Submissive New Babysitter

This is the 5th installment of my series about my post-marital sexual journey. Read the first story (Babysitter Lauren) or my profile, for any background needed. You may see references to prior stories/people, but for the most part each story stands on its own.

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Kendra

After about six months of separating from my wife, and soon after Denise and I split up, my ex-wife and I had an after-school sitter quit on us in the middle of a school year, and we had to scramble to replace her.

We were in a jam. Then we got lucky.

Kendra was the younger sister of someone (Audrey) who had been an occasional evening and weekend babysitter for us when the kids were babies. I remember Audrey telling us (about seven years prior) about her sister Kendra, who had just dropped out of college, moved back home, was basically a lost soul. Their father had left them when they were very young and was never around, Kendra didn't even remember him. These girls had no father figure in their life, and Kendra couldn't ever deal with that. She was a hot mess.

Fast forward seven years later, and Kendra had apparently turned her life around. Got her real estate license, and was selling homes in and around our region for a couple years. We had called Audrey to see if she knew of anyone that could help us, and she got us in touch with Kendra, who agreed to help us out after school. She had a flexible schedule, so she was available to accommodate us for two or three hours after school each day.

Both kids were now in elementary school, so it was a matter of picking them up, getting them back to the appropriate parent's house, and doing the usual after school things. We shared custody, so some days it was my house, other days my ex-wife Caitlin's house.

Kendra was young - only 25. She had light brown hair, average height I suppose, maybe 5'4", and a bit thicker. Not fat by any means, but a bit bigger of an ass, thicker thighs and some really big tits.

Around me, she was very formal and proper. "Yes sir," "of course sir," and addressed me as Mr. (Last Name). With my ex, she was much less formal, using Caitlin's first name and generally being much bubblier.

One day I said, "Kendra, please call me Phil," and I asked her to just be herself around me like she is with my ex-wife.

She apologized and said that she's not always comfortable around older men, but she'd try.

Over time as I dug a bit deeper, she mentioned that her therapy had revealed that she wasn't comfortable around men because she had no father, so she didn't have much experience around grown men. That's why she dropped out of college, too many male professors, several of whom preyed on her.

I was shocked that she told me this, but once she did, a light bulb came on for me - she has daddy issues.

Now, I've heard that term before, but never really knew what it meant. But I was determined to find out. I wanted to fuck her, but I needed to be careful or I'd scare her away. She needed to trust me first.

So, over the next few weeks, I treated her more like family than an employee. I had her stay for dinner with us often, took her with us for ice cream after, bought her gifts, the whole nine yards.

This all paid off, because one day, out of the blue, she texted me a picture of herself in a bikini in front of a mirror. I thought maybe it was a mistake and meant for someone else, so I said nothing. The kids were with my ex that week and so I didn't expect to see her.

A day later she texted, "Didn't you like it?"

Playing dumb, I asked, "Like what?"

She said, "My picture. Am I fat?"

"No of course not, you're beautiful," I responded. "I just thought it was meant for someone else so I didn't want to embarrass you."

She said, "Do you really think I'm beautiful?"

I replied, "Oh yes, you are stunning and quite sexy."

"Do you want to see more?" she asked.

This girl was desperate for attention, so I said, "Yes, I want more. I want to see it all."

She sent a pic of her bare tits, which were everything I had hoped and expected. I spent the next hour or so instructing her as to what pictures to take and send, and over the course of the rest of the evening, she sent me pix of her tits, her pussy, her asshole, with a dildo inside her, sucking the dildo, everything. I was blown away; sweet little Kendra a naughty slut.

Toward the end of the night I said, "After you are done at Caitlin's tomorrow, come to my house. Be here by 6:30, not a minute sooner or later. Use the back entrance, the door will be unlocked."

She replied, "Yes sir."

When she walked in the door the next night at exactly 6:30, I called to her to come to a small room where I worked when I worked from home. She found me sitting in a chair, naked, stroking my hard cock.

I said, "Come over here."

She walked over to me and stood in front of me, still.

"On your knees, stroke my cock," I commanded.

She obeyed, never taking her eyes off of it.

"Look at me."

She did, while she stroked.

I said nothing, I wanted to see what she would do. Most women would eventually start sucking it, but she didn't. She wanted to, but she was waiting for permission.

