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My First, Her First

"A frustrated brother and sister decide to experiment together, and have an unexpectedly romantic experience."

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It was early spring after my 2nd year of college, and I was moved back home to my parents house. The job I had lined up for the summer didn’t start for another whole month, and the rest of the household still had other responsibilities to attend to: Mom worked and was attending night school to finish her degree, Dad had his career, and my sister Chelsea was still wrapping up her sophomore year of high school. I didn’t have much going on, and so I mostly held down the couch in front of the TV.

I heard the front door open and Chelsea walking in. I looked over my shoulder and could see her shuffling down the hall toward her room to drop off her school bags. A few minutes later she reemerged from her room and was coming my direction back down the hall.

She was dressed comfortably in pink gym shorts, baggy t-shirt, and ankle socks, having changed from the school clothes she arrived home in. She was a pretty girl - sixteen, skinny, petite in every way, with long brown hair and brown eyes. We’d always been close, more like best friends than siblings in a lot of ways. We enjoyed spending time together, and even occasionally called to chat by phone during the months I was away at college.

Chelsea came into the living room and sat on the other half of the sectional couch I was sitting on, and curled up with her feet beside her and nose in her phone. Her legs were slightly pale, and smooth as butter (I knew from the couple of times I had briefly touched them); and thin in a way that only exists on HS girls and fashion models.

We said “hey” but not much more, and I kept watching the afternoon baseball game that was on.

Chelsea spoke up, “God I’m so over listening to everyone’s boy drama.”

“Haha,” I replied. “Is it Hannah and her on-again, off-again, dating saga?”

“No, Kali. She finally got a boyfriend and snuck over to his house last weekend to fuck him. Now it’s like she’s got some stick up her butt because she’s an ‘experienced woman.’ She actually called herself that!”

"Wow, that’s embarrassing,” I said. “Hop on one dick and suddenly too good to talk to your old friends.”

“I know! I guarantee a dicking from that pimply-faced guy from biology did not impart you any special wisdom,” yelled Chelsea, laughing.

We laughed a bit more about how embarrassing it all was to act like her friend Kali was, and I turned back to my game.

Chelsea broke the quiet. “I guess I do get embarrassed a bit also. Most of my friends have all had boyfriends and done stuff now, and it’s stupid to think it makes you any better, but I still get jealous that I haven’t. Like… I just wish I wasn’t the only one not having those experiences.”

“Like going out on dates and stuff?” I asked.

“Well yeah, but more the ‘doing stuff’ part. Like I haven’t even had my first kiss yet,” she answered.

I felt bad hearing that, but it wasn’t a surprise. We’d had similar conversations in the past about our frustrations with dating and feeling like we’re missing out. It wasn’t that either of us was ‘waiting’ or being prudes; but we also weren’t the sort to throw ourselves into silly flings with people we didn’t even like. Our small town made the dating pool pretty tiny, and there was probably a bit of bad luck thrown in for us both as well.

I tried to be supportive as I could, and relate with her: “I’m sorry Chels. And I get that too… trust me it doesn’t get any better being in that same spot as a 21 year old.”

“I know, I’m not trying to complain,” she said.

I answered, “I know that, I know it’s hard. Sometimes I think we should just do it ourselves to fix both our problems!”

I felt a bit awkward when the words came out of my mouth. Not severely because I was obviously joking, and it wasn’t totally beyond how we typically joke. But still, I felt I pushed the line a bit and wished I could take it back.

Things got quiet for a few moments, like new we both just received new information and didn’t have responses prepared. I could see her slowly nodding as she stared at the floor thinking. Wait… was she considering it?

“Nobody would EVER be able to find out,” she finally said, somewhat quietly.

I didn’t know what to say. “I mean… yeah that would definitely have to be our secret.”

Things got quiet again. My mind was racing… could this actually happen? Does Chelsea want this?

Honestly, I was attracted to Chelsea - very attracted. I liked her personality, and everything about her. I had always snuck extra looks at her when I could, and extra touches when I had reasonable excuses. I even jerked almost exclusively to thoughts of her and my favorite pictures of her. Honestly, no girl ever comparing to Chelsea was probably why I failed so terribly at dating - but I never actually thought it would go beyond my imagination in any way.

Chelsea spoke up again, slowly, “Just once so we both know what it’s like… no kissing or anything like romantic and weird”

“Of course, yeah, but…You want to?” I asked.

Chelsea: “Why don’t we try it, just to see?”

Me: “I mean.. yeah, only if you’re okay with it.”

Chelsea: “Do you want to come to my room?”

