My Sister Billie

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The first plan doesn’t work, but the second does.
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MDSW
MDSW
519 Followers

Writer's Notes:

All characters in this story are 18 years old or older. Thank you all for the comments and keep them coming. And vote!!! Enjoy the story.

The anal sex described herein does not conform to proper standard practices. Do your due diligence before you engage it the first time. It can feel great, but it can also feel bad so be careful. Educate yourself before indulging.

* * * * *

Mike and Billie are twins in their senior year of high school and they just turned 18. Becoming adults is a one time thing so they do some serious celebrating. Mike laughs with Billie most of the time and they have loads of fun.

Her sense of humor can be incredibly funny and she is definitely on a roll. Mike has a few good one-liners of his own and gets a lot of laughs as well, and still have a great time. They don't get in trouble, but they do have some serious fun. His sister always does. She's the life of a party, fun to be around and even Mike enjoys her company.

On the another hand, Billie is a fox by anyone's definition. She knows it, but doesn't flaunt it. She's not that type of girl. She's slender with a smile that can turn pitch blackness to daylight. She's the best looking girl at school and Mike is proud to be her brother. He's also proud of her for being who she is as well as being his sister. Mom and dad also enjoy her sense of humor and so does Billie's best friend, Emily.

Emi is an only child. She turned 18 three months ago, but she's a grade behind them stemming from problems she faced before moving into this area. The problems she had caused her to be set back a grade, but she's doing better now that she's attending their school.

In contrast, Mike and Billie were born and raised here. They're fortunate enough to live a mile away from the senior high school and they often walk to and from school.

Mike is more the quiet type, the direct opposite of his sister. They are close, but not to the point he knows everything about her. He's more the intellect in the family, wanting more quiet than a maze of noise.

He reads a lot and enjoys most of the novels he reads. Yes, he does go out once in while with some friends and enjoys their company. He's not completely antisocial. Even though they remain close knit as a family, they also enjoy their individual privacy.

They're approaching their last ever winter break of their high school career and they can't wait. Billie and Emi decide to take a train and head south from a warm to a hot climate for their winter break week.

Billie asks him to go with them, but Mike decides to stay home and enjoy the serenity of an empty house, telling her he already made plans for the week. She knows what his plans are and she's disappointed he's not traveling with her. She will never tell him she knows his plan, but he knows she knows and she knows he knows, therefore, Emi knows too. Whatever.

Billie asks him several more times to go with them, but he politely refuses each time, saying, "Two's company, three's a crowd."

Mom and dad are also on vacation that week and they also decide to travel. They also ask him to go with them and again, he politely declines, citing the same reason he has given his sister. He doesn't hate or dislike his sister or his parents, but sometimes, Mike wants a break from the hustle and bustle of a busy home life.

He doesn't see it as a bad thing, it's just that there are times when he wants some peace and quiet for a change. This will be his big chance at achieving that and he wants to take full advantage of it, for his own sake.

A couple weeks before Billie and Emi depart for their anticipated vacation, Billie begins wearing more skimpy clothing around the house when mom and dad aren't home. Mike notices, but says nothing. He wonders why she's doing it, but shakes it off in his next breath, even though he would rather look at her than not. She is so sexy it makes his dick stiff, but he hides it from her glancing eyes.

Mom and dad plan on departing that Friday, taking some time off from work that day. Mike tells them he will take Billie and Emi to the train station and pick them up so not to worry. He doesn't have a problem helping out his sister when he wants to, and this is one of those times.

* * * * *

When Friday finally arrives, Mike is so excited in anticipation of having the house to himself he's higher than a kite. His sister knows this about him, but says nothing.

Mom and Dad have already departed for the airport by the time Mike and Billie get home from school. They leave each of them an envelope with $600 in cash in it telling them in a note not to spend it all in one place.

Billie is excited about her trip so he gives her hi-fives to support her. He turns on the tunes and they dance around the house, with total freedom in their minds.

Billie is a natural talent when it comes to dancing. She has the graceful moves and it looks as if she was born to dance, so he feels like he's dreaming as he watches her sexy moves. After a while, he returns to reading as she continues to dance. She's acting provocative with her dance moves and he's on the edge of blowing a hole in his shorts, but she's having such a fun time, he has no desire to stop her.

