My approach had to be just right to get into Cindy's panties. Otherwise, my 19 year old sister would run scared. Don't misunderstand, it's not totally selfish of me. Sure, I want her to kiss me with her tongue, suck my tits and put her mouth on my pussy to give me mind-blowing orgasms. But it's also for her.
You see, my little sister has a hard time with sex. She's only been with one guy, who fucked her at a party right after she turned 18. It was consensual, but she says it was painful and awkward. She (and I), are both on the pill, so at least there was no worry when he shot his load inside her. But it totally soured her on the idea of sex - totally.
Things have been very different for me. I was still a virgin, away at college. But recently, I experienced such a sexual awakening that I couldn't wait to share it with her, to wake her up to the pleasures I've felt.
You see, my best friend, Melissa, told me of the lesbian love affair that she'd had with her sister, Karen. As she shared it with me, I got so turned on that we could barely make it to her apartment before enjoying each other's bodies.
Before now, I would never have imagined any kind of incestuous relationship. Karen and Melissa's story changed my mind. Their love and acceptance of each other, plus the incredible sex, lured me in. I started fantasizing about Cindy. More than once when Mel was going down on me, I imagined what it would be like if it was Cindy's tongue thrusting into my pussy.
After the term ended, I returned home for the summer to spend time with my folks, Cindy, and our younger brother Craig.
On one of the first days, Cindy and I were sitting out in our large backyard, watching the birds and squirrels play in the trees.
"You seem so much older now," Cindy said, lazily pushing our porch swing back and forth in the light breeze.
"I guess that's a compliment?" I said.
"It is," Cindy said, looking over at me as we sat together. "I can't put my finger on it, but you seem older than 21. Something's definitely changed about you."
Perhaps this was the opening I'd been waiting for.
"Well," I said, not sure how to begin. "I am a lot different, and not because of college. That's fine, but..."
"But what?"
"It's something pretty personal, but pretty great too," I said.
We've always been close, Christy. You can tell me anything."
I sighed. Here went nothing, or maybe everything.
"It's Mel. You know."
"Of course!"
"She and I, well, we've become super close. I mean, as close as anyone can be. We, um, we..."
"You what?"
"We became intimate."
Cindy's eyes got wide. "You had sex with Melissa?"
I nodded. "It was so awesome, Cin, really awesome."
A look of sadness crossed her face. "Glad for you, I guess."
I turned to her and took her by the shoulders. "I know how tough it's been for you. It's made me sick inside that your first time was so bad, but..."
"But what?" Cindy said.
"I don't know," I said, sighing again and sitting back down, staring at the trees. "You know how inexperienced I've been when it comes to sex. I guess it's just that Mel introduced me to feelings - feelings I've never had. And I thought that maybe there's a chance for you too - to feel good things. To have a woman... oh, never mind. Sorry I brought it up."
We sat silently on the swing, the summer sun casting shifting shadows across our faces through the leaves.
After a minute or so, Cindy reached over and grabbed my hand. I looked down at her hand holding mine, then up into her eyes.
"Thanks, Christy," she said, looking directly at me. "I guess I'm just not sure there's any pleasure to be had in sex for me."
"Oh but there is!" I said, smiling. "You just got off to a bad start, that's all."
There was another long pause. Cindy looked out again, lost in thought.
"You know," I said carefully. "You don't have to be with someone to have pleasure. You can do that yourself if you want."
"You mean masturbation?" she said.
I nodded. "Yeah, self-pleasure."
"I don't know," Cindy said, still holding my hand. "I, um, I wouldn't even know what to do."
"Well," I said carefully. "I could show you."
"You mean like, tell me how?"
"Not exactly," I said. "There's a better way."
"Oh, like do it... yourself?"
"Yep, that's what I mean."
"You'd do that for me?"
"Of course!"
"But... where... when?" Cindy said.
"How about right now?" I said. "No one's going to be home for quite a while and it's really private back here."
Cindy looked around. "I guess you're right," she said.
"You know I'm going to need to lose some clothes, right? I can't do this through fabric," I said.
Cindy nodded. "I figured."
"So the first thing you need to understand is that pleasing yourself is as much mental as it is physical, especially for a woman. So when I want to get myself off, I picture someone or some situation in my mind - something that'll start to turn me on."
"What are you going to think about?" Cindy asked.
"Well," I answered. "Probably about Mel coming on to me and leading me into her apartment and French kissing me."
I closed my eyes and leaned back against the cushion. The thought of Melissa would certainly have turned me on, but that's not the person I was thinking about. Not that I would tell Cindy that it was her that was on my mind. At least not yet.
I pushed off my shorts and began rubbing my pussy through my panties, using a gentle back and forth motion. I opened my eyes and saw Cindy staring at my hand.
"Umm, that's feeling nice," I said. "I'm starting to relax now."
I put my fingers underneath the waistband of my panties and ran them across my dark bush, lightly touching the top of my slit.
"I'm already getting wet," I said as my fingers opened my pussy lips slightly.
I began a slow up and down motion, running my fingers down my slit and back up to spread the moisture.
"I need better access," I said, taking my panties and pushing them down to my knees then kicking them off.
"That's your..." Cindy said.
"Yes, Cin, my pussy. It's okay if you see it, you know!"
I opened my lips wider and pressed into my clit.
"Ooh, yeah, that's it," I sighed. "I'm going to rub my clitoris."
I started thinking about Cindy touching me and I felt a shiver of pleasure go through me.
"You okay?" Cindy asked.
I opened my eyes again. "Oh yeah. I'm feeling really good!"