The Dare

Debra

I was shaking as I did as he told me. I was scared and curious at the same time.

Turning around, I positioned myself over his cock and let it slide down into my very wet pussy with a hiss of breath as he entered and filled me.

Balancing my hands against his chest, I moved up and down his cock, shivering at the feeling of him inside of me and at the knowledge of what would come next.

When I could hear the wet slap of our bodies coming together, I knew that his cock was wet and ready and I plunged down on it one more time before lifting my hips and moving forward just a fraction.

Poising my asshole over his cock, I looked into his eyes, gathering courage as I lowered myself down. My eyes closed as I pressed down on the soft head, felt the shaft give ever so slightly as I pressed on it, then respond with pressure there. I could feel small jolts of pain as the muscles resisted, were pushed against and finally gave, allowing the tip to enter slightly.

I bit my lip. The pain was there but not as bad as I feared. Pressing my hips down a bit more, I pushed until I felt the whole head enter. With a moan, I stopped for a moment, panting, my eyes watering as I tried to adjust. A moment of panic swept through me and I thought of just pulling off and insisting he fuck my pussy instead. My eyes met his once again and, instead, I rose up a bit, but not enough to dislodge him, and then pressed down, groaning at the feeling of his cock opening my asshole little by little.

I continued to work it in, my muscles there slowly relaxing and ltting him in. Tears stung my eyes from the unfamiliar sting of the pain but I didn't give up. Up and down I worked my hips, taking him into me more and more until, with a sigh, I felt ass come flush with his skin.

Taking a shuddering breath, I paused, a shiver running down my spine as I lifted my head and looked into his eyes once again.
 
Caleb:

"Look down Debra. Look at my cock stretching your no longer virgin asshole. Look at it as you feel my stiff cock filling your ass and tell me what you're feeling and thinking as you adjust to being my sweet lil ass fuck now and now just a great cocksucker and fuck.
"Look and then tell me Debra," he says quietly as his thumb and finger pinch and roll her clit, slide up and down on it like he's jacking off a little cock.
 
Debra

OOC: LOL Didn't even realize I broke a thousand posts. *grins* Hows that for being attentive?

IC: I shuddered again but did as he said and looked to where our bodies were joined. I panted and moaned as his fingers played with my clit and could feel myself getting even wetter.

"I...I...ohhhh...I feel so full and...and it doesn't hurt as much as I thought. I..." I blushed and stammered a bit,"I feel...kind of...slutty and...and....ahhhhh...it feels good, it really does but I..." The blush suffused my body,"Oh, Caleb, I feel just like a wanton slut but I'm enjoying it!"
 
Caleb:

"Like being ass fucked Deb?
"You are slutty, your my slut... aren't you Deb? You love all we've done and all I'll do to you and have you do and you don't want to miss any of it do you my sexy Debraslut, my own personal little slut and fuck whore.
"That's what you are and want to be isn't it Debra? Be honest with yourself, " he says as he keeps 'jacking off' her clit and he tightens his pelvic and ass muscles to swell and grow a bit in her ass.
 
Debra

"Ahhhh....ohhhhh...." I couldn't speak as he flexed his cock in my ass, the unusual feeling of being so full back there and the tremors he was causing with his fingers on my clit wouldn't let me think, much less talk.

What was he saying about being his slut? A shudder wracked through me and I moaned out loud. A thousand questions entered my head and left it as another wave of passion and lust coursed through me.

"I...I...Ahhhh...Caleb! We...we just meeettt...oh God..." I tried to tell him all the reasons that we couldn't keep up like this, that it wouldn't be good to look at being together in any kind of rleationship but the feel of his fingers and cock wouldn't let me concentrate.

"Oh God! Oh God! Caleb...please fuck me...please...just fuck me...I don't want to think about the future...just here and now, with you...."
 
