This is my first story, so I apologize for grammar, spelling, and any other mistakes. Please leave feedback in the comments to help me give you (the readers) a better experience reading future stories.
“Tick, tock, tick, tock…” the clock went. I was staring at the clock waiting for the bell to ring. Final exams have just finished, but my school had a couple of extra days to get grades processed. I knew that once the bell rang, I would be home free, done with sophomore year of high school, and summer vacation would begin. As my teacher said something (I swear that I don’t even know what she was saying. I’d have to assume that it was something along the lines of have a good summer or something like that), the bell rang, and everyone rushed out of the classroom. I went to my locker to clean it out, and then I accidentally bumped into Alyssa. She is one of the hottest, if not the hottest, girl in the school, and by far the hottest girl in my grade. She ended up dropping a couple of papers and two notebooks as a result of us bumping into each other.
“Sorry about that.” She said.
“No. It’s my bad.” She then proceeds to pick her stuff up and I help her. When I hand over her stuff,
“Oh, Kevin. Hi!”
She goes in for a hug, which I also do just to be polite. While we talk, we start to walk. And because of her hugging me, I end up getting a massive hard-on, which I try to cover up with a notebook.
“Hey Alyssa. What’s up?”
“Nothing. Thank god school’s over.”
“You can say that again.”
“You got any plans for the summer?”
“Not much. Just relaxing, doing stupid school work a week before, the usual. And my dad’s getting married again.”
“Yeah. What about you?”
“Relaxing, work. The usual. And my mom’s getting married.”
“On the 14th. Any reason?”
“Damn. I was gonna ask if I could come along, but my father’s getting married on the same day.”
“That sucks. I probably would have asked you anyway.”
I should get to describing the two of us. I’m 16 years old, black hair, brown eyes, and stand around 5’10 with a somewhat average build. I’m not a complete bodybuilder, but I’m not morbidly obese either. I do what I need to do in order to get by. Right now, I was just wearing tan-colored cargo shorts, and a red t-shirt. On the other hand, she’s 15 years old (turning 16 in a few weeks), has dirty blonde hair, hazel eyes, stands around 5’5 with a slender build, real nice face and smile, 34D boobs (I think. It was either 34D or 34DD), and one hell of an ass. She’s also on the tennis team. At the time, she was wearing a gray tank top and shorts that showed how round her ass was. No, both of us weren’t going commando. Truth be told, I met her first day of high school, but I never really talked to her since then. I’ve only seen her around the school. Since the middle of freshman year, when I got home after school, I would go to my room, drop my bag, and jerk off to the thought of her. Since then, I could really only imagine Alyssa as I would jerk off.
As our conversation ended, we exited the school, finally juniors. The buses were lined up and everyone was getting on.
“I gotta go.”
“I take the bus to get home.”
“How about I come along with you?”
“But what about you getting home?”
“It’s alright. I live around the corner from Dairy Queen.” Before I continue, Dairy Queen was one of the local hotspots.
“Really? I live around there too.”
“So about going with you on the bus?”
“Sure, if you’d like to.”
We get on the bus and I decide to get off a couple of stops early, because it’s a nice day. A habit of mine is to get off a couple of streets before mine to take a walk. Alyssa comes with me, and we just talk about stuff like family, interests, etc. It turns out that we’re both pretty similar, liking the same kind of music, sport teams, etc. We get to my house, and I get in to find my mom.
“Kevin. If you’re at the door, can you come into the kitchen?”
“Sure mom. I brought over a friend, too.”
We both went into the kitchen when the following occurs.
“Well, look at this. The best man and the maid of honor walking in together.” my mom said.
“Wait, what?” both Alyssa and I said. That’s when Alyssa’s dad came into the room going behind us and got both of us in a bear hug. Alyssa screamed, while I said, “Wait, what is going on here?” while being swung around.
“Hey there, kiddo.” Alyssa’s dad said.
“Dad. What’s going on here?” Alyssa asked her dad.
“We both had a talk. And we decided who the best man and one of the bridesmaids would be.” my mom said.
