Ch 03 Craig First Time With Cindy

I was done with sex. My first time had been awful. I'd just turned 18 and was at a party. I'd had too much to drink. Steven had too. We hooked up, but neither one of us knew what we were doing. It was painful for me and not pleasant, at all.

I say "was done" because, about a year later, my older sister, Christy, came to my rescue. Christy is two years older than me. I'm 20, and she's 22. We're practically twins, about 5'7" or so, with olive skin, dark hair and breasts on the smaller side with large, dark areola, and nipples that like to harden when we're turned on. The only real difference is that Christy has a dark bush, where I wax my pussy. Christy's hair is dark like mine, but longer.

Last summer, when she got home from college, Christy shared with me her sexual experiences with her best friend Melissa. It sparked an interest in me and, with Christy's help, I discovered the incredible highs of sexual intimacy. Yes, it was with my sister, but my love and trust for her overcame any social taboos.

We spent much of the summer discovering the wonders of lesbian sisterly love. That fall, we ended up at the same college and rented an apartment together. Melissa would come over to visit sometimes, and even bring her older sister Karen. Those were fun times, with lots of kissing and licking and cumming!

I was over my fear of sex, but I wondered if I was over my fear of sex with men.

How I overcame my fear started innocently enough. Well, maybe not totally innocent. Craig's friend Mitch was coming over to our family home to spend the night. My folks were going away for the weekend and asked Christy and I to come back and be in charge. Christy and I both liked Mitch. He and Craig are both 18 and, at 6' or so, brown wavy hair, muscular build with a narrow waist, Mitch was very handsome. He was also a virgin, which I learned from overhearing a conversation between him and Craig.

We were pretty sure he had a crush on both of us. I was just beginning to wonder what it might be like to let a man's cock get back inside my pussy, but wasn't ready yet. Christy wanted to fuck him in the worst way.

She had this naughty idea for us to do a modified strip tease for the boys. We wouldn't get totally nude, but down to our underwear. Yes, it was flirting, and yes, I was pretty excited thinking about it.

As the boys did the dinner dishes, Christy and I changed into extremely short skirts, black tights over black panties, and clingy tops that outlined every curve in our boobs quite nicely.

We told them to sit on the couch. I put on some soft jazz music and we entered the room. We'd choreographed a pretty sensual routine, hips gyrating to the music, hands working in unison while we tossed our heads to the side and gave the boys a very seductive look. Then, the undressing part began. We kicked off our shoes, and turned our backs to them, lifting our butts in the air as we removed our tights.

I noticed Mitch getting pretty uncomfortable, moving around to adjust himself. I could see pretty plainly that he had a hard on. What surprised me was that Craig had one too. I could see his dick swelling in his shorts as we turned and began stripping off our tops to reveal skimpy matching bras. Finally, we shimmied out of our skirts, leaving us only in black underwear.

We grabbed our things and hurried out as Mitch called after, "You didn't have to stop!"

We laughed as we got back to our room and put our regular clothes back on.

"What'd you think?" Christy asked as we sat back down on the couch.

"Did we do good?" I asked.

"What was that about?" Mitch asked, trying to hide his erection.

Craig actually had to shift his cock around to find a comfortable position. I found myself drawn to it, and tried not to stare. Truth is, I'd never been attracted to my brother before. But realizing the power we had over him, our ability to really turn him on, was intoxicating.

"Did you see their cocks?" I said after we were back in our rooms for the night.

"They were both pretty turned on," Christy said. "And so am I!"

Later that night Christy, made her move on Mitch. She waited for him to get up and use the bathroom. She then got up and waited for him in the hallway.

She later told me she kissed him and grazed his cock as she went by. The next day she invited him over to our apartment to work on her computer. I knew that she was going to have sex with him, and I began thinking about sex, and about Craig. I wondered if doing it with someone safe, like I did with Christy, might be just what I needed.

We left home together, but I came back to give Christy some privacy. It was just Craig and I for the next 24 hours.

He was playing video games when I came in. He was dressed in running shorts and a t-shirt. He's pretty muscular and as tall as Mitch. Some might say he qualifies as tall, dark and handsome. I put my bags back in my room and joined him on the couch. When I sat down, he paused the game.

"So what was that really about last night," he asked.

"Oh, the strip tease?" I said.

"Yeah the strip tease!" he said, wagging the game controller at me.

"Well, honestly," I said. "We were trying to turn you guys on."

