The Saint and The Sinner?

I chuckled at her question, before I started stroking my long thick dick in and out of her from behind. I had to think about it my many prior sexual escapades a bit; one night a couple years back stood out.

“I had a threesome with two girls one time and they managed to get me off six times that night,” I said, a smile breaking across my face at the memory.

“Think you can do better?” I asked, practically issuing a challenge. I accentuated my words with thrusts deep into her cunt, still holding her wrists bound behind her. My thrusts quickly grew more insistent, as I enjoyed making her ass jiggle with every pump into her!

Oh gosh there he goes again making me nibble on my bottom lip. Of course I thought I could do better or at least match it. I'm only one girl after all. My fingers start to grip my sheets when he drives in harder and in all I think about is how massive of a challenge it would be. I could feel my ass jiggling and added a little extra bounce just for him. My face was now buried deep into the soft fabric of my bed as I wallowed in the fucking he was giving me.

"I'm game if you are" I said finally taking a moment to not drown in sexual pleasure. I bounced my ass even harder, forcing him even deeper inside me. I was determined to make him howl in pleasure and when it becomes too much (and I hoped it will) I'll fuck him even harder!

Every night I had spent fucking myself to thoughts of him led up to this moment. Oh the nasty little naughty things I'd done to him in my mind was going to be lived out tonight. The past two days of our fucking were only an introduction to what I really wanted.

I moan his name and each letter on my tongue sent a shiver down my spine. Being his sexual plaything was what I wanted as well as motivation enough to cum but I had to pace myself too. I start to tighten my pussy in an effort to hold out as long as I could. Fuck, it was I could hear just how wet my pussy was, hearing pumping in and out of my wet little hole and knew my body would be his for as long as he wanted.

Her wetness flooded my cock as I pounded her relentlessly. Her words drove me on, promising a long night of sexual bliss.

“I’m game,” I replied, my breathing heavy. I smirked to myself as I railed into her from behind, still holding her prone, making sure she knew she was mine.

“Do my orgasms this morning and… afternoon… count towards our goal?” I asked, driving my cock terribly deep into her and holding it inside firmly. I gave her butt a solid spank, and a hard squeeze, my body shifting to push even further inside her, my dick throbbing mightily within her...

"Fuck you're in so deep" I screamed out loud now wishing he hadn't had my wrists bound. I wanted to claw at the sheets like I had before. His question about earlier was a great one. "I don't know if you want to count the morning's orgasm" I moaned out trying to adjust my hips and change how he impaled me.

"I'm not counting Kelsey, ...Fuck!" I screamed realizing I couldn't change my position and that he was going to make me cum again. I could feel myself letting go and drenching him. At this rate I'm worried that I'm going to burn out before he does. My thigh cramps so hard that I know I'm going to feel this tomorrow and yet I keep cumming. I didn't want to work out my kink out it was a badge of a great sexual experience and I wanted that. My mind went back to this morning and how he mentioned something about viagra. I had never done anything other than the occasional joint and ecstasy pill. Drugs was another area where he had me beat hands down. As I continued to cum and feel myself wanting to ask for a time out I decided to ask about viagra.

"You mentioned something about viagra in your book bag earlier?" I could barely catch my breath as finished cumming.

I held my cock deep inside her as she came all over me, her body convulsing in ecstatic pleasure, her cunt spasming all around me, milking my cock and bringing myself to the edge. She was talking, but I couldn’t hear her as I started thrusting into her hard. I let go of the belt around her wrists, letting them free, only to reach forward and grab her hair at the back of her head and push her face down onto the pillow as I ravaged her.

I pumped hard into her, again and again, chasing my orgasm until it finally burst free, my balls clenching up and my cock spurting forth a geyser of my cum into her pussy. I growled and groaned through it all, humping her plump ass with abandon until finally it subsided.

I pulled out of her, taking my time, until my cock plopped free, releasing my copious seed from within her depths to pour down her quivering thighs, and I let go of her completely, standing at the foot of the bed behind her.

I smirked as I admired my handiwork. “Well, let’s just call this number one for the night,” I said, giving her ass a playful swat!

I wanted to say no to say don't but it again I got lost in it all and let him give me a full dose of cum. I froze for a minute enjoying the sin of it all. His cum slowly coating my insides as lied there smiling. Now probably wasn't the best time to tell him but I could make jokes about it. "You know this is how girls get pregnant" I joked and smacked his ass. I watched him moving a bit before sitting up to look at him.

Oddly enough I wasn't to worried about the consequences of tonight. I guess if it had been anyone else I'd be nervous. Something about him had always made me calm.

Now, I was curious though. I wondered how he lasted so long during this infamous six orgasm night. Viagra again popped into my head. I could recall if I'd asked him already or if just imagined it. By now my pussy was on fire with sensations. Part of me had wanted to go again just then. Another part of me was way too sensitive to even think about being fucked again. I contemplated my ability to last the night out along with my barely register-able drug experience. Viagra would be the third thing I've tried.

Her comment about getting girls pregnant was definitely something I should have considered, but watching my cum ooze out of her cunt was just too damn hot.

My phone was still filming on the dresser. I grabbed it and turned it off, quite happy with the footage I had acquired. "I think I've said this before, but we could make some good money selling videos like this..." I said with a smirk. I nodded towards the still-playing computer on her bed, the camgirl putting on a teasing show. "And with tits like what you've got... You'll have a lot of customers."

"Ha" I said giving a chuckle. "You're probably right about that".

I watched my screen liking the cam girl over as I did. Something in that moment clicked. Maybe it was the pressure of becoming Kevin's exclusive mouth for hire or the rush of empowerment I felt when I looked at his sex drunk face but asked "Why Not?". I waited for his reaction to my answer. " I'm game with a little help from you of course ".

I got cleaned up a little and rejoined him on the bed. I couldn't help but wonder about his experience in this kind of thing. Had he any experience?

I raised an eyebrow as she agreed to give it a go, with a bit of help from me. I smirked. I had a little bit of experience in this particular field.

"Well, we already have a bit of footage," I said. "But we're gonna need to make a lot more." I winked at her deviously.

"And I think your little challenge tonight would be the perfect opportunity to create it." I rolled onto my side, facing her, both of us naked. My long thick dick lay on her sheets between us, still glistening with her juices and my cum. "We can figure out the rest in the morning..."

I looked down and playfully raised my eyebrows. Looking him in his eye I responded "Good idea. Except one little flaw." I smirked. "I might loose count so..." My hand went for the semi swollen cock lying against my pelvis. "I hope you were keeping count.".

My hand lazily stroked him as we lied there. My nipples stood out like push pins in cooling air of my room. "You made me cum so much" I moan inches away from his lips, my hand now more intent with its stroking. "It's hard focus with this fucking me." My eyes were sincere and innocent yet naughty.

"Besides the dare was more a bonus than a main goal. You still complete the mission". I joke as my hand moves down to his balls. The idea of spending the entire day christening every inch of my apartment with my new fuck toy roommate was too good to be true.

I rolled over showing my plump ass to him. Mostly I just wanted to feel him nestled there between my cheeks. My hips raised slowly stroking his long, thick, dick between them. I bit my lip imagining him using my ass to jerk himself off. His thick hands grabbing and squeezing would put me over the edge.