“So you two are getting married on the 14th?” I asked my mom.
“That’s right. And Kevin, you’re going to be the best man at the wedding.”
“Alyssa, kiddo. You’re going to be the maid of honor at the wedding.”
“What? So that means…” I said as turned towards Alyssa.
“That means we’re going to be stepsiblings.” Alyssa said as she turned toward me.
After a while, and me being stunned at the new information, my mom asks, “What’s wrong, honey?”
“So much to take in at one time. By the way, when are they moving in?”
“They’re moving in on Saturday.”
“Besides, today’s Wednesday.” Alyssa said.
“Kevin. Why don’t you give Alyssa a tour of her future home?” my mom asked.
“Sure.” I said, and turned to Alyssa. “You ready?”
“Sure.” I then left with Alyssa to give her a tour of the house.
It wasn’t a very big house, but not small either. It was a two-floor (three-floor including the basement), 4-bedroom, 2-bathroom house. My mom and I used two of the bedrooms as storage. There was a bathroom on each floor above the basement. And my mom’s room was on the first floor, right by the bathroom. Then there was the living room and den. The second floor consisted of my bedroom, the other bathroom, and the other two bedrooms. The second floor after the stairs was basically a straight-lined hallway after facing left. There were 2 doors on the right, and 2 on the left. My room faced to the right, as one of the bedrooms for storage was connected to the bathroom.
“So, which one will be my bedroom?” Alyssa asked.
“Depends. Which one do you want?”
“I’ll take the one that’s connected to the bathroom.”
“Sure. We’ll get that cleaned out by Saturday.”
At that time, our parents called us down to the living room.
“Kids, we’re gonna go out tonight, so it’ll be you two here alone. We left some money in case you two get hungry.”
“Mom. I know the deal. And I’m pretty sure Alyssa knows the deal from her dad.”
“Numbers are on the fridge for emergencies. If anything happens, call one of us. We’ll be back around 12:30 or 1:00. Have fun.”
“You too.” We both said, and our parents were off. The clock read 7:15.
“So…what do you want to do?” I asked.
“Hm…let’s just stay in and watch a movie or something.”
“Sure. Why not?” I said. “When do you want to order pizza?”
“Let’s order now, and then we can start the movie when the pizza gets here.”
“Sure. What do you want?”
“Let’s go with half cheese, half Hawaiian.”
“No prob.” I ordered the pizza, and during the time it took for the pizza to get to our house, we looked for a movie. We ended up deciding to watch The Departed, mostly because she’s never seen it before. We pop it in the DVD player connected to the TV when the pizza arrives. We pay the pizza guy and start watching the movie.
While the movie was playing, I felt Alyssa snuggling up and getting closer to me. I was getting a major hard-on as a result. All I could do was bringing her closer and hope that she didn’t notice or feel my bulging tent. She then decides to rub her hand on my thigh and rub her boobs around my chest. “Oh god, this feels so good, but it’s wrong. She’s gonna be my stepsister. I can’t do this.” I thought.
Around an hour into the movie, I end up getting a phone call and she put the movie on pause. To the person who called: way to kill the mood. I answered the phone, and it was my boss asking me to come to work. On my day off of all times!!! I actually work two jobs; one at Five Guys, a burger place, as a cashier and a cook (depending on timing), and the other at Roche Brothers, a grocery store, as a casher and at the bakery section. I work at Five Guys year-round and at Roche Brothers as a seasonal worker during winters and summers. I look up at the clock. It said 8:25. I went up to my room and got changed into my work clothes.
“Wait. Where are you going?” she asked.
“I got called in for work.”
“You work there?”
“How come I never see you there?”
“I’m either cooking, on break, or it’s my day off.”
“When will you get back?”
“Probably around 10:30 or 11. Will you be alright by yourself?”
“Just in case…” I then go to a storage room to get a blanket, a pillow, and my running gear from my room and place them on the couch. “If your dad gets too drunk and can’t bring you home, you can crash in my room and I’ll take the couch for the night. Chances are he’ll be sleeping with my mom. ”
“I thought he was already sleeping with her since their first week together.” she said, jokingly.
