Starting Over

[BeachBum25]

Starting Over closed for WP

Michael Reilly 28/m
6’1” 180 lbs
Light brown hair
Hazel eyes
Athletic build.

Michael was a math teacher at the high school he graduated from. He was engaged to his high school sweetheart who taught English at the same school. They had everything going for them. They had been highly successful in high school and college and returned home as heroes. They seemed to have the perfect life.

That all came crashing down when the police showed up at their apartment and arrested his fiancée. It seems that she had been having an affair with one of her students. It had been going on for months, and now the boy shared the information with his parents and the police. Michael watched in total shock as she was led away in handcuffs.

Before she was able to make bail, Michael had cleared out of the apartment. He got a hotel room and, when he turned on the television, there was his former fiancée on the news. Everyone in town would know about it. How could he ever go back to school? He couldn’t. He got a doctor to write a note that he was suffering from anxiety. He took a leave of absence. Then he resigned from his position.

Michael needed to get out of town. His parents had moved to Florida and bought a nice place near the ocean. That was before dad ran away with his secretary. Mom got everything in the divorce. Michael decided to visit mom for a while. While there, he interviewed for a teaching position and got it. Mom insisted he stay with her for a while, so, he did.

He enjoyed his new job. He enjoyed being in the Sunshine State and going to the beach. He enjoyed the free time of not being tied down. He enjoyed running in the sun with his shirt off. Mom left him alone.

It was Friday afternoon and he walked into the house. He was surprised to see his mother sitting in the living room with several women. They were all drinking wine and they were all dressed very well. His mother called him over and introduced him to the members of her women’s group. She told him they met once a week for lunch and that they would then go back to one of their houses for drinks.

Michael could not believe how attractive the women were. He had never looked at mature women, but these women were very attractive. One, Carol, he would classify as hot. The others were not far behind. He stayed and chatted briefly before heading off to his room.

 

[slutindianwife]

.........................

 

[wickedpen]

"Amy you did not tell us you had company?" a woman who was sizing Michael up from her perch on the far side of the room.
"Oh this is my son, Michael. I have told you about him" Amy, Michael's mom said stepping next to him and taking his arm. "Handsome right girls? And if you know anybody he is available.." she said much to his unhappiness.
"Hi I'm Carol" the one Michael had already identified stepped forward and offered her hand. She wore a giant diamond wedding ring and several gold bracelets, and that was only on her one hand. The other hand had assorted rings and bracelets as she held her wine.
The oldest of the bunch, maybe late fifties was Emma. She was full figured with an enormous chest and blonde hair and a British accent. "Oh he's a looker" she chimed in.
"Can I get you anything?" Amy asked as her son slipped his tee shirt on.
"Leave it off, we have such little fun" A petite woman his mother's age said from the couch. She was Susan and bleach blonde and tanned as could be. She as five five and a hundred and twenty pounds maybe, with a warm smile and bright blue eyes.
Carol stood near Michael after he released her hand. "So Michael welcome to Florida. Terrible business back home, your mother told me" she said as her eyes took a trip up and down his chiselled young body.
"OK Run along before the talons come out" Amy said glaring at Carol.
"I dodn't mean anything" Carol said retreating back with her hands up and a slight smile.

 

[BeachBum25]

Michael smiles awkwardly. He was surprised by all of the attention he was getting. He had to admit though, it was nice to have that attention from women, even if they were his mother’s friends, and especially from Carol, who was hot and carried herself so well.

He went into his room and removed his shirt and shorts and headed to the bathroom to shower after his run. While in the shower, his mind wandered to the women who had been paying him the compliments. He had never been attracted to women who were older than him before, but now, he found himself aroused at the thought of them.

He took his time in the shower and in getting dressed. He did not want to interfere with his mother’s party. He put on a clean t and a pair of cargo shorts and, after listening to see if he could hear any talking, walked out of his room and into the kitchen to find something to eat.

 

[wickedpen]

"Hi I'm Susan" startled Michael as the woman as suddenly behind him. He looked down on her unable to miss her incredible cleavage worn openly in her low cut flowered dress.