Caleb:

"So we just met.. you're mine. You've been mine since I found you in here and since we fucked each other last night.
"Now my cock's deep up your sweet slutty ass and that makes you all the more mine.
"Right Debra my slut.
"You want this all of the time and we know it. The only way is being my slut, my little Debra whore.
"You are, you want to be and you will be, won't you Deb? Mine, my slutty little fucktoy right?" he says and asks as he strokes her clit harder as it's pinched more tightly.
 
Debra

I shuddered and shook as he pinched my clit. I wanted him to fuck me so badly that I was ready to agree to anything. Right at that moment it didn't seem so far tetched to think of being with him from now on, to be exactly what he had named me, his slut and whore, his fucktoy. Even the names that he called me sent a thrill of desire through me.

Hanging my head, I nodded,"Yes, yes," I moaned, moving my hips so that his cock moved in my ass,"Yes, I want all of that...I want to be with you, to be yours, to fuck you all the time."

I moaned and whimpered at the need I felt,"Please...please fuck me now, Caleb....please."
 
Caleb:

"Hands and knees like the hot bitch you are and spread you pussy open for me and I'll fuck you like the bitch you'll always be for me."
 
Debra

My eyes flickered and I looked at him again. The possession I saw in his eyes sent a shiver through me but not of fear. Somehow that feeling of being possessed by this man seemed right. Seemed good. Was I going crazy?

I didn't have the answer to that question but I did know that I wanted to be fucked by him in every way imaginable and so I lifted my body from his, sighing in disappointment as his cock slid out of my ass, and bent over on the bed, laying my head down on the matress which put my ass up in the air, ready for his cock.

Reaching beneath me, I spread my pussy lips with my hands, opening it to him to take whatever pleasure he would from it.
 
Caleb:

His cock drives as deeply into her as he'd been last night and three of his fingers were pushed to the last knuckle into her ass at the same time.

Then he fucks both holes at the same time with cock and fingers as she howls and screams, as she babbles out what she is and what she's feeling as he fucks and fucks her with unbridled lust and need.
 
Debra

A whoosh of air escaped me as his cock drove into me hard and fast. I moaned in abandon as his fingers filled my other hole and I whimpered as he began to fuck me with rapid strokes.

"Oh God! Oh yesss...ohhhhh..." I couldn't stop the flow of words,"Yesss, Caleb, yess...fuck me...fuck me like a whore...a slut...ughhh...yesss...that's it...oh, yes...I want you to fuck me so hard. You feel so damn...ahhh...good..."

His thrusts drove me into the bed once again, only this time it wasn't on my back and so my voice was muffled by the covers and mattress until I moved my hands from my pussy and propped myself up on my elbows, keeping my face down so that he had full access to my pussy and ass.

"Oh, yes...oh God...harder...please...harder, Caleb.." I was whimpering and moaning like a slut in heat and I didn't care. "Feels sooo damn good...having your...ugh...cock in me...feeling your fingers in my ass..."

I writhed around on the bed but not enough to dislodge him, I didn't want to do that. The feel of his cock deep in me, hitting my barrier high inside of me that was still sore from last night's fucking drove me crazy and I pushed back to try and take him in as far as I had last night.

"Unggghhh..." I grunted as I pushed backward, feeling him push against it, sending slivers of pain/pleasure through me,"Harder..harder..dammit...I need you to fuck me deeper!" I was acting like a slut and the feeling was liberating, wonderful, addictive....I had to have all of this man, and I had to have it now.
 
Caleb:

His hands fold her legs to her belly and he rotates her on his cock so she's on her back again. His hands move her legs so that they stick straight up along his chest feet in the air.

He can't use his fingers in her ass now, but spreading her legs as widely as they'll go and pushing them back to roll her ass up he can go as deeply as last night.. and with one ram of his cock into and onto her he's passed that deep barrier once again and is fucking her womb and cunt all at the same time.

