A Learning Experience Ch. 03

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Joscelyn2tg
Joscelyn2tg
226 Followers

"Okay, I'm being selfish, it's your turn," Mel finally said, "you get under the water now." I slid around to the front of the shower, and we were back to back for a minute. Our wet slippery asses rubbed together as we squeezed by each other in the narrow stall, as it seemed like long arcs of electricity shot up my spine. I was now standing under the water, and Mel's hands were working my shoulders.

"Oh, that's awesome," I moaned. Mel's hands weren't just pretty, they were also strong, as well as warm and sensual. As she started to caress my ass, I moaned even louder. I was so turned on now, I wanted to rub my own breasts and nipples, but that would have to remain a future fantasy for Joscelyn, and I held back from saying anything.

Both of Mel's hands were on my waist, rubbing up and down my sides. Suddenly she slipped her hands around my front, and started to caress my chest. She held my nipples between her fingers as I moaned loudly and leaned back into her. I could feel Mel's breasts against my back. Then she began caressing my semi-hard cock, her hand closing around the shaft, stroking it slowly under the stream of hot water. I moaned to her touch, leaning back to give her better access, and soon I was fully erect. Finally my desire for her warm pussy was too much to deny, I touched her wrists and she stopped mid-stroke as I spun around in place and drove her against the wall of the shower. There could have been no doubt by the look in my eyes right then, I was ready to rock her world, in fact... I was way 'past' ready!

I grabbed her butt cheeks and pulled her into me completely, then drove her once again into the hot shower wall. Sensing that I had her supported, she then wrapped her legs around me and begged, "Oh... fuck me... fuck me baby, please... hard... harder!"

I'm not sure how soundproof that bathroom was, but my guess would be that even Dolores downstairs could hear Mel this time. In any case, we both climaxed almost at the same time, and we were both also extremely clean as well.

I got dressed in a tan leather western-look shirt with a tie-close top and jeans, before asking Mel if she needed anything, when she said no, I told her I was going down to get some breakfast, then I'd talk with Dolores for a while, hopefully before Andy's dad got home. I said I would see her later and kissed her before leaving the bedroom.

Some of what I was starting to remember from last night was Mel's story of her rather traumatic childhood. She lost both of her natural parents in an auto accident before she had even started school, something I couldn't even imagine having to face. Her maternal grandparents then raised her until her grandfather had to be placed in a nursing home after a bad stroke, and a couple years later, her grandmother died from cancer. Her grandparent's best friends were their next-door neighbors, and their oldest daughter was, none other than, Cindy! Apparently Mel was 16 when her grandmother died, and she had set it out in her will, that if she died before Mel reached legal age, she wished Mel to be adopted by their best friends and neighbors. Because they had no other relatives that lived in the same state, this would allow Mel to finish her high school years without having to start over in another state and another school. And that's how Mel and Cindy knew each other; they were sisters, legally if not biologically.

Apparently Cindy's history was almost as traumatic, having run away from home at 17, forced to become a street walker and addicted to heroin before she was even 18. Now clean and sober from it for two years, she has been gradually 'coming back', and even decided to get an associate's degree in accounting, along with her 'sister' Mel. The two girls, who were always close when Mel was first adopted by Cindy's parents, had become inseparable now. Even though there was an eight-year difference in their ages. We had talked last night about their lives for hours it seemed, and I now felt so much closer to both of them. But there was still something about Cindy that made me worry, and it was starting to affect me, sometimes sending my anxiety level sky high!

As I got close to the kitchen, I could hear Andy and Cindy laughing about something, and assumed it was probably me! Although I might bitch about it, I didn't really mind that they liked to laugh at some of the things I did, as I had pretty much always been a 'class clown' and Andy knew that about me as well as anyone. And just in case that had ever needed any verification, I'd certainly been doing plenty of crazy stuff lately!

As I walked in, Andy came over and hugged me, then asked, "Are you feeling better now Jack, no more hangover?"

"No, not a bit of it left, Mel's hangover remedy really works!" I replied, then remembered the question I wanted to ask earlier, "Hey, I forgot to ask you, I thought only you and I were coming out here, when did the girls decide to come?"

"It didn't appear you minded Mel being here this morning!" Andy laughed.

