Waiting for the next weekend was torture. Sunday I’d been easily distracted. After clearing up Annie and I’s little tryst from the night by before, my kids kept me active enough that I mostly didn’t think about cute the little Babysitter and her perfect perky tits or the enclosed feeling of my cockhead squeezing into her throat – until the evening that is, when I finally collapsed into bed. Monday, however, was a different matter.

Work is never so dull as when you have somewhere else you’d rather be. Now, I Love my job. But as I sat at my desk getting yet another weekly project report all I wanted was Annie under my desk gagging on my dick.

Tuesday brought with it doubt. Was Annie up for this? What would happen to me if her parents found out? We were good friends. Would Annie tell? Would she simply decide that she wanted to remain a virgin?

By the time lunchtime rolled around I sent her a text telling her to install Telegram, that it was a secure and safe way for us to chat and to add me to it. It took her only a few minutes before she sent me the best message she could.

“Good morning sir.”

Instantly a weight lifted from my shoulders. “Where are you?”

“At school.”

“Go to the bathroom and send me a photo of your tits.” I hesitated whether to say tits, boobs or something else. Weird the difference between saying one in the heat of the moment and writing it out.

“I’m in class at the moment.”

My first instinct was to tell her there was no rush, but I wanted to see how far I could push her.

“Excuse yourself to the bathroom.”

A few minutes later a grainy photo of her perfect round tits and cute pink nipples appeared. The bathroom had shitty lighting, but everything could be clearly seen. At the very top of the photo I could see one hand holding up her shirt while her bra occupied the bottom around her belly.

“Face too. I want to see as much of you as possible.”

An almost identical photo then arrived but with her mousey face blushing as she looked away from the camera.

“You’re stunning. I wish you were here with me right now.”

“Thank you sir. Should I go back to class now?”

“Not yet. Send me a photo of your bare Pussy first.”

I waited and waited but nothing arrived, until eventually…

“I don’t know if I can send that, sir.”

Smart girl. Of course she shouldn’t be sending nudes out like this. But, I want her to do what I tell her, not what she’s comfortable with.

“That was an order, not a request.”

Within a minute I was looking at her Pussy in a photo taken at an awkward angel as she tried to capture it straight on while standing up. There was a thick bush of brown curls.

“You have the prettiest little Pussy my slut, but if you’re coming here this weekend, that needs to be trimmed.”

“Yes sir.”

I was about to let her back to class when I had a thought.

“Have you sent nudes to Dylan or anyone else before?”

“Yes sir.”

I smiled. Of course the little shit had gotten her to do it. I told her to send them all to me. Within a few minutes a dozen or so photos arrived. They were all of her boobs. The guy lacked any imagination.

“One more photo then we’re done for today. Put a finger in your little slave cunt and send me a photo of it.”

It took three agonising minutes but the photo did eventually arrive. The very tip of her finger was just inside her lips.

“You don’t masturbate, do you slave?”

“No sir.”

“Are you wet?”

The typing indicator flickered on and off, before eventually she sent the word “yes.”

“Would you like to be here with me?”

“Yes sir.”

I decided to get bold. I unbuckled my belt and loosened my pants, pushing them down my legs. I took a photo of the space beneath my dark wooden desk with my standing cock in the middle.

“If you were here, you’d be under my desk with my cock in your throat. Is that what you want?”

“Yes please sir.”

I liked the please. It was so hard to get across enthusiasm by text.

“Do you have a Free period tomorrow?”

“After lunch.”

I sent her my office address.

“Be here at lunch. Tell the receptionist you’re my Babysitter and you’ve come to pick up keys. I’ll make sure they let you in.”

“Yes sir. I can’t wait.”

“And I can’t wait to pinch those perky little nipples between my lips.”

“I can’t wait to suck you again.” She was feeling bolder.

“I want you to take me deep. Are you ready for that?”

