Fiction

STRAWBERRY TARTS

Billy always had a thing for redheads, could never really explain why, it was just a natural attraction. After returning from an extended trip he moves in with friends and meets a cherry top that really got a rise out of him!

Sharing My Room With Sis 6: Loosing a Bet

“So what do you want to do tonight?” My sister Abby was lying on my bed as I came out of the bathroom. It was Friday, and we’d just gotten home from school and had the house to ourselves.
“I have a few ideas,” I said. I walked over next to her, standing next to the bed.
“I think I know what you have in mind.” She leaned her head towards me and softly kissed my dick through my pants. “Last night you didn’t really get a chance to savor it.”
Abby and I had been sharing my room since hers was flooded in a storm, and had spent over a week being more than a simple brother and sister. The night before, I’d come into my room to find her already deep asleep, and too horny for her to be satisfied with porn, I had started touching her. As I grew bolder, I had ended up rubbing my dick against her lips until they had wrapped around my head. After only a moment I’d pulled out and cum. Only after I was done did I find out she had been awake.
I sat on the bed next to her. Our heads leaned together and we began kissing. After our lips separated, she pulled away. “I just remembered, I have a science project I need to work on this weekend. I’d better start on it tonight.” She told me what it was. I’d had the same teacher the year before and had done the same project.
“I remember that one. Isn’t it a group project, though?”
“Yes, but the other members of my group didn’t volunteer to do much. It’s better if I do it myself.”
“Abby, don’t be such a pushover,” I told her. Abby had always been shy, and was afraid of confrontation. “It’s not cool that your group saddled you with all the work. Why’d you let them do that?”
“I don’t know, I didn’t want to be the bitch.”
“There’s a difference between being a bitch and standing up for yourself.”
“Sorry.”
“See, there, you’re doing it again,” I teased her. “Stop it! You can’t be so afraid of making other people uncomfortable.”
She rolled her eyes. “Fine, I’ll try next time.”
She worked on the project a while, then we headed out to grab some burgers for dinner. We got our food and sat down at a table. Abby opened hers, sighed a bit and pushed it to the side.
“They get your order wrong?” She nodded. “Take it back up there and get them to make you a new one.”
“That’s alright, I’m not that hungry.”
“This is exactly what I’m talking about. A little confrontation won’t hurt anything. They get this a dozen times a day; they don’t care. We paid for it, they should get it right.” She still hesitated. I rolled my eyes, then took the burger back myself. I came a couple of minutes later with a new one. “See.”
“Fine.” She was obviously annoyed at my pushing her. I decided to drop it for now.
We went home and Abby declared she was taking her dog for a walk. Feeling anxious that she was mad at me, I grabbed my dog and went with her. We walked down to the park together as we’d done for years. When we got there we let the dogs off their leashes and Abby threw a ball for her dog Angie, a blue healer. My dog Willow, a German Shepherd, ran and beat her to it.
“Your dog’s being a jerk,” she said to me. She was clearly still annoyed.
“My dog’s fine. I think Angie’s just being a push-over.” I’d reverted to my older, more antagonistic big brother self. My comment clearly didn’t go over well.
“No she’s not! I bet she beats Willow this time.”
“You’re on.” Buster brought the ball back to me, and I tossed it back to Abby. As she picked it up, I stepped closer to Angie. When Abby threw the ball, I grabbed Angie’s tail a moment, giving Willow a head start. “See. Angie is a push-over.”
“Cheater. You’re afraid of a fair race.”
Willow had always been the faster dog. There wasn’t really any question who would win, but now Abby had committed to backing up Angie’s honor. I decided to exploit this. “Tough talk. What are we betting?”
“Loser has to be the winner’s slave for a day.”
“Alright.” It was a bet we’d done once a couple of years ago. I had won, and had made Abby follow me around taking small orders and then clean up my room before I lost interest and did something else. This time, however, the old kid game had an entirely new subtext.
Ideas were already coursing through my head for what I’d do with her. Mom had 12-hour shifts tomorrow and Sunday both, giving us free reign of the house. I could have her bathe me and get dressed, or have her pose naked for some pictures. I didn’t want to push her too far out of her comfort zone, but a little might help make her a little more assertive. Mostly, though, I wanted to get my dick in her mouth again. I wondered how many blowjobs we could get into one day.
I got the ball from Willow and handed it back to her. She paused a moment. “Are you sure you want to go through with this?” she asked.