Finally, she pleaded, "May I please suck your cock?"

I nodded, and she lowered her head and gave me some long slow licks and sucks. I coached her.

"Lick me like this, suck like this, deeper, use your hands here etc."

She was a willing and eager student. She was getting me close to coming, so I stood up, grabbed her head on both sides, and started fucking her mouth and throat. She didn't know how to deep throat, but she was going to learn or die trying.

I said, "Look at me, and no crying."

I shoved my cock down her throat and fucked her like it was her pussy. She was gagging and drooling, thick ropes of saliva falling out of her mouth, but she never pulled away.

"Grab my balls," I ordered, then, "Stop, look at me."

She looked up, my cock still buried in her throat, her eyes teary but looking happy.

"I'm going to come down your throat. Have you ever swallowed cum before?"

She nodded.

"I thought so, slut. Swallow it all, every drop. Don't disappoint me."

With that I resumed fucking her throat, harder, working to my orgasm. I hadn't blown a load in over a week, so this was going to be a doozy.

Finally, I thrusted all the way down, she gagged and coughed up some saliva, and I unloaded right down her throat. She was gasping for air, but never tried to get away. I could hear her gulping. When I was done, she held my softening cock in her mouth.

I said, "OK," and she pulled back, her eyes teary, her mouth covered in cum and saliva, but an oddly satisfied look on her face. She had pleased me, and that pleased her.

"You can go," I said. "I'll be in touch."

This was going to be fun.

Kendra and I didn't communicate for the next two days after I had abused her throat. On Friday of that week, I texted her, telling her to come over that night. She said she had plans, and I asked what time. She said 8:30.

I said, "Change it to nine and be over at seven."

Her response: "Yes sir."

At seven sharp she came in the door. I was in the kitchen with dinner and some wine. Grilled salmon (her favorite I knew) and some jasmine rice with fresh Brussels sprouts. She was blown away, not expecting this. I'm sure she expected that I'd order her to suck my dick again.

We ate and chatted casually like old friends. After dinner, we cleaned up together. By now it was about 8:30, and I could tell she was anxious about her plans at 9, figuring I'd keep her in for some more depravity. So, I asked her about her plans.

She was meeting some girlfriends out at a local bar. I told her to be careful, not to drink and drive and to be safe on the streets, and to call me if she needed a ride.

As she was nearing the door, I said "I'll expect you back here before midnight."

She stopped but didn't turn around. This had taken her by surprise, but she said, "Yes sir".

At 11:59 I texted her: "Come to my bedroom."

I knew she wouldn't be a minute late or a minute early. She walked in, and I was on the bed with just some shorts on.

I said, "Take your clothes off, I want to watch you."

Her body was amazing, especially those tits.

When she was naked, I said, "You are incredible. Come over here and lay down."

She did, and for the first time, I kissed her. Slowly and lovingly, running my tongue in and out of her mouth, around her lips, making her squirm and moan. I worked my way down her body, first her neck, then those tits. I went from one to the other, her big nipples poking straight out. I squeezed her tits together and sucked both nipples at once. A little bite made her gasp.

Down to her stomach, I tongued her pierced belly button a bit, then finally to her pussy. She was totally bare, probably lasered. She had big meaty pussy lips, and I knew I'd be sucking that meat into my mouth soon.

I figured she'd never had a proper pussy licking, so I gave her my best. I licked, sucked, swirled, fingered and gave my A+ treatment. Normally I'd have given the woman two or three orgasms by now, but she was a tough cookie. She was making all the right sounds, her pussy was so wet, and she was squirming like a fish out of water. But no orgasm.

Just when my cunnilingus confidence was about to be shattered, the light bulb came on again.

I moved my mouth from her pussy, looked up at her and said "You may come."

Just like that the flood gates opened. Kendra squeezed her legs around my head and let out a primal groan. Cum flowed out of her pussy and my bed was soaked. She shuddered for a good minute, kind of like aftershocks after an earthquake. I wished for a moment that I was a spectator just watching this from a distance, it was so erotic how she just couldn't do anything without permission.

After she came down, I stood up and took off my shorts, my cock hard as steel. I laid down on my back, as she waited for instruction.

