by Holly Ardent
“Lie down,” he said.
Jessie started to slide back onto the couch.
“No, on the floor. I don't want the couch, too crowded.”
She slid to the floor and moved away from the couch. When there was enough room to all sides of her, Jack stopped her movement. He pushed her down on her back and knelt between her legs. A quick probe of her fingers showed that her cunt was still soaking wet.
I want her to cum again before I enter her. Preferably I want her cumming while I enter her, he thought.
He leaned forward and started rubbing his cock up and down her cleft, making sure that it rubbed against her clit each time he moved forward. She started squirming almost immediately, but he held her in place by setting an arm tightly to either side of her torso. Her squirming wasn't about to shift the weight his arms were supporting.
“If there's anything you'd like me to do, just tell me. You might get it if you do,” he said.
“Fuck me please? Stick your cock inside of me.”
“Soon, very soon,” he said.
He leaned forward and sucked a nipple into his mouth. When he had his lips pressed against the flesh surrounding it, he bit down gently. Jessie responded with a sharp intake of breath and a shudder. Jack found the reaction interesting and bit harder. Jessie's breathing sped up.
He kept his teeth clamped on her nipple, occasionally putting a little more force into the bite. At the same time he sped up the strokes of his cock, striking her clit more frequently and more forcefully. She tensed beneath him again and while she was still rigid, he let go of her nipple, slid back a little and sent his cock driving into her pussy.
Jessie was tightly clenched when he entered her, but she was also wet enough that he slid right in. She let out a strangled gasp as he drove into her. Her body was rigid beneath him as he pushed harder. Whenever she was too tight to let him slide in, he drew back an inch or two and slammed forward again. Each time he did that she either gasped or, if she'd started relaxing some since the last one, ended up fully rigid again.
She was panting before he was all the way in and when he saw her face turning red he drove in as far as he could and stopped, waiting.
He felt her pussy relaxing around his cock and resisted the urge to immediately go deeper. When her face returned to its normal shade, he reached up and pinched her nipples. She tensed again and he felt her pussy clamp back down. He slid one hand down and started teasing her clit again. It took a minute before she managed to gasp out.
“Fuck me hard, please?”
He pinched her clit roughly and started driving into her again. He slowed his pace and, this time, when she started to relax around his cock, he kept going. Before long he was all the way in.
Now he started speeding up again, slamming his cock into her. He shifted a little so he was driving in at a slight angle and his pubic mound was striking her clit with each stroke.
Jessie started making nonsensical noises as he continued to pound in and out of her. Jack considered stopping, but decided to go a little longer first.
Crap, I haven't even been paying attention to how good this feels. I've just been focusing on trying to make sure she cums. I think it's my turn for a while.
Jack slowed down and started making his thrusts longer. He drew his cock back until only half his head was inside of Jessie's pussy and then thrust hard and deep, sliding all the way in with the satisfying smack of flesh on flesh. He liked it so much that he did it again, and again. Jessie was tight enough that he felt it, but loose and wet enough that there was no problem driving all the way in with each stroke. When he thought he was getting close to cumming, he stopped again and pulled out of her.
* * *
It took her longer to recover this time and the first word out of her mouth when she had was:
“Bitch.”
“What?” Jack asked.
Jessie took a few seconds to reply.
“I said, bitch. Specifically, that little bitch Cheryl. I'm going to have to tell her she was right.”
Jack chuckled in a low masculine rumble.
“It's not funny, we had a bet,” Jessie said.
“What did you bet?” Jack asked.
“None of your business, I just hate losing.”
“Well, you seem recovered. Are you ready to keep going?”
“You still aren't done? I'm worn out.”
“I hope you aren't that tired. I was looking forward to having you ride me. I want to watch your tits bounce and jiggle while you fuck yourself with my cock,” Jack said.
Jessie raised a single eyebrow.
“I get to be on top?”
Jack nodded.
“Do I get to be in control?” she asked.
“Do you want to be?”
Jessie looked thoughtful for a moment.
“No, you're calling the shots. I'm liking that a lot.”
“Be careful, the other things I like tend to be more kinky.”
“So? If they make me feel half as good as what you've already done I'll be happy to be your kink whore and do whatever you want.”
“Are you sure?” he asked.
She nodded.
Jack laid down on his back.
“Come over here and mount me. Take my cock in your cunt and start riding me.”
Jessie swung one of her long legs over him and wriggled her hips as she settled down onto him. Jack's cock slid all the way in this time and Jessie started riding him, her warm, wet cunt caressing his cock with every movement.
Jack stared, entranced, at the movement of her breasts. He wanted to reach up and grab them, but worried that he'd set her off again and cause her to stop moving. So he contented himself with watching the nearly liquid movement of her breasts as they swayed.
After a few minutes, Jessie started slowing.
“Are you going to cum for me?” she asked.
“Not yet.”