I wasn’t about to let her back out now. “I do if you do,” I said, somewhere between confident and condescending.
“Alright,” she said. She turned to her left and hurled the ball a different direction than before, and the dogs went rushing after it. Even as I wondered why she’d thrown it that way, I saw the other dog down there.
Willow may have been faster, but Angie was the better trained. As soon as Willow saw the other dog, she rushed towards it. Abby had spent more time teaching Angie to follow commands and avoid distractions. Willow had just started sniffing the other dog when Angie grabbed the ball.
Abby had flat-out outsmarted me. Somewhat flabbergasted, I went down and collected Willow. On the way home, Abby smiled, whistled, and was almost skipping, all trace of her earlier grumpiness gone.
At home we headed to my room to get ready for bed. Abby hit the bathroom first and came out already dressed in her pajamas; a white tank top and very short shorts. She walked up to me and slowly wrapped her arms around me. Her mouth approached me as if to kiss, then she stopped abruptly. “You’d better get a good night sleep tonight, brother. Tomorrow’s going to be a long day.” She released and slid past me to the bed. She climbed to the far side and pulled the covers tightly over herself, facing away from me. For the first time in over a week, I had to go to sleep without release.
I woke up before Abby on Saturday, just early enough to see Mom head to work. I had breakfast and sat on the couch, wondering what Abby might have planned for me.
Around 10 Abby came in and sat down on the couch next to me. “So, what are you going to have me do today,” I asked.
She seemed a little uncomfortable. “This is kind of silly. If you don’t want to do it, its ok, I understand. I don’t want you to do anything you’re uncomfortable with.”
I should of known she’d try to chicken out. I couldn’t stand seeing her wimp out again. “You’re being a push-over again, Abby. You won, fair and square. I have to be your slave today.”
“Alright, just making sure. Since you’re so adamant that I shouldn’t do that project myself, I’ve decided you should do it. Let’s go to your room.”
We headed to my room and she went into the closet and started rooting through my stuff. I wondered what she was looking for, but was too distracted by her ass to ask. The shorts she wore for pajamas barely covered, and when she bent over slightly, they sunk into her crack and the curve of the bottom of her ass cheeks stuck out the bottom.
After a minute, she found what she was looking for. She turned around holding a bowtie I had worn to our cousin’s wedding a year ago. “This is what you’re going to wear today.” She tossed it over to me, and I put it tied it around my neck. I turned to the computer to start on the project.
“Hold on there, brother. I said you would wear the bowtie, I didn’t say anything about a shirt or pants.” I turned back toward her. She stood waiting. I took off my shirt and pants, leaving just my boxer-briefs. She stepped over to me. “These, too,” she stuck her fingers in my waistband and pulled the front down over my partial erection. She then slid my underwear down my legs, crouching down as she did, until my dick was right in front of her face. I stepped out of my underwear and she tossed them aside. She reached up and lightly grabbed my cock with her fingertips, then moved her head to one side of it, then the other, examining it. She held it straight up and with her other hand, lifted up my balls in her fingers, as if weighing them. She brought my dick down until it was pointed right at her lips, just inches away.
“Today’s going to be fun. But right now you have work to do.” She released me and stood up. “The instructions for the project are in my folder by the computer. I’ll be watching some TV.”
About an hour later she called me into the living room. I walked up to the couch, very conscious of my nudity. Being naked so close to her, I couldn’t help from getting hard. “I want some lunch,” she said. I went into the kitchen and made her something. I took it in to her on a tray and put it right in front of her, standing in front of the TV. My dick pointed right at her, hovering above her food. “Looks good,” she said. She patted the side of the couch. “Wait here until I’m done so you can clean up.”
I stood beside the couch as she took her time eating, my dick at attention a little ways from her. When she finished, I took the tray back to the kitchen and returned to the living room.
“I need something to do until my next show starts,” she said. “Come stand over here again.” I walked over to the couch and again stood next to the armrest, facing her. Abby reached her arm around me and ran her fingers down my back and across my butt, then grabbed with her palm. With her other hand, she tickled my balls a moment, then ran her finger up my shaft and in a circle around my head. She pinched my dick firmly with her fingers and began stroking me, watching intently, until I started oozing pre-cum. With the hand on my butt, she pulled me toward her slowly until my dick came to her wet lips. Still stroking, she slurped the clear liquid off the tip of my dick with three long kisses, then ran her tongue from the bottom of my head across the tip to the top. She pulled back very slightly, hovering her lips next to my dick, then glanced at the TV.
