Best Friend's Son

Jennifer and Melissa had been friends for years, though they had not seen each other in almost four years for various reasons. Mainly, Melissa was dating a jerk that Jennifer couldn't stand. One day though, Jennifer passed a house and noticed that her old friend's car was out front. After a drive around the block, she decided to take a leap and see if that was her house. She parked and went to the door and knocked.

"Hooker, what the fuck are you doing here?"

"Good to see you too." Laughing, they hugged each other for a moment.

"Come in, come in."

Jennifer walks in and looks around at the new house Melissa is living in. Plants and seashells everywhere, some things never change. That thought though, was quickly rejected. Some things and people had changed.

Coming out of one of the back rooms was Chad, Melissa's son, that Jennifer had had a crush on since he was seventeen. He was not a young naïve seventeen year old anymore though, Chad had become a man evidently. His piecing blue eyes still looked immediately into your soul, but the face now had ruggedness to it. There was a new gleam in those familiar eyes as well, something she had not seen before, but her body knew immediately the meaning and reacted accordingly. Jennifer could feel her breath quicken, heart race and even her nipples tightened up to this man standing before her.

"Hey Jenn, how have you been, been a long time." He comes forward and surprises her by pulling her close, pressing her body tightly against his rigid one. He kisses her cheek and whispers that it has been far too long. Emphasis put on the last two words as he pressed his nether region harder against her.

Jennifer is pulled from her daze by Melissa clearing her throat. Absolutely mortified by her body's response to his new found confidence and demeanor, Jennifer just sat down and tried to take her mind off of the man sitting next to her on the couch. His warmth did nothing to cool her body and she found it hard to concentrate on what her old friend was saying.

Not long after she arrived, there were passing a joint around and talking like there hadn't been four years in between meetings. She looked over at Chad for a moment to grab the roach and their eyes locked. Not looking, Jennifer was burned on her finger and with a yelp she pulled her hand back.

Chad picked up the dropped bud and then grabbed her hand and put her finger in his mouth. Once he started to suck, Jennifer flooded her panties. Jerking her hand away when she heard the steps of his mother coming back from the bathroom, she turned straight in the couch once more and tried not to look so damn guilty.

Chad couldn't believe Jennifer just popped up after all these years, but damn was he happy to see her. He had regrets of not hitting it before, he vowed to not let an opportunity pass again. She hadn't change much in those few years, hair was a bit longer, well past her waist now. She must have been about 28-29 years old now, five years older than him, but he liked older women. Maybe that was because of her and the crush he had had on his mother's best friend for many years. He had spent many nights wanking to her round plump ass and jiggling big tits.

Going back on to the porch, he had to chuckle to himself. Those two were back in the garden again, laughing about who knows what and weeding the flower bed. His member stiffened when he saw her bending over to pull weeds, imagining his hands on either side of her hips, drilling her till he heard her scream like that one night. The night he will never forget.

The night him and Melissa and his sister had stayed over at Jeni's because they had to bomb their house after buying something used and infested. He remembers waking up to the most erotic sounds of pleasure coming from her bedroom and he couldn't stop himself from creeping over and peering in to the 6 inch slit in the door.

Jennifer was doggy style facing away from the door, her boyfriend was nose deep in her pussy, slurping to her melody of moans. After she had a few more obvious orgasms from which she had squirted both times, her boyfriend Jason sat on the bed and pulled her on top of him to straddle his long thin cock. Her hands were quickly stuffing his meat inside of her and her moan got lower and more drawn out.

Chad couldn't believe what he was seeing, couldn't believe the way her ass jiggled every time she slammed down into his pelvic. After a time, she turned around to ride him reverse and inadvertently gave Chad a full frontal view of her body. Flat stomach, long lean legs and large tits bouncing with each thrust. Jason had her hair wrapped around his hand, tugging her towards him to suck on her neck.