*************

Chelsea stood up to begin walking to her room. I did the same, and felt such a tingly mess I couldn’t hardly remember how to function. She walked just ahead of me down the hall, neither of us saying anything; and I felt like a robot pretending to be human. Walk normal, breathe, move your arms, no not that much. I didn’t have an erection, but my groin was a staticky fireball. I couldn’t believe this was happening… I was about to make love to Chelsea, my little sister? No, not love, just sex. Whatever exactly that meant.

She turned into her bedroom, and I followed behind her. She waited by the door as I walked past her, and she closed the door behind us, and locked it.

I don’t think either of us knew exactly what to do next - she looked as scared as I felt. I sat on the edge of her unmade bed and looked up at her, still standing close to the door. She stepped closer and asked me, “Do you want to start?

“Y-yes,” I said, and I started to remove my shirt. She stopped me and said, “No, leave our clothes on. Don’t make it weird.”

“Ok… I mean I think we have to at least take our pants off if we’re going to do this.”

“Ok, yes, sorry.”

I unbuttoned my jeans and stood up to pull them down. At the same time, we bent over to lower our pants, leaving our underwear on. Her panties were white with a green band; my crotch had a noticeable bulge that I couldn’t hide, and I was self-conscious she’d think I was a pervert for being turned on by her.

“You first,” she said.

I was anxious about it but didn’t want to break our rhythm. I tucked my thumb into the waist band of my underwear and pulled them to my ankles. I stood back up, naked from the waist down and my cock pointed directly ahead, feeling the most exposed I’ve ever felt.

Without saying anything, Chelsea did the same. She tucked her thumbs into the waist band of her panties, gently pulled them down to her ankles, dropped them, and then stepped out of them completely. Her pussy was smooth and white - only a few wispy hairs grew on her mound, like the hair on a newborn baby. My cocked strained and pushed, and I swear it could’ve shot a load the full distance from me to her if I let it.

She walked toward me, I thought at first to give me a kiss; but then walked right beside me to climb onto the bed, turn around, and lay down on her back. She lay with her legs extended straight out on the bed, but spread apart.

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“I think I’m ready,” she said.

I moved to between her legs, my cock still straining. As I inched closer, she bent her knees and spread them further apart, allowing me room to take position. She was the sexiest girl I had ever seen.

My cock was an inch from her pussy, and I looked at her in the eyes. “Are you sure you want this?” I asked. She nodded “yes,” and bit her lip nervously.

I leaned in and touched the head of my hard cock to the entrance of her pussy. I felt electricity go through me, and I start to very lightly push. She was too tight for me to make it very far, so I let off, and started a slow pattern of leaning my hips forward to press against her pussy, and letting off. Slow-on, back-off, on, off, each time just gently firmer than the last. I set a hand on her abdomen, just above her soft mound. I let my fingers spread and feel her skin, and roam my thumb down to feel the first folds over her vagina, while continuing my slow rhythm - press, back-off, press, back-off. I then let my hand slowly glide up her abdomen, with my fingers just beginning to slide beneath her t-shirt.

Chelsea gently put her hand on my wrist and said calmly, but sweetly as she could, “Don’t make it weird,” and moved my hand off of her.

“I’m sorry,” I said, working hard to accept the small rejection in stride, and also hoping I hadn’t ruined the mood already.

I put my hands back into position on either side of her on the bed, and continue my rhythm. At this point, the very top of my cock head was lightly spreading her pussy, but I hadn’t even begun entering her in any real way - she was very tight. We had hit a wall and weren’t making further progress, and I started to get concerned about this whole experience falling apart - she was too dry, and her pussy was not relaxing to allow me inside - and she also resisted my efforts to touch her and stimulate her body.

“You’re doing so good, Chelsea. You’re doing so good," I said, trying to encourage her with my words.

I heard her let out a deep breath, and she seemed to calm slightly.

I continued, “I’m not even in yet and you already feel so good. I’m so happy we’re doing this.”

I felt a a new slipperiness as I continue my slow, gentle, dance. Press-in, back-off.

“I’ve wanted this for so long, I’ve dreamed of you. You’re so beautiful.”

I felt more wetness, and the head of my cock slips inside of her for the first time, just barely.  She whimpered, and I slid back out. As I began to push again, she put her hand down to my abdomen and said, “Can I get on top?”

“Of course,” I said, and I rolled over next to her, my cock laying on stomach, pointed up my body.

She got up onto her knees, turned to face me, lifted a leg over my waist, and sat gently. Her baggy t-shirt covered all of her body down, just her pussy peeking out below, which was sandwiching my cock against my abdomen, with her lips spread to either side of it like a hot dog bun.

“Will you keep talking to me?”

“Of course, you’re my whole world.”

