A Familiar Affair Pt. 05

All characters in this story are 18 years of age or older.

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The Date Night Continued

The living room suddenly felt much bigger with Beatrice gone as Jessie's hungry eyes continued to observe Grace from a distance; he now felt that name was properly given to her; that blonde teen beauty definitely looked like a gift from God.

Grace had this perfect, long blonde hair that reached down to her waist, beautiful blue eyes that matched the colour of the ocean, her pink lips had the most torturous of sexual appearance, her face was near perfection.

As she left the living room, his gaze followed her. She had this exquisitely shaped, athletic thin frame with a perfectly shaped ass, hugged tightly, and it had a slight jiggle to it when she walked. Her long hair swayed slightly as she proceeded to the kitchen with a very feminine walk. The middle-aged man began to recollect his teenage years and how he would pass the time sitting on the bleachers, ogling beautiful teens like this everyday.

Hmm, maybe that's why? he thought to himself as he continued to follow Grace's movement. All those times...

"Would you like anything to drink?" Grace asked from the kitchen

"Ummm, sure, anything's fine." he replied.

It was then that Jesse realized his fixation on Grace. She reminded him of someone from his younger years. Maybe, if he played his cards right, he could finally get to win at least one conquest, granted she was already in college.

Meh, semantics.

While lost in thought, Grace began to hum as she walked up to him, holding a cold beverage, it snapped him back from his reverie. He watched as she got closer, he saw how her thin frame fit perfectly into the clothes she was wearing. Her long legs covered by tight black leggings, white ankle length socks and a tight navy shirt that provided him with a clear mental image of what her medium sized breasts might look like, when she handed him the bottle of water, his eyes locked right into her captivating gaze.

He took a deep breath. "I want to be candid with you, you are a true beauty Grace. Honestly, in fact, you remind me of this one cheerleader I was heads over heels in love with in High School. I remember asking her out once, but she turned me down so quickly that it gave me an Indian burn." He finished speaking and let out a sly laugh.

"I do?" she asked as she sat down next to him.

"Yeah, Victoria Kennedy, man what a trip." he said as he took a sip of water

Grace turned to him, she looked to her right as if trying to remember something.

"Wait, wait a moment... my mom's name is Victoria, in fact, her last name before marrying dad was Kennedy. Holy shit, she was also a cheerleader in High school." Grace said, suddenly surprised.

"Small world." he said without breaking his voice or showing any surprise in his face. He realized the moment he saw her that she resembled someone he had once met in his life, it just took him a few to put two and two together. He also knew that if he showed any kind of surprise it might make her uncomfortable.

At the moment he held the power over the conversation, he was trying to become that tantalizing mystery this young woman needed in her life, and he was also determined to become that one night stand that every woman has at least once in her life, the one that she will always remember and masturbate to, even when she's married and has had children of her own.

"Wow, unbelievable." she said softly.

Jesse thought very carefully, if he said the wrong thing he could mess everything up. He needed to reassure her that he was interested in the young woman in front of him and not someone from his past.

"You truly are beautiful." he said as he stood up and extended his hands to hers. Once she gave him her hands he proceeded to stand her up.

"So beautiful." he said again as he touched her hair, it was soft to the touch. He used that opportunity to brush his hands across her left cheek as he studied her reaction. It was true, he never got to date her mother, meaning he never got the chance to fuck her mother, but by Jove he will make this teen goddess his tonight.

"I... I think we should stop. You're my roomat..." Grace said right as Jesse leaned in and kissed her. His strong lips made her lose all her senses, instead of pulling away as she normally would've, she pulled him in closer instead. She loved how his strong masculine hands began to explore her nubile body.

Jesse wanted this, he knew that any minute now Beatrice could come walking in. A threesome would sound appealing to any straight man, no one would ever deny that, but at the moment the only thing he wanted was this beautiful woman to himself. He did not want to rush anything but time was of the essence. As their tongues danced with a sulty passion he grabbed her ass, picked Grace up and carried her to her room.

The room was as clean a room as you could make it, it had a hamper in the far back left corner, a full size bed with a white, wooden frame, multi pillows both pink and white and was draped by a white soft sheet. As he laid the teen blonde unto the bed, the soft smell of the clean linen mixed with her feminine perfume suddenly engulfed him, elevating his already growing desire to ravage this beauty to unseen levels.