Unlike last night he doesn't take short strokes to stay deep, deep into her but pulls all the way out and rams back into and beyond again and again, breaking her in and breaking her other than physically for nothing is more addictive than intense orgasms, absolutely nothing.
 
Debra

"Ahhhhh!" I could hear my own screams of ecstacy as he moved to fuck me into my belly on the first hard stroke. Then he pulled out until he was barely inside of me and took me hard and completely yet again.

"OH GOD!" I cried out as he fucked me mercilessly, his cock using my pussy, my tunnel, my womb for his own pleasure and mine,"God! Yesss...ugh...yess..Caleb...yessss...fuck me...fuck me like a whore, like your hot bitch...oh god, yesss..." I pushed up to meet his strokes the best I could in the position he had put me in.

"Oh, no, oh God, I'm not going to last," I moaned as I felt the orgasm that had been sweetly building begin to encompass me,"I...I'm...ugh..oh God, no...I don't want to stop this...I...ahhhh...don't want to cummmmm yet...ohhhhh..."

I could feel the waves break over me, I was on the edge, my body wanted release and I wanted to continue for as long as possible..I didn't want this to end.

"Oh, Caleb, I'm going to cum...going to cum so hard as you fuck me like thisssss..." The words tumbling out of my mouth were so dirty and naughty that they spurred my approaching orgasm. I should have been embarrassed at them but all I could think about was the cock ramming in and out of me and the relief I would have when it happened.
 
Caleb:

He was sweating and panting as he took her, as he fucked her as hard and deeply as he could, "Cummmmm my slut Deb... Cummm and keep cumming until I do.
"Not close yet so you'll be fucked for awhile yet my whore fucktoy."

His prick keeps pulling back, nearly out then it's driven, rammed back again as he hooks her legs with his arms so he can also giver her tits play and her nipples pleasure to add to all she's feeling already.
 
Debra

As his fingers brushed across my nipples, I jerked and thrust up my hips. That was all I could take and I gave into the orgasm that he had been nursinf for so long now.

With a sigh that was part groan, I shuddered and tightened against him, my pussy clutching his cock as it spasmed around it, clinging to it and causing more friction than I had been feeling already.

Helpless, I trembled as my juices flowed all over and around him, wetting both of us and causing a wet slapping to be heard as he continued to pound into me.

The orgasm seemed to go on forever as I was pressed again and again into the bed. Finally, it subsided to a low roar, not completly going away as his cock was still working inside by pussy.

"Ahhhh," I moaned as the pleasure was kept on edge by his thrusting inside of me. I whimpered out at the feeling of release but not total release and shook my head in my constant need.

"Please, Caleb, please," I said hoarsly as the pleasure began to build again,"I don't know how much more I can take."

The truth was, I had never been kept in this kind of constant arrousal and I felt as if my flesh was sensitive to the very air moving around us. The feeling was euphoric and, yet, a bit scary as well.
 
Caleb:

"How," he pants, "about like this my nasty lil cum slut?" And his cock is suddenly out of her still spasming cunt and back once more into her ass and he starts fucking it just as he'd just been fucking her cunt. Long full hard strokes from head to it's base over and over as her tits are squeezed and twisted so pleasure as well as the pain of his reentry floods her system and body.
 
Debra

I whimpered as I felt the abandonment of my pussy and then cried out as he filled my ass. Breathing hard from my last orgasm, my pussy tingling and spasming still, my ass cheeks clenched around his cock, I still couldn't stop the dersire that was filling me again.

I groaned loud and deep as my body was literally punished with his cock. I felt almost like a rag doll, tossed about in the winds. She could only lay panting as his cock pistoned in and out of me, whimpering and moaning as I felt my juices spill and cool on my heated body.

"Oh God," I moaned to him,"Ohhhhh....God! It feels so good but...ahhhhh...You're going to make me cum again...cum with me...cum in my ass...take me there and make me yours again.."
 
