Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 13

Coming of Age Sex Story: Chapter 13 - Join Brian back in 1984 in sunny South Florida. He's obsessed with his babysitter Rachel. She's cute, quirky, big glasses, and a little older than him. She's babysitting him for the entire weekend. He's going to discover that Rachel Wagner and her family live a very different lifestyle than anything he's ever seen before and it is going to blow his mind.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   mt/Fa   Teenagers   Consensual   School   Slut Wife   Incest   BDSM   DomSub   MaleDom   Humiliation   Light Bond   Spanking   Gang Bang   Polygamy/Polyamory   Interracial   Anal Sex   Enema   Exhibitionism   First   Facial   Fisting   Food   Oral Sex   Sex Toys   Squirting   Tit-Fucking   Water Sports   Babysitter   Public Sex   Nudism   Illustrated  

“Did Lori ever suck your cock?” Dennis asked. It was an incredibly odd feeling to hear a father be so casual about whether his daughter had just given someone she just met a BJ.

“No.”

“I think Rachel gives better head,” he lifted his daughter’s chin, and she smiled up at us and blushed.

“I try,” Rachel admitted with a bit of a frowny grin.

“I need your help for this one, Brian. We are going to give Rachel the rowboat treatment. Are you up for that?” he held up his meaty fist.

I was up for anything with Rachel!

Rachel was already moving into position on all fours. She placed her palms flat on the sandy pavement and kicked her legs wide. Dennis removed the padlock that was hanging off of her pussy lips with a key.

“I’ll work the rudder, you work the steering wheel,” Dennis indicated his daughter was the sailboat. “When I’ve just shot my load, I’ve still got some tools,” he pushed two fingers into his daughter’s pussy and began to wriggle them to get her wet.

Rachel looked up at me with her brown eyes. She had an adoring expression on her face that made me think she really liked me. She bit her lip a little and asked me to take my dick out. I looked at Dennis to make sure that was okay. He didn’t say anything. He was busy working four fingers into her pussy as she humped and gyrated her hips into his fist.

I unzipped my pants. My dick was hard, and my balls were sore from a full day of walking around hard as a rock. I masturbated so frequently that my Dick really wasn’t used to storing up cum for long periods. I felt hornier than ever with the weight of all that ejaculate in my balls.

I fed her the tip of my dick. I was unsure of what she was going to do. I have to admit that I was afraid she’d bite down. She began to kiss and lick the tip of my dick like she had that huge dildo in her yard. I still didn’t know that she was giving me a “blowjob.”

Her mouth felt great, but awkward. I was so used to my own touch and pace when I masturbated that I wanted to stroke my cock into her mouth. She wouldn’t let me. Instead, she raised up and used her hands to rub her spit all over my dick while slurping.

Rachel groaned in ecstasy. I wanted my babysitter to enjoy this so much. I don’t know if even considered her a babysitter anymore. I wanted her to get something out of what we were doing because I felt so guilty that I was using her face.

I also wanted her to enjoy it (for selfish reasons) because I wanted her to like it enough to do it with me again!

I thought that her moans and coos were simply because she loved the taste of my dick so much. The passionate moans were really caused by her father pushing his entire hand to the wrist into her pussy. I could tell because the more he pushed, the more excited she became.

He began to work his other hand into her asshole. She slobbered all over my dick lovingly but the intensity she was showing me was a direct result of the stimulation she was getting from behind.

“Cum for me, Brian!” she begged as she worked my cock further into her mouth. I felt I should be hitting her tonsils. I was shocked that she took my dick even further.

“Choke her with it and pull her hair,” Dennis insisted.

I didn’t want to be mean to Rachel. She wasn’t like Lori. She hadn’t tried to make me beg and tease me. She was being so generous with her mouth. I only wanted to do something if it gave her pleasure. Lori looked like she didn’t enjoy it when she was being choked.

Dennis kneaded her pussy and asshole with his fists like he was pumping her up in a game of Dig Dug. That was one of my favorite video games. If you can catch a Pooka with an air pump, you can pump them until they explode.

The look in Rachel’s eyes suggested she would explode. A tear began to run down her face. I caught it and wiped it away.

