by Holly Ardent
When his fingers found her nipples and squeezed, Donna squeaked and her pussy tightened down on him. Even with all the lubrication she was providing she felt tight while she was cumming. It wasn't enough to stop him, but it slowed him down a bit.
He was slamming along when the angle changed on him abruptly. The back of his hands were pressed into the felt of the pool table as Donna collapsed onto it. She made sure to keep her legs spread, but they weren't supporting her weight any more, the table was. She moaned and said something that sounded pleased, but he couldn't make out her actual words.
She was squirming a lot and pushing his hands around on the table. He noticed the backs of his hands warming up from the friction and slid them out from between the table and her breasts.
Let her rub her breasts on the felt for a bit. The way she's acting, I bet that turns her on even more.
The new angle was making it hard for him to hold out. It made it much tighter where he entered and the sensation was starting to overwhelm him even after only a minute.
His hands went back to her hips and he held her in place as he slammed his cock in and out of her as hard as he could. Donna was making little squeaking noises now while thrashing around underneath him. Her pussy clenched as her back arched up and Jerry lost it. His cum went spurting into her, filling her pussy and dripping out around the edges as he continued to thrust several more times. His calves cramped on him and his cock became sensitive enough that he drove in as deep as he could and just stayed there while he finished cumming.
Donna continued to tremble beneath him even after he was done. He wanted to step back, but was afraid his calves weren't going to support him if he did. So he stayed where he was, sliding his hands to the edge of the pool table to support his weight.
A few minutes later Donna spoke up.
“I need to stand up and stretch some. Could you move?”
“I'm not sure,” Jerry replied. “My legs are giving me problems.”
He solved it by shifting himself to one side of Donna, with his hands still on the edge of the pool table to steady himself.
She stood and stretched her back out. Jerry watched as her breasts tightened and rode up on her chest as she stretched, then returned to their larger size as they settled into place when she was done. He felt his cock twitching a little at the sight, even while he wished he couldn't feel his calves.
She turned to him and noticed his arms supporting his weight.
“Where's the problem?” she asked.
“My calves. They both cramped up on me and now they feel like they've got Charley Horses.”
“Ow,” she said, her face wincing in sympathy. “Let me help you out.”
She offered a hand and, when he took it, used it to lower him to the carpet.
“Lie on your stomach,” she said.
When he did, she knelt between his legs and he felt her warm hands start to work his calves over. For a moment he felt like screaming as the pain increased, and then it passed, leaving his legs in much better condition.
“Roll over,” she said.
When he was facing up, she looked down at him and shook her head.
“That won't do,” she said.
She leaned forward and took his limp cock in her mouth. It didn't stay limp for long with her sucking on it and once she was satisfied with his erection, she sat back up.
“So, I've been thinking,” she said. “You're filling in for my husband, and with as helpful as you've been, and with as much pleasure as you've given me, if it were him doing all that then I might have given in if he'd asked me about something he's been pestering me about for years. So, if you'd like to ask me if you can fuck my ass, I'd probably say yes.”
Half of her mouth turned up in a smile as she looked down at him.
“It would be a first for me, and since I've been a first for you in so many ways, it would only be fair. Don't you think so?”
Jerry blinked at her.
She must still be drunk or something. Do I want to fuck her ass? Hell yeah, but if I do is she going to be pissed off about it later on? Does it matter if she is?
“Sure, that sounds fair,” Jerry said.
She waited, looking at him expectantly. It took him a moment to realize what she was waiting for.
“Can I fuck your ass?” he asked.
If he hadn't been erect already her answering smile would've taken care of it.
“I'd be delighted,” she said. “But I've never done it before, so you'll have to forgive me if it's a little awkward.”
“Likewise,” he said, “we can learn about it together.”
* * *
Donna stood.
“I think I'd like some music, how about you?” she asked.
“Sure, anything you want,” he replied.
She walked behind the half bar and he heard her rummaging through something back there. With a soft exclamation she chose something and moments later the music started. He didn't recognize it, but it had a good rhythm, very close to the speed Donna liked to have sex at.
