My Sister, And Her Friends Ch. 01

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Sister helps an 18 year old boy becomes a man.
4.3k words
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Part 1 of the 5 part series

Updated 11/01/2022
Created 05/21/2013
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mojavejoe420
mojavejoe420
1,072 Followers

So I've been masturbating ever since I can remember. I thought I was a sex freak, but it turns out it wasn't all that abnormal. This story takes place in the later 80's. I was living at home with my mom (ugh) and sister Vickie. Of course, Vickie is hot. I wouldn't be writing about her if she was a skank. But she's not the real story, you'll see. It's going to be a slow beginning, but give it a shot...

I've just turned 18 years old. Dad moved out years ago, mom has let herself go to hell. She works at a doctor's office as an office manager, but usually only works till 3 pm so she can be home for us kids. Whoopee. My sister, Vickie, is 21 and we both attend the State College up the road a few miles. The rich kids all went to the "University of XXXX" but we had to go here. It's kind of a drive-in college, some kids are in dorms, but not us. It's pretty much like high school, meaning that it sucks.

My high school career was uneventful. I was geeky, gawky, bad skin, and painfully shy. Oh, and throw in skinny and short, also. I went to my senior prom, with an actual girl, but didn't even get to second base.

This past summer, I grew 4 inches (in height) and my muscles started filling in. My skin is mostly clear, but I'm still dreadfully shy. I'm very nice and respectful of women, and that's gotten me nowhere.

So Vickie and I have similar class schedules, we usually carpool to school except on Fridays. She has a late class and I get out early. I should mention my guy friends went to the university, sometimes Vickie's friends and I hang a little, but not very often.

So it's Friday. I like Fridays. I have the house to myself, it's about the only time. I just bought my first adult magazine called 'Velvet' which I'm dying to check out.

Remember, this is the 80's and we weren't rich. No internet yet. No VCR. No porn. No cell-phones. Jack-off material consists of Cosmopolitan magazines, Sears catalogs (full figured bra department) etc. So, not much.

My routine, since school started, is to go into my sisters room, get naked, spread out my stuff, and then hump her bed like crazy. You see, her bed spread is some kind of fabric that is very soft and silky smooth. It feels fantastic on my cock. I pile up a few pillows under my chest (I pretend they are big tits) and when I'm ready to cum, I roll over and shoot my sperm all over my chest and stomach. I usually will grab one of her bras or bathing suits, too. I like to run my cock in the bra cups, imagining my cock touching tits... and yes, Vickie is a double-D so there's a lot of cup.

I'm always very careful, I put things away perfectly, don't make a mess or a wrinkle, nobody is the wiser.

So there I am, humping her satiny smooth spread, occasionally rubbing Vickie's D-cup bikini top on my cock, frantically turning the pages of the 'Velvet' magazine and some lesbians. Jesus it's a good day. No imagining what tits look like, I'm seeing some right here! I try to think what my sister's tits look like.

That feeling starts up, from far away, it's getting closer and closer. Yep, it's time to turn over. Time to shoot my red-hot sperm all over my chest. To tell the truth, I have to be careful or it will hit my face or go onto the floor (yes, it's happened before).

I roll over, grab my cock in her bikini top, give two hard strokes, and here cums my beautiful orgasm...

"WHAT THE FUCK ARE YOU DOING??!!!!" yells Vickie.

Holy shit! She's home early!! Oh Fuck!!!

"Uh, um..." I stammer as cum shoots out of my cock, I'm scrambling to get away, but cum is shooting out. It hits my face, goes on the bed... Vickie's hollering something at me and gets hit with a spurt...

I truly want to die of embarrassment. Yeah I know, you tough guys would be all over it ... "oh I'd fuck her right there". Well, I'm a sensitive guy, and this is my sister, and this really embarrasses the shit out of me.

I run into my room and try to shut the door. Vickie is right there calling "Filthy pervert" and stuff and throws the magazine at me. She wants to know more about this.

"I was just... I was..."

"I know what you were "just" doing. Don't do it in my fucking room! And what are you doing with my bathing suit? You fucking pervert!"

She yells at me some more, I don't know what about. Slamming the door, she stomps off yelling "Wait till mom comes home." Mom, Jesus. She will make my life a living hell if she hears about this. Christ, I'm already dead.

Later, Mom is making dinner. Vickie knocks on the door and says to come set the table, my job that week. I tell her I'm not coming, I don't feel well. She says I better, or else. Plus, it's meatloaf. For all of Mom's faults, she makes a killer meatloaf.

