Wake Up Lisa Mitchell Ch. 34

CHAPTER 34

Lisa moaned as the pleasure between her legs increased. She shifted her body, lifting her hips trying to press her clit toward the feeling of satisfaction.

In reality, the statuesque brunette was being fingered and licked by Benson Calhoun. After meeting with his son, Benson went to the wine cellar to enjoy a glass of wine, waiting for his pill to go into effect. Once the signs were there, he went back to the bedroom, looking to relish the rest of the night.

"Mmmm...," she moaned, as her arousal interfered with her slumber.

Ms. Bailey's breathing became deeper the more the mature man penetrated her sex with his digits. Lisa moved her hands to her tits, massaging her massive boobs. As Benson sucked her clit, the busty brunette twisted her nipples gently with her index fingers and thumbs, before pulling them.

Her breathing increased toward another moment of release which Mr. Calhoun could tell was near. Seeing her body starting to get close, he stopped and watched Lisa. Her hips and legs shifted and rotated as she relished another opportunity of bliss.

The busty beauty moaned in dissatisfaction which woke her up. She looked groggily around the room before seeing Benson between her legs. Taking another deep breath, Lisa rubbed her eyes briefly before she felt the mature man's hands and mouth return to work.

Ms. Bailey bit her lower lip gently as her body started to get revved up again. Her sweet nectar was in a near-constant flow as it again immediately lubricated Mr. Calhoun's fingers.

Instinctively, she lifted her legs, spreading them wider to allow her contractual partner an opportunity to drive deeper into her pussy.

With his hard cock ready to go, Benson took his fingers out of Lisa's pussy, lining himself towards her throbbing sex, pressing his cock in the void that he had left momentarily.

Because she had shifted some in her sleep, one of Lisa's high heels had come off her foot. Mr. Calhoun noticed this when he held her ankles while building up a better pace.

As he continued slowly fucking Lisa, Mr. Calhoun took the other high-heel off her foot, with the only items left on the brunette now were the earrings, necklace, and bracelet.

They both grunted and moaned as Benson plowed deeper and deeper into Lisa's pussy. She felt the pressure and strength from each thrust as her body pushed back against the mattress.

The hard fucking reignited the busty brunette.

"Deeper, oh yes, deeper," She moaned to him.

Benson released her ankles, pressing down on her upper thighs, spreading the mature woman's legs further.

Again he fucked her fast, then slow, deep and hard. Each thrust caused a sound of pleasure to escape the busty beauty's mouth.

Noticing that he was starting to get tired. Lisa pressed her legs against his hands to imply that he stop, which he did, pulling out of her sex slowly.

Lisa repositioned her body where she was lying on the bed, chest down. She rested her upper body on her elbows and forearms. With her head near his groin, the sexy brunette saw the mixture of their juices glisten off the mature man's cock.

She leaned forward to suck his member.

Swirling her tongue around his shaft, Lisa licked and sucked the cock that had pleasured her tonight. Her pussy was still swollen and throbbing for a chance to feel him penetrate her once more.

Benson watched as she eagerly bobbed her head, tightly gripping his shaft with her mouth.

Moments later, Lisa asked Benson to lie down on the bed. Once he did this, she lowered herself on him again, missionary style. Straddling the mature man, Lisa leaned down, kissing him.

The two made out as she slowly started to fuck Benson Calhoun.

"God your pussy is so nice, you're so beautiful," Benson told her as she sat up. Lisa had never done this before, but she was squatting on his cock, Asian cowgirl style, driving herself onto his shaft while using the headboard for support.

The mature man reached for her enhanced tits, caressing them as Lisa felt the stirrings start to connect throughout her body.

"Pinch them, Benson, Pinch my nipples again," she told him, breathily as she kept her pace constant.

Just as the Cowboy did this, Lisa's thighs shook as another orgasm rocked through her body.

Ms. Bailey hunched down, her face near Benson's neck as she breathed heavily. The warmth of her breath touched his neck as he continued to play with her nubs.

Lisa couldn't remember so many orgasms from intercourse in one night. It had been a while since the hotel and the bondage-like moment with Mark. The night she hid her partially naked body behind the door when the hotel employee checked on them. The same night Mark used the toy which brought her to multiple releases.

The well fucked brunette rested her body on top of the rich man's. His cock was still in her pussy. Wearily, Lisa lifted herself back up. Her mouth dry, her body sore, and her pussy, still wet for more.

Lisa was impressed by the old man's stamina and couldn't believe he was ready to go after the initial release earlier in the night.

And because of all the pleasure he provided her, Lisa knew that she had to show him how a partnership worked.

"Benson, can you stand over there?" Lisa softly asked him as her fatigue started to creep in.

Mr. Calhoun nodded as the sexy woman got up off of him. She pointed toward the window that had the drapes. Making his way toward the spot, Mr. Calhoun turned around and waited to see what she was going to do next. Slowly getting off the bed, the sexy brunette made her way to the mature man.

Benson watched as she made her way to him. The way her hips swayed, her body a desire for any red-blooded man from her legs to chest, those blue eyes and delicate face, and an immortal sexual prowess on the level of a goddess.

As she neared, Benson Calhoun pulled Lisa in close, their naked bodies feeling the heat from pressing against each other once more. His lips locked with hers for another momentary make-out session.

Their tongues interlocked and danced as their hands roamed each other's now familiar bodies.

Lisa found his cock, stroking it as Benson caressed her ass. Ready to show her appreciation of the multi-orgasmic night, Ms. Bailey released his lips from hers, kneeling in front of the mature man. She already had one hand on his cock while the other traced down the middle of his chest, using him for balance.

With her blue eyes, Lisa looked up at Benson with a familiar, sexually possessed look that she had with other partners in the past. Anyone who could've peeked into the room would've thought that she was submissively looking up at the man, eager to please.

She stroked his shaft for a few seconds before taking it in her mouth. Ms. Bailey closed her eyes as she wrapped her lips around his firm cock.

Lisa sucked tightly, her tongue pressing against the tip and sides as she devoured

Benson's rod. Pre-cum snuck from the tip of his manhood again, adding to the wetness that Lisa had created with her saliva.

The horny brunette felt herself getting warmed up again. Ms. Bailey reached for his balls with one hand while her other hand went between her legs.