“Oop, my show’s starting.” She released my butt and dick and sank into the couch. “That’s all for now. Go work on my project.”
So horny I couldn’t talk, I turned and walked away. It was clear she was going to be an insufferable tease today. I decided I’d have to take some of the edge off. I went into my room and shut the door. Moving all the project stuff aside, I sat at my computer and started browsing through porn sites and stroking myself.
After only a couple of minutes, I heard the creak of the door behind me. “I thought I’d better check on you. I don’t remember giving you permission to do that,” Abby said. I didn’t even have enough time to close the browser. It wasn’t the first time she’d come in while I was looking at porn. I desperately hoped she’d repeat her previous reaction. I kept stroking myself in front of her, hoping she’d come over and help me. “Are you still my slave?” she asked.
“Yeah.”
“Then I don’t think you should be doing that on my time.” I reluctantly released my dick. She climbed onto the bed next to me and sat facing me with her back to the wall. She spread her legs apart with her knees bent. She looked at the computer. “That does sound like fun right now. Why don’t you show me some things?”
I complied, my frustration mounting. I went through some pictures and videos like what we’d looked at before. Several minutes of handjobs and pussyeating went by and I noticed that Abby’s hand had slid between her legs. With no panties on and her legs spread apart, her shorts pressed against her pussy. Little hairs stuck out from under the fabric on both sides. Her fingers ran smoothly along her camel toe. “Need any help?” I asked hopefully. It was obvious how horny I was. My dick throbbed slightly.
She waited a moment. “No thanks.” She nodded back at the computer. “Continue.” I could barely stand it. I clicked to a handjob video. “I think his dick is bigger than yours,” she said. She pressed her legs together and lifted her butt up slightly to pull her shorts down over them, then lifted her legs up. She pulled her shorts up to her knees slowly, revealing her bare pussy. The lips were round and soft, but I was close enough to see that the skin was covered in tiny goosebumps where her short fuzzy hairs came out. She pulled her shorts off entirely and spread her legs again, running her fingers across her pussy.
I decided if she was going to taunt me, I’d have to call her bluff. I closed the video and started surfing other things, intent on finding something shocking enough to embarrass her out of what she was doing. Despite our time together, she was still just 15 and hadn’t been exposed to much sex, especially anything real kinky. “Let me show you some other porn I like. Just let me know when you’re ready to stop,” I said. The next few videos showed deepthroat blowjobs and one where the girl was sucking a guy’s balls. I looked over at Abby and she looked back at me, not showing any discomfort. With her left hand, she spread apart her lips. Her right forefinger ran along the pink flesh inside, then plunged inside. She closed her eyes and moaned for my benefit, then looked back at me and nodded toward the computer.
I continued. A girl with a small vibrator on her clit cums, squirting as she orgasms. A girl is tied to the bed and fucked in the mouth, swallowing all the cum. Two lesbians suck each other’s tits and then share a dildo.
Abby wasn’t backing down. Seeing that I was looking at her again, she pulled out and slid her fingers up to her clit. She closed her eyes again and pressed down. Her pussy lips wrapped around her fingertips, as if deeply kissing them. She started to rub in small circles. Her left hand ran up her stomach, pushing her top over her tits, and grabbed the left one, pinching the nipple slightly in her fingers. “Mmmm,” she moaned.
I’d have to push her a bit further to break this. “This is one of my favorites,” I said, and pulled up another video. It was a threesome, starting with a blonde and a brunette sucking a dick. They continued by taking turns eating each other out. The brunette bent over, letting the blonde lick her from behind. After a minute on her pussy, the blonde’s tongue ran up to the brunette’s asshole. I looked at Abby, expected this would be too much for her, and slightly regretted pushing it this far. However, Abby was continuing to watch and rub herself. It seemed she knew what I was doing and wasn’t about to back down.
In the video, the guy fucked the brunette from behind, while the blonde situated herself right below them and licked between her pussy and his dick. He pulled out and came on her, dripping cum down the brunette’s ass and pussy into the blonde’s mouth.