Chad was so close to pulling his dick out that he had to rub himself to relieve his ache some. Opening her eyes, she looked right at him. She didn't miss a beat, maybe even picked it up some. Jennifer started riding the cock harder as well as faster, pushing Jason and herself to orgasm moments after she saw Chad. She was looking in Chad's eyes as she came for the eighth and final time, her juices visible from his place by the door. Chad backed up quickly before Jason seen him, he was so horny he had to go the bathroom immediately. As soon as he was safely behind the door, Chad whips his prick out and started to wank furiously, thinking about what he had just witnessed.

It had been five years time, yet he still remembers it like it was yesterday. She has been his greatest inspiration for all these years. He was determined to have her, this go-round, before she disappears again for another three or four years.

"Chad, you wanted to come with us to Beech Head?"

Startled out of his memories, he looked up to see Jennifer looking at him kind of weird. He couldn't help but look her up and down before he just nodded his agreement and quickly walked off trying to hide his raging hard on. He walked into his room quickly and starting masturbating vigorously. In moments he was spent and changed, walking out of his room a bit more pulled together.

Jennifer could see Chad's woody when he raced inside so quickly. The way he acted, relaxed and happy, she knew what he had done in his room just now. Watching him pull his shirt on as his walked back in the living room, she couldn't help but appreciate his hard lines and broad shoulders. He was skinnier than she preferred, however there had always been something about him.

Taking Melissa's boyfriend and a few other friends, they all pile in to a van, Jennifer is somehow in the far back, next to Chad. As Justin takes off, Jennifer can feel his leg against her bare one. She was wearing a bikini with a thin cover dress with heavy side slits that bared most of her legs to her hips. Her auburn hair was down and flowing with a natural wave. She had purposely undid a few buttons on the top to show some, but not all of her cleavage.

The sun was starting to dip in the sky and there were long overcast shadow in the van. Everyone seemed to be talking at once, so Jennifer just looked out the window at the countryside rolling by. After a few moments, she felt a hand on her thigh. Just barely there at first and then more firm. His hand slowly moved up her thigh through her slit until he reached her hips and the ending of it. On top of the dress he continued up her side and then settled across her chest, palm cupping her ample breasts through the thin cotton blue fabric.

Afraid to look at him and stop his hands, Jennifer continues to look out the window. She can feel his hands splaying against her stomach, shoulders, legs and just for a second over her heat. She squirmed with the attention, although she was well aware of the other people that were so close by in the other seats. That may have turned her on even more, because before long, she was quite wet.

One of Chad's hands had found the slit on her thigh once more and slowly approached her panties. Unable to not react, she took a sharp intake of breath that gained her looks from the two sitting in front of her. Blushing furiously in the dark, she couldn't help but notice that his fingers were weaseling their way underneath her bikini bottoms. His thick fingers found her slit quickly and soon she was jerking as it ran across her clit. Rubbing her button, his other hand snaked down her dress front to cup her breast, gently pinch the already hardened nipple. Burying her face into his chest, she released on his hand. That was one of the best orgasms that Jennifer had had in years and she tried her best to muffle her cries into his hard chest. His hand did not stop for several minutes, dragging the orgasm out for what felt like hours to her.

Chad could not believe what just happened. He could not believe that he had his hand on her pussy and titties, but there he was with all her pussy juice on his fingers. He pulled his hands back and licked his fingers clean. He reached over and grabbed her hand and brought it to his crotch. Rubbing her hand roughly against his shorts, to let her feel how turned on he was by the taste.

Before he could get an idea to pull his hard penis out, the van was pulling in at the beach and the harsh lights were coming on to expose their misdeeds. Straightening up quickly, they follow everyone else out of the car. Everyone started collected firewood and rocks for the pit and soon a huge fire was blazing, heating up the chilled night air. After passing around the bong for a while and drinking a few beers, everyone seemed to be chilling out. Some were getting into the water and he noticed Jennifer was looking down the water line.

"Jenn, you want to take a stroll down the beach with me?"

Jennifer knew how loaded the question was and what her consent would really mean. She nodded her head and got up from the drift wood bench to follow him off into the darkness.

