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!"
I kept watching Cindy as I pulled off my t-shirt. I wasn't wearing a bra that day. I noticed her eyebrows went up as she saw my nipples. I started tweaking one nipple as I put my other hand back on my pussy.
My hips began to rise and fall with the rhythm of my fingers, moving faster now across my clit. My breathing started to get more rapid and shallow and I began to moan.
Cindy was entranced, her eyes going back and forth between my breasts and my now swollen pussy. I could smell my scent in the air and wondered if she could too.
"Shit, I'm getting really fucking turned on!" I said as my speed increased. "See, oh, yeah, see, I'm using a really light touch on my clit. Now I need to, mmm, put some fingers into my pussy."
I put first my index and then my middle finger into my hole and a fresh amount of pussy juice dribbled out. I alternated between fingers in me and a finger on my clit.
"Oh shit! Oh shit!" I said as my mind pictured Cindy sticking her fingers into my pussy and kissing me.
I could tell it was having some kind of affect on her as I noticed her nipples sticking out from underneath her t-shirt. She wasn't wearing a bra either!
"Are you close?" she asked.
"Oh fuck yeah. Oh fuck yeah. Oh, oh, oh... shit!"
My pelvis suddenly lifted up in the air, I took in a breath and held it while furiously rubbing my clit. I then felt an orgasm explode through me.
"I'm cumming! Shit! Ahhhhh!" I cried and my legs started jerking and spasming as the pleasure washed over me.
What was most incredible, was that I came while looking right into Cindy's eyes. What a rush!
I finally came down from the high and gently ran my finger up and down my slit, slipping a finger into my vagina and spreading the juices all over.
"Wow!" Cindy said. "You really came!"
"Oh yeah I did!" I said, my breathing starting to slow a bit.
Almost without thinking I took my fingers out of my pussy and put them in my mouth, tasting my own juices.
"What are you doing?" Cindy asked.
"Oh shit, sorry!" I said, removing my fingers. "Force of habit I guess. It tastes really good, though. You should try it sometime!"
Cindy just kept staring at my body, her nipples rock hard under her shirt. She looked kind of flushed too.
"Thank you," she said finally. "Maybe I will try that sometime. You helped."
"My pleasure," I said, really meaning it!
I got dressed and we both went back in the house. I noticed that Cindy spent much of the rest of the day in her room with the door closed. I hoped I hadn't gone too far with her.
The family all had dinner together and watched a movie until late. It was nearly midnight when we said our good nights and headed for bed. Not a word from Cindy on what we'd done that morning.
The next morning, my brother Craig, and my parents headed to their jobs.
Only a few minutes after they left, Cindy came and joined me on the living room couch.
"Well?" I said. "Did you try anything?"
Cindy looked crestfallen. "It didn't work!" she said, in an almost desperate tone.
"Oh Cin!" I said, and drew her close. She was practically sobbing. I held her to my chest and gently stroked her hair. "What happened?"
She sat up saying, "I tried to think of something good. That part was okay. But when I tried to rub myself I... maybe I was having to focus on too many things... and I started getting wet like you... but then... the feelings just went away. I'm never going to be normal!" she said, putting her head on my shoulder and crying softly.
I lifted up her head to face me. "You are going to be able to feel! We'll figure this out!"
"Thanks, Christy," she said as I wiped a tear from her face. "You're such a good sister!"
"That's what I'm here for," I said, laughing slightly.
We sat silently for a few minutes and I could tell Cindy had something on her mind.