Benson watched as the sultry woman only used her mouth. Her moans filled the room in-between the sounds of her sucking and licking Benson's shaft. Lisa pulled back slowly while sucking tightly on his cock, causing a popping noise as her mouth released his member from her grasp.

The busty beauty reached for her tits, squeezing them, pinching her nipples, and diving back in on Mr. Calhoun's manhood. Lisa again pulled back, this time

Benson's cock bounced up slightly before pointing right at the hungry brunette.

Leaning down, Lisa moved toward the base of his shaft, licking along the length toward the tip. She did this a few times before she heard Benson grunt, "Oh fuck....."

He grabbed his manhood, holding it quickly as his seed dribbled out of the tip of his cock. Some of it on his hand and some of it dropping onto the floor. Lisa licked her lips while kneeling in front of him. As she looked up, Ms. Bailey made eye contact with the man who had just finished ejaculating.

"That was so damn good," Benson told her, lending Ms. Bailey a hand to stand up.

"You are one beautiful, sophisticated, and sexy woman, Lisa," he followed, complimenting her as they stood, facing each other.

"Thank you, Benson. And you... You're one good lover," she replied, smiling at him.

They embraced once more, small kisses of affection between the two before they made their way around the room.

He offered her the bathroom to clean up while he grabbed his robe and went to wash up elsewhere. Although Benson Calhoun could've taken advantage of the situation further, he felt that what he enjoyed was good enough.

Once he got back to the room, he heard the shower running. Inside was an elegant, passionate woman who was washing a very well-satisfied and beautiful body. Instead of waiting, he found himself falling asleep within minutes.

In the shower, Lisa soaped her chest, arms, and legs, and even shampooed her hair. Not only did she need to feel fresh after this workout or marathon, but she needed something to help her mature body ease some of the soreness she felt would compound later.

As she washed up, Ms. Bailey thought about how she had engaged with a man not physically attractive to her. Benson Calhoun wasn't a looker by any means, but he was a good lover, and respectful. Ms. Bailey did appreciate that about him. Plus, the multiple orgasms made up for anything lacking in other departments.

The only problem was that her body seemed to have gone into overdrive recently. Ms. Bailey thought about the changes and felt that they may have driven her agreement with Tanner and Benson. Yet she intended to protect Shelby. Lisa wondered if she was using sex as a tool or if it was more than this.

"Do I need to satisfy my urges more often?" she asked herself.

"Am I insatiable?" Lisa continued in thought, "Did something happen with Mark? Have I always been this way? Was it the photoshoots?"

Each thought brought images of the past flowing in and out of her mind whether it was scenes of sex or photography.

"But Shelby, if I didn't do this, who knows what they would've done with the video," Ms. Bailey pondered, "I've got to stop touching myself so much. I know that my body feels..... different. This can't be normal, can it?"

The sexy brunette struggled with her emotions, at times justifying her actions but also questioning them. Lisa wondered if she needed counseling or therapy. Quickly her mind went to focusing back on the present and now.

One thing she did know was that the agreement remained incomplete. A weekend with Tanner Calhoun remained to close the deal, but also gave the mature woman a chance to satisfy her now daily urges.

Lisa came back to the room, hair dried and body clean. She noticed Benson sleeping peacefully. Ms. Bailey decided to lie down next to him, aware of the daylight starting to peek from the horizon.

Just as she felt her eyes shut, the movement next to her woke the brunette up.

"Wow, what a night," Benson said, turning toward Lisa.

He smiled at her and received the same as she spoke softly, "It sure was. Thank you, Benson."

After some more small talk, Mr. Calhoun made his way to the bathroom to get ready for the day. Lisa stretched her sexy body, knowing that it would be a long day but one where rest was the primary item on her agenda.

Lisa and Benson discussed some general things in the kitchen before Ms. Bailey left the house. They both were satisfied with the night and so far, with the agreement.

Once she was back home, Lisa went straight to her bed, waking up in the mid to late afternoon.

Checking her phone, there weren't any messages which Lisa was thankful for. She appreciated the opportunity to rest and relax.

At the Calhoun residence, Tanner met his father sometime mid-day.

"So Dad, how was the evening and the night?" he asked.

"Like I said last night... You're in for a treat. She's an amazing woman," Benson told him.

The younger Calhoun was excited. Even though they worked as a tandem at times, many women weren't able to reach the negotiation Lisa had put together. Many times the sexual favor was for Benson or for Tanner. If there was a woman who agreed to both separately, those were rare and special moments.

Tanner thought about the conquests of the past and thought to bring his experience to the table. He remembered that some women preferred to be commanded and dominated. While others wanted to control the situation. Tanner was going to push some buttons to see where Lisa wanted their weekend to go.

As Tanner went through his week he also thought about how for the first time, he could say that he'd fucked a mother and daughter, albeit separately.

In the middle of the week, Lisa received a text from Tanner. He outlined the duration from Friday night to Sunday afternoon which Lisa agreed to via text. But he didn't put any activities or events.

Knowing these were the final days of possibly locking in the Calhouns for AppTech, Lisa was upbeat and determined to ensure nothing ruined the deal.

Once more, she made it to their home. Tanner welcomed her inside and led her upstairs to his room. Lisa brought an overnight bag, carrying it with her as she followed him. His room was on the opposite end of where the photoshoot was. Lisa turned right, down the hall, then left, down a small hallway. This was followed by two steps down before entering Tanner's room. It was set up in a very private way, keeping a distance from Benson's.

"Thanks for joining me for the weekend Lisa. Here is the bathroom, and there's a single closet in there. If you don't mind getting ready, we can get dinner and then we will be out for tonight," Tanner said, pointing to some areas before leaving.

The sexy brunette looked around the space. Walking into the room, the bed was up against the left wall with two nightstands and generic-looking lamps that dimly lit the space. As she made it toward the bed, Lisa noticed a door on the same wall as the entrance of the room. This other door was for the bathroom. It wasn't as grand as Benson's, but good enough for a general bedroom.

Lisa noticed that Tanner hadn't told her about any outfits he had chosen, instead leaving the mature woman to find them in the closet. She found the closet to be a little messy. The clothing of the young man was scattered. He seemed more of a western, country club type based on apparel.

