Cumming inside [M]y ex’s sister [F], years later…

When I was in my early 20s, I dated a woman named Catalina (or Cat) who was a few years older than me—a completely stunning half-Argentinian woman with small but perky tits and the most amazing ass.

The story of our (IMHO extremely hot) first hookup: https://www.reddit.com/r/gonewildstories/comments/v46u46/fucking_my_coworker_f_raw_while_our_other/

That one time we tried anal: https://www.reddit.com/r/gonewildstories/comments/vicslj/spontaneously_trying_anal_with_my_coworker_f/

Anyway, Cat and I parted ways after a few months of hooking up (during which time we had some of the most amazing sex I’d ever experienced). As intense as the sexual chemistry was, we just didn’t have much else in common. We were both living on the West Coast at the time, but she moved away not long afterwards.

Fast forward a few years, and I’ve just gone through a really awful, painful breakup with a different woman, so I’m swiping through dating apps for literally the first time ever.

One Tinder match looks vaguely familiar, though it takes me a second to place her…

Then I realize with a start (and the beginnings of an erection) that I’d matched with Elena, my old flame Cat’s younger sister.

While Cat and I were dating, I’d only met Elena once—very briefly. Cat was a few years older than me, and Elena was the exact same number of years younger. At the time, she’d just turned 18 and was finishing high school. We barely interacted and neither of us made much of an impression on the other.

Flash forward to today, and Elena was probably 22-ish and just out of college (while I was about 28, which would’ve made Cat 34). It turned out Elena had really gotten into fitness and was making a living as a barre class instructor.

Her photos made my jaw drop.

She was a classic “VSCO girl.” Every photo featured Elena in skimpy workout clothes or bikinis. And because she’d become a professional barre instructor, her body was one of the most incredible I’d ever seen—like Cat’s, but younger, tighter, more toned, more perfectly proportioned. In the yoga pants, bike shorts, and thong bikini bottoms she’d chosen for her profile, every part of her was on display. Her hipbones, her legs, and especially her ass were just astonishing.

Instantly turned on and figuring I had nothing to lose, I messaged Elena. To my surprise, an hour later, she messaged me back.

I joked about only vaguely remembering having met her before and we caught up a bit (although Cat had since moved away, their family was still in the area and Elena had gone to college nearby).

Then, she started to take things in a new direction.

ELENA: U know what’s weird, is that Cat told me A LOT abt your sex life while u guys were dating. Lol

ME: Wait, what??

ELENA: Lol I knoooooow

ME: LMAO, ack. How weird!

ELENA: I mean we’ve always confided in each other. But also I was in HS at the time and hadn’t lost my v card yet

ELENA: Was feeling super insecure abt my body, etc.

ELENA: Soooo in a weird way, I kinda learned about sex from what she told me about the two of you

ME: Um

ELENA: Obvs I had a lot of great sex in college and since then

ELENA: Buuuut I’ll be honest, what Cat told me set some unrealistic expectations!

At first, I’d figured matching with Elena might be funny—and of course I was rendered completely speechless by her photos. But I never really expected it to go anywhere.

(At least I don’t think I did… )

Now, though, the energy had changed. Even via text, I could feel the sexual tension.

I ogled her photos again, thinking about an 18-year-old Elena picturing me fucking her sister.

ME: What do you mean, expectations??

ME: Like what did she tell you

ME: This is WILD lol

ELENA I KNOW!! Sorry lol. Too funny

ELENA: I mean she said you were pretty well-endowed

ELENA: Girthy, I think was the word

ELENA: And I dunno, I was super horny/sexually frustrated at the time, so I asked her about what you guys did

ELENA: Aaaaand she told me

ME: Wait what did we do

ME: Like, she described the sex we were having?

ELENA: Basically lol

ELENA: Like what positions, how u’d never cum on anyone’s face before hers

ME: OMG WHAT

It was true.

ELENA: How u always came inside her when you guys stopped using condoms

Also true.

ME: I genuinely cannot believe she would tell you this stuff

ELENA: Lol sorry I knoooooooow

ELENA: Super weird

ME: Uh, YOU THINK

There was a pause. My cock was throbbing and I was starting to rub it a little through my pants.

ELENA: Buut also

ELENA: … kinda hot?

ME: I mean for sure

ME: I just feel weird that she told you so much intimate stuff!

ELENA: No, don’t feel weird!! We’ve always talked about literally everything

ELENA: W/ a new bf, even our mom is always like, so how’s the sex

ELENA: And like I said, back then I was a horny virgin

ELENA: I hadn’t even discovered porn yet, so tryna get ur stories out of her was how I got off lol

My head was spinning. My mouth was dry. My cock was close to exploding even though I’d barely touched it while we were messaging.

The thought of Elena touching herself to the thought of me—ME??—was driving me wild. And the fact that she was Cat’s younger sister—I was six years younger than Cat, and Elena was six years younger than me, making her like TWELVE YEARS younger than the coworker I’d had lots of amazing sex with a few years earlier—added a forbidden edge to the thrill of getting sexual with her.

ME: And… did you?

ELENA: ??

