My Best Friend’s Sister Ch. 01

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Will was a pretty lucky guy. He was super attractive, for one. He was six foot four, 195 pounds of pure muscle. He was in the gym everyday, partly because he loved looking like this, and partly because his girlfriend was a personal trainer. She trained him for free at the gym a few times a week and when they got home, usually a bonus workout or two. Will had pretty long dirty blonde hair that he sometimes enjoyed tying up in a manbun, and a 5 o’clock shadow beard that he painstakingly trimmed and shaped everyday. Will’s girlfriend, Vanessa was great. Obviously she was in great shape and had a tight plump ass that Will loved. He would randomly squeeze or slap it all the time when they were in public together. Her boobs were much smaller than Will would have liked, but he loved her.

Will’s best friend since kindergarten, Dan also lived next to him in their high rise that looked over the wonderful NYC. Will and Dan had scarcely been apart since they were practically babies.

But Will had an extra reason to be particularly happy today. Dan had told him the night before that his little sister Ashley was flying into town to visit him Saturday. This was great news to Will, a little over a year ago now, in a drunken haze Will had professed his attraction to Ashley that he had harbored since high school. To his complete surprise, Ashley had told him she felt the same way. Since that night, Will and Ashley had taken every opportunity they could find to fuck like rabbits every time she came to town. It had been over two months since Will had seen Ashley and he knew they both were eager for this weekend. Ashley was Will’s ideal woman. She was taller than average, about 5’8″, and had platinum blonde hair just a little longer than Will’s, down to her shoulders. She had an enormous, fat ass that jiggled whenever she walked. Will was fond on continually spanking it when they fucked doggy style. She also had enormous DD tits that you could just bury your face into and suffocate. The last time they saw each other, Will had finally gotten up the courage to ask, and Ashley had said yes, he could film her sucking him off. Will had jacked off to it every night since.

Today was Friday, the day before Ashley had told Dan she would arrive but Will knew better. It was the same every time, He would offer to pick up Ashley from JFK, because the two of them were friends too. But Ashley would secretly buy a plane ticket the day before and spend the night at Will’s before he ‘picked her up’ in the morning.

A ding on Will’s phone roused him from daydreaming about Ashley. He picked up his phone and on it was a picture from Ashley herself, laying on his bed. He was glad that he had opted to give her a key last time. He shot back a text that said “I’ll be home at 4:00 gorgeous.” and scampered off to the bathroom.

Huddled in the bathroom stall with visions of Ashley running through his head it only took him a second to get hard. He snapped a few pictures of his cock, and put his phone away. He would need those later.

Back at his desk, Will inspected the photo he had taken. It was an excellent photo, and not for the first time in his life, he thanked his dad, God or anyone who would listen that travesti porno he had been blessed with a dick this big. It was an 11 inch behemoth. He had been told many times throughout his life that he should go into porn with a rod like that. But Will was happy just satisfying the women he chose in private.

At quitting time, Will came out onto the street and, knowing he only had a 10 minute cab ride home, sent off the cock picture he had taken earlier to Ashley with a message that said “I want you naked and on your knees when I get home. 10 minutes.”

When he was in the cab, his phone beeped with a return message just saying “Yes Daddy.” with the smiling emoji with a halo next to it.

Will practically ran upstairs to his apartment, the elevator could not go fast enough. When he got to his door he composed himself, unlocked it and opening the door. Just inside the doorway, in full view of the hallway, was Ashley, completely naked, her beautiful tits cupped in her hands and her nipples already hard, like headlights for the whole floor to see. Before Will could even process what was going on, Ashley reached her hands out and pulled him closer, before unbuttoning his pants and taking out his half hard cock. She gave it one or two strokes before shoving it all in her mouth. Will could feel his cock growing inside her as Ashley bobbed her head up and down working away at his cock. Will sighed deeply, this was a pleasure he hadn’t enjoyed in too long, but with a start he realized, Dan! They were still practically in the hall! He could come outside at any time and catch them!

Without thinking Will picked up Ashley and threw her over his shoulder. He walked her into his spacious bachelor apartment, closing the door behind him, and set her down by the foot of his bed. He had a small box underneath his bed that Ashley knew was where he kept his condoms and sex gadgets. She shivered in anticipation. Will knelt down and picked up the box. Then he put his cock in her face. “Take a good look baby. It’s the last time you’ll see it for a while” he said.

“It’s beautiful Daddy.” she cooed.

Will reached down and put a blindfold over her eyes. Ashley was so excited, she had never been blindfolded before. To tell you the truth, Will was only the second man she had ever been with, except for her old boyfriend Carl. Carl had been a missionary sex for two minutes then smoke a cigarette kind of guy. “Open your mouth.” commanded Will.

Ashley opened her mouth as wide as it would go, knowing that was just barely enough space for Will’s huge cock. He gently inserted his cock. It was wonderful, she had forgotten how much she enjoyed sucking off her brothers best friend. “You ready baby?”

A muffled “mm hmm” was all she could muster.

Ashley removed the hair elastic she had around her wrist and reached up to do her hair in a very tight high ponytail, to give will a good handle to hold onto. When she was done Will told her to put her hands behind her back. She obeyed and after some rummaging through the box she heard a click and felt the cold steel on her wrists that could only come from one thing. Will had handcuffed her. She opened her mouth alt yazılı porno just the tiniest bit wider, and focused on expanding her throat. With the firmness of an experienced Dom, Will grabbed her pony tail and began wildly facefucking her. In and out and in and out, alternating between thrusting into her mouth and using her pony to slam her head up and down his cock. It was exhilarating. She hadn’t felt this rush in forever. She hoped he wouldn’t cum down her throat, all she wanted was that big hard dick inside her pussy.