As she continued scanning the closet, Lisa found some shopping bags. Opening them, she found two dresses with tags, assuming they were for her to wear.

Lisa laid them on the bed and proceeded to get ready for the evening.

Tanner was in the living room watching some sports as he heard the clicking of Lisa's high-heels as she made it down the stairs. Part of his test was to see which dress Lisa would choose.

Hearing the television, Lisa made her way to the living room, in sight of where Tanner Calhoun could admire her beauty.

On her feet Ms. Bailey wore her favorite black heels, thinking of comfort and sexiness for the night. Tanner's eyes traced up the smooth, opaque, black pantyhose which provided some decency for Lisa's legs. His gaze up to her upper mid-thigh hit the hem of the red wine-colored dress.

The versatile Amira, Modal turtleneck mini dress was made of soft and stretchy jersey fabric. It had long fitted sleeves, a side split, ruched detailing, a bodycon silhouette, and of course, a turtleneck.

Ms. Bailey was going without a bra to ensure no bra lines but did opt for a thong for some sort of coverage. Apparent for all would be the indents her nipples had already created, even though they were completely covered. Her sex continued to throb and dribble from the sweet lips that were in constant arousal as she waited for approval from the young man.

Tanner licked his lips as his eyes made it to her chest before making eye contact with the busty beauty. Her piercing blue eyes looked down at him, a half-smirk as she allowed her mature body to be ogled once more. Mr. Calhoun admired her choice of dark red lipstick. The small detail of tying her hair in a ponytail also enhanced the look.

"Sophisticated and sexy," he said to her as they held each other's gaze for a mutual moment.

The young man stood up and moved close to Lisa, gently grabbing her at the waist as he leaned in toward the mature woman. Her intoxicating and sensual scent pulled him in closer as their lips met for a brief kiss.

Ms. Bailey closed her eyes as she felt the intensity of the moment through Tanner's lips. Breaking the embrace, the young man reached for her delicate hand, grabbing it gently. They both felt the sexual heat turning up but knew there was an evening that awaited them first.

"Let's have some fun tonight, whatcha think?" he asked.

Lisa smiled at him, nodding in agreement.

He led her to the garage and his truck.

Lisa appreciated the pantyhose as the difficulty of getting into the vehicle ensured that she would've flashed someone. Once seated, Ms. Bailey fixed her dress and waited for Tanner. He had received a phone call leading to a slight delay but he made it inside the truck and started to drive them.

"So.... Where are we going?" Lisa asked, slightly nervous.

"Dinner and then a bar or club or something. Cool?" he asked

Ms. Bailey was somewhat surprised. Never did she expect him to ask her this nor had any of the previous engagements she had been involved in since Ryan.

"Dinner sounds wonderful," she shared.

They both decided to go to an Italian restaurant, common amongst the trendy. After making it to their destination, they ate and chatted, and for the first time, Lisa found Tanner to be insightful, charming, and seemingly mature.

"When the quarterly earnings for their company came out, it only made sense to see if there was a play. I'm glad they allowed me to be on the board because now we can use some of that influence to ensure there isn't any industry cross-over," he shared as they were deep in a discussion of business with a bottle of wine down and another halfway empty.

"If they decided to do this, why didn't they wait for the next earnings or before? I mean it makes sense before sharing this information without it being insider trading right? Or because of the fact they are publicly traded, it had to be shared or else its insider...." Lisa added.

The engaging conversation led the couple to a third bottle and a little more playfulness as they continued the conversation.

"There is no way you are forty-four. I mean... you look thirty," Tanner shared.

Ms. Bailey blushed and thanked him for the compliment. Her body was warm and her eyes showed the visible signs of her inhibitions lowering.

They stared into each other's eyes a little longer, her body turned in his direction showing interest in the young man who was going to satiate her sexual starvation.

"You think we're ready to hit up another spot?" he asked with a gentle yet mischievous smile.

Without a word, she bit her lower lip and smiled back.

Tanner paid and helped the busty beauty out of the booth they were sharing. Ms. Bailey used him for support as they exited the restaurant. The sexual tension and heat built further between the two.

He was feeling pretty good and not just yet drunk enough based on his own experience. Mr. Calhoun helped Lisa get in the passenger seat. Then he drove them to their next destination.

This time instead of parking, Tanner used the valet.

Ms. Bailey took the hand of one of the men who helped her get out of the truck. The employee tried not to get caught as he peeked at the busty brunette's chest as she stepped down.

"Appreciate it," Tanner Calhoun said to the other man as he let them know the key was in the vehicle before walking to where his date was.

The couple walked arm in arm close to the door when Lisa looked up at the name of the restaurant.

Her blue eyes widened, shaking in momentarily alertness. Tanner Calhoun had brought her to the bar where she first met Benson and Tanner.

At the front door were some bouncers now who checked Lisa and Tanner's IDs. Once they were inside, Ms. Bailey noticed that the restaurant she came to by herself was different. Sure the layout was all the same, but the music was louder, the lights dimmer, and the single women, older... or her age.

"You know, that first night you came here and met us, I felt like you came here often," Tanner said, leading her to the bar.

"But the more we were here talking, I realized, maybe you hadn't been here before. So tonight, I want to show you what this place is about," he followed, handing her a glass of red wine before excusing himself to go to the restroom.

Lisa Bailey looked around at the women in different shapes, sizes, and hair colors; some all-natural, some enhanced, and all in a variety of clothing types chatting with younger and older men.

Some women and men in separate groups, some singles, some intimate, and a few looking like she did when she came here the first time.

As she stood at the bar, four to five young men approached her, noticing two things, first, she was alone, and second, no ring on her finger.

Each one was unique in their pitch. One was flirty and another was touchy. Two of them were somewhat timid while the last one was too confident with no substance.

Ms. Bailey was shocked, yet she continued to turn down this flurry of horny, young men. Her body felt hotter and hotter with each advance made.

Just as she was starting to worry about Tanner as she did with Mark the night they were at the club, her date arrived behind her.

"Sorry about that, the line was long for the bathroom," Tanner told her.

Ms. Bailey leaned back into him, implying that she didn't want to be separated for the rest of the night. She felt the young man press behind her as he leaned in to whisper to Lisa, "Check that out, looks like that little guy is shooting his shot."