I looked back at Abby. She continued to rub herself, now with her eyes closed, I don’t know if she’d been watching much of the last video. She was rubbing herself vigorously, and her body was tense. Her pussy lips were now wide apart and glistened with moisture. Her fingers were moving so firmly now that her whole pussy molded to every circle. Her thighs were tense and spread so wide they almost pressed into the sheets.
She started to cum. Her free hand grab at the sheets, and her feet pressed into the bed. Her butt lifted up, her ass cheeks squeezed tightly, and her whole pelvis moved up and down in irregular, spasmed thrusts. Her pussy lips were wide and wet, and I could see her vagina squeezing rhythmically. A few drips of white liquid ran out and slid down her ass crack. She started to relax and lowered back onto the bed.
Her breathing started to settle. She opened her eyes and looked at me, blushing. I smiled at her. Her eyes fell down my naked body to my dick. “I thought I’d told you not to touch that.”
Watching her masturbate had made me start stroking my dick again without even thinking. I let go. It was rock hard, and throbbed on my every heartbeat. “It’s been hard so long it’s starting to hurt,” I told her.
Abby sat up. “I’m sorry. We can stop this slave thing if you want. I don’t want to make you uncomfortable.”
I couldn’t back out now. It would mean going back on our deal, and it would mean eating my words to her earlier about being a pushover. I knew she’d backed me into a corner, but I wasn’t going to give in. Plus, I really wanted to know where she’d take us. I just shook my head. “You want me to finish your project now, ma’am?”
“Yes.”
She put her shorts back on and lay on the bed reading a book. It took me another two hours to finish the project. I finally finished and told Abby. It was starting to get late, in another hour or so Mom would be home from work. I turned my chair to face Abby on the bed. “The day’s almost over, Abby. Anything else you want me to do as your slave?”
“You’ve been such a good slave. I have one more thing for you. All this schoolwork has made me tense. I could use a massage.” She peeled off her shirt and lay facedown on the bed. “Start on my shoulders.”
I sat on the bed next to her, my bare skin touching her side. I gently brushed aside her long red hair from her shoulders and massaged.
“Now get my back.”
With my thumbs, I pressed into her lower back, letting the fingers on both hands slide along her sides, caressing. I worked my way higher and higher on her back. My fingers brushed along the sides of her breasts, and with each knead of my thumbs; I let my fingers pull on her a little. My thumbs worked out from the middle, letting my fingers get closer and closer to her nipples.
“Get my legs.” Still being a tease.
I shifted down to sit by her legs. I worked on her calves, then moved up to her thighs. I worked up them slowly, pausing on the inside about halfway up.
“A little higher up.” She was getting more relaxed now. The sly teasing in her voice seemed to be gone. Massaging more lightly with just one hand, I moved up a bit higher and worked.
“Little higher,” she said again. As my hand moved up, her legs spread apart slightly. My fingers just a couple of inches from the fabric over her pussy, I kneaded a bit, then slid my hand up to massage the back of her thigh, my thumb running against the edge of her butt under her shorts. I moved my hand to the near thigh and worked inside again, teasing my finger an inch from her pussy. Her legs spread even more.
“A little bit higher.” She was almost whispering.
Lifting everything but the finger, I ran it up to the top of her thigh, just underneath the fabric. I ran it along the seam of her thigh and groin, feeling her short fuzz. I pulled back and moved it to the other thigh, repeating the caress but letting it just a little bit farther onto her pussy.
I took my finger and slowly and lightly pressed it on the fabric right in the middle of her pussy, then ran it gently up and down. Pressing just a bit harder, I made a slow spiral motion down its length.
My finger moved back up her thigh to the side of her pussy, and with my other hand I pulled the soft fabric to the side, giving me access. My finger explored in her crack.
I was sitting on the bed with the side of my butt pressed against her knee, turned facing her top, my arms stretched to where they needed to be. As my finger started to work deeper into her hole, she reached her hand back, slid up my thigh, and gripped my dick. I pulled my finger out and brought to my mouth, tasting her juice. Moistening my thumb, I slid my finger back into her pussy and, sliding my thumb under her, gently rubbed at her clit.
Suddenly she released my dick and raised her butt in the air, pulling away from my hand. She slid her shorts down to her knees, and with her ass still in the air pressed her chest into the bed. I slid her shorts the rest of the way off. As I moved to put my finger back into her, she spoke.