"Oh no! No complaints, it just seems like it will be pretty boring here for them, that's all

"Oh... Well after you blacked-out last night, Mel insisted she come along, and so I thought, why not make it a foursome?" he replied.

Cindy now got up to give me a hug, and a kiss on the cheek as well, saying, "Besides, I thought if there were any chance that Joscelyn might show up, then I wanted to be around to meet her!"

Her kidding then changed over to genuine excitement as she added, "And I did enjoy meeting Joscelyn this morning. Do you think she'll favor us with another appearance anytime soon?"

"Well ya just never know. Apparently she keeps to her own schedule," I said.

"Ah ha! Mystery woman, eh?" she laughed, then asked, "Hmm, maybe I should see how Mel's coming along, she did say she was coming down, right?"

"Oh yeah, I'm sure she'll be down soon," I said, as we all stared down the hallway.

"Well, let's all sit down, and we'll wait for her," Andy finally replied.

As we were seated, Dolores came over to the table with four sets of table wear and napkins, then brought us four glasses of orange juice, fresh squeezed with crushed ice.

"So what's everyone hungry for?" Dolores asked.

Just then Mel walked in, "I could eat a horse!" she quipped.

Everyone laughed and Dolores went along with it, "Ok... got an order for one horse."

Eventually we all decided on French toast and sausage, and Dolores retreated to her kitchen, where she was a marvel to watch cook. And she wasn't too hard to watch in any case, with a dark olive complexion, brown eyes, and very long black hair, she could almost define the word exotic. At about 5'4", she was small featured but everything was very well proportioned. Andy noticed me watching her.

"Well, what do you think of Dolores?" he asked.

"She's very pretty and definitely knows her way around a kitchen!" I replied.

"Yes, yes she does. So would you ask her out, is she that pretty?" he asked.

This shook me up a little, but I said, "Well, yeah... don't think she'd accept though!"

"Interesting... very interesting!", he replied cryptically

Close to the end of the meal, I picked up on a little side-conversation going on between Cindy and Mel, I couldn't hear all of it, but I saw Mel show Cindy what looked like a little cloth tape measure, the kind they put in sewing boxes.

"...And look what else I found in her room," Mel said quietly, showing Cindy the tape.

"Uh... I hate to sound dumb, but... so?" Cindy replied.

"So... guess whose measurements I managed to get last night?" Mel asked.

"Huh... Oh! Oh My God that's perfect! You got 'em all?" Cindy asked back.

"Yep, every single last one we'll need... Can you say 'shopping trip'!" Mel said.

"Woo Hoo! Well done Mata Hari!" Cindy laughed, then turned her 'puppy dog' eyes on Andy and asked, "Andy honey? We need to go shopping, will you take us while Jack has his appointment with your Dad this afternoon?"

"Sure Babe, no problemo!" Andy responded with his usual glib phrase.

I assumed Mel had come out here on the spur of the moment, and didn't have much to wear. Then she found the tape so she could get her latest measurements and now she was asking Cindy to go with her and help shop for new clothes for the weekend. And she was probably thinking we were going out tonight, so I better ask Andy where we can go around here for dinner & dancing. I felt a lot better about all of the overtime that I'd put in last summer, it was already March, but my bank account was still flush!

Once we had all finished breakfast, Andy asked Cindy and Mel to go get ready for their shopping trip, and he would be up to get them as soon as his dad got there. After the girls had left, Andy got up and went over to Dolores and asked her to stop what she was doing for a little while, to come over and join us for a chat.

I wasn't at all sure what secrets Dolores held that Andy somehow thought I would be interested in, but I'd come this far, so I'd listen to anything, that anyone knew, that might help me to become closer to what I wanted to be.

"So Dolores, I think you've met my friend Jack," Andy said quietly.

"Yes, well, we ran into each other upstairs I think." she said with just the hint of a giggle, "I am sorry Jack, I wasn't laughing at what you were wearing, it was the look on your face that I couldn't help but smile at! Andy talks about you all the time, I really was so glad to finally meet you."

"Yes, I'm sorry about that, it was a little embarrassing, I don't usually sleep in a nightie. I'm afraid I'd had a little too much to drink last night," I explained.

Both Andy and Dolores gave me questioning looks, "Really... so that was the only reason you were wearing women's lingerie?" Dolores asked, then looked to Andy, who didn't look at her, and continued to stare me down. I knew what he wanted me to say, and I didn't want to say it in front of this beautiful woman.

