Virgin Babysitter Becomes My Slut Ch. 01

I backed out of that folder and showed her the list. "If there's anything you're curious about you can probably find it here. I'd suggest watching a few blowjob videos so you can see how others do it. Some of these are real porn, so they are more exaggerated than real life, but most of the videos are of amateur girls just like you."

She braved a question. "Is that your wife?"

I chuckled and opened Callie's folder. Rows of videos appeared. My favourites were titled while others just had dates. My wife had always been a firecracker and she'd only gotten bolder and more experimental over time. By the time she passed away we'd done practically everything a man could want. We'd learned so much about each other. It was in college together that her naturally submissive and my dominant natures had emerged, and we'd enjoyed a healthy sex life for our entire marriage.

I looked down at Annie. Her attention was fixed in the thumbnails and I let my eyes wander down the opening of her top and her teen tits. God, I wanted to squeeze them and suck on her pert little nipples. I calmed myself and remembered the time. I flicked off the TV and handed her the remote. "Once the boys are in bed, feel free to take a look."

-----

Dinner turned out to be a pretty dull affair. I'd been tasked with wining and dining a new investor and while I usually get some joy out of it, we just weren't clicking. Mind you, my thoughts were on the virgin babysitter in my home probably watching my porn collection by now.

Once dessert was ordered my horny curiosity got the better of me and I excused myself for the restroom. I took a stall and opened my home security app. The first thing I saw was little virgin Annie sitting on my couch with her feet up and knees spread. On the TV was a college video, one of our first, of Callie sucking my cock in the shower. She was on her knees slowly sucking. I knew what came next. College me wrapped his hands in Callie's hair and started fucking her face. I was relentless, and I remember how much Callie got off on it. I also remembered well how the video ends and wondered what innocent little Annie would think.

I switched angle to see Annie face-on, and she had one hand gingerly touching her slit over her panties and tights. I watched for a few minutes as she gently stroked herself without any practise or rhythm and was gutted that I had to go back to my dull dinner meeting.

An hour or so later I pulled up to a wooded spot a few minutes from my house. I opened the app again and saw Annie watching normal TV. I scrolled back through the footage until I reached the part on the Callie video where I came all over her face. I'd destroyed her that day. Mascara leaked from her bloodshot eyes, her throat was raw and spit coated her mouth, chin and my cock. I played the video and watched Annie's reaction as I pulled out of Callie's throat and came all over her face, adding white pearls to the mess. In the meantime Annie looked completely flustered, her white cotton panties showing an obvious dark patch that her fingers furiously rubbed.

The video didn't end there however. While Annie was basking in her first feelings of fun frustration, video me kept his cock aimed at his then-girlfriend's face. Callie was visibly surprised when my piss erupted and spluttered over her lips. It was only a single squirt, but Callie had looked into my eyes with a face I remembered very well. She smiled like a Cheshire cat then opened her mouth. Taking up the invitation, I remember letting go and releasing my stream onto her waiting tongue.

That had been the first of many times we'd experiment with that. God I missed her.

Caught up in my memories, I hadn't even noticed that Annie was stroking herself ever faster. It looked like she was about to reach the cusp of release when she stopped. What was that about? Had one of the boys woken up? Her hand dashed for the remote and turned the TV off. She looked from side to side as if panicking, then slowly she looked up and directly into the camera I was viewing.

Despite the fact that there was nearly an hour's time delay between video Annie and restaurant me, we seemed to be having a silent conversation. "Oh my god, I can't believe I did that when you could see," she would say. She'd be shocked. Appalled! Embarrassed! I would only encourage her to carry on.

I skipped ahead to the live feed. She was currently watching some basic romcom.

Deciding it was time to head in, I got going.

-----

I waited an extra breath before I opened the living room door. With fresh images of her indecency in my mind I was already half hard, the blood pounding through me. A small part of me screamed "my god, what are you thinking?" but the heat in my blood patted the sentiment away.

As I stepped in, Annie sat up cosily on the couch. If I hadn't seen what she had been up to I might never have suspected, except the air was thick with foreboding and, though I may have imagined it, the slight sweet smell of wet virgin pussy. She looked up at me with doe eyes. Her mousey face and hair was so fucking cute. Her nose and cheeks were red with blush which offset her otherwise pale face. Her tiny mouth and red lips had a small natural pout, and she sat with her knees at her chest and her arms wrapped around them.