ME: Get off

ELENA: Oh lol… yes. Duh

ELENA: Quite a bit

ME: Seriously?? Thinking about me fucking your sister?

ELENA: I guess sometimes, if she described like a particularly hot thing

ELENA: Like the first time you tried anal (YUP told me that one too, sorry)

ELENA: Buuuut I’ll be honest, I mostly just fantasized about you fucking me instead

I’d wondered why she swiped on me, and I figured based on her overtly sexual tone from the very beginning that this was going someplace. But the fact that she was being so forward made me rock hard.

Clearly, we both knew where this was headed… and wanted it to get there. Fast.

ME: OK, my turn to be honest

ME: I’m having a hard time not fantasizing about that exact same thing, right now

ELENA: Well then

ELENA: Imagine that!

ELENA: Maybe we should make it a reality

My heart was beating out of my chest. My whole body was coursing with horniness.

I needed to fuck this girl.

ME: Maybe we should

ME: Where/when?

ELENA: I’m teaching a barre class at 6 but free until then

ELENA: You don’t seem to be doing anything right now

ELENA: Except touching yourself, I hope

ELENA: And I’m like…….. extreeeeeeemely wet

ELENA: Sooooo

The next message was her address. It was roughly 30 minutes away. Which, for the West Coast, is practically around the block.

I told her I’d be there in 45, grabbed a quick shower, and jumped in my car.

Elena’s apartment was a split-level unit in a brownstone on the outskirts of Oakland. She buzzed me through the gate—and then, as I came down the steps, she opened the door.

In person, Elena was slightly more petite than I expected. But her tight body was, if anything, even more stunning, her half-Argentinian complexion lending her smooth, supple skin an added radiance.

She was wearing a tube top that did nothing to conceal the natural curves of her shapely breasts, her nipples poking through the thin fabric. Her ass and legs were on display in form-fitting yoga pants. Her black, shoulder-length hair framed a beautiful face with a distinct resemblance to her older sister, with whom I’d had insane sexual chemistry not so long ago.

Suddenly, at the clear likeness between them and the thought of sleeping with my ex’s younger sister, I felt almost possessed. There was a hunger deep in me; I needed to just devour Elena.

She clearly felt the same hunger, because as I came to the door we were on each other without a word—making out animalistically, my hand coming up to her breast, feeling her nipple under my palm, hearing her moan as I kiss down her neck and bring my other hand up to grope her ass.

Elena pulled me inside and shut the door, guiding me toward the couch and pulling my jacket off. She dropped it on the floor and then started to fumble with my belt.

I pulled her tube top over her head. She was naked underneath. Her breasts looked exactly like her older sister’s, but maybe a little bigger/fuller—with the same dark, perky nipples that hardened under my touch. I leaned down to take one of them in my mouth, making Elena gasp, as she unzipped my fly and pulled my jeans down below my hips, dropping them to the floor.

Both of her hands went immediately to my cock, already rock-hard and throbbing for her. She pulled the waistband of my boxer briefs down and pulled it out, wrapping both hands around it and starting to stroke. I moaned.

“Oh my actual god,” she said, looking down at my dick. “My sister once told me it was as thick as my wrist. And she was only kinda exaggerating!”

Without warning, she bent down and licked a drop of precum from the tip of my cock, making me gasp in surprise. She grinned devilishly up at me when she felt me jump, her eyes flashing. We were both turned on by how filthy this was. She took my tip in her mouth again, lightly, closing her lips around me teasingly and circling my cockhead with her tongue.

But I wasn’t interested in waiting any longer.

Pulling her mouth off of my cock, I kissed Elena forcefully and grabbed her breasts, pushing her against the wall. She moaned and devoured me right back—until I pulled away just far enough to yank her yoga pants down to her knees.

Her panties came down with them, revealing a neatly trimmed bush and prominent labia—just like her sister’s. I licked one finger and dipped it inside of her 22-year-old pussy, sucking on her nipple as I did so and then sinking to my knees so I was eye-level with her bush.

Peeling Elena’s lips open with both hands, I licked up and down her swollen opening a couple of times. She tasted just like Cat: fresh but musky in a way that drove me wild. I worked my finger back into her and focused my tongue on her clit for a few seconds, relishing her gasps as she pulled the back of my head up into her. She was soaking wet and her juices started to run down my chin.

Then, in one motion, I stood up and spun Elena around so she was facing the wall I’d pushed her up against. Grabbing her hips, I pulled them toward me and sank my cock halfway inside her bare pussy from behind. She moaned huskily as my tip, lubricated with her saliva from a moment ago, easily parted her lips and drove partway inside her.

I slowly drew myself out, watching my shaft emerge covered in her juices, her lips gripping me, her perfect ass looking like a younger, tighter version of the one I’d fucked raw a few years earlier.

Then I drove myself slowly back into her, pushing past the depth I’d penetrated before and steadily pulling her hips down to mine until I could feel her cervix against the head of my cock, her walls convulsing, almost fluttering, around me as my shaft filled her completely.

“Oh, fuck yes,” Elena moaned. “You’re splitting me open.”

