Story 17 #5
At the end of the day, he sent her down to the parking lot ahead of him as he gathered up his things. He tossed his papers and his laptop into his briefcase and threw on his hat and coat, turning off the lights and locking the door behind him. The custodial staff had keys to each executive office, so they could get in during the weekend and empty the trash cans, vacuum the carpets, and, if necessary, dust the shelves and wipe down the windows.
He waited a couple minutes and then headed down to the lobby via the elevator. He came back to his car as quickly as he could. Jodie was waiting by the passenger door. They smiled at each other as he double-clicked the key fob. He opened her door for her and closed it as she slid into her seat. He opened the back door and set his hat, coat, and briefcase in the back seat, circling back around to his seat to start the ignition. "Did you enjoy today?" he asked, peeking in the rearview and then backing out.
"I did, yes. I'm even more looking forward to tonight." She side-eyed him and smiled sweetly.
"On that note, I think I want to try something new with you tonight. Something that I saw in that video I watched this morning."
"Oh?"
"How do you feel about... an alternate mode of penetration?" Her brow furrowed for a moment and then rose with her realization of what he meant.
"I'd be willing to give it a try."
"Excellent." He smiled at her, focusing on the road for the rest of the ride. She was astounded as they pulled into his driveway.
"This is your house?" she said incredulously. "Daddy never told me how big it was."
"Well, 'Daddy' has never been to my house," he replied. "We only ever go out for beers or lunch every few months."
"You've been friends since college and he's never been to your house?"
"Not this house, no."
"How long have you lived here?"
"About 13 years." He paused. "Most of the people who visit my house are... one-time visitors, if you catch my drift." She furrowed her brow. "Most of them are women I bring home from clubs and have sex with and then they never come back." She nodded understandingly. He turned off the ignition and stepped out of the car ahead of her, circling around to open and close her door for her. She grabbed her things off the car floor. He presumed the bag held her overnight necessities and a change of clothes. He grabbed his things from the backseat and clicked the key fob.
They headed up to the front door, which he unlocked for her. "Now, do you want to go directly to the bedroom or take the tour?"
"We can always do the tour later," she said with a suggestively shy smile.
"Of course." They headed up the stairs and he led her into his bedroom. She sat down on his bed as he dressed down for the day. He put up his hat and coat, tossed his briefcase aside, and kicked off his shoes. He took off his belt and undid his tie, tossing the belt aside and sliding open the closet door to put away his tie. He undid his suit jacket and put it back on the hanger and shimmied out of his pants to put them on the same hanger. He then undid his button-down and tossed it in the wicker laundry hamper. He was down to his underwear and socks. Jodie had leaned back on the bed to watch him undress. He turned to look and smiled at her. "Enjoying the show?"
"Maybe..." she said, looking down. He walked over to the bed and put a hand on her cheek, forcing her to look at him.
"Not 'maybe.' Yes or no, sweetheart."
"Y-yes, sir." He unhanded her and chuckled, patting her cheek gently. She's so easy, he thought. It's adorable.
"Now," he said, sitting down beside her on the bed. "Have you ever experimented with anal?"
"I have a toy I use back there sometimes..."
"Oh?" He cocked his eyebrow. "What kind of toy?"
"An anal dildo."
"Mmm. How big is it?"
"About six inches and average width."
"So you haven't tried anything my size back there, but you kinda have an idea of what you're getting into." He put an arm around her. "Are you ready to give it a try?"
"Sure!" He wasn't expecting her to be quite that enthusiastic. She quickly undressed, unbuttoning and tossing off her blouse, unhooking her bra, and stripping out of her panties. This was the first time he had seen her undressed. He stood up to look her up and down. She was lean and slender, with a bit of muscle tone, and her breasts were small but not flat. Her nipples were a pleasant dark pink, matching her lighter skin tone. He grabbed her by the waist and pulled her in, kissing her deeply, aggressively slipping his tongue past her lips and brushing it against hers. She moaned into the kiss.
He gently pushed her down onto the bed, stomach-first. He pulled a small tube of lubricant out of the nightstand drawer and put it on one finger. He spread open her cheeks with one hand and rubbed the lube against the opening. He pushed the finger in, working it in and out until it felt comfortable. He added lube to a second finger and slipped that one in. She moaned into one of the several pillows on his bed, leaning back into his fingers to push them in deeper. He took her cue and shoved the two all the way in, down to the bottom knuckle, and worked them in and out, rotating them slightly, to open up her anal muscles and get her ready to take his cock. It did not take long at all for her to feel ready. He took a rag out of the same nightstand drawer and wiped his hand off. He dug around for a condom, tearing the package open and pinching the tip to roll it down his shaft. The condoms themselves were already lubricated, but he knew that it would by no means be enough lubricant to accommodate his entire cock in her relatively inexperienced hole. He generously lubed up the condom and rubbed a couple fingers' worth of excess lube against the outside of her opening.
"Are you ready?" he purred.
"Yes, sir..."
"Good." He climbed up on the bed and knelt behind her. He pulled her hips up and carefully aligned the head of his cock. He took it by the base and rubbed the tip against the opening, pressing it in gently until it made entrance. She whimpered slightly. He pulled it back out. "Are you okay?"
"Yes, sir. I'm okay. Please put it back in."
"Okay, okay," he chuckled. He rubbed it against the entrance again, pushing the tip all the way in. He gently thrusted back and forth, working his erect cock inside her half an inch at a time. She could only contain her moans by forcing her face down into his pillow. He pushed a little more assertively, thrusting the six inches she was accustomed to into her. She turned her head to the side and could no longer contain the moans within the confines of his pillow. She sounded like she was in Heaven.
He decided that she was ready. He pressed down on her more fully, shoving the remaining two and a half inches into her. She nearly screamed in pleasure. He could see that her eyes were tearing up, but she was clearly euphoric, savoring that feeling of fullness as he thrusted in and out of her harder, his heavy, low-hanging balls slapping up against her clit. He grabbed her waist for leverage and pounded into her as hard as he possibly could, making her fully cry and whine.
"You okay?"
"I'm good. Please don't stop." He did as asked and thrusted as hard as he could into her, slamming his cock into her hole without an ounce of mercy. She was clearly enraptured, so he focused on his own pleasure. The tightness was almost overwhelming, hugging his member so firmly that he could not take it much longer. He tried to hold back for as long as he could, to prolong the experience for her, but he could not.
Without much warning, his cock throbbed and twitched intensely. He involuntarily thrusted deeper into her. He could feel the muscles in his perineum and asshole twitching wildly. He must have shot at least eight full ropes of cum into the reservoir of the condom, far more than he ever came. His lower body was exhausted. He gently pulled out of her and carefully removed the condom, tying it off and tossing it in the trash alongside the wrapper. He collapsed on the bed beside her, rolling onto his side. She rolled onto her side as well to face him.
"Hey," he smiled, wrapping his arm around her and rubbing the small of her back tenderly.
"Hey," she smiled back.
"Do you want to do this again every weekend?"
"Yes, please."
"Good." He pulled her in close and she rested against his chest. They relaxed together, drifting off into a quick after-sex and before-dinner nap.
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