They were not even out of earshot before Chad had pulled Jennifer down into the sand, dominating her with his body. He caught her lips in his for a sweet kiss that was the direct opposite of his aggressive body pressing and grabbing her. He pushed up her dress quickly and with little finesse. He was becoming too excited and he thought he may burst before he could even penetrate her.

Forcing himself to slow down, he moves lower on her, pulling her bottoms down and off. Spreading her legs wide, he starts to nibble and suck on her nub. She was squirming and crying out to his delight, just like he had remembered. The taste was exquisite, and the flood of fluid told him that she had came again. Sucking harder, he slipped a finger inside of her sopping wet pussy. Her squeal made his dick lurch painfully. He increased the tempo, finger fucking her while he had his fill of her pussy.

After she climaxed again and had almost a dazed look in her eyes, Chad detached to stand up and pull his clothes off. Jennifer was still panting, laying there with her eyes closed and her legs spread wide open. Chad positioned himself between her legs and pressed in.

Jennifer's eyes popped open and a scream escaped her mouth before it could be stifled by his hand. He entered so swiftly that it caught Jennifer off guard, his size was another. She never got to see it, but it felt impossibly long and thick. Not given a chance to adjust to his larger size, he started to pound into her, while he kept the hand over her mouth.

Chad increased his pace as soon as his cock was surrounded by wet folds. Once inside, he could not hold back any longer. He slammed into her over and over again, replacing his hand with his mouth and another lingering kiss. He looked down at her as he pulled her legs over his shoulders to go even deeper inside. He could feel her melting against him, around him, her juices were all over him. Unable to hold back any longer, it was over. With a low growl, he blasted inside of her.

Chad got up quickly, a bit mad at himself. He got dressed in a flash and looked back to see Jennifer in the sand appearing to be passed out. She did not even move, but her chest gulped up lung-fulls of air. He smiled a bit to himself, no longer upset in his pre ejaculation, he doubts she could have handled much more. There was something to be felt when you lay out an older woman as fine as she was. He almost went back to her, but he knew that was not what she wanted.

Jennifer had always made it clear that she wanted what a man could physically offer her, then she appreciated him to leave. No cuddling, no soft words, just go. He remembers her saying that and he always wondered if that was true. The fact that she did not say anything as he turned and walked away, made him think that was what she really wanted.

Many months went by and a trip was planned to the Florida Keys, Chad was invited, as well as his mother. Chad was excited to go, he hadn't seen Jennifer much, and he had talked to her even less. Fucking her had been better than watching and now he thought about her even more. He immediately got hard every time he saw her or even heard her voice. He had answered his mom's phone and just a hello and a giggle had made him rock hard. He had to hand the phone off and had to almost run to his room his need was so great.

It had been hard not to grab her up and slam his swollen appendage into her. Every time she came over to visit and they were in a room together alone, he tried to muster up some courage. But as soon as her eyes locked with his, he was unable to say a word. She would look at him with those big green eyes and he was lost, every time. The thought of being around her for the next 2 weeks, would be either torture, or heaven and he was eager to see which way this was going to go.

Jennifer on the other hand, was nothing but excited for the trip and the possibility with another chance at that dick. She found herself shy around him nowadays, never knowing the type of pleasure he could bring her. He did not seem to want to do it again, although he did have lust in his eyes when he looked at her lately. The way he just took off after the best sex of her life though, made her somehow question her abilities. Something that she never really had a chance to show him, as he just took her before. Maybe that is what the problem was, she had not been taken in a long time, and certainly not by a 25 year old.

The day arrived quickly and she picked them up with a mountain of stuff and started off riding low in the van. Mellissa and boyfriend were in the front driving, while Chad and Jennifer rode in the second row of seats. This ride was different though. Jennifer basically ignored Chad and he became a bit sullen. His maturity was coming out and he was trying desperately not to embarrass himself. He was getting hard and his balls were already hurting. This may be the longest trip ever.

They drove most of the day, ending up in Jacksonville, Fl. The ride was not so bad, they lightly bantered, with little to no sexual innuendos. Chad wore a hard on the whole time, but he did a good job of hiding it from her and the rest. Twice he had to relieve himself at the rest areas on the way, always getting hell for taking so long. But the relief was short lived and he was hard before a mile had passed.