Lisa Bailey watched as a very young man was chatting up a woman who was Lisa's age. The warmth of her contractual partner and alcohol now tingled in her mind.

The sexy brunette continued her gaze at how the young man touched the mature woman. His hand on her hip, and his body pressed against hers as they talked.  

Tanner continued to watch them also, speaking in Lisa's ear, "I bet she's going to suck his cock tonight."

Ms. Bailey closed her eyes, and the thoughts of that woman's lips wrapped around the young man's manhood briefly flashed in her mind. Lisa felt as if she could hear the throbbing between her legs.

When she looked in the direction of the couple again, Lisa saw the laughs and playful touch of the mature woman.

The young Calhoun hugged her tighter, his member pressing against her dress-covered rear.

"Don't be jealous of her, you get your own young man tonight," Tanner told Lisa. As his warm breath touched her skin, the mature woman felt her loins in a nearing burning state.

Ms. Bailey inhaled deeply, her thoughts drowned out the music in the space.

"I'm ready to get back home, what about you?" Tanner asked, getting immediate acknowledgment from Lisa.

They exited the venue and waited for his truck. As they stood there, the couple could feel the sexual excitement bouncing off each other.

Once she was helped inside the truck, Lisa found herself resting, her eyes closed as her mind was now spinning.

Tanner watched and let her rest, knowing that they were in for an eventful night.

Parking at the back of the house, Tanner Calhoun walked to the passenger door of his truck. His cock was semi-erect as he thought about the busty beauty's tits, mouth, and pussy.

He opened Lisa's side of the vehicle and admired her momentarily before helping her wake up.

Ms. Bailey opened her eyes, unaware of where she was briefly.

"Let me help you out sleeping beauty," Tanner told her, holding his hand out.

Lisa took his offer, and he guided her down from the truck. Ms. Bailey balanced herself up against the truck. Once more, the mature woman took a deep breath, this time to gather herself.

Up against the truck, Lisa looked at Tanner, a drunken lust in her eyes as she pulled him close, kissing the young man, sloppily.

Caught off guard, Tanner regained himself and started to make out with the busty beauty. The warmth from their embrace helped Lisa momentarily, getting her focused on the man in front of her.

Just as her hands reached between them toward his groin, Tanner suggested that they go inside. Lisa took a deep breath before giving her hand to the handsome young man to lead her.

And he did just that, helping guide Lisa to his bedroom. Just as they stepped inside, Lisa Bailey quickly made her way to the bathroom, she had overdone the liquor. The young Calhoun heard her and knew that the night was shot. Instead of feeling remorse toward the lost evening, he knew that if anything, it gave him a little more leverage if necessary.

"Lisa, are you okay?" he asked on the other side of the bathroom door.

Seconds later he heard the toilet flush and the door unlock. Her mascara was a little smeared and her face showed a woman far too gone. Tanner helped her to the bed, taking her heels off and allowing her to rest.

"Get to sleep," he told her.

"I'm swor... I'm so sorry," she said slurred.

Tanner kissed Lisa's forehead and turned the lamp lights off before leaving the room. Downstairs, he sat in the living room and watched TV for about thirty minutes, thinking about what he may want to do the next day. About fifteen minutes later, he got in his truck and left the house.

Once he made it back home, Tanner had a small shopping bag which he took up to his room. Placing it in his closet, the young man noticed Lisa sleeping soundly. He changed and laid down next to her.

Early the next morning, Lisa shifted in the bed, one hand was between her legs. In her spinning head, One of the young men who'd hit on her was fucking her as she sucked another. Ms. Bailey rubbed her pantyhose-covered sex vigorously as the two men in her dream were satisfying her. Her drunken orgasm immediately consumed Lisa and she woke up.... weak, and hungover.

Groggily, Lisa looked around the room and then turned to her side, seeing Tanner. She sighed, rubbing one of her eyes as she tried to recollect the events of the night before. Ms. Bailey had defaulted on her end of the deal with the Calhouns. Rolling to the other side, she slowly got out of bed and went to clean up.

The warm water from the shower helped sober her up temporarily. Lisa changed into some casual clothing and made it downstairs. Benson was cooking breakfast.

"Hey Benson, good morning," Lisa said to the older man.

He turned around, smiling at the mature brunette, "Good morning Lisa. How was your night?"

"Well... I uncharacteristically got drunk..... So we lost the night, unfortunately," she answered.

"Oh no... Well... One moment, I have what you need," Benson replied.

Benson Calhoun handed her a glass of water, some pain relievers, and fruit.

"Take this throughout the day and I think you should be good for tonight," he told her.

Lisa thanked him, drinking the water immediately while also taking some of the pain relievers.

She went to sit on the couch in the living room and made small talk with Benson as she waited for Tanner.

A few hours later, Lisa was greeted by Tanner Calhoun.

"Rough night for you Lisa, are you okay?" he asked.

Lisa smiled in his direction, making eye contact with the young man.

"Ugh, yes it was, I'm so sorry Tanner," she told him.

"Hey... It's okay... We can figure something out. Anything you want to do today?" he followed.

Ms. Bailey couldn't think of anything she wanted to do so Tanner gave her a chance to relax. His only caveat was that he was going to provide her with what she needed for the evening. Lisa agreed to his proposal and was given the huge house to herself for most of the day.

Instead of going around the house and looking at things, she stayed where she knew, Tanner's bedroom, the living room, and the kitchen.

As the late afternoon showed up, Tanner made it to the house with a few shopping bags. He made his way up to his room and noticed that Lisa was taking a shower. The young Calhoun laid out what he wanted her to wear on the bed and went to a guest room to get ready.

Once Lisa got out of the bathroom, she noticed the bed with women's items scattered. Ms. Bailey went back into the bathroom, ensuring her elegance was top-notch tonight.

Her date heard the sounds of high heels coming down the stairs and toward him, just like the night before. He watched in the direction of the clicking, getting an eyeful of the busty goddess as she came closer. Ms. Bailey was wearing a bebe, black, puff-sleeve sweater dress. It was made of mainly spandex with sequin sleeves. The shortness of the dress showed off the mature woman's smooth, bare, sexy, long legs.

