I Fucked My Sister's Best Friend Ch. 03

After my first anal adventure with Kelsey, we started seeing each other fairly regularly, at least for a few weeks. We never really talked about what we were, which was both good and bad. On one hand, I was getting regular sex with an amazingly talented girl. On the other hand, I never knew if each orgasm she gave me would be the last.

Nevertheless, every fuck session with Kelsey proved to be an incredibly fun experience. On several occasions, we'd fuck for an hour and she'd have me cum inside her tight pussy, sending what felt like gallons of cum inside her body. (Obviously it wasn't actually gallons of cum, but it sure felt like it.)

On one of our nights of fun, Kelsey climbed off my cock and gave me the best blowjob I'd ever received. Her mouth worked my penis expertly, her tongue, lips, and throat working in unison to stimulate every inch of my dick. That night, I had an orgasm in her mouth and got to watch my cum drip down her chin.

On one of our kinkier nights together, I used a pair of handcuffs on Kelsey and drug my cock over her entire body before fucking her and cumming inside her ass.

One night the following week, Kelsey asked me to visit again. Just before I closed her bedroom door, I caught a glimpse of my sister in the kitchen. She flipped me her middle finger, I returned the gesture, and got on Kelsey's bed.

Kelsey spread her legs and I accepted her invitation, using my fingers and mouth to work her pussy. She squealed here and there as my fingers danced around her, one minute massaging her mound and the next pinching her clit. Finally her legs wrapped around my head and I settled in, pushing my tongue against her bare pussy.

She'd groomed well before this latest session, every square inch of her mound completely devoid of hair. Her smooth pussy was already glistening, her juices starting to mix with my saliva. I felt the mixture dripping down my chin as I dove between her legs, repeatedly bobbing my head and shoving my tongue inside her. Inside that incredible, naughty little fucktoy. I spat my saliva into her slit and ran my tongue through, licking the full length of her vagina.

Kelsey's pussy was so soft, so warm... so tight. I pushed my tongue half an inch inside her, teasing her and making her squirm. I let my tongue explore her pussy, enjoying every stroke of my mouth. I moved my right hand to her ass, grabbing what I could manage.

She moaned and finally, in a weak voice, begged me to fuck her.

"Please, Tyler, please, you know I want it."

"I know you do. Why don't you get your lube and give me a handjob?"

She grabbed a tube out of her nightstand and started applying it to my cock. "I can't wait for this to go inside me," she said, her fist slowly stroking my shaft. Her hands slid up and down my dick, spreading the lube all over. The ultra-slippery lube gave her hands an almost unnaturally soft feeling, as if my cock was being stroked and yet somehow I wasn't able to feel a distinct touch. I really love the feeling of Kelsey applying lube to my cock.

"Alright, Kelsey. Get on your back," I ordered.

She obeyed and spread her legs. I got on my knees in front of her, then bent down to kiss her pussy one last time before pounding her.

"Fuck me. Hard."

"Of course."

I slid my cock inside her, letting out a big moan as I felt my dick inch its way in. I don't care how many times I fucked her, that pussy felt fucking amazing.

After getting positioned and balanced on my knees, I started to pump my hips forward, deeper inside her. Every time our bodies made full contact I made it a point to linger ever so slightly and put pressure on her pussy by grinding my pelvis against hers. She moaned with each thwack of my balls against her butt.

"Are you going to fuck my ass tonight?" she asked.

I kept fucking her pussy. "Of course, I am."

"Let me get something first."

I stopped for a second and pulled my cock out of her. I looked down at my dick, rock hard and slippery with her juices and what remained of the lube. I let myself sit on the bed momentarily, stroking myself while Kelsey fumbled around in a drawer.

By this time, I knew Kelsey had a collection of sex toys and I was certainly interested in seeing what she had planned. "Here it is," she said.

Finally, she rolled back onto the bed, a dildo in her hand. It wasn't overly huge, probably six inches or so. It was made of silicone, was veiny, and had a big head and a bit of a curve to it.

The week before, I'd watched her masturbate with it.

"I'm ready, Daddy."

When that girl fucking calls me that--my cock doesn't get soft for a very long time.

She raised her knees nearly up to her neck, giving me ample room to work with. I grabbed the lube and reapplied to my penis, using what was left on the perimeter of her asshole. She moaned louder.

"Fuck my ass. You know how badly I want it."

