Wake Up Lisa Mitchell Ch. 25

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An amendment, a first, and a story...
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Part 17 of the 18 part series

Updated 08/27/2023
Created 09/11/2020
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JamesVI
JamesVI
65 Followers

Lisa looked at the items on the bed. There was a black dress, thong panties, no bra, and some high-heels. Thanks to Mark, the mature beauty was more used to outfits that might not have been a preference of hers in the past.

She took a deep breath and started to disrobe, placing her clothes on the chair in the room. After about twenty minutes, Lisa slid the doors open. The busty brunette locked eyes with Charles, walking towards the coffee table in the living room. She was wearing four-inch black Loubi Queen Ankle Strap Sandals and the clicking of the heels resonated in the silence.

The Susana Monaco twist front halter mini dress looked amazing on the mature beauty. It had a plunging neckline which did not help conceal her big tits, but the rest of the dress was tasteful. Being fitted through the waist and hips accentuated her body, with the halter straps crossing over in the back. Cut above the knee but not mid-thigh the sleeveless dress didn't expose too much of Lisa's legs. At her waist, there was a center front twisted design to add some elegance to the item.

Charles spoke first, "You look absolutely stunning Lisa."

Shaking slightly from nervousness, the mature brunette accepted the words from the VP with a slight grin showing appreciation.

"Since it's late, I thought it best for us to get a proper dinner," Mr. Grant continued

"That would be wonderful, Thank you, Charles," Lisa replied.

The tall man positioned his arm for Lisa to take and they walked out of the room to the elevators. Mr. Grant escorted the sexy woman inside and pushed the button for the lobby. The ride down was quiet for the most part.

Once they made it to their floor, the elevator doors opened. Charles gently but strongly grabbed Lisa's hand and they walked out into the lobby. Each step from the busty brunette echoed as her heels clicked against the marble floors. The noise caused a few patrons to look in her direction, some gawking and admiring, while others looked in disgust.

Mr. Grant had a ride awaiting them as they made it outside. The two of them sat in the backseat and headed towards the restaurant. On the way there, Charles engaged Lisa in some small talk.

"Do you like steak?" Mr. Grant asked

Nodding gently, Lisa responded, "Yes. Where will we be going?"

"Lucero," Charles replied

Mrs. Mitchell's eyebrows raised upon hearing the name. Lucero was one of the most expensive steakhouses in the city. Once they arrived, Charles guided Lisa inside the steakhouse and they were seated soon after, due to his reservation.

The dim lighting in the space created an intimate setting. After ordering a bottle of wine, the VP asked for a few appetizers and discussed general things with the mature woman. Charles was strategic in keeping the conversation light. He didn't want to shake up her emotions, focusing on her work.

Progressing through the three-course meal and a couple of bottles of wine was more than what Lisa had expected tonight. She was feeling relaxed and more flirtatious thanks to the company and beverages.

Other than being in great shape, Charles was charming, appropriate, and funny. Lisa could see why someone might have an interest in him. The sexy woman thought about his body and strength before her thoughts shifted to what was between his legs. Her pussy pulsated slightly at the thought of what they would engage in tonight.

Lisa was also thankful that he wasn't forceful with a decision due to the situation that had presented itself. Sure, he might have provided twenty-four hours, but he could've asked for a decision on the spot.

Mr. Grant paid the bill and they made it back to the hotel. This time as they walked in, Lisa pulled on his arm and used him for slight support. She felt the wine more so now and was feeling the heat radiate from the strong, tall man.

When they made it up to their floor, Charles surprised the mature brunette by pinning her up against his door.

"Oh!" Lisa gasped

Mr. Grant then unlocked the door before he leaned in towards her right ear and whispered, "Will I need to ask for permission tonight?"

The mature brunette had heard the door unlock and her next action gave Charles his answer. She looked directly at him. Her blue eyes showed a smoky mix of alcohol and sexual desire. Lisa pushed back against the door, turned around, and walked into the room.

Charles Grant smiled internally and followed her inside, letting the door close behind him. He eyed her ass and felt his cock grow at the thoughts of what they would embark on tonight. Mr. Grant poured her a glass of wine and sat next to the sexy woman who was seated on the couch.

"Cheers to a smart, sexy, and driven woman," he said, sprinkling in some compliments.

Lisa smiled, the intoxication from the evening had already eased her tension. Her long legs were crossed in his direction. She leaned in and gave him a friendly bump.

The former athlete placed his drink on the table and gently caressed her cheek with his thumb, leaning in for a kiss. Mrs. Mitchell closed her eyes, placing her drink near his and awaiting his advances.

