Pleasing My Best Friend's Sister Ch. 01

Tyler strolled up to the front door of Jeff’s house, he was late from work as usual and they had already started partying hours ago. He just hoped they weren’t all to sloshed, and that they had left him some beer. He opened his door and made a B-line for the refrigerator. He opened the door and smiled as he reached in grabbing four beers. He stashed three in his sweatshirt pocket and cracked the other one open, taking a large gulp. He surveyed the room for the first time, it was mostly the usual crew. A couple people from work and a couple assorted friends they hade made from school and around town.

“Same bitches as usual Ty, no new pussy tonight homie,” James clapped him on the back as he slightly stumbled up behind Tyler. James was one of his best friends along with Jeff. He had been dating the same girl for almost two years now. So he lived out his sexual escaped through Tyler vicariously.

“It’s all good James, I’m just down fro getting good and fucked up tonight, what’s the bud situation like?”

“The bud situation is, the four foot bongs out in the garage, we’ve got a blunt we’ve been saving for you, and the pipe was going around out by the pool,” James was starting to slur his words as he took another long gulp of what looked to be a screwdriver.

“Sick I’m going to go get tore up off that four footer and then I’ll meet you in the pull house for the blunt, sound good?”

“Fuck yeah, hey while your in the garage would you check on my sister, she was so high earlier she fell out of her chair three times, and she hadn’t even started drinking yet,” James laughed hysterically as he made his way outside and to the side of his girl friend Amber. Tyler finished his first beer, popped open the second one and strode to the garage. The four footer was sitting the in the middle of the garage which was completely devoid of people. Tyler wasn’t surprised, their four footer had a tendency to leave its victims completely toasted. Tyler loaded the bowl full and then started to see a dilemma, there was no way to light it and hit it at the same time. Tyler dropped down in a near by chair and cursed his luck.

“Need some help with that their sexy,” the words were slightly slurred, but the voice was deep and sexy. Tyler spun around and saw James sister Leann walk from the front yard into the garage. His jaw dropped slightly as he stared at his best friends little sister. Leann was always cute but she looked absolutely banging right now. She was no taller then 5’4” and she was in fairly good shape. She had a little extra padding in the hips but her stomach was flat and her ass stuck out just right. She was wearing a red halter top that looked to be fighting for its life to keep her massive breasts from falling out into the night air. She had a tight black skirt on that was contouring perfectly to her legs.

“What fucker, do I have something on my face or what,” she smiled as she stumbled over towards him falling into his lap and staring up into his eyes. It was funny before now he had never really thought about her sexually, they had a very flirty friend kind of a relationship, that led more to shit talking then any relationship. She was 18 only 3 years younger then him, and it was no secret that she was still a virgin. Leann could get ass if she really wanted to but she was still to shy around others and had no confidence in what was a beautiful body. Her ass wiggled around in his lap making his dick grow to about half full.

“Better watch out shorty or you might be sitting a little higher off my lap, if ya get my meaning,” Tyler spoke in a teasing way poking her in the side in a very playful way. He by no means wanted her off his lap but better judgment was his call tonight.

“Nah, I just happen to have a hole to stuff that in, hehe,” she giggled to herself as she reached down and grabbed Tyler’s semi hard cock through his pants. She rubbed it softly through the material of his work pants then she suddenly jumped up and walked over to the bong.

“You going to hit this or sit there staring at your cock?”

Tyler got up letting his fully erect penis fly proudly in front of him as he made his way to the bong. Leann began lighting as Tyler sucked noisily from the big green bong. Tyler closed his eyes like he always did when he smoked when he felt Leann’s hand massaging his cock again He felt his zipper go down and her hand fish inside his pants and boxers to stroke his now rock hard penis. He kept hitting the bong enjoying the idea of getting high and a hand job at the same time. With out warning Lean pulled the stem and let go of his cock at the same time. The smoke rushed into his lungs unexpectedly causing him to almost fall straight over in agony. He coughed furiously, struggling for breath. He finished off his second beer and started on his third as Leann rolled around on the floor laughing. He finally caught his breath and put his dick back in his pants, as Lean stopped laughing.

“Real funny ass hole, how bout I get your pussy all wet, then stop all of a sudden?”

“Who says you didn’t already get my pussy all wet?” she stared him the eyes with the most seductive voice he had ever heard. Her face screamed sexual aggression, Tyler quickly downed what was left of his beer and then stood right in front of Lean.

“What’s that mean then girlie?”

“I’m pretty sure it means I want you to fuck m…” as she finished the sentence James burst in the door with his girl friend at his side. Tyler and Leann quickly separated each looking like they had been caught with their hand in the cookie jar.

“Hey bitches, we gonna fire this blunt up or what? Cliff’s waiting out by the pool for us, were going to hot box the pool house.” James was hammered and it showed. He beckoned for them to follow and then grabbed his girlfriend up and made his way to the pool. Tyler looked at Leann and she simply mouthed the word “Later” and then grabbed his hand as they walked out to the pool.

