Right or Left?

Story Info
A brother and sister start an intimate relationship.
4.6k words
4.58
160.5k
254

Part 1 of the 8 part series

Updated 06/08/2023
Created 08/21/2017
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Wendy stared at her iphone trying to decide...should she swipe left or right?

Her brother Jeff said that he loved this phone app and he had "met" all kinds of women on it. He had downloaded the app on her phone and she decided today to give it a try.

He said it was very simple to use and he was right; you looked at a photo and if you were interested in the person you swiped to the right to set up a meet or if you weren't you swiped to the left to ignore or reject them.

After looking at and rejecting tons of photos of men she was stopped at the current photo. She had viewed so many photos of men in her area and this was the first one that caught her eye and stirred her juices.

It was a picture of her brother!

Wendy looked around the coffee shop to see if anyone was watching her, she felt vulnerable to the world like everyone could read her dirty thoughts or notice her blushed cheeks as she looked at Jeff's photo.

When her hands started to shake she knew she was in trouble. Could she really be thinking of doing this? Swiping to the right for her own brother?

She looked at his handsome picture again and she could feel her panties getting wet. He has such a manly look and his chiseled features accented the dimples in his cheeks. He was very popular with the girls and even her girlfriends were giddy around him.

Setting the phone down on the table she sipped her Chai latte, as she tried to calm her nerves. His image starred up at her with that mischievous grin on his face. She could almost hear his deep voice and infectious laugh.

Her cheeks flushed as she remembered what had happened last Friday night, she never dreamed something like that could every happen to her; and it was all because her brother had come home early and found her like he did.

**************************************************************

Wendy was excited at the thought of having the house to herself on a Friday night. Her parents had told her they would be away visiting relatives for the weekend and her brother Jeff said he was going out with his friends to have a few beers at the local pub. He told her he was going to be very late and not to wait up for him.

Sex for Wendy was a big thing, once she discovered how good it made her body feel she craved it, needed it. She had broken up with her boyfriend a couple of months ago and in all that time the only sexual relief she enjoyed was from her trusty purple friend.

She loved her purple dildo and the tickler attached to it. Many a night she would fuck herself with it. She loved to go slow when she had a lot of time and when she didn't she would turn her hand into a piston and fuck herself as fast and hard as possible until her orgasm exploded. Sometimes she would fall asleep with it in her not wanting to let go.

Wendy had prepared everything she needed for her night of pleasure. A glass of wine was on the night table, she had the background music on softly, the lights were turned down low, but not too low and her purple dildo waited for her on the top of the bed. She looked at the clock and was thrilled to see she had lots of time to have her fun. It would be several hours before Jeff would be home, and a hot shower was just what she needed to start the night.

The shower was both relaxing and stimulating and Wendy payed special attention to her pussy and ass cleaning both holes inside and out. As she stepped out and dried herself off she rubbed the mirror clean of the steam and admired her young body. She liked what she saw and smiled at her reflection in the mirror. Her slender body and flat stomach, her firm perky breasts, her shoulder length blonde hair, her blue eyes. She tossed the towel on the floor and it landed on the enema bag which she had used earlier.

As she stood there admiring her reflection it still amazed her that her boyfriend had cheated on her; once again proving she had terrible taste in men, but it was his loss not hers.

Wendy rubbed skin cream all over her body then walked naked from the bathroom into her adjoining bedroom. She smelled good, looked good and soon she knew she would feel good. Real good!

She took a sip of the white wine from her favorite local winery, a nice Riesling, taking one more sip before setting it back down. Memories surged through her mind as she looked at her bed and the spring flowery duvet cover. It reminded her of the meadow where she had lost her virginity two summers ago, the start of her sexual journey.

Laughing out loud she jumped to get on the bed wondering once again what had possessed her to buy a bed so high when she was only five feet tall. The purple dildo bounced in the air like he was excited to get started too. Her purple friend was always waiting for her, non-judgmental, ready to do whatever she wanted with him and to him. She knew it was silly but she liked to think of it as a him.

One more glance at the clock confirmed there would be no rush tonight, she had hours to please herself, over and over again if she wanted to.