As his lips met hers, she felt her sex react to the moment. The beautiful woman kissed Charles back. Her mind and body fully engaged to move forward with his advances.

A brief moment later Mr. Grant had her lying down on the sofa. Lisa had spread her legs, causing her dress to ride up her womanly thighs. Charles was positioned between them, gripping and caressing her smooth left thigh. Mrs. Mitchell caressed the right side of his jawline while they continued to make out.

She had one foot on the ground while the other was on the couch. Mr. Grant leaned down towards her right leg, gently kissing the inner side of her knee to her upper thigh. Lisa took a deep breath, her soft hands feeling the smoothness of the VP's head as he approached her mound.

The smell of her sex grew stronger to the mature man as he was at eye level with her panty-covered sex. Mrs. Mitchell gasped while pushing down on Mr. Grant's head. The sexy brunette shifted lower onto the couch which caused Charles to lean back. He reached for the beautiful woman's waist, tugging the thong off, throwing it behind the couch.

"Ah," Lisa moaned, feeling the cold air hit her visible wetness, knowing that she was about to get a pleasure that she hadn't had since she was with Mark. The VP leaned in between her now widely spread legs, tasting the sweetness of the mature woman's sex.

A deep whispery gasp followed from the busty brunette as she felt the pressure from his tongue on her clit. Slight coos and moans encouraged Mr. Grant to continue. Lisa was gently squeezing and rubbing her tits as the pleasure increased between her legs.

About five to ten minutes later she felt a void below but was met with a passionate kiss from the VP. Lisa Mitchell opened her mouth to taste her own juices as their tongues danced in unison. While the two made out, the sexy mature woman reached between them trying to release Charles' member from the restraint of his pants.

The VP felt her fumbling with his belt and leaned back before standing up next to the couch. Mrs. Mitchell felt the absence of his warmth. Charles watched as Lisa opened her deep blue eyes and looked at him. They were a little glazed and smoky from a mixture of alcohol and sexual desire.

She sat up and shifted which caused her juices to rub on the couch. Lisa reached for Mr. Grant's belt, and the clicking of the metal buckle resonated in the room. Unzipping his trousers, Lisa pulled them down, feeling the mature man's strong thighs.

After, Lisa tugged down on his boxers. Mr. Grant's penis sprung up slightly, touching the bottom of the sexy woman's chin. Her mouth watered as she eyed the semi-erect cock. Mrs. Mitchell ran both her hands slowly up to the strong man's torso. Lisa felt his abs, the firmness of his waist until she was gently cupping Mr. Grant's member.

His length was visible as the tip of his cock was pointed downward, even though she was holding it in her direction. The sexy brunette leaned down to take the tip of his member in her mouth. Charles moaned as he felt the warmness of his tongue. Mrs. Mitchell slowly bobbed her head back and forth, taking more of his cock each time.

Lisa's cheeks hollowed, showing how tightly she was sucking on the VP's cock. Her pussy was pulsating as the sexy brunette felt her actions causing Mr. Grant's member to stiffen.

Mrs. Mitchell moaned while using her tongue to pleasure her contractual partner. After a few more seconds, Lisa leaned back and looked at the long, lubricated seven inches in front of her. Just as she was about to go back for more, Charles gently grabbed her hair on the back of her head.

The busty brunette looked up and saw Mr. Grant lean down for a kiss. As she felt his lips and tongue aggressively embrace hers, Lisa felt herself lift up a little. A few seconds later Charles broke the embrace, allowing Mrs. Mitchell a few seconds to catch her breath.

"Turn around and bend over the couch if you're ready Lisa," Mr. Grant whispered to her before leaning up.

Almost as if in a trance, the tall brunette stood up, turned around, and got on her knees while on the couch. As she bent over, Charles licked his lips which eyeing her womanly ass. Lisa felt his hand push down on her lower back, causing her rear to stick out a little more. Mr. Grant then lined up his cock and slowly drove it into her sex.

"Oh god," Lisa moaned as she felt the length of his shaft entered her warm pussy.

Mr. Grant stayed there for a moment before he grabbed her waist and steadily started to fuck the brunette woman. The sexy woman's moans grew louder with each thrust which penetrated her harder. She was now leaning forward with her chest resting on the back of the couch.

Charles smacked her right ass cheek, causing Lisa to yelp. The pleasure mixed with pain unlocked the sexy woman's desire for more. She pushed back on Mr. Grant's shaft, trying to meet his thrusts. When he saw this, the VP thought to push the mature wife further. He leaned forward and grabbed her hair in a fist.

With her hair being pulled back, Lisa gasped. She felt a dominance and strength from Charles and it excited her more.