In a last ditch effort to get him to travel with her, she goes to her room, strips down, puts on a thong, a half t, no bra and returns to entertain him. She decides she's going to get him on the train with them tomorrow and she's willing to use her body to complete her mission.

When she returns, she mostly avoids eye contact with him as she shows off her charms beyond what he's ever seen before. She's all girl and he knows it. He can't help but notice her scantily clad body and he intentionally avoids eye contact with her, continuing to read. He does manage to get several good looks at her without her seeing him and his dick reacts.

She's one HOT girl and his cock gets so hard he has to conceal it. She's so sexy and dressed to kill, and he has to avoid falling victim. She isn't trying to impress him, she never has, never expressed a great deal of interest in him, so why is she doing this? Has something changed or is it just wishful thinking on his part?

Mike has to keep himself in check for several hours as Billie prances around the house, enjoying what she's doing to him. He knows she knows, but he doesn't encourage her. He reads so little it's not funny, but he gets several eyefuls of her luscious body. He has to adjust himself several times as well to keep his hardness concealed and definitely doesn't want to start something, then has to give it up in a few hours. Even though it's torture for him, he endures because of his desire to be alone, for a change.

* * * * *

The next morning, it's off to the train station, picking Emi up along the way. Being the protective brother he is, he remains with them until they board the train and depart.

After a final goodbye to his sister and Emi, he detects some sadness in Billie's eyes. She gives him another hug and finally speaks her mind.

"I don't want to go without you. Won't you come with us?" she says as she develops tears in her eyes.

"Under different circumstances, I might go with you, but I hope you respect my right to privacy as much as I respect yours. You'll be ok as long as you and Emi stick together. Ok, Sis?"

"Not ok. I still wish you were going with us."

"You two are going to have a lot of fun, so enjoy it starting now," he tells them.

He gives his sister another goodbye hug and hi-five, but the surprise is Emi also wants a hug from him. He gives her the hug she desires and she and Billie make their way to the train as the sadness slowly wears off Billie's face. She's hoping to have a good time on vacation, even if he doesn't travel with her.

After several more minutes, the train departs. He waves at them and they wave back when they see him, then they're gone.

Inside, he's cheering. The house is all his for a whole week. He drives to his favorite fast food restaurant on the way home to celebrate his short term freedom. He has no plans, just to relax and enjoy the solitude.

* * * * *

Arriving home, he parks his car in the garage, since Mom and Dad took their car to the airport. With the whole week to himself, he's ready for it to begin.

He gets his bathing suit on and heads to the pool, the perfect start to his vacation and he's so elated it's not funny. The weather here is not hot this time of year, nor is it cold, but he can enjoy the outdoors, swim in the pool and bask in the sun comfortably.

The rest of Saturday is peaceful and somewhat quiet, but he feels an emptiness in the house and wonders if he misses his sister or if its just him in a rare case of a loneliness. He listens to his favorite tunes and watches some music videos on his phone, prepares his own dinner and several other things that keeps him busy. He's doing exactly what he wants and enjoys every minute of it.

* * * * *

Sunday morning, while sunbathing by the pool, he receives a call from an ex girlfriend, something he never thought would happen in a million years. She invites herself over to keep him company for a while so he agrees, as long as she doesn't make a habit of it during the week.

Carol arrives less than a minute after they hang up. She must have been watching from the gate while talking to him on the phone because she lives about fifteen minutes away.

He hears the gate open and there she is.

"Hi, Mike!"

As she approaches, carrying a towel at her side, her figure stands out, wearing a skimpy bikini that shows her slender body exceptionally well.

Carol is a good looking redhead with a trim figure and sensuous curves. She's a couple weeks older than Mike and they went on a date a couple weeks ago. Nothing happened between them though. He didn't connect to her and apparently, she didn't connect with him either. They split up after only a couple days. Why she's here now is a mystery.

She's approaching so he stands to greet her. He's surprised to be on the receiving end of a very tight hug, something she never did when they dated for that short period of time. He returns her hug to let her know he's alive, but personally, he doesn't want this to go anywhere. She's not really a girl he wants to hang out with.

