Welcome to New York

I hit jackpot on the last drawer which contained a deluge of items ranging from boy shorts to a pair of crotchless panties, something I immediately stored in my memory for later use. And after very little searching the prize was found, right next to a large dildo that was a few inches shorter than what I offered but just as thick. An idea formed quickly.

As I returned to the apartment's living room Jane glanced back at me, her face still flush and her pussy dripping a combo of our cum. Her eyes widened as she saw the dildo in my hand and my fully erect cock bouncing along with each of my steps.

"How the fuck are you still hard?"

"One last hole I've yet to cum in."

"You think I'm giving up my ass on the first date?"

I laughed out loud at this remark. Her face got more red like I had embarrassed her with my deep laugh.

I said, "Date? This isn't a date, this is me giving the neighborhood slut the fucking she gets so wet for."

Her eyes twinkled with lust, her body scrunched up anticipating another orgasm, her mouth fell slightly open. In that moment I slapped her ass again. Then the other side. Then the other. I continued slapping her ass until it was the same dark red shade as her hair. Running my hand between her legs I could feel her wetness. My finger found it's way buried two knuckles deep then pulled out and rubbing at her puckered asshole. Jane took in a deep breath as I had taken that same finger and begun inserting it into her ass.

I was surprised how little resistance she put up as her body seemingly allowed me to violate her last hole. With my other hand I reached into my pocket for the lube and noticing for the first time that it barely at a fourth left. This little slut either had this bottle for years or she burned through it like a wildfire through the forest. Leaning in I brought my face next to hers, just within distance to whisper.

"How often do you stuff this toy up your ass?" I asked her, slightly curling my finger in her ass. Her face grew red with shame and she dropped her head trying to hide in the couch.

She answered, "Once or twice a week."

Once or twice a week. I had hit the whore jackpot.

"Sometimes three."

"Three times a week?" I asked her, almost in disbelief. Her face broke into a sly gin as she stared back at me.

"If you're about to do what I hope you are it will be four times this week."

My cock near burst right then and there. I reached for her face and shoved my tongue down her throat. It was primal, her lip biting into mine as we pulled part then immediately connected again. My dick throbbed as I held it in my hand, slowly jacking off out of instinct. Pushing her away from me I stood back up to get her ass ready for the real show. Pulling the lube from my pocket I squeezed a bit onto my finger tip and immediately began sliding it around into her asshole. Her whimpers came out, just barely audible.

The dildo sat next to me which I grabbed by the base and pulled my finger from her ass to squeeze some lube onto the purple toy. Was it an odd to jerk off a silicone penis to apply lube? I found out soon enough, and while definitely odd, that this was going to be worth to this weird sensation. As I placed the tip around her rim she gave a coo and shook her hips back and forth.

"Fuck, you are hot!" I blurted out as I watched her ass cheeks jiggle back into place.

She giggled, eyes traveling down my body and settling onto my cock before saying, "You're not too bad yourself."

"You ready?"

"Fuck yes."

As she spoke I began to push the thick shaft into her ass which put some resistance up. With a little wiggle of the toy her ass ate it up. The first two inches slid in easily, she pulled in a huff of air.

"Slower, oh fuck, slower!"

I slowed up but her ass still pulled it in further. The next inch then the next was sucked in. Her ass was tight and now filled with six inches. Slowly I pulled back a few inches then pushed it back in. The couch rocked slightly. My cock ached watching her give out moans and I felt between her legs. Her pussy was dripping with some sort of combination of my earlier load and her juices. She seemed ready.

I stood behind her and plunged the dildo in one more time before pulling it out completely. Jane's ass gaped slightly as it closed after it's intrusion. I took the lube and applied a good amount to my dick. It was pretty oiled up by the time I stepped up behind Jane's pert ass. I gripped her hip and ass in the palm of my hand.

"Don't go rough," she said as she stared in awe at my cock pointed towards her ass.

"No promises," I said with a smirk and a slow push into her ass. As the head of my dick began opening her it stopped well before the head could make way. Gripping the base I pushed harder until the helmet of my cock finally busted past her ring, I tried my best not to rush it but still ended up with about an inch more than the head lodged in her ass.

