Introduction:
I really, really appreciate you all being so patient while I finally got this latest chapter together. I hope it lives up to your expectations. Life and work have been uncommonly busy these last few months, and now that I (finally!) have a few days to myself I wanted to get this written and done (finally). Thank you all so much, for everything. Please, keep those comments and votes coming. I wouldn’t do this if I didn’t know so many of you enjoyed these. Now let’s get to it: finally, here it is, Part Four of You First!
As you might imagine, I had a hard time sleeping that night.
Granted – all the fun I’d had with Jen that day had worn me out, physically (and I was not complaining), but those words kept playing back in my head, on infinite loop. My Christmas present to you… will be myself.
I couldn’t get my brain to shut up. The mere idea was enough to make certain parts of me stand at attention, and to make things worse, remembered images and sensations from the day kept popping back up. I watched the clock wind down into the wee, single-digit hours of the night. I jacked off, twice, in the space of an hour, in an attempt to exhaust my body so that I would fall the hell asleep.
Both times I got up, grabbed a fresh pair of boxers, and went to the bathroom to clean myself up. The first time I just fell back into bed. The second time I lingered at the top of the stairs, staring at Jen’s closed bedroom door. Thinking about what I’d done in there earlier made my dick twitch, and I winced, because I was starting to get chaffed.
I almost did it. It was like two or three in the morning. The parents were dead asleep by now and there was plenty of moonlight to see by. I almost marched right in there. I wondered if she slept naked; either way it wouldn’t have mattered. She’d be mumbly, still mostly asleep, until I grabbed those tits of hers. I could already feel her nipples harden against my palms. She’s hiss in a breath, and moan, and lift her arms above her head to give my hands free reign to wander wherever they liked. I’d kiss her belly button. She’d kiss my neck. Her naked legs would wrap around me, and I’d lay her down and…
My shaking hand was hovering within an inch of her doorknob. Jesus, I thought to myself, get a grip! I took a long moment to collect myself, forcing myself to take deep breaths of the cold night air. It would be warm under her covers. But it would be warm under my own, too.
I wanted it. Bad. But I wouldn’t force it. She told me she’d do it when she was ready, and I respected that.
Reluctantly, I trudged back to bed.
And I had been out of them so long that the blankets had gotten cold.
I didn’t tell Jen about what had happened. I guess I felt embarrassed. About what, I wasn’t sure. Losing control, maybe? I guess I felt like I might have scared her. (You wanna know the kicker, though? I did eventually tell her, a long time after the fact. And she told me that if I had actually done it, if I had come into her bed that night and asked for sex, she would have let me. Never felt so stupid in my life. But I had no way of knowing that at the time. Anyway.) We didn’t have a whole lot of time to talk (or fool around) around then, so I guess it just never came up. School started pretty quickly after Christmas that year, so a lot of our time was spent getting back together with friends we hadn’t seen in two weeks and making sure all our classes and books and whatever were in order. We did spend a lot of time getting use out of our Christmas presents, though. Jen started taking a zillion photos of everything and taking her camera everywhere. Many of her shots were just her trying it out – different filters and settings and whatever, I don’t speak camera – and you could tell she was just having fun with it. Others… well, to my untrained eye, they were really pretty good. She definitely had an eye for composition, and Colorado provided her with no end of scenery and landscape for her to photograph. If she had some sort of numbered requirement to meet before her class started, she probably got through it in a day.
When we were certain we wouldn’t be seen, I’d give Jen a pinch on her butt, or she’d give the front of my pants a stroke. We developed excellent poker faces.
And then – it happened. Finally.
It was Saturday night, the last one we’d have before school started back up. We’d just finished dinner. It was Dad’s turn to clean up the dishes, and Mom was curled under a blanket on the couch, already half-asleep and pretending to watch the news. I’d retreated to my room and was getting some use out of my Christmas present – getting close to a big boss battle in the game I was playing – when Jen leaned around the side of my open door and say, “Hey, I’m bored. Wanna go see a movie?”
I looked up at her. “You want to go out.” She nodded. “Now.” Another nod. “In this cold.”
Nod, followed by a hopeful grin. “Pleeeeease?”
I snorted out a laugh. “How can I say no to that face?” I switched my game back off and started digging for clothes.
