I Fucked My Sister's Best Friend

This is a story that started about six months ago. At the time, I didn't think I'd be proud of it, but now, I'm pretty fucking proud of it.

At the time I was 27 and single. My sex life has been fairly active the better part of the last decade, but about six months ago it changed rapidly. It had been something like a month since my last sexual encounter. That had been in January.

One day in February, my sister - Brittany - invited me to her apartment for a game night with some friends. We're fraternal twins, so we grew up fairly close and shared a lot of the same friends. I don't remember what the game was that particular night. We'd played several times before, usually with a fairly consistent group.

On this particular occasion, Brittany's roommate, Kelsey, had joined us. Unlike the rest of the group, we didn't grow up with Kelsey. She and my sister had met in college but became fast friends. Honestly, I'd always had an eye for her, but at the time we lived in different cities and I never thought much of it.

After college, she and Brittany decided to keep living together. Some time after graduation, I had moved into the same city for work. It was good to have some people I knew in my new town, even if one of them was my bitchy sister. (I say that semi-jokingly. She's not really that bitchy, it's just part of a persona she puts on.)

Whatever the game was that night, I ended up paired with Kelsey. No problem, I thought. She was wearing a white tank top, clearly with no bra. Odd choice for February, but since we were at her apartment I guess it wasn't too strange. I figured if I played my cards right (no pun intended) I could get a couple good looks in.

Our game had been going a while when I got a text from my sister. "Want me to turn the temperature down?"

I was confused for a minute and sent a simple "?".

"So her nipples will get hard," read the response.

Obviously I had gotten caught staring at Kelsey's chest. But, honestly, it was hard not to. I go crazy over small tits and Kelsey's are that perfect blend of small, yet perky. The way she leaned across me to draw cards, it was hard to believe that on some level she wasn't putting on a show.

(Have you guessed who I'm going to fuck, yet?)

But nothing happened that evening. I went back to my own place, still a relatively empty space since I'd just moved in back in November. The next few days were completely uneventful, although from time-to-time, a nice visual of Kelsey slightly leaning over me came back to mind.

One night, I was scrolling through Instagram and happened to see a photo Kelsey had posted. It wasn't anything overtly sexual. Not even a bikini throwback, but something about her smile got to me. I liked it and moved on.

A few minutes later, my phone dinged. I was surprised to see an Instagram message from Kelsey. Just a smile emoji, but I took the bait. I sent a smile back. A few more minutes went by and Kelsey responded with a "What are you up to?"

We talked off-and-on the rest of the evening, never much more than just a little flirting. I didn't expect it to go anywhere, so I honestly didn't put a lot of effort into it.

A week later, the group got together again for another friend's birthday. We were meeting up at a restaurant for lunch and I arrived a couple minutes early. Brittany and Kelsey came together.

When they got out of Brittany's car, Kelsey took an awkwardly long look at me. I didn't think much of it at the time, and she went in to put our group on the waiting list.

While she was inside, Brittany looked over at me. "You'd better not fuck her."

"Um, excuse me?"

"I know she's into you. But she's my first roommate I haven't absolutely hated. You can't mess this up for me."

"Whatever."

Kelsey came back and not much more was said about Brittany's threat.

When we sat at the table, Kelsey sat next to me. I don't think it was on purpose, but it definitely altered the course of events.

Shortly before our group finished, Kelsey leaned over to me. "Did she give you the same warning she gave me?"

"Yeah, she did."

"Want to really piss her off?"

Fuck.

At that point our group left the table and moved outside. I went back up to Kelsey. "You would seriously do that just to piss off your roommate?"

"I mean, I wanted to do it before. But now I know you do, too."

She had me there. After that night of cards there had been several occasions where I remembered her perfect tits, those small breasts I imagined were barely a handful.

"So, how do you propose we do this?"

"Give me your address and I'll meet you there. Tonight."

I didn't take much convincing.

That afternoon, I went back to whatever I'd had planned. I made sure to get home a little earlier than usual. I grabbed a quick shower and put on a shirt. I started to grab some boxer briefs, but realized a bit too late that I hadn't done laundry in longer than I care to admit.

Who cares? I thought. I was going to be taking them off in a few minutes, anyway, so I just didn't bother.

I sat on my couch and got my phone out. There was a text from Kelsey: "going to be a couple minutes late."

Fine, whatever.

I sat on the couch and I'd be lying if I said I didn't stroke my cock a little.

I got distracted playing on my phone and lost track of time. The next time I checked the time, it was an hour after Kelsey was supposed to arrive.