Craig shook his head. "Well, it worked!"

"I could tell," I said slyly, glancing down at his crotch.

Craig must have been remembering the night before, because I noticed a slight movement under his shorts.

"Mitch I understand," Craig said, shifting a little. "But I'm your brother!"

"I know!" I said, smiling. "We were just being silly. It didn't mean anything."

Craig paused, looking at me strangely. "Well, it wasn't silly to me."

"I'm sorry," I said, regretting what I'd done.

"Don't be," he said. "You actually did turn me on big time. I couldn't believe it, but when I went to bed, all I could think about was you taking off your clothes and seeing your nipples poking through that thin bra."

"Oh!" I said, surprised.

"I hate to admit this, but I jerked off thinking about you, my sister!"

"Wow!" I said.

"And it was fucking amazing!" he said, setting the controller down. "I'm not supposed to think about having sex with my sister but I can't seem to stop!"

He seemed almost mad at himself.

"You must think I'm some kind of a perv," he said, looking down.

"Not at all," I said, putting my hand on his thigh, his very muscular thigh.

I began very gently running my fingers through the hairs on his leg. Craig stared at my hand. I noticed the front of his running shorts beginning to bulge.

"Shit!" he said. "It's happening again!"

"It's okay. I kind of like it, actually," I said, moving just slightly towards his growing cock.

"You like it? Does it turn you on looking me getting a hard on?"

I nodded, looking up into his eyes. "I'm totally wet right now thinking about your cock."

Craig looked surprised at first, but didn't move my hand away as it inched closer to a now very obvious erection.

"Shit!" he said again.

"Is that the only word you know?" I said.

"No, but it's the only one I can think of with your hand almost touching me."

"Do you want me to touch you, Craig?" I asked, looking down at his crotch.

"I do. Is that wrong?"

"Not to me it isn't," I said, moving my fingers to just graze the head of his cock, which was laying on its side and nearly pushing out of his shorts.

His cock jumped in response to my touch and grew even bigger.

"Oh fuck!" he said.

"You okay?" I asked.

"Shit yeah!" he said, shifting so the head of his dick actually did peak out from under the fabric.

I became bolder and put my hand on top of his cock and squeezed slightly. Craig moaned in response.

"More?" I asked, not wanting to take this too far for him, or me.

"Oh please!" he said, pulling down his shorts and underwear in one motion.

His very large dick sprang out, standing straight up in the air, fully erect and throbbing.

I caught my breath. It was beautiful. And I wasn't repulsed like I thought I'd be after my first bad experience with sex. Instead, I reached out and grasped his shaft in my hand, stroking up and down softly.

"You have a beautiful cock, Craig. It's so big!"

"I guess," he said. "No one's ever seen it like this before, or touched it."

"You mean?" I said, still staring at his member.

"I'm a virgin," said, in an almost defeated tone.

I looked up, removed my hand from his dick and cupped his face in my hand. "I'm glad you're a virgin, Craig."

"You are?" he asked. "Why?"

"Well," I answered, "this is going to sound really strange, but I've only been with one guy before, and it was bad. I've been thinking lately about maybe giving guys another chance, but wanted it to be with someone I know well and trust."

"You mean?" he said, looking into my eyes with an almost pleading expression on his face.

"I mean, I would be honored if you'd let me be your first."

Craig reached over and put his hand on my shoulder. "I can't believe I'm saying this, but I would love to fuck you, even though you're my sister!"

With that, he pulled me close and planted a gentle kiss on my lips. I pulled back and then went in for a much deeper one, sending my tongue into his mouth. While we French kissed, I put my hand back on his cock and began stroking it again.

After we broke off, Craig kicked his shorts the rest of the way off and onto the floor. I took his hand and put it on one of my boobs. He started kneading it gently.

"My nipples are hard," I said. "Can you tell?"

"Uh huh," Craig said, running his fingers across my tits.

"Do you want to touch them?" I said, reaching down and pulling off my t-shirt. I wasn't wearing a bra.

"They're incredible!" Craig said.

He reached over and began touching both nipples.

"Ummm. That feels good!" I said. "Squeeze them, oh, like that, yeah. Now put your mouth on them and suck my tits!"

Craig leaned in and took a breast into his mouth. It felt so warm to have his tongue licking my nipple. I could tell I was getting really wet and really turned on.