Of course, I knew. She couldn't stop telling me just how much she wanted my dick inside her tight, cute little ass. This horny fucking girl...

Kelsey set her dildo by her side and used both hands to spread her ass for me. It looked fucking perfect. A tight hole just ready--begging--to be entered.

I positioned the head of my penis on her little starfish, letting her body get accustomed to the pressure, then began my descent. It took some work, but it wasn't long before my cock was inching its way inside her. The head of my dick went in after a couple attempts, her asshole tightening again once the tip of my shaft penetrated her. I repositioned slightly again and continued pushing, hoping to get balls deep in her ass before pulling back for the first deep thrust.

From the look of Kelsey's facial expressions, she somehow still seemed surprised at the feeling of having a penis shoved inside her back door. I looked down at the scene, first noticing her wet pussy, for now just uselessly waiting for a cock that was currently preoccupied with other activities. Under her pussy was my cock, slowly pumping in and out of her ass.

She moaned again. "Fuck, I love it when you use my ass."

"I love it, too."

"You feel so--big inside me."

I smiled a bit. "Your asshole feels super tight today."

It was her turn to smile back. "Shut up and fuck me."

While I continued getting her asshole used to my erect penis inside it, I bent down and took the opportunity to take her left breast in my mouth, sucking and licking her nipple. She arched her back, providing me with yet another angle at which I could push into her. Her breasts felt so supple in my hands and mouth and my cock began to throb with an overwhelming sense of desire.

After a couple minutes, Kelsey grabbed her dildo. I'd suspected she would use it for this and was happy to see that I was correct. I never stopped my rhythm on her asshole as she used her dildo to tear into her pussy. She slid its full length inside herself, masturbating like a pro while I worked her ass with my dick.

Can I just stop for a moment and reiterate how appreciative I am of this vixen?

Every moment like that--my cock in Kelsey's ass and a dildo in her pussy--was pure ecstasy. It felt wonderful, especially in the brief moment in every thrust when the base of my cock made full contact with her body. At one point I thought I could even feel her dildo through the narrow walls of her body. It might have been wishful thinking. I made a mental note to test that theory sometime in the future.

"Daddy, don't stop."

"Never."

She changed the rhythm of her dildo, clearly designed to bring herself to orgasm. I watched as Kelsey positioned a hand over her mound, rubbing it as she worked her dildo knowingly inside herself. I hoped--almost certainly with futility--that someday I would be as familiar with her pussy as she was.

And all the while, my cock was pounding away at her cute little butt.

As long as I live, I will never forget the sexy curve of Kelsey's ass and how it feels being squeezed in my hand.

Finally, her body beaded up in sweat, her natural orgasmic reaction that I was becoming very familiar with. Then, that moment of releases her body finally allowed her to feel a deep orgasm, an overwhelming flood of pleasure as her muscles tensed all throughout her body.

The dildo fell to the bed, having served its purpose. I let my cock slide out of her ass, but otherwise remained in my position, using a thumb to toy with her wet, shaved pussy.

"That was fun to watch," I said.

She took a few moments to compose herself, then eagerly jumped up onto her knees.

"What next?" I asked. She kissed me.

For another 10 or 20 minutes, I fucked Kelsey's ass from behind while we both were lying on our sides. A few times, she gasped and moaned in genuine surprise. At other times she seemed a little more distant, content to let me finish up but otherwise ready to go to sleep.

I shot my cum inside her, letting myself feel the entire orgasm before pulling out and giving her a little tap on her butt.

"You were so good tonight," I said.

Kelsey giggled a little, rolled onto her stomach, and fell asleep.

***

The next day was a Saturday. I woke up alone, in my own bed, having driven myself home after my latest evening with Kelsey.

I rolled over and grabbed my phone. I hadn't bothered setting an alarm and was a little disappointed to find that it was still well before a decent waking hour.

For about half an hour, I caught up on news, social media, and the like. Before long, I found myself casually checking various porn sites for new content. It seemed like I'd been getting pickier and pickier lately, which made finding new material somewhat of a challenge.

A notification bubble appeared next to the Messages app. Certainly odd, seeing as the sun wouldn't appear for at least another hour or two.

It was from Brittany. A short text, just two words:

"I win."

What the fuck was that supposed to mean?