I drag myself out to the kitchen, make nice with mom, and start setting the table. Vickie hip-checks me into the cabinets. Mom asks if i'm alright. Yeah, just tripped. She is prattling on about her stupid day at work. Vickie is behind Mom as Mom is at the stove. Mom, can't see her. Vickie makes the international sign for jacking off, thumb and fingers in a circle, stroking up and down, and points to Mom. She's hinting that I jack off to Mom.

I make this exaggerated face, like i'm disgusted, which I am. That's fucking gross. Hey, you may be into that, fine, I don't care. But if you saw her, you wouldn't be into MY Mom, either!

Anyway, Vickie nods her head at me, like "yes you do". She holds her hands in front of her, like she's holding enormous boobs, points to me like I want Mom's boobs. I shake my head, No!! Vickie then makes a peace-sign, puts it up to her mouth, and sticks her tongue in, like I'm "Eating at the Y" and points at Mom, as if that's what I want to do. I VIOLENTLY shake my head no. I'm also about dying as I'm trying not to laugh. Mom keeps talking while Vickie repeats a few of these motions, all the while mouthing the word 'Pervert" to me.

"Hey Mom", Vickie says. "Guess what I caught David doing today?"

Gulp. the fun just left the building.

"Oh, what was that, dear?"

"I came home early from school", Vickie continued. "And I found Davey boy in my room!"

Oh Jesus I'm so dead.

"He had completely vacuumed my room!"

What? I'm not dead! She didn't rat me out!

Later that night, she was getting ready to go out with her friends, Vanessa and Michele. We share a bathroom, it's called a "Jack and Jill" bathroom. The bathroom has two doors, one to each of our bedrooms. Vickie's in there and calls to me.

"Come here." I saunter in to the bathroom where she's fixing her hair. She looks awesome...

"Stay out of my stuff. And my room. Seriously. Or we will have a problem. Now get out."

Ok, fine.

Sunday night, we all went to our rooms after watching TV. I pull out my magazine and start humping my own sheets. They aren't satin, but they will do the trick. I guess I bump the headboard a little, which makes a rattle.

The phone rings. In our house, we have three extensions: Kitchen, Mom's room, and my room. Vickie has a separate line in her room.

I holler to Mom, "I GOT IT."

"Hello."

"Hey pervert."

It's my fucking sister, calling me from her private line.

She continues, "What are you doing in there? I'm hearing noises through the wall..."

"Um, just reading my biology book"

"Yeah, right. Biology. Is it, uh, Lesbian biology?"

"No... it's um, plants, ya know. Stamens and pistils and stuff..."

"Right. So, pervert, you like looking at naked girls."

"Uh, well, I am a guy..." What the hell? We don't talk about stuff like this!!

"I'm guessing that since you had my bikini top wrapped around your cock, maybe you were thinking about something or someone in particular?"

I flushed with shame. I kept quiet.

"Were you thinking about my tits?"

I'm staying quiet.

"You were, weren't you. You were thinking about my big tits."

Crickets.

"Answer me... now!"

"... yes. Yes, I was thinking of what your big tits looked like... Sorry."

"Fucking pervert. Are you hard now? Answer me, don't fuck around"

"Yes."

"Stroke it."

"Whu... what?"

"You heard me, stroke your cock. Now."

"oh... ok..."

"Or maybe you should fuck your bed, like you were doing on my bed. Do that. Fuck your bed. Make some noise."

I start humping the bed, making the headboard hit the wall. I'm breathing heavily into the phone.

"Good boy. You like big tits, don't you... Big soft tits. Mmmm... I have big tits. They are double-D, you know."

"yes... I know..." I manage to grunt out. christ here comes the feeling

"Tell me. Do you want to see my tits? My soft tits... with hard nipples..."

Humping the bed... the build up is coming

"Tell me! Do you want to see my tits or not?"

"Jesus Vickie! Yes! Yes I want to see your tits!" And with that, I just barely rolled over in time to not cum in my own bed. Groaning, I shot spurt after spurt of steaming cum all over my stomach and chest.

"Good boy. Now don't move. Do NOT fucking move."

She hung up the phone. What the fuck?

The bathroom door clicks and opens. Vickie comes into my room with a box of kleenex for me.

"Wipe up your nasty self." She watches as I use seven or eight kleenexes to wipe the cum from everywhere, including the phone I was still holding. I didn't hide my cock or anything, which was a big step for me. i squeezed it from the base up, getting out the last drops. It didn't really go soft, either, as Vickie was in her hot-weather nightie.

That thing was fucking sheer. I stared at her barely concealed tits.

"That's enough. go to bed, pervert."

*****

So we went to school on Monday as usual, never mentioning a word about anything. I jacked off like clockwork, three times a day. Sometimes I would rattle the headboard, Vickie would bang on the wall. I can NOT stop thinking about her talking to me about her tits, and standing there in her nightie.

