To Miss, with love: my life with your sister [m/f][m/f]

Dear Miss (you know who you are, I’ve always called you Miss since we met),

I hope none of this is a surprise to you. I hope this is something you know, and don’t mind, and maybe even enjoy, because the last thing I want is to upset you. That’s why I’m posting this online instead of just sending it to you or telling you to your face; you’ve always been a bit of an exhibitionist. That’s part of why you like me, I think- you like knowing someone is thinking about you, fantasizing about you, wanting you more than anything else in the world. And I do want you more than anything else in the world. It’s your face, your body, I see right before I climax, almost every time. After reading this, a lot of other men all over the world will be thinking of you, touching themselves and dreaming of a girl they’ve never seen. I hope you enjoy that. I hope you still enjoy me. I will always enjoy you, and I will always love you.

But I fucked your sister. Not just once. A lot of times.

When we met, you were a mature looking thirteen and I was a young looking fifteen. I didn’t know you had a sister at the time, and if I did, I wouldn’t have cared. I just realized almost immediately that the petite, blonde actress playing Cinderella in the junior high musical was cute. Not cute, beautiful. The kind of beautiful that would blossom into hot in a year or two. I talked to you a little then- you knew me from the high school musical, where I was playing a walk-on role in “Little Shop of Horrors.” I would never have admitted it, but I had a crush on you- preteen and teen “interaction” was very strictly forbidden. Nonetheless, you knew, and you liked my attention, I could tell. And I felt more than flattered about you even giving me the time of day.

A few years later, you were fifteen, I was seventeen and we were both high schoolers. You had blossomed, alright. Small and slim, you had the mermaid look- long, wavy blonde hair that sometimes went brown or got dyed a vivid, wine red; shapely legs and thighs with a fantastic ass; and small but perky breasts that always seemed to be straining against whatever t-shirt or tank top you were wearing that day. I remember once, during choir practice, I sat with my back to the wall, leaning against the mirrored rehearsal space and the radiator in the room, and you sat cross-legged on the floor in a pink tank top faded almost to white, and you whispered in my ear, “Look how long my hair is getting…” I complimented you on it, and you laughed, saying “Soon, if I was topless, all I’d need to wear was my hair. Picture that!” I told you I would- I PROMISED you I would, in fact- and that night I lay in bed under the slow rotation of my ceiling fan, dreaming of you stepping out of the pool, wearing nothing but a pair of translucent bikini briefs, your hardened nipples peeking from behind your dripping hair.

It was around that time that you got your first longterm boyfriend, and stopped flirting quite so brazenly with me. It was also around this time that I met Kelly. A few inches taller and a year and a half older than you, Kelly was a pretty girl but didn’t have quite your air of glamour and seduction. She wore her hair long and iron straight, and dressed in baggier, more nondescript clothes. If you were a girl born to be in the city, Kelly was the sort of girl who stays behind in the country.

Kelly and I never got to be incredibly close friends. I’ll never know her mind and heart the way I know yours, because Kelly’s not really the type to share. But sometimes, I would go to see one of your shows and Kelly would be there. I’d sit with her, we’d chat a little, make some stupid jokes or talk about what we were watching on TV lately. Kelly worked in a coffeehouse in your town, about fifteen miles from mine. She smoked pot, a lot. I had never met a girl who drank or smoked the way Kelly did. I didn’t do much of either, but something about her casual attitude towards drugs and sex and everything else in life impressed me. I never talked to Kelly about you, and I never talked to you about Kelly. Our lives were separate.

Then, when Kelly and I were seniors (at different high schools), both eighteen, something happened that diverged my friendship from her from yours, or maybe brought them closer together. Sitting out behind the cafe, playing music from an acoustic AM radio station through the windows of my car while Kelly smoked cigarette after cigarette, she nonchalantly asked me, “You wanna make out?” After a moment or two of hesitation, I said sure, and we got in my car and drove to a more secluded location behind a Wal-Mart so old it hadn’t become a Super one yet.

We got in the backseat and she climbed in my lap. Immediately I knew that I liked the way she kissed- there was a subtle line of passion through it, but overall it was so cool, so casual. A lazy sort of eroticism. After a minute or two of kissing and some mild groping, she took off her loose black vest and pulled off her long sleeve t-shirt. She wore the kind of black, slightly shiny but nondescript bra girls wear so often when they don’t think they’re going to be showing anyone their underwear that day, but it wasn’t the bra that caught my attention.