I thought for a few minutes but decided to put it out of my mind until a more decent hour. Brittany always seemed to be going on about something. It was probably some stupid bet we'd made, or some argument we'd had years earlier.

I set the phone down and went back to sleep.

***

A couple hours later, I woke up again--this time, the sun came through the blinds as if to shame me into getting out of bed. I drug myself to the shower and got ready, going about my morning routine and even starting to eat breakfast before remembering Brittany's cryptic "I win" text.

Now that I was up and didn't really have much to do, I replied: "What are you talking about?"

All she sent in response was the coy emoji with a devious half-smile.

I was not in the mood for whatever this was, so I ignored her latest and hoped that was the end of it. But after a few minutes, a saw another notification appear.

There was no text attached to Brittany's message, just a video clearly taken in portrait mode and with not-so-great lighting.

It took my eyes a couple moments to adjust to what I saw on the screen.

She'd sent me a video of someone wearing a strap-on and penetrating a girl in the ass, doggystyle.

What the actual fuck?

My text back to her said just that: "What the actual fuck?"

She read the message but never responded. I navigated back to the video and watched it again. Whoever was doing the fucking was the one holding the camera. The girl getting fucked was clearly into the act too. I watched it and rewatched it a few times.

But again--why would my twin sister purposely send me a video of lesbian porn? And not a particularly well-produced one, at that?

The girl on top--the one holding the camera--pulled the dildo out. It looked just like the one Kelsey had used with me the night before.

I paused the video. That ass was unmistakable.

Then, with sudden clarity, I realized who these mystery girls were.

The dildo in the video didn't just look like Kelsey's, it was Kelsey's.

The ass in the video belonged to Kelsey as well.

It had to be my sister wearing the strap-on. Who else could it have been?

Fuck. I thought there had to be a mistake. Was my twin sister having sex with the same girl I was? Fuck!

I checked the timestamp on the video, which in retrospect was probably a mistake. It was dated for the night before, probably no more than half an hour after I'd returned home.

Suddenly the "I win" message made a lot more sense. But Brittany sent a follow-up: "I can't wait to fuck her again today."

What am I supposed to do with that information? Obviously, Kelsey and I weren't strictly exclusive, or really much of anything to each other beyond several nights of pure, raw sex. Our relationship was completely transactional.

But still... she got fucked by my sister with a strap-on.

The right thing to do would be to take the high road, move on from Kelsey, and hope that someday I'd find somebody else who could give me the mind-blowing sex I'd become accustomed to.

But where's the fun in that?

Right then, I decided that if Kelsey got to fuck my sister and tell me about it, nothing was off limits.

***

Five days and 15 hours later, I was balls deep in Sierra. I'd met her a month earlier on the night of the card game at Kelsey and Brittany's apartment.

Her body was fuller than Kelsey's. Still skinny, but not petite. Bigger tits, probably C cups, and a bigger ass. She was lying on her right side, an arm pulling her left leg high in the air. I was on my side as well, lying perpendicular to her and fucking her pussy from behind.

She was screaming.

I was making some moans of my own.

"Let me get on top of you," she said.

I pulled out and rolled onto my back. Sierra climbed on top of me and lowered herself onto my dick. She leaned forward, lying directly on my chest, her big round tits pressed against me. I reached down and grabbed her ass, at first letting her control the rhythm.

Sierra rocked back and forth on top of me, each cycle bringing maximum penetration followed by a withdrawal, immediately followed by a quick descent back onto my cock. And again, and again.

I gripped Sierra's ass a little harder in an attempt to control some of the rhythm.

"Fuck, Sierra..."

"Yeah, squeeze my ass..."

"You've got an amazing butt."

She giggled a little.

I grabbed her ass tighter. "Let me drive for a minute."

She obliged, letting herself relax her whole body.

I pushed my hips upward once or twice, making some small adjustments but otherwise thoroughly enjoying Sierra's pussy. I threw my head back as I massaged her ass. We worked up a rhythm in which I raised her butt, pulled her back down, slammed my balls against her as hard as I could, and repeated for the next cycle. Her ass jiggled with every repeat, tiny waves running from her butt to her lower back.

It was too much. I shot my cum inside Sierra. She gripped my back as we slowed, eventually lying still, chests pressed together and my cock still inside her.

She rolled off me and sighed. "Think that'll be enough?"