She casually cornered him between the counter and the fridge as she continued to talk.

"Your mother is lucky to have you around" she started as her eyes roamed where they wanted. "Yes she is" she reiterated. "Now you watch out young man, you are a hot commodity in these parts, if ya know what I mean?" she said with a wink and a pat on the hip. She then pushed by him letting his elbow get a good feel of her surprising firm breast as she opened the refrigerator and retrieved another bottle of wine.

"And if you ever need anything" she said before walking away, "I am two door up past the big palm tree."

 

[BeachBum25]

He was shocked to hear the voice behind him. He thought all of the women were gone. Obviously, they were not. He could not keep his eyes out of her cleavage no matter how hard he tried.

He smiled at her. “Hello Susan, it is nice to meet you .” He could feel his cock growing in his shorts. There was no denying that he liked the attention. He extended his hand and took hers in his; holding a little longer than normal.

“So, I am a hot commodity around here? I didn’t realize that there were not that many men around. I guess that means I will have my pick of the litter.” He was feeling bold and decided two could play the flirting game.

“Well, you know where I am if you need anything.” He paused for a second with a wicked grin on his face. “Like a box relocated or some furniture rearranged.... or something else.” He watched her walk away with the wine and poured himself a glass of ice water.

 

[wickedpen]

Michael had hardly reached the top of the stairs and he heard footsteps behind him. Carol was looking back behind her as she followed him.

"Hi Michael" she said with a hushed tone. "I'm Carol" she introduced herself again and again shaking his hand and closing her left hand over the hand shake. She looked into his eyes as she was taller. He took note that her blouse was low cut and fairly revealing for what his mother referred to as a "frumpy old retirement community."

"I just want to tell you your mother is lucky to have you." it was like they were all reading off a script. But then she detoured. "My Jeffery only comes home for holidays and then with his ball and chain wife. It's not like when he was single" she explains looking at him as if to see if he understood. She was still holding his hand in hers as he felt a wiggle and a piece of paper pressed into his palm. "If I can be of any service," she emphasized this with a downward glance, subtle as a wrecking ball, "just give a ring."

She smiled and then turned and head down stairs. She wore a tight skirt around her maternal hips but with a shake that caught the eye. At the bottom of the stairs she looked around the corner then back up at Michael and winked.

 

[BeachBum25]

Michael could not believe what was going on. Two of his mother’s friends had gone out of their way to flirt with him; one had even followed him upstairs. He took the piece of paper from Carol and smiled at her.

His eyes were all over her. She had caught his eye earlier and now that he got an up close view without his mother interrupting, he found her even more desirable than before. His cock grew harder still and he made no attempt to conceal his arousal.

As she descended the stairs, he watched her closely. His eyes moved from her round ass to her hips. He thought about grabbing them and pulling her back to him as he thrust into her. Yes, he had a feeling that he was going to enjoy some personal time with Carol.

Before she went out of his sight, he said to her, “you have a lot of rings, I don’t think you need one from me, but if there is something else you need, you know where I live.” He went into his room; leaving the door slightly ajar so he could hear when the women left.

 

[wickedpen]

Walking in after everyone had left, Amy (mom) walked into his room.
"I saw the door..." her words stopped as she looked at him on the bed. His eyes were closed and he was stroking his sizable cock. She quickly ducked out before he noticed.
Her head raced. She had walked in on him before but many years before. It sent a strange thrill through her but also a sadness that he had a wife to take care of that before. She immediately started trying to think of someone to set him up with.
She called Emma who had lived here the longest and seemed to know everybody and then some.
"Hi Emma is Amy..."
"yes today was fun... uh huh he is cute.." the small talk went on until she asked "do you know anyone who might be interested in Michael?"
She listened and then said "someone his age?" obviously Emma had some older ladies in mind.
Amy hung up and looked despondent as she heard him coming down stairs. She put on a smile and started to make dinner, or at least act like it.