Did she seriously back out? Not the end of the world but it would have been nice to get a warning before devoting a whole night to this.

I sent Kelsey a text: "Not coming?"

A couple minutes ticked by with no response. I figured I'd head back to my bed and stroke one out to let out some of the tension.

I got in bed and started massaging my balls. It couldn't have been more than a minute or two before I heard my front door open. Finally.

I couldn't see it from my bed, but the door closed and somebody sat something down by the door. Kelsey called out to see if I was still home.

"In here," I called back. I was still ticked she made me wait so long.

She stepped into the doorway and took a long look at me. "Couldn't wait to get started?"

She didn't just say that. Seriously?

"Get up here and blow me," I said.

She made a bit of an "mmm" sound and made her way to the foot of the bed. She was wearing a cute yellow button-up shirt and black shorts. Kelsey eyed my cock, probably trying to decide exactly how she wanted to do this.

I spread my legs a bit to let her get up on the bed. She leaned in and reached forward with her hand, making a little fist around my dick.

In an instant, my cock stood up, at least 85 percent hard. She smiled and bit her lower lip, then dove between my legs. She kept her hand on my shaft and worked it through her fingers. Finally she took a deep breath and opened her mouth for me.

I reached down and ran my right hand through Kelsey's hair. It was straight and brown and just about long enough to cover her nipples, if she wanted it to.

I guided my cock into Kelsey's mouth and let her get accustomed to having that much inside her. She instantly cracked a little bit of a smile, then went to work.

It may have been the best blowjob of my fucking life, up to that point.

Kelsey clearly knew her way around a penis. She first swirled her tongue around its head, getting it nice and slobbery. Her left hand instantly went to my balls, fondling them and inching up toward my shaft.

I threw my head back and let her take control. A few moments later, her head came off my cock as she let her hands take over. She massaged my whole dick, both hands rubbing, pulling, and jerking with clear familiarity with the male anatomy.

Kelsey dipped her head down, licking her tongue up and down my cock. Then she took it back in her mouth, sucking it deep, but not quite enough to be considered deepthroating. Her hands continued working the base of my shaft, squeezing and releasing with expert precision.

She finally came up for air, but only for a moment before she dove lower, this time taking my left ball in her mouth. She tugged at it for a moment, one hand stroking my dick and the other grasping toward my chest.

That girl could've made me cum right then if she wanted.

Fortunately, she didn't want to. Not yet.

"Take your clothes off," I ordered.

She moaned, but just barely. "Yes, daddy," she said.

If there was any possibility my cock could've gotten harder, that's when it took its opportunity. I'm not exaggerating when I say I'd never been harder in my life.

Kelsey stood back up as I repositioned myself on the bed. Her hands went to her shirt. Her fingers danced over the topmost button, and it felt like an agonizingly long time before she finally unbuttoned it.

I was very nearly insulted--it was almost as if Kelsey thought this was the first time I'd seen naked tits before--but, let's face it, I'm a 27-year-old guy at this point, and she's got breasts that I really want to see.

I'd gotten a very minor preview at the card game, so I had some idea of what to expect.

She finished with the last button, then slid the shirt off her shoulders and let it fall to the floor beneath her. I sat up on the side of the bed and put my hand around her back, pulling her close to me so I could get a close look at her tits.

They're fucking perfect.

Like I said, I go crazy for small tits. I found out later that she's a 32B, but that might be pushing it a little.

I cupped her right breast in my hand and licked underneath, from her stomach to her nipple. She giggled a little. I licked around her nipple and began to suck on it, just enough to make her shudder.

"Do you like them?"

I didn't respond except to turn her around and cup her breasts, squeezing them as I kissed the back of her neck.

My right hand made its way down to her stomach. Kelsey turned her head back toward me and gave me a long kiss. Her hips began to grind slightly against my penis, drawing a not-insignificant volume of pre-cum.

Finally, Kelsey stepped forward and dropped her shorts to the floor.

If her tits were "fucking perfect," as I described them earlier, there are no words to describe her ass.

It's got almost a bubble shape to it, not absurdly big but not flat either. Clearly she'd put a lot of work into it. The kind of ass that a thong was made for. The kind you just want to shove your face into and eat.

She turned around and gave me the full-frontal display. Her incredible tits gave way to a long, smooth torso. A little lower, her stomach retreated down to that magnificent zone between her legs.

I didn't quite yet get a full view of her pussy--that wouldn't come for about 10 more seconds--but I could tell she was completely hairless. Whether she always kept it immaculately maintained or whether she had done it just for me was still a question.