While Jesse continued to softly kiss Grace, his lips slowly migrated from its pink embrace to her soft, salty neck. He nibbled it, putting just enough pressure as to not mark her in any way, this caused her soft moans to escape from its hidden location.

God, even her moans are fucking intoxicating.

The sounds of their kissing and her soft moans started to get his cock hard, he moved his hands slowly from under her shirt, down towards her flat stomach, it was offered no resistance as it went under those black leggings and unto her wet pussy.

"Mmmmm." Grace softly moaned as his finger reached her now aching love hole. The reality of the situation escaped completely when he began to softly play with her clit. "Wow..." she let out another sweet moan and then looked down at what this much more experienced man was doing to her. "...Mmmmm."

Like any veteran to the sex scene Jesse saw all the signs that she was now ready for more, the middle-aged man got on top of her and started kissing her again, lifting her shirt, removing her bra and then kissing her chest. Her breasts were soft, she had big pink areolas, her nipples were hard and fit perfectly into his mouth.

Grace moaned softly as she felt his mouth and tongue tease her nipples, her pussy was now aching for some attention and she let him know by rotating her hips.

Jesse kissed the top of her stomach first, then slowly, little by little, his mouth started reaching the lower part of her flat stomach. Once he heard her breathing begin to sound heavier, that's when he calmly, softly began to lower her leggins, grabbing her white panties at the same time. Within a few seconds he was met with a pair of sweet smelling pink pussy lips.

Jesse took a deep sniff while looking at Grace's face biting her lower lip.

"Yummy, it smells so sweet." he said softly as he used his thumbs to spread them open, her pussy hole looked so small and tight.

Holy shit that looks tight, I think I just hit the jackpot.

Almost as instantly as his mouth latched onto her heavenly smelling snatch her back arched.

The beautiful teen needed this just as badly as he did, her breathing became shallow and hard. Grace began to suck in her breath as his tongue continued to explore what she had to offer. "Ahhhh, ahhhh, ahhhh... wow..." she again sucked in her breath as Jesse noticed her grab the bedsheets and squeeze them. "...Ahhhh." her soft voice let out a loud moan as he continued to give her a blissful experience.

Jesse continued to softly tease her, sucking on her pink lips that now had become soaked in her love juice, licking and suckling on her clit until her moans had become so audible that they echoed throughout the quiet room. He put his hands under her soft ass and lifted it up, arching her back in the process until he was now eating that pussy the way a man would eat a watermelon on a hot, dry day.

"Oh my Godddd... Yes!" Grace suddenly screamed as his tongue probed even deeper into her aching love hole than it had done previously. "Ahhhhh, ahhhhh, ahhhhh, AHHHH!" she continued to scream in a lustful manner as she began to rotate her hips. Jesse continued to enjoy himself as her soft mews, moans and screams of pleasure let him know he was doing it right. "Oh my God!" she screamed again as he squeezed her butt cheeks. "I... Ahhhh, ahhhhh!! HOLY..." the beautiful teen managed to muster as her long legs clamped onto Jesse's head, locking him in. "AHHHHH!! I... Shhhhhhhhiiiiiiittttttttt... AHHHHHH!!" and with those beautiful sounds of pleasure her whole body began to shake as she was hit with her first orgasm of the night.

After a few more minutes of enjoying that delicious sweet nectar, he lowered her hips.

Jesse looked up from his position and could see her flushed face as she looked down at him, he smiled as he again put his mouth to work and watched as Grace's mouth opened to let out more beautiful sounds. He inserted and twisted his finger upward and began tickling her g-spot as his mouth licked and sucked on her sensitive clit. She must've been too sensitive since she abruptly stopped him.

"Okay.... okay, that's enough." she said slightly out of breath and smiled at him. The older man moved upwards to meet her gaze. She observed how handsome he was, suddenly age didn't mean anything to her. Grace then quickly grabbed his face and kissed him deeply, tasting herself on his lips.

As their tongues again twirled in a passionate embrace, Jesse slowly removed his pants and underwear. He released the kiss and moved up, sitting slightly on her chest, his hard member right in front of her face.

Grace didn't waste any time, she put his cock into her mouth almost immediately, sending a flood of pleasure throughout James's body. His eyes gazed as her beautiful lips wrapped perfectly around his thick Shaft. The beautiful woman bopped on his manhood with such perfect precision, using her tongue and tight suction action, that he literally had to keep himself from cumming by pulling back.