The motel situation was the best part of the day, one room, two beds and a pull out couch. Chad being the gentlemen that he is, offered to take the couch. That night, he slept only a few minutes, the idea that she was so close drove him crazy. Around midnight or so, when everything was quiet, he saw her rise up from the bed and shed her summer dress that she was sleeping in.

Chad had to work hard not to be heard as he saw that she was wearing nothing underneath, her massive globes and shaved pussy were inches in front of him. Jennifer laid back down and covered her glorious body with a sheet. Chad sat up for hours afterwards, listening to her breathe and wishing she would send him a sign. Anything to tell him that he could once again bury himself in her hot sweet hole.

Jennifer slept good the first night in the hotel, Chad was close and as soon as her friend was out for a while, she planned on taking the opportunity to take a little initiative. Her dreams were filled with naughty thoughts of Chad. She woke up with everyone up around her and she was naked and uncomfortable wet. Grabbing her dress, she slipped it back on under the covers. She could feel eyes burning into her, her face turning red as a boob flops out. She looks up to see Chad looking at her, the same smoldering look in his eyes as before. Getting out of bed finally, Jennifer nearly sprints into the bathroom, to take a quick shower. She planned to cum and then wash it off with the pre-cum that was starting to slowly drip down her inner thigh.

The shower was quick, the orgasm was not. Trying to stifle her moans was the hardest part and knowing that there was three people a few feet away helped push her along quite rapidly. She left the bathroom refreshed and ready to start the day. The van ride down was a bit different, the sun was shining through the windows and they both decided to move to the back row with the bench seat. The curves and sudden stops from Melissa's erratic driving, sent the two into each other several times. When it was clear that no one was looking at the couple in the back, Jennifer took advantage of one of those famous turns.

Banging against Chad, Jennifer put her hand out and grabbed hold of his hard-on. "Oh, sorry. "

She couldn't help but smile when she heard his strangled moan. It became longer and more prolonged as she started stroking him through his jeans, instead of continuing the charade as if it were an accident. She quickly pulled out his long length and for the first time, she got to see what had caused her so much pleasure before. She also seen the difference, he was uncut and this was her first time. Jerking his foreskin back, she stuck it all in her mouth till she started to gag.

Chad grabbed her head, but his hands were quickly grabbed and held down to his sides. She was making clear who was the aggressor this time and he gladly laid back to enjoy. She bobbed on his head quickly and deep. Chad had to concentrate on controlling himself, he was ready to explode and scream. Jennifer gave him no mercy. One hand left his, to cover his mouth and the little whimpers that was emanating from him. Her other hand, encircles his shaft and mimics the movement of her mouth. She was unable to fit such massive dick down her throat, so the base was feeling neglected.

He almost came twice, but she would pull him out of her mouth until the feeling subsided. She was driving him crazy with each stroke, his body was tensed up and ready to shoot. The hand on his mouth went to his balls and started caressing his tender jewels. Unable to hold back and the apparent permission to cum, he shot a load deep down her throat. Jennifer swallowed it all up and then stuffed his now semi-soft cock into his pants. Wiping the drip off her chin, she moves back up to the second row of seats. She laid her head down and closed her eyes.

Chad unable to move, stares at the back of her head as she dozes off to sleep. He felt drained but energized by her actions. It was not to be the last time he laid with her and now his thoughts were filled of her curves, mouth and silken folds. He adjusted his piece in his pants and laid back with his eyes closed and his mind racing.

Jennifer woke up a few hours later, refreshed and with a bit of cotton mouth. She turns her head to the right, to see Chad sleeping next to her in the chair, facing her, his body curled towards her. She studied his face for a minute, the young face with the five o clock shadow. She had to stop herself from reaching out and touching the stubble, to feel it under her fingers. Her feelings for him were more tender than she was used to and she regretted being taken the first time. She lost her control and it was driving her crazy. That he could take her at all, drove her hot at night when she replayed the moments.