When she'd arrived I'd purposely avoiding looking at her, but now, full of testosterone, I couldn't help but follow the black tights up from her feet, over the knees and to her buttocks exposed beneath her tiny shorts. The tights turned pale as they stretched and thinned over her butt cheeks. Above her shorts she wore a simple white top, her chest hidden by her knees and arms.

Those eyes searched mine. I knew the question they were asking. "Did you see me? Did you see what I did?" They nearly cried in shame.

Wordlessly I slowly sank down to the floor, my head level with her feet on the couch. I reached to the remote and turned the TV off, then looked up at her and gave her my most reassuring smile. "Yes," I said calmly, answering her silent queries. "I saw what you did." I sniffed deeply. "I smell it too."

She blanched.

"No, it's a wonderful scent. It's the scent of a young woman, that's all." I reached up and gently unwound her arms. I put my hands behind her calves and gently pulled her legs apart on either side of me. Once her feet were settled on the floor, I gently stroked her thighs back and forth with my palms. "There's nothing wrong with what you did. You need to learn it's okay for you to have wants and desires. Callie certainly had them, you saw, and we made each other happy for many years." At mention of my wife, Annie looked up at the blank TV. It must've felt wrong to her, but I knew Callie wouldn't mind. If she were alive today she might even be on the couch with us egging young Annie on.

With each stroke I moved my hands closer to her the hem of her shorts and a little deeper into the warmth between her thighs. Her breathing quickened at my touch. "I love your outfit tonight Annie. Did you choose those shorts so I would notice?" She didn't reply, instead her eyes were closed and her head was tilted back, her body rippling in the sensations running up her loins.

Eventually I took my strokes took the tips of my fingers inside the hem of her shorts. The thick denim lining was warm from the heat of her core. I kept stroking her inner thigh with one hand but with the other I changed it to hold still on the inside of her leg and run my thumb firmly up and down the seam of her shorts, directly over her moistening slit. Her breathing sped up and deepened in response and her hips began to rock back and forth against my furtive digit.

As she began the rise to a climax and I got into it, she put her hands to mine and tried to push me away. "Stop, stop please."

I resisted and held tightly to her leg and pushed deeper into the seam. "Why? You're getting so close."

"No, no," she moaned. "I'm going to pee!"

My god, I thought. She doesn't even know what an orgasm is!

I took both her hands in mine and pushed them away. I reached under her butt and pulled her close to me then reached into the hem of her tights and shorts and pulled them swiftly off, throwing them aside. I breathed in her secret scent through her plain white panties, pulled the crotch aside and buried my tongue in her wetness. With my tongue lubricated I moved my lips to her firm little clit and began working it while gently probing her insides with a firm finger. I sought out and gently rubbed the ridged patch inside, careful to avoid the thin film of her innocence. She bucked and screamed against me, her hands trying their hardest to push my head away, but I kept close and pushed onwards. I added a second finger and rubbed harder. Her breaths got shorter, her resistance waned and she bucked and moaned as she reached her first ever climax.

I slowed my ministrations but didn't stop outright, riding her descent back down to normality. Once her breathing settled into long laboured breaths I pulled out my fingers and kissed her button au revoir before pulling back. While she tried to recover I used the opportunity to subtly check on my phone that the kids hadn't wandered out of their rooms.

Satisfied, I got up and settled in the couch next to Annie. I pulled her in close and cuddled her in the crook of my arm. It was a few more minutes before she opened her eyes and came back to reality, and she seemed to have no idea how to react. "How do you feel?" I asked, enjoying the taste of her on my tongue.

She struggled to find words. Eventually she mumbled something like "we shouldn't have done that." A few seconds passed as I pulled back and gave her a stern look. "Sir," she finally finished.

'We', not 'you'? That seemed to imply she didn't feel like I'd forced it on her.

"Has Dylan ever done that for you?" I already knew the answer of course, but that wasn't the point.

"No," she mumbled awkwardly.

"Don't you wish he would?" She was silent. "Dylan is a boy, and a selfish one at that." I started stroking her back. "If you want to learn how good your body can feel, you only need to ask."

She pulled a little away from me and looked up into my eyes. "Don't you... don't you want me... to do anything?" Her hand timidly snaked it's way to my clothed cock.