On her feet were some black YSL Debbie platform sandals with a square toe and crisscrossed straps, featuring a covered stiletto heel. The satin crepe heels were nearly five and a half inches in height.

The light makeup on her face once more accentuated the mature beauty's best facial features. Lisa's shoulder-length hair had a side part.

Licking his lips, Tanner knew that she was a treasure for any man. His cock was feeling the anticipation as well.

"So where are we going?" Lisa asked, glad that he didn't have her wearing something super revealing.

"Dinner and maybe something simple like mini-golf," he told her.

"Sounds great! I may keep it a little light on the drinking though," she replied.

Tanner laughed and let her know that was fine. Before they both got to his truck, he posed a question, "Did you get the device thing on the bed also?"

"Um, sorry.... I don't think I did," she replied.

The young man quickly ran upstairs and came down with a box, handing it to Lisa. The guest bathroom is there, go ahead and get this on. Ms. Bailey quickly looked at the box before taking it into the bathroom.

Once she had a moment to analyze the item, she realized that he'd bought a small vibrator. Ms. Bailey unpacked it, reading the instructions and clipping it to her panties. Not only was the underwear a little snug to begin with, but with the device, it was even tighter and pressed the vibrator against her intimates.

Lisa spent about fifteen minutes getting this in place with the provided instructions before stepping out.

"Uh, okay, I think I got it, Tanner," she told him.

The young man smiled and held out his phone. Ms. Bailey waited, thinking he was checking a text or a call before she felt a shock between her legs. It was the vibration of the small device. Lisa placed a hand on his shoulder as she bent over slightly and squeezed her legs together. This caused the toy to press against her sex further.

Tanner shut it off and put his phone away, "looks like it works, great!"

He led Lisa to the truck and then they went to eat dinner. Her already dripping pussy was now being manipulated toward streaming.

"So that little device.... Let's say that is part of what you owe for last night, deal?" Tanner mentioned as they drove.

"I understand," Ms. Bailey replied quietly. She wasn't sure how she was going to handle this between her legs. But she did know that she was not in a negotiating position currently.

At the restaurant, the conversations were light, fun, and engaging. Tanner would periodically turn the vibrator on at different speeds. Lisa's pussy was now gushing and they hadn't even had their food yet. Her loins were stirring, near overdrive of excitement.

As they ordered, Tanner let the vibrator go longer to the point that Lisa gripped the edge of the table, her knuckles white, and breathing visibly rapid and deep.

She looked at him, her eyes begging for him to turn it off. Lisa felt she was going to have a loud and attention-driving orgasm in the middle of the restaurant.

Ms. Bailey squeezed her legs together for a second more before releasing the pressure on the toy, shifting to try and minimize the overwhelming sensation.

"Tanner..." she said in a whispery tone. Lisa bit her lower lip as Tanner finally made eye contact with her, shutting off the toy.

Shifting in the chair some more, Lisa felt her body slowly come down from the mixture of pleasure, excitement, and fear.

"That thing is a problem," she told her date, requesting a glass of wine now.

"It seems kinda fun," he told her with a youthful-like smile.

They continued, and as their food arrived, Tanner continued small pulsations during the meal. The sexy brunette had many moments during the dinner where she wanted to tell him that it was time to go home so they could fuck. Lisa was done with the foreplay and her need to get to a release was growing more and more.

The final thirty minutes of dinner kept her on edge, leaving the meal as an afterthought.

Once he paid, the couple made it to the truck and Tanner led them to a miniature golf venue. As much as Lisa didn't want to do this, she complied, not wanting to cause additional problems for the agreement.

On the way there, Tanner had kept the device on, but at a low level. Because she was sitting, Lisa was feeling the gentle massage between her legs. Her wetness felt like a flood, her nipples painfully strained against the dress, and her urges trended dangerously toward willing actions of public debauchery.

He noticed that Lisa was allowing him liberties that he didn't really expect. After parking, Tanner helped Lisa get out of the truck and they made it inside, getting their putters and golf balls.

At the first hole, the young man pulled out his phone and increased the vibration as Lisa lined up. Her legs stiffened as she felt the toy come to life. Ms. Bailey took a deep breath to gather herself. She knelt to place her ball, standing up slowly. Because of her heels, the putter was lower than it would've been otherwise.

From his vantage point, he watched the sexy woman bend at the waist to where the putter could touch the ground. He eyed her flexed calves and thighs. Her ass challenged the back of the dress as it tightly hugged her rear. Tanner felt his cock stirring at the thought of getting behind her, driving his rod into her motherly sex, spanking the mature woman as he fucked her hard. Although difficult for the brunette, she made it through the first hole, unsure of how she would get through the rest of the course.

Meanwhile, Lisa's date was feeling like a young boy with a new toy and was using it as such. The second and third holes were similar, with Tanner turning the device on as Lisa stepped up to putt.

On the fourth and fifth holes, the young man turned up the pressure more, doing this for the sixth and seventh also.

Lisa couldn't concentrate and was hoping to get done with this soon. She noticed that at times, random women, men, and children, all looked at this fancy-dressed woman here at a family-friendly venue. Lisa felt that eyes were watching her with this young man, judging her in every which way.

The thoughts of the judgment and the desire for release kept bouncing back and forth in her mind as Tanner left the toy on through the eighth and ninth holes.

As they made it to the back nine, Lisa whispered to her date, "Can we turn this thing off while we are here?"

He did, letting her know that it would get another chance. Ms. Bailey nodded in agreement, just as long as she was given a moment to gather herself.

For the next few holes, Tanner kept the vibrator off. With three holes remaining, the young man turned it back on. Ms. Bailey sighed, she knew it was inevitable, and she did her best again in the stiletto heels to putt. Getting through the sixteenth, Lisa took a deep breath, gingerly walking toward the seventeenth hole. She felt people could see the wetness dripping down her thighs now.

As she lined up to putt, Tanner turned on the device to a stronger setting and set it to pulsate. Lisa jumped slightly, looking at the young man who was smiling at her as she tried to regain her composure. Ms. Bailey's first shot hit an obstacle and knocked her ball off the course into some landscaping nearby.