“I guess I walked right into that one.” We both laughed.
“And what about that?” Alyssa asked, pointing to my running gear.
“I go for a run in the mornings. You can join in if you want.”
“Sure. I’d love to.”
There was a slight pause before I decided to say something.
“Guess I better get going.”
“I guess you do.” Alyssa said.
As I got to the door, I realized that I forgot something, and went back to Alyssa.
“Aren’t you gonna leave?” Alyssa asked.
“Forgot to give you my number in case you need anything.”
We swapped phones and input our numbers in case something occurs.
“Well, I better get going. For real this time.”
“Yeah. I’ll…see you later.” she said, sadly. She goes in to give me a hug, and I figure why not. She whispers in my ear, “We’ll take care of this later.” as she rubs her hand on my bulging dick.
I leave, and drive off to work…on my day off. Honestly, when you have a day off from work, and then get called in, that’s just a complete buzzkill. I get to work 10 minutes after I left home, and before I walk in, I call Alyssa. I knew I had to try and act as if nothing happened, even if I couldn’t be convincing of it. All I asked her to do was to get my gym shorts and t-shirt that were on my bed in the bathroom by her future room by the time I got home. She said she would, and ended after she called me big brother. What really bugged me was that she said big brother in a flirtatious and seductive tone.
When I entered, the first person I run into was the manager currently on duty.
“Why the hell are you late?”
“I had to make sure my stepsister-to-be was OK. Besides, who the hell calls an employee to work when said employee has the day off?”
“Watch your mouth!!!” my manager said angrily.
“Yes, sir. Sorry, sir.” I said, begrudgingly.
“Now get to work!!”
As you can tell, I hate my manager. At least this one. We have a couple of managers, but normally, only one or two are on duty at one given time. It’s just my luck that the manager on duty is a complete asshole to everyone. I went to work as a cook for this shift. I couldn’t keep my mind off of what happened in my living room. After half an hour, my friend Amanda came in the room and snuck up behind me.
Going off story for a moment, I should describe Amanda. She is a friend of mine in school, and as of right now, the shift supervisor. She’s normally a cashier or cook, like me, but she’s a shift supervisor depending on who is working at the current time. She’s 5’4 brunette, 16 years old, with hair going down to her shoulder blades, 34C or 36C boobs, not sure, all I knew was that she looked like a C cup, and a cute bubble butt. Right now, she’s kind of like my boss, and she is looking fine in the work uniform. She’s also a good friend of Alyssa’s. We’ve been in a couple of classes together, and we’ve had an on-and-off relationship throughout high school so far. Right now, it’s been off. Anyway, back to the story.
“Guess who?” Amanda said, in a playful, yet seductive tone.
“Yep. How’d you know?”
“You’re the only one who does that to me.”
“Yeah. Besides, why are you working on your day off?”
“Got called in.”
“Who else? Dave the Douche.”
“Yeah. He really hates you.”
“I don’t even know why.”
“Me neither. By the way, you think you can get to the break room within the next couple of minutes?”
“Sure. Why though?
“I…uh…just need to talk to you about something.”
“Sure. I’ll meet you in the break room in 5 minutes.”
I ended up getting someone to cover my station while I went in the break room. The clock there read 9:23.
“Here. Take this.” Amanda said as she handed me a soda.
“Thanks. So what did you want to talk about?”
“Well, I wanted to know what you had planned for the summer.”
“The summer? Not doing summer work.” We laugh at that remark. “But in all seriousness, my mom’s getting married in a couple of weeks.”
“In a couple of weeks.”
“You think I can tag along?”
“I don’t know. I mean, the guy she’s marrying has a daughter, and she’s the maid of honor.”
“The best man and the maid of honor are supposed to dance together at the wedding.”
“Just who is the maid of honor you’re supposed to be with anyway?”
“Wha? So is that why you two were together after school today?”