"FUCCCCKKKKKK! That's fucking thick!"

I couldn't help but laugh at her predicament. Less than twenty four hours ago this petite little red head had met me, her newest neighbor, and already I had my dick in her ass while the neighborhood watched. I used both my hands to grab her by the hips and push further into her. Jane shook her ass slightly as I worked my way in.

About six inches in she slapped my leg and begged, "Stop! Stop! Stop!" Her voice had gone from a whisper to a shout.

"Should I stop?" I asked.

"Fuck no! Just a pause moment to catch my breath."

Slowly I pulled myself back out to just my last inch, gave her a few seconds before I thrust back in, my dick making its way further into her ass.

"You like this dick?" I grunted as I thrust myself into her ass.

"Yes," she answered as I reached out and pulled her head back with my hand around her neck.

"Beg for it."

"Mmhhhmm, fuck me!"

"Beg!

"I want you to fill my ass! My fat ass is yours, now take it!"

I began pulling into as deep as I would go until I finally bottomed out. Thirteen inches of cock stuffed into the ass of woman who barely stood five foot. I could feel myself pulsing in her ass as I'm sure she could too.

"Yes!!" Jane shouted as she felt my balls slap her pussy lips. With that I executed my final move and lifted her up. Taking a couple steps back I released her again and she had to outstretch her hands to the back of the couch to keep from falling to the ground. I now gripped her hair with my hand and pulled her head back to give me access to her neck. I kissed right behind her ear and she turned her head to connect our lips.

When I pulled away her crystal blue eyes stared back into mine. Even with my dick buried in her ass she still looked fantastic. Her face was flushed but her smile spread wide revealing her teeth which were as bright as a full moon. As I begun to pull away her mouth draped slightly open and her eyes fluttering as her eyes rolled back.

I whispered to her, "You're fucking perfect."

"You can go harder."

With that I pulled back and began going in and out of her ass. After a few slow movements of just a few inches back an forth I began to take more out and slam it back in with more speed, all the while pulling her hair back as much as she would allow. She began to slip until she nearly fell down sliding onto one arm so she was supporting herself by her elbow. I watched as she took her other hand and made its way between her legs.

Jane was moaning, her fingers strumming her clit as I railed in and out of her tight pert ass. I could feel that familiar stirring in my balls.

"Fuck you're a good whore," I grunted into her as I buried my cock in her ass.

"I'm your fucking whore. I'm your good fucking whore!"

My balls stirred and I knew I couldn't hold it much longer.

"I'm going to... I'm going... fuck... I'm gonna cum!"

Jane surprised me shouting that out ahead of my release.

I roared back, "Do it! Do it, slut."

I felt her ass clench as her orgasm took over. She was drooling as I buried myself into her one last time. Her ass constricted around my stiff cock and I felt her begin to try and milk me for every last drop. It worked. There wasn't much left after dropping numerous loads already but I let her ass work me. Her pussy dripped as I pumped my final load into her ass. Her legs shook without control. She began to fall to the ground causing my dick to slide out, Jane finally made to the ground where she landed on her knees, ass pointed in the air.

It was a sight to behold. Her asshole gaping and cum dripping out of her quivering pussy, her asscheeks bright red and her darker red hair now a mess. I fell to the ground next to her and my face lined up with hers. She looked over and laughed. She stretched her body alongside mine and wrapped an arm around my waist. Lying on her stomach she raised her head up to kiss me on the lips.

"I think you should go home, at this rate we'll never stop fucking," she said to me. Looking at my watch I was shocked to see it was six a.m. I was exhausted.

"That's probably a good idea, the fucking sounds like a good idea too," as I said this I reached my hand between her legs to get a raise out of her.

"Go home. I need a rest."

I got the message and as I stood up I slapped her ass, thanking her for the memorable night. Sweeping up my clothes I closed her door behind me and headed across the hall. I barely hit the sheets before passing out. My dreams that night were a mixture of Jane and Victoria, my favorite when Victoria held Jane's hair back as she helped me face fuck her.

Sweet dreams indeed.