Christy's Diary

By ChristyDancer

Published on Mar 23, 2023

Transgender

Sunday, September 22, Part 2

Just as I finished typing the morning's diary entries, Jason came bounding down the staircase to the pool. In "boy mode", I've been really close to Jason nearly all my life. He's been there for me when I really needed a friend. Last week, when he let me lay my head on his chest and accepted me as a "girl" friend, I felt really, really close to him. I've been thinking about him all week, and hoping he'd continue to view me as a "girl" and not a freak.

He was all smiles, and yelled as he got closer, "Hey, Christy! Who's your friend?"

"She's off limits, Jason. You wouldn't like her. She's mean and she treats people like a drill sergeant."

Brie just started laughing, and held out her hand, "I'm Brianna, but everyone keeps calling me Brie, even though I've told them I'm Brianna now. You can call me Brianna." She continued to laugh as Jason took her hand and made an exaggerated gesture of bowing and kissing her ring. In some ways, Jason reminds me of Chris Pratt, but from "Parks and Rec" days and not from "Guardians" days. I'm still wondering why what's-her--name from House Bunny ever dumped Chris Pratt. Anyway, Jason is funny and maybe a bit dumb in some ways but really smart in others.

"M'ladies, Miss Christy, Miss Brianne, and I see Miss Princess is out here keeping you all save and guarded. It is my extraordinary pleasure to make your acquaintances and to now leave you alone while I take advantage of Ms. D's pool." With that, he pealed off his shirt and dove sideways into the deep end of the pool.

"He's nice," Brie said. "Are you gonna fuck him?"

"Shut the fuck up, you filthy minded bitch. And I say that in the most loving and caring of ways, sister. You're a witch, you know that, right? I haven't even kissed him yet. For that matter, I'm not zactly sure what fuck him' means in this context."

"Oh, my innocent little sister, you newbie to the grand sisterhood, you'll find out. Next time I sleep over, we'll need to change your viewing patterns to something more `documentary' in nature."

I took my straw out of my Diet Coke and flicked it at her. She seemed to be enjoying my pain a bit too much.

"Anyway, Brie, why do you care? You're not into boys."

"I'm not PERSONALLY into boys, but I'm certainly a fan of conjugal activities of all kind, at least as a clinical observer."

"Oh, and Brie, did I mention, how the hell is someone with your vocabulary getting a C in English?"

"My vocab and grammar are just fine. My problem, such that it is, is that my interpretation of Jane Austin disagrees with what Ms. Harrigan was taught at Brown. I'm sure it is temporary,and I'll bring her around to my way of thinking soon enough. In the meantime, though, the focus of our attention this afternoon needs to be on your sex drive, or might I say, lack thereof."

Just then, Jason did a lap by us, clearly trying to show off. He rolled over on his back and spit water up in the air out of his mouth, imitating a whale. "Yes, Brie, why am I not completely turned on by .... That?"

"Well, my sentiments exactly, but speaking as your friendly neighborhood amateur endocrinologist, I think you should at least be getting a woody at the sight of a semi-clad, not half-way-decent looking fellow who is parading in his short-shorts around your pool."

I sighed. "Yeah, that's the problem. I know deep down inside I'm a girl, and when I visualize sex, I'm always taking the girl role with a boy, but even in `gay boy' mode, woodies never pop up."

She paused, "So, you've... never... experienced..."

I stopped her, "Not that I'm fully aware of. Like I said, I've woken up with some wet pants on occasion, and have the vaguest memories of having dreamt of me with a guy. Yeah, I'm meeting with my doctor tomorrow, and I'll ask him about that."

Just then, Jason came walking up, dripping wet, looking all the world like Chris Pratt, rubbing his ear with a towel and seeming to be unaware that he was getting water all over everything. "So, wuz up?" I just love guys' vocabulary.

Brie responded for the two of us, "Nothing's `up'. We're been busy doing girl stuff, you know, pillow fights, doing each other's toenails, more pillow fights. Stuff like that."

"Yeah. Dig. You gonna get in the pool?"

"Maybe. Trying to stay out of the sun. Pool yesterday and today. Don't wanna get burned. Maybe later, yay know?"