When this happened, Tanner turned the pulsation off and dialed the toy up to its maximum setting. Finding her ball, Lisa knelt to gather it. The pressure from this caused the toy to press tighter against her sex, nearly causing her to lose balance. Ms. Bailey got her ball and went back to the hole.

The busty beauty knelt to place the golf ball, and once again the toy stimulated her with more force. Tanner eyed her chest as she lined up, noticing the indents her nipples had now made during the evening.

It took Lisa a few more strokes than she wanted, but she made it through the hole. The only problem was that her orgasm was close and she looked at Tanner with the same pleading look as before.

He lined up his turn and took a few additional strokes himself to get through. Lisa stood, hoping that there was something she could lean on to allow some help as this toy drove her body closer to bliss. Ms. Bailey tried to squeeze her legs, shift her stance, anything to take her mind off what was happening.

But her body was inching closer and closer to what was desired and needed, even if it was in public.

When they got to the final hole, Lisa felt Tanner wasn't going to turn the toy off. And because they had made it so quickly, nobody was at the hole prior. Her breathing was more rapid and her release was almost here.

"Let me help you with this one Lisa," Tanner said.

Ms. Bailey nodded and felt the young man line up behind her, whispering in her ear, "Go ahead and cum, let your orgasm happen, get all of that tension out and feel your release. I'm right here for you."

Lisa closed her eyes, noticing the touch from the young man on her hands as they lined up. Feeling his groin, Lisa Bailey stood back up, pressing herself back onto him.

"There you go, let it go, let yourself get to that pleasure. Don't you need it?" he followed.

"Ah," she moaned.

Her breathing sped up more, and she felt it, the currents as if they were leaving the electronic device. Lisa pushed her ass back into his groin further, her mouth open, eyes closed, and dignity, well... still intact according to everyone but maybe her.

Lisa sexily rotated her rear against Tanner's clothing-covered manhood, grinding on the young man as the tension in her body continued to escape in waves.

When she opened her eyes, Ms. Bailey noticed that the device had shut off.

She tried to gulp air down her dry throat, her body on fire but also in a state of relaxation. Lisa was in some sort of oblivion between needing more and feeling satisfied.

"Last hole, or is it....?" Tanner said laughingly.

Lisa looked at him, her eyes hazy from the aftermath of the release. She summoned up what she could to get through the final hole of the course. As they made it outside, Tanner turned the toy back on. With her body nearly purring immediately, Lisa spoke to Tanner, something she could've never imagined saying to him before, "Can we go home now, please?"

Tanner Calhoun nodded that they could and smiled internally as they started to drive home, ready to enjoy this beauty. Once they parked, the young man helped her out of the vehicle. He immediately pinned her up against the side of his vehicle, the force making Lisa moan gently.

Kisses from her young hung stud serenaded her dainty neck. The soft touches from his lips mixed with the toy that continued to vibrate caused her to forget where she was, momentarily.

"Let's get inside Tanner," she was able to whisper even though her hands had undone the clasp of his pants.

They walked inside together and made it up the stairs, making out along the way.

As they passionately entered his room, the two of them were on each other like long-lost lovers.

Their tongues dived deep into each other's mouths, their moans and aggression almost animalistic. Tanner Calhoun pulled the sleeves of Lisa's dress down. Her boobs released from the tight material, but her arms were pinned. With the top of the dress below her tits, Tanner Calhoun hungrily sucked and kissed her beautiful bosom.

Lisa moaned, throwing her head back and closing her eyes as her nipples were bitten, pulled, and licked.

The young man squeezed her tits together, continuing his affection for them.

"Suck my nipples," Lisa told him.

"You have the best tits I've ever seen," he told her before going back down on them.

Quickly, the young man disrobed, standing fully naked in front of the mature goddess.

Lisa looked down at his already erect cock. She hadn't noticed this before, but he had a slightly longer than average shaft, normal girth, and was completely groomed.

Her mouth watered as she admired his manhood before her attention was diverted. Tanner led the arm-bound beauty to the left side of the bed and opened his dresser drawer. In there, he pulled out a blindfold.

"Let's both put these on," he told her. Without arguing, Lisa allowed this, willing to comply if her needs would be served.

With a blindfold on her eyes, Tanner helped Lisa sit down. What she didn't know was that he decided not to put one on. The young Calhoun positioned his cock toward Lisa's lips.

Ms. Bailey aggressively kissed and licked his shaft. The toy had done what Tanner wanted it to do, but he was unware as to what level Lisa would need to feel satiated.

"God you suck a cock so good," Tanner moaned, encouraging Lisa to continue.

The hungry brunette felt his shaft caress her cheek as she pulled her mouth off of it momentarily. His cock bounced side to side from the pressure of her lips and tongue as she chased his cock with her mouth. A few minutes later, Tanner helped Lisa lie on her back, on the bed.

With the dress bunched up at her waist, Lisa felt her panties being pulled off. Her wetness was ample which the young man noticed by how soaked the underwear was. Instinctively, she seductively spread her legs, hoping that his cock would soon take the invitation.

Seconds later she felt Tanner's lips as he kissed her soft, smooth inner thighs. He made his way toward the mature beauty's clit, causing her to moan loudly.

"Oh fuck!" Lisa screamed. Her inhibitions lowered to a point of complete depravity.

The young man licked and sucked Lisa's pussy, her honeypot overflowed with excitement. Because of the earlier vibrator, Lisa felt another orgasm erupt within minutes of Tanner orally pleasuring her.

Tanner continued to explore the sexy woman, kissing her legs, chest, and abdomen; as her mind, body, and soul pushed toward a sexual state she was starting to unknowingly embrace.

Benson Calhoun had heard the noise of the couple when they'd come home. He was too interested in his wine and cigar to care. Right as he made it up from the wine cellar, the elder man heard a scream from Tanner's room.

He trusted his son and knew who he was with, but as a father would, he wanted to ensure nothing was wrong. Benson slowly and quietly made his way up to his son's room.

The silence as he walked up the stairs was a little worrisome, but as he made it closer to the door, Benson Calhoun heard the panting and moaning from the busty brunette.

Tanner had left the door open, which Benson gently pushed to take a peek inside the bedroom.

His cock started to stiffen from what he was seeing. Ms. Bailey was lying across the width of the bed currently. Her legs bent at the knees, and her nipples were pulled painfully by Tanner as his cock stuffed Lisa's mouth.