Instead of a message she sent me a photo of her tits, holding one in her hand and blowing me a kiss.

“I have a Free period after this.”

I was sorely tempted to say yes but I liked the game of temptation we were playing. Besides, I had a full afternoon.

“Tomorrow, you eager slut. Have you dumped him yet?”

Hesitation, then “No sir.”

“That’s your homework for tonight. If you get wet between now and tomorrow, send me a photo showing me. Understood?”

“Yes sir.”

“Good. Go back to class.”

—–

My phone beeped just after I said goodnight to my kids. When I opened it I was very glad they were gone. Tapping the notification revealed a crystal clear image of plump teen Pussy lips with a glossy sheen between them. I cracked a smile and replied, asking her what she was thinking about to get her so wet.

“You sir.”

“What about me?”

Hesitation. “Just you.”

This girl confused me. She sent me a nude just as I’d requested but she couldn’t let herself describe the thoughts in her head.

“Can you talk?” I asked.

“One sec.” A minute or so later she replied with “Okay” and I video called her. She looked embarrassed when she picked up and I noted the earphones she was wearing. She was also relaxing in her bed, plumped up pillows behind her shoulders.

“What were you thinking about little slut?”

“Just you,” she paused, then said very quietly, “sir.”

“Your parents are home?”

She nodded. “They’re downstairs.”

“You’d best be quiet then you little slut. Show me your Pussy.”

She moved the phone with an outstretched arm and her cute furry mound came into view. There was a sheen of reflected light.

“Were you playing with yourself?”

“Yes sir.”

“Show me.”

A pair of fingers appeared and began rubbing her clit. She started slowly, rolling them in small circular motions. I talked dirty to her, giving her words of encouragement, calling her “my girl” and “little slut”. Eventually she crescendoed, not stopping when she reached the peak as she would’ve done before I taught her what the feeling really meant.

As she relaxed back her phone drifted back up to show her face.

“Did you dump him yet?” I asked sternly.

She was suddenly shy and embarrassed. “No sir.”

“Why not?”

She mumbled about being scared and unsure.

“It’s really simply. Text him that it isn’t working out and you don’t want to see him anymore. If he reacts badly, we’ll deal with it together. How does that sound?”

She nodded happily. “Thank you sir.”

I smiled. “Lift your top, baby girl.”

She smiled and lifted her T-shirt over her perky tits. “Pinch a nipple. Harder, harder. Good girl. Now twist it.” Joy turned to pain on her face.

“The next time you wait around and don’t do as I tell you immediately, I will be the one pinching your nipples and I won’t be as weak or gentle about it as you. Is that understood?” She nodded furiously. “Let go.”

I bid her goodnight shortly afterwards. My phone beeped ten minutes later with a screenshot of her breakup message to Drew and no immediate reply.

—–

“Jodie, my Babysitter is coming by today to pickup the house keys. Can you send her straight in when she does?”

Jodie nodded, gave me her most professional smile, and replied in the affirmative. I thanked her and entered my cosy warm office, making sure to shut the door behind me. Jodie Bennett had been my secretary for just over three years. She was also an extremely good fuck.

I’d dragged myself to the first office party after my Wife‘s death, knowing that my departed Callie wouldn’t want me moping around at home. Jodie was fresh at the company and while we had exchanged the usually boss/employee pleasantries we’d not yet really gotten to know each other. We’d talked that night and, after a few drinks, exchanged brief life stories. Suffice to say, an hour later I had her tits face down on the photocopier as I fucked her doggystyle in the print room. What she had instigated as a pity fuck I had taken control of and treated her like a lioness in need of taming and she’d responded in kind. Her blond hair and skinny figure meant that most men had treated her delicately. I was the first to give her what she truly needed. I still had the photocopy in my desk drawer.

We’d agreed after that to keep things professional. We flirted outrageously, and we both knew that the other was open to another fuck, but it was no more than that and we’d worked well together ever since.