She came back out from behind the bar, dancing a little as she crossed the room. When she knelt down on top of him and leaned over for a kiss, he discovered that she'd taken another shot of whiskey while she was over there.
“Are you sure you still want to be drinking?” he asked.
“It was just another shot for courage. Like I said, I've never done this before, despite him asking for it for years. I'm a little nervous about it.”
“Oh...”
Jerry's voice trailed off since he was unwilling to do anything that might change her mind.
She settled down on top of him and started rubbing her pussy along his erection.
“I think we'll need to start with you in my pussy again,” she said. “I want to make sure you're well lubricated before we try to squeeze you into my ass.”
“Anything you say.”
Jerry was eager to agree. Her warm pussy was stroking his cock, even if he wasn't inside of her, and all he could think of was getting back inside of her. He didn't really care if it was her mouth, her pussy, or her ass, although taking her ass held an extra attraction since she seemed eager to have him be the first to do it.
He bit his lip as she slid her pussy over the top of his cock and pressed herself down so when she slid back, his cock was pushed up into the perfect position for entering her. When she'd shifted around a little she started lowering herself, wiggling around until he was centered on her pussy. Then she lowered herself all the way down. There was no resistance at all, just the sudden wet warmth surrounding his shaft.
The next few minutes were pure bliss as she rode him slowly, matching her movement to the beat of the music she'd put on. Donna reached down and rubbed her clit while riding him, trying to get herself even wetter. Jerry just laid back and let her do what she wanted. He focused on the silken warmth surrounding his cock. The warmth that moved up and down, constantly in contact with every square inch of the skin on his cock.
As the song ended, Donna slid up off of him. She inched forward a tiny bit and started to lower herself. When the next song started she had the tip of his cock at the entry to her ass. The music started with a heavy bass beat and as it did, on the very first beat, he felt her lower her weight onto him.
His cock head penetrated her ass easily with all the lubrication she'd provided for it. Even so, she tensed up and bit back a tiny gasp of pain. It didn't stop her though. As the song continued, she paced herself to the bass. Each heavy bass beat sending her either up his cock or farther down it.
Her ass was tight around his shaft, holding it in a grip like a fleshy vise. He knew it was hurting her, he felt her flinches and could see the look on her face.
“You don't have to do this, you know?” he said.
Then he realized that his voice had been lost in the music so he repeated himself, louder.
“You don't have to do this, you know?”
She looked down at his face, her expression sl
ightly off-kilter.
“I know. I want to do this. I want to do this to you, for you, to deny it to him.”
Shit, she's slurring her words. She wasn't kidding about being a cheap date. I think she's totally drunk. I can't believe I'm about to say this. Am I stupid or something?
“Okay then, but how about we wait until you're a little more clear-minded?” he asked.
She shook her head.
“Can't. It's too late now. Besides, I needed the courage, and the numbing effect. Now shut up and enjoy my gift.”
She went back to riding him, driving his cock deeper into her ass on alternate beats, sliding herself partially off it on the others.
I tried. I'm not about to run away, so I guess I just lay back and enjoy it, he thought.
He reached for her breasts and began to stroke them. A smile flitted across her face for a moment, at odds with the expression she'd been wearing. Then the music began to speed up and she went back to a focused look of concentration as she sped up to match the beat.
His hands were on breasts still, but some of her intensity must have been contagious. His caresses became faster and more forceful. Finally he focused on just her nipples, pinching and pulling them. His discovery that he could tug on them and they'd stretch out to almost twice their normal length before Donna glared at him started him on his way to cumming. He felt that first sudden onset of warmth in his balls when he stretched them. Even so, he'd cum recently so he was pretty sure he had a few minutes left still.
He let go of her nipples as she continued to glare. One of his hands dropped to the floor at his side while the other made its way to her clit. When he started rubbing it, she jerked and lost her rhythm for a moment, but quickly caught it again. She fell back into the rhythm easily, but now she was also pushing herself forward to press against his finger each time she lowered herself on his cock.
