Starting Over

[BeachBum25]

Michael loved just how forward and confident Emma was. There was nothing that she was afraid to do. He wasn't sure if that was because of how wealthy she was, or if she was wealthy because she was that way. Either way, he liked it..... a lot.

He listened to Emma conducting business with Heather. He watched as Heather switched her weight from one leg to the other. Michael saw Heather fingering her wedding ring as she was running what Emma had said through her mind.

Moving close to Emma, Michael put a hand on her back and caressed it lightly. Smiling at Emma, and then looking at Heather, "Oh, and there is one stipulation to the deal...... Emma gets to watch the whole interaction... from beginning to end."

 

[wickedpen]

Heather looked at Michael in a different light now as she pondered this illicit adulterous proposition. To be honest she had not had a good fucking in months, since her husband lost his job and Michael was attractive.

Heather looked at her watch, then at Michael, bit her lip and then at Emma. "OK" she said, "a few ground rules though. Two hours and no one else can ever know. And oh yeah, I want cash." Heather looked confident, not like someone who was agreeing to sex for money for the first time.

Emma smiled and said "Oh good" as she brought her hand up to Michael's crotch and felt his hard on. "I think we have a deal" she said beaming up into Michael's eyes.

 

[BeachBum25]

Michael watched Heather’s reaction and he was surprised at how quickly and easily she agreed to Emma’s proposal. He was intrigued about how quickly she was able to demand cash for the transaction. It made him wonder if she had done this before.

He put his arm around Emma as she reached down and grabbed his crotch. The thought of fucking Heather had him hard, and it seemed that Emma was happy to see and feel how hard his cock was.

“Well, Emma, it seems that Heather has put a time limit on things. I think that you should work out a deal where you get some money back if Heather wants to extend the session beyond 2 hours. Either that, or there should be some other form of payment to you.”

 

[wickedpen]

Heather shifted her weight to her hip and said "I woldn't worry about that honey."

Emma beamed.

"Where shall we begin?" Heather said as she began to pull her blouse from her tight skirt.

 

[BeachBum25]

Michael looked at Heather out of the corner of his eyes. She definitely was full of herself. He nodded at her. Her husband certainly had his hands full with this one. There was no doubt in his mind that she had strayed once or twice before.

He turned to Emma and took her in his arms and kissed her deeply and passionately. When they broke the kiss, he whispered to her, “You are amazing. I need you to teach me how to negotiate the way you do. However, I may have to break this one.”

Turning back to Heather, he pointed at the pool. “Would you like to start there, or would you prefer to start in the hot tub? Either one works for me.”

 

[wickedpen]

Heather stripped her blouse, and skirt and walked naked, calmly to the pool and slid into the water head first. She came up standing deep enough that her breasts were underwater. Her hair was slicked back and she moved her arms feeling the water. She was more excited about this than either of them but was cool.

"Sett he clock Emma" Heather said with a hint of tease.

 

[BeachBum25]

Michael smirked. Either she was cool as could be and experienced in taking money for sex or she was a great actress who was excited about what was about to happen and was able to hide that excitement. Or maybe a little of both.

He turned and faced Emma and began to undress. He maintained eye contact with her as he removed his clothes and dropped them into the deck of the pool. He smiled at her and whispered, “I hope that I put on a good show for you.”

Turning around, Michael walked to the edge of the pool and sat down with his legs in the water. He could not hide his arousal and he saw Heather checking out his big, hard cock. Then, he slid into the water and swam to the other side. Coming up, he called to Emma, “I wonder if it will be enough time.”

 

[wickedpen]

Heather swam over having heard Michael's comment to Emma.

"I guess we better get started then" Heather said as her hand wrapped around Michael's hard on with a soft moan. "You like performing for Emma?" she asked with a cool eye. Squeezing and stroking she sighs "I will play my part."

 

[BeachBum25]

“Your part will be to perform for Emma and to perform for me. Performing for Emma would be a wise career decision. Performing for me will be a wise personal decision, because you will enjoy the pleasure I can bring to you.”

