I Fucked My Sister's Best Friend Ch. 04

I hadn't spoken to my sister or her roommate in four months. In fact, I'd been avoiding them like the plague. I had only let Brittany suck my dick for about 10 seconds, but it had irrevocably changed things between us.

Well, 20 seconds. Then I pulled out of her mouth and got out of the apartment as fast as I could.

My twin sister had sucked my cock.

My twin sister had sucked my cock.

But just for 45 seconds.

Over the next few months, I'd developed new habits. I avoided stores I knew Brittany frequented. If I needed to drive across town, I went the long way to dodge driving past the apartment. I muted my text conversations with Kelsey. I knew it would just take a single "I'm horny, daddy" and I'd be diving quite literally headfirst into her pussy.

Those were the good habits. I'd also developed several less-than-healthy routines.

The first month, I didn't go out much. Things were never really defined with Kelsey, so it was hard to call our separation a "break-up". We just weren't having sex anymore. About three or four nights a week, I stroked myself to sleep, usually draining my balls as my phone played porn on the bed beside me.

The second month, I went out and had a one-night stand with a girl I knew only as Aubrey. And then one night led to a second, and a third, and then I stopped keeping count. Aubrey was an easy way to relieve stress. We didn't know each other's last names and I suspected that she'd given me a fake first name, too. I didn't have her phone number and we never met at either of our apartments. We always met at the same spot in the same restaurant and ended up in a hotel room at a nice place that I suspected someone in her family owned. Neither of us wanted to know anything about the other, neither of us offered any information, and neither of us, presumably, cared in any way.

Aubrey liked having rough sex. I mentioned that sex with her was a great stress reliever - after everything with Kelsey and Brittany, I had a lot of pent-up emotions. Aubrey was an easy and extremely unhealthy way to deal with things.

The kind of sex Aubrey liked was raw, intense, and devoid of any emotion. If my "relationship" with Kelsey was defined by a lack of attachment, my arrangement with Aubrey was even more depraved. Things often escalated quickly.

One night, about two months after I'd started meeting up with Aubrey, I met her at our usual spot. She was wearing a tank top and shorts that didn't make it even halfway to her knees.

Without a word, I followed her out the door and to the adjacent hotel. In the lobby, my mind (as it always does) went into overdrive. I'd made this walk to the elevator at least a dozen times. Every single time I wondered if the bellhop or the guy at the front desk ever recognized us from our previous encounters. It was stupid. If they even recognized us, what then? Who cared if someone whose name I didn't even know had noticed I was having regular sex with someone else whose name I didn't know?

In the elevator, I stood behind Aubrey and admired her petite frame. She couldn't have weighed more than 100 pounds. Her darker blonde hair fell to her shoulder blades and even seeing her tiny, firm ass in shorts was enough to get me hard. Aubrey reached her hand back to my pants - I was wearing something rather loose-fitting - and took hold of my cock. She looked over her shoulder and flashed an evil grin before the doors opened and she stepped into the hallway.

"Get in there," I said, motioning to our room.

Before the door was even shut, Aubrey crossed her hands and gripped the bottom of her tank top, uncrossing them as she pulled it over her head. I turned the deadbolt and slid the safety lock across the door, then turned around to look at her. She'd already pulled her shorts off to reveal a simple gray cotton Calvin Klein thong.

Like I said, things with Aubrey often moved quickly. I admired her slender body, her narrow waist curving out to hips complimented with a perky, tiny butt.

She moved across the room toward me and stood up on her tiptoes to kiss me. I took her ass in my hand, giving it a squeeze as I returned her embrace. Her cute ass constituted barely a handful, a soft mound of flesh that sent all the blood in my body straight to my penis.

"You look like such a sexy slut in that thong."

"Fuck you," she replied, sliding her thong down to her ankles and kicking it away.

"Fuck me? How about I just fuck you?"

Aubrey turned and crawled onto the bed, lingering long enough to give me a preview of her pussy and her tight asshole. She got on her back as I slipped out of my clothes and climbed up beside her.

Once on the bed, I pressed the palm of my hand against Aubrey's mound, rubbing her pussy and giving her the opportunity to grind against me. She moaned a little, working to get comfortable. She looked amazing lying there, her body fully on display for me.

Her pussy wasn't yet wet, so I spent some time massaging her body in an effort to get her turned on. I pressed on her mound and used my other hand to draw circles on her pussy lips with my middle finger.