Caleb:

"Are you mine?
"Will you live here with me Debra?
"Can you get what we give each other if you don't?" he asks as he rams and pounds into her ass and belly while playing with her tits and nipples.
 
Debra

I groaned. I couldn't think straight, didn't want to. All I knew was I didn't want to miss this, to leave this. All thoughts of how illogical it was to be with and live with a man I had just met fled my mind as I bucked back against him, wanting only to feel my orgasm wash over me again.

"Ohhhhh..." I moaned out, trying to form sentences,"I...ahhhh...yes, yes, I'll live here with you...God, yes...no, I can't get this anywhere else and I...don't want to...ssssstopppp...Oh, God!...." And I was shaking once again as the pleasure overtook me, shuddering through me as he continued his sweet pounding in my ass.
 
Caleb:

"Then CUMMMMMM slut. CUMMMM for me lovely and sexy Debra my whore. CUMMMM NOWWWWW!!!" he hollers as his cock is rammed beyond her cervix one last time and he fucks her womb with those short fast strokes until his seed fills her to overflowing once more as he cums in and with her as she screams and babbles.
 
Debra

I saw stars. That was the only way to describe how utterly explosive my orgasm was. He was out of my ass and into my hot, wet pussy in a matter of moments. And then he was fucking me so deep I couldn't keep the cries from coming.

I don't know what I said, didn't care, all I knew is that this man could make me feel like no man ever had in my life.

I came and I felt like I couldn't breathe. I shuddered, shook and my muscles tightened up, holding onto his cock as it spasmed inside me. Our cum slid from my pussy and onto my thighs, we were both drenched and so was the bed.

I don't know how long I was lost in that orgasm but, when I finally came to my senses, I felt as if I couldn't move. Didn't want to move. A languid peace surrounded me and all I wanted to do was to snuggle up to him and fall back to sleep.

Looking up at him, his face bathed in sweat, I laughed in a tired voice. "How about a time out for a nap? And then I can make you breakfast. Or lunch. Or brunch...whatever meal happens to coincide with us waking up."
 
Caleb:

"Keep fucking me like that and I'll happily die of starvation my sexy lil Debra," he chuckles as he hugs her then kisses her long and deeply as he presses and grinds on her pussy lips and clit.
 
Debra

I moaned into his kiss and pushed back on him as he ground into me. When the kiss broke, I yawed and then laughed as I covered my mouth.

"If we keep this up I just might fall into a coma!" I said and then pulled him down beside me and wrapped my leg around him as I lay my head on his chest.

"Mmmmm," I murmured as I lay there listening to his heartbeat,"Just a few minutes of sleep and then I'll be ready to get up and fix that meal."
 
Caleb:

"After we've showered together that is my luscious lil Debraslut," he says the smile evident in his voice.

Covers are pulled up, he moves you both to a temporarily dry spot on the bed and you both doze off with one of his hands on her ass and his other around her back cupping a breast.
 
Debra

When I woke next, the sun was streaming fully into the room and I glanced at the clock, startled to see that it was past noon. I turned my head to see Caleb still sleeping beside me and I smiled. Who would have thought last night that I would wake up like this in bed with a total stranger?

Then a thought struck me. The guys and I groaned. They must think I'm dead, attacked by the ghost of Old Man Withers. I wondered if Caleb had his phone connected yet so that I could call them and let them know I was okay and not to come by and try to find my poor mangled body. I figured just about now Sherry would be working them up to a frenzy of guilt and grief and they would come storming in, determined to rescue me or see if they could find my remains.

Just what I needed, the calvery too late and messing things up. I had deliberatly made no mention of them in my confession to keep them out of it. Trust them to come charging in and mess things up and get themselves right into the situation I had tried so hard not to have them in.

Wiggling out from his hold, I slipped out of the bed and tiptoed to the bedroom door and out into the hall to search for a phone to call off the idiot brigade before they made a real mess of things.
 
Back
Top