"Of course I want you. But," I nodded to the TV. "You've seen what kind of man I am with my women. I'm not one for being gentle. If we start down this path together, I won't take no for an answer from you. You'll be mine, just like you saw Callie was." She released me and looked suddenly sullen.

"I... I don't know what to do... Sir."

God her deference was driving me crazy. Every time she remembered to title me properly she blushed further.

I tipped her chin up and kissed her. She was initially hesitant but opened up hungrily when my tongue pushed it's way between her lips and teeth. She grasped at me hungrily, apparently not bothered by where my mouth had been and I pulled her tightly to me.

My mind buzzed, trying to decipher her needs. She was an active participant when I pushed her but her barriers needed breaking. I decided to push her further and judge her reaction.

I lifted my butt off the couch and, breaking our kiss, shuffled my pants to the floor. I took her right hand and pushed it inside my boxer shorts and wrapped it around my hardness. She shuffled herself down the the floor and pulled the hem of my boxers below my balls. She kissed the tip and took it inside her lips, exactly as she had done with Dylan. The soft pouty pillows felt nice, but she desperately needed to learn how to really suck a cock.

I reached down and wrapped my hands around her tiny waist, then lifted her up onto the couch, her mouth pivoting on my cock. I kept her hunched, her naked ass sat on her feet and her clothed torso leaning over to tend to the meat in her mouth.

"How did you learn to suck cock?" I asked.

She balked a little at my crude language, lifted her mouth off and said shyly "Dylan, sir."

I put my left hand on the back of her head and pushed her down. I rested my other hand on her upturned ass, groping firmly at her cheeks and my little finger dipping into her wetness.

"Dylan has no idea how to treat a woman, how to train one." I turned on the TV and switched back to the video of myself and Callie she'd been watching. I scrubbed back to the beginning to Callie's head in my crotch and my cock in her throat and let it play silently. I saw Annie's eyes dart to the TV. "I know the kind of woman you are, Annie. I know what you need, what gets you off. You need a man to show you who you really are, not some tiny dicked teenager."

I pushed her head towards the TV. "Do you want to learn how to do that? That's how you make a man cum." Annie hummed hungrily on my cock and her back flexed in desire. I decided to take a gamble. "It's not easy, only true sluts can do it." She moaned again. "If you want to please me, if you want to make me very happy, I can teach you to do this just like taught I her." On-screen, young me released his hands from Callie's head and she shot up from my cock smiling and dripping with spit and saliva. Annie, for the first time, pushed herself down onto my cock.

It was only a few centimeters before she gagged, but it proved to me the desire was there. The next time she descended I strengthened my grip and held her in place while strumming in small circles around her clit. I didn't push her down further, depth would come later, but I wanted to build up endurance. She coughed and spluttered but I kept her in place for a few seconds before pulling her up by the roots of her hair. "Is this what you want? You like being treated like a slut?"

She nodded, saliva drooling from her red lips while her nether lips coated my fingers.

"Tell me! Say it. Tell you you're a little slut."

She nodded. "Yes, yes sir, yes I'm a little slut," she replied breathlessly. I pushed her back down, her tongue slid down my shaft and her lips shut tight around it. I took control and pulled her head up and down slowly. She coughed and resisted lightly but, to her credit, held fast as I very slowly and gently fucked her face.

I took up the TV remote with my free hand and switched to the live camera in the nearby corner of the room. Annie's cute naked ass was up in the air and her head dipped up and down in my lap.

"Look at you, little teen whore. Cock in your mouth, bare ass in the air." I dropped the remote and slapped her ass cheek hard. "I bet that got you wetter, didn't it? I bet you like being spanked while watching yourself swallow a real man's cock." I dipped my fingers back into her slit and rubbed firmly just inside her soaked lips. "I was right, you are a little whore, aren't you? I always knew you would be." I slapped her ass some more, the red handprints showing up nicely on her alabaster skin.

By this point I was about ready to pop. Nothing, nothing at all beats the feel of a passionate woman doing her best to swallow your shaft. But when I came I wanted to see her play with it. "On the floor," I ordered, and she shuffled off the couch and between my feet without my cock leaving her lips. She looked up at me as she sucked.

"You're doing amazingly, I'm very, very proud of my cute little slut." Her adorable face blushed. Her mascara had flaked and run from her eyes and her lips were red with passion and wet with saliva. "I'm going to fuck your mouth now and cum on your tongue. When I do, I want you to hold it in and don't spit or swallow. Understood?"