She moaned some more, but before too long, rolled over.

"Look in the drawer," she commanded, pointing at the dresser across the room.

I smiled a little, knowing exactly what she wanted.

Aubrey had a thing for getting tied up. I knew I'd find all kinds of toys in the drawer, from handcuffs and ropes to gags and whips, and that was just the beginning. All kinds of toys that could be used to restrain her, administer pain, or penetrate her little body.

I opened the drawer and took inventory of what I saw. I had a couple positions in mind, so I grabbed a length of rope, a narrow leather crop, and some handcuffs and leg restraints. Just for fun, I also carried over a pink ball gag and a glass dildo. It was about 7 inches and curved, but otherwise had no texture. On one end was a slightly wider ball designed to stretch out whatever hole it was entering. And, as always, a bottle of lube. This lube in particular was designed to taste like mint chocolate chip. Exactly what you want a girl's pussy (or ass) to taste like, I guess.

I set most of the toy collection down on the bed, away from where I anticipated the action would be. Aubrey put her hands behind her back, eager for me to tie them together. I threaded the rope around and between her arms, making a bit of a figure-eight shape with it to ensure she'd be nice and secured.

"You look so helpless," I commented.

"Are you going to drool all over me or are you going to use me?"

I laughed a little bit, then grabbed the crop and ran it over Aubrey's butt.

"You wouldn't hit my ass with that, would you?"

"Only if you've been naughty," I replied.

She bit her lower lip and spoke with a soft voice. "I'm not naughty."

"You're such a bad liar," I said, raising the crop and hitting Aubrey's ass with it.

"Fuck!" she exclaimed. "What was that for?"

I chuckled a little and let the crop dance over her cute, tanned, peach-shaped butt. She moaned. "Why am I all tied up? Did I do something wrong?"

I hit her ass again, causing her to let out a short yelp. I did that five or six times in no particular rhythm, wanting every thwack against her butt to be a complete surprise.

After the fourth, I noticed some red marks forming on Aubrey's ass. I took a moment to cup her butt in my hands, caressing her, squeezing her, playing with her. The light touch after such a rough spanking elicited a whimper from Aubrey. She writhed around and bent her legs at the knee, raising her feet in the air. I noticed a wet spot on the bed, her body betraying her and letting me know that clearly, this girl was turned on. Her bald pussy glistened with her obvious wetness.

"I want you inside me," she purred.

"Not yet." I took the crop and gave her bare ass another hard spank. "Oops."

"Fuck!" she yelped. "You did that on purpose."

I leaned over her and gave her ass a kiss on her left cheek. She inhaled sharply, the slight pressure from my lips almost too much for her raw ass to bear.

"Please just fuck me..."

I relented—not that I didn't want to fuck her—and rolled her over onto her back. Her body looked slightly awkward with her arms mostly held out beside her, still tied together. Aubrey's pussy was fucking wet. A thin film of her wetness covered most of the skin I could see, stretching at least from her vagina to the top of her mound. I ran a finger down her pussy and pressed my thumb slightly inside her.

"Give me your fucking cock," she said.

"I think you're forgetting the position you're in here. Who gives the orders?"

"You do." She smiled just barely enough to break through her fake helpless façade.

"That's right," I said. I took the crop and drug it over her stomach, moving it down toward her pussy.

"Fuck, are you going to whip my pussy?"

"Yes." I raised the crop and flicked my wrist downward, thwacking it against her wet mound. Not nearly as hard as I'd hit her ass, but enough for her to derive some pleasure. I kept my right thumb lodged inside her vagina and used the crop in my left hand to alternate fondling and striking her gorgeous wet mound. I kept my thumb firmly inside her, using my remaining fingers and palm to cup her ass. She giggled and squirmed with excitement. This girl was fun. Maybe a little more extreme than I was used to, but she was always a reliable fuck.

I decided she'd had enough and threw the crop down to the floor. I withdrew my thumb from her pussy and positioned myself on my knees in front of her.

"Are you going to fuck me now?"

"I'm going to have to gag you if you don't stop asking me questions."

"Promise?"

I smiled down at her, gave my cock a couple of tugs, and rubbed the tip along her slit. I slid into her at a slightly awkward angle. She held her breath as my dick made its way inside her, spreading her pussy apart. I pulled out of her and rubbed against her wetness again, lubing it up before repositioning and re-entering her.