They stooped holding hands as they got to the pool. Jeff’s house was amazing and the pool area was no different. His pool house was like a small one room apartment complete with frig, stereo, and a massive bed that took up most of the room. James and his girl sat on one end of the bed, with Cliff, Jeff, and Jeff’s girl Jessica. Cliff sparked the blunt and it slowly made its way around the room. Tyler and Leann sat near each other at the foot of the bed in a pair of bean bags. The blunt rolled by a good five times before the rest of the crew began making their way outside in to the night sky. Most of them completely forgot about Tyler and Leann laying at the end of the bed.

As soon as the last person left Tyler made his move taking his hand and gently rubbing her ample breasts. His hand moved delicately upward, until it slipped inside her halter top. He worked his hand around her bare breasts inside her top until she finally just ripped the top off letting her beautiful tits to fall forward into Tyler’s waiting hands. He pulled Lean on top of him and buried his face in the beautiful orbs in front of him. Her nipples were small and bright pink, a beautiful contrast to her milky white skin. The nipples hardened under his tongue work, he felt Leann slowly grind her crotch all over his cock. He pulled her in close kissing her, letting their tongue play freely in each others mouth. With a power one would expect from his 6’ frame he rolled over on top of Leann and began sucking gently on her neck.

He ever so slowly made his way down her neck to her chest. He let his tongue caress over each nipple before making his way to her belly button. He licked seductively around her belly button before making a line down to her skirt. Leann tried to rip the skirt off but Tyler forced her hands to her side. He licked all around her stomach and just above wear the skirt sat, she groaned and whimpered as he toyed with her.

“What’s a matter baby, do you want something?” Tyler asked teasingly taking a nipple into his mouth again and then backing off.

“Tyler if you don’t get down here and eat my pussy I swear to God I’ll kill you!”

“O, well in that case…..fuck you,” Tyler hoped up and headed for the door. Leann started to scream for him when he turned around and dived down pulling her skirt up and moving her bright pink thong aside to show her sex. The soft thick outer lips were gorgeous, he leaned in kissing the puffy lips, just barely letting his tongue inside of her.

Leann wiggled and let out a sigh of ecstasy as she finally had a man who was taking care of her needs. Tyler began working her pussy, driving his tongue inside of her and then pulling his tongue out to lick her outer lips. He took one finger and slowly probed her hole that was now thick with moisture. He inserted one finger and then leaned down taking her now hardening clit into his mouth. Lean let out a fully body moan and convulsed slightly as her first orgasm took her. Tyler began finger fucking her with rapid long strokes as his tongue assaulted her clit. Meanwhile his right hand took a firm hold on her left nipple.

“Tyler…please fuck me, I’ve waited so long for you to fuck me. Please do it now I need you inside me,” Leann panted heavily as Tyler continued to finger her extremely tight pussy. He pulled his finger only to replace it with two fingers. He continued this for a while, bringing Lean to another orgasm. Finally she felt loose enough, he stood up and she took the hint jumping up to relieve him of his pants and boxers. He started to kneel down into position to take her missionary style when she stopped him.

“Wait a second, if were going to do this lets do it right,” with that she grabbed the base of Tyler’s cock and wrapped her two full lips firmly around his cock. She worked the cock steadily, taking nearly half of its seven inches into her mouth. Tyler was loving the oral attention since he got it so infrequently. He was enjoying a bit to much and he let Leann know by putting his hand on her head and slowing her down. She looked up into his eyes, as she once again went down on his cock. Right then he knew he was in for something special, no girl had ever looked him in the eyes like that during a blow job. She was into pleasing him just as much as he wanted to please her.

“Leann, babe, you need to stop for real or I’m not going to be able to keep going,” Tyler spoke softly, trying desperately to maintain his concentration.

She pulled herself off his dick and looked him in the eyes again. “Bullshit, I know we can get it hard again with a little help, besides Amber told me how your fantasy was to get a girl to swallow,”

“What the hell were you talking to Amber about me for?”

“Because I told Amber my Fantasy was to have you,” with that she went back down trying to take the cock all the way down her throat. She made it almost, never taking her eyes from his as she gagged painfully on the intruder in her throat. That was it, with his cock buried in her throat, and the revelation that she wanted him that bad he couldn’t hold on any more. He had waited years for a girl to actually take his load, and now the wait was over. His cock pumped stream after stream of cum into her mouth, so much that she couldn’t get it all down her throat. Small streams crept out the side of her mouth leaking onto her breasts. She sucked on the very tip cleaning up his mess like she was an old pro.

Tyler tried to talk but all that came out was gibberish as he lay back onto the bed. Leann climbed up on top of him resting her gushing pussy onto his cock. She gyrated on top of him ever so slowly re-awakening his now limp cock.

“Your welcome Ty, I’m glad you liked it, as soon as your ready, hopefully we can try some other things you like.” She continued her gyrations swinging her body all around, bringing Tyler almost back to full mast.

“Not so fast kid, I have unfinished business,” his hands wrapped around her waist and he lifted her on to his face, enjoying the aroma as he went back to work on her box while his cock regrouped for action…..

The second part coming soon….