Her breasts, small but perky even in the generic bra, were familiar to me- they looked almost exactly the same as the ones I’d fantasized about so often on you. In fact, looking at her now stripped down to a bra and a tight pair of jeans, I realized that, despite having different hair, a slightly different face, and an inch or two of height on you, she and you could have been dead ringers for each other.

“Fuck,” I whispered, and Kelly laughed in the strangest way- half happy, half resigned. “Yeah,” she said, “I know you like that- I’ve seen you staring at it enough on CC.” I blushed. I didn’t think she’d noticed, and I tried to sputter out an explanation, but she kissed me again. “It’s cool, dude,” she said when our lips parted. “Everybody wants to fuck CC, but CC doesn’t do anything with anyone.”

Her hand drifted down to my cock, which was already straining against my jeans almost visibly. “Like, I know she doesn’t do this. Not with you, anyway.” Kelly kept rubbing and stroking me, and I kissed her lips, her neck, her shoulders, the top of her cleavage. I reached for her bra, and was two clasps towards undoing it when she stopped me. “Not today, man. Gotta leave you something to be curious about.” It was strange modesty from a girl who was wrapping her fingers around the outline of my penis through jeans, stroking it like a favorite pet. Her long, straight hair bounced around her shoulders as she teased me.

“What if I made you cum like this?” she laughed. “Like, i don’t take you out, I just make you cum in your pants and you have to drive home that way?” I was close by then, and I told her “I don’t even care. Fuck, you’re good at this.” She smiled slyly. “I’ve had a little practice, you know. But here. Show me what you’ve got and I’ll let you off easy.” She unzipped my pants and deftly fished my cock through the opening in my boxers, not an easy feat considering how erect I was at the moment. “Not bad,” she told me. “I could get used to this.” She pulled my shirt off with one hand, still stroking my increasingly wet erection, and guided me sideways onto my back, so I was stretched across the backseat. Then, increasing the pressure and speed of her hand, she leaned forward and kissed me, biting my lower lip as she squeezed slightly, then harder, at the base of my cock.

I came, but I came thinking of you. Kelly and I cleaned me up, as I wiped my chest off with a slightly used Kleenex and Kelly shoved it into an empty Gatorade bottle, which she tossed out the window into a ditch. We got dressed and drove back to the cafe, where Kelly and I talked a little more before I had to head home. I went to kiss her, but she stopped me, saying “Not now.” I didn’t entirely understand, but I didn’t push her any further.

“So- do you want to go out sometime?” I asked. I wasn’t sure if I wanted to be in a relationship with her, but she and I had just had a PG-13 hookup out of the blue, and it felt polite to ask.

“Uh, dude, you’re into my sister. That would be weird if we went out.”

“But giving me a handjob behind Wal-Mart wasn’t weird?”

“Nah, that’s pretty normal for me. Might even happen again sometime.”

“Don’t tell CC.”

She almost snorted. “Why the fuck would I tell CC I jerked off the guy with a crush on her since she was a kid?” Almost immediately she changed the subject, and we talked for a few more minutes as though nothing had happened before I left. I was up until almost 3 AM that night, and just before I went to sleep I replayed the whole scene, with you instead of your sister in the car with me. I came almost twice has hard, and definitely more than twice as much, as I did when your sister had her hands on me.

That was it for any involvement beyond friendship with your sister for a few years. She and I talked like we’d always talked, and you and I kept on laughing, flirting and teasing even more than ever. It was different now, in my mind- I had some idea what your lips would feel like against mine. I knew what your breath in my ear would sound like, with your breasts pushed against my chest and your fingers wrapped around me or running through my hair. Kelly and I graduated, a year later you graduated, and we drifted apart a little.

I was in college by the time you and I started talking again. You were in another state, at a much more prestigious school than I was, but we talked on Facebook and texted frequently. You loved toying with me as much as ever, describing your gradual sexual awakening. Before long, you sounded like you were more experienced than your sister and me combined. You picked up and dropped lovers, male and female, whenever it pleased you. By the time I was a junior and you were a sophomore, our conversations had grown fairly pornographic on your side. I knew how tight you were, what positions you liked, the things you could do better than anyone else- I even knew what sounds you made and how your voice changed in the bedroom, thanks to one very sexy, slightly silly phone conversation. But two boundaries were never broken then- you never sent photos (I had to content myself with your frequent bra or bikini photos on Facebook), and you never engaged with me directly. You could tell me your sexual experiences in intense, almost excruciating detail on the phone or on the computer, but it never crossed the thin boundary into being phone sex or cybersex, even though you knew full well what I was doing on the other end of the line. But our connection was more than sexual- we told each other our dreams, our hopes. There are secrets I’ve never told anyone that I told you in those conversations, and things you told me that I’ll carry to my grave. I promise.