Like I’d mentioned, we lived in Colorado, and it was just after Christmas, so, the dead of winter. Ice and snow everywhere. Pretty to see, sure. Not so fun to drive in, though. Dad only let go of his car keys after I promised four times that I would be careful, and to call right away if anything happened. Jen bought the tickets online as I was having that joyous conversation, and then off we went.
“We going to the big one or the small one?” I asked. We had two movie theaters nearby. One was over by the mall, and it was big, shiny, and new. The other was much smaller and not quite as grand, but the tickets were cheaper.
“Small one,” she said, buckling her seatbelt and wrestling with the heater controls in her gloves.
The drive actually wasn’t all that bad. The roads were pretty clear, there weren’t many other cars on the road, and any ice patches we might have hit had enough slush on them to give us good traction. Dad’s car, which we affectionately dubbed The Monster Truck, was built to handle this kind of thing.
It wasn’t until we were almost there before I thought to ask what we were seeing. She bit her lip and pulled away from me a little bit before she told me.
“What!” I exploded. She’d bought tickets to an obnoxious big-celebrity holiday cash-grab, something I had zero interest in seeing. “Please, Jen, tell me you didn’t.”
“Don’t be mad.”
“I’m not mad, I’m just… gaah, why that, of all things?”
She managed to look haughty. “I have my reasons,” she stated primly.
I rolled my eyes. “Yeah, I’m sure you do,” I muttered.
“Hey, you might like it.”
“I might also decide to ram us into a tree.”
And so on went the conversation. We continued bickering all the way up to the ticket booth, where the worker tried not to laugh at us. “Can you believe she’s making me see this?” I asked him as Jen handed over the confirmation number.
He grimaced as he pulled the display up on his monitor. “Yeesh. What we have to put up with for a date, huh?”
Instinctively I was about to correct him, but Jen suddenly latched onto my arm and gave me a peck on the cheek. “Hey, he’s getting something out of it, too. The pleasure of my company.” She said the last bit in a faux British accent, making me and the ticket guy laugh.
“Well, enjoy,” he said, sliding the tickets through the hole in the glass. We thanked him and went inside, shedding our hats, gloves, and jackets. We’d just eaten, so we skipped the snack counter. Once past the ticket-tearer, the hallway was empty, and I leaned over to her.
“That guy at the booth thinks we’re dating.”
“So?” she asked, her eyes merry. “Maybe I want to pretend I’ve got this stud for a hot date tonight.”
I tried to make some sort of comment to that, but honestly I was kind of at a loss for words. I wasn’t accustomed to girls talking to me like that. It was nice. I glanced up and down the hall, just to make sure no one we knew was there, and I grabbed her hand. Her fingers instantly laced together with mine. She didn’t say anything, or even look at me, but she was smiling.
There wasn’t a single person in the theater when we got in there, which was fine by me. “Cool! Free choice of seats.” I aimed for the exact middle. “Here?”
Jen shook her head. “Too close.” I let her lead me to about 3/4ths of the way back. It was a bit far for my tastes, but since I didn’t want to see the movie anyway I didn’t complain. We waited. We watched the before-show promos. The lights began to dim and the previews started, and no one else had entered the theater – I wasn’t surprised.
The previews came and went. The movie started. Ten minutes into it I was bored and starting to check my watch. “Why did you make me see this?” I muttered.
I hadn’t expected her to answer, much less give the answer she did. She leaned in close and whispered, “Because I knew no one else would come to see this piece of shit, stupid.”
I turned to her, stunned, and I saw that mischievous glint in her eyes and it finally – finally! – sunk in. A quick glance around the theater confirmed my original assessment. We were in that movie theater entirely by ourselves.
She wrapped her arms around one of mine and snuggled into me. “I feel bad that we haven’t had much time to ourselves these past few days,” she said. “And with school starting back up soon we’re going to have even less. Soooo…” She leaned in even closer and lowered her voice until it she was whispering. “I thought maybe we could sneak off and make out at the movies.”
I kissed her grinning face, and she was clearly happy to give as good as she got. Right then I loved her more than I had in my entire life. Our tongues played and danced and I was all too happy to totally forget about the movie.