She climbed up on the bed, giving me a fantastic view of her butt in the process. She got on her back and spread her legs, as if to let me know it was time.

I wanted to shove my cock inside her but thought better of it--her pussy wasn't nearly wet enough, and besides, shouldn't I take my time and get an up-close look at that clit?

I dove in headfirst and spat on her mound, using my hands to move my spit around her pussy. She smiled and moaned slightly as I worked her pussy with my fingers. After a brief massage I pushed my right index finger inside her, making sure to lick her clit as I did so. She threw her head back and moaned, her pussy getting wet not just from my saliva, but now from her own juices.

Her pussy tasted incredible. And it wasn't just the taste. Licking a completely shaved pussy is one of the ultimate joys in life.

At this point... It was time. I needed to be inside this girl.

I grabbed her hips and pulled her up, indicating that I wanted her to flip over. I wanted to see that ass bounce as I fucked her.

Imagine - all this just to piss off my sister.

I took my cock and rubbed it against Kelsey's pussy. She was on her hands and knees; I stood beside the bed with my cock aligned with her pussy from behind. She lowered her head, ready for me to enter her. I teased her pussy with the tip of my cock, letting it slide up and down against her tight opening.

Just before entering her, I had a change of heart. Remember how I said she had an ass you just wanted to eat?

Seeing it right there in front of me, I had to go for it. I pressed my face to her ass, running my tongue from her pussy up to her asshole. She let out a loud squeal--her loudest yet--and then a "yesss daddy."

I reached out with my tongue, swirling around and giving her what I later discovered was her first rimjob. She buried her face in my sheets, moaning muffled "fucks" and "daddies" into the bed.

My hands explored her body, from her hips to her legs and feet to her ass. I found the perfect rhythm with my tongue, alternating flicks and circles to give her what she wanted.

Kelsey reached one of her hands to her pussy, rubbing herself furiously as I worked her ass. Before too long, her hips were nearly shaking. Suddenly her body got much sweatier, she let out a loud "FUCK" and she stopped rubbing. She lowered her hand back down and looked back at me.

"Thank you, daddy."

Finally, my cock wouldn't wait any longer. I stood back up and pushed my cock past her opening and inside her warm, wet pussy.

I repositioned myself slightly and started thrusting into her. It felt so good--the full length of my dick entering her body, my balls pressing against her at the conclusion of each thrust.

It took a good couple of minutes to find a rhythm that worked for both of us, but once we did, there was no stopping us. She rocked her body back toward me in perfect unison with my hips thrusting into her. Every thrust produced a thwack as my balls slapped into her. Maybe some of those thwacks were my open palms slapping her ass.

Kelsey angled her neck and looked back at me again, her big blue eyes wide as my cock stretched her apart. She reached a hand down to her pussy and rubbed her clit, then dug her face back into the sheets to let out more moans.

I rested a hand on her lower back, still fucking her at a rate of about 2-3 thrusts per second, sweat starting to bead up on my forehead, chest, and neck.

"Fuck me good, daddy," Kelsey shrieked.

That was it. I felt an orgasm building inside me. There was no use in trying to suppress it--it was happening no matter what I wanted.

I gave her ass one last, massive spank, then pulled out of her--I was pretty sure I'd heard her talk with my sister about some pill she was on, but still.

First I felt that familiar rush when my orgasm began, then a brief high... then my cock exploded magnificently. Thick ropes of cum started shooting out of my dick, landing on Kelsey's back from her ass to her shoulders. There were probably 4 or 5 good lines of cum by the time it was done, along with 6-7 more shots worth of cum pooled up near my cock.

Kelsey took a moment to compose herself, then lowered herself onto the bed.

She, too, was drenched in sweat. She looked fucking sexy lying there on my bed, naked and vulnerable, my cum dripping from various parts of her back.

"You know, you could have cum inside me."

"Next time," I said.

She reached down and started rubbing her pussy as she smiled up at me. My cock was still half hard, so I used it to trace some more cum over her ass.

"Hey," she said, "I want Brittany to know what we did."

"Text her."

Kelsey got up and fished around in her shorts for her phone, then jumped back on the bed, facedown.

Before I knew what was happening, she handed me her phone. "Take a picture of my ass."

"What?"

"Take a picture of my ass. Hurry, before all your cum drips off me."

I stupidly obliged, still not quite in my right mind after an amazing fuck.

And that bitch sent the picture to Brittany.