I'd discussed the arrangement with her beforehand. She knew why I was doing this. She'd actually been eager to help out. It was at her suggestion that we'd set up my phone to record the whole affair.

"Absolutely. Revenge sure is fun."

***

The next morning, another weekend, I drove over to Kelsey and Brittany's apartment and knocked on the door.

Kelsey opened it. "Hey, did I forget you were coming?"

"No, I just wanted you to know that I win." I handed her my phone. "Press play."

Kelsey watched as Sierra rode my dick. Her mouth curled up into a bit of a smile. "You fucked Sierra?"

"I did. So, now we're even."

"You know I'm not going to stop fucking your sister, right?"

"What do you mean?" I asked.

"This doesn't change anything. So you fucked my friend. It doesn't bother me."

"That doesn't bother you at all?"

"No, I kind of like sharing you," she said with a smile.

Fuck. All that trouble and it didn't even bother Kelsey? I mean, it was good sex, but Kelsey's response just pissed me off.

"Fuck, Kelsey. You're fucking Brittany on the side?"

We went back and forth for a while. What was the most frustrating was that during the whole argument, I was getting more and more frustrated, and Kelsey never even acknowledged it. In fact, it was almost as if she was encouraging it. Her whole demeanor... it was as if she couldn't understand why I was angry.

And truthfully, looking back, I wasn't innocent in the whole ordeal either. The whole arrangement with Kelsey started as a ploy to irritate my sister. And I was the one that escalated things further by having sex with Sierra.

But at the time, I was mad. "If you keep fucking my sister, that's the last time I have sex with you."

"Don't be mad at me." She started smiling and twirling her hair.

"What did you expect my response would be?"

Kelsey started swaying her hips back and forth a little. Her short dress swayed a little with her body.

I knew what she was doing. "Stop trying to look sexy."

"You don't think I'm sexy?" She looked a little pouty when she said it.

"You're obviously sexy. That's not the point. Stop trying to change the subject."

"Do you want to fuck me?" she asked.

"No!" Yes. Of course, I wanted to.

She turned and walked back into the apartment. She lifted her dress just enough for me to see that she wasn't wearing any underwear. That ass looked perfect. My cock stirred a little. It was... confusing.

Kelsey was an expert at this. Before I could stop myself, I was following her into the apartment. I knew as soon as the door was closed--or maybe even before then--she'd be pulling her clothes off and seducing me.

Sure enough, as soon as I was inside, Kelsey's dress was on the floor, her naked body on full display for me.

I was weak. Kelsey always makes me weak. Just one more fuck. Then I was done.

A couple minutes later, I was on her bed, hatefucking her pussy. This wasn't tender lovemaking, designed for mutual pleasure. This was carnal rage, fleshly hate. This was exclusively for me, a selfish act intended only to release my frustration on Kelsey.

She was on her hands and knees, recoiling as I fucked her doggystyle. I smacked her ass, hard, repeatedly. She was going fucking wild. The harder I fucked her, the further I pushed her, she just begged for more. My cock slid in and out of her like a jackhammer, ramming its full length into her body as far as it could.

Kelsey reached under her pillow and grabbed something, then twisted her arm behind her back to hand it to me. "Put this inside me," she managed as she handed me her buttplug.

I slowed just slightly but didn't stop, using the moment to spit on my free hand and rub my saliva on Kelsey's asshole. Then I positioned her buttplug, gave it a good push with my thumb, and let it fill Kelsey's ass. I kept my thumb pressed on it for a moment as I fucked her.

"Yes, fuck!"

I took my hand off her buttplug and used it to pull her hips backward. I plunged deep into her, her pussy massaging my cock with every thrust of my body.

"Yes, daddy, fuck my pussy... fuck my tight little pussy..."

"Fucking bitch..."

"Mmm, yes, fuck me..."

I put a hand on her lower back and straightened my back, getting as tall as I could while still resting mostly on my knees. I looked down, watching my torso give way to my cock, buried in her slutty little pussy. Just above that, her jeweled buttplug glistened as it reflected the light from above her bed.

Kelsey buried her face in her pillow, screaming. Her ass made an audible clap each time my body smashed into hers. My cock was rock hard, not even close to an orgasm. My anger still seethed, but this was a good outlet for it. I knew I'd still be mad at Kelsey later, but at least I could get it out of my system and punish her a little.

Although the "punishment" just seemed to be making her hornier.