Friday comes along. Driving home from college, I have mixed emotions. I'll be alone, which is good, but I can't go in Vickie's room. I have a feeling she will know If I've been in there. She'll set a thread trap or find a pubic hair or something...

I get home, Mom's at work (she works later on Friday's), and Vickie's home!

"Thought you had Economics Lab this afternoon?"

"Nah, professor was sick."

"Hmmm." I said.

"Yeah," she said. "Hmmm."

Awkward silence.

"Tell you what," she says. "Go to your room and put on your gym shorts."

I went to my room, wondering what the hell this meant.

"Come into my room when you're done", she hollers.

I amble in a minute later wearing my shorts and a t-shirt.

"You don't listen very well. I said gym shorts. Take that shirt off."

"Fine, jeez..."

I notice she has something in her hand, something chrome, metallic. It looks heavy.

"Lay down on the bed, your head on this pillow", she indicates.

Ok...

"Left arm up to the headboard. Don't move."

Ok...

Swiftly, deftly, she takes the metal from her hands. She clamps a handcuff on my left wrist. I yank my hand down, away from her.

"What the hell, Vickie? Handcuffs?"

"Shut up now. Just go with it."

Reluctantly, i let her cuff my left hand to the brass rail of the bed.

"Comfy?", she asks.

I nod in the affirmative. My left arm is resting on pillows, it's not bad, I guess. My right hand is free...

"Locked in?"

I pull on the cuff. It digs into my wrist a little. But I'm chained in, I can't get out.

"Alrighty then", she says. "Since you are such a pervert, but otherwise a good guy, I figure I should help you with your problem. Now then, take off your shorts."

I don't move for a moment. So she tells me again, firmer this time.

"Take them off, or you'll be very, very sorry"

Well I don't want to be sorry, sure enough. With my free right hand, I struggle out of the shorts. Have to do some gyrations, but they are off.

I'm naked on the bed. In front of my sister.

"You know, your cock isn't half bad... for an asshole, that is."

"Uh... thanks?"

"Get it hard. Now. Stroke it. You're going to jerk off for me."

"Vickie, look, I'm sorry about the other day..."

"Stroke it now!" She grabs my hand and puts it on my cock! I start stroking it.

I stroke it for a bit... Nothing happens. I'm too nervous. I look at her with, I guess, a pathetic face.

"Oh... alright. Look all you want."

Vickie stands up, thrusting her chest out. She's got a hot blouse on. Reaching behind her, she un-does the buttons and takes it off. Now, she's standing in front of me in her designer jeans and black bra.

Something happens in my groin.

"Not so nervous now, are you?" She smiles at me.

Her cleavage is gorgeous. Bending over towards me, she pulls on her bra, showing more cleavage to me.

I'm fully fucking hard now, slowly stroking. Some pre-cum has arrived at the tip of my cock. I work it into my hand that is clamped down so very tight on my dick. Vickie continues to rub her bra-covered tits.

Staring into my eyes, she reaches behind her back... and unclasps her bra. I can barely breathe.

Vickie leans forward a bit, the straps falling from her shoulders. Cupping her breasts, the bra falls slightly away from her. But I can't see anything yet. She turns her back to me and throws the bra at me. I still haven't seen her tits yet.

"Use it," she commands. "Soil it."

As if I have no will of my own, I take her bra and fully sniff it... mmmmmmm... and then I rub my cock into the cups, streaking the inside of her bra with my pre-cum.

"Good boy", she says. "Now you're going to get just one minute. I suggest you make the most of it... Go!"

And with that, Vickie turns around and gives me a total and complete view of her spectacular tits. Double-Ds, as I've said before. She cups them, squeezes them, tit flesh spills out between her fingers. She mashes them, manipulates them, bounces them... holy fuck...

Tweaking her nipples, she reminds me... "15 seconds."

I'm stroking my cock so hard, my hand has a death grip on the bra cup surrounding my cock. Vickie takes her left tit in both hands... raises it to her face...

"Cum now for me..." she whispers.

Vickie extends her tongue and touches her nipple with it.

I just go fucking nuts. I didn't know that could happen! I'm convinced my orgasm may actually make it to the Guiness Book. Cum is flying all over me, her bra, the wall. long ropes of cum streak out from my cock. Jesus Christ it feels so good... exquisite. OMFG, as we say today.

"Look what you did to my bra," she sighs. It's a friggin mess, of course, cum in the one cup, cum on the outside of the other.

Vickie take the bra from my hands, giving me the 'tsk tsk' sound.

"Sorry..." I manage, surprised because for a while I couldn't even speak.