“Oh fuck, fuck me, go on, harder! Harder daddy!”

I was a little jealous that her father was getting her dander up so much. I wanted to get that reaction from her. I pulled her hair lightly, and she didn’t stop me. She seemed distracted by the building orgasmic reaction she was having to being double-fisted.

It dawned on me that despite it being unlikely, it was still very possible for someone to walk upright then and catch us with Rachel.

The concept of humiliation really never appealed to me until that moment. The Wagners had talked about it. They had definitely demonstrated it. I thought it was weird and funny, but I didn’t quite understand why they participated in it.

Why would they want to be the butt of the joke? The girls could be sexy, alluring, vulnerable and charming when they wanted to be. I was still grappling with why they liked to be humiliated at times as well.

However, thinking about what I’d do or say if we were caught really turned me on. I didn’t want to get caught. I could imagine a bunch of tough guys walking up to us. They’d ask us what was going on. Then they’d want to use Rachel after we finished.

They’d act like some guys putting quarters on an arcade machine and calling dibs. We’d watch as the first three guys took turns rowboating her. They would tell their friends and soon dozens of guys would show up. Rachel would be covered in cum and sweat and keep sucking like the Energizer Bunny.

That might happen, or maybe we’d be caught by somebody who was shocked. I imagined that woman that called us out at the Football game when she heard me say cunt. I wondered what she would say if she saw us out here at the end of this street doing something this depraved?

She’d call us perverts and look down her nose at us. I didn’t see that as a problem though. I kind of wanted to shock her. It was a strange start to my life-long awareness that I’d be intrigued by public flashing and acts of humiliation.

All the different reactions that one could have to acting in a way that is contrary to what people would expect in public were starting to turn me on in ways I didn’t even understand.

Rachel’s tender, loving tongue bath of my cock made me associate those feelings with sexual pleasure and I began to instinctively pull her hair the way that Dennis had pulled her sister’s hair. I began to force her head further and further down on my dick.

I didn’t intend to hurt her. I wasn’t thinking about what I was doing anymore. I was just caught up in the zone of action by instinct. Rachel’s throat felt so slick and accommodating like it was meant as a sheathe for a flesh sword to be stabbed down the entire length.

I began to control her head and move it faster and faster. She engulfed my cock with her open mouth and didn’t struggle. She did make me struggle to force her head down on me at an increasingly faster pace.

I jerked off at a pretty rapid pace. It was just my preference to pull myself off by stroking really fast and squeeze my cock at the same time. I made her suck my dick at my preferred pace. She was no longer sucking by the time I reached that point though. I was now effectively just fucking her in the mouth.

Rachel began to make gurgling noises and gagged as if she was going to vomit. I didn’t hear or didn’t care. The “gurk, gurk, gurk, (gasp), gurk, gurk,” from her throat was turning me on. I knew I shouldn’t enjoy it but I did.

At the same time, snot and mucous from her nose seemed to be draining into her throat and replacing the saliva. It was milky like cum and felt warm around my cock.

I no longer paid attention to Dennis and what he was doing to his daughter’s ass and pussy. I didn’t pay attention to Rachel’s pretty face either. I lost myself in a little world of ecstasy and face-fucked her for my pleasure without concern for hers.

I know it sounds selfish. I didn’t think about it though. When I finally started to spurt my load, I realized that she was vomiting milky fluid down her chin and coughing and hacking. Rachel’s mascara was running and she looked miserable.

“Good job,” Dennis reached out to me to give me a high five. His hand was dripping with her daughter’s juices. His other hand smacked her ass hard. Rachel shivered while she gasped for air. She looked terrified and betrayed.

I felt so guilty for what I had done. I had made her throw up and Rachel looked so happy. Her chest heaved from exhaustion and sweat beads were forming on her forehead.

“My cunt is on fire,” she groaned in anguish.

“You’ll get over it! You heal fast,” he smacked her ass hard and her body shifted under the weight of his strike. Her ass didn’t just jiggle when he spanked her.

“Thank you, Daddy,” she answered demurely, and stuck her ass up again so that he could hit it one more time. Her chin was still coated white from snot and mucus. “And you? What was that?” she asked.

