My sister Cristi and I weren't always friends, but, being similar ages and personalities, we always knew we could rely on each other for advice and support. The summer after I graduated high school, when she got home from her freshman year of college, was when things changed for us.
We had a swimming pool in our basement–-yes, in the basement, not the yard–-and this gave us great opportunities to relax, even at night when outside there wouldn't be enough light. The previous summer I had spent a lot of time ogling Cristi's tightly-suited body when we both got bored late at night and felt like getting some activity that wasn't too strenuous. Back then we'd gotten into the habit of talking with each other (mostly her giving me advice about classes to take and teachers to avoid at the high school). This was a tradition I hoped to revive from the first night we were both home, not least because of the ogling, but also because she was excellent company.
I was gently gliding from one end of the pool to the other at about midnight when Cristi stepped into the pool room. Her body hadn't changed at college, at least as far as I could tell, but having been at home for a week with no high school hallway eye candy, she looked even better than it would have otherwise.
Her blue one-piece, rather than giving every little detail away about her figure, made my imagination work a little to see the wonderful curvature of her abs, and deemphasized her breasts. I knew them to be a C-cup from years of snooping in the laundry room, but her suit gripped them tightly enough that they wouldn't wobble, with the side benefit that I could distinguish her nipples.
What little brotherly propriety I had left in me made my eyes drift over her mound quickly, getting right to her smooth, shapely legs. Cristi usually runs for exercise, giving her basically perfect legs. I'm not sure, but I may have forgotten to breathe for a few moments.
"Something wrong, Jon?"
I hadn't noticed that my eyes were taking her in a little too intently, so I had to recover and try not to blush too much. "Well, Cristi..."
"Checking for tattoos?"
"As a brother, I have to make sure that your no-good boyfriend isn't hitting you. It's a protectiveness thing." I thought she didn't buy it when she sliced into the water, but then she popped up right next to me, embracing me, much to my surprise.
"Thanks, Jon. That's sweet, whether or not it's completely accurate." She pulled back and smiled at me. "But I don't even have a boyfriend right now. So you have nothing to worry about."
"No boyfriend? For how long?"
"I went on a few dates this semester but the only guy that lasted more than a week was first semester." She didn't look upset by this at all, so I didn't see any reason not to ask for more information.
"Now Cristi, I don't mean to pry, but..."
"No, I didn't sleep with him." I was relieved I didn't have to finish the question. "I'm still a virgin, Jon." After a moment in which I didn't know what to say (hey, *you* try to say something there that doesn't offend or trivialize her), she broke the silence again to ask, "How about you? Have you had sex yet?"
My male instincts screamed at me to bluster and inflate my experience, but we made eye contact and I humbly sighed, saying, "No, I haven't. The closest was a handjob nine months ago." I blushed at this admission.
Cristi, a little embarrassed to see me so vulnerable, brushed a strand of her wet hair behind her ear as she floated closer to me in the pool and said, "A few guys have groped me a little through my clothes. The most intense it's ever been was when I had my hand over a guy's fully-clothed crotch and he...um, I guess "came" early."
I don't know what came over me, but suddenly I got a shot of courage and said something I wouldn't have in a million years expected to say to my sister.
"We should do something," I said.
"What do you mean?"
"Well, I've never gotten farther than handjobs, and you've never gotten further than heavy petting. Why shouldn't we? I can't think of a nicer way to learn about sex than with someone I trust, like you. We're both mature and attractive people, and from what I've heard, it's pretty fun."
She was quiet for a minute, as if she didn't know what to say. Finally, "You're attracted to me?" Her facial expression was not encouraging, but it was still more surprised than revolted so I quickly worked to recover.
"Definitely. How could I not be? You take good care of yourself. You're thin, curvy, and soft-featured--how much more could I ask for?" She looked at me like she still didn't know how to respond to the idea. "How else would we lose our virginity? To some transient post-adolescent relationship? I don't anticipate falling into real love for a long time. I think it would be a great way to become closer between us. It would be a way to express our friendship in something beautiful. I don't wanna pressure you, but I don't want you to dismiss the notion out-of-hand. And if you don't want to, I'm not offended, so don't take my feelings as significant. It's your feelings that matter."