Around this time, Kelly and I started messaging too. She and I talked about less intimate things than we did, both physically and mentally/emotionally. It was just casual chat about college, movies, her shitty acoustic band, and whatever else crossed her mind. Out of nowhere, one day, she brought up the elephant in the room: “u remember when i got u off behind walmart?” Before long, we were talking about that evening, and then we were just talking dirty. Kelly was surprisingly gifted at cybersex, and before long, I was totally immersed in our shared fantasy of walking into the woods together and having slow, rough, animalistic sex against a tree. (Naturally, it was you I was picturing- your tight bell-curve ass in the tiny shorts Kelly described, your golden hair and pert breasts bouncing as Kelly described mounting me. In my imagination, I could hear your breathy, slightly feline moan as I grabbed my lover’s small, tight t-shirt and tore it open at the neckline to expose her chest (your chest).

I was close to cumming as Kelly and I finished our cyber session, and I told her so. “pic 4 pic- show anyone and I’ll kill you,” she messaged back. Not having a smart phone yet, I tilted my computer’s webcam downward, cock in hand, and grabbed a quick few photos. I was throbbing hard enough that I could erupt at any time, and it took a lot of will power and a change in rhythm to keep me from exploding before Kelly sent her photo.

Hers was a LOT better than mine- a mirror shot in which she stood full frontal, smirking at me with one hand on her hip. She was stripped completely naked except for a vest hanging open- the same vest she almost always wore, the same vest she had been wearing when we fooled around in the car.

For the first time, I was pretty sure I knew what you looked like naked, and I pictured you there, in my bedroom, letting your sister’s vest drop to the floor and taking me in your arms. I came harder than I had ever come in my own hand, almost sinking to my knees in pleasure as my semen shot forward into my cupped hand lest it splatter on the walls.

Like usual, Kelly realized where my mind was going. “I should show CC,” she joked when I got back online. “Maybe she’d finally throw you a mercy fuck lol.” I begged her not to, and she said she would delete the pictures as long as I did the same. I took one long, lingering glance to burn Kelly’s body (and your face) into my memory, then deleted the conversation and opened a new, pristine one.

This became a pattern in my life- emotionally and mentally intimate conversations with you, which I would usually follow up with a physically intimate but emotionally neutral interaction with Kelly. She came over for a Halloween party at my university once, and gave me a long, skillful but not particularly loving blow job in the house bathroom. Her vampire costume looked familiar- she had taken it from your closet, and I’d seen you wearing it on Facebook. (I’m almost sure she knew what she was doing- hooking up with the boy her sister had wrapped around her finger seemed to entertain her.)

It all came to a head the next summer, when I went to an award ceremony to see you and a few other friends from near my hometown receive awards for a fundraising event staged at a local theatre. (Remember that place? It used to be an old movie theatre and still had bits of that old 1930s vaudeville glamor about it). You were there with your boyfriend of the time, in a tight blue sheath dress. I sat right next to you, and you whispered to me about the sex you and he had just had before you came. This was the first time you’d been so open with me in person, and I squirmed a little in my seat. Surely you saw how hard I was, my cock standing out like an arrow through my suit pants. “He loves my tits,” you whispered to me. “They’re getting bigger- did you notice? 34-C now. I love it.” I had noticed, and I took one long look down your cleavage, accentuated by the neckline and a gold necklace. When I looked up, you were giving me a look that did not entirely disapprove.

At intermission, while drinks were being served, you slipped away. Shortly after I realized your boyfriend was gone too, I realized what was up. To my surprise, Kelly was in attendance too. I walked up to her and immediately her eyes dropped to my waist, where my pants were still tighter than socially acceptable. “Hey… let’s go downstairs,” she said. I obliged instantly, only hoping that you and your boyfriend weren’t downstairs yourselves. (As luck would have it, you two had taken the opposite route- I remember you telling me about how you fucked him on the roof, your dress pushed up around your waist as he plowed into you on your back.)

