Unforgettable Weeks - Cover

Unforgettable Weeks

Copyright© 2015 by Jay Cantrell

Chapter 108

Drama Sex Story: Chapter 108 - Two people from vastly different worlds shared one crazy night two months earlier. Regan Riley learned that life is sometimes serious and Andy Drayton learned that life can sometimes be fun. Now they've decided to see if they can overcome their differences and forge a relationship. This is the sequel to "Unending Night."

Caution: This Drama Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Consensual   Romantic   First   Oral Sex   Exhibitionism   Slow  

1 a.m. Tuesday

Regan led the group up the stairs - making certain that Andy wasn't following anyone but her. He'd gotten enough glances between Ashlyn's legs for the night and she wouldn't put it past Tori to moon him.

The girls were on the third floor and Regan's room was on the second. She directed Andy to the room along from hers - where Camille had slept the night before.

"Seriously?" Tori asked, when she saw where Regan was putting Andy.

"Aunt Rita told us this morning that they didn't care if you had sex," Ashlyn added.

Regan frowned slightly. It was none of the girls' business and it certainly wasn't her parents' place to tell them anything about her sex life.

"It's not that simple," Regan said. "When we thought Andy would be staying Friday night, Dad told me that he wanted him to stay in a different room from me. Yeah, if I'd have asked, they probably wouldn't care. But I didn't ask and, well, they're too drunk to even remember tomorrow."

"So what?" Ashlyn said. "We don't care."

"And we won't say anything," Tori added. She lowered her head slightly, hoping Regan would understand that she hadn't said anything about what she'd seen Sunday afternoon.

"I know," Regan said - although she really didn't. "But I've worked really hard to gain trust and respect from Mom and Dad. I'll talk to them about it tomorrow but I don't want to risk them telling me 'no' later on because I didn't talk to them tonight."

"It's one night," Andy said. "We'll survive."

"Sure," Tori said. "I mean, it's not our business anyway."

"It's really not," Andy agreed with a wink.

Tori grinned at him but Ashlyn had to fight to keep from rolling her eyes. She knew he'd sneak across the room as soon as the "kids" were in bed. Or, he would if he had any balls.

Tori gave Regan a hug and then kissed Andy on the cheek.

"Good night," she said brightly. "I had a lot of fun tonight!"

Ashlyn repeated her sister's actions but, unlike Tori, she made sure to run her breasts across Andy's arm.

"It was pretty cool," Ashlyn said. "I'm sorry for being so grouchy. I'll try to watch it but let me know if I slip."

"Oh, we will," Regan assured her. She gave Andy a soft kiss on the lips and saw him into his room before disappearing into hers.

Ashlyn and Tori started up the stairs but Ashlyn put her hand on her sister's arm to stop her midway.

"A week's allowance says we hear a door open in five minutes or less," Ashlyn whispered.

Tori turned on the steps and narrowed her eyes while she rubbed her chin.

"I say they'll be all goody-goody. You say one of them will sneak into the other's room. Right?" she said.

"Yeah," Ashlyn said.

"Let's make it interesting," Tori said, eyeing her sister closely.

"What do you have in mind?" Ashlyn asked, curious about what was crossing her sister's furtive mind.

"If I win, you kiss my bare butt - right here and now and again in front of them tomorrow morning," Tori said.

"That's gross," Ashlyn said. "I'm not doing that!"

"Not so sure of yourself when the stakes are tough," Tori taunted.

"Fine," Ashlyn said. "But if I win, you have to do the same to me."

"Deal," Tori said, extending her hand. Ashlyn shook it. "I'm going to hold you to the bet. Five minutes ... starting now."

The sisters sat down on the stairs and Ashlyn set the timer on her phone.

Regan gave the sisters time to get upstairs before stripping off her clothes and walking into her closet. She moved some shoes out of the way and unlocked the door on the other side. Andy was standing in his boxer briefs looking at her when she stepped into his room. He saw she was wearing only the dark blue cotton thong he'd watched her pull up her legs that morning.

She put a finger to her lips and then gestured him into the closet with a huge grin.

"The rooms are supposed to share the closet," she said softly.

She pulled him into the closet and to a padded bench. She sat down but pulled him in front of her when he tried to sit beside of her. She shook her head as she lowered his underwear. It was one of the few times she'd seen his dick semi-erect. A simple touch of her hand rectified that situation.

Regan dipped her head forward and put the head between her lips. She pulled back and let her tongue circle the head before lifting his erection upward and running her tongue down the stalk to his balls.

She had never done much with his sac before but decided then seemed like a perfect time - particularly because the mirrors in the room let her watch exactly what she was doing. Her breasts started to tingle as she watched herself pull one of Andy's testicles between her lips and suck on it lightly.

The groan that escaped Andy's lips made it even more exciting for her. He bent forward to cup one of her tender breasts. She hoped he would be interested in making sure she got off, too. She saw her smile in the mirror. Of course he would. He loved her.

Regan decided this blowjob would be one they both enjoyed. Andy enjoyed the sensations below his waist; Regan enjoyed watching Andy's dick sliding between her lips. She made sure Andy's dick was wet when she ran a hand along it. The hand continued downward until she found her own pleasure center. She slid forward on the bench and tugged the thong to the side. It wasn't exactly comfortable but it allowed her to play with her clitoris without hindrance.

Despite Regan's best intentions, Andy couldn't hold off. She felt the first spurt hit her tongue before she had reached her climax - but she knew her time would arrive soon enough. She used one hand to milk the last drops into her mouth and the other to fondle Andy's tight sac.

She looked up at him and licked her lips before putting the head of his dick back in her mouth for a moment.

