Chrissie: the New Girl

by T.S.Severe

Rachael Ross 1982 - 2012

Erotica Sex Story: What won't a boy do for the woman he loves? That's the question posed to fourteen-year-old Chris when his best friend's older sister, Jocelyn, catches the two boys jerking off with a magazine. Talk about embarrassing! But a little humiliation is nothing compared to what Jocelyn has in mind for them.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Reluctant   TransGender   Incest   Brother   Sister   FemaleDom   First   Oral Sex   Anal Sex   Masturbation   Petting   .


She was my best friend Kyle's sister and I was in love with her. There's a lot of reasons why and I don't just mean the obvious ones, like that she was almost eighteen, beautiful, and smart. I mean all the real reasons too.

Like, I couldn't have her, for one thing. Unattainable perfection, right? It hits every kid like a brick wall ten seconds after the onset of puberty. For another, I'd known Jocelyn since I was born practically, or at least since Kyle and I had become friends in first grade. Same thing. She'd been my babysitter for awhile, when I was nine and ten years old and didn't think I needed one. I hated being treated like a little kid and I hated being told what to do, but I didn't resent Jocelyn at all. When she told me to eat my dinner or do my homework, take a bath maybe and go to bed? Yeah. I liked it a lot. I wanted her to baby-sit me forever.

I loved her because she didn't love me. Like how could she? I'm about four years younger than Jocelyn is and when you're still a teenager, that's a lifetime. I was her little brother's friend, which made me a serious suspect. Every little thing that went wrong in her life, every time she lost her keys or couldn't find her hair brush, it was our fault. Older sisters are like that, I guess. I don't know. I'm an only child and I wished I wasn't everytime I saw her.

All I knew was that I loved Jocelyn and it was such a big secret that I didn't even share it with Kyle, and I told him everything. Except that.

It was raining outside and we'd done everything inside like a million times. We were just tired of everything, you know? I guess that's as good a reason as any for what happened. A couple fourteen year old boys who were already bored with life. Like we'd seen it all and done it all and washed the t-shirt twice. It sounds funny, but being fourteen pretty much sucks anyway.

We both wanted girlfriends, but we didn't know how to get them. Every time we tried talking to girls they blew us off. Not because we were ugly or retarded, just because they were thirteen or fourteen like us and didn't really want boyfriends. At least not boys our age. The younger girls wanted older boyfriends and the older girls? Forget it, they wouldn't give us the time of day. So Kyle and I mostly just talked about which girls were hot and which ones we wanted to have sex with and later that night I'd jerk off in my bed thinking about Jocelyn.

God! Fourteen sucked. It didn't help that I was so little either. Kyle was growing, his voice was already deep and he was a lot taller than he'd been just the previous summer. He was a good looking guy; brown hair cut short, brown eyes. Once he hit fifteen he'd get a girlfriend, I figured. That was like the magic number. But I was still just a hair over five feet tall and not even a hundred pounds yet. Like eighty-five maybe, with my blonde hair kinda long because my mom thought it was cute. I didn't mind that so much, lotsa cool guys have long hair and I wanted to be a rockstar if I ever got a guitar. My eyes are blue and I was a good looking kid, except I looked like I was twelve or something.

If I didn't start growing pretty soon, even getting over that fifteen year old speed bump wasn't going to get me a girlfriend. That was like the big birthday. Fifteen. A guy could get a girlfriend if he was fifteen, but not if he still looked twelve. I really didn't like myself very much. Physically, I mean. I wasn't all depressed or like gonna jump off a bridge, nothing like that. I just wanted to grow up and get a girlfriend. How hard was that supposed to be?

"Where the fuck's my tiara?" The door to Kyle's bedroom burst open and Jocelyn was frowning at us.

"I don't know," Kyle blinked at his sister.

"What's a tiara?" I asked her, trying not to stare because Jocelyn was dressed like a Princess.

She was beautiful anyway, but standing there on that rainy Saturday afternoon, Jocelyn looked ... beautifuler. She wore a pink gown, like a satin dress that a girl might wear to her prom or something, except it had been sorta altered. A mini-gown? The skirt was flared out and barely covered her perfectly round, firm ass. Her pussy too, for that matter, and I could tell she had pink panties on because I could see them as she moved. They were almost, but not quite the same shade of pink as her dress and I swallowed hard and tried to want to look away.