“Oh no. We just found this out today.”
“And you’re not going out with her?”
“Oh god no. She’s way out of my league. Besides, she’s gonna be my stepsister in a few weeks. Even if I did, it’d ruin the whole thing between our parents.”
“They’d break up. My mom would stay in her room for a couple of days and cry. And I’d feel guilty thinking that I did something that ruined the relationship. After what happened last time, I don’t even want to think what would happen.”
“What happened last time?”
“I don’t even want to go into detail about it. By the way, why are you even interested in that stuff?”
She then goes so that we’re standing in front of each other, and then proceeds to kiss me. I was shocked and pushed her away.
“What are you doing? We can’t do this anymore.”
“Why not? We went out with each other before. Besides, it looks like you enjoyed it.” She said, rubbing my now forming hard-on.
“If you don’t go through, I’ll yell rape.”
“Go ahead. You don’t have the guts.” I said. Bad decision on my part.
Amanda went to the break room entrance and proceeded to yell when I ran to stop her.
“Guess I was wrong on that one.”
“Now, where was I?” she said, as she was rubbing my hard-on through my pants. “If you don’t want me to call rape, I need you to do two things.”
“What are they?” I asked, in a struggling tone as I tried not to explode in my pants.
“One, we go out Saturday night.”
“Two, we do it. Right here, in the break room, right now.”
“What?! We can’t do that. Especially here of all places. We’ll get caught.”
That’s when Amanda kissed me again, and having no choice, I kissed back.
“Your head may be saying no, but another part of you is saying yes.” She said in a flirtatious tone. “Plus we should take care of this before you go back to work.”
“How about I take care of this first?” I asked, as I worked my hand and started to rub her pussy through her work uniform.
“Oh god this feels good.” Amanda said through her heavy breathing. She was also rubbing my dick through the entirety of it.
“I got a better idea.” I said, as I picked her up and laid down on the table so that we were in a 69 position.
“Oh, you naughty boy.” Amanda said, jokingly. I then pulled her pants down to her knees and start playing with her pussy through her panties.
“Oh god! Don’t stop!!” she said, through even heavier breathing. “Two can play that game.” She said afterwards, unzipping my pants and taking my 7” dick out.
“Holy shit, it’s huge!!!” Amanda exclaimed. “Looks like Alyssa’s been missing out. Oh well, her loss.” She then proceeds to lick my dick. I wince back in pleasure.
“You like that, don’t you? I got something else for you, too.” She then starts sucking my dick.
“Oh god that feels good!!!” I say in pleasure. “But I know something that’ll feel good for you.” I then pull down her panties and start to finger and lick her now exposed pussy.
“God that’s turning me on so bad!!!! I know something that can even this out.” She said as she started fondling with my junk while continuing to suck my dick.
“Oh man. If this keeps up, I’m not gonna last much longer.” I thought. “If you’re gonna play that way, then I guess I’ll do this.” I then started to rub her clit. She shrieked for a moment when she found out what I was doing.
“Wait. What are you...” was all she could say before wincing back.
“It seemed like you were upping the stakes a little, so I thought I would do the same. Besides, it looks like you like this a lot.”
“I’ll make you pay for that one.” She said as she then continued to suck my dick and fondle my junk, except she did it harder. All I could do was to continue what I was doing. After a couple of minutes, I could feel my balls tighten and Amanda’s pussy shivering wildly.
“Shit!!! I’m gonna cum.” I said, struggling to have this last longer.
“Fuck!!! I’m gonna cum too.” She said, as we lasted a few more seconds till the two of us came together. I came in her mouth and she came on my face. She was shocked that I came a lot, and to be honest, so was I. When the two of us were going out with each other, we went no further than making out; maybe feel each other up when we were buzzed. And now we were on third base, potentially scoring, and at work of all places. She gets off and lies next to me when we start talking.
“Holy shit!!!That felt so good.”
“I not gonna lie: it was great.”
“How about warning me the next time you jizz?”
“I did warn you. You chose to keep sucking me off.” At that time, I was getting hard again.
