Valentine Virgins: Three Erotic Stories
By
Kali Lowe
Valentine Virgins: Three Erotic Stories
Copyright 2012 Kali Lowe
Smashwords Edition
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Anal Favor
Valentine's Day was when everything changed for Mark and Alisa. Sounds sweet, doesn't it? It didn't start off that way.
Alisa had invited Mark over, saying only, "I need to ask you something." She refused to explain more, but he came right over anyway. They had been friends for years, through middle school, high school, and now into their first year of college. Best friends, he would say. They were inseparable, and had managed to never screw up their friendship by trying a closer relationship.
Well, they were slightly less inseparable these days, since Alisa had finally gotten a boyfriend. She spent a lot of time with him, as Mark supposed was proper. He missed her, though, and he was glad she had invited him over.
She answered the door with a smile, and led him up to her bedroom. This was not unusual. He'd been in there a thousand times, to the point where her parents didn't even bother making her leave the door open. Everyone knew they were just friends.
She was wearing a pair of small denim shorts and a band t-shirt that stretched tight over her breasts. She'd started dressing that way since she got her new boyfriend. She was even letting her hair grow out, and had started lightening it from its natural dirty blonde color. The tomboy Alisa of a couple years ago would have laughed at her. Mark, for his part, just tried not to get caught staring at the girl he used to affectionately call "just one of the guys."
Alisa sat down on the edge of her bed. Mark settled in beside her.
"Mark, I need a favor," she said.
"Sure. Anything."
Alisa looked down at her hands, "It's about something I want to do for my boyfriend. Like a Valentine's Day present."
He smiled. "That's cute. Well, how can I help?"
There was a long pause. "Anal sex," she blurted out. Her face immediately turned bright red.
Another lengthy pause followed. "I'm sorry?" he said.
She took a deep breath. "I promised him anal sex. He kept wanting to and I kept saying no, but... I really like him. I should be able to do this for him."
"I, um, I didn't... I didn't know..." He stopped himself and started over, telling her seriously, "You shouldn't do anything you don't want to do."
She shook her head. "It's okay. I've decided. But... I'm not sure I can do it. I mean, I've never done anything like that. And I... I don't want it to be bad after he's waited so long, you know? I want to know it'll be good. But I just have no clue what it'll feel like or anything."
"Sure. Um." He thought for a moment, and soon reached a conclusion. One that obviously couldn't be true. But he felt his cock twitch. Calm down, he told himself. This is Alisa. Your best friend. "So, um. What do you need me for?"
She looked up at him, her blue eyes staring into his. "You trust me, right?"
"Of course, absolutely. I love you, you know, as a friend. I'd do anything for you."
"I need... I need to know how it feels. I need to know I can do it."
He paused. A wrong assumption here could make him sound like a big perverted jerk. "Feel what?" he asked cautiously.
She let out an explosive breath. "Don't make me say it again!"
"Anal sex."
She nodded.
"With... with me?"
"Um. Well. Yes."
"Alisa..."
"We don't have to like, totally do it," she explained hurriedly. "Just... put it in. So I can feel it. Then we'll stop. And we'll pretend it never happened." She reached out and took his hand in both of hers, staring pleadingly up at him. "Please? For me?"
He stared back at her, thinking of baseball games they'd played together as teenagers, times they'd wrestled playfully. Watching movies with her on the couch, leaning against each other, totally platonically, just enjoying each other's company with no pressure to do anything more. Were they going to lose all that? Was it really as simple as she made it sound?
He thought then of less innocent things. The accidental handfuls of ass or tit he'd sometimes grabbed while wrestling with her. The way she'd pull her bra out from under her shirt before cuddling up for those movies, so she could be totally comfortable. The wet dreams he'd had about her and never even considered telling her about.
"Okay," he said suddenly. "You're my best friend and I trust you. I'll do it."
She grinned and threw her arms around him for a tight hug. Then she drew back, her grin fading. "Um. Now what?"
"You want to do it right now?"
She nodded.
Mark cleared his throat. "I've never done this before either, you know. But... I know we need lube."
She nodded again, then leaned over him to open the drawer to her nightstand. He would usually pay little attention to her body brushing against his; she got that close to him ten times a day without thinking anything of it. But today was different. His cock stirred as he felt the heat of her body.
She pulled out a bottle of lube then settled back beside him. She held it up. "I bought this. Will it work?"
He eyed the tall, thick bottle of clear lube. He imagined her going up to a cash register with that and struggled to keep a smile off his face. He nodded. "Yeah, that should do it."
She handed it to him, then turned and crawled up onto her bed. She looked back at him, an embarrassed smile on her face. Then she sat up long enough to unbutton and unzip her shorts. She eased them down slowly, along with a pair of plain black cotton panties. His breath caught as he watched her naked ass come into view. She'd mooned him a time or two, trying to be funny, but this... this was a little different. He felt his dick grow rock hard. She stopped her shorts there, exposing her ass while keeping her pussy covered. That was something he'd never seen.
He crawled onto the bed behind her and knelt there, a few inches away from her ass. He almost reached out to touch her, then thought better of it. They had a specific purpose here, after all. It might freak her out to do anything more than he had to.
He lifted the bottle of lube a couple inches above the cleft of her ass, then squeezed, letting the clear slippery liquid dribble out. It landed on her pale skin, right on her tailbone, then started to drip down between her firm cheeks. His had to adjust himself in his jeans as he watched it glide over her pucker, leaving the tiny hole glistening in its wake. She shivered at the same moment.
"Is it too cold?" he asked.
She took a breath. "A little. It's... it's okay."
He hesitated. "Should I rub it in? You know, to warm it up?"
"Okay, sure."
He dribbled some more lube onto her cheeks, watched it drip down her smooth skin for a moment, and shivered faintly. He couldn't believe she had such a cute, tight ass. He leaned closer, moving carefully so that his erection wouldn't brush against her. He was a bit surprised himself that he was so hard and ready for his best friend. He had no idea what she would think of it.
"I'm going to touch you now," he said. She had no response, so he proceeded.
He placed his hands on those firm cheeks, and began slowly rubbing the lube in, feeling it warm against his palms as it smeared over her skin. He hesitated for a moment, then slowly slid his fingertips down between her ass cheeks, gliding it through the lube dripping there, feeling the bump of her little rosebud. Alisa drew a breath and shivered.
"You okay?" he asked.
"Yeah," she breathed. "Sorry. Keep going."
"Okay. I, um... I think we should try a finger before... you know."
"Okay."
He rolled his index finger slowly in the cleft of her ass, coating it with dripping lube. Then he slid that finger down, finding her small pucker again. He moved it in slow circles, tracing the circumference. Then he centered his fingertip on it and pressed gently. He felt it just beginning to give, the lube letting his fingertip push in a little. He saw her fingers tighten on her bedsheets.
"Still okay?" he asked.
"Yeah." It sounded like she was breathing a little faster. "Go ahead."
He eased his finger in and out, going slow and occasionally adding more lube. He moved it in slow, easy back and forth movements, letting a little bit more of his finger enter her every time. Her asshole clenched around his finger, and he shivered, wondering how his cock would even fit in there. But gradually she relaxed, and he thrust his finger deliberately in and out, pushing the lube into her as the movements became easier.