A muffled moan from Lisa broke Benson from his trance, causing him to accidentally push the door open more, and catching Tanner's attention. Lisa coughed, gagging on the young man's cock. Her moans indicated to him that she wanted more of the length which was challenging her throat.

The young man pulled back, releasing her buds as she caught her breath. Lisa's blindfold and hair were both a little wet from her saliva. Tanner made eye contact with his father, quietly waving for him to come over.

Benson Calhoun, almost in a trance walked toward his naked son, unaware of what was to come.

Once he made it to the edge of the bed, he saw the long-legged brunette's body in full view, lying in a sexy and alluring manner. He admired her womanly long legs partially bent. The stiletto heels on her feet pressed against the bed as if attempting to puncture the mattress. Her nipples were puffy and erect as if the angelic beauty's buds were a compass, pointing toward the heavens.

Benson looked at Lisa's face, noticing that she was trying to find his son's cock, almost in a possessed manner.

Tanner looked down, the length of his shaft going from the sexy woman's forehead to her nose. Lisa quickly stuck her tongue out, making contact with his member, moaning in frustration as she couldn't get it in her mouth.

The young Calhoun, looked down at her big tits, twisting her nipples and pulling them aggressively.

"Ah!!!! Fuck!!!!" she screamed, arching her back from the pain and pleasure.

Benson looked at her hands, noticing that she was rubbing her pussy vigorously while fingering herself as his son was treating her so aggressively.

Seconds later, Tanner stepped away, waving for his father to take his spot. With some brief and quiet head nodding in agreement and conflict, Benson took his trousers off quickly, replacing his son's place near Lisa's head.

While this was happening, Tanner was still playing with Lisa's boobs to ensure the brunette didn't feel too much of a void. Right when she felt the warmth of a cock near her head, the thirsty brunette attempted to satiate her desires.

Benson closed his eyes as Lisa licked his shaft with a guttural grunt. Even when they embarked on intercourse, he couldn't remember her being this way.

The elder man replaced his son's hands with his, pawing and massaging Lisa's big tits.

Ms. Bailey moaned, unable to distinguish the different touch, too consumed by her desires.

Quietly, Tanner positioned himself between her spread legs, quickly climbing on the bed and slamming his rod deep in her wet pussy.

"Oh fuck!" Lisa screamed, turning her face to the side. She attempted to reach up with her sleeve-bound arms toward the man near her head, surprised yet unwilling to protest.

Tanner rapidly pumped in and out of the sexy woman, bringing her stirring feelings to a higher state.  Ms. Bailey brought her arms back down, rubbing her clit as she felt the penetration from Tanner Calhoun.

Lisa Bailey grunted and moaned as the young man fucked her hard. Once she felt his rhythm build, the blindfolded beauty moved her head back to where she was facing upward.

She felt Benson Calhoun's cock graze her nose. Due to the sexual state she was in, Lisa licked at it as she tried to take the mature man's cock in her mouth. Seeing her do this, Benson pushed down on his shaft, helping the busty beauty toward her want, or more so, need.

Lisa Bailey had only dreamed of what she was currently experiencing. A cock penetrated her honeypot while another fed her hunger.

Feeling tired from shifting her neck back and forth, Lisa stopped her movement.

Immediately Benson started to thrust back and forth, giving her more of what she needed. Ms. Bailey swirled her tongue along the hard cock that penetrated her warm mouth.

As the double-stuffed brunette felt the two men thrusting in and out of her, Lisa

Bailey's body quickly shot toward an earth-quaking orgasm.

The two men watched as she looked like a woman going through some type of exorcism. Thrusting and gyrating, moaning and groaning as each wave of pleasure rolled from her toes, up and through her sexy body. She had moved her mouth off of the mature man's shaft as this happened, panting for air.

Momentarily they paused, letting her come down from her lengthy release. As her breathing finally normalized, Tanner started fucking her once more, and Benson moved his cock toward her wide-opened mouth.

An animalistic grunt escaped her mouth again as the young man's shaft penetrated her pussy. The sexy woman wrapped her mouth around Benson's cock, sucking his manhood tightly.

Due to her state of arousal, Lisa didn't notice their size or girth, she just needed the penetration from the men to pleasure her mouth and pussy.

Tanner stopped fucking her after a few minutes, pulling his cock out and eyeing the void it left behind. As if it had a life of its own, her pussy looked to be breathing as her hole looked back at him, invitingly.

Seeing his son stop, Benson also pulled out, waiting for direction, unaware of what to do. The young man signaled for his dad to swap him places. The mature man went to the other side of the bed. They both watched Lisa sexily moving on the bed, still looking consumed by her sexual urges.

"Turn around on the bed, I'll help you," Tanner whispered in her ear. Her dress still had the brunette's arms restrained.

The mature beauty followed his touch, finally ready in their desired position. Lisa was on all fours, her pussy dripping on one end, while her mouth salivated on the other. She could feel excitement throughout her body as she waited in anticipation for what was next.

Benson positioned behind her, touching her soft, motherly rear as he pressed his cock inside her. Lisa gasped, leaning back to let him know he was welcomed.

She moaned as Benson's cock dipped deep into her honeypot. The blindfold was still on, and Ms. Bailey still couldn't see in front of her at the moment.

Lisa continued to face forward, feeling Tanner's lips touch hers.

The young man kissed her deeply, the feelings of the moment and excitement all playing a role in his lowered awareness.

Lisa's tongue danced with his as she felt a deep sensation from the passion. His hands grasped the sides of her head to show how strongly he felt about her actions.

The kissing continued until it was Lisa driving deeper into his mouth. Breaking free from her grasp, Tanner then pressed the head of his shaft toward her lips, immediately feeling her wet warm mouth engulf his erect member.

Anyone who would've entered the room would've seen the mature beauty on the bed, on all fours in high heels, being plowed from behind by a father, while she sucked off his son.

Her tits swayed slightly, nipples hard and yearning to be pulled as each thrust from Benson drove deeper and deeper into her sex.

Lisa was sweating from the intense session, her hair started to get wetter as her mind transitioned through a sexually euphoric state.