I didn't try very hard. Jocelyn's dress was tight around her thin waist and flat tummy and even tighter around her tits. Not really big tits, but wonderfully gorgeous breasts that I'd watch grow between the summer she'd been fourteen and the spring she'd been fifteen. Jocelyn had been so stressed about her tits and by the time she hit sixteen they were big, firm, swollen, and ... Wow! Jocelyn's tits. And her eyes were flashing. She had blue eyes, dark like sapphires, and mostly they were cold, but when she was pissed they got shiny and lively and caught the light so they flashed. She was pissed now and her long black hair was pinned up and her lips were red and her high cheeks flushed.

It was like meeting God. Like how I couldn't really do anything or say anything. I just mostly wanted to do whatever she told me to. Seriously. I'd have done anything she asked me to right then. Jocelyn was what a woman was supposed to be, to my mind. Everything I knew about girls? I learned from watching her. I just couldn't remember any of it when she was around.

"My crown, Chrissy," Jocelyn stared at me and I swallowed hard and she knew I hated to be called that. My name's Christopher, or just Chris, but I wasn't going to tell her that. I never did.

"Oh," I said and she rolled those dark eyes and pursed her lips, deciding that we probably were innocent this time.


Jocelyn never opened a door slowly or closed one gently and she had special powers. Real ones too. Her parents, my best friend Kyle's mom and dad? They never got mad at her. She could slam doors all night and they'd just smile and shrug and say that was Jocelyn being Jocelyn. She went where she wanted, when she wanted, and with whom she wanted. Or so it seemed to Kyle and that's how he explained it to me and I believed him. She had a little red sports car, her own credit cards, and two celphones. Jocelyn was beautiful, a lot more than her mom was. She didn't get her good looks from her dad either. He was an okay guy and Kyle looked normal, but Jocelyn was like from a whole other gene pool.

"She's adopted," Kyle said as we stared at the door. He was the only person on the planet totally unimpressed by his sister. Or so he pretended, but just being able to do that much was sort of amazing, I thought.

"Did you take her thing?" I asked him. "That tiara whatever?"

"Nah," he grinned at me. "I shoulda taken it though. It's that crown she got for being Miss Teen Seattle."

"Oh, she'd kill you, man," I laughed, feeling pretty relieved that Kyle hadn't taken it. Jocelyn woulda blamed me too.

"Yeah," he shrugged, tossing his comic book aside.

"What's she all dressed up for anyway?"

"She's just getting ready for some Halloween party."

"But Halloween isn't until Tuesday," I said dumbly.

"Duh! She's just getting ready. I told you that," Kyle said. "Hey, check this out..."

Kyle had a porn magazine and he'd been wanting to save it for later because he knew it was cool, but we were bored and he couldn't wait. It wasn't all that big of a deal. We had internet, so it wasn't like I'd never seen that stuff before, but I hadn't seen a lot of it. Just the spam that got past the child filters, so holding a magazine and being able to check it out was pretty cool.

"God, these chicks are hot," I said and Kyle agreed with me.

We flipped the pages and didn't really say a whole lot. My dick was getting hard and I squirmed a little, Kyle too and he was rubbing at his. That was sort of weird, being next to my best friend while he played with his dick through his pants, but those girls were showing everything and pretty soon I was rubbing mine as well. Kyle didn't care and after maybe fifteen minutes he grinned at me.

"What?" I asked him.

"You ever jerk off?"

"Yeah," I admitted, kind of reluctantly. "Why?"

"Me too," Kyle nodded. "I'm gonna jerk off."

"Where? Here?" I blinked at him. "Now?"

"Yeah, why not?" he laughed as he started undoing his jeans. "It's my room anyway."

"Yeah, but..." I swallowed hard because the only time I jerked off was at night in my bed, with the lights off. "What if your sister comes back?"

"She won't!" Kyle rolled his eyes. "She's busy doing her costume thing. She never comes in here."

"She just did!" I laughed at him.

"That's my point! She was in her already, so it ain't gonna happen again. Think about it." Fourteen year old logic, Kyle and me were good at that.