“Kiss my butt cheeks, slave.” I was surprised at her request. I couldn’t believe my shy sister would ask for that. I wasn’t about to refuse, though. I climbed onto the bed between her legs. I lowered down to the white, smooth skin of her cheeks, and gently kissed one. Though I’d seen it in porn, I’d never thought about doing it myself before. Another time, I might have just thought it was weird. But right then I was hornier than hell, and having my shy sister command me to do it was easily enough to put me over. I kept kissing along one cheek, then the other, each kiss becoming deeper until I just ran my tongue across her butt.
“The middle, too.” I started kissing deeply down her crack to the middle, then ran my tongue back up.
“Kiss my butthole,” she said. This command wasn’t as forceful, but almost pleading. Too horny to bother thinking about it, I started kissing softly on the inside of her cheek next to her hole. I pressing my face between her cheeks and pressed wet lips against her butthole. She exhaled sharply. I ran my tongue in a circle around her hole, then spiraled in and made small circles on it. She arched her back, thrusting her groin more towards me.
Running my hand along her thigh, I started lapping up her crack across her butthole, first lightly, then more heavily. With each lap I went lower, reaching the fuzz between her pussy and ass. Pausing just a moment, I moved down and ran my tongue deep between her pussy lips and up until I reached her asshole, doing another circle. I repeated a few times, then brought my hand back up and pushed my finger deep into her pussy.
She pulled off my and turned toward me on the bed on all fours. “Lay down.” I brought my chest straight down onto the bed under her head. “Turn over.”
I flipped onto my back with Abby’s tits dangling below her right over my face. Before I could even rise to suck her nipple, she crawled over me, bringing her knees to my elbows. Pushing up on her arms, she lowered her pussy right onto my face. I buried my lips and tongue into her pussy, sticking my tongue as far down her pussy as I could, my nose pressed against her butthole.
She lowered her chest down, raising her pussy off my face just slightly, and I stretched up to keep licking her. Her weight on her elbows, I felt her hand wrap around my dick. She pulled it to her face and wrapped her mouth around my head, sucking and slurping as she stroked.
I reached my arm around her leg and got my finger wet in her juices and started tickling around her butthole. I moved my mouth to her clit and started licking and slid my finger back into her pussy. Feeling her lips wrapped around my dick, I wrapped mine around her clit and sucked gently, quickly rubbing my fingertip up and down along the front wall of her vagina.
Abby started to cum. She sat up almost straight on my face. She clenched her thighs to keep from smothering me, but squeezing my face slightly. Her hand kept stroking my dick, and her other hand pressed into my stomach. She started pulsing, hard than before when she was masturbating. Her thighs pressed tighter a moment, and then her pussy pushed hard against my face, pinning it down to the bed as I kept sucking. Her vagina squeezed my finger in spasms, and again a bit of white liquid dripped down around my lips, finding a way into my mouth as I sucked.
It was the hardest I had ever cum. I felt the first squirts shoot out like a rocket. A whole days worth of arousal came firing out in spurt after spurt.
It took several minutes for us both to come down from our orgasmic highs. She finally unstraddled me and fell into the computer chair. I just lay where I was and looked over at Abby. Globs and lines of my cum ran up and down her belly, on her tits, on her face and in her hair. She smiled at me, and I watched a glob roll off the side of her nose, over her top and bottom lip and stop on her chin before she wiped it off with her finger.
Smiling, she started to say something, then paused and averted her eyes as if she thought better. She giggled a bit and looked back at me. “See, if you think I’m a pushover, you can kiss my butt.” I couldn’t help but smile at her bad joke.

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You First 4

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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The Island, Chapter 19

Author’s Note: This is a serial novel. It mixes actual experiences, fantasies, and outright lunacy. It is not a quick lurk-and-jerk. I believe in a slow build, in order to have a better payoff at the end. (Like Sting, I’m Tantric…). I plan to release a new chapter every week. Hopefully the response will be good! Enjoy.

Going Nova: A Wide-Eyed Adventure

I hope you enjoy where this story leads. There are many more planned chapters to come. Just a heads up to get it out of the way early on: to comply with the rules of this site, all participants in this story are no younger than 18 years of age.