But I'd done a lot of things recently that I didn't want to, so finally I said, "No... No, that's not true... well, its part of the reason, but the main reason is because I have had a desire to be a woman for most of my life, I'm currently waiting to see Andy's father in hopes of discovering what these desires really mean, and to see if there is anything he can do to help"

Andy was now beaming, he knew I'd taken a big step and he reached over and squeezed my arm to let me know. Dolores was smiling now too.

"In that case Jack, I'd like to tell you about myself," Dolores began, "I was born a male, my original name was Douglas..."

I think Andy had to pick up my jaw from the floor, since I can't remember closing it after it dropped like a rock from Dolores' total bombshell. She... used to be a guy... like... me? This gorgeous creature would be easier to confuse with a Brazilian Samba Queen, than an American short-order cook, she absolutely exuded femininity!

She then continued, "...We lived in Miami when I was growing up, it was a very poor area. My parents were extremely religious, and they had a really hard time with my wanting to be female. My mother realized how miserable I was and tried to help me the best she could. She bought me some female clothes and since my dad was gone a lot, I was able to wear what I wanted. But one day he came home before he was expected and saw me wearing girl's clothes and went crazy, hitting me and throwing me across the room, breaking a rib and my nose. A neighbor called police, and eventually my parents divorced because of it. Since there was a possibility of jail time for his assault, my mom got a very good settlement, which she used mostly to help me transition."

"Wow, I'm so sorry you had to go through that Dolores," I said, "well... the abuse, not your transition, you are so beautiful!"

"Aw... thanks honey, well Andy has given me a few bits and pieces of what you've been dealing with Jack, maybe not as much drama as mine, but it sounds like you have been very conflicted in dealing with it all, and that brings emotional pain." she said.

"Oh, I dunno, Andy's the very first person I've ever even told about it," I said feeling a little shy, "I guess he's the first that I ever trusted enough to tell this to. "

"I know my parents would absolutely have a cow if they knew I was about to talk with Andy's dad about all of this." I continued, "But I don't believe they would ever hurt me like that... well, certainly not physically anyway," I finished in a rather unsure tone.

"Look," Dolores said as she started searching her pockets, "here's one of my business cards, please don't hesitate to contact me at 'any' time if you need someone to talk to. Dr. Goldmann is my doctor too, and so you can always count on one of us being around if you have a problem, ok?"

"I hear ya, Dolores," I replied as I took her card, but held onto her hand, I couldn't believe this delicate woman had ever been a male, "and thank you. Thank you so much for sharing your story, and for letting me see you, and letting me see that someone so beautiful started out being a guy like I am. It means so very much to me!"

"I know sweetie! You'll be even prettier than little ol' me, you wait and see!" she replied, "besides, what matters is what's on the inside, the rest is window dressing!"

Just then an electric garage door opener popped on, and Andy said, "There's Dad!"

A few minutes later a tall, well-dressed man, with a hat and a briefcase came into the kitchen and searched the available faces. He seemed to immediately notice that his son needed a haircut, and after chiding him gently, said a warm hello to Dolores and then turned to me.

"Hello, and you must be the Jack that we all hear so much about," he said as he began to shake my hand politely, "And Andy's explained a little of your issues, apparently they lie somewhere along a similar path as our Dolores here, do they not?"

"Yes sir, I believe they do," I replied.

He suddenly realized that he still had on his driving gloves, and quickly yanked off his right hand glove, so that he could shake my hand directly. His moustache and van dyke beard were impeccably groomed, in fact everything about his appearance spoke volumes about his attention to detail. This was no 'absent minded professor', it was obvious he produced a high level of professional confidence wherever he went.

"Oh yes... Dolores, I haven't had a chance to eat at all today, would it be possible for you to throw something together for me, um... a sandwich perhaps?" he asked.

"Tch, tch! You never eat well during these conferences do you doctor?" Dolores commented, then said, "Of course, I'll bring your favorite soup and sandwich up in a few minutes, alright?"

"Ah, you're an angel my dear!" the doctor replied, then said, "And Andy... perhaps you could show Jack to my office, I'll be with him in about 10 to 15 minutes, ok?"

"Ok dad!" Andy replied, "Let's go Jack, lemme give ya the nickel tour..." he said as we both got up from the table and I followed him down a narrow hallway.