 

[BeachBum25]

“Hey mom. Sorry about crashing your party earlier. I didn’t know anything about you little group. They seem like a nice bunch of women. I am glad you made friends down here, especially with dad splitting for that little tramp.”

Michael walked over and placed his hand on his mother’s hip and kissed her on the cheek. “What can I do to help you with dinner mom?” He waited for an answer, but his mother didn’t look at him. He started to wonder. Did she see something she wasn’t supposed to see?

“You and your friends seem like you have a good time together. They seem like a good time. I am happy that you have been able to connect with them. You seem like you all have fun together. I bet they get pretty wild.” He watched for her reaction.

 

[wickedpen]

Amy was a steaming cauldron of thoughts and images on the inside but cold and calm outwardly as her son, who she just witness masturbating in her guest room, one of the biggest cocks she had ever seen.

"Uhh yeah they are nice" she said almost absentmindedly. She felt like an idiot but it was all so fast. Seemed that since Micheal Sr left she had not even thought about sex and now Michael jr is back a week and it's crazy.

"Ya know Michael, it is a retirement community but a lot of these women are divorced and lonely. You may enjoy spending time with them. Not necessarily anyone in my group but you never know" she said as she peeled carrots for an unknown reason other than to give her hands something to do and eyes focused away from Michael's shorts.

The phone rang as the conversation lagged and Amy picked it up.

"Oh hi Carol..."
"Yes she sounds lovely//"
"In an hour? OK hold on" Amy said and covered the receiver.
"Michael Carol's niece if coming in from DC for a visit would you like to meet her?" Amy said. Without giving him a chance to say no she uncovered the receiver and said "sure, he will be over in an hour. Bye."

 

[BeachBum25]

Michael watched his mother peeling the carrot. Her free hand looked almost as if she was stroking it. Did she see him? She must have. This wasn’t exactly the way he wanted to start his time back with mom.

“Mom, don’t do that. Don’t go trying to set me up.” It was too late. His mother had already told Carol that he would be over to meet her niece. There was a part of Michael that wished Carol had called and asked him to come over and help her with something. He certainly would be happy to help her.

“I am not a teenager that needs to be fixed up with anyone mom. I can handle things myself. I can find an attractive woman to go out with without my mommy’s help.” He stood up and walked over behind her. He leaned in and kissed her cheek from behind. “I will go meet Carol’s niece, but only because I don’t want you to look bad to a friend. From now on, let me handle my love life... okay?”

He went upstairs and changed, putting on a nice collar shirt and a pair of nicer shorts. He kissed mom goodbye, and, after getting Carol’s address, drove to her house. Knocking on the door, he looked around at the well kept front of her house as he waited for Carol to answer the door.

 

[wickedpen]

Carol answered the door with a cocktail glass and a swagger that said she had not stopped since the wine this afternoon.

"Hey there Michael, come in" she said. Her eyes were down his back as he passed and she closed the door. The house was dark and cavernous with stone floors and crown molding. Every room was tastefully decorated.

"Let's go into the living room" she says walking behind him with her hand on his back,.

"here you are dear" she said as they entered a dark p[paneled room that looked more Medieval England than modern Florida. The couch was long and plush deep burgundy and a wooden coffee table. There as a fireplace and a large TV.

"What are you drinking Michael?" Carol asked as her blouse was open another button lower.

 

[BeachBum25]

As soon as she came to the door, he could tell that she had not stopped drinking. He smiled at her and noticed that there was another button undone on her blouse from the last time he had seen her. Her touch as he entered sent shockwaves up his spine and down to his big cock.

“This house is incredible Carol. It is nothing like I would expect in a house in Florida. You really pay attention to details. I like your taste.” He looked around at the fireplace and the rich wood paneling. It was obvious Carol had done well for herself.

“Well, what are you offering Carol. I am not sure what I want so I guess I will just choose whatever it is that you have. Maybe I will have some of you...... err, some of what you are drinking.”

 

[wickedpen]

Carol gave him a "you dirty little boy" look then sashayed her way into the kitchen and returned with another glass.