Grace giggled at his reaction. "Come here, don't run away." she said as she pushed him in closer and went back to work.

James was fighting with all his might, and that caused Grace a sense of satisfaction, watching this man try to pull back as he moaned and whimpered. She found it to be both hot and adorable.

Finally, he couldn't take it anymore and pulled back. "okay...that's too good." he said to Grace, causing her to giggle.

They kissed and embraced for a few minutes, giving James a much needed respite, eventually he felt the call, his erection poised to feel that tight embrace as Grace continued to kiss him passionately. In one sweet and slow thrust he felt how his thick shaft was suddenly hugged, the walls contracted around his member as it acquiesced to him.

The nineteen year old beauty let out a soft moan as their tongues continued to dance. He slowly felt himself bottom out, her warm softness squeezing him gently. Jesse didn't move at all, simply allowing her time to adjust to him, his mouth moving to her now exposed breast.

A few seconds later, Grace began to pivot her hip, letting Jesse know it was time.

He took his time with slow thrusts as he saw her slightly wince whenever he went too fast. A few strokes later he sped up a bit. He repeated this until finally he saw no sign of resistance on her face.

It's time

In one swift motion he grabbed her long legs, opened them up as he now began to thrust fast and hard, feeling every inch of his super sensitive member engulfed by what he could only guess was the tightest hole he has ever felt. Suddenly he understood The Iliad and why Paris stole the beautiful Helen, forcing a fucking war against Sparta and all of Greece. This pussy he was experiencing was worth going to war for.

"Fuck!" she screamed as his thrusts got even deeper. "Fuck! Fuck! Fuck! Fuck!" she continued to say as his onslaught continued, she loved hearing his manly grunts as he continued to make her feel pleasure she had never felt before. She looked down as his thick shaft disappeared inside of her, fulfilling a yearning she didn't know she had, then watching it reappear and again disappearing.

Jesse watched her beautiful face as each thrust made her cheeks even more rosier. He grabbed her face with both hands, using his thumbs to clear away some loose strands of hair. He thrusted faster and faster, deeply while looking at her stunning and mesmerizing beauty. Her face now showed pure pleasure. He could see her orgasm building, her face now showed the agony of a woman who wanted to orgasm.

"Yeah?" he said while a few drops of sweat from his bow fell onto her face. "Yeah?" he again asked as her eyes looked at him, suddenly she looked like she wanted to cry, but it wasn't from sadness, it was from desire-- the desire to orgasm.

"Pleas... Fuck! Oh... That's it, like that! Yes!! Fuck, Fuck! Ahhhhh! Ahhhhh!" she began to scream as her face remained lock in its location, she watched as this handsome man's face simply watched her. "Fuck me! fuck me! FUCKKKKKK MMMMEEEEEE!!"

Suddenly her entire body was rocked with orgasmic pleasure causing her to shake. Jesse felt her tight pussy literally pull him in deeper as if asking him to breed her. "Oh my gosh! Oh my gosh!" she said as she felt him continue to fuck her with the same intensity.

The bed creeked loudly as they continued to fuck, sometimes fast and hard, other times slowly. They fucked in different positions, sideways, cowgirl and reverse cowgirl (which Jesse really loved, watching those white cheeks bounce really made him feel alive) stopping only to give him time to regain some stamina.

After a few more pumps he pulled out, turned her over and put his mouth on her pussy, sucking those perfect pussy lips like a man that hasn't gotten laid in months.

"Ahhhh!! Jesus Christ!" she said loudly as he reintroduced himself now in a doggy style position. "Ahhhhhh, Ahhhhhh!"

Both of them were now covered in sweat, Jesse wiped some from his brow, he looked down at her white ass cheeks, her very thin waist, her milky white back, her long hair. How the fuck did I get this lucky, this has to be a fucking dream. he thought to himself as he shifted his position to allow himself an even deeper angle of penetration into her, adopting a horse-like martial arts stance, then grabbed her long hair and pulled it back, pushing him even deeper into her.

"HOLY SHIT!!" Grace suddenly screamed as her entire body was caught unawares.

Jesse then went to work, thrusting with renewed enthusiasm, her pussy was so wet that he could hear it with each thrust.