Michael cupped her breasts and began to caress them as he looked into her eyes. He rolled her nipples between his fingers as he turned her so that her back was against the side of the pool. Her tits were amazing. He certainly was going to enjoy them as well as the rest of her hard body.

He leaned in and kissed her neck as he continued the attention to her breasts. He kissed and nibbles up her neck and then back down her neck to her shoulder. Despite the time constraints that Heather had put on their encounter, he was in no hurry.

Moving his hands from her breasts to her hips, Michael lifted Heather out of the pool and sat her on the deck of the pool. Her legs were hanging into the pool, and he spread them wide as he moved between them.

He licked up her inner thighs until he found her silky pussy. He dragged his tongue flat over her pussy and finished with a flick of her button. He repeated this. Then, he parted her pussy lips with the tip of his tongue and began to explore her folds. His hands keeping her legs spread wide.

 

[wickedpen]

Heather felt exposed now on the coping of the pool but also incredibly turned on. She looked at Emma now seated on a chair watching with a bemused smile on her face. She licked her lips as Heather felt Michael kiss his way between her legs. She held Emma's stare until his tongue met her clit. She instinctively moaned and threw her head back. He was amazing and it had been years since Heather had had this type of attention. She raised her hips and moved them forward giving him full access.
"Eat my pussy!" she growled as she ached for more. He was so good, and she had almost forgotten about Emma. Heather reached down and pulled his head into her smoldering crotch.
"God yes! YES!" she cried as long forgotten orgasm rushed towards her.
"I am going to cum!" she panted as her eyes opened and Emma was still sitting, calmly watching. The two women locked gazes as Heather's mouth opened and her body stiffened and she was pushed over the edge into blissful orgasm.

 

[BeachBum25]

He did not pause. Michael continued to eat Heather’s pussy. He licked her wildly through her orgasm; making sure to maximize her pleasure. Michael has no idea what the sexual relationship between Heather and her husband was, but he had every intention of giving her an idea of what good sex was all about.

Once her orgasm subsided, Michael pushed himself up onto the deck; supported by his arms with his legs still in the pool. He pressed his body to Heather’s and kissed her deeply; sharing with her her nectar.

Then, Michael fell back into the pool and helped Heather slide back in with him. He spun her around and pulled her back to him. He wrapped his arms around her and placed his hands on her breasts. While caressing her breasts, he nibbles and kissed her neck and shoulder while his hard cock pressed against her perfect ass. “Your body is amazing and you deserve to be pleasured again and again, Heather,” he whispered to her.

 

[wickedpen]

Heather's head spun as he rose form the water and kissed her with lips drenched in her juices, and it was obscene. Pulling her weightless numb body into the water he wrapped around her as she became keenly aware of the big hard cock now pressed along the crack of her ass. His hand massaged her back into feeling, pinching her nipples.

"Jesus that was good!" she breathed out as she slid her hand back behind her and down to his cock. "Do you want to be inside me?" she asked laying her head back on his shoulder. "Or should I go down on you first?"

 

[BeachBum25]

Michael pulled on her nipples as his tongue explored her ear. He was absolutely certain that he was going to enjoy Heather’s body. He whispered to her, “Just go with it. Don’t try to plan what we are doing. Let how you are feeling guide us.”

He released her tits and guiding her to the shallow end of the pool, Michael took each of her hands in his and placed them on the coping of the pool. His feet spread her legs wider and slid his cock between her legs.

Moving his hips slowly, stirring up the water in the pool, Michael moved his big, hard cock over Heather’s silky pussy. Despite the time restraints she had . put on them, he was in no hurry. His shaft glided along her pussy; the feel of her silkiness making him want her more.

Placing the swollen head of his hard cock to her pussy, Michael slipped inside of her and, in one steady thrust, filled her pussy with his hardness. He paused with his cock buried in her; pulsing his cock. Then, he started to move in and out of her.... long, slow, and deep. “How about we go with this for a while.”

