Growing Up Ch. 02

Jaimie was exploring Jane regularly now. He had started thrift shopping with his friends, and they would help him with sizes, styles they thought looked best on him. He no longer pretended it was just "Halloween fun", but a secret that was going full bloom. Some nights, when he knew his parents would be out late, he'd get dressed, work on his makeup skills, and get Charlie to evaluate them. Jaimie was pleased that Charlie never judged, and gave helpful tips on what he thought worked, or didn't work. Jaimie's confidence grew, and he was able to talk Charlie into taking him out, "On a date", so he could work on his shyness. The previous Halloween let Jaimie know that he COULD be seen as a girl, but sometimes doubt would creep in.

Then, too, was Jaimie questioning to what end he was doing this. He still longed to have a girlfriend. Would that ever change? Would the fact that he'd never HAD a girlfriend, or even a DATE with a girl sway him? He had to admit, it was making him question his future. He'd never had any interest in guys, and the ONLY exception to that was the way he felt whenever guys looked at him as Jane. He could NOT deny, being desired WAS exciting. Why is it always so easy for girls?

Anyway, Jaimie was enjoying his time as Jane, becoming more outgoing. Charlie was more than supportive. Jaimie had even overheard Charlie talking to Mom about him, saying that she had to realize That Jaimie would never be what Dad wanted. They needed to work together, to make Dad understand that He needed to be himself. She agreed, having realized it long before. She just hadn't been aware that Charlie was helping.

A few months after my 18^th birthday, Charlie sat me down and told me that he had set up a date for me. He had a friend who was Bi, and thought it would be a good way to "explore" my options. I protested, telling Charlie that I wasn't gay, again. He said he knew that, but, (as he held my hand) that I wasn't really a guy, so it's not gay. I'll admit, I'd had this conversation with myself, a few times. I agreed to go, but told him I was certain nothing would happen.

Mom came to my room a day after, and told me that she felt that I would be making changes in my life, now that I was 18. She hugged me and offered support. She told me (as she didn't know I had overheard the conversation with Charlie) that she and Charlie would help Dad understand. Mom had a tear in her eyes, but smiled and told me that she had always wanted a daughter. THAT was an eye opener. She told me that Charlie let her know about my upcoming "date", and handed me two crisp hundred dollar bills. "To get a nice outfit, suitable for a date." Shit, this is getting real, can I do this?

The butterflies never left my stomach all week. Charlie took me shopping the Friday before my date, and urged me get a blouse that showed my cleavage, a sexy lace bra, a skirt shorter than anything I had worn, and a beautiful pair of stiletto heels. Mom had instructed him to take me to a salon, where they plucked my brows, cut and styled my hair even more feminine way than I'd wore it as Jane, and gave me makeup tips. When I got home, Mom instructed me to dress, a bit conservative, for dinner tonight, as she would be introducing her daughter to Dad. PANIC time!

No amount of pleading would sway her.

I picked a knee length dress, low heeled shoes, and tried, futilely to get my breathing in check. Charlie and Mom were talking to dad while I changed. I know my legs were wobbling as I walked down the hall, through the living room, and into the dining room. Mom looked up, smiled and said, "Dear, I'd like to introduce you to our daughter, Jane."

I stood there, fidgeting, watching his eyes. They went wide, his mouth dropped open. It seemed like forever, when Mom started to talk. Dad held his hand up to stop her.

Charlie, Mom, and me, all watched as he pushed away from the table, walked over, walked around me. With a sigh, he said, "Well, I guess I knew this was coming." Another pause, then he softly put his arm around me. " I guess this life has been tough on you, living in your brother's shadow, Jaimie...I.. mean, Jane. I- I'm sorry that I made it harder. It is easy to see that this is more you than what I tried to make you." With that, he leaned down, kissed my cheek. "You'll have no trouble from me." He looked up, smiled and said, "Well? Let's eat!"

With that we exhaled.

As we ate, he made little jokes, about being sorry we missed the Father-daughter dance, and how he will have to pull out his baseball bat, to keep the boys away. I know my smile covered my face, but no bigger than Mom, or Charlie's. The firestorm we expected never came. I guess we under appreciated Dad's grasp of reality. The conversation came up about legally changing my name, and when to do it. I said I'd be more comfortable AFTER graduation. It seemed the easiest. NOT going through even more harassment than was usual, at school. We we mentioned the "date", Dad asked if I needed a chaperon. We all laughed, and I assured him, I didn't.

The next morning, Dad insisted that we all go out to breakfast. He wanted to get used to having a daughter, and, as he put it, show off how pretty she was. "SHE"...I'll have to get used to that. A couple of weeks of school, as Jaimie, then? I guess I'll be "she." That evening, I put on my new clothes, worked on my makeup. When I stepped out, Dad raised his eyebrows. "THAT'S what you are wearing on this innocent date?" Then, he noticed the cleavage. "Y-You have..BOOBS? When did THIS happen? Real ones?" I guess he thought I was wearing silicone breasts, before.