It wasn’t long before Jen started getting pretty into it. She was clutching at the back of my head, pulling me into her, moaning as I kissed her. I was starting to get pretty warm under my second jacket (always dress in layers, kids!) so I took it off, and one of Jen’s hands roamed over my chest. I wanted to do a little roaming of my own, but, while we were alone in here, we were still in a public place, and I wasn’t quite sure how far she’d want to take this.
I got my answer soon enough, when one of her hands grabbed me between the legs. I hadn’t been quite fully hard, but that sure got me there in a hurry. “Jen…” I started, wondering how best to approach this. Could I be about to receive the fabled movie theater blowjob?
“Let’s leave,” she said. “We’re not watching this anyway and I won’t want someone walking in on us.”
Oh. Well, that was fine, too.
I tripped over myself trying to grab all of our stuff and negotiate my way through the narrow row of seats as fast as I could. I was not going to pass up this opportunity. We took the side exit, as casually as we could, as if we’d just gotten out of some other, far less crappy movie, and not have to walk in front of the same employees we’d passed fifteen minutes ago.
We shut the truck doors and started the engine. “Where to?” I asked.
“I don’t care,” she said. “Anywhere.”
Damn. She was hot and ready to go. Well let’s not delay things, shall we? I asked myself, and hit the gas hard enough to scrape the tires a bit on the pavement before they gained traction.
It was pretty easy to tell where our town began and ended. One side of the street would be all lights, convenience stores, gas stations, restaurants, and so on; and on the other side of the street would be nothing. Trees and hills and rocks. We hit that invisible wall pretty quickly and it felt like the truck was swallowed in darkness. I drove as fast as I dared without going (too far) over the speed limit or running any lights or stop signs. The absolute last thing I needed was to get pulled over. I was fairly certain a cop would kill the mood pretty quick. Not to mention having to explain the ticket to the folks. Well, you guys know what it’s like when your sister wants to leave a movie to drive off somewhere and make out…
“Actually,” Jen interrupted my train of thought, “I know exactly where to go. There should be a turn off to the right coming up, take that.” I shrugged and followed her directions. The road became significantly less paved and I wondered what she was up to, but didn’t ask questions. (Would you?)
Trees. Bumps. High-beams. A close call with a deer. You don’t need to know all that. Point is, we came around to this ridge. “Wow,” I said, parking the car. I had no idea how she’d found out about this place. From here, we could see the entire city. Lines of streetlights, signs, cars. It seemed like it just went on and on.
“It’s gorgeous,” I said.
“I seem to recall,” Jen said, leaning towards me, “that when we started this whole… thing that we do… that you had mentioned something about being in a car, overlooking the city…”
“I did?” I honestly did not remember that.
“You did.”
“And what happened in this thing that I was describing?”
“You were talking about me getting naked with a boyfriend.”
“There are parts of that sentence that I like.”
“I want you, Shawn.”
“What, now?”
“Now.” We kissed.
“Aren’t you worried someone’s going to find us?”
She started taking off her shirt. “Stop me, then.”
Off came the bra. I snorted. “You first.”
She growled as she flung herself over to my side of the truck, straddling me. Instinctively my hands went to her hips, but she grabbed them and planted them firmly on her naked breasts. She groaned as she kissed me. I pinched and pulled at her nipples, rather mercilessly, until she squealed. Again, her hands found their way to my pants.
“Are you sure?” I asked as she fumbled with my zipper. She’d said she’d wanted a few weeks. It hadn’t been that long.
She stopped. Her eyes rose until they met mine; she made sure I was looking at her. She placed one hand on either side of my head, and leaned forward until her face was within an inch of mine. I could feel her heavy breaths on my lips. “I want you in me, Shawn. I’ve waited long enough.” And then she blinked, drew away. “Unless… don’t you want to…?”
“Wha- Yes! Good God, yes! Do you have any idea-”
She cut me off with another kiss; I’d been about to tell her about the other night, where I’d almost come into her room in the middle of the night, but apparently…
Allow me to share with you some advice. Having sex with someone for the first time is a nerve-wracking experience in and of itself. You’re both excited, and terrified, and you’re so worried about what the other person is thinking that you almost forget to enjoy what you’re doing. Doing all of that in a car is probably one of the dumber things I’ve ever done in my life.
I mean, there’s just no room, to begin with. Even when I pushed the seat back we were horribly confined. And, we were doing all this in the wintertime, so we were each wearing about a bajillion layers of clothing, and that’s just a whole lot of stuff you don’t want to deal with when you’re trying to get at someone else’s skin.