 

[wickedpen]

Heather tried to collect herself but it was all so much so fast. He glided her through the water and his touch became electric as he spread her arms on the side of the pool. She let him do as he wished and that was nothing short of amazing. Sliding into her sent another wave of bliss through her. She would fuck him for nothing but for money it was better than any dream. Her husband wasn't this good on his best day and she had wanted some for a long time. She wrapped her legs around him and watched him watch his cock slide in and out of her through the water.

"So good" she sighed as his hands held her hips in place for his pleasure. He was using her with not even a glance at her and she was fine with that. She tried to work her hips with him but her body was so stimulated each bump or jerk brought another drenching endorphin bath.

"Don't stop, don't ever stop" she moaned as her legs released him and hung limp in the water. "Use me" was the last thing she uttered before a full body orgasm ripped through her as he continued his steady, long strokes in and out of her.

She shuddered as she exhaled "oh god" which echoed through Emma's pool area. Again trying to focus on him she said "let me make you cum, tell me how..."

 

[BeachBum25]

Michael enjoyed how her body reacted to their entanglement. He was pretty sure that she was getting more than she expected. He leaned in and sucked and nibbles on her shoulder leaving a little mark at the base of her neck.

Pulling his cock out of her, he smiled at her. “Get on the pool deck. On your hands and knees facing Emma. I want you to be able to look right at her since she is the one who made all of this happen.”

He followed Heather onto the pool deck and laid a towel out for her. After she got down on all fours, he knelt behind her. Gripping his cock, he slid it along her silky pussy lips before plunging deep inside of her tight pussy in one, long, deep thrust. He felt her body stiffen, then relax. He kept his shaft buried deep inside her... his hips moving in tiny circles.

Moving his hips in long, hard thrusts, Michael began to fuck Heather fast and hard. He reached up and placed a hand around Heather’s throat and gripped it tightly. He pulled her head back to him and whispered in her ear, “You need to make sure you properly thank Emma when we are finished. I know I will.”

Michael kept his hand on her throat as he continued to fuck her good and deep. His thrust got harder... his balls slapped against her as he stretched her pussy so fucking good. Before he knew it he was on the verge of exploding. He thrust his hips harder and faster until he erupted..... shooting giant ropes of his thick cum deep inside of her.

 

[wickedpen]

Heather's head hung down as she recovered from her orgasm and the sensation of Michael pounding then cumming in her. It had been a while and she had really exploded.

"Come here honey" Emma said as she now sat with her skirt up and her leg over the arm of the deck chair. "Show me some appreciation for that magnificent cock" she said as she glanced at the wall clock. "We still have forty minutes honey and I think this is just the thing to bring Michael back to full strength." Emma slid her fingers along her wet lips and circled her clit turned on from the action so far.

 

[BeachBum25]

Michael sat on the pool deck as he watched Heather react to Emma. Heather crawled toward Emma and Michael admired the wonderful view from behind. He was thinking beyond the 40 minutes that were left on Heather’s timeline and wondering how he could get her again later.

He was surprised that Emma called for Heather forward her. Michael thought that all Emma wanted to do was watch. The sight of the two women together was bringing his cock back to life. There was no doubt he was going to enjoy more of Heather today.

With Heather between Emma’s legs, Michael moves in for a better view. He leaned down to kiss Emma as his hand caresses Heather’s Perfect ass. His fingers teased her rosebud as the kiss with Emma became more passionate.

 

[wickedpen]

Emma reached down and squeezed Michael's cock as she enjoyed Heather's oral abilities. She motioned for Michael to bring his cock to her mouth and she began letting him fuck her mouth as Heather licked her clit to ass in the chair.
"you kids are too much" Emma sighed before Michael moved his cock back into her soft wet hot mouth. Michael was delicious with Heather's taste and Heather's tongue was perfect against her clit and Emma was so close. She pushed Michael back and began pumping his cock as she arched her back and pulled Heather into her crotch tight. She looked up at Michael as her hand was like a vice on his cock. Emma's smile turned into an open mouth as she nodded and fought to keep her eyes from rolling back as she looked up at Michael but then gave in and Heather grunted and sent Emma off into complete orgasm.