Her girly bedroom showcased all her childhood memories on the walls and shelves. Sports trophies, medals and family pictures everywhere. Her favorite one was of her and Jeff at the beach; him in his Hawaiian boarder shorts and her in a new bright red bikini. He was so much taller than her, his arm hung loose over her shoulder, his hand almost touching her breast. Her mom had complained that the bikini was much too small to wear in public but Jeff had stood up for her saying she was 18 and a woman now. She loved the attention Jeff gave her that day even if he was her brother.

She fluffed up one of her pillows and moved it towards the middle of her bed. Just thinking of what was to come was making her pussy wet. She took one more sip of wine and then stretched out on top of the covers with the pillow under her ass.

Her fingers started with both breasts, she loved to have her nipples pulled and twisted, the pain seemed to add to her pleasure. She closed her eyes and imagined a handsome man was making love to her. He was tall, dark haired and had a hard body. She could feel his hands on her breasts, teasing her, making her moan out. Wendy loved to talk dirty to her lovers and being alone tonight she decided to talk out loud to her imaginary lover, guide him to do all kinds of nasty things to her.

"Oh that feels so good babe, pinch my nipples just like that." Wendy whispered to her imaginary lover. "Pull them and twist them, hmm."

In her mind she could feel "his" hands on her breasts. She felt "him" slide his hands down her body, as he rubbed her tummy then sliding between her legs. She was moist already the anticipation building inside her when "he" touched her there.

"Please, finger my pussy, I need it so bad!"

Wendy ran the fingers of her right hand over her bare mound, as she enjoyed the tingling deep inside her. Her fingers running from the opening of her ass back to her pussy, her palm rubbing on her clit. She loved all kinds of sex including anal.

"Yes, that feels good!" Wendy said. "Stick your finger in me!"

Soon her fingers were sawing in an out, her juices running down onto the pillow.

"Please babe fuck me, stick your big cock in my pussy!"

It was time for her purple friend. She looked around and found him by her side, a quick suck and he was ready. When the tip split her lips and entered her she felt the tickler on her clit. The sensation brought out moans, deep from her belly. She loved a real cock but this was a good second choice. Soon her hand was forcing it deep, going in and out of her tight hole with a slow deliberate stroke.

"OH FUCK! YES! THAT FEELS INCREDIBLE!" Wendy yelled. "DON'T FUCKING STOP!"

**************************************************************

Jeff had no intention of returning home early but when the bar girl "accidentally" spilled a sticky drink down his shirt he came home for a quick change. He was sure she was pissed at him for not returning any of her calls, while she had been fun in bed he found her a little too vanilla. He liked his women to have spirit and enthusiasm. Looks like he might have to find a new favorite bar.

As he entered his house he heard Wendy's voice and it sounded like she was screaming. With concern running through his veins he ran up the stairs to see if she was alright, prepared to fight off any intruder who may have broken into the house. His adrenaline surged through his body as he threw open his sister's bedroom door expecting the worst. He halted in the open doorway, frozen, unable to say a word.

Like a deer mesmerized in headlights he stared at his naked sister lying all alone on the top of her bed. There was a big pillow under her ass, her legs were splayed wide, knees bent and she had a dildo in her hand going in and out of her pussy. He could see she had her head thrown back, eyes closed, her blonde hair cascaded around her pretty face. Her mouth was open and she moaned every time she pushed the dildo into her pussy. Wendy was so into her self-pleasure she never heard the door open or realize her brother was now in her bedroom watching her every move.

Jeff's first thoughts were to quickly leave before Wendy saw him but he was frozen in place. He knew it was wrong but he couldn't help himself, he felt himself being drawn towards his sister. Against his better judgement he quietly closed the door and turned to see if Wendy had noticed his presence.

His little sister's hips were lifting up and down on the pillow like she was riding a bucking bronc. She filled the room with her moans as she fucked herself.

Once more he made a quick decision, he took his cell phone out of his shirt pocket and set it to video. From past experience he knew the eye of the camera was just above the top of his shirt pocket and more than once he used it to make a private recording, but nothing like this.

All of a sudden Wendy screamed out. "YES, fuck my cunt, oh yeah just like that, nice and deep! Oh baby you're so hard just the way I like it!" Wendy moaned. "Don't stop, don't ever FUCKING STOP!"

Jeff was so startled when she screamed out he almost fell over. He was sure she had heard his feet on the carpet but thankfully his sister kept her eyes closed. Jeff thought back to all the women he has been with and Wendy looked better than all of them. So sexy, so fucking sexy as she fucked herself. He stepped closer to get a better view.