In the same rhythm I had used to press into her body, she began to slide on me. Press forward, release slowly back. Press forward, slow back. Forward, back.

“Oh my god Chels, that feels so good, you are incredible. Keep going.”

She slowly picked up speed. Farther forward, farther back - she slid harder, with more purpose. After a few more slides I felt her go further forward still, and I could feel the head of my cock positioned at the entrance of her vagina. She held that spot, and slid back ever so slowly, and my cock began to enter her body.

With the head of my cock just inside of her, she lifted her body off of me, so that my cock was pointed straight up toward the ceiling, and inside her. She looked up at me, and we made long eye contact.

“Please Chels, do it. You’re perfect, I want you so badly. You make me feel like I’ve never felt before.”

I lifted each of my hands from the bed and set them onto her bare thighs, feeling their smoothness and warmth. I think I saw the slightest hint of a smile, and she slowly but firmly, lowered herself down my cock. I sunk fully into her, until she bottomed out at the base of my cock, completely enveloping me. I was in heaven. The wetness was there in spades, and the heat; but she was tight.

Chelsea breathed in sharply, and spoke, “I need a second, don’t move. I need to get used to it.”

And we sat there with me deep inside my sister. I could feel from the inside every twitch and movement her body made - her heartbeat, her breathing, little muscle adjustments as she was feeling out this new experience and settling in. My cock would throb, and I’d feel the friction of that little movement against the walls of her vagina, and she would twitch and respond to that throbbing as she felt it also.

Slowly, she started the rhythm, but so small that we weren’t even sliding, it was only pressure forward, pressure back. Forward, back. She got more confident with it, and began to rock more confidently - but I still wasn’t not sliding within her, only pressure.

And then I saw it - she started to shake, and she slowed to a stop. Her shoulders lifted slightly and she started to tense. I moved one hand from her thigh and pressed it palm flat across her stomach and felt it tightening and loosening, vibrating, and shaking. She was having an orgasm.

“Chelsea make love to me. I adore you, I’m in heaven inside of you!”

Her shaking came to an end, and she looked back down in my eyes. She pressed her legs back and locked them around mine, and ground her pussy into my abdomen with my cock still buried inside her. She started to rock, and then slide, harder and harder. She was fucking me truly now, in every sense of the word. Using her kegs locked around mine for leverage, she bucked and rocked and pounded.

I grabbed her ass as she rode, and let one hand glide under her shirt and up her back. I reached her bra clasp and pinched it - it popped open and fell to her sides in what must’ve been pure luck. I moved that hand from her back to stomach, felt along under her shirt, under where her bra was not just hanging, and felt my hand to the center of her chest with her small tits hanging on each side.

And just then she yelled, “I’m going to cum!” and lay her body down onto mine - chest to chest. No room for my hand, I took it out of her shirt and grabbed again to her ass with both hands and fucked her with everything I had.

Suddenly, she moved her head and locked her lips onto mine. She moaned into my mouth, put her tongue down my throat. Her breaths got choppy and inconsistent. Our tongues were dancing and reaching inside one another, getting as much as we possibly could.

Her whole body against me, her orgasm squeezing my cock inside her, her moans and tongue locked into my mouth, it was too much. I exploded inside of her with blast after blast. I stopped pumping and only tried to push as deep into her body as I possibly could. I tried to bury my cock deeper inside her m than it was humanly possible to go, and I still wanted more. I kept pushing and release more sperm inside of my sister the perfect girl. I kissed her deep and sucked her tongue and held her ass like it was the last moment of our lives.

And we stayed like that. Our orgasms finished, she stayed collapsed on me, we didn’t move. Our mouths even stayed locked together, tongues inside each other’s mouths but only barely moving, enjoying the last tastes of passion. I made a couple last presses in and out of her, appreciating Chelsea for all she is, and not knowing if I’d ever have the chance again.

Chelsea put her hands on either side of me and lifted her chest away from mine, and looked me in the eye again. The neck of her t-shirt hung low, and without straining I could see down her shirt and her tits hanging there, beautifully. She smiled and pushed herself the rest of her way up, and then got off of me. My cock fell out of her pussy, and behind it my cum, hers, and some blood - it must’ve been from her hymen. And to it her saliva on my lips, her sweat on my skin, and the smell of her hair all around me - it was intoxicating to be drowning in her.

She got off of the bed and stepped up beside me. I could see her pussy, bright red, puffy, and wet; and a long drip of my cum running from her pussy, down her leg almost to the knee. She bent over me and gave me a slow kiss on the lips, and said “Thank you,” before standing back up, and walking to the bathroom to shower. I knew that our parents would be home soon, so I got out of her bed, and went back to my own room to do the same.

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