"Oh man," I frowned because I was always thinking about Jocelyn, and I really didn't want anyone to see me jerking off. Especially her!

"My balls are gonna explode, dude!" Kyle grinned at me and he had his pants all the way off and then he was pushing down his underwear.

"Oh man," I repeated needlessly, looking away even though we'd seen each other naked like a thousand times. This was different though and I'd never seen Kyle when his dick was hard, but it was now.

"Everybody jerks off," Kyle said. "Take yours out."

"No!" I was still holding the magazine and it was open to some girl who looked sort of like Jocelyn, except she was older. I liked that picture a lot.

"Chicken?" Kyle laughed and I frowned at him, catching sight of his cock as he played with it. That made me turn red, but Kyle thought it was because I was scared.

"Alright. Whatever," I sighed, pushing the magazine at him and I wasn't sure I wanted to show anybody my dick when it was hard, but Kyle was my best friend anyway. Everybody jerks off, I told myself and I soon had my pants and underwear off too.

"Turn the page, man..." Kyle was holding his dick and I was holding mine and we were both trying to hold the magazine and look at it. It was stupid and funny and after my initial nervousness, it didn't bother me jerking off next to my best friend so much.

"What the fuck?" Jocelyn's voice made me jump three feet off my butt. "What are you faggots doing now?"

"Nothing!" Kyle said and he was trying to cover up his dick with the magazine, having snatched it out of my numb fingers.

I just pretty much wanted to go someplace and die.

"Jerking off?" Jocelyn laughed and I was blushing. I felt hot all over, but I'm pretty sure I was white as a ghost too. "Let me see that!"

I was trying to cover myself up and reach for my clothes but Jocelyn stopped me cold with those black eyes flashing into mine.

"Just stay there, Chrissy," she told me, like she was my mom or something and I swallowed hard. "You too, pervert. Give me that."

Jocelyn took the magazine away from Kyle and his dick was still hard, but not mine! I was scared out of my mind, not to mention humiliated beyond anything I could ever imagine. The girl of my dreams had caught me beating off. This sucked so bad!

"You got a nice cock," Jocelyn sorta stopped for a second, smiling down at her brother's penis as it stood stiffly from his body. It was sorta big, I guess. Bigger than mine anyway, and Kyle had some pubic hair already, but he was growing a lot faster than I was.

"Uh..." Kyle was pretty red faced too.

"What have you got?" Jocelyn looked down at me. "Move your hands, Chrissy. I wanna see your dick."

"B-But..." I winced and moved my hands because Jocelyn could make me do anything.

"Heh! That's cute," she laughed at me and I almost started crying. "It looks like a clit sorta."

Jocelyn looked at the magazine for a minute, probably not even that long and I just looked at her, except I tried not to. I was pretty confused right then. Scared, humiliated, excited too and I didn't know why. She'd laughed at me, but now my dick was getting hard again and that seemed completely wrong. But my cock got hard for wrong reasons all the time. Sometimes it got hard for no reason at all.

Now it was getting hard while Jocelyn stood two feet away from me, towering above me in a pair of cutoffs and a skinny halter top so I could see her whole body practically. She was like a Goddess or something and I felt tiny as I sat there naked from the waist down, wondering if she'd get really pissed if I covered my growing erection back up with my hands.

"What are you looking at, Chrissy?" Jocelyn stared down at me and I closed my eyes. "Your little dick's getting hard again, huh?"

"N-Nothing, Jocelyn," I whispered, answering her original question. I shouldn't have said her name probably, everything I ever felt for her came out whenever I did and the quail in my voice was unmistakable.

"You were looking at me, huh?" she asked and I opened my eyes and I saw her smiling. "I know you like me, Chrissy."

"You do?" I asked, barely able to get the words out.

"You think I'm stupid?" she laughed at me. "You guys jerk off some more, I want to watch you."

"Jocelyn..." Kyle stared at her and I couldn't think of anything to say at all.

"You want me to show this to mom and dad when they get home?" she asked her brother. "Tell them what you little perverts were doing with it?"

"N-No..." Kyle shook his head.

"How about you, Chrissy?" Jocelyn looked at me and my erection withered. "Maybe I'll just tell Kara's little sister all about your little dick."