"Vodka tonic" she said as she sat on the couch next to Michael.

"Thank you about the house. My husband is rich and well I like nice things" she said looking around. "Speaking of nice things" she said returning her gaze to Michael. "I don't have a niece." She waited for a reaction from Michael and with none coming continued. "My husband did go to the airport but for a flight to the west coach for business." She leaned forward after taking a sip of her drink and set it on the table. She leaned back into the sumptuous couch and smiled.

"So this is OK?" she said as he eyes slowly went from his eyes down to her hand now on his thigh.

 

[BeachBum25]

He saw the way she looked at him and gave her a wicked grin in return. He watched her as she walked away. This was new for him, but he had a desire for this mature woman. He wanted to explore every inch of her and see if she was as good a fuck as she was a flirt.

He looked down at her hand on his thigh as she asked if it was okay. "I had a feeling that you did not have a niece, and I am happy to hear that. The only person i wanted to see when I came here was you. You have been on my mind since I walked into my mom's house and saw you."

He turned to face her on the incredible sofa. "So, tell me something Carol.... will this mess things up with you and my mother? I don't want to interfere with your friendship, so, if it will, even though I want to spend time with you, I won't let it get in the way."

He looked into her eyes as a hand went to her blouse and undid another button. He didn't wait for her response. He knew that, even if she thought it would interfere with the friendship, she wouldn't tell him. His fingertips brushed through her cleavage as he undid the button. Then, he slid his hand behind her head and pulled her to him and kissed her hard and deep.

 

[wickedpen]

The young man nearly took Carol's breath away with his openness and honesty. Carol was used to a very different situation, a dynamic of submission and hope and usually disappointment. This was completely reversed and she wanted more. His hand on her neck pulled her mouth on to his. It was intense as his words reminded her this was her friend's son. Her friend she had lied to about a young woman for him, selfishly wanting him herself.

She eased back feeling as though she was opening for him as he moved over her. His hands on her breasts, firm and interested, unlike her husband or other men she had been with lately. She suckled his tongue into her mouth as though it were another part of him. he sensed it and began thrusting in and out of her pursed lips.

She was on fire for more and her hand went for him and was rewarded with a big hard cock trapped in his shorts. She use both hands to open his shorts and soon had her target in her hands. She moaned almost as loudly as he did, making them both laugh.

"Lay back baby" she purred as he let her take off his shorts and then begin sucking his cock as he laid back on the couch.

"Welcome to Palm Glades" she said as she took his head into her mouth. She bobbed taking the head and a little more. It was the hardest cock she had seen in years.

"God baby you are delicious" she sighed working lower and lower down his shaft. She cupped his heavy balls. She lashed her tongue against him and bobbed faster and faster. She wanted him to cum. She wanted to swallow his seed. She looked up at him as he watched her. She could see he was close as his mouth hung open. She put both hands on his cock and pumped as she took a breath.

 

[BeachBum25]

He was shocked at how she reacted to the kiss, but he did not let on. He enjoyed her firm tits and how they felt in his hands. When she went for his cock, his tongue thrust harder into her mouth... fucking her mouth like he wanted to fuck her pussy.

As he laid back on the plush sofa and she took his big, hard shaft and treated it better than he had ever experienced. Her mouth was incredible and she knew how to use it perfectly on his throbbing member. He reached behind her head with one hand and ran his fingers through her hair as she bobbed up and down on his cock.

His free hand reached down for her breasts, and in his angst to expose them, the last couple buttons went flying off the blouse. He caressed her breasts through her bra as she worked him closer to orgasm.

"Fuck, you are so good. You keep that up and I am going to cum so fucking hard for you Carol." It was just a matter of minutes before he exploded. He shot giant ropes of his thick cum into her mouth and onto her face. "Yesssssss. So fucking good."

When he was finished, he didn't hesitate. He rolled her onto her back on the sofa and aggressively removed her blouse, her bra, and her skirt... tossing them to the floor. He slid her panties aside and gave her pussy a long, slow lick. He paused and looked up at her. "You want more of that Carol?"