“Looks like your friend wants to play again.” Amanda said. “How about we take care of it right now?” she then proceeded to spread her legs.
“Let’s.” was all I can say, before “Wait.” I said.
“I don’t have a condom.”
“Don’t worry. I’m on the pill.”
“Alright then. Just remember, we’re still exes, even after we’re done with this.”
“You don’t have to tell me twice.” She said. I then proceed to insert my dick inside of her pussy slowly. After I get about 2 or 3 inches of my dick inside, she’s biting her lip in pain.
“I’m alright. It’s just that…”
“It’s your first time?”
“Yeah. I assume it’s the same for you too.”
“Yeah. Now let’s hurry before someone comes in here.” I proceed to fully insert my dick inside of her and I was shocked that there wasn’t blood leaking onto her leg. Amanda saw my face and said “Don’t you remember? I told you that I got into an accident that broke my hymen when I was younger.”
“Oh. Must have forgotten. My bad. Anyway, we gotta finish this quick.” I then proceed to thrust my dick in and out slowly at first. She was biting her lip when I started to move, but got used to the feeling as it continued on. She was heavily breathing when I sped up.
“Looks like someone’s gotten used to this.” I said, noticing that she was heavily breathing. I then proceeded to go faster as I started to lift her shirt and bra to reveal her boobs. “Guess these should get some attention too.” And with that I start to play with her boobs while my dick is inside of her.
“Holy shit!! Fuck me harder. Fuck my pussy harder!! It feels so good!!!”
“Oh fuck!!! You’re tight. Makes me want to fuck you harder.” I said. I then fuck her as hard as I can, and she starts to moan.
“Fuck!!! I’m gonna cum!!! I’m gonna cum!!! I’m gonna cum!!!” she whispered in my ear.
“Shit!!! I’m gonna cum too!!!”
“Cum inside!!! I want to feel it inside of me!!!” We both have our orgasms and I end up shooting around 3 or 4 loads inside of her. Not much, but what can I say? It’ll get better with experience.
After that, we hear someone knocking on the door.
“Holy shit. It’s Dave.” I whisper.
“Hide under the table and walk out while I distract him.”
“That can be taken the wrong way.”
“Stop joking and follow my lead.” We fix our clothes and the manager comes in. I was nowhere in sight.
“What the hell is going on in here?”
“Oh. Nothing sir.”
“What the hell was with all that screaming?”
“I…uh…killed a bug that startled me. That tricky bastard.” Amanda said. The manager went up to her and started to yell at her while I ran for it. I gave her a thumbs-up sign on the way out as a way of saying thanks. The clock read 9:57 when I got back.
After an uneventful half an hour, we closed up. Before I left, I caught up with Amanda in the parking lot.
“Hey. What’s up?”
“I just wanted to say thanks for taking one back there for me. I really owe you one.”
“So does that mean we’re still good for Saturday night?”
“I’ll have to be honest. I don’t know.”
“Because Alyssa’s moving in that day and I don’t know how long that’ll take.”
“Friday night, then?”
“Sure. That’ll be wonderful.”
“Kevin. I have to tell you something.”
“I’m all ears. Fire away.” Oh shit. Is she gonna say she’s pregnant? What the hell is going on here?
“There’s two things. One, I’m not really on the pill.”
“Fuck!!!” I exclaimed. “So if you get pregnant, we’re basically screwed?”
“Yeah. Though it’s a relatively safe time of the month for me.”
“You should check anyway.”
“That’s the plan. And two, well, it’s about Alyssa.”
“Before you talk about the second thing, I just want you to know, that if you get pregnant, I’m not gonna run for the hills and abandon you like everyone else would. I’ll be right where I am right now.”
“In a parking lot?” she joked.
“Funny.” I said sarcastically. “But in all seriousness, where I am now…is by your side.”
“Thanks Kevin. It meant a lot to hear that from you. About the second thing and Alyssa…”
“What about her?”
“The truth is, she likes you. A lot. And I don’t mean as friends.”