I know she saw the smile I tried to hide when talking about Annie, and once my Babysitter had been in my office for an hour ‘picking up keys’ she’d know exactly what was going on.

Work plodded along until midday when Jodie buzzed me. “You have an Annie MacArthur to see you.”

“Thank you, send her in.”

I looked up and saw Annie enter. Jodie looked her over as she walked in then winked at me before shutting the door.

Annie stood there like a deer in headlights with a laptop bag by her side. I looked up and smiled at her.

“Good morning,” I said as my smile dropped. “Strip.”

She was dumbstruck. No niceties?

When she didn’t move, I stood up. “I told you that if you came here today you’d have my cock down your throat. You know precisely why you are here, so strip naked.”

Slowly, she worked herself out of her daze. First she put the bag on the floor, then took off her top, skirt, shoes and socks, leaving herself standing in her underwear. The bra was a baggy simple black affair, and her white cotton panties were a few too many washes past white.

“Are you naked?” I ask her sternly.

“No, sir.”

“Did I tell you to stop?”

“No… Sir.”

She slowly reached to her back and unhooked her bra, letting it slip from her arms to the floor. She briefly tried to cover her breasts before realising she still had her panties to take off, so she slid them down and, watching my expression closely, stood back up straight with her arms at her sides.

“Good,’ I said as I devoured her with my eyes. She was petite and curvy, her lines soft and smooth with her suckable tits and grabbable hips providing perfect counter balance to her narrower waist. I stood and walked slowly to her. “Don’t move,” I warned.

I ran my right hand delicately down her left arm, bent my head and kissed her neck. She trembled and moaned as my lips and fingers barely made contact with her skin, instead stroking those fine invisible hairs that cover us all and sending electric shocks down her spine to the core of her lust.

“You’re a very beautiful young woman, Annie.” My Free hand glided from her other shoulder to her full breast, where I abandoned my testing and grasped her tit flesh firmly. She moaned into my ear as I pressed my lips to the dedicate skin of her neck and sucked hard.

“Why are you here?” I asked as I pulled away, admiring the bruising hickey I had left.

“To suck you, sir,” she replied breathlessly.

“And how are you going to do that?” My lips drifted down and took her nipple into my mouth between my teeth. I gently bit as I grasped her firmly at the waist.

She couldn’t answer, instead she naturally tried to grind herself against me.

“Well, slut,” I released her as I licked her pebble firmly. “I told you yesterday what I would want from you today. Shall we get to it?” I sucked hard.

“Yes- yessir,” she gasped.

I released her and stepped back. “Well you’d better get down there then.”

Without saying a word she stumbled over in her lightheadedness and, with an awkward smile to me, knelt under my desk. I stepped back behind my desk and, with deliberate slowness, unbuckled my belt and removed my pants. I pushed my boxers off, sat down in my plush chair and pulled myself into my normal work position but with my legs on either side of the teenager below.

Reservedly, a small hand worked it’s way around my soft cock and began loosely stroking up and down. I lowered my chair and schooched forward. “I didn’t ask you here to stroke it.”

The hand stopped and after some shuffling I felt a warm wetness at the tip. It slowly spread itself down my hardening shaft, bobbing back and forth as Annie took more of me inside with each nod. Her tongue swished side to side, coating me in fresh saliva and lubricating my entry between her lips. Her hands rested on my thighs, supporting her as she leaned forward to try and take more of my cock in her mouth. She reached the halfway mark and coughed, meeting the limit of her comfort. One day I would push her past it and she’d swallow me whole. For now though, I had a different project.

I pressed the intercom button on my desk. “Jodie, can you come in for a moment?”

The tinny speaker replied with “Of course” and the office door opened. Jodie looked very confused as she entered and didn’t see Annie. I nodded to the pile of clothes on the floor and a smile crept across her face.

“What can I do for you, sir?”