He did not wait for her response. he went back to her pussy and licked it again and again.. long and slow. He removed her panties and tossed them over his shoulder, having no idea where they landed... nor did he care. He went back to work with his tongue... licking her pussy slowly and teasing her ass with each long lick.

 

[wickedpen]

She had not felt such excitement in years. It was like turning back the clock. His cock throbbed with life in her mouth as she savored giving such pleasure. He moaned as his hand pulled her down on her his cock pushing into her well trained throat. He was using her and she loved it.

"Fuck, you are so good. You keep that up and I am going to cum so fucking hard for you Carol." was music to her ears as she had not tasted the cum of such a stud in ages.

"Momma Carol needs a facial" she moaned as her hand tightened around the base of his cock. Still plenty for her mouth to work with but she wanted to hold him back until he just could take no more. She felt him throbbing against her fist as she forced his bulbous head into her pursed lips.

"fuck me, fuck me, fuck me" she hissed then pushed her sucking mouth down his shaft and released him. His ejaculation was a thick wave shooting up through his rock hard cock into her mouth. She bobbed up and down for the second. Tasting him she pulled back and let the third and forth cover her face as she sighed "the best moisturizer" before burying his cock back in her mouth to milk what was left of him.

She was rubbing his seed into her face and neck as he wasted no time moving her to her back and stripping her. She helped as much as she could but he was on a mission and she was the beneficiary.

He was between her legs and lapping at her dripping flesh before she realized it sending a wave of pleasure through her.

"You want more of that Carol?" he hissed as though determined.

Carol grabbed her tits arching her back and then bucking up into his face. "Fuck yeah!" she said excitedly. He was already there as he stripped her and went to work. It had been so long since she had felt an excited man between her legs pleasuring her for her sake.

She tussled his hair and pinched her swollen nipples opening her legs as wide as she could for him. "Oh Michael, that's it" she exhaled "don't stop, keep licking momma Carol" her moans were erotic as the only other sounds in the room were the lapping and sucking of Michael on her engorged lips.

 

[BeachBum25]

Michael was amazed at how wet Carol’s pussy was. It made him lick her faster as she pressed her hips to him. He slid his hands under her ass and spread her wide before him. Looking up at her as he ate her pussy, Michael could see Carol playing with her big tits and pulling in her erect nipples.

His tongue began to move in and out of her soaked pussy; tonguefucking her slowly and deliberately. Her words and actions indicated that she was enjoying the way he was treating her. He was not in a hurry. He was going to please her like she had never been pleased before. He was going to make her want him again and again whether her husband was out of town or not.

As he spread her ass wide, his fingertips teased her tight rosebud. He felt her react and he smiled to himself as he moved his tongue in and out of her faster... pushing it deeper into her needy pussy.

Pulling his tongue out of her drenched pussy, he allowed the tip of his tongue to flick her tight asshole before he resumed licking her clit. He wanted to drive her crazy. He wanted her to cover his face with her cum, and then he wanted to bury his big, hard cock in her and give her what she really needed

 

[wickedpen]

Not only had she not had a man like this in many years, she may have never had one as good as Michael before. He was doing things and going places she had never imagined and it was amazing. She wanted to give hm what he was giving her.

"Oh God Damn that's good Michael" she called out slamming her fists into the couch as her body jerked with his stimulus. Her legs around as wide as she could get them and wanted this to never stop.

She felt herself building. She was going to cum and cum hard. She did not want to turn Michael off.

"Come here baby, get inside me" she moaned reaching for him. But he resisted and continued and her body came closer closer.

"Michael you are going to make me cum," she gasped. And after a slight pause "all over you" she warned. She often squirted when she masturbated and this was the hottest she had been in a long time. Suddenly his nose against her clit and his tongue darting in and out of her thick creamy lips his eyes looked up like a boy caught with his face stuck in the cookie jar, she erupted. Her cry echoed through the house as her muscled draw into a knot and then the only sound was Michael groaning with effort and then "aaaaaaaaaahhhhhhhhhhhhh" Carol cried and squirted into Michael and then across the room as he moved. She stopped and then refilling her lungs came again, a long intense wail of pleasure. She collapsed as her body jerked and Michael stood over her wet with their juices and massively erect.