She said, hesitantly, "I don't know, Jon. Don't think I'm not flattered or that you're not attractive, but I had never really thought of this before, and you obviously have. I'm sort of dealing with the idea a little more." She paused, pursing her lips in just the thoughtful way I found so appealing. She crossed her arms over her breasts as if to hug herself. "Just leaping into your bed seems like the wrong decision, but I am curious, and I do trust you and value our relationship." Another pause, shorter this time. "I think that it could work just fine if we took it slow." She smiled at me and I smiled back awkwardly, internally calming down from the coronary events of the past few minutes.
"So, where do we start?" Cristi asked.
"The better question is, how far we want to go this first time."
She pondered it, and came upon a solution. "Let's not touch tonight. We should watch each other."
I nodded approval eagerly, and we climbed out of the pool. After a few awkward moments not knowing how to strip in front of an imminent lover, we each ended up completely naked.
Cristi was one of the lucky women who was just as beautiful with her clothes off as on. Her naked body was sculpted into just the right curves. Her breasts weren't huge, and they weren't small, but they were neither saggy nor hard; they had that exquisite balance of the two. Her legs weren't *as* perfect as those tits, but the silky skin was so smooth that my eyes could hardly believe themselves. By the time I was done with my first visual examination, my mouth was watering and I couldn't hide my seven inches of satisfaction from her if I'd wanted too.
I looked back at her face, and after a few seconds, her gaze drifted from my cock to my eyes.
"You're beautiful." I told her.
Silently knowing that the other wanted to proceed, we both sat down, in the his and hers deck chairs that sat at the poolside. We were looking straight at each other from hardly ten feet apart. A lot of nonverbal communication was going on, as if we were each beaming signals to each other that both of us were afraid. I moved my hand around my shaft, never taking my eyes off of her as she moved her hand down to stimulate herself, inserting first one finger, then another.
As I started moving my hand up and down, she started to move her fingers faster and faster, letting out a moan and briefly closing her eyes as if to let herself catch up with all the stimulation before accepting more. The hottest part about it was how she kept staring at my cock, like she wanted it more than anything.
Eventually she devoted her thumb to rubbing her clit, which I took to mean she was nearing her orgasm. It was a good thing, too, because I probably couldn't hold back much longer, and I wanted her to cum first.
"Cum on me, Jon, please!"
That was it. I could hardly get over there fast enough, no matter how short a distance it was. There was no holding back once a woman that hot and ready gave the command. No sooner was I in position than I started to release, and, not knowing where she wanted it, satisfied my fantasies by sending the whole load onto her tits. It was probably the greatest orgasm I'd had to date, and it set her off into her own writhing ecstasy.
Afterwards, we went upstairs and lay together naked on my bed with my arm around her while we talked about it. When she finally decided to go to bed, her parting words as she finished pulling her pajama shirt over her head were, "More tomorrow?"
The next night, we were talking again about school and our lives, and it was finally late enough that our parents would be asleep. At a pause in the conversation, Cristi said, "Should we touch tonight?"
"It's up to you," I said.
She thought about it and decided, "I'm not ready for oral sex, but I would like to give you a handjob and let you do the same for me. I think that'll be tonight's fun." No sooner had she finished than both of us started stripping. I was still amazed that she was so hot naked, and she seemed proud of her ability to turn me on just from her looks. There was a moment where we weren't sure who should go first, but then I motioned for her to sit down, and got my hand in position.
Kneeling between her spread-eagled thighs, I inserted two fingers and put my thumb where I thought her clit was, but she giggled at my error and clued me in to the right spot. I tried to be gentle and soothing, eventually getting her extremely wet, and she almost purred a few times. When I started really moving, her breathing got faster. Remembering something I read online, I turned my index finger to make a beckoning motion inside her until she arched her back in a climactic orgasm.
