Mr. Nice Guy Vs. The Interview

This is the third story in the Nice Guy Series

School had finally started, and as the days started to tick by Jason felt like he was starting to loose the charismatic edge he had gained over the summer. He was starting to feel much less like a ladies man and much more like the wall flower he always saw himself as.

Jason so one Friday, Jason texted Donna, his step-sister's friend's reasonably attractive mom. It was inevitable. Over the last few months Jason had scored with two chics, a girl his age and an older woman. He had no way of reaching the milf he had slept with and he was stubbornly not calling the girl his age yet, waiting to see if she came back to him for more.

Now that Jason had gotten a taste of sex, he needed more. Donna had made a point of letting him know she was available.

She was not gorgeous, but attractive in a house wife kind of way. She was short and curvy, but not exceedingly so. Still, Jason had found himself masturbating to thoughts of her on more than one occasion over the last four days. She was unconquered territory, after all.

Jason texted her at noon from school, hoping that it decreased the chances of her husband or daughter reading the message.

"So when, exactly, do you think I might be able to pay you back?" Jason sent.

The message came back seven minutes later. "Who is this?"

Ouch. Not a good sign.

"Jason. Ouch."

"O.M.G! I deleted your number in case someone looked through my phone. I didn't think you would actually text again."

"Didn't we have plans?"

"You don't WANT to actually 'pay me back' do you? You don't have to."

"I want to fuck you. Tell me a time and a place and I will do exactly that."

A few minutes passed. Jason had to fight himself not to text an apology. Maybe he came on to strong... Then she texted back. "I am driving and almost went off the road. Your bad! And a tease. What would you say if I said I am free right now?"

"Give me your address." Jason fished his keys from his pocket and considered skipping school for the first time in his life.

"O.M.G! Um, Stacy is going to her cousins tonight and my husband works until after 9. If your serious, get over here now!"

Jason laughed. He checked the clock again. It was still just noon. They had nine hours. "Keys in hand. Whats the address?"

*********************

Jason's phone buzzed again as he pulled onto Donna's street. She was having second thoughts. This text was not the first concern she had voiced.

The convo had gone something like...

"What will the neighbor's think when they see your car?"

"They'll assume I'm there to fuck your daughter."

"What should I wear?"

"I don't care, you won't be wearing it long."

"We can't do this, what if you don't like the way I look."

He typed "You think too much." He had skipped the rest of his school day, which was a big deal for Jason back then. He was not about to skip class and come out with balls just as blue as they were before. "Your getting fucked soon. Accept it. Think about what you want me to do to you instead."

She had texted him five more times since, but he did not read them until he parked in her driveway. He gave them a quick scan to make sure none said "My husband is coming home." Turned off his phone and got out of his jeep.

His heart was racing, so he took a moment to steady himself behind the veneer of the overconfident ass persona he had been developing.

A few seconds later, he knocked on the front door. It opened quickly and Donna stepped back from the door, beckoning him in urgently while looking passed him at the empty street. Jason casually stepped inside. She shut the door and stood on her tiptoes, pressing herself against the door to look out the smallish windows at the top. She was not exactly dressed for sex. She wore a green turtle neck sweater and a long jean skirt that came halfway down her calves.

Jason chuckled silently on what she had chosen, if only because he knew she had put a lot of thought into it. This meant that clearly she had little self confidence, regardless of the game she had been speaking up until she realized something was really going to happen.

Jason, however, had come for sex, and sex was what he was going to have. He stepped in behind her and pressed her against the door. His cock pressed deep into her ass as his hand slid purposefully up her sweater and squeezed her very adult chest.

Her forehead hit the glass and her knees gave out. Jason, held her up by pressing harder into her with his cock and squeezing her decently stuffed sweater with his hands..

"Oh my god I am going to have an affair." She whispered to herself. Jason released her chest and steadied her against the door. She started to turn to him but he firmly held her against the door until she got the idea. He grabbed her hips and pulled her lower body slowly away from the wall until she stood in a sort of doggie style position.

"No talking. No second thoughts. No objections. I am not leaving this house until I have my way with you. Understood?"