After fucking like this for a few minutes, Tanner and Benson swapped positions. The young man again slammed his cock deep into the mature beauty's sex.

"Mmf!" Lisa let out a muffled moan. Her mouth was already stuffed with Benson's cock.

Tanner Calhoun fucked her hard and fast, spanking Ms. Bailey's mature ass. Lisa was aware that she was getting two cocks, but awareness was a minor detail. Her sexual satisfaction had overtaken her mind. The ability to feel one form a pleasure in her pussy while another with her mouth was overwhelming.

She moaned and grunted, her ass cheeks, red from the spanking, jiggled with each thrust. Feeling himself near an orgasm, Tanner reached forward, grasping her hair in his hands. The movement caused Lisa to pull off Benson's cock and lift the blindfold to her forehead.

Benson watched as she faced him now, looking into his eyes with her mouth open, begging Tanner for more.

"Ah... ah... ah... yes... fuck me.... fuck my pussy.... fuck yes!" she screamed in a wonton-like delirious state.

The strong young man continued, plowing her until his seed shot deep inside her womb. Lisa felt her body react to the feeling, shuddering as another orgasm shot through her body like fireworks.

Benson Calhoun watched her while he stroked himself to his release which landed on the bed.

Tanner had already let go of her hair when he came. Lisa leaned forward, her pussy coming off of his cock. She lay on the bed with her arms still contained by the dress. Her hair and cheek resting on the cum that Benson had released moments before.

With her legs slightly spread, Tanner eyed her pussy, his sperm leaking out of the mature woman's well fucked hole.

Benson quietly left the room and went downstairs to clean up.

He was surprised by his son's actions, but very surprised that Lisa had allowed this to happen. She seemed very sexual but he didn't expect her to be willing to do things like this.

In the bedroom, Tanner went to wash up as he noticed Lisa had fallen asleep.

As she dreamt, Lisa was on her back, naked, and a cock was in her mouth and pussy. Ms. Bailey didn't see faces, just felt and tasted the two cocks.

She continued to allow these men to have their way, or more so, Lisa was using them to satisfy her urges.

On the bed in Tanner's room, Lisa had turned around on her back and was rubbing her swollen mound. Tanner Calhoun's sperm and her juices mixed on her fingers as she once more played with her pussy.

The young Calhoun came back to the stacked brunette, touching herself.

"God damn," he thought to himself as he continued to watch.

Tanner couldn't remember a time when a woman was this aroused. His cock started to come to life again, and he walked over to where her feet were.

Ms. Bailey was moaning and breathing heavily as she continued. Within seconds of getting by her legs, Tanner swiftly grabbed her lower legs, pulling her towards him.

Lisa yelped from the force, cooing as his semi-erect cock pushed her fingers aside and nestled in her pussy.

The hot woman wrapped her legs around his lower back, bringing him in closer. Tanner bent forward from the pressure. When she felt the heat from his body near, Lisa reached up for him, touching his body until her bound arms struggled to find his head and bring his lips to hers.

Ms. Bailey kissed him deeply, moaning in lust as he started to slowly fuck her. Tanner Calhoun released his mouth from hers, kissing Lisa's neck and ear.

"Mmmm....," she moaned in a sultry tone.

The handsome young man could taste the saltiness on her body from the sweat of the session. Meanwhile, Lisa's hands roamed his back, grabbing his rear, implying for him to drive deeper into her pussy.

They were both tired, but continued on due to the state of mind their evening had brought them to.

Tanner rested on Lisa for a moment before hearing her speak, "Lay down so I can fuck you."

Removing the dress from Lisa's body, Tanner lay on the bed and watched as Lisa eyed him, staring at the young man as if he were her prey.

Once she mounted herself on him, Ms. Bailey gyrated and grinded her pussy on his cock, stirring his member back to a full erection. Lisa grazed his fit young chest with her manicured fingernails, moaning and cooing as she slowly fucked herself on his shaft.

Her hair was a mess and her body well fucked, yet her desire for more was still unsatisfied.

Even though he'd just released, the way Lisa was grinding on him caused Tanner to ejaculate within minutes.

"Fuck Lisa, I'm cumming again," he told her somewhat remorseful.

She looked down at him, unfazed as she continued with a devilish smirk on her lips.

Ms. Bailey leaned down and kissed the young man before asking him to suck, then pull on her nipples. Doing this for a minute helped tune the busty beauty toward another orgasm.

The motherly brunette cradled Tanner's head as she came down from another release, this time seemingly done from the marathon of a night.

"You are one sexy woman," Tanner whispered in her ear.

A low moan emitted from her as she pressed her chest down on his before lifting off of the young man. Momentarily she lay next to him, her mind still yearning for more. But Lisa's body was ready to stop for the night. She was exhausted from the multiple orgasms, even though her sex was showing visible signs of excitement.

Ms. Bailey lifted herself off the bed, momentarily stumbling due to the heels she wore. Lisa sat back down to take them off. She then made it to the bathroom, leaving the lights off as she washed her body.

Meanwhile, Tanner had fallen asleep now, almost satisfied with his agreement with Lisa Bailey.

Once the mature woman made it back, she lay next to the handsome young man, falling asleep almost immediately.

The morning light woke them both up within about thirty minutes of each other.

"What a night," he said, yawning and stretching his arms.

Lisa looked at him, rubbing her eyes as her sore naked body shifted in the bed.

"Yeah, it sure was...," she replied, unsure of what to feel.

They engaged in some small talk before making their way downstairs separately. There, Lisa asked Tanner if there was more to do today and he told her that she could go home.

Once Lisa left, she drove home, thinking about the night.

Meanwhile, Benson met Tanner in the kitchen.

"Do we plan on doing that again?" he asked the young Calhoun.

"Man... Dad, I don't think so but I didn't think that would happen," Tanner replied.

"You think we could use her services for another deal?" Benson asked.

"Yeah, I do. She and I haven't technically finished our deal yet," Tanner followed.

"Well.... You know that one guy? Maybe we can get something favorable with him, what do you think?" Benson Calhoun stated.

Raising his eyebrows, Tanner responded, "Maybe...."

"And dad.... I also haven't deleted the video...," Tanner shared.

The father and son looked at each other with thoughts of possibly utilizing Lisa Bailey's skills for their benefit further.