"Suck me, slowly and gently for a minute or two, then when you're ready, ride me."

She obeyed, tenderly loving my cock and balls with her tongue and lips, slowly into her throat as I had taught her. I had the urge to fuck her throat again, but that wasn't the instruction I had given, and I didn't want to break our trust.

Eventually she moved up on me, and we kissed deeply for a minute or so. All the while she was rubbing her wet pussy along my cock, but would not allow it to penetrate her.

Finally, I said, "whenever you're ready" and she slowly sank herself onto my cock.

Kendra took her time, a slow agonizing descent that was amazing to feel and even more amazing to watch in her eyes. They rolled back slowly as I penetrated deeper, and she groaned loudly when I was all the way in.

She sat up straight and just sat motionless, then slowly gyrated her hips so that she was rocking back and forth. She put her hands on my chest and used it as leverage to raise herself up and down, letting about half of my dick out before plopping back down.

I could tell that she was getting close, and I wondered to myself how this would play out.

As if on cue, she said, "Can I come, please?"

To her dismay, I said, "not yet" and she let out an audible sigh of frustration.

I stopped her from moving and sat her straight up again, grabbing those big tits in my hands and squeezing them. I flicked my thumbs over her nipples, and then started thrusting into her again.

Finally, without warning I pinched both of her nipples hard and said, "Now you can come."

The flood gates opened instantaneously again. How she was able to hold back like that I have no idea.

Without giving her a chance to come down as before, I flipped her over while she was still in mid orgasm, and pinned her legs back, my hands on the backs of her knees, and pounded away. Her big tits flopped up and down, she was moaning and groaning incoherently, and she was lost in the ravaging I was giving her.

I was getting close, and I decided to change things up and see what happened.

I said, "I'm going to come soon, tell me what you want."

Submissive as she was, she had no trouble expressing her own desires when she was permitted to do so.

She immediately said, "My tits, my face. Come on my tits and my face."

I wasn't expecting this, and it was a major turn on, so I quickly pulled out and straddled her around her mid-section, on one knee and one foot.

I said, "Open your mouth," and she complied.

I pointed my cock at her tits and fired a shot, then aimed higher and got the next couple shots on her neck, face and mouth. She used her hands and fingers to rub my cum on her tits and shovel cum into her mouth. I had come on other's faces before, and those experiences were hot in their own way. This was different, like she NEEDED my cum, because it pleased me, and she needed to please me.

I remained on top of her, my dick slowly softening. I lovingly scooped up some cum from her neck and fed it to her, and did the same with the rest of the cum that she didn't get herself. Finally, I moved up and put my now flaccid cock into her mouth for her to clean off.

I finally rolled off of her, and looked down at her.

She asked, "Are you happy?"

I replied, "How could I not be?"

She smiled and rolled over to sleep.

When she woke up the next morning, I was already awake. I was downstairs and heard her go to the bathroom and hop in the shower.

I knew she liked coffee, so when she was done with her shower, I brought her a cup, and we lounged on the bed and sipped coffee. She was grateful and sipped it slowly while I watched her. Not many words were exchanged, not due to awkwardness, but because we were both just enjoying the moment.

When she was just about done, I said, "Lay on your stomach and face that wall."

It was the wall opposite the big mirror I had in my room. I stood next to her and put my cock in her mouth, and I could watch her ass in the mirror while she did it. I grabbed her head and started to fuck her throat again, less violently than the first time but still forcefully. She had already learned and was effortlessly taking my entire cock in her throat.

I had my hand wrapped in her hair and was directing the pace and depth, and she willingly let me do whatever I wanted.

I pulled my cock away and said, "Turn around, on your hands and knees."

Again, she complied, and then spotted her reflection in the mirror and let out a little sound of surprise. Looking down at her ass and into her eyes in the mirror, I shoved my cock into her in one motion. The bed and her body were a perfect height, and I could pound away flatfooted and really get a rhythm going. Her big tits were swinging, she looked so good.

I played with her asshole a bit, fondled her tits, and finally gave her what I knew she would love. I reached up and put my hand in her hair, on the top of her head toward her forehead, and pulled back HARD!! I yanked her head back by her hair, it must have been painful, and she came immediately.

Pulling her hair, looking at her face in the mirror and pounding her ass, I couldn't take it.