Now at a better angle, I easily pushed into Aubrey's pussy. After that first push, there was no hesitation. I moved my body back and forth, pushing into her, balls slapping against her, all the usual movements. I took her legs and held them together over my shoulder, forcing her to hold her hips a little higher for me.

For a brief moment, I felt one with her. That was probably more what "love" was intended to be, but that wasn't what this was. Not even close. This was indulgent, reckless, carnal fucking. The less attachment I felt to Aubrey, the better. I existed to let her act out her dark fantasies. She existed to be a convenient repository for my semen.

I let go of Aubrey's legs and steadied myself with both hands on the bed. The change in angles meant I was hovering almost parallel with the bed, Aubrey's knees almost touching her chin. Her pussy opened up magnificently. My cock had no trouble operating with piston-like reliability, sliding, skating, gliding through her body.

Science can try to define the mechanics of sex, the biological processes that happen at the microscopic level in the brain and inside the sexual organs of both partners, but there are no words to adequately describe the exquisite feeling that comes from burying your penis in a woman's vagina. I'll never know if Aubrey, or Kelsey, or Sierra, or any other girl ever felt something comparable during that kind of penetration. I hope they did.

Aubrey relaxed her body, allowing me full control over her. She kept her arms, as much as she could, behind her side, still completely helpless and at my mercy. I grinned down at her. A bead of sweat formed on my upper chest and ran down toward my penis. I pushed Aubrey's legs to my left, forcing her body to turn onto her right side. I held her at a sort of L-shaped angle as I continued pounding her sweet little pussy.

Her newly-exposed ass looked so cute. I used my right hand to give it a big spank. She cooed a little.

I pulled out of Aubrey's pussy and rolled her back onto her chest.

"Are you going to cum on me?"

"Not yet."

"Are you going to spank me again?"

"Remember what I said would happen if you didn't stop asking questions?"

She giggled, obviously wanting the gag. First, I undid the rope from around her arms. She stretched out and let out a big sigh. She started to roll face-up, but I put a hand on her upper back and held her there.

"Not yet."

"Mmm," she moaned. "Use me."

I grabbed her left wrist and guided it toward the headboard. With my other hand, I picked up a pair of Aubrey's handcuffs and attached one end to her wrist. I drug her forward, attaching the other end to the bedpost. I silently grabbed her other wrist and did the same on the opposite bedpost. Next, I attached each of her ankles using Velcro restraints to the foot of the bed. The result was Aubrey lying facedown, all four limbs stretched in opposite directions, completely helpless and waiting to be fucked.

"Forgot one thing," I said. I picked up the ball gag and put it in her mouth, wrapping the strap around her head and buckling it tightly against her hair.

Aubrey wiggled a little, testing her restraints. She moaned approvingly. Then, I climbed on top of her, knees resting on the bed on either side of her hips, and took her ass in my hands.

Her ass felt so supple in my hands, two perfectly melon-shaped orbs currently decorated with several red marks from before. I struck it again, this time with an open palm. Again and again, I smacked her bare butt and watched as it gave a slight jiggle. Each time, she recoiled a little, her body got a little wetter, and my cock got harder.

After 15 or so good swats, I dismounted and pressed my face firmly against her ass. I don't think what I did can technically be described as a "rimjob"—my tongue never totally reached her asshole—but it was certainly close. I spread her ass and kissed each cheek, then licked circles teasingly around her butt. I opened the lube and squeezed some out over her lower back, smearing it with my hands and tongue all over her ass.

Best mint chocolate chip taste I've ever had.

I sat back up and took Aubrey's dildo in my hand. She turned her head back as far as she could. Her eyes looked back at me, pleadingly, begging me to penetrate her. She needed something inside her.

She deserved something after everything else, so I didn't waste any time teasing her. Instead, I reached my hand forward and plunged the dildo straight into Aubrey's pussy. The glass rod disappeared effortlessly inside her, every inch no different than the last. Inch after inch vanished into her pussy until I reached its base. The dildo now wedged deep inside her, Aubrey let out a massive sigh and one of the loudest—though muffled—moans I've ever heard.

And so it was, I used her dildo to penetrate her wet, slippery pussy, pushing and pulling repeatedly and simulating what likely would have been back-breaking intercourse with Aubrey. After a little while, I pressed my palm against her mound and changed up the angle to press more against the front of her body. From what little experience I had with her, I knew that was probably my best chance of bringing her to orgasm.

