Mr. Nice Guy vs. The Concert Milf

God she needed a good fucking! She heard a constant, annoying moan from somewhere and it took her a moment to realize it was her own. Her pussy gripped onto his cock as tightly as it could. Over the last few years she has noticed that it was becoming easier and easier to cum. His hands reached forward and grabbed onto her tits and he picked up the pace, and that was all it took for her to start cumming!

Realizing she was cumming, Jason crossed her perfect legs to increase the amount of pressure her pussy was causing to his cock and held her legs out to a side, moving them slowly, changing the angle his cock entered her cunt, almost as if adjusting a TV antenna. Once her moan became a squeal, he knew his cock was slamming against one "g-spot" or another. Holding her legs in place with his left hand, he grabbed her boob hard with his right and started pounding into her as hard and as fast as he could.

A minute later she was still cumming! Was this what a multiple orgasm was? Or was this one really long orgasm? He wasn't sure, but as her eyes rolled back into her head he picked up the pace even more, the whole bed scooting with him as he did so.

Finally, her climax subsided. "Fuck me!" She said in exasperation.

Always willing to comply with a request like that, Jason rolled her over and lifted her waste until her knees were on the bed and her ass was presented to him doggy style.

"My knees are weak!" She complained to him. Jason wasn't listening. This time he slid into her smoothly with a slow hard pace. He could hear Connie saying fuck under her breath on his more aggressive thrusts. His hands were resting on her smooth incredible ass. Damn this milf was hot! And Jason was not just having sex with her, he was fucking her! And apparently not doing too poor of a job of it either.

Pushing himself as far into her as he could, Jason lifted her by her legs and tucked her knees up to her tits and pushed her ass down on her ankles. Putting his weight onto her hips with one hand and using her bundled up skirt as reigns with the other, Jason started plowing into her as hard and as fast as he could manage.

"Shiiiifuuugoooodaaaaaaa..." Connie couldn't even concentrate well enough to cuss. God she loved fucking younger guys!

Smack!

The sudden impact caught Connie off guard, and caused her to clench down hard on his cock just as he was shoving his tool back in. He was pressing down on her ass and hitting her pussy in places not many men did, and...

Smack!

... he was so damn big! Connie was almost cumming again! It wasn't possible for her to cum again so soon. And he knew she was cumming, because out of no where he said "I am close to cumming too."

Fuck! She couldn't have him pull out now! She was so close! Nothing to do but to hedge the truth a little.... "Just come inside me!" she cried out, "I can't get pregnant!"

Jason had never heard better news in his life! It only took a few more thrusts before he started cumming. Connie slapped the sheets and gripped them in her hands as he filled her with his cum, and her pussy was clenched so tightly against his cock he knew she was cumming too. He wanted to stop when he came, but her orgasm had only just started. He kept fucking her as she came.

When her body finally stopped shaking, Connie realized that her man for the night was still fucking her!

She spun out of his grip in an instant, eyes wide, staring at his rigid cock. "Your still hard!"

"It takes a while to wear me out." Jason bluffed. He had no idea how he was still erect. This was only his second time getting laid, but thinking back he supposed he was still hard for quite a while after that first time....

Connie started stripping. Apparently she wasn't done either. Naked, she took Jason's breath away. She lied down with her head on the pillow and beckoned him on top of her. Jason obliged, but slowly.

He moved to the foot of the bed, and slowly started kissing his way up her long and perfect legs. He kissed her left foot. Kissed her right ankle. Kissed her left shin, then her right a little higher.

Back and forth he worked his way up her legs, giving a little french kiss to her pussy on his way to her abs. Not a big one, he did not want to risk sucking his own cum into his mouth, after all.

She had a little six pack, he realized.

Her tits were small, but rock hard as they say. Her body started to shake as he took each one between his lips.

Once he reached her lips, they kissed, and kissed passionately like long term lovers. Moving her hand between them, Connie lined his cock up with her entrance, and he slid straight in. He loved, for a moment, the feel of her smooth legs against him.

But soon her legs were wrapped around him, and she was whispering, urging him to fuck her harder.

Annoyed, he complied. But he did more than fuck her harder. He reached out and grabbed her hands and pinned them together above her head. She was enjoying it, but she still was telling him to fuck her and now also telling her to hold her down. Still talking like she was in control. So sliding one arm behind her back he grabbed her wrists and pulled them down behind her head. She had to arc her back to keep her arms from hurting, but still she told him to keep fucking her, telling him he was doing a good job, and Jason wanted to take that feeling of being in control back away from her. Wanted to be in control himself.

So he pulled her wrists down further behind her. "Ow!" Connie said, arcing her back even more. "Let up a little." This time Jason did not comply.

He picked up the pace in fucking her, and no matter how hard she struggled he did not let go oh her arms. "What are you doing to me?" She cried out as her body started to shake from a full body orgasm. Only when the shaking stopped did Jason released her arms. She drew them in in front of her, rubbing in at the elbos. She was covered in sweat, both hers and his.

Maintaining eye contact, and staying deep inside of her, Jason rolled them over so that he was on his back and she was on top of him, doggy style. "I need you to fuck me until I cum again." He told her.

Connie knew it was an order. What had she gotten herself in to? She wondered....

Still, she hadn't been fucked like that since she was a teenager, so she was not about to say no.