Wendy's pussy was shaved bare and he could see every fold, even her hard clit was in plain view. Her big tits looked so suckable and her nipples protruded hard and proud.

Jeff quietly moved forward until he was right at the end of the bed. He watched his sister's young tits, firm and full, as they rose with her labored breathing. He stifled his own moan when she started to pinch her nipple with her free hand. With her legs pulled back her wide open pussy was pointed right at him.

Once more Wendy startled Jeff as she screamed out. "You like that don't you? You like fucking my tight little pussy with your nasty big cock. Let me taste you, I want to suck your cock with all my juices on it. Fuck my mouth."

Jeff watched Wendy as she pulled the purple cock out of her pussy with a sloppy pop and bring it to her mouth. Her tongue snaked around the tip then she slowly swallowed it, all of it. Jeff was amazed she could take it all in, he didn't know how long it was but it had to be at least 8 inches. Wendy continued to deep throat the purple cock, he could see her cheeks sink in with a purpose as she sucked hard. Wendy definitely knew how to suck a cock and even though he knew it was wrong Jeff wished it was his cock she was sucking.

With the dildo out of her pussy he was drawn back to her wet slit. He could see right inside her as she was still open from her fucking. Her clit standing at attention and the desire to suck on it was overwhelming. Her pussy lips glistened in the soft light from the table lamp. He silently hoped there was enough light in the room for the video he was making.

Once more Jeff jumped when Wendy started to talk dirty. "Did you like that baby? Did you like fucking my mouth? I have a surprize for you sweetie, tonight I am going to let you fuck my ass. I know you want to put your hard cock in my tight little ass. Go slow baby, don't hurt me."

Jeff couldn't believe it when Wendy reached down to her pussy and gathered juices on her fingers and rubbed them around her tight brown star. Back and forth she went from her pussy to her ass until she could push a finger in. Jeff checked and his sister's eyes were still closed and her head was thrown back. Wendy was fucking her imaginary lover but never in a million years would she have dreamed her brother was at the foot of her bed watching her every move.

It didn't take Wendy long to loosen up and soon she had two fingers in her ass sliding in and out. Jeff swallowed hard as his sister pushed the purple dildo in her tight ass. There wasn't much resistance and she pushed half the length in with one thrust.

"Oh fuck, oh fuck, that feels so good! Fuck my ass with your hard cock!" Wendy screamed. "I need it bad baby, don't be gentle, give it to me!"

The purple shaft was all the way in his sister's ass now and she fucked herself with a fury. He could see and hear her hand slap against her ass cheeks each time she reached bottom. Wendy's ass was off the pillow now, her feet firmly planted on the bed as her other arm supported her levitating body. Jeff noticed her screams were more primal now, not actual sentences, somewhere in between.

"I need more lube babe it's getting too tight." Wendy said suddenly. "Let me suck you again."

Jeff was in awe as his sister pulled the dildo out of her ass and brought it back to her mouth. She never hesitated for a second as she put it in her mouth, licking it and sucking it to make it slippery again. After only a few minutes she had it back in her ass and she continued to fuck herself.

"Oh yeah that's much better!" Wendy shouted. "Give it to me baby, fuck my little tight ass and come inside me!"

Jeff's cock was bursting at the seams and even though he knew it was wrong he freed it from his pants and started to jack off as he viewed the unbelievable scene in front of him. He didn't care anymore if Wendy saw him, in fact he hoped she would.

Wendy's hand was a blur now as she fucked her own ass. He watched as she reached down with her other hand and started to rub her clit and finger her slit. Her palm pressed hard against her fleshy girl parts as she rubbed herself.

"Soon baby, really soon, I'm almost there!" Wendy exclaimed.

Jeff knew nothing or anyone could drag him away from the end of the bed at that moment, he needed to see his sister finish. His cock had never been this hard before and as he continued to watch his sister he stroked his cock, imagining it was in her ass. He could feel it pulse in his hand and knew he was going to come soon too.

Jeff matched his strokes to hers and they each got closer and closer to coming. Whether it was just luck or not they both climaxed at the same time.

Wendy let out a scream as she climaxed and so did Jeff, his cum shooting high in the air and landing on her outstretched leg. Jeff had never come that hard before and he had definitely never shot cum out so far.

