Greg O'Connor had just gotten home and was nibbling on a piece of fried chicken his mother had cooked earlier. He wasn't very hungry as he had eaten a burger about thirty minutes before The Shake Shack closed. He had been working there for about six weeks now and really liked it, especially considering that this is where he had met his current girlfriend, Cindy-Lou McIverson. The two had been dating just three weeks, but Cindy made an announcement tonight that had Greg both excited and nervous. He thought to speak to one of his friends concerning Cindy's words, but chose instead to speak to another woman, someone whose advice he knew he could trust implicitly. He washed up, then made his way to his sister's room. He knocked lightly, and when the invitation to enter was given, he did so.
"Hey, Greg. How was work tonight?" Alyssa asked just above a whisper due to the fact that their parents were already asleep.
"It was okay," Greg said as he sat at the foot of her bed. "I need to talk to you about something, though."
"Sure," Alyssa said. "Go ahead."
"Well, it's just that Cindy told me tonight that she's ready to take things to the next level," Greg began.
"Sex?" Alyssa questioned.
"Yeah, but just oral," Greg responded, then laughed. "I say
just
, but that's a pretty big deal, huh? I've never done anything like that before, Alyssa. As far as that goes, I've never had anyone do that to me. I'm still a virgin. What if I suck at it and can't get her off?"
"Hmmm," Alyssa said as she sat up a little straighter in her bed. "You're right. A woman places a lot of value on someone's ability to get her off orally. That's the reason I date older guys, because guys my own age don't know their way around a clit."
Greg snickered at that, then asked, "What should I do?"
"I guess you could watch some porn," Alyssa suggested, "only stay from male-female porn. Watch lesbians. They do it the right way. Try Girlsway. It's full of stuff like that."
"You really think that'll help?"
"Couldn't hurt," Alyssa responded. "Watch what they do, try it out on your pillow ... You'll be awesome at it in no time."
"A pillow doesn't give feedback," Greg pointed out, "so the whole idea of 'practice makes perfect' doesn't apply."
Alyssa thought on that for a few seconds, then said, "Okay then, practice on me."
"What?" It was the same kind of incredulous response one might expect after being told that WWE owned the Olympics and all the outcomes were fixed.
"Sure. Why not?" Alyssa continued. "Jack is still out doing his National Guard stuff and won't be back for another couple of weeks. I'm pretty horny. You need to practice this to impress your girlfriend. I'd say the planets have aligned in your favor, little brother." Greg just stared at her. "So, are you in, or out?"
"Uh ... In, I guess?"
"Go on and get your shower and come back when you're finished," Alyssa directed Greg, and he left to do so.
His knock on her door was even more timid than when he first arrived home, so nervous was he. She told him to enter and close the door behind him, and once he had, he was standing in near-complete darkness. Then a soft light filled the room. It came from Alyssa's small reading lamp. She told Greg to have a seat where he was before, and he did.
While he was getting his shower, Alyssa wondered if she should put on some sexy lingerie. She thought it might enhance the moment, but there was really nothing romantic about this. It was just Alyssa giving her brother lessons on how to eat pussy, which is why she didn't have candles burning or soft music playing, either. She opted to just leave her pink panties and matching pink teddy on, knowing to a first-timer like Greg that this would be enough.
"So," Alyssa began, "Are you ready for your first lesson?"
Greg nodded, then a shaky, "Yeah," escaped his lips.
Alyssa pulled the cover off her body, then lay back and said to her brother, "Remove my panties for me, please."
Greg reached out apprehensively, and with nervous fingers he pulled her panties off her. "Oh, shit," he whispered as he caught sight of his sister's pussy, a lily-white wonder of beauty with a dark landing strip of hair manicured just above the clit.
"What do you think?" Alyssa asked.
"It's beautiful," Greg answered truthfully. This was the first time he had ever seen a pussy live and up close. He had seen hundreds on pornos, but at this moment, none of them compared to his sister's.
Alyssa smiled. "Okay, lesson number one: I want you to name all the parts of my pussy."
"Huh?" Greg grunted, and when Alyssa repeated herself, he just shrugged, but he did as she asked. "Okay. Um, this is your pubic hair, what little you have of it. This is your clitty. These are ... Um ... pussy lips, and these ..." he began to laugh. "These are bat wings, at least I think they are. That's the only word I've ever heard to describe them, anyway."