She nodded her consent to him and started sliding her sore pussy up and down his cock. Her pussy was soaked, with both her fluids and his, so while he slid in and out easily enough she was still sooooo sensitive!

Jason enjoyed watching the worn out beauty, as old as his own step-mother, pushing herself to get him off. He put his hands behind his head and watched her as she bounced on his cock, eyes closed, intentionally squeezing his cock with her pussy. "Fuck me harder." He would tell her occasionally, reinforcing the order with a slap to the ass.

Twice while she worker her best magic on top Jason had gotten close to cumming, and twice he resisted the climax with everything he had. He did not want to be just another lay. He didn't want her thinking they had just had great sex. He wanted her to think of him as the best sex she had ever had.

She couldn't hide how tired she was, and eventually her pussy became so soar that she had to come to a stop.

"Is that all you got?" He asked. Connie hated him, she decided. once again she started fucking him with everything she had, only this time she just didn't have as much to give, and it showed. Jason stopped her.

"I will let you get off of me..."

"I am going to make you cum." She interrupted defiantly.

Unabashed, he started over, "I will let you get off of me BUT.....I am still going to cum before we are through here. If you get off of me though, you have to agree to let me fuck you in the ass until I cum."

Connie was no stranger to but sex, and while his giant cock in her ass was not her favorite idea, at least she would be able to lie down.... "Deal." She said as she fell off of him and onto her stomach. Her lover was soon up and straddling, sitting on her legs as he fondled her ass. She loved the way his young, strong hands felt as he squeezed and slapped her cheeks. She closed her eyes for a moment enjoying the youthful massage. But soon play time ended. She felt him as he slid his dick head up and down her pussy.

"That is not my ass." She informed him.

"I am just getting the head wet again for you." he told her before lining himself up with her ass. He pushed his cock head in her ass. She held her breath. He waited, enjoying the new sensation of being in someones ass. She breathed out, breathed in, held it. Again he waited. She breathed out, and he slammed into as hard and as far as he could go before his cock bent as if hitting a brick wall.

Her intake of breath sounded like an inverted scream. She bit the pillow. He grabbed it and moved it away, then pinned her arms by her side as he pulled back almost all the way out.

"Don't hold it in." he told her, "I wanna hear you."

Then he started fucking her ass. Much harder than he had fucked her pussy when he had been on top just a moment ago. She was speaking gibberish that sounded like a mix between words of encouragement and senseless moaning and grunting. It was music to his ears.

"I am going to cum!" He warned her. It was music to hers.

Jason was staring and the perfect ass that gripped his cock. How many millions of men had wanted to fuck her ass over her many years of being a babe, he wondered. It was the last thought he had before he came for the second time in an hour, and it would be the last thought he had before he work up. After he came, he passed out.

When he woke up, the hotel room was empty.

Shit! It was morning! Jason jumped up and threw on his pants before he realized the pockets were empty. Frantic, thinking he had been ripped off, he spotted them under a piece of paper on the bedside table. The paper turned out to be a note.

"I have never been with a man who made me pass out before, but I was happy to wake and find you had passed out too. At least, I assume you did not fall asleep with your dick still in my ass. I got your number out of your phone. I did not leave mine... married and all. I will give you a call next time I am in town. You can count on it. Think you could handle two of us? It is always nice to share...." The note ended with a smiley face.

There was a hundred dollar bill sticking half way out of his wallet. It hadn't been their before. Jason laughed out loud. He was her whore after all, he guessed. Well, shit, sex that great and a tip, who was he to argue with that?

Jason realized it was too late to rush home before his ass was grounded for ditching his sister, so he stripped back down and took a shower.

As he left the hotel room, a guy poked his head out of the door. "Have a good night last night?" The guy asked.

"Yeah, it was alright."

The guy laughed. "Sounded better than alright."

It wasn't until he left the hotel that he realized he didn't have a ride back to his jeep. Shit. Jason took off at a jog on his way back downtown. He pulled out his phone and checked his inbox for messages. Surprisingly, he had five from Donna.

"So who is the cougar? Someone you know?"

"I am starting to get jealous."

"A back rub, now I am jealous!"

"Did you leave!? Aren't we chaperons supposed to be responsible?"

"Ok, going to guess the phone is off. I am going to cover for you and say you told me you were going to head out with friends, but you owe me big boy."

Jason had slowed to a walk. He texted Donna back with "Thanks for covering for me! And yes I do owe you something big. Just let me know when you want to collect."

He turned his phone off of silent and resumed his run, this time at a more relaxed pace. It eventually beeped. He stopped and checked it. "Something big? You left us feeling pretty jealous last night."

Us? Oh, she meant Highland. Jason was not attracted to her at all. What to say next... "Don't be too jealous. She was in from out of town and only got one night with me. YOU" all in caps to emphasize not Highland "can have me anytime you want me."

"Does it bother you that I am married?" she asked.

"The woman I was with last night was too, and I am not exactly feeling bad about things now, am I?"

"Cocky much?"

"After last night, very. Meet me alone and I will show you why."

"Is that a promise?"

"A guarantee."

"I will keep that in mind. ;)"

Jason's jeep was right where he left it, and no trouble awaited him at home. His step-sis was disappointed that he bailed, but since he had cleared it through with one of the parents, his own parents did not seem to mind.