Quietly removing my hand, she thanked me in a whisper and, after taking a few moments to recuperate, directed me to sit in front of her. I did, my manhood rigid before her. She gently reached her all-too-smooth hand around it, grasping it experimentally, and then started to jack me off. I improved her grip a little, and before long I was moaning. Seeing my younger sister's hand slide up and down my shaft, her tits shifting as she jacked me off, was incredible. Soon, I knew I was going to cum, and relayed the information. Cristi just increased speed.
My jizz fountained up, making a true mess all over her hand as I felt on top of the world. When I finally stopped spewing, she removed her hand, licked it clean, then wiped more of my juices off of my shrinking cock and licked those up, too.
"Ooh, tasty! Thanks, Jon." She got up and started to get dressed while I sat there watching her increasingly less-naked form bend over, twist, and generally ooze sensuality into the room. When she was fully dressed, I was hard again. She turned around and saw my state, grinning widely. "Did I do that?"
"Ohhh, yes. Cristi, you're the hottest woman I've ever seen. I'd be worried if you dressing in front of me didn't send me rampant."
"That's so sweet. You just hold that thought for tomorrow night, though." She went to the door, and before she opened it, turned around and said, "But don't jack off. That cum is all mine, and if you waste it, then how can we have fun?" She left with a smile on her face and an erection on her brother. I thought about jacking off, but decided to follow her mandate. Who knew what she might have in mind for our next fun?
Twenty-four hours later, I was sitting in my room waiting for Cristi to show up. it was about midnight, and I was a little worried why she wasn't here. Was she having second thoughts? Would I never see her beautiful form in the nude again? I sat around for another half an hour before she walked in, silently closing the door after her.
Bracing myself, I awaited her words as she paused. After about ten seconds, she flung her hair over her shoulder sensuously and began to speak. "Jon, I've been thinking, and I don't know if this is right. I know what you said earlier, but now that we're kinda into it, I'm a little uncomfortable."
"Cristi, what can I do to make you feel like this relationship is just the same as one with any other guy?"
"Well, I think it would be better if we did things in my room, for starters. I also want you to call me Cris. Only mom and you call me Cristi, so it kinda reemphasizes our connection." I raised my eyebrows, wondering if that was really all she wanted, those miniscule issues. "I also want us to not go all the way. I've managed not to lose it so far to anyone, and I think I want to save myself for marriage." I let go of the breath I'd been holding. So she didn't want to call it all off. We could continue, but I wasn't getting snatch. I could handle that.
"No problem, all those things are fine, Cris. Why don't we go off to your room and have some fun?" She smiled and nodded, and we shuffled along the hallway to her room.
Once we were there, we quickly and un-self-consciously stripped our clothes. Her stunning body was once again before me, and I was well on my way to maximum stiffness by the time she was done. "Sit down, Jon." I did so, sitting in the middle of her bed and looking forward to whatever she had planned. She kneeled in front of me, wrapping her hand around my shaft, then moving it up and down. I was entranced by the bouncing her bare tits were doing, and the incredibly silky skin of her thighs. I didn't even notice her head was moving until she released a hot breath on my cock. Our eyes met, and I got the stupidest grin on my face, like a man who'd just struck gold. She moved her mouth over my twitching cock without touching, removing her hand to hold my side. Then, in a moment, she had enveloped me in her mouth, setting off just about every pleasure center in my body. As she bobbed her head up an down on my shaft, I was lucky to even remain conscious from all the pleasure. And this was only her first time! I thought I was going to explode, when she suddenly pulled off.
I was sitting there catching my breath, when she rotated me to lay on the bed. I was a little confused, since she had just told me she wouldn't go all the way, but as my hormone-dazzled brain eventually figured out, there was more than one way to penetrate a woman. Cris lowered herself onto me, grinning at my pleasantly surprised expression, and suddenly my wet and rigid cock was at the entrance to her asshole. It was like a tight dream, fully encompassing me. After the initial resistance, it only took a few more moments before I bottomed out in her ass. I decided that whatever feeling she was getting in exchange for the tight fit wasn't enough, so I used my right hand on her steamy wet slit. That definitely got her moving, because only a few seconds later, she was having an orgasm, clenching her ass muscles in a way I couldn't resist. I pulled her all the way down, grunted, and sprayed my sister's interior with jet after jet of semen.