Vickie takes the bra and the semi clean cup and, get this, wipes it INTO the cum on my abdomen. Then, she puts the bra up to her tits!

"Mmm, warm... good boy." She clasps the bra back together.

"Going to hang out tonight with the girls, maybe I'll give them a whiff of you."

I don't know what to fucking say. She's wearing a bra with my cum in it's cups. My cum is on her tits. I know, you already figured that out. I just like saying it. My cum on her tits...

"Mom will be home soon", says Vick. "Get out of here and don't bother me anymore, creep."

She tosses me the handcuff key and walks to the bathroom.

Stunned, I wipe up with Kleenex. I go back to my room and try to figure this out. Vickie gives me pleasure, but she also seems to want to humiliate me to some extent. I'm feeling a little un-manly, like I'm just her toy. But then, so-fucking-what. This is a great day!!

***

It's next Friday. Things are normal between Vickie and me (Vickie and I?). Normal in the sense that we don't talk about what happened last Friday. Not a hint. I whack off all the time, with Vickie's tits front and center in my imagination. She bangs on the wall sometimes at night when she hears me masturbating. That just makes me do it more.

At the college, she catches up with me and says she needs a ride home with me. Usually she goes with one of her friends, but that friend, Vanessa, isn't here today and Vickie has no choice but to miss class in order to have a ride home.

So, if I'm not mistaken, we'll be home alone again on a Friday afternoon.

The ride home is a little awkward. I'm wondering if we're going to do anything or what. Vickie is just reading her Econ book.

"What are you doing this afternoon?" she asks out of the blue.

"Uh... no plans... why?"

"Don't you have some friends to hang with or something?"

"No, my buds went to school in the city, you know..."

"Well, why don't you get a girlfriend or something?"

Where's Vickie going with this? Sounds like she wants me to move along or something.

"Well, those things take time. I don't have anyone right now, you know that..."

She sighs.

Getting out of the car at home, she stops for a few moments. Then she tells me to be in her room in 30 minutes, exactly. And to bring my new Def Leppard record. And to not wear any fucking clothes. I just nod.

A long thirty minutes goes by.

I knock and enter her room. Vickie isn't there. There's a note on the bed with the handcuffs, it reads:

"Play Pour some sugar on me.

Play it loud.

Cuff your left hand to the bed.

Don't fuck this up."

Pour Some Sugar on Me, an awesome tune from Def Leppard. I guess she wants it on! this might be fun...

I crank it up good and loud, then quickly jump on her bed and clamp my left hand in. The song starts with an intro, and then the drums kick in strong.

In time with the drums entrance, Vickie pops out of the bathroom door wearing this freaky black leather teddy kind of a thing, g-string, high heels, leather wrist cuffs with metal studs, and finally, a leather choker collar also with studs.

Her hair is done up in full 80's 'Big Hair' mode. And she's got some outrageous Rocker chick makeup on.

Anyways, she comes flying into the bedroom, dancing around in perfect time with the music. She reminds me of the movie 'Flashdance' with all her crazy and sexy moves. Very soon, she yanks open her teddy, letting her tits spill out. As she gyrates around the room, her tits bounce and sway and drive me fucking crazy.

Finally, we're getting to the chorus, the "Pour some sugar on me" part. She kicks off her shoes and gets on the bed, and stands right over me. Her feet are like at my sides. I take my hand off my cock and start to feel her left calf. She glares at me and shakes her head 'no'. I re-grab my cock and she continues to gyrate above me.

What an awesome sight, her tits swaying above me... she leans forward against the wall, like she's being arrested or something. Those beautiful tits are in full hang mode. I'm stroking and stroking. I think I may need a blood transfusion because there's none left in my main body, it's all in my cock.

She lowers herself down onto me, her tits just out of reach of my face. She pushes my forehead back down into the pillows and laughs. Now she's sitting on my chest, straddling me. Her pussy is hiding in the G-string, but it's literally inches from me. i can smell her.

I try to move my arm to grab her ass, but it's clamped down by her leg. I can only grab my dick. So I keep stroking, but this can't go on for very long.

The chorus comes around again. Vickie yells over the music, "Cum now. Do it"

Then, she sings aloud with the chorus, "Pour some sugar on me" as she cups her breasts for me. She pulls them to her face and frantically licks her nipples, back and forth to each one... She repeats the chorus with the band a few more times.

I arch my back as my orgasm hits me full force. Huge spurt after huge spurt hits Vickie's back and ass cheeks. I jerk again with cum spasms, Vickie almost falls tits first into my face, but catches herself, dammit.

mojavejoe420
mojavejoe420
1,072 Followers
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