"Yeah. So, Christy, when were you gonna tell me you had friends like Brie? I'd been coming over sooner."

"You're assuming she's a friend, Jason. After what she's been putting me thru the past couple of days, `friend' may be off the table."

Brie popped up, "Jason, you know how our friend Christy used to be Chris, right?"

Jason nodded.

"And yet, laying before you here is a lovely specimen of 14, almost 15 year old ninth grade girl, wouldn't you agree with me?"

Jason continued to nod.

"So, Jason, may I call you Jason? Anyway, Jason, someone has to take credit for the amazing transformation that has occurred in just a scant few days. Now, I don't want to take ALL the credit, but then again, Leonardo DaVinci didn't carve Mt. Rushmore all by himself, right?"

Note to self: Never cheat off Brie on an art history test.

Jason, nodded, "yeah, I wasn't gonna say anything, but now that you've brought it up...". He did that sort of dumb-ass pause thing that can be kinda cute sometimes. "Look, I've known Chris... Christy... whatever... for a lot of years, and always figured him... her... was a gay guy, and I was cool with that. Then, when he... she... told me about this, well, I was even cooler. I mean, whatever floats your boat, right? I like her, and she's my friend, and... well... yeah, she's beginning to look hot as a girl. Am I saying this right?"

I started to blush. I don't blush, but dammit I was blushing. "Yeah, Jason, you're saying it right, and yeah, I really need you as a friend right now."

"Well, you got it. Now, I'm getting back in the pool, and you two can go back to doing girl stuff."

As Jason walked away, Brie turned to me and said, "You're blushing. You're really blushing. You like him. You really like him!"

Just then, Jason turned around, walking backwards, and yelled, "By the way, Christy, your swimsuit looks good on you."

I told her about last weekend and how I'd spilled my guts to Jason and how he put his arm around me and let me lay my head on his chest. Brie started fanning her face and with a mock-Scarlett O'Hara accent proclaimed, "Oh my oh my oh my, Miss Christy, whatever are we going to do with you! I do believe that boy over there may want to slide his lil' ole dick in yo mouth, I do believe."

"Give it up, Brie. I'm NOT practice BJ's on my best friend," I said out loud, while secretly trying to visualize exactly what that might look like.

The rest of the afternoon was mundane. Brie and I actually swam a bit, just to say we had. We uber'd in some Indian Food for a late lunch, and it sucked. It was nice to just join in girl mode' with out my girl mode' being the topic of conversation. For a bit there, I actually forgot I'd ever been a boy, and just felt more relaxed than I ever remembered feeling. Everyone started getting lazy and bored by mid-afternoon. Finally, Aunt Lilly said something about an early day at work tomorrow, and how Jason still had homework. Brie and I finally worked on our homework (the reason for her being here in the first place) and then Mom and I carried her home. After a while, it fell to a dull routine.

Mom then asked me, "So, you're wearing that cute little romper and a sweater tomorrow. What shoes are you going to wear?"

I said, "I guess just my white tennis shoes."

"Do you have any socks? There are some cute white ankle socks in Becky's room. You should fetch them before you go to bed, and put everything together in a bag for tomorrow."

I nodded, and told her I was going to make it an early evening anyway. I padded upstairs, and started rooting around in Becky's room. I knew where she kept her socks, but curiosity got the best of me, and I started rooting thru her lingerie drawer. After all, I figured, she and I are nearly the same size in everything except her bras, maybe there's something here I can `borrow'.

Down near the bottom, I saw something odd. I pulled her stuff aside, and there was a little plum-colored plastic bag. I KNEW it was none of my business, but I had to look. Inside, it was... huh... a penis shaped vibrator! It was big. I don't mean BIG big, but certainly full sized -- maybe like 6 inches long and with a ball sack under it. There was a little switch near the base, and it both vibrated and did sort of a `contract-expand' thing. I'd never held anything like it, and had seen some packaged ones at Martha's place a week ago. It had a very life-like looking head, and while the only penis I'd ever felt was my own, this one wasn't even in the same universe as mine. I had no idea if it felt natural or not. I was afraid Mom would catch me rooting around, so I ran back to my room and stuffed the bag in my own undies drawer.