Kelly and I didn’t talk much when we got to the basement- just found a secluded area and locked the door. Quicker than usual you were naked and I was halfway there, and I realized we were finally going to have pure, unadulterated sex. I went for my wallet and pulled out a condom, but she told me to put it back. “I hate condoms,” she said, “and I’m on the pill anyway.” I asked if she was sure, and she promised to take a Plan B tomorrow just to be sure. Naked and breathing not quite as heavily as I was, Kelly looked like the you I remembered before that day; her breasts hadn’t taken on the fullness yours had, but otherwise her body remained nearly identical. She leaned forward against the wall and I entered her from behind with some coaxing, a position I had never taken with anyone else. I knew how it worked mainly from movies, but actually adjusting to the difference in our heights took a moment or two. Soon, though, it was just like I’d often dreamed with you: thrusting into her deeper and deeper, my hands stroking her breasts and waist in between stimulating her clit; her kissing me, grinding and slightly gyrating in counterstimulation to my own movements. I pulled her hair (I knew you liked it, and assumed she did. I assumed right), and she gasped. I could feel her tightening around me and knew I had done the right thing. She pressed me down to the floor and mounted me, riding my cock like a professional until she came once more and told me to let go. I burst into her, and as she kissed me while I came, I fantasized about doing the same with you. We dressed and cleaned ourselves up, and made it up in time to see you get your award.

That was the last time I saw your sister in person. Shortly after, she got a boyfriend and we didn’t talk for a while, though I continued to hear all your dirtiest, most intimate secrets firsthand whether you were in a relationship or not. A few years later, Kelly was single again and we began sexting more frequently. It was a smartphone era by then, and soon she was my number one Snapchat friend (you were my number two, albeit a good deal less explicit than my photos to and from her).

The only other part of the story worth telling is of the night you and I were both in New York, just last spring. I was on a business trip, and you were visiting friends. We talked all night, jumping from Mexican restaurant to gastropub before finally getting drinks at the swanky bar outside the jazz club that used to be Studio 54. You were in a small black dress and heels, with your golden hair just as wavy and luminous as ever. I was so intimidated by finally being this close to you after so long that my hands were sweating, and I spilled my Seagram’s 7 on the floor. You laughed, we talked a little more and I asked you if you’d come up to my room.

I don’t know for sure if you were even tempted or not, but you told me, “Not yet. Not this time.” We didn’t kiss outside the hotel as you got into your taxi, but you gave me a long, lingering kind of hug that I knew you intended me to feel every curve of. Then you threw me a wink and said you’d send something special to my Snapchat that night when you got home- one of the only two barriers you and I had NEVER crossed in our intimate conversations.

An hour later, I stepped out of my shower and saw that you had sent me a snap. I opened it, and before I could think about what I was doing, I screenshot the picture before even looking. Then I looked- it was better than I ever expected. Your hair cascaded down around your shoulders as you smirked up at me with a slightly more inviting look than usual. Your generous breasts, fully bare, stood prominent against your chest, with perfectly shaped, perfectly hard, nut-brown nipples. (I hadn’t been prepared for that, as your sister’s nipples were larger, more irregular and definitely more pinkish.) And though you still wore your panties, you had them tugged down enough to show that you were waxed fresh and clean. I had never wanted you more than I did in that moment.

I swore to myself that I would delete the photo as soon as I came, so as not to abuse your trust. And I kept that promise with a clear conscience, but before I even took my cock in my hand, I called Kelly. “Touch yourself,” i asked her as soon as we were both on the phone. “I wanna hear you cum for me.” She complied, more willingly than I expected- maybe she was impressed that I had finally initiated something after years of waiting for her to start. So I lay on my bed, naked on satin sheets in the greatest city in the world, looking at your perfect body for the first time and imagining it was your voice I heard at the other end of the phone as I stroked myself to climax. I told Kelly goodnight when we both finished, took one long look at your photo to memorize it, then deleted it and cleared it from my cloud stream lest I be tempted to grab it back and break my word. I still think about that lost image almost every day.

You and I are back in the same state, miss. As close as we’ve been in almost half a decade. Before I see you again in person, I wanted to confess all this to you. I hope you’re not upset- I hope you don’t consider it an invasion of the relationship we share. And yet, writing it out now, I don’t think you do. In fact, I wonder…

Was Kelly your gift to me? Did you set her up with me as a plaything I could experience you vicariously with, while I gave my body to her and my mind and heart to you? You never played with me in person or digitally, but you did one better: told me every fantasy and then gave me a substitute more inclined to fulfill those desires than you were, while you thought about exactly what we were doing.

All those times I was cumming with her and thinking about cumming for you, I was closer than I thought to doing that, wasn’t I?

I fucking love you so goddamn much right now, miss. Always.

Source: reddit.com/r/gonewildstories/comments/54toli/to_miss_with_love_my_life_with_your_sister_mfmf