"Yes, Dad. They've been growing for a couple of years. I had to wrap them, to keep them from showing."

He was having a hard time trying to keep from staring. "I guess you really ARE my daughter. Somehow, I thought...those... would come later. And...that skirt, it um, doesn't cover much. Are you SURE Me or Charlie shouldn't come with you?"

I laughed, and hugged him. "Thanks for being a protective Dad. Charlie has been doing that for quite a while, but I'm ok. Charlie assures me that his friend is ok."

Mom pulled me aside, and handed me a purse. "I didn't see a purse in your things, and you'll need something to keep your phone, ID, and money in. " Then whispering, "Keep your legs together, Honey!" Giggled and swatted my bottom.

"MOM!!! " I blushed. I never imagined Mom would make a sex joke. There was a knock at the door, and I stiffened. Crap, this is it, my first date. With a GUY. Was I ready?

I went to the door, opened it, and there stood Lester. He was nice looking, taller than Charlie, but about the same build. He smiled wide, and said, "Wow, Charlie said you were hot, but...I wasn't expecting this!" I turned back to look at Charlie. So did Mom.

"Hot? Charlie? Really?"

"Well, Mom, come on, she IS, right? Help me out, Dad. Isn't she?" I blushed and Dad shrugged his shoulders and nodded.

"Men! I swear!" Mom shooed me out the door, laughing. "Have fun, Jane. Don't be out late."

Lester walked me to his car, opened the door for me, then went to his side. As he buckled his seat belt, his eyes went immediately to my mostly exposed legs. I flattened out my skirt as much as I could and crossed my legs. Lester made small talk as he drove, subtly glancing over to me. " So, first time out?" It took a second to register his question. "You look amazing"

I cleared my throat and answered, "No, I've been out several times, just...not with a date."

"Ah, ok. I wasn't sure. Charlie thought...maybe I'd be the person to... um...help you...transition into... being a girl. You know...since I...like both."

I swallowed and nodded. Lester was a perfect gentleman, I couldn't imagine anyone being kinder. We ordered a nice dinner, I got to have my first alcoholic drink, legal drink, that is, and I really was enjoying this more than I anticipated. After dinner, he took me to a club, and, though I was nervous, got me to dance. After my third drink, and several dances, jokes, etc., I was completely comfortable. On some of the fast dances, Lester would get behind me, and grind against my ass. At first I pulled away, but eventually started pressing back into his crotch. On slow dances, he would cup my ass with one hand, and press me into him so that I could feel his cock against my stomach. There was no doubt that he was horny, and I admit, I was loving the attention, and also the looks from other men watching us dance. After our fourth drink, he asked if I'd like to go back to his place. He was in college, like Charlie, but had a studio apartment over his parent's garage.

Instead of opening my door, he opened his, and motioned me to slide to the middle. When he got in, and we buckled up, his hand went to my thigh. I leaned my head into his shoulder, my hand on his chest. As his hand eased up my thigh, pushing my skirt higher, my hand dropped lower, into his lap. He sighed and pushed up slightly. I knew what I was going to do. To me, it was the least I could do, and, if I'm being honest, I was pretty turned on. I kissed his cheek, his neck, as I unzipped him, and fished his very hard cock free. My head followed my hand, and I licked his enlarged head.

He moaned, and tried his best to concentrate on driving. I opened my lips and slid down on his pulsing cock, running my tongue around it. The hand that had been on my thigh went to my head as his fingers combed my hair. He was breathing harder and said, "This CAN'T be your first time doing that! I don't think you're as innocent as Charlie thinks." I kept sucking until he arched up, and blew hot cum in my mouth.

I made sure I got every drop before I raised up, tucked him away, and rezipped him. I kissed his cheek again, and whispered in his ear, " I have done that, a few times, and Charlie doesn't know...yet. I plan on telling him, though. If you would, take me home, please? I know, um...you probably wanted more, but... I HAVEN'T done that, yet, and, um...it has to be with someone special. I WOULD like to date again, though, if you want to."

As he stopped in front of my house, his eyes studied mine. " I understand. I had a good time, and am looking forward to...more. You're more than I expected, truthfully. Let me know how that 'special date' works out. He's a lucky guy."

He stepped out of the car, pulled me out, and I hugged him. I tiptoed up, pulled his head down, and got my very first kiss from a man. "Thank you for a lovely date, Lester!" And I did my best runway walk down the sidewalk, to the door. I stopped just long enough to refresh my lipstick, figuring Mom might look for telltale signs. I went in, and, sure enough, Mom was sitting on the couch, reading a book.