I changed into a little yellow striped sleeveless shortie pajama set, and remembered to take off the remainder of my makeup (most of it had washed off in the pool and the shower afterwards) and to moisturize everywhere before hopping in bed. I read a little bit, then thought more about Becky's vibrator I'd found. I could only IMAGINE her using it, and that gave me a shiver, but I decided to get up and dig it out anyway. I went back into the bathroom and scrubbed it off, just in case she hadn't, and carried it back to bed. I wasn't really interested in the vibrator part of it, but more the `taste' part!

What did a penis -- even a fake one -- feel like in my mouth? It wasn't an erotic thing, but more of a scientific experiment. I started by licking the head, and it didn't really taste like plastic. In fact it tasted almost flesh--like, and was soft but firm underneath. All I knew about this was what I'd seen in the very few pornos I'd watched. I had a vision of one girl I'd watched, who had a whole series of videos treating blowjobs as an art form.

In most of her videos (or at least most of the few I'd seen), she was on her knees with the guy standing in front of her, but in a few, the guy was laying down and she was laying kinda in the opposite direction, with her bottom in the direction of his head, not "69-ing", but laying or kinda kneeling sorta beside him. She would start with a soft penis, and then massaging with her hand, she would kiss and lick the entire shaft until it started getting hard. She would do a combination of stroking with her hand and pumping up and down with her mouth, taking about a third of it in her mouth and leaving enough room for her hand to continue to massage it. Most of the guys she blew were about 6 or so inches long, and she could get her fingers around the shaft enough to stroke and massage them. I know it was acting, but it would usually take her about 6 to 10 minutes to `get them off'. When she knew he was about to squirt (how did she know???), she would move her hand down to his balls, usually, and then take as much of the shaft as she could in her mouth. I remember one where I could see a little bit of his man-juice leaking out of the side of her mouth.

So... whew... with that in mind, I rolled over on my left side, cuddled up to a big pillow, pulled the covers up over my head, took Becky's vibrator in my right hand, closed my eyes, and lowered my mouth onto it. Because it wasn't attached to a guy, I couldn't really stroke it the way I'd seen in the porno, but I could at least hold it in my hand and massage my fingers, and gently stroke the `penis' in and out of my mouth.

I was surprised at how natural it felt. I was worried that my teeth would get in the way, but my mouth seemed to be naturally built for cocksucking'. I caught myself smiling thinking about that word -- cocksucking'. I was now an unofficial cocksucker. LOL.

I put all those thoughts aside, and tried to focus my attention on the task at hand. I found myself relaxing, and my thoughts wandered to some of the guys I might want to be sucking. Josh Hutcherson. Liam Hemsworth. I even had a visual of Jason in my head. I could see their faces even though my bed was down on the fake penis.

My entire body was wrapped around the pillow, and my legs tucked up against it. Before I realized it, something really strange was happening. My GOD! Was I getting a woodie!?! This didn't happen to me. Ever. But there it was, a little bittie hardon. Me. I was unconsciously rubbing it thru my satin panties and shorts and into the pillow at just about the same rhythm I was sucking the fake penis.

I was in a complete daze. I don't know if it took a minute or 10 minutes, but suddenly I was quivering all over and felt my panties getting wet. I unconsciously tried to jam the entire vibrator into my mouth, as far as it could go, and imagined that the wetness coming out of me was actually coming out of the shaft in my mouth. I imagined the `guy' and I were having simultaneous orgasms. Oh GOD! I was breathing and squirming and trying not to cry out, because I knew Mom was right down the hall and would hear me. I lay there breathless, my mouth wrapped around the cock and my legs wrapped around my pillow. I could feel my own wetness soaking my panties and seeping out into my pajama bottoms. I lay there in my own wetness for what seemed like an hour.

After a while, I drifted in and out of sleep. I had never felt such a thing. I got up and went to the bathroom to clean myself up. I got some fresh panties and went back to bed. Even my pillow was wet, so I moved it aside and snuggled up to one of the other pillows.

I kinda had a feeling I was going to have to tell Dr. Strange about this tomorrow. I could only wonder where this was going to go, but I was sure I was going to want to do this again.

Next: Chapter 12


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