I looked down and saw that my cock was not yet fully inside her. I’d bottomed out, but she was so petite and so tight that another half inch or so was still outside her lips.

I held myself still for a moment, savoring the way she gripped me, and then began to push the rest of my cock inside her. Elena splayed against the wall, spouting gibberish and pushing her ass back into me. I could feel her pussy stretching around me as I pressed in and up, my precum-coated tip throbbing against the entrance to her womb.

“Fuuuuck,” she groaned. “I can feel you in my stomach.”

There is no feeling in the world like being fully inside a new pussy for the first time, completely unprotected. But the thrill of feeling Elena’s warm, wet insides squeezing me—as I started to thrust in and out, slowly building up a rhythm—was amplified by the fact that everything, from the gorgeous shade of her skin, to the size and feel and taste of her nipples and labia, to the musk of her vagina, to the sound of her moans… all of it was new, and yet slightly familiar. Fucking my ex’s sister was almost like getting to fuck a younger—and, let’s be honest, even hotter—version of my ex.

Clearly, Elena was getting off on the situation, too.

“Does my pussy feel the same as hers?” she asked breathlessly, looking over her shoulder at me while I fucked her from behind.

“Yes,” I groaned, my cock throbbing at the thought, briefly picturing myself sinking my cock into Elena’s older sister.

“Am I as tight as she is?” she asked.

“Y-yes.” This was driving me wild. I could barely keep it together.

Just then, Elena turned back in the direction she was facing, moaned a couple of times as I kept thrusting in and out of her, and then reached with one hand to the knob of the coat closet door. She turned it and pushed the door open, letting it swing it away from her, and then put her hand back where it had been, braced against the wall as I railed her.

I watched the closet door swing open, the full-length mirror on the inside first reflecting coats and hats, and then (as it swung open wider) the entryway of her apartment, before finally settling (as the door stopped moving) on the two of us, just inside the entryway. We both drank in the reflection of ourselves fucking: Elena’s tits bouncing, her supple ass rippling, my balls slapping against her. I used one hand to spread her asscheeks slightly so that we could both see in the mirror where my shaft was disappearing inside of her.

Cat, her sister, had also loved to watch us fucking, often in the mirror above her dresser. The thought that Elena was into the same thing—either without even knowing it, or perhaps knowing full well from their conversations that it was a turn-on that both sisters shared—sent me over the edge.

“Fuck, Elena,” I grunted, still watching in the mirror, my eyes glued to her pussy lips as I thrust in and out. “I’m gonna cum inside you.”

“Oh my god, I feel you swelling up,” Elena moaned. “Fill me up—fill me. The way you filled her.”

With that, my balls tightened and I felt the most incredible release as my pent-up load unleashed deep inside of her, my cock twitching as it pumped rope after rope of semen against Elena’s quivering walls. She moaned as I pulled her hips down, driving myself even deeper as my orgasm peaked and then subsided, the muscle spasms ebbing as I pumped the last of it into her.

Elena twisted around to kiss me while I was still inside her pussy and I had flashbacks of the first time I’d ever cum inside of Cat—after a desperately hot fuck, without anybody even mentioning birth control. Just like me and Elena, just now.

Slowly I pulled my softening cock out, savoring the feeling of her lips gripping me tightly as I withdrew. My sperm began to leak out of her almost immediately, but Elena stuck a hand between her legs to prevent herself from dripping onto the floor as she awkwardly waddled—her yoga pants still just below her knees—over to the chair in her living room.

Laying down on it, on her back, she scooped the cum that was running out of her pussy into her mouth, swallowing it, and then pulled her lips open, staring down at the semen that kept dribbling out of her pink opening.

“There’s so much of it,” she said.

“Do you always let guys cum inside you?” I asked, peering in at our juices as they pooled against the entrance of her pussy.

Elena nodded eagerly. My softening cock twitched.

“I fucking love it,” she said. “Especially the first time a new guy fills my pussy.”

I started to reach for her, figuring it was her turn to cum, but she shook her head teasingly, waving me away and then reaching down to pull up her lacy underwear and yoga pants.

She sat up, adjusting the waist of her yoga pants. My cum was sure to be leaking through them already. I looked at her quizzically.

“You can make me cum later tonight,” she said. “But I have to go teach a barre class in a few minutes.”

“Oh, geeze, right!” I said, checking my watch and starting to gather up my clothes. “Sorry, I can get out of your hair—”

“Or you can stick around and we can do this again in like an hour,” she said, getting up and walking into her room. She came back a second later putting on a black sports bra. “Up to you! Towels in the bathroom are clean if you wanna take a shower. And there’s some weed and rolling papers in the speaker cabinet, if you know how to roll a jay.”

I was sold even before the weed, but that put it over the top.

“See you back here in an hour or so,” she said, giving me a peck on the cheek as she grabbed her bag and headed for the door.

I went straight for the weed. This was going to be a fun night.

*Thanks for reading/reacting!! If people like this one, will get to work on Part 2…*

Source: reddit.com/r/gonewildstories/comments/vjwvhe/cumming_inside_my_exs_sister_f_years_later