She was quiet for a moment. "Yes sir." She said. Jason figured she would enjoy it more if she was told there was no more room for second thoughts.

He slid his hands slowly down her legs to the floor, the slid them back up her legs and up her denim skirt.

She took a quick and sudden breath.

"No talking." Jason told her.

"I didn't shave my legs this morning."

"I could care less, I said no talking." Jason had slid he denim skirt up as he spoke, and had just pulled it up over her largish ass. He spanked her to emphasize his order, and spanked her hard. A red hand print was left on her ass. She nodded, getting the hint.

Jason slid her panties down, slowly, all the way down her legs, dropping to one knee so that she could step out of them. This put his face withing inches of her pussy.

Her married pussy.

Jason breathed hot air onto her married pussy.

She took a quick gasp of air and held it.

He slid his hands back up her legs and pressed his thumb into her cunt. She was soaked. Jason removed his thumb and rubbed her clit gently with a finger. She whimpered. Jason sucked her wetness from his thumb and fingers audibly. She held her breath again.

He licked her cunt.

"No!" she cried in shock, spinning and putting her ass against the door. She froze. With his free hand, Jason had taken down his pants and boxers. When she jerked away Jason stood and casually took off his shirt. Her jaw dropped. He stepped out of his pants and shoes. Her eyes were locked on his bobbing cock.

"I am already having an affair" She said to herself.

"I am not getting dressed until I get tired of fucking you, so there is no point in playing hard to get."

She smiled broadly. "And I wouldn't let you get dressed until you were tired of fucking me, I am just not comfortable with you going down on me." She explained.

"Then get down on your knees and distract me Mrs. Rhea."

"You can still call me Donna."

"I didn't feel like it Mrs. Rhea, now stop talking and get down on your knees." Jason stepped in, gripping his cock in his hand and pointing it at her. She smirked, but slowly she obeyed. He placed his hands on her head and told her to take her time.

She reached up and started stroking him. He was inches from her mouth, the tease..... Then, quite suddenly, she obeyed him. Swallowing him all the way down her throat. Jason rolled his head back and smiled. He was getting his third blow job. Or rather, a blowjob from his third girl. He wondered how many he would need to get before he stopped counting?

Donna's husband had apparently put her to work sucking cock before, because she knew what he was doing. Not only that, but he had trained her to give without receiving? He decided he should probably thank her husband if they ever met. Of course he probably would not want to hear how Jason was benefiting from his hard work.

Jason let Donna suck him until he was fully engorged, and quite a bit longer after that, then he pulled her to her feet then pulled her sweater off roughly. Her boobs were larger than he remembered, straining out of the bra too small bra that held them. Jason tugged the bra out of the way and set his lips to them, playing with each nipple with his tongue, teeth, and lips. He slid a few fingers into her wet cunt and fingered her for a good couple of minutes while he sucked on her largish boobs.

She was ready to be fucked. Very ready.

Once they were both completely naked, he took her by the hand and led her through the house. He had planned on fucking her on her marital bed, but as he passed Stacey's room, her daughter's room, he suddenly had a better idea. She resisted him as he pulled her inside, so he had to wrap a hand around her waist and pull her in forcefully. He shoved her face down onto her daughters bed.

He didn't know his step-sister's friends very well, but he had seen them for years. Stacey was a super slim blond with perky tits. She was too young for Jason, she was 18 true, but and way too immature. That was made clear by all of the stuffed animals. The bed was horizontal against the wall, and the entire far side of the bed was lined with stuffed puppies, cats, and rabbits.

Jason took in the odd decorations for a full ten seconds before he shoved his hard cock deep into Stacey's mom. "Oh my God!" Donna yelled.

She was not as tight as his previous two fucks, so he slid straight in allot faster than he had intended.

"He can't help you now Mrs.Rhea, Your mine Mrs.Rhea." Jason started fucking his married conquest on her own daughters bed.

Unlike the first two times Jason had fucked, this time he could tell he reached his first climax pretty quickly. He didn't feel any obligation to impress Donna, so he had been focused entirely on his own pleasure. It was an overconfident mistake. "Are you close?" he asked her as his own climax approached. His own pride would keep him from cumming before Donna.