Like most Main Line, or old Philadelphia houses, their kitchen was always in the oldest part of the house, usually built anywhere from 1750 up to 1920 or so, which meant the ceilings were low. Because most of them were 3 stories, the bottom floor walls were massively thick. This left very narrow passageways through the old parts of the house. Once we passed beyond the old house's walls, it became much more open. We walked past the front door foyer, and then into another long hallway that seemed to connect with an even newer part of the building.

"This is the extension dad put in for his home office," Andy explained, "There are exam rooms, a small surgery, meeting room, a complete lab, pharmacy, and then down here a ways... is his office."

As we walked through the massive double doors into his office, I was struck by the awesome scale of this room. At its center was a large domed skylight window, that illuminated a large desk, that was so big it looked for all the world like some land locked aircraft carrier, and a bookcase return behind it. Off to the right, behind a low wall, was what appeared to be a sitting area, with thick carpeting, and very comfortable looking furniture. And to the left, also behind a little higher wall, was a more clinical looking exam area, with a tiled floor and glass cases filled with medical gear. On a wall behind the desk were many autographed celebrity photographs, and as I walked by them I had to ask Andy who they were to his dad.

"Oh those are some of his more famous clients, his specialty is sexual problems, and as you might imagine, Hollywood stars typically end up having some type of sexual issue that they need help with at some point in their careers," he explained.

"Wow, so they come out here to get help from your dad?" I asked.

"Well..." Andy replied, "it depends on a lot of things, but yeah, a lot of them do fly out here for visits, you never know when you answer the door here, just who might be on the other side, 'cause it could be someone famous!"

Andy went around flipping on lights, setting the thermostat, and turned on a big screen TV in the corner of the seating area and said, "The remote's on the coffee table, there's magazines in the rack over there... have a seat, and I'm sure he'll be here in just a few minutes."

"Oh yeah, hey Andy?" I asked, "I think Mel is worried because she came out here on the spur of the moment and doesn't have anything to wear if we go out. I thought it might be nice if we took them out, maybe tomorrow night. Maybe dinner and then out dancing? Anyway, here, I want you to make sure she can get whatever she needs when you take them shopping, ok?"

I had taken 10 hundred-dollar bills and folded them up so they were less conspicuous, and gave them to Andy as I said this.

"Yo dude!" Andy exclaimed, "Um, are you sure? I mean, my dad has credit accounts in stores he literally never even goes into, I'd be glad to take care of it for you, I'll probably be getting stuff for Cindy anyway ya know?"

"Yeah, thanks Bro, but I'm sure," I replied, "I feel bad because Mel felt she needed to come with us when I blacked out, and I'd like to make it up to her, just make sure she gets something nice, that she wants, but doesn't think she can afford."

"Well," he said, "I'll do what I can... you know women though... Oops, sorry, didn't mean anything by that. God, I'm gonna have to watch my mouth now!"

"Oh yeah?" I laughed back at him, "Well, you're always going to be my Bro, Bro! No matter what changes I may be destined for... ok?"

"Cool by me man," Andy responded, "That's ah... well that's how I feel too."

Once again he hugged me, and the hug lasted a little longer than I'd expected, but I was quickly coming to have strong feelings for this new 'brother' of mine, so that was fine.

"Well, good luck with dad," Andy said, "and I'll be back with the girls before dinnertime anyway, I'm sure they'll be hungry and tired after shopping!"

"Ok Bro!" I said, "I'll see y'all then!"

After Andy left, I wandered up to the cabinet next to the big-screen TV, I opened the cabinet doors and inside was a Sony U-matic videocassette recorder, along with a couple shelves filled with tapes. The titles all seemed to have sexual themes, and one especially stood out to me, 'Sadomasochism in the modern sexual relationship'. I looked around the room, and seriously thought about pulling that tape out and running it, but then thought better of it, it just seemed to go beyond a level of trust that I was trying very hard to establish with this doctor. Maybe another time.

"Ah! There you are," The Doctor said as he came around the corner, "I'm glad you're over here, take a seat and get comfortable, then I want you to fill out these forms for me, they are just standard medical request forms, so I can get your medical records. Also there are a couple of Q&A sheets that will help me understand your issues better, ok?"

Joscelyn2tg
Joscelyn2tg
226 Followers