I was about to apologize when she opened her mouth and flicked out her tongue to show me a puddle of cum. The expression on her face changed instantly to suggest she considered it a prize. “That was great! The way you fucked my face! That was savage!”

I was beside myself.

Dennis helped his daughter to her feet, while she wiped her face with her arm. She didn’t spit out my cum so I assumed she swallowed it soon after she showed it to me. He smacked her on the ass and told her would meet her down at the 7-11.

“I know, I know, Daddy,” she rubbed her sore ass with her hands and began to jog forward. “There won’t be anyone to offer a BJ to by the time I get there after mom and Lori get done with them.”

“Haul ass! If you aren’t at the dumpster by the time I get there, your ass is walking home!”

“Ooh, streaking all the way to Lakewood? That sounds exciting!” she cooed and ran backwards. Her pretty little tits shook as she faced us and jogged backward.

“Then you’ll miss judgment!”

She turned around and ran faster toward her destination without comment.

“What is judgment?” I asked.

“You’ll see when you get there. I think if I tell you about it now, you’ll just freak out,” Dennis said. That only made me more curious and intrigued.

I dusted myself off, zipped my pants, and got back in the jeep.

“What are you doing?” he asked.

I froze in panic. I instantly imagined he was going to make ME run to the 7-11 in the nude so that I could “understand the elephant as a blind man” or something.

“Wrong seat,” he tossed me the keys to his prize jeep and got in the passenger side.

“I get to drive?”

“No, I was going to drive from the passenger seat. Do you think you can handle it? Or are you drunk on Rachel’s blowjob?”

“That was a blowjob?” I asked as I tried to figure out where the clutch was and looked around at the mirrors and gauges to get a feel for where everything was. Dennis had taught me to drive a stick verbally but sitting in the driver’s seat for the first time was overwhelming.

“Ha-ha, yeah! More like a face fucking! I didn’t think you had it in you.”

I thought blowjobs involved blowing on my cock. I also thought I made Rachel sick. “Why did she throw up at the end?”

“You hit her gag reflex. She can take a lot of dick. The combination of getting double-fisted and face fucked through her off her game. She looked star struck at the end. I’ve never seen her so dumb-struck. There is nothing like making a young girl choke on your dick. Old whores know how to suck a dick right, but there is nothing like using a little cock-sleeve until she cries.”

Dennis seemed impressed with me. I didn’t know what the word sadist was but he was certainly that.

“I didn’t want to make her throw up. I wanted her to enjoy it too,” I said as I fumbled around with the keys.

“That’s how she enjoys it. If you had been gentle and nice, she would have hummed sweetly on your pecker until you came. She isn’t selfish at all. She’ll suck you how you want to suck. You gave her a real thrill. Do you remember Lori telling you about how she loves to be terrified of horror movies?” he asked. He showed me the right key to use and helped me figure out which way to turn it to start the car up.

““Yeah,” I said. I felt a sudden surge of the engine and all this power when the jeep started up for me.

“Rachel probably loves horror movies the most. The girls may have looked like they didn’t care they were running through Naples Manor naked. That’s because they’ve done it plenty of times. They were scared shitless they have to streak through this neighborhood. Every person out walking their dog, or taking their trash out tonight could potentially catch them. They might find a bush or a car to hide behind. They can’t just slip on a pair of shorts they brought with them to put back on. They have nothing. They can’t cover themselves. They would be busted.”

I nodded.

“They know they have to run all the way to the 7-11. It’s Friday night after a football game. That 7-11 is going to have at least a few customers. They have to hide behind a smelly old dumpster. I know for a fact there is some drunken hobos that live out there. They know I will ASK those men if my wife and daughters offered to suck their cocks and there will be hell to pay if they don’t. They are going to be humiliated asking some dirty, disgusting guy who hasn’t showered for weeks if they can slob his knob. They won’t know when we are going to arrive. The unknown can be terrifying too! They will have to hide until we show up. It’s like a wild ride or an adventure to them. Turn right up here,” he said.

“What?” I realized that I was driving. I wasn’t thinking about it at all. I had started