“Take a seat, I want to discuss the schedule for this week.”

“Of course,” she said as she dropped into the seat opposite.

Under the desk, Annie stopped her ministrations with only the tip of my cock in her mouth. I figured she was waiting for Jodie to leave. Not going to happen.

I put a hand on the back of her head, grabbed a tuft of hair firmly, and encouraged her back down my cock. “So, what’s on the schedule for this week?” I asked as nonchalantly as I could manage.

Jodie nodded below the desk and gave me a questioning look. I nodded back and gestured to her phone. “Oh, uh, this afternoon we have the admin team from the airport coming by. It’s technically a troubleshooting meeting but you wanted to be there in case there were any questions about the contract-“

Annie gagged as my cockhead firmly pressed against her tonsils. I held her struggling head there for a few seconds before giving her some Free breaths, then pulled her back into place. As she lightly coughed, terrified of being caught, I asked a banal question about the team in question.

Jodie, flustered, gave me a wicked smile as she replied. “They have a new implementation manager onboard,” she said as she raised her legs and hooked each one over an arm of her chair. Her office skirt rose up to her butt and she began to stoke her slit through her thong. “He’s apparently up to speed, but he has some questions about the billing.” She teased me by slowly stroking her clit, then pushing the gusset of her panties aside to reveal her landing strip garnished snatch. At that moment I couldn’t fathom why we hadn’t kept things going.

Overwhelmed, I took full control of Annie with both hands and used her face as a masturbatory tool. Jodie and I did the best we could to keep the conversation going until eventually she stopped to stifle her moaning as she reached her peak. I was silent as I fucked Annie’s warm, wet, welcoming mouth hole furiously, feeling the pressure rise until eventuality I erupted in spurts against the teenager’s throat. Exhausted, I put my finger to my lips and pointed at Jodie to leave. She tucked her underwear back into place, stood and fixed her skirt, then quietly left the room as Annie coughed and spluttered between my knees.

Once I’d regained my composure a little I wheeled back in my chair and was in awe of the sight below me. Cute, doe-eyed, usually pale faced Annie was flushed bright red. Her mascara and colored lip balm were smeared across her face and a thick mix of cum and saliva dripped from her mouth and nose down her chin and splattered all over her perky teen tits.

“You look beautiful,” I said without a hint of sarcasm. I pulled a box of tissues from a desk drawer and offered it to her. She took a few and began to wipe at her nose and chin while I bent down and helped her up. She was still dazed, so I turned her around and pushed her into the desk. I stood behind her, cock at half mast between her butt cheeks. I worked a hand around to stroke her sloppy wet Pussy lips while the other roamed from her stomach up between her breasts and encircled her throat, gently squeezing the tubes within.

“This is what it means to be my slut. I will have you any way I like, anywhere, and you have no choice but to say yes.” She cooed and her knees buckled slightly as my fingers shifted up and began rolling circles around her clit.

“If you come to me this weekend,” I continued, “this is how our relationship will be. I will own your body and use it however I like.” I turned her around sharply and lifted her Ass onto the cold wooden surface of my desk. With one hand I pushed her to lay back as I bent down and took her engorged button between my teeth and sucked hard. Her knees wrapped around my head as she squeezed in sudden Orgasm. Once the rush of it passed, I pulled us both back up and kissed her hard, releasing her to see the evidence of her wet cunt on my lips and chin. “I’ll make you feel things you aren’t even aware are possible.” I kissed her gently on the tip of her button nose and stepped back to put my pants back on. She remained in shock, dripping with my white cum and standing naked against the desk that held her upright. She was so out of breath she couldn’t speak.

I reached into my pants pocket and pulled out my phone. She flinched and tried to cover herself but I admonished her and had her hold out her arms by her sides as I took some shots.

“Now get dressed. You have class soon.”

—–

Thank you all for your feedback on chapter 1! Please comment any feedback you have,I Love hearing from you.