a lot to deal with, so I replied, "Yeah, but that sounds just a little like an escor..."

"Ah! Careful there," Cindy said in a warning tone, "It's nothing like an escort service. In fact, it's closer to a whore house in certain respects, since sex during the performance of your duties is a given. However, the funds we receive are used to help us keep our members well dressed, and as sexy as possible, along with the setting up of S&M sex clubs within the city where the branch resides. These clubs give you an absolutely private place in which to conduct your business, built to the highest standards with fully equipped dungeons, and other types of helpful resources for your use."

As she took a break to zip up her jacket, I took a chance to ask what I thought was an important issue, "But is the Sisterhood the only ones to get any money for this work by the Sisterhood's members?"

"Yes... and for a very good reason," Cindy continued, "They allow us to continue to do what we love, without interference by local, state, or even federal police. We can hold our sessions in complete privacy and without any unwanted interference. It allows the session's Mistress absolute control over the scenario, in a much more powerful way than they could ever have been able to create on their own. As a Mistress of The Sisterhood, you will be the only power in their universe"

"Wow..." I was only now starting to see the advantages, "But what about the Mistresses, don't they ever feel like they should be getting some of the money?"

"Oh, Goodness no!" She laughed, "Because they get 100% of all tips generated during their scenarios. And that's a pretty good haul, of course some parties are better tippers than others, but it's stated in the contract that tips are considered mandatory. No Joscelyn, The Sisterhood is an extremely well run organization, and all these issues were pounded out years ago, anyone in the S&M 'lifestyle' that wants the very best always knows who they can call."

There was a small pause as I digested the info, and Cindy watched my reaction.

I decided it was time to make my needs known as I said, "So what are the other matriarchs upset with you about, as far as I'm concerned?"

Cindy's eyes narrowed as she spoke, "What are you talking about?"

"I've heard that the Matriarchs have problems with you bringing me up to speed so quickly, or have I heard wrong?" I asked tentatively.

She sighed and said, "Yes, I don't know how you found out about this, but I've been running into some interference in bringing you on board as a novice as quickly as I want to. You see, The Sisterhood requires a fairly long waiting period for novices before they can even take their initiation, and they must have gone through a complete test on how to conduct themselves when in a scenario."

"And the other Matriarchs," I continued, "are not willing to allow me to do this test quite yet?"

"I'm afraid not Joscelyn," Cindy said, "and there doesn't seem to be a way around it just yet. So we'll have to wait for a while, hopefully not too long!"

"...and you're trying to bring me in quickly for Mel?" I asked.

She gave me a knowing look that answered that question pretty quickly.

"Alright, then we'll all just have to wait!" I replied, when suddenly I remembered Dolores' request, "Oh shoot, we gotta get everyone to dinner, or Dolores will kill me!"

We quickly got up and ran upstairs to wake Andy and Mel up from their naps, and then I went down to give the Doc a heads-up that dinner was ready.


Dinner was a rather subdued affair, nothing like the previous night's banquet. But then we were all pretty tired after going through the emotional ups and downs that Andy's problem had caused. But when it came to Andy, he seemed to be coming back to his usual hyper self, and that was a really good thing for me, as I began to more fully understand who the 'real' Andy was.

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