"How can I please you?" Carol sighed breathlessly looking at him. She was sprawled on the couch numb with orgasm. "How can I make you feel this good?" she asked with a smile.

 

[BeachBum25]

Never before had he been with a woman like this before. He was going to make the most of this opportunity. Who knew when it would be presented to him again. He stood over her; looking down at this incredible woman..... a mature women who he had never thought would turn him on at all let alone as much as he was now.

“We are not even close to being finished Carol. Your husband may be one and done, but not me. I am going to enjoy you all fucking night long. If you think it felt good to have me eating your pussy, imagine how good it is going to feel to have this big cock filling you.”

He smiled down at her as he reached for her hand. “In your bed. That is where you are going to cum next. Lead me there. I am going to fuck you in your marital bed. “. He helped her off the sofa and kissed her hard..... possessively. “Take me to your bed and fuck me good Carol.”

 

[wickedpen]

Carol smiled at Michael's bravado. She was more than happy to feed his ego and as he pulled her up and demanded having her in her "marital bed" she smiled. She wrapped her hand around his hot hard cock and led him upstairs by it.

"That ex-wife must have had a kink for little boys cause you are amazing" Carol said without looking back at him. They climbed the stairs, cock in hand and walked down to the master suite. it overlooked the golf course and canal with a entire wall of glass. the bed was facing outward. There were no shades or curtains.

"You wanna fuck momma in her bed now baby? here it is." she asked as Michael eyed the wall of glass. Carol walked over and pulled the white bedspread off the queen sized bed. It has an especially thick mattress and there was a step to get up on it. She pulled back the white blanket and sheet standing on the step as Michael watched.

"You want to be the man tonight?" she asked, almost challenging him. "Our maybe my grown son's room would be more to your fantasy?" she said licking her lips.

 

[BeachBum25]

“Right here is just right for me Carol. Maybe your son’s bed is where you want us to go. Well, we can go there later.” He smiled at her evilly and took her hand. “I have a better idea.” He helped her down to the floor and led her to the wall of glass. He pressed her back to it and kissed her passionately as he caresses her breasts firmly.

Then, without warning, he spun her around and pressed her tits to the glass. He moved in behind her and slid his big cock between her legs as he kissed the back of her neck. “Not sure about you, but I love this view.”

His cock slid along her silky pussy; the friction creating even more heat. Pressing the swollen head of his shaft to her pussy, he thrust into her.... filling her with young, thick cock. “Fuck, your pussy feels good wrapped around my cock.”

It wasn’t long before he was thrusting into her hard and deep.... filling her... stretching her pussy so good. He felt her pressing back to her.... his member filling her so deep. He wasn’t sure how long he would be able to hold out before filling her with his cum.

 

[wickedpen]

"... Maybe your son’s bed is where you want us to go..." he said as the fantasy filled her but was quickly replaced.

It was as though he was reading her mind. She had fantasized, even masturbated against that window but her husband refused to every do anything.

"I didn't pay for this house so my wife could be the village slut!" he said when she playfully suggested it one morning.

"Apparently he did" she murmured to herself as she felt the hard young cock under her. His forceful handling had triggered a desire she had almost forgotten about. She loved being taken. She was not the kind of girl to complain about being forced. No was not a word she used much.

The sensation of Michael inside her nearly buckled her knees as she gripped the frame of the door looking out into the twilight as a pair of golf carts drove by..

She arched her back although he was so big he needed little help but it felt so fucking good.

“Fuck, your pussy feels good wrapped around my cock.” he grunted as his hands tightened on her and he worked himself in and out pushing her into the glass.

"Fuck, your dick feels good filling my pussy" she gasped nearly losing it. She never talked dirty with her husband but was now loving it. "that's it Michael, keep fucking me!" she grunted pushing back into his thrusts. "harder" she exhaled nearly cumming again.