It took Wendy a moment to realize she had heard a man's voice moaning along with hers. When she opened her eyes she stared into her brother's eyes. He was right in front of her with his cock in his hand, cum still leaking out of the end. Her first thought was this must be a dream or something. She closed her eyes, took a breath, then opened them again. That's when she let out a scream as she scrambled to cover herself not caring anymore about the purple dildo sticking out of her ass.

"WHAT THE FUCK JEFF! DID YOU JUST JERK OFF IN MY ROOM? IS THAT YOUR CUM ON MY LEG?

Jeff didn't know what to say, this had been the most erotic thing that had ever happened to him. Even if it was his younger sister! He continued to look at her but now in a way that he never thought was possible. His sister was fucking hot!

Wendy curled up in a ball against the headboard as she looked at Jeff, trying to hide her body from him. She knew it was stupid as he had just witnessed her completely exposed but still she felt embarrassed.

"Will you stop jacking off and put your cock away!"

"AND GET OUT OF MY ROOM!"

Jeff put his cock back into his pants and zippered up but he never left the room. Instead he came closer and sat on the edge of his sisters bed. Wendy curled into an even tighter ball if that was possible.

Jeff just sat there sideways on the bed looking deeply into his sister's eyes. She had her breasts covered and her legs were closed and bunched under her, the purple dildo still in her ass. Wendy's face was flushed from her orgasm but also from the fact her brother had just witnessed her most intimate moment of self-pleasure.

"STOP IT! Stop looking at me and get out of my room!" Wendy screamed. "RIGHT NOW!"

Still Jeff didn't say anything, he just stared at his sister. Then he remembered about his cell phone in his shirt pocket, he debated about turning it off but he just let it run.

"Please Jeff," Wendy said in a more pleasant voice, "this is really embarrassing for me."

"I didn't know," said Jeff.

"What?"

"That a woman could be so sexy and beautiful at the same time. Do you trust me Wendy?"

"What?"

"Don't move, just stay where you are."

Wendy flinched as Jeff reached out to her, she expected him to touch her but instead Jeff grabbed onto the purple dildo and gently twisted it in her ass. Then slowly while looking his sister in her eyes he started to fuck her ass with it. Their eyes were locked on each other as the dildo slid in and out.

Wendy gave a soft moan when it came loose. He held it up between them and looked it over. The rubbery surface was covered in juices and it glistened in the light.

"Clean it," he said with a straight face, "just like you did before."

Wendy looked at Jeff and she could see he was serious and he suddenly looked exactly like the imaginary lover she had pictured in her mind.

"And if I don't what are you going to do?"

Jeff continued to just stare and Wendy finally gave in. As she went to reach for it he drew it away.

"No, just your mouth. Come closer and suck it."

"Jeff please, don't make me do this!"

"I know you like to do it, I saw you suck it already." Jeff held it out to his sister again.

Like two magnets attracted to each other Wendy was drawn to her brother. The embarrassment she felt was diminishing as arousal took over. She got on her hands and knees and crawled towards him. She opened her mouth and licked the tip. Her eyes were fixed on her brothers as she lowered her mouth over the false cock. Slowly she bobbed up and down on the dildo never breaking eye contact.

Wendy pulled her mouth off. "Am I doing it right Jeff?" She knew she was teasing her brother but she was pissed that he had sneaked into her room. "Hmm, I love a big hard cock!"

Jeff was having a hard time maintaining his composure. His sister was naked in front of him her tits hanging down and swaying gently as she sucked on the dildo. She still had her eyes focused on him and it looked like she was smirking while she sucked.

The two of them were zoned in on each other. Jeff reached forward and pushed some stray hairs behind her ear. The touch of his fingers on her face made Wendy shiver all the way down to her pussy. As he gently rubbed her cheek she could feel her pulse rise.

He slowly lowered the dildo and Wendy followed it down until it rested right on top of his own cock. Wendy sucked harder imagining she had her brother's cock in her mouth. Her naked ass swayed right and left. He had his hand in her blonde hair, not forcing her but just enjoying the ride. Slowly he traced his fingertips down her spine, enjoying the shivers he saw he caused. He couldn't quite reach her vulnerable areas and without a word spoken between them Wendy shuffled a little to the side. She wanted him to touch her; especially there.

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