I knew better than to try to elicit an orgasm from her body on my own, so I held my hand and the dildo relatively still and let Aubrey do most of the work. She grinded down onto both, bucking her hips back and forth, desperately seeking a climax. For the next few minutes, I watched this sexy plaything twist her body and guide herself expertly into orgasmic release.

As she came down from her high, I pulled the dildo out of her pussy, drug it across her perineum, and pressed it against her asshole. She relaxed into the bed, ready for her anal undoing. I pushed the dildo against her tight starfish, watching as her asshole depressed downward, fighting against the fake penis. I used my hands to ensure plenty of lube covered both the dildo and Aubrey's ass, then slid it inside her. She exhaled deeply as I used her own glass dildo to sodomize her. After the head of the dildo went inside her, Aubrey's rim slowly tightened around the rod, fighting to close up but unable to do so.

Just like I had with her pussy, I pushed the dildo inside her, massaging the inside of her body and watching the shaft disappear into her. Her body looked fucking sexy sprawled out on the bed, arms and legs outstretched, dildo lodged deep in her ass, her entire body reduced to a toy.

I don't know if it is possible to be jealous of an inanimate object, but I felt a sudden sense of envy toward the dildo. I pulled it out of her, letting it exit her ass and further stretching her asshole. Within seconds, I was on top of her again, this time spreading her ass and guiding my cock toward her tight backdoor.

My cock isn't one that you would describe as veiny, but in that moment, I looked down and saw a couple blue bulging lines on my dick. I knew it would be a challenge to last long inside Aubrey's ass, but I was determined to make it happen.

I fucked that girl's butt hard. I placed a hand on the bed on either side of her shoulders, angled my body down toward her, and thrust again and again into her ass. I filled her tight little butt, my penis forcing its way deep in her tushy. I felt her asshole tighten around my cock and felt its perimeter squeeze my dick like a condom being rolled on and off.

Aubrey screamed through her gag, moaning, panting, joyously gasping for air. She pulled tight on her restraints in futility.

I knew she wanted to rub her pussy. I certainly owed her after this.

I felt my own orgasm starting to build inside me. I looked down at Aubrey's ass, a rookie mistake... nothing makes me cum faster than seeing my own dick inside a girl like that. I thought about pulling out and giving her a rimjob or something to prolong my orgasm, but it was too late. Rather than risk pulling out and having an orgasm anyway, I laid into Aubrey, clutching her whole body and lying on top of her, holding my cock deep in her sexy ass.

"Take my fucking cum in your fucking asshole," I said.

My cock exploded inside her. I felt my cum wash over my cock inside her ass. With nowhere to go, some of it oozed out of her asshole and coated my penis. I felt my cock pump my semen inside this sexy girl's butt, simultaneously feeling a wave of ecstasy and a tsunami of exhaustion.

My orgasm finished, but my dick stayed hard, at least for another couple minutes. I spent those precious seconds fucking Aubrey, much slower now. She relaxed back into the bed—she'd tensed up there toward the end—and smiled as much as she could with the gag still in her mouth. I reached forward and undid its clasp for her.

"Fuck, that was so good," she said.

"Yeah, it was. I'm going to owe you something now."

"I'm sure I'll come up with something you can do," she replied.

After a couple minutes of milking whatever cum was left from my cock, I rolled over and crashed to the bed. Aubrey's ass slowly returned mostly to normal despite a trail of cum dripping from her asshole to her pussy and to the bed beneath.

Quickly, I released Aubrey, letting all four of her limbs out of the restraints I'd put her in. She rolled onto her back and spent the next 10 or so minutes playing with her pussy.

She made herself cum after just two. It was the last time I ever saw Aubrey.

***

My time with Aubrey had been unhealthy, to say the least. Obviously, there are a lot of BDSM (etc.) enthusiasts who have great relationships. That time in my life wasn't one of those.

The first night she didn't show, I wondered if I had the wrong date. The second night, I went to our room at the hotel, only to find a nice-looking family who probably wondered why there were so many scuff marks on the bedposts.

I wondered if Aubrey's relative had discovered what she had been using her free room for and had put a stop to it. More likely than not, she'd probably just gotten bored, thought our "relationship" had peaked, and decided to move on.