"Oh my God, I think I'm going to cu.... aga..." the blonde teen couldn't finish the sentence as she was hit with another orgasm. This time, Jesse couldn't hold on, that tight pussy grabbed him in such a way that he was going to empty himself inside her. Nothing was going to stop it.

"I... am going... to cum too..." he said as he felt his strength fade away.

The teen was so enthralled by this perfect orgasm that she didn't even hear him, instead pushing back as if looking to extend her pleasure. The middle aged man felt it again, as if her tight pussy had grabbed his cock, pulled it in deeper.

It was to his knowledge the most amazing orgasm he himself had ever felt. Her pussy literally milked him, squeezing out every drop.

It was perfect.

They both collapsed, drenched in sweat, Jesse turned her head slightly to give her a kiss and she looked exhausted, her face was completely flushed as she barely managed to kiss him. He laid next to her catching his own breath, his heart beat so hard that he could feel it. A few moments later he heard heavy breathing, it appeared that Grace had fallen asleep.

Jesse slowly got up from the bed, his eyes felt strained as he rubbed them. It was late, he felt spent, and the truth was that he just wanted to go home. He looked at Grace as he began to get dressed, Beatrice had asked him to stay and despite how he felt, he chose to stay for a few more minutes.

Speaking of which, where was she?

He looked through his phone as he slowly closed Grace's door, there were no messages.

The middle aged man sat in the living room, his eyes felt heavy as he leaned back on the sofa. He wondered what Ashley was doing right at this moment. He pulled out his phone again, opened the email that Bill had sent him. He looked at it.

He breathed in a deep sigh.

*Click, click

Jesse looked up as the front door opened and in walked Beatrice, she put her umbrella aside and closed the door.

"Sorry, it took longer than expected. I honestly didn't think you'd still be here." She said as she removed her shoes and walked into the apartment.

"Well, you did ask me to stay." He said, quite abruptly. He felt a bit upset at her words but chose to keep it in check.

"Don't take it like that, what I meant to say was that most guys once they fuck, they split." She said as she sat walking towards Grace's room. She opened the door, peeked in, then closed the door. "She's naked, and asleep, must've been really good."

He watched as she walked to the kitchen.

"I really wanted a threesome." She said as she pulled a pitcher of water from the fridge and filled a cup. "She's got a nice ass, right?"

"That she does." He responded.

Beatrice walked to the couch and sat next to Jesse, her eyes looking deeply into his soul, as if it was trying to read something elusive. They both shared a look before Beatrice got on top of him, her lips locked on his and they shared a deep, passionate kiss.

While they kissed, Jesse's hands cupped her nice ass through her pants while she kissed him like a ravenous woman, her mews sounded beautiful and her soft lips felt wonderful to him.

They spend the next few minutes just kissing, feeling each other up, until Jesse finally picks her up and carries her to her own bed. There he slowly removed her clothing, he tasted her soft flesh, nibbling on her neck, her brown nipples, her stomach. When he finally made it to her melting love hole, he licked those tasty pussy lips with deep desire.

Beatrice's back arched as she felt his mouth touch her sensitive area, his tongue and mouth made her feel pulses of pleasure. Little by little, she let herself go, allowing this handsome man to perform wonders on her with his fingers and mouth.

Jessie took his time, her taste was very different than the other women he's been with, but it was just as enjoyable to him. Minutes passed and he kept at it, not rushing anything. The sounds of her sweet moans were contained for the moment as he slowly brought that tanned goddess to the edge. He could feel it, her legs shaked slightly, her butt would lift off the bed for seconds at a time, her breathing was heavy. It became his mission to get her orgasm, patiently he waited, despite his mouth feeling tired, he kept at it.

"Shit, almost there, almost there, don't stop." Beatrice said as she grabbed the back of his head and pulled him in, locked him in. "Almost there... Yes, yes, yes, ye...." She moaned softly as she felt at the edge. A few seconds later she felt her body give in as she orgasmed.

He watched her as she shaked and said something in Portuguese that he couldn't understand. His fingers continued to work her until she finally stopped him.

"Fuck, that was good." She said with her exotic accent.

Jesse smiled and got up, he removed his shirt as Beatrice removed his pants. Almost immediately, his cock was inside her mouth. Her hands stroked him as her tongue massaged the back of his cockhead. She bopped slow then fast, took him deep down her throat then only worked on his head. It kept the nerves on his cock always guessing what was coming next.