"Hi, Honey! How was the date? Did you have fun? I'm so glad you didn't stay out too late. Your brother is already home, too. I think, though, that he had a few drinks. He's already asleep." I told her about the date, that Lester was very sweet. I did leave out the last part of the date, though. I'm not ready to have conversations about sex, with my Mom. I told her I was excited to have that first date behind me, that it was easier than I imagined. Clearly, she had just been waiting up on me, and rose to hug me, and say goodnight. If she suspected anything, she didn't say so.

I went to my room, waited a few minutes, until I heard no movement from Mom and Dad's room. Charlie's bedroom and mine were joined by a bathroom. We had never locked those doors, which, had come in very handy for me. You see, I figured out, over time, that my "vitamins" weren't just vitamins. I researched what they were, and what they did. I'll admit, at first, I was furious. It took maybe 3 weeks for me to realize that Charlie was doing what he thought was best for me. Maybe it's weird, but, I loved him even more for it. Every time I looked at Jane in the mirror, and especially my breasts, that he was just guiding me. When I noticed that Charlie would come in drunk, and passed out, I began to explore.

At first, being really nervous, I would sneak in, pull his covers down, and look at his cock. Since mine was small, and hadn't gotten stiff in at least two years, I was fascinated that simply running my fingers over his cock made it jump and grow. With Charlie passed out, I could explore, and no one would be the wiser. The more I did, the more he responded. The third time I tried it, I pulled his cock completely free, and ran my fingers up and down it. I needed to know, IF I was going to be a girl, what I'd be dealing with. I almost had a heart attack when, as I was stoking it, he moaned and said, "Damn, Alison, that feels good. Come on, Babe, suck it for me." Clearly, he was dreaming. He had dated Alison a couple of times,and must have had fun.

Could I...do it? SHOULD I? I was never going to find out, any safer way, if I liked it or hated it. So, I took a breath, licked his cock slowly, watching to make sure he didn't wake up. He was moaning more, pulling my face down on him until I thought I'd choke. I could feel him grow harder in my mouth, and he pushed me up and down on it faster until he grunted, and spewed cum until some came out my nose. I swallowed several times and licked him clean. I could not believe that he didn't wake up. Since he didn't, though, I took advantage of every time he came home drunk, to figure out what he liked. I grew to LOVE the tingle that his cum made my tongue feel. When we were together, alone, it was all I could do NOT to tell him.

So, back to tonight. You've probably figured out, that special guy, to make me a girl, is passed out in front of me. I'm still dressed, except for my panties. I brought some cocoa butter, for lube. I crawled between Charlie's legs, pulled his cock free, and sucked him enough to make him very stiff. As he's done that past couple of times, he's moaning, this time calling me Eden. Oddly enough, Eden looked enough like me to be my sister. My heart is racing, but I pulled my skirt high, raised my hips over his stiff cock, and am trying to ease down on him. I won't lie... When his head popped in me, it was a shock. Damn, I mean that hurt!. Stll, though, I'd read enough stories, it's kind of a rite of passage. I took a deep breath, and slowly eased down.. God, does EVERYONE do this? He feels HUGE in me. He's stirring a little, and I'm trying not to wake him, His hips are moving, pushing upward. FUCK! Yes, it's big, but smooth and hot and hitting places in me I didn't know existed. It's all I can do NOT to moan, And I think I'm having a heart attack as his eyes blink open. SHIT!

His eyes went wide, he blinked several times, I guess to make sure what he was seeing, feeling, was real. " Oh, Eden, fuck you feel good!" Then blinking, focusing, his mouth fell open. "Jaime! Uh...Jane! Wh-What? You..what the fuck! we...CAN'T!" I used one hand to cover his mouth, afraid he'd wake Mom and Dad. The other, I used to pull one of his hands to one of my boobs. I continued to ride him. He might have been freaked out, but his cock wasn't.

"Shhh, Charlie. I...wanted this, NEEDED this, to be with you. You had to be my first. " I slowed my attack on his cock, and just sat filled, while I continued whispering. "Charlie... I know, I've known, for a long time, about my "vitamins". I was mad, but grew to understand you were just helping me, that I'd never be a normal guy, but might be able to... well, be THIS. I've known for a year that you'd be my first. Just like you were my first blowjob." His eyes widen again, and he tried to speak, but I held my hand on his mouth."Yes, Charlie, when you'd pass out, I...experimented on you. Those dreams you were having, about Alison, and Eden, was me."

"Oh, J-jane, I...I'm so sorry. I...this wasn't why I did it. I just wanted the best for you, I never planned on...on...THIS."

"I know, Charlie, but you helped make me Jane, and there wasn't anyone I wanted to make me a girl, more than you. So, shut up, and fuck your sister. She can't wait to feel you fill her up with your tasty (licking my lips) Cum."

With that, I started bucking on him again, and this time, he grabbed my hips, and pushed up to meet me. "God, yes, Charlie! Fill me!"

God bless him, he did just that, He came twice in me, before I came, myself, and lay on him, our hearts pounding. "I'm going to love being a girl, Charlie." As I kissed him, and fell asleep.