“She’s liked you since freshman year.”
“So basically around the time we started going out?”
“Why would she set us up with each other?”
“She never realized it until we did go out. And she is tempted to screw your brains out as much as I did.”
“I should’ve known.”
“What do you mean?”
“Before I came here, well, Alyssa and I were watching a movie. She kept scooting closer to me, and she was rubbing her boobs. Plus when I said I was leaving, she gave me a hug, and rubbed my hard-on. I tried to get it out of my head.”
“Looks like she’s taking full advantage of you two as future siblings.”
“It’s not like I’ve thought about it.”
“Yeah. I liked Alyssa in that way. But I always thought she was out of my league, and didn’t want to go out with me. I just kinda gave up on the idea of me and her. When she introduced me to you, I just…well...I kinda grew on the idea of wanting to know you, and then we ended up becoming boyfriend and girlfriend. That must have drove her crazy.”
“At first it didn’t. Then she realized you were a great guy. I mean, a lot of the guys at school were pressuring for sex. You never pressured anyone for anything, especially with me while we were dating. To be honest, one of the reasons I broke up with you was because of how Alyssa felt.”
“Here I thought that all this time, it was me who caused the problem.”
“You were only a part. Anyway, the two of us didn’t want to fight over you, so we kinda left it at a neutral state.”
“I must have been a grade-A jerk to her back then. I never knew she felt that way, and here I was making you feel special. You definitely are, don’t get me wrong, but I was also going through some motions. Like if I had to choose between the two of you kind of motions.”
“Who would you have chosen?”
“Truth is, I still haven’t found that out yet.”
“Bummer.” She checks her watch to see that it’s 10:48. “Holy shit. I gotta get home.”
“Same here. By the way, we still good Friday night?”
“Yeah. Big doofus.” She says, playfully punching me in the arm.
“Ow!!! Big bully.” I jokingly say. We both laugh at that, and then parted ways.
I drove home, now knowing what Alyssa actually felt, and why she did all those things back home. I was ready to confront her and tell her how I really felt. Only…
When I got inside my house, I took off my shoes, and I heard a sound coming from upstairs. I went up quietly to find out what it was. When I got to the top of the stairs, I find that the light in my room was on and the door was slightly open. I quietly went to check it out, and the sight that changed my life was right in front of me. Alyssa was naked and masturbating on my bed.
“I know I shouldn’t be doing this. He’s gonna be here any minute, but I can’t stop. It feels so good. I kinda wish that he could walk in on me and fuck my brains out. Oh god this feels good!!!” she said as she was masturbating.
“Oh god Kevin. Stick your big cock inside of me. Fuck me hard. I want you to fill my pussy with your seed!!! I’m gonna cum!!! I’m gonna cum!!! I’m gonna…UUUUUGHHHHHHHHHHHHH!!!” She had her orgasm and collapsed on my bed. She was then staring at her hands.
“I wonder how different it would be if his dick was inside of me instead of my hands.” She thought out loud. I found out she was using my bed AND my PJ’s to get herself off. I went downstairs into the kitchen as quick and quiet as possible. I went to the fridge and got some water. I closed the refrigerator door loudly on purpose so that she could hear I was back.
After a couple of minutes, she came down, fully clothed again.
“When did you get back?”
“A couple of seconds ago.” I lied. “Want anything to drink?”
“Water, please.” I handed her a water bottle.
“What have you been up since I’ve been gone? Finishing the movie?”
“Actually, I didn’t finish the movie. I went into your room, chatted with friends online, and then I ended up on your bed taking a nap.” she lied. Well, she was telling the truth about the movie. “Oh. Before I forget, here’s your PJ’s.”
“Thanks. By the way, Amanda wanted to ask if you wanted to hang out on Friday.”
“No thanks. I’m gonna be packing then.”
“K then. You wanna finish the movie after I wash up?
“Sure.” she said, a little flustered.
I then went to the bathroom, knowing that I couldn’t look her in the eye, and can’t view her in the same light again.