"Hi Carol. That was quick."

"It was. I must admit I knew you were home because I saw you sunbathing just before I called. When you said ok, I shed my shorts and T-shirt at the gate and came in."

He looks at the gate and sees her clothes there.

"Why didn't you wear your clothes all the way in?"

"Because I wanted to watch your eyes as I came in. If I didn't know any better, I'd swear you stripped my bikini off with your eyes."

He laughs and admits, "Yeah, I probably did, didn't I... Sorry about that. I didn't mean it as bad as it sounds, but you do look HOT."

"Thank you," she says as she smirks.

"That's cheating, you know, but I'll let you get away with it this time... Pull up a chair and enjoy the sun," he says.

"Thanks, Mike. Don't mind if I do."

They smile at each other, then he lays on his stomach while she lays on the lounge chair that's next to his and does the same. They lay there for a few minutes without saying a word to each other, then he alters their mood.

"Last one in is a rotten egg!"

Carol takes on the challenge and tries to beat him to the punch, but loses. He swims underwater to the far end of the pool and stands in waist deep water. She surfaces ahead of him, but doesn't see him until he surfaces.

Looking around, she spots him and swims straight to him. Standing in front of him, she puts her arms around his neck, pushes her tits into his chest and her lips to his.

She's being aggressive and he doesn't stop her, for whatever reason. In fact, he wraps his arms around her, but wants to know why she's being so aggressive so he breaks the kiss after about ten seconds.

"Sorry, Carol. Last we dated, we didn't make a connection, as I recall, so what's happening here."

"I know we didn't, Mike, but I just thought we can have a little fun for the afternoon. We didn't hate each other when we split up so I'm thinking you would be open to sex instead of a relationship."

He's awake now!

"You sure that's all you want?"

"Pretty sure."

"Then we have one, big, huge problem."

Her smile disappears from her face as he keeps his face serious as hell.

"What?"

"You have too much of your body covered, as I see it," he says.

Her smile returns.

"So do you. That can be fixed if you like," she says as she unties the string on inside of his suit.

This is the first time he'll have sex with an ex and it feels different to have casual sex with no emotional connection. He's not sure if that is a good thing for him or not, but he'll humor her this time and see what comes from it, if anything.

Not giving him a chance to make a move, she ducks under water and jerks his suit to his ankles. He steps out and kicks them away as she grabs hold of his cock and strokes it a couple times. When she surfaces, the smile on her face tells him she likes his cock, grabs it again and strokes it to her delight.

"You have a very beautiful cock. Feel like using it for a good cause?"

"Depends on what the good cause is."

"Sex with me, silly."

"Jeez, I'm so dumb sometimes. I knew that!" he says, feeling somewhat embarrassed.

"Everybody feels dumb sometimes."

"True... Now it's my turn to get you naked."

He pulls her close to him, reaches behind her, unties her bikini top and removes it from her sexy body. When her full tits come into view, he gasps. They're perfectly shaped with little sag, then he reaches for her bottoms and unties them. After he pulls it free of her body, she mounts him and his hands go straight to her ass, only to support her, of course.

The soft feel of her ass makes his cock transcend to hardness in a heartbeat, maybe two or three.

"Do with me what you want, Mike. I'm all yours."

They kiss and he kneads her ass as he walks her to the side of the pool. He sits her on the edge and gently pushes her to her back using a single finger, then she raises her legs to his shoulders.

He runs his hands over her soft body as she sighs and moans quietly. She feels so soft, warm, and wet, it pleasures him to make it happen for her. After all, she did come over just for sex, didn't she?

As his hands reach her nice, tight, firm tits, he kneads them as she makes it known she enjoys the pleasure. He bends over her to lightly suck on her nipples, then he bites them tenderly, alternating between them quickly. She gasps and moans pleasantries that he normally doesn't hear from an ex, now a friend with benefits.

"Feels good... You've done this before?"

"At least once," he replies as he continues to knead her tits. "Are you protected, Carol?"

"I am indeed."

