Virgin Babysitter Becomes My Slut Ch. 04

Annie sat on her knees, her round, plump teenage tits held high and firm above the little black dress that I had scrunched into a ring around her waist. Her lip quivered as she took in the scent of the soft cock at the tip of her nose, fresh with the scent of her newly deflowered cunt and my seed.

Everything up till now she had expected in one form or another. She had expected to suck my cock and swallow my cum. She had hoped that I would munch her to a blissful orgasm, and she had naturally been weary of the first fuck I had promised her. What she hadn't expected was this: to have to taste her own fluids.

I had been clear about what I now expected of her. Her getting fucked for the first time was fine, every girl went through it at some point, right? But this was the first true test of her submission. Had her acceptance, her promises, her blowjob-signed contract meant anything? Could she truly submit to my will, forgoing her own sense of decency and humility?

As I watched her struggle with her indecision, I remembered the last time I'd been down this road.

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Callie looked back at me with angry eyes. Her beach blond hair hung oose around her shoulders as she held herself on all fours. I ran my hands down her spine and back up again, idly hoping it would relax the tension from the situation.

"You want to what?" She asked incredulously.

I held the tip of my cock still within her soaked cunt, hoping with alll that I had that this hadn't quickly become the last time I'd feel it's pleasure. What the hell had I been thinking?

Callie was the hottest girl on campus and she liked to fuck as much as I did. Here on a volleyball scholarship, she was fit, flexible and down for anything - or so I thought. Any position had been open to us. Morning wood satisfied by a throat-swallowing blowjob every morning she stayed over. Handjobs under the desk in the library during study breaks or shared classes. Nudes, videos, photos of her making out with other girls on nights out - I was a lucky shit and I knew it, so why the fuck did I have to ask for this? The one thing she said she'd never do.

Fear gripped me and in that one moment I realised that what I feared wasn't losing the best fuck on campus. It wasn't even losing everything I loved about her on one stupid, arrogant request. It was that I actually, in my heart of hearts and deepest soul, loved the woman in front of me and I had just lost her forever. Fuck! I was in love. Genuine, deep, love.

Her question hung in the air, her stare tearing me apart. My brain whirred and buzzed with options. Should I tell her I was joking? Say it was a mistake? Drop to my knees and aologize?

But some deeply stupid part of my brain kicked in before the others and controlled my mouth to say the worst possible option: the truth.

"I'm going to fuck your ass." I surprised even myself with how firmly I said it. It wasn't an answer to her question so much that it was a fact.

She almost spluttered. "No you're not."

"I am," I said firmly. Whchever lobe of my brain that had taken charge really didn't want to give up the reins. "I'm going to fuck you in the ass and you're going to fucking love it."

I gripped her hips firmly just as she began to pull away. I held her in position and started pumping inside her again, nice and slow.

"I love you Callie." What the fuck was wrong with me? What the hell was going on? We didn't talk like this! This is college and we both knew it! We're not forever, we're just having fun. "I love you and I think you love me too." I picked up the pace and her head dropped as she groaned and pushed back on me.

"I know you said you'd never do it, that it's a step too far, that it's dirty; but I know that you're going to love it." With one hand I pushed on her shoulders and with the other I held her hips high, causing her to arch up from the mattress. I raised myself and angled my cock down, aiming to rub against the spasm-inducing rough spot within her cunt. Her moans turned to curses and shudders.

"Your cunt is wet for it, Callie. It knows what I want and it's lubing me up for it, it knows you want it too."

"I don't, I don't," she gasped with her last steady breaths.

I stopped abruptly, pulled my cock from her welcoming pussy and jammed it against her stubborn bleached virgin sphincter. "Yes, you do." Grasping just behind the head, I firmly but slowly pushed into her forbidden hole. She bucked against me and groaned but I held steady and kept pushing. Eventually the outer ring of contracted muscle gave way just enough for my wet cockhead to slip inside.

"There you go Callie, good girl, you're a very good girl," I assured her over her protesting moans. "Your asshole wants me, you know it does. It knows how good I'm going to make you feel. Frig yourself Callie, play with yourself and relax for me. It'll be easier for you."

Despite herself, Callie did snake a hand down to her throbbing clit and began rubbing circles around and over it. Meanwhile, I sank through another round on muscle and the head of my cock disappeared from sight. I grabbed my phone, flipped it open and began snapping, making sure to get the whole view of her gently hourglass-shaped body descending from her raised hips to her tits splayed on the bed with my cock embedded firmly in her tightest, and last virgin, hole.

Angling the phone hinge for the best view, I set my phone to record video and put it on the desk.

Now a couple of inches inside I began to gently pull and push back and forth into her ass. Her muscles relaxed little by little as Callie's fingers worked their magic. Feeling her natural lubricant wearing thin in the tight friction, I dripped saliva onto our conjunction and let my cock work it into her asshole. I couldn't help but grin as I felt her resistance give way and she began taking more and more of me with each thrust. Her shrill screams gave way to lustful moans as eventually I was seesawing half my length into her rear end.

"That's it Cal!" I said as I swatted her pretty hard on the ass. I knew from experience she could take it. "That's it, good girl Cal, good slut. Look at you taking my cock in your ass. I'm filming this Cal, I'm filming your first time taking a cock in your ass." She wouldn't mind. Our slow fuck days had been filled with her sucking me dry while we watched our own videos. All her idea.

Suddenly, Callie let loose a wild, long, primal moan and began to spasm around my cock. Bucking as she peaked, I took advantage of her body going limp to hold the base of my cock firmly and sink myself all the way in her with all my body mass. As soon as I bottomed out I felt that tickling at the very tip of my cock that warns of an upcomin eruption and, to make the most of it, took a few thrusts halfway out of her ass, driving forcefully back in all the way before finally collapsing all the way onto her and unleashing my load deep within her bowels.

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Alright, so it wasn't exactly the same scenario, but as I looked down at Annie and awaited her decision I was struck by that same fear of making a mistake and losing somebody dear to me.

Callie had loved it. As soon as we'd both come down from our highs we'd kissed and torn into each other in brand new passion. In all our previous sexual adventures she had been the one to lead, but from that day I took charge. I didn't wait to she what she offered, instead I took point and sought out what I wanted. I wasn't selfish about it, of course. I loved her and wanted her to enjoy our fucking as much as I did, but we learned over time that she got off on being submissive to me. She lived for a feeling of happiness and completeness she only got when we were together and the excitement she felt when I pushed her boundaries in new ways.

Movement shook me out of my memories. Having finally made her mind up, Annie ever so slowly opened her mouth and extended her tongue.

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This was a little interlude just for kicks. Let me know if you want to read more of Callie's adventures too!