"Are you kidding?"

Potentially insulted, Jason spanked her harder than he meant to. The impact felt good on his cock. Too good. "Answer the question!"

"I've cum twice!" she screamed!

He wasn't sure if he believed her. He didn't notice her climax. Moreover, if he came too soon he was not guaranteed an invite back. Having lost easy access to both of his prior conquests, at least temporarily, he needed to make an impression.

"Don't cum inside of me!" She squealed. That was disappointing. He had assumed that he could, since she was an older woman.

"What makes you think I am close?" he bluffed.

He pulled out of her pussy and hopped up on the bed, sitting his bare ass sitting on the pile of stuffed animals facing Donna. He pulled her by her hair as he guided her head back onto his cock.

After climbing up onto the bed in a kneeling position, she sucked the hell out of his cock, assuming he was close to climaxing. He was, so her was trying to put his mind on anything but the epic blowjob he was receiving. This was difficult since his hands had a mind of there own and were giving her boobs another once over. He tried only focusing on the sensations from his hands, but the damage was done. His only reprieve were the three times she choked on his cock from taking him in to deeply, but each time she caught her breath and went right back to it. He had gotten too close to soon. He needed to cum.

He held her head down on his shaft as he hit the point of no return. She started gagging almost as soon as he started cumming, and cum shot back out of her mouth over his cock and balls and onto the stuffed rabbit and pink comforter. She tried to get up but he held her down as he continued to cum down her throat. She swallowed quite a bit. Jason was impressed.

When he was finished he let go and she looked frantic. "I have to get your cum off of the comforter before it stains!" She beckoned him to stand so he would not soil the bed any further. He stood slowly, but had no intention of letting her clean up just yet.

"What makes you think I am done fucking you?" Slowly her eyes drifted down his pecks and abs and locked onto his still hard cock.

"Oh my God." She said, backing up slowly, and she started to back away from it like it was a snake. Jason stepped forward, matching her pace.

She backed into Stacey's computer desk, stumbling over a chair so that she was almost sitting on the keyboard.

"You have been saying that allot today." He stepped in close and pulled the rolling chair out from under the desk and flung it aside.

"I've had my reasons."

"All good I hope...." Jason stepped up to her so that his cock was pressed against her tummy. She put her hands lightly on his chest.

Her eyes went large and she nodded. "I was having fun flirting. I wasn't thinking it would actually lead somewhere...."

Jason reached behind her and shoved the keyboard, monitor, and all of the crap on the computer desk back out of the way. "I was having fun flirting too..." He leaned down and grabbed her legs, lifting them slowly towards his shoulders. She grabbed the desk in a panic.

"This desk can't support me like that!" She exclaimed. Jason ignored her words.

".. but I decided I would have a lot more fun fucking." He placed her legs almost vertical against his chest. It was difficult for her to keep them there, do to fear of breaking the desk and being generally out of shape, but she tried hard to obey his intentions as he let go of her legs and lined his cock back up with her pussy.

Slowly this time, he slid back into her. "Your cock is so big..." She cooed.

"The better to fuck you with my dear." He said as he slid his full length into her. He slid out and slid back in just as slowly. "And I am willing to fuck you again Mrs Rhea..." He pulled back out and slid in faster, with each part of the sentence, "...any.... and every... time... you ... want!" Wrapping his arms around her legs to keep her from sliding forward or back, Jason started fucking her wet, sopping cunt as hard as he could, humping her against the cheap computer desk.

The desk shook and creaked and cracked, but Donna didn't complain, her eyes rolled back in her head and she started moaning very audibly.

"Fuck me." She whispered. He encouraged her to be louder. "Fuck me!" She said louder, so he fucked her harder. Her feet and shins slid down his sides but she kept her thighs held up and spread out for him. Spread eagle and the ever creaking computer desk. "Fuck me." she said it again and again a little louder each time, so he fucked a little harder. Getting the idea, she started shouting it, and he started fucking her as hard as he could.

She was having a multiple orgasm, Jason realized. This time, every time she climaxed he could feel her pussy muscles, her notable muscles, clench and pull at his cock. She fell back into the computer equipment as he fucked her, but still she called out for more, so he did not think about slowing down.