“I'm getting tired, I don't know how long I can keep going here.”
“There are two things you could do that might make me cum. If you do them both together, I won't last another three minutes,” he said.
“Just tell me what to do,” she said. “I don't know how much I've cum, but it's your turn now.”
“Okay, I want you to talk dirty to me while you ride me with my cock in your ass instead of your cunt.”
“You want your cock in my ass?” she said.
“I want to fuck your ass, yes.”
“I already feel like you stretched out my pussy, but sure, I always wanted to get fucked in the ass but Eddie told me it was gross and nasty. He told me to never mention it again.”
“Then ask me to fuck your ass, I'll like that.”
Jessie sighed.
“Jack, would you fuck my ass? Pretty please?”
“I'd love to, but this time you're going to fuck your own ass, using my cock. Now do it.”
Jessie lifted herself off his cock, her hand went to his shaft and guided it to her asshole. Then she lowered herself down.
Her ass was as tight as could be. Jack was sure he was her first in that hole and he grinned at the thought. She grunted as his head slipped inside of her and her mouth let loose a torrent of filth.
“Fuck yeah, fuck my stinking asshole. Fill me up, make your cum drip out of my ass. I always wanted to be a slut, I guess I get my wish now. I can feel every last inch of you forcing its way into me and it hurts so good. I love it!”
She had half of his cock inside her ass when her body tensed and she let out a strangled scream. Her legs stopped supporting her and she dropped, driving him deeper into her ass. The drop did something to her and she started thrashing around on top of him. Jack reached up and drew her down against his chest, stopping her wild gyrations.
He couldn't resist, he started thrusting in and out of her. They were tiny thrusts, only as far as he could get by rocking his pelvis, but her reaction was all out of proportion. Her thrashing became more focused as she tried to drive his cock farther i
nto her. She kept slamming her ass into him as she tried to get him deeper.
Jack felt her nipples digging into his chest. They were rock hard and larger than earlier on. He could feel the juices running out of her pussy and down his skin. She was muttering something that he couldn't make out. He stopped his thrusts and just stayed still. In a couple of minutes she stopped thrashing.
“I can't keep doing this Jack, I'm sorry. I want to, but my legs are rubber and I'm so hyper-sensitive everywhere that the slightest motion is going to send me back to la-la land.”
“Want me to take over again?” Jack asked.
“Yes, and don't stop until you cum. I'll be gone again as soon as you start thrusting. Ignore that and just pound me until you fill me up,” Jessie said.
Jack's answer was to clutch her torso to his chest and roll them over so she was on the bottom. That alone was enough to set her off again, but Jack took her at face value and just started slamming into her ass.
His cock was clutched over and over again as she came beneath him. Her ass was convulsing around him so much that there was no prayer of not cumming quickly. It was less than two minutes before he felt himself swell up and just let go.
The next few minutes were a bit blurry for him, but when he could think clearly again he was still buried in her ass and felt the occasional ripple that told him she was still going. He slid himself out and bodily rolled her over so she was on her back.
Jack spent the next ten minutes sucking on her rock-hard nipples and playing with her clit anytime it looked like she might finally finish cumming. He only stopped when she managed to speak.
“No more, please. I can't take any more. Please stop?”
He flopped on his own back beside her. His hand crept out and settled on the soft skin of her thigh. They lay side by side for a while until Jessie stirred.
She sat up and he heard a sharp intake of breath.
“Oh shit, my kids are home in less than an hour. I've got to get moving. I need a shower and I need to get dressed again.”
Jack sat up, feeling as though he'd bruised his abdominal muscles.
“I'll just get my stuff and get going then?” he asked.
Jessie leaned down and kissed him hard, her tongue slipping into his mouth.
“That would probably be for the best,” she said after breaking off the kiss.
Jack started rounding up his clothes. Jessie grabbed hers and left the room. When she returned Jack was fully dressed. She was still nude, but didn't have her clothes any more.
“I left a little something for you on top of your bill,” she said.
“Thank you,” Jack said.
“What do you think, can we make this my normal delivery day? Probably after lunch though, otherwise I'll forget to eat like we did today.”
Jack stepped in to wrap his arms around her nude body and kissed her hard. As he moved back, his hands brushed the sides of her breasts and she shuddered.
“I'll block out the afternoon for you,” he said. “See you next week?”
“Yes, please,” Jessie said.
* * *
The End
of the MILF Man Deliveries Series
* * *
Other stories by Holly Ardent:
MILF Money for College (completed series)
Stand Alones:
The Prude's MILF (Cheating Wife MILF Erotica)
Serviced with a Smile (MILF Erotica)
Bartering Herself (Post-Apocalyptic Older Woman/Younger Man Erotica)
Cleaning Pan's Pipes - Mythological Erotica
Find Holly's other stories that aren't listed here on her Amazon Author Page:
Holly's Amazon Author Page