The former athlete twisted her hair in his grasp, giving him a stronger grip. He then drove hard, slamming his cock deep into Ryan Mitchell's wife.

"Ah fuck!" she yelled, the speed and power of the man behind her was more than she had ever taken.

Sounds of his groin hitting her ass echoed in the living room. With each thrust he slammed harder into her dripping wet pussy, emitting yelps from the top-heavy brunette.

Carnal grunts emitted from the sexy woman's now dry lips. Her neck was in some pain but her desires were strengthening in her submission.

Mr. Grant released Lisa's hair from his tight grip and pulled his cock out of her burning pussy.

"Ah," she sadly whispered, laying her head on the cushion of the couch. When she opened her eyes, Lisa saw the tall man's wet shaft in front of her.

She leaned in on his penis. Her tongue pressed against the right and left sides of his hard member as she tasted her juices. Mrs. Mitchell licked her lips, and noticed the veins of Charles' manhood as she did this. Internally she felt good that this man's cock was responding to her this way.

After a couple of minutes of enjoying her mouth, Charles stepped back and led Lisa into the bedroom. As he made it to the bed, Mr. Grant turned towards the mature woman and kissed her deeply. Mrs. Mitchell reached for his cock and stroked his member as they made out.

The forty-three-year-old mother was completely naked now. Lisa climbed onto the bed, laying on her back. She spread her long legs. Charles accepted her invitation and pressed down with his hands on either side of her head to help him balance.

Mrs. Mitchell reached between them, taking his member and guiding it to her pussy. Charles Grant easily pressed into her love box, causing the sexy woman to moan.

As he built his pace, Lisa touched Mr. Grant's strong arms with her soft manicured hands. Although not one into muscular men, Mrs. Mitchell didn't lack an appreciation of a physically fit man. Charles then pushed up and pulled Lisa to where her ass hung off the edge of the bed.

After pushing his cock into her sex, Charles leaned down and whispered to Lisa, "Lock your arms around my neck and hold on."

Lisa was confused but did as he said. She felt him grab her upper thighs and lift her up off the bed. Instinctively she wrapped her legs around his waist as Charles shifted slightly. Once he had a good hold, Mr. Grant started to fuck Mrs. Mitchell while standing.

The tall brunette felt her thighs burn and her core tighten as she felt the VP's rod drive in and out of her pussy. Her tits were pressed up against his upper chest.

Charles slowed down, and the sensation of his cock stimulated the upper wall of Lisa's pussy. She looked down at the sweaty man and kissed him passionately. Both of them made out for a brief moment before he gently laid the sexy woman on the bed. Mr. Grant pulled her to the edge and knelt down. He opened Mrs. Mitchell's legs and immediately went down to lick and suck her clit.

A loud moan escaped her lips as she felt her arousal increase. Lisa arched her back and slowly thrust her groin towards Charles' mouth. She gently threw her head back with her eyes closed. As she lay back flat on the bed, the mature beauty grabbed each one of her nipples, pulling and pinching them.

"Oh god, I'm going to cum!" Lisa exclaimed, rubbing and squeezing her tits as Charles continued to pleasure her clit while fingering her wet pussy.

Mrs. Mitchell's breathing sped up and she shuddered a few minutes later as her orgasm shook through her body from head to toe. When Lisa came down from her sexual high, she noticed something different. Mr. Grant hadn't stopped licking her clit and her two holes both felt as if they were starting to be penetrated.

The sexy brunette noticed the sensation as Charles fingered her pussy and ass while eating her out. Lisa laid back as her body responded to the attention. She reached for her boobs and played with her nipples, noticing that they were still erect.

Mr. Grant had noticed her pussy was ready as well and he pulled out of sex and anus. The VP climbed on top of Lisa and kissed her deeply. Mrs. Mitchell returned his affection, moving her hands which were now pinned between them to his back and shoulders. She could feel his cock press against her abdomen, still hard.

Charles broke the kiss and helped guide Lisa onto the bed where he could fuck her missionary. Mr. Grant gently pushed his cock into her pussy, and a soft moan followed from the sexy brunette. Slowly he built up a pace that was close to what they were enjoying moments earlier.

As he fucked the busty woman again, Charles moved an index finger close to her mouth. With her eyes closed, Lisa instinctively opened her mouth and started to suck on it, licking it nearly clean. When he pulled it out, Charles moved his other index finger to her lips and Mrs. Mitchell did the same thing.

"Did you like tasting yourself, Lisa?" Charles asked.

"Ah, oh, ah, yeah, oh," she moaned with a partial answer as she felt Mr. Grant's cock penetrate her.