I kissed him again, and moved down to take his cock in my mouth. First I just grazed my tongue on the head of his dick. He took in a quick breath as my mouth went over and down his shaft.

"Oh fuck!" he said. "You're sucking my cock. You're sucking my cock!"

I went down as far as I could, sucked in and pulled back up. I could tell even that little amount was going to bring him close to cumming, and I didn't want that yet.

I came off his dick and pulled off my shorts.

Craig stared at my bald pussy.

"I've never seen one in person before," he said.

"Touch it," I said, guiding his hand between my legs.

His fingers pushed aside my sopping pussy lips and traveled down my slit, sending shivers up and down me.

"It's so wet!" he said.

"It wants your cock!" I said. "Now put a finger inside me - here," I said, guiding his hand to my pussy hole.

"So warm inside," he said, his finger disappearing inside me, sending delicious feelings all over me.

"This is where your cock is going to go," I said, pulling his fingers out.

"I want you to fuck me now, Craig. Put your cock into my pussy and fuck me!"

I laid down on the couch and helped him move between my legs, grabbing his cock and pulling it near my pussy. I was about to let a man fuck me again. This time, though, I wasn't drunk, and totally wet and turned on.

"I'm going to help you inside me, Craig," I said, positioning his dick at my entrance. "When I say so, you can push and you won't be a virgin anymore."

"Okay!" he said, staring at his dick about to enter his sister's pussy.

"Now, Craig," I said. "Push gently."

I watched and felt him enter me, pushing apart my lips and sliding easily into my pussy. It felt so good. His cock was so hard and big. It really stretched me out, but that only served to increase the pleasure. Craig held himself up by his arms so he could see his cock fuck his sister.

"That's great, Craig. You did it. You're not a virgin anymore!" I said, wanting to fuck that cock so bad.

"Now, you'll have the urge to push, and that's okay. I want you to do what comes natural."

He began to pull out and push in, slowly at first, then more quickly. I felt my breathing quicken and my hips rose up to meet his strokes.

"I know you, oh, ah, probably won't last long, but I want you to cum when you're ready. Shit! Yeah! Oh! Don't hold back."

"Inside you?" he said urgently.

"Yes, inside me. You can cum inside me, nothing will happen. I'm on the pill. Oh fuck, my brother has his fucking cock inside me. I think I'm going to cum. Shit!"

My head went back and I came. Just then Craig's cock spasmed and I could tell he was cumming too.

"Shit!" he said, and I felt waves of pleasure and waves of Craig's cock pumping his jizz into me.

I hadn't expected to cum so quickly, but the feeling of my brother's shaft moving in and out of me was just too much.

Craig, finally spent, laid on top of me.

"Oh shit! I fucked my sister!" he said, raising up again on his arms.

"Fuck yeah! And it was great!" I said, bringing him in for a kiss.

Once his dick began to soften, he pulled out and watched semen drip from the end of his cock onto my stomach.

I grabbed the dribble with my index finger and put it my mouth. It tasted salty but delicious.

We lay next to each other for a while, just enjoying the after glow of a brother and sister who'd become lovers.

"Did we just fucking do that?" he said, running his fingers through my hair.

"We did. Still feel okay about it?"

"How could I not?" he said. "You're amazing. So beautiful and so sexy. I'm blown away. You don't feel weird about fucking your sibling?"

It was time for a confession.

"No, I don't. In fact, there's something I need to tell you. Last year, Christy and I, well, we became more than sisters."

"More than sisters?" Craig said. "You guys..."

"We did, Craig. We became lovers too and it's been amazing!"

"Shit!" Craig said. "So hot! My two sisters fucking each other. Can this day get any better?"

I laughed. "Well, it can actually. You came fast the first time, but I bet with a little coaxing, we can get your dick hard again and you can fuck my pussy a second time."

"I'm in!" he said.

"Oooh, good!" I said, getting up and grabbing Craig's hands. "Let's shower first!"

I led him down the hall and into our parent's room. They have a huge stone shower with a rainfall shower head. I turned on the water and pulled Craig in.

We kissed, our tongues meeting and touching and then diving into our mouths. I lathered up his chest and legs and then paid special attention to his cock. Once I got it nice and clean, I started sucking him as the warm water splashed over us. His dick got hard very fast, but I wasn't done yet!

"Your turn," I said, handing him the soap.

He got me all lathered up, and I encouraged his hand to start exploring my body. He roamed over my stomach and mound and into my pussy. He bent down and kissed my butt cheeks and started licking my pussy from behind.

