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.