He felt his orgasm slowly building and worked on her clit as hard as he dared. The results were worth it. Jerry watched as the intense focus on her face softened. The focus was still there, and it was certainly intense, but it looked as though she might actually be enjoying herself a little as well.
He pinched her clit firmly and then tugged on it. When he did that Donna lost her rhythm again. This time her back arched and he felt the angle of his cock change, her ass tightening down on him even more than it already had been.
Donna screamed and he felt a gush of moisture soak his pubic area. She'd just cum hard enough that her juices were gushing out of her pussy. After a few seconds he felt her resolve strengthen and she straightened up and started slamming her ass up and down on his cock. Now she was totally disregarding the music, any pain she might be feeling, and everything else. She stared down at his face, catching his eyes, and he was sure she was willing him to cum.
He didn't have much choice in the matter. He'd been on his way to cumming for a couple of minutes now and when she came the only thing that had stopped him from joining her was the new angle on his cock, which squeezed it tightly enough that he couldn't cum. Now that she was back at her original angle and slamming away on him his cock let go.
The warm feeling in his balls had continued to increase and blasts of heat ran along his cock as his cum shot into her ass. He felt his cock swelling, fighting for more room in her tight asshole, each time a jet of cum ran through his cock. The feeling was one he couldn't even think of words to describe, furious and intense in a way he'd never felt before and it was over all too quickly.
When Donna felt him cumming, she slammed herself down on him one last time, burying him to the hilt in her ass. She was still trembling and shaking from her own orgasm and feeling him cum inside of her ass sent her back into another tiny one.
Jerry lay on his back, spent. Donna was still mounted on top of him, quivering with pleasure. He could feel the trembling inside of her even and the motion kept his cock from going limp as quickly as it would have otherwise. She slumped forward, finally still, and his cock slid out of her with a quiet pop.
Donna rolled off of him. He wasn't sure if it was intentional or she'd simply slid. Either way, he edged over to close the inch or two between them, snuggling up against her side. They lay that way, silently, for several minutes.
Finally he broke the silence.
“Are you okay? It looked like that hurt.”
“I'm better than okay. It did hurt like hell, until it didn't any more. Once it didn't I had the most incredible orgasm of my life. I kept cumming and cumming, just from riding you with my ass. It was...” she trailed off, at a loss for words.
“Uh-huh,” he said nodding. “I don't think I could describe it, but Damn! It was good.”
She lifted her head and settled it on his chest.
“I wonder how long he'd stay away if I called him and told him that the remodel was going to take longer than I'd anticipated? Want a job for the rest of the summer? I can offer really... interesting... break times.”
* * *
A few days later a review showed up for the Quick Work app.
I tried this app, wondering if it was going to be any good. Now that I've tried it I have to give it five stars, but only because I can't give it more. I got myself a job for the summer until I go to college and the perks are unbelievable.
I give it five stars, but only because I can't give it ten.
Jerry R.
* * *
The End
of
Filling In
Main Street MILFs #2
To be continued in:
Guard Me
Main Street MILFs #3
* * *
Find Holly's other stories on her Amazon Author Page:
Holly Ardent's Amazon Author Page
Other stories in this series:
Quick Work: Main Street MILFs #1
Guard Me: Main Street MILFs #3
Fowl Play: Main Street MILFs #4
Complete series bundles by Holly Ardent:
The MILF Man Deliveries Series (Cheating Wife MILF Erotica) - complete set
MILF Money for College (Cheating Wife MILF Erotica) - complete set
Her To-Do List (Cheating Wife MILF Erotica) - complete set
Some stand-alone stories by Holly Ardent:
What Santa Doesn't Know (Christmas MILF story)
Spoiled MILF (Older Woman/Younger Man Cheating Wife)
Spilled MILF (Older Woman/Younger Man Cheating Wife)
Ride the Valkyrie (Mythological Erotica – Viking)