But when we finally managed to shimmy my pants halfway down my thighs, and we did the same for her… and she turned around and got into (what I later learned was called) the reverse-cowgirl position, because it was the only way we would fit… and she was touching my hard dick with her hand on one side and with her hot, wet pussy with the other, and it stopped being outside and was suddenly inside…
We both sort of sucked in a surprised breath at the same time, and held it for a second.
“You okay?” I asked.
“Yeah. Yeah, I’m fine. It’s just… different that I was expecting.”
“Different good or different bad?”
“Oh, differently definite good. Definitely different good. You know what I mean.”
“Yeah. I do.”
“You like it?”
“Yeah.”
“Really?” She sounded relieved.
“Oh yeah.”
“Good.”
After a few moments, she started moving, slowly, drawing a clipped groan from me. I realized I was gripping the seat as hard as I could; I’d never felt anything like this in my whole life. I mean, Jen’s mouth was incredible, but this…
“Oh, God, Shawn,” Jen moaned as she started moving faster. I grabbed her just above her wonderful ass and began moving in time with her. Or at least, I tried to. As soon as I started she cried out and sort of collapsed, ceasing to move altogether. It was like she had forgotten how. I took this as a good sign.
Jen leaned up against me, reaching her arms back to encircle my head, run her fingers through my hair. I kissed the back of her neck and she shivered. She whispered my name a time or two. For a while, I lost myself in the feeling of my cock inside of my sister, in the smell of her pussy and the sweat on her skin. My hands stroked her legs, the sides of her body, her breasts.
Then I had an idea. With one hand still on her chest, caressing her nipples and steadying her with that arm, my other hand moved… south. She let out a noise that was half excitement and half terror as my finger touched her clit.
“No! Not there, Shawn, it’s too much, I… I can’t…”
I didn’t stop.
Her whole body tensed up at my fingers playing with her pussy while I fucked her, shook, like she was shivering violently. And then she jerked, once, hard, threw her body forward, far enough to where I couldn’t reach. She immediately slammed herself back and grabbed my hand. She tried to put it back between her legs but it was like she couldn’t work her own hand properly.
“Well don’t stop now!”
“You told me to!”
“Well, you… shut up! You almost made me come!”
“You mean that wasn’t it?”
“No!”
Oh. Well, in that case…
She screamed as I started fucking her with renewed vigor, anxious for her to have an actual climax. I rubbed my fingertips back and forth over her clit as fast as I could
I’d like to tell you that I made her come first, that I was this great sex-stud that somehow managed to get her to orgasm five times and leave her breathlessly panting for more or whatever. But that’s not what happened. It was my first time too, and all of this was waaaay more than my inexperienced teenage self could handle. I came before she was ready, before I was ready, before I could ask if it was okay for me to come inside her, birth control or no. My hips jabbed into her spasmodically a few times, while I was still trying to play with her clit.
“Did you come?”
My eyes slid sideways. “Yeah.”
And then she said the most amazing thing, which made it all better. “Good.”
I collapsed back into the seat, exhausted and grinning. I saw her move her own hand between her legs, felt her start to play with herself, with me still inside her. I watched as she hunched over, and her muscles grew tighter and tighter. It wasn’t thirty seconds before she shook once, hard but briefly, and huffed out a breath like she’d been swimming underwater for too long. Gasping for air, she slowly slid into the passenger seat.
We both panted there for what seemed like forever, until we could control our breathing.
“I’m sorry I didn’t make you come,” I said.
She smiled weakly. “You came awfully close. Just means we’ll have to try again sometime.” She leaned back over, and gave me a chaste kiss on the cheek. “Thank you.”
“For what?”
“For making my first time incredible.”
I smiled. “Anytime.”
Her eyes sparkled. “I’m gonna hold you to that.”
“I hope you do.”
She kissed me again, this time on the mouth. “We’d better get back.”
I nodded, and we began collecting our clothes. It was oddly embarrassing, considering what we had just done.
We went home. We artfully answered our parents’ questions about the movie using nothing but the truth (“It was awful.”), and went upstairs to bed.
And that, ladies and gentlemen, is how I lost my virginity to my sister.
And that’s when things started to get weird.

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