 

[BeachBum25]

Michael backed away and watched as Heather brought Emma to an incredible orgasm. It was an incredible sight. Heather and her incredible body getting Emma to cum so hard. The sight of what happened in front of him, along with Emma’s hand and mouth had Michael’s cock incredibly hard again.

“Move up and kiss Emma. Let her taste her cum on your lips and tongue.” As Heather moved up to kiss Emma, Michael caresses her ass and moved his fingers teasingly between her firm cheeks.

Moving behind Heather, Michael slid his cock between her legs as she kissed Emma. He slid his hard cock along her pussy and felt her push back a little. Grabbing her hips, Michael pushed his cock into her tight cunt and filled her deeply with one, long, deep thrust of his hips. With his cock buried in her pussy, Michael teased her rosebud as he looked down into Emma’s eyes.

 

[wickedpen]

Heather could only hold Emm's kiss for a moment as Michael's cock returned. She put her face into Emma's large chest as the older woman held her in place as Michael thrust again and again.
"Isn't he wonderful?" Emma sighed looking up at Michael. Heather nodded as she moved to begin suckling the breast next to her face. Emma watched Michael and knew what he was thinking.
"Relax sweet girl" she sighed as her arms wrapped around Heather, as though she might try and leave. Emma watched Michael's spit drop onto Heather's perfect ass and slid down. They both watched as his thumb rubbed the lubricating saliva into her tiny button.
"Shhhh" Emma tried to calm Heather as she tried to stand up. "You need that money don't you?" she told Heather as Michael pulled back out of her and brought his head to her tiny opening.
"Oh I miss being so young and tight, such an object of desire, pure lust" Emma narrated the scene. "Kiss me" she said as Heather lifted her head quickly, obviously nervous and kissed the older woman until her body cried out in response to Michael entering her.

 

[BeachBum25]

Michael pressed the swollen head of his big, hard cock to her tight asshole. Emma narrating added an additional level of eroticism to the entire scene. He saw how Emma was holding and making sure to maintain Heather's focus. He certainly was going to enjoy anything with Emma or that Emma cared to arrange for him.

Pushing his hips to her, Michael entered Heather's tight ass. She was so fucking tight. He wasn't sure if her ass had ever been taken before, but he was certain it had never been stretched the way he was going to stretch it.

He felt her tighten her grip on his cock as he slowly pushed his big cock deeper into her ass. He took his time. He did not want to hurt her, but he certainly wanted her to remember who had fucked her ass so good. He gripped her hips and pulled her ass back to him as he pressed his hips to her; his cock pushing deeper... stretching her tight ass so fucking good.

"Fuck yes. Your ass is so fucking tight. That's it Emma.. hold her right there. She is going to find out just how good it is." He pushed deeper and deeper until he was buried in her ass. He pulsed his cock while it filled and stretched her. Then, he began to move his hips.. in and out... short little thrusts at first... then, becoming longer... deeper... harder.

 

[wickedpen]

Heather tried to relax as the one thing she had refused her husband and every other man she had ever been with was now being done to her and she wanted it. She wanted it but a telephone pole in a mouse hole does bring some issues and she lost her way licking Emma and could only brace herself and groan erotically.

"That's it girl" Emma coached "relax and enjoy my friend. He is certainly enjoying your tight young ass." Emma said enthusiastically. She cupped Heahter's face now with tears running down and Emma's juices coating her jaw line. Once Michael worked past her sphincter things ground into a manageable sensation. She looked up at Emma who was watching Michael until Heather's tongue flicked her clit again and then she looked down smiling bigger.