After a few minutes of this Will stopped. “Hell yes!” she thought, they were going to fuck after all.

Will grabbed her by the neck and turned her around before shoving her face first onto the bed. Her entire top half and her ass was laying on the bed and her legs were dangling off. She could hear him walking a few steps away from her, the kitchen, she knew was over there. She knew exactly what he was doing, there was a huge wooden spoon he had over there. She had bought it for him last Christmas. She had always cooked Will and Dan their favorite pasta dish with her own whenever she came to visit. A secret known only to Will however, was that it also turned her on like nothing else to be spanked with it. “You’ve been a very bad girl” Will said to her as walked back over.

“I’m sorry Daddy, I won’t so it ag-” but she was cut off by a smack on her ass so violent she knew it would bruise.

She squealed in delight. “More Daddy, PLEASE!” she begged.

Will was more than happy to oblige. He wailed on her ass, over and over very hard until her ass was red and would certainly bruise. Will enjoyed the wiggling of her ass when it was hit. When Will was done they were both out of breath. Ashley was as wet as she had ever been, she was sure she had left a wet mark on Will’s sheets where her pussy had been, but she didn’t care.

Will for his part was rock hard and ready to go at her. “You ready for this cock baby?”

“Yes Daddy, give it to me please!” begged Ashley.

Will was happy to oblige. Ashley heard the familiar click sound as the handcuff was removed from her left hand. This disappointed Ashley a bit, she had started to enjoy not being able to move her hands. It felt as if she was being totally dominated. All of a sudden Will flipped her over onto her back. He came over to the side of the bed and helped her inch herself up towards the head of the bed. Then he took her two hands and handcuffed her again, this time through the bed frame so she could truly not go anywhere. Will walked back to the end of the bed and looked at his little submissive slut. “Open your legs.” he ordered.

Ashley’s legs spread at his command, inviting him into the paradise he knew lay between them.

Ashley was enjoying the thrill, she loved being at Will’s mercy, and enjoyed him ordering her what to do. She had her legs spread, chained up onto his bed just waiting for him to take her. Then she heard a third click. But this one was different, it wasn’t a handcuff, it was a Polaroid camera taking a picture. He had just taken a picture of his best friends little sister, butt naked and hogtied to his bed, with üvey baba porno her legs spread inviting him to fuck her. She should have been outraged, but instead, to her surprise, it just made her more wet. “Daniel better not ever find that fucking thing” she thought.

Now that he had his picture, Will was ready to ravage her but he remembered something else. A few weeks ago he had been to his friends apartment, who lived just across the street in an equally tall building. Out of curiosity, Will had looked out the window to see if he could see his own apartment from his buddy’s window. Turns out he could, but he couldn’t quite see the bed. He was willing to bed several apartments above his friends could see his bed however.

With that in mind, Will casually walked over to his big bay windows and drew the curtains. Now all of Manhattan could see in and see just exactly what, and who, he was doing.

It was the moment of truth, Will crawled up on the bed at Ashley’s feet and slowly and as quietly as he could, approached her pussy. He wanted it to be a surprise when it happened. He was over top of her now. He wasn’t going to bother with a condom. He set one of his hands by her chest and leaned down to slightly flick her nipples with his tongue. With the other hand he massaged her clit with the head of his penis, causing a satisfied moan to shudder from Ashley. Then, without warning, he stuck it in. The scream that erupted from Ashley was so carnal and load that Will was sure the whole building could hear it. But at this moment he didn’t care. He was inside her, this was the moment he had been dreaming about for months. He could feel her insides. He slowly inserted his entire cock, all 11 inches until she was down on the base of his cock. This prompted many moans and deep breathes from Ashley, but she seemed to have the volume in check for now.

Will was in heaven. He could feel the walls of Ashley’s pussy expanded around his cock. He started to pump. Slowly at first, but getting stronger and faster. Ashley’s volume didn’t matter anymore, not that she could have controlled it anyway. She was completely out of her breathe, and out of her mind. All she could think about was cock, and Will, and Will’s cock. IT all she had to moan “fuck, harder, harder, harder, don’t stop, go deeper, yessss please!”

Will’s favorites were the “Thank you Daddy, yess Daddy”.

Finally, it was over, Will had to come, no matter how much Ashley begged him to keep going. He pulled out “I want you sweet sweet cum Daddy” Ashley breathed.

“Open your mouth baby.”

And she did she opened as wide as she could and stuck out her tongue, eagerly awaiting her reward. Will’s first stream hit her right in the face, some went on her mask that she had somehow forgot she was wearing, she usually blacks out when Will’s fucking her anyways, and some went in her mouth. “Thank you Daddy” she purred.

But Will wasn’t done. More streams were coming 2 or 3 lander on her titties and a lot pooled on her perfectly flat stomach. Finally, after 7 or 8 jets, Will was done. He got up and stood in front of her. click another Polaroid. Ashley was too worn out to talk, all she could do was lay there. Will stood there for a moment, admiring her. “I probably should undo her so she can clean up” he thought.

But he figured it was more fun to leave her there for a few moments. She was his fuck toy after all, he could do what he wanted to her. Smiling to himself, Will walked to the bathroom to clean himself up.

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