"Wha-What?" I felt my heart stop. Kara was Jocelyn's best friend and her little sister, Eve, was like the coolest, hottest girl in eighth grade. If she found out, Eve would tell all her friends and then everybody at school would know!

"So, come on," Jocelyn grabbed the chair from Kyle's desk and sat on it backwards, spreading her long, smooth legs around the back of it.

It was just a couple skinny pieces of aluminum so that chair didn't hide anything and I could all of a sudden see Jocelyn's tight pink panties as those shorts were real loose! I could see the hollows at the top of her thighs, so milky white and soft, and I about had a heart attack as I realized there were some little black pubic hairs curling out from under her panties. Jocelyn was like right in front of us and she knew what she was doing, I thought. She had to!

"Jerk off," she repeated. "You guys do it good and maybe I'll do it too."

"What? Really?" Kyle's mouth dropped open and then he grinned at her.

"Do ... What?" I asked like I was retarded.

"Chrissy!" Jocelyn laughed at me. "What happened to your dick? It was hard a minute ago."

"I don't know..." I frowned and glanced at Kyle. His cock was harder than ever and he was staring between her legs because even though Jocelyn was his sister, she was still the most beautiful girl in the city.

"Play with it," she demanded. "Make it hard again."

"Ummm..." I thought I was gonna puke. I was so nervous, embarrassed, scared, and a hundred other things too.

"That's pretty hopeless, Chrissy," she sighed after watching me rub my penis for half a minute. It wasn't ever gonna get hard now though, not when I wanted it to so badly.

"I'm sorry," I whispered and I couldn't believe I was apologizing to her, but I was. Kyle was just grinning at me, stroking his cock slowly while all of his sister's attention was on me.

"You gotta do something else then," Jocelyn decided.

"What?" I breathed.

"If you can't jerk off your little dick, then jerk off Kyle," Jocelyn said and she was totally serious.

"I don't want a guy touching my dick!" Kyle said, staring at his sister.

"What?" I stared at her too and that was fast becoming my favorite word.

"Hurry up, Chrissy," Jocelyn told me. "Grab my brother's cock. It's not gonna bite you."

"Jocelyn!" Kyle looked at me and then back at her.

"Do it! Or I'll fuck up your pathetic little lives so bad..." Jocelyn warned us both and I hesitated, but what else could I do?

"Hey ... Chris!" Kyle made like he was going to push me away, but Jocelyn stared at the boy and he gave in as my right hand tentatively wrapped itself around his penis.

"Yeah, like that..." Jocelyn nodded. "Now jerk him off, but do it slow! I wanna enjoy it."

I was almost in tears as I felt my best friend's cock under my fingers. It was different than mine. A lot bigger for one thing, like half a foot long probably. Mine was only like four inches at the most and Kyle's was thick too. It was hot and heavy, which felt weird, and it was soft, like his skin was velvet or something, but underneath it was super hard. I slid my hand up and down, trying not to think about what I was doing too much and just stealing looks at Jocelyn's exposed panties as much as I could.

"How's that feel, Kyle?" Jocelyn asked her brother, her voice kinda soft and she licked her lips.

"Um ... Good," Kyle told her and he wasn't looking at her, he was just watching my hand as I pumped his cock slowly.

"You like it?" she asked and Kyle nodded. "Yeah, you got a nice cock for bein' such a rodent. I bet Chrissy likes it too, don't you?"

"What? No ... Um..." I shook my head.

"Yeah you do," Jocelyn corrected me. "Look at that big cock, Chrissy. Yeah, jerk it off, that's so cool. Rub your thumb over the head a little, Kyle's gonna like that."

I shivered and my body grew warm all over as I did what Jocelyn told me to do. I rubbed my thumb over the smooth head of Kyle's penis, feeling his precum all warm and slippery. It was spilling down the shaft and my hand was already slick with the stuff. He got a lot wetter than I ever did.

"That feels awesome," Kyle breathed and he was smiling and nodding his head. "Squeeze it harder."

"Squeeze it, Chrissy," Jocelyn told me. "Up and down. That's a real cock. Kyle's gonna have a big dick when he grows up. He's gonna be a real man, fucking all his girlfriends ... Putting that big cock in their little pussies..."

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