"I am close to cumming again." He told her. She didn't respond, still climaxing herself. She would have let him cum in her easily considering the state she was in, but he didn't want to risk getting her pregnant. Not really. Strangely, some part of him considered it, but wisdom one the coin toss.

Wrapping his arms around her body, Jason hoisted her off of the desk. She was heavy, and she tensed hard as he lifted her, wrapping her arms around him and once again whispering with the "Oh My God"s, but as he approached the bed she stopped freaking out and instead buried her tongue down his throat, kissing him deeply and desperately. He carried her easily enough over to the bed and laid her on her back.

Cock still buried in her cunt, standing over her beside the bed, he spread her legs wide and supported his weight on them. Closing his eyes, this time he sought his own climax, and it came readily. He pulled out at the very last possible second and started stroking himself, shooting his ejaculation up her body and onto her tits and face.

Not caring about the comforter, and generally enjoying the roll of being an ass, he spread his spray out to the left and right, all over Stacey's bed spread.

Donna didn't respond.

Curious, Jason leaned down and kissed her pussy, knowing that she had resisted before.

This time she let him.

He explored it thoroughly, if briefly. He was certain he had earned a round two, but you can never be certain about what someone else was thinking, so he wanted to explore her as much as he could before she decided they were done.

He stood up and asked "Uh... you ok Donna?"

"Thank you." She cooed.

Jason stood in silence while Donna laid there smiling, letting Jason's cum dry on the bed spread.

Eventually Donna stood and walked passed him to the bathroom. Jason followed.

She wet a towel and wiped off his cum and her sweat from her body. She offered it to him and he washed himself off as well.

"I WAS planning on having an affair." she explained conversationally. "Just not with an 18 year old boy."

"Boy?"

"Ok, younger man. Who is EIGHTEEN!!!" She picked up a dry towel and wrapped herself in it. She walked passed him towards Stacey's room. Jason followed.

She grabbed the comforter and pulled it off the bed, bundling it carefully on the floor. "I even had a guy picked out. I work with him. He is my age, and married as well, but we have been flirting all year..." She stopped speaking as she thought, either about the older man or about what ever it was she was wanting to say. When she started speaking again, she started sorting through stuffed animals, selecting any who might have been hit with cum.

"I am not comfortable being a home wrecker. Just because my home is wrecked doesn't mean his is. And just because he complains about how awful his marriage is doesn't mean it is bad at all. Men lie. No offense. And ever since he, my husband, hurt his back, five years ago, we have had very limited amounts of anything. Almost always I suck him till he cums then take care of myself while he sleeps. And he only lets me do that to him a few times a year it seems. Every other night we fight. He used to fuck me everyday, and not just before we married, I mean for years...." She dropped the tainted animals into the center of the comforter and picked up the pile, leading the way to the laundry.

Jason walked behind her. He was still completely naked, and she was only in a towel. Even though Jason was soft, he was still turned on..

"Did you mean what you said, about this not being a one time thing?" She asked him.

Jason leaned against the wall and crossed his arms. "I am up for coming over as often as you'll have me 'til you get tired of me." He said with a smile.

She smiled back at him. "I am sure you will get tired of this old broad long before I get bored with you. But until you get tired of doing whatever you just did to me, consider this an open invitation."

Remembering that she had offered him a job at the concert, he tried to be a little witty. I wish I had time to go full time, but with school starting back part time is the best I can do."

"Oh, she said, turning with real surprise in her eyes. Were you still wanting me to get you a job at the grocery?

Jason laughed. Why would she think he was really talking about the job offer. He stepped in close and put his arms around her. "I meant working full time at getting you off, but I could work for you at the grocery as well if that turns you on...." Jason enjoyed the way her full breasts pressed against his chest. She kissed him again, and they made out for a moment standing in the laundry room.

"Oh my God, your hard again...."

"Getting there."

"Your hired...." She looked him in the eye. "...for both jobs." she winked at him and he pulled her towel free and let it his the floor. "But if your working for me maybe I should try giving you orders. Lay down."