The look on her face when their eyes met again was entirely different from a few seconds earlier. The sexy vixen had been transformed into a grinning minx.

"Like that?" she asked.

"Always," Andy replied as he tried to catch his breath. She patted the seat beside her and Andy sat down. Regan stood and pushed her panties to the floor where they rested next to his. Then she crawled on his lap.

"It's going to take me a second," Andy said. Regan only shook her head.

"Not tonight but maybe tomorrow morning in the shower," she told him. "For now, would you suck on my nipples while I ... I play with myself?"

"Sure," Andy answered. "I can play with you though."

Regan looked at him. She didn't like to kiss him after he'd cum in her mouth but she made an exception this time. His finger went between her legs and he found her dry. Regan broke the kiss and pulled his finger to her mouth. She sucked on it for a moment before releasing it. Then she put one of her own fingers between her lips. Her finger joined Andy's between her legs. She understood that Andy knew what she liked as well as she did. The sensation of having a pair of fingers tracing circles on her tender bud caused the air to leave her lungs.

She moaned when Andy leaned forward and captured a nipple between his teeth.

"Bite it a little," Regan urged as she watched him in the mirror. She had watched him from above every time they'd been together. The perspective from the side was different. She decided at that moment that they would make a video together - soon. Regan re-wet her finger before drawing Andy's back to her lips. She pulled her free nipple while he alternated biting, sucking and running his tongue over the other.

Andy felt Regan start to buck against his hand and shifted his hand forward until the palm rested against her clit. He bit down on her nipple lightly just as he slapped her on the butt. The sound was more impressive than the feeling but Regan had to pull her hand off her breast to cover her mouth to keep from screaming out in pleasure. Andy released his hold on her nipple and she pulled her hand from between her legs. She grabbed his face and kissed him deeply, her tongue plunging into his mouth as she rode his palm through her crest.

She continued to kiss him as she came down from her high. He had known exactly what she wanted - what she needed - and he'd given it to her. The only thing she missed was that the finger resting against her butthole hadn't penetrated her there.

"Enjoy that?" Andy asked with a grin when she sat back on his knees. She didn't answer. She just grabbed his palm and lifted it to her face. She had planned to lick but changed her mind when she saw it was covered in menstrual blood.

"Yuck," she said. "Let me get you a towel."

Andy wrapped her arm around her to keep her in place.

"It'll wash," he said. "I want to kiss you some more."

As Regan started moved her lips back to Andy's, Ashlyn was upstairs scrubbing her lips. She had tried to welsh on the bet only to have her younger sister tackle her. Tori had pinned Ashlyn to the floor, pulled the back of her pants down and put her butt on her sister's face for almost a full minute.

"Kiss it or I'll stay here all night," Tori taunted.

Ashlyn had grudgingly puckered her lips and Tori had let her up with a smirk.

"I've always known you were an ass-kisser," she said. "Tomorrow morning, if I have to tackle you again, I'm going to make you kiss the hole."

"Bitch!" Ashlyn hissed.

"And don't you forget it," Tori said with a nasty laugh.


"You didn't think I was going to let you sleep alone, did you?" Regan giggled as she cuddled up to Andy in her bed.

"But, you said..." Andy started.

"Ashlyn would have found some way to hold that over our heads," Regan cut in.

"I thought ... I thought she was actually pretty cool tonight," Andy said.

"Oh, you poor boy," Regan chuckled. "A girl gives you a glimpse between her legs and all of her sins are forgiven."

"I didn't mean to look!" Andy said.

"You wouldn't be a guy if you didn't look," Regan said. "Half the fun of tonight was watching those two try to flash you thinking I didn't notice."

She felt Andy's chest rise as he sighed and she chuckled again. She sat up on the bed - cross-legged as Ashlyn had been. Regan had on a new pair of panties but Andy still looked.

"See?" she said. "It's a natural reaction for a guy to glance there when a girl sits this way. The same way you're always going to look down an open shirt. It's not personal. I know that. It's just a natural reaction."

She resumed her spot on Andy's shoulder, knowing he was more confused than ever.

"They're playing a game," Regan said. "They don't think I know so it's funny for them. But I do know so it's funny for me, too."

"It isn't funny for me!" Andy said.

"Sure it is!" Regan said. "You got to see a new pussy and two fresh boobs tonight. I thought it was every guy's goal to see all the boobs and pussies in the world."

"You're pretty casual about all this," Andy noted. Regan rolled on top of him and looked down at him. Her nipples were against his warm skin and she felt a fresh flush of arousal.

"You're damned right I am," she said, biting her lower lip. "I've got you. You're mine and I'm yours. Those two can show you anything they want and nothing is going to change that. Tell you what: You have my permission to go upstairs and fuck either one of them. Hell, do them both if you want. I will never say a word about it."

"Yeah, that's bullshit," Andy replied.

"No," Regan said. "If you really want to do them ... go do them."

"I don't," Andy said.

"I know," Regan said, smiling at him. "You'd rather lay here next to my bloody coochie than go upstairs and sample two fresh ones. I know that, Andy. You know how I know I got you?"

She didn't wait for an answer but let her eyes bore into his while she continued.

"Tonight, when they pushed their boobs at you or flashed their coochies at you, you didn't ... get hard," she said. "But anytime I was near you, you started to get erect. I could bring them down here to give you a lap dance and you'd be soft when they were done. I could go into the bathroom, put on a shower cap and a robe, come back and curl up next to you and you'd be like this."

She reached down between her legs and ran her hand over Andy's hard dick.

"Do you have any idea how that makes me feel?" she asked.

Andy didn't understand the question so he remained silent. It wouldn't have mattered because Regan was talking again before he could have gotten a response out.

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