Carol laughs as he moves his hands to her legs and moves his head between them, inhaling her sweet fragrance. He licks her outer lips, working his way to her essence as sensuously as possible, until her squirming makes it difficult.

She pulls him up to her and gives him a kiss he's never before experienced, then breaks it off.

"Mike, you've made me so horny you have to get your cock inside me now," she demands.

He smiles, kisses her again, then she reaches for his rock hard cock and guides it to her pussy. She's incredibly wet and moans sweetly as it slides in. He has to cover her mouth to keep her pleasuring vocals down to a dull roar.

As he strokes her slowly, she squirms and wiggles, then reaches for his ass to pull him inside her as far as it will go. She also puts the heels of her feet against his ass cheeks to help pull him inside her. They fuck like that as the sensations of pleasure reach deep into his brain. She's a tight fit and the feeling is making his day.

He pulls out, then shoves his cock deep inside her as she rolls her eyes from the pleasure she's feeling. He moans as Carol squeezes his cock with everything she's has and he feels it. It's a surprise for him and it does have the desired affect.

He continues fucking his ex and they are enjoying the pleasure it gives both of them. She's tight and he relishes the time he's spending inside her while she continues to moan her delight as he fucks her pussy with varying degrees of pleasure.

The pressure of her pussy on his cock is creating a delight that's out of this world so his hands begin kneading her tits and pinching her nipples as he fucks her as deeply as possible.

As he picks up the pace, he feels that familiar urge building inside him. Carol is squeezing his cock relentlessly and he finally shoots rope after rope deep inside her and that triggers her orgasm. She shakes and shivers as her orgasm overwhelms her, something no other ex girlfriend has done.

As Carol comes down from her orgasm, he removes his cock and bends over her to give her a kiss. She responds, holding him tight with her legs pinned on her tits. Then she surprises him.

"That was my first ever orgasm by cock, Mike. You're not done yet are you?"

"Nope," he replies and helps flip her to her stomach.

She's laying on the concrete and doesn't complain, but he still gets out of the pool and picks up a towel for her to lay on. He should have done that to begin with. Ooops... He gets it under her and they continue with their strenuous workout routine.

Mike loves fucking from behind. Her tear drop ass and slender body enhance the feel of his cock inside her. Sliding back inside her, she moans again as he tries to muffle her moans with his hand.

Knowing her as little as he does, he's sure it's having a delightful affect on her as well, judging from her moans and squirms. As he begins fucking her, faster this time, she moans non-stop. He has to moan as well because she's so tight.

He caresses her back and shoulders as he fucks her just to heighten her sexual experience and hopefully she will remember from whom it came, but he doesn't stop there. He runs his fingers into the crack of her ass, slowly and tenderly, until he reaches her asshole.

He uses his thumb to pressure it and she moans louder. He has to cover her mouth again, she's so loud. Carol has another orgasm with his cock buried deep inside her pussy and he smiles that he can make her feel so good as he removes his thumb.

He returns to caressing her back and shoulders as he enjoys sex with Carol until she surprises him by having her third orgasm, and it's very intense. It causes his own building orgasm to escape him and fill her pussy with his cream.

After they recover from that orgasm, he pulls out and she slowly gets on her feet, turns to him, puts her arms behind his neck and gives him a very sweet kiss and a very tight hug.

"I love the way you make me feel, Mike. I can get use to this on a daily basis if you like."

"I'm sorry Carol, but there's a couple conditions I will impose if you want to continue having sex with me... First, this will not happen on a daily basis. Second, I don't have any desire to get into a relationship with anyone at this point... I'm not even out of high school yet, then it's off to college. So if you wish to continue, it will be just about getting fucked. Your decision."

He makes it sound as unattractive as he can, hoping she will not accept the conditions, but she does, in spite of his effort. She gives him another sweet kiss and he can't help but pull her body into his as tight as he can. She feels so good to him and her tits are so hot against his chest.

She mounts him and his hands go straight to her ass for some strange and unknown reason.

"Why did you do that?"

"Because when I do, you hold me tight and I love the feel of your hands on my ass. It makes me feel so sexy, even dirty. It's also a quick and easy way to get a man's hands on my ass."

MDSW
MDSW
519 Followers