I said, "I'm going to come soon. I'm going to come in your pussy."

She said, "I'm not on the pill. Is it safe?"

I assured her, "I can't get you pregnant."

I could feel the worry leave her body with that statement.

She looked back over her shoulder at me with a new hunger, and said "Fill me then. Fill me with your cum. Please sir. I need it, I need your cum in me."

I obliged her, grabbing her hips and filling her up from behind. When I stopped spasming, she got off the bed, dropped to her knees and cleaned me off again.

She was a good girl.

We spent an hour or so lounging in bed, then went downstairs where I made her some waffles and fruit.

When we were almost done, Kendra spilled some of her coffee on the table.

I looked at her sternly and said, "Clean that up, then meet me upstairs. You're a bad girl and you need to be punished."

"Yes sir," she answered, with a bit of a tremble in her voice.

I retreated upstairs to my bedroom to wait for her. Twenty or so minutes later, I heard Kendra in my doorway.

I was sitting in my small chair in my bedroom, and I motioned for her to approach me. She stood in front of me and looked at my hands -- I was holding a wooden ruler.

Kendra immediately understood. She removed the tee shirt she was wearing and lowered her skimpy panties, then laid across my lap, naked.

Gently I rubbed her ass cheeks with my hands, squeezing the firm globes and spreading her cheeks, getting a good look at her asshole, which I planned would be the next hole of hers that I stuffed this morning.

After a few minutes I said to Kendra, "I'm sorry I have to do this to you."

I brought the ruler down with a hard "smack!"

Kendra cried out, but before she was done with her initial yelp, I smacked her again. I wasn't hitting her very hard, I'm sure the pain was no more than a light sting, but her ass began to turn red after a few smacks on each cheek.

I laid the ruler on the night stand and grabbed a tube of Vaseline. With a small drop on each cheek, I massaged her red ass for a few minutes. Then I put another drop on my thumb and slowly worked it around her asshole, ultimately getting my whole thumb inside of her ass. Kendra was squirming and moaning as I did this, and thrusting her ass back at me to get my whole thumb inside of her.

Finally, I pulled my thumb out of her ass and instructed, "Bend over the bed again, like earlier."

She complied, assuming the same position she had been in about two hours before. My target this time was different, though, and Kendra reached back to spread her asscheeks, knowing and encouraging my next move.

Placing the head of my cock at the entrance of her ass, I reached up and grabbed Kendra by the shoulders. Pulling her back toward me, my cock head popped past her anal ring and into her ass. Kendra groaned in response, and I slapped her ass again.

"This is punishment, not pleasure!" I scolded her.

She immediately quieted down, though I knew she was enjoying every second of this. Grabbing her shoulders, I pulled her back toward me as I thrust again, all but the final inch or so penetrating her. I pulled my hips back, and Kendra thrust her ass back at me urgently. Craving all eight plus inches fully into her bowels.

Once I was fully buried, my pace increased, and Kendra kept up, throwing her ass back at me with fury. Prior to this, I had no idea whether Kendra had even been ass fucked before, but given the ease with which she took me and the violence with which she was throwing herself back at me, I knew for sure that this was not her first anal rodeo.

As I prepared to come, I forced Kendra down flat on the bed, her feet still on the floor, pushing her face into the bed and making it hard for her to breathe. My hand on the back of her head, I unleashed another load into her, this time into her rectum, and the cum bubbled out around the seam as she couldn't contain it all.

Letting her up for air, I withdrew my cock from her. It was visibly dirty from her ass.

"Look at me," I ordered. "You got shit all over my dick. I guess you haven't learned a lesson yet. Get into the bathroom."

I followed Kendra into my bathroom, which was not real big, a standard size tub/shower with a sliding glass door.

"Start a warm shower for me."

After the water warmed up, I stepped into the tub, the warm water hitting my back.

"Get in."

Kendra complied, standing in front of me, cold and shivering.

"On your knees."

She dutifully dropped down, my feces-covered cock inches from her face.

"Look what you did to me."

She looked up at me.

"I'm sorry," she squeaked. "I'll clean you off."

I wanted to see how far she would be willing to go. I'd never let anyone put a cock in their mouth after anal sex, but I wanted to see if she would.