He pulled out again and bent her over the bed, pushing his cock into her pussy immediately. The force caused Lisa to lean forward. Mrs. Mitchell was able to balance on her hands as Charles pounded her sex. She cooed and moaned as the force was causing her things and ass to ripple again.

Mr. Grant slapped her ass.

"Ah!" Lisa moaned

A few more slaps followed, with responses from the busty brunette.

"Ah fuck!"

"Ugh"

"Oh god!"

The pain and pleasure were getting the sexy woman close again. She felt the VP's thumb push into her anal passage.

"Yes, finger my ass Charles. Oh god!" Lisa screamed as she felt her anal bud stretch. The burning sensations on her rear and her sphincter were near the same.

Momentarily she felt a stoppage and noticed her pussy was empty. Lisa heard a sound and noticed Charles grabbing a bottle of some sort.

"What's that?" the mature woman asked.

"Lube," Charles answered.

Mrs. Mitchell felt the cold oily liquid drip onto her anal bud, travel down and drip off her pussy. Charles had also covered his cock with it to ensure Lisa's first anal experience would be pleasurable.

"Spread your legs and relax, you'll be okay," he whispered in her ear before moving behind her.

The forty-three-year-old anal virgin closed her eyes, slowly spreading her legs and taking a deep breath.

She winced slightly as she felt pressure applied to her puckered hole.

"Relax," Charles whispered.

He watched her starfish contract and release. When she looked to be relaxed, Mr. Grant pressed the head of his lubricated cock inside her ass.

Lisa gasped and gripped the bedding tightly. She felt the VP's thick cock slowly drive and reverse from her hole. Because of the lubrication, the pain was next to nothing but the busty woman felt a pleasure unlike ever before. With each thrust, her pussy and clit were stimulated more and more.

As Charles built a steady pace, Lisa lifted her chest off the bed, resting on her forearms and elbows. The sexy woman started to meet the thrusts of the fit man finding an arousal that was deeply overtaking.

"Ah fuck, oh, god, oh my!" she yelled. Her knuckles were white as she focused on her anal bud and pussy.

Mr. Grant reached down and rubbed her love button.

"Ugh," Lisa grunted in a sexual yet animalistic way.

About a minute later the anal sex pushed the mature goddess over the edge.

"Fuck, fuck, fuck! Oh my GOD!" she screamed loudly in ecstasy. Mrs. Mitchell felt her release shoot through in waves as a second orgasm rocked through the mature woman.

The intensity was so strong she shook and quivered as she rested her upper body on the bed. Charles Grant smiled as he saw the tall statuesque brunette revel in her release. Her body had a thin sheen of sweat from the night.

She couldn't remember when this happened, but the sexy woman was lying completely on the bed now. Lisa felt like she blacked out for hours but it had been mere minutes when she realized the VP wasn't behind her.

Mrs. Mitchell heard a click and release of a door behind her. She turned around and saw that Mr. Grant had gone to clean his groin and cock. He stepped through the door, making eye contact with Lisa.

"Well, that was something, Lisa!" Charles exclaimed with a smile. He watched the mature woman blush before continuing, "Are we done for tonight?"

Instinctively but unintentionally, Lisa bit her lower lip as she gave a half smile. Her time spent with Charles so far had unlocked something in the mature woman. The drunken haze that started the night had turned into a sexual smoke. Now she looked at the man in front of her as if he was an aphrodisiac for her needs and desires.

Slowly but seductively, the busty brunette turned to where her back was on the bed. Charles traced her tall body, drinking up the sight of her long legs, semi-fit torso, and big tits. The VP noticed that her nipples were hard.

Mrs. Mitchell used the bed to help herself sit up before meeting her contractual partner where he stood. She wrapped her arms around his neck and kissed him deeply. The two made out, feeling each other's nakedness again. Lisa could feel Mr. Grant's cock press against her abdomen.

She kissed her way down to his groin and pleasured his cock with a passion he hadn't seen from her yet. Lisa sucked and licked his shaft until feeling the VP's legs tighten. Charles grabbed her head and screamed loud enough for the two of them, "I'm cumming, fuck!"

Mrs. Mitchell felt the VP's grip tighten, holding her head in place as his sperm hit the back of her throat. Shot after shot of his cream filled the mature woman's mouth. Lisa could feel the ample liquid starting to fill the space causing her to cough and swallow some. When she did this, Mrs. Mitchell felt the warmth go down her throat. A little bit of his cum seeped through the corner of her lips as Charles pulled his cock out slowly.

JamesVI
JamesVI
65 Followers