Alyssa smiled at that, for she had heard the same. Even still, "You forgot my clitoral hood, the 'lips' are actually called 'labia majora,' and the 'bat wings,' or slit, is called 'labia minora.' I want you to know this because there is more to a woman's pussy than just what you see. Every bit of it is as sensitive as your penis, if not more so, which means that every bit of it deserves attention, not just the clit. Understood?"
"Yeah," Greg answered.
Alyssa was going to have her brother try to eat her on his own , without direction, but the more she thought on that the more she knew the result would be akin to watching grass grow, for her, anyway, so she called an audible and said, "Come up here, Greg. Lay down with me." He did so, and very humbly refused to meet her gaze. She placed a finger under his chin and drew his head up. "It's okay. You can look at me." He smiled. "There's more to eating pussy than just eating pussy, Greg. You can't just get down there and do it. You have to build to it. It's all about seduction."
He nodded his understanding.
"Do you think I'm pretty, Greg?"
"Yeah." It came out as a breathy whisper.
"Then tell me so."
"Alyssa, you're one of the most beautiful women I've ever known. Just to be here with you right now, like this, is something I will cherish forever."
She smiled. "Thank you, Greg. Knowing that makes me feel I am special." She then leaned in and softly kissed him on the lips, but he kissed her with his lips closed, like one would kiss a relative. "No, Greg. Not like that. Kiss me the way you kiss ... Cindy, is it?"
Greg nodded, then closed his eyes, then parted his lips as he moved in closer to his sister. Their lips met, then he slowly inserted his tongue into her mouth. Alyssa latched onto it and began to suck it like it was a miniature dick, then she released it and allowed her own tongue to enter Greg's mouth. He sucked hers as well, then they both found a rhythm of lips only softly going up and down, light smacking filling the air as they did so.
Alyssa pulled back a little and said, "Kiss my neck."
This was something Greg knew he was good at. He went to the side of his sister's neck and began to softly lick and suck. Not hard enough for a hickey, but enough to elicit the response he had hoped for.
"Oh, yes," Alyssa sighed. "That's the spot. Right there." She moved a hand behind her brother's head and gently held him in place. She craned her neck a little more, giving him ultimate access. If he had been on top of her, she would have enveloped him with her legs. "Take my top off." Her voice was so husky that she hardly recognized it as her own. She arched her back, then lifted her shoulders up, and that was all there was to Greg removing her teddy top.
He began kissing her lips again, then moved his right hand to her left breast. He immediately felt her nipple harden even as he wondered how something so soft could be so firm. Greg slowly kissed his way down and made a beeline for Alyssa's nipple, but she stopped him. "Don't assume that the nipple is the only party of the breast that's sensitive. Just like a pussy, sensitivity is throughout. Take your time with it. Kiss every part of it. Let the nipple be your destination but enjoy the journey as you build toward it. Believe me, Cindy will appreciate that."
Greg nodded his understanding and began softly kissing every part of Alyssa's pert, small breast. He spent what he reckoned a good five minutes kissing the sides, the under-boob, and above the nipple before taking the nipple itself into his mouth.
"Oh, yes," Alyssa softly moaned. "That's it, Greg. Suck it lightly. Nothing too rough." She allowed him to suck it for all of a minute, then said, "Lightly gnaw it. Oooh. Yeah. Just like that. Now flick your tongue on the end of it." Her hand had found the back of his head again, and she held him in place as he continued to send tiny shockwaves throughout her body. She was aware that she was wet between her legs, but as much as she wanted to shove his face down there, she had to remind herself that this was a tutorial.
"Move to my right breast now." He did, slowly, taking care to ensure she benefitted from the move. "Now lightly tweak my left nipple." He pinched it. "Oh! Oh! Yes. Just like that."
Greg thought that his sister might be overselling her excitement, then again, there was something in her labored breathing to suggest she was being genuine.
Alyssa whispered, "Lightly run your hand from my breast to my pussy. Take your time. There's no rush."
Greg did as directed, and upon finally settling between her legs, near-shouted, "Damn!"
"Shhhh!"
Whispering, he said, "You're really wet down there."
"Keep lightly rubbing like you were," Alyssa commanded him, so he did. After a few minutes of this, however, she said, "Place your palm on my clit." After he had done so, she said, "Apply some pressure and move it in a circular motion." Greg did, and about thirty seconds in Alyssa whispered, "Don't stop." Another fifteen seconds and her legs moved wider apart as she said, "I'm almost there." Ten seconds more and it was all she could do to contain her yelp of pleasure as she achieved her first orgasm of the night. Panting like an overheated animal, she said, "Oh, God, that was great. Thank you, Greg."
"I really made you cum?" he asked in disbelief.