"Oh yeah, Craig. Lick me. Lick me. Oh shit that feels good!"

I turned off the water and we sensually dried each other off, stopping to kiss and fondle.

We climbed onto our parent's bed and lay facing each other. It felt naughty, but no where near as naughty as what we'd already done with each other.

"I want to take it more slowly," I said as I took his dick in my hand and began to stroke it. "You'll be able to last longer this time when you're inside me."

"I love your hand on my dick," Craig said. "I've never felt anything like this before. Jerking off is nothing compared to this!"

"I totally agree," I said, using two hands now to squeeze Craig's cock as I moved up and down his shaft. "Christy showed me that too."

"So, how'd that happen?" Craig asked, reaching out and caressing my nipples.

"When she came home last summer, I noticed that she'd changed somehow. When I pressed her, she admitted to sleeping with Melissa."

"Melissa - her best friend?" Craig said.

"Yep," I said. "She helped me figure out how to feel pleasure again. One thing led to another and, well, let's say we've made love a lot!"

"The thought of you and Christy together is really turning me on!" Craig said.

"Me too!"

We kissed and our tongues moved around in each other's mouths. I broke off and kissed down Craig's chest, finally planting my lips on the end of his dick. This time, I swirled my tongue over the length of his shaft, kissing, and licking it. When I put it in my mouth, Craig lifted up his pelvis.

"Oh fucking shit that's good! I can't believe my own sister is giving me a blow job!"

After his cock was nice and hard, I moved back up to kiss him. "Now it's your turn," I said, guiding his hands to my nipples. "Spend some time getting to know my tits. They're very sensitive."

Craig began licking and sucking on my nipples, making them very hard. He sucked in and pulled back on one nipple, sending a wave of pleasure through me. I lifted my chest in response.

"Keep going, Craig. Shit, that feels good! Now, use your fingers to touch my pussy. I'll show you where."

I laid on my back and guided one of his hands between my legs. I could tell I was already wet. As soon as his finger touched my slit, I began raising and lowering my pelvis.

"That's right. Go up and down like that. Oh yeah. Oh, oh. Fuck. Now, press in a little at the top to find my clit. It's a little knob - oh yeah, that's it. That's it. Now move your finger across it quickly but very lightly."

"Like this?" Craig asked.

"Fuck. Umpf. Oh, oh, oh. Yeah. Just like... that," I said, my hips moving more quickly up and down.

Craig continued to rub my clit, stopping occasionally to get more juice from my slit. I was feeling incredible.

"Now put two fingers in me and use your palm to press on my clit," I said, guiding him into the right position.

He moved his fingers inside my pussy and my breathing got ragged. My head went back and I closed my eyes.

"You're going to make me cum, Craig. I'm close. Shit! Oh! Don't stop! Oh! Yeah! Here I cum!"

I cried out, and my hips bucked up and down as pleasure surrounded me and carried me away. My brother had just finger fucked me to an orgasm!

As I came down from the high, I kissed Craig deeply. "I wasn't expecting that!" I said. "You did great!"

"I loved watching you cum, Cindy," he said.

"Mmmm," I said. "Now I want to fuck that cock of yours. I want to watch you cum too!"

"I thought you'd never ask!" Craig said.

"This time, I want to be on top," I said, pushing Craig on his back and straddling him.

I used some juices from my slit to lube his cock and positioned it right at my opening. I lowered myself onto his dick, which fit in me easily, despite its size. Craig's eyes widened as I mounted him.

"I can't believe the feeling of my sister's cunt surrounding my dick," Craig said as I fit the last inch deep in my pussy. "So warm and slippery. It presses in all around me."

"I can't believe it either," I said, starting to rock my pelvis on his cock. "I never thought I'd fuck another man, but you've changed that!"

I began to move up and down on Craig's dick. I could see it emerge from my pussy, all shiny from my abundant juice, then plunge back inside, sending incredible feelings through me as my clit came down on Craig's pelvis.

"What do you think about your cock in your sister's pussy?" I said, rocking and moving faster and harder.

Craig was staring at my pussy as I fucked him.

"It's fucking amazing. Your pussy feels so tight and my cock feels tingly all over when you come down on me."

Craig started thrusting upward as I pushed down. Our rhythm moved faster, along with our breathing. Craig reached up and felt my nipples. I leaned over and he took a tit in his mouth, sucking it in and licking it.