She nodded as best she could. I reached down and pulled her top up over her head, forcing her to relinquish my cock for a second but she quickly dived back on as I got my first real look at her perky tits. They were creamy white, held high and perky on her chest and topped with the cutest pink nipples. I pulled and squeezed each one in turn and she was deliciously responsive. I gripped the right one between thumb and forefinger and twisted it gradually harder. She moaned long and deeply around my cock and I smiled broadly.

I grabbed her head again and started forcing her mouth up and down, using her lips as a cocksleeve for my own masturbation as her teen nipples rubbed on my knees. She could take half of me now, but I knew taking the full thing would come later. I felt the cum rise and my balls tighten, then pulled her down as far as I could and released my load, shot by shot, into her throat, pulling out slowly to then coat her tongue.

She coughed, bucking against my grip, cum spluttering out of her nose and lips. "Suck it all out," I said gently. "Nice and easy." I was overly sensitive, but her tongue was soft and helped to sooth my softening shaft. "Remember, no spitting, no swallowing."

As I slid back on the couch removing my cock from her mouth, she relaxed back on her haunches and looked up at me. Her big doe eyes were red and swollen with tears, begging me for something. Cum dribbled from both nostrils and the corners of her lips as she tried to catch her breath without letting more of my seed escape.

I took my phone out of my pants and aimed the camera at her and started recording. Fear gripped her eyes and she turned away. I grasped her saliva slicked chin and turned her head back. "That's no way for a young slut to behave," I said sternly. "If your master wants photos of you, you don't turn away." She looked shy, trying desperately to avoid the gaze of the lens. "You're a slut now, my slut, Annie, and when I point a camera at you I want you to look deeply into the lens and smile.

She struggled but eventually I saw her gaze fill the screen nicely and she smiled an awkward, nervous grin as she tried to keep her mouth shut and the sperm inside contained.

"Good girl. Now open," I said firmly.

Sweet little Annie tilted her head back to ensure nothing escaped then carefully opened her mouth. My seed was swimming over the surface of her tongue, a viscous white milk that was in some spots globular and others a thin translucent liquid. Leaning forward, I took ahold of the top of her head with one hand and pulled it forward, just enough that some of my deposit slipped out the corners of her lips and dripped down over those milky white tits.

Making sure I got her glazed tits in frame, I then let go of her and sat back. "You may now swallow, my little cum whore."

She closed her mouth and gulped. Her tongue swished around her teeth and gums, finding what remained before swallowing that too.

I glanced at the clock on the wall and grimaced. Noticing, Annie did the same and swore. "I have to get home, mom's going to kill me."

She rummaged around for her clothes and started dressing. I got her a glass of water and a damp cloth and encouraged her to clean her mouth. "Don't worry about your mom, I'll give her a call and explain everything."

She looked at me quizzically.

I laughed. "Not the truth, I'll tell her I was running late and you agreed to stay longer to help me out."

She finished putting on her oversized sweater and I stopped her at the living room door. With one hand on her hip, I moved a lock of her bangs from her eye and smiled down at her. "You were incredible." She blushed a deep red and I kissed her deeply. "I hope that was as fun for you as it was for me, and I hope I wasn't too rough with you."

She shook her head gladly. "No, I... I loved it, thank you. I didn't know I could feel... like that."

I smiled. "If you want to, if you feel ready, come stay with me next weekend. Pretend I need you to babysit the whole weekend. Callie's parents are taking the kids for a couple of days, and you and I can spend some real time together, if you want."

She nodded enthusiastically.

I straightened up a little. This was getting a little too cutesy for me and I wanted to maintain control. I wasn't falling for her (was I?), this was just good, awesome, submissive sex. "If you come on Friday, you need to have done two things. One, dump Dylan. I won't have his sloppy seconds. And two, understand that you coming here means I will fuck you." Her smile dropped to something more serious. "It will be rough, you will be debased, used and humiliated. I'm not interested in being cute and cuddly and gentle with you, and I don't think you need that. I think you need a real man to show you what you've been missing and give you what you really need." I darted my hand up inside her sweater and under her bra, grasping her nipple and rubbing the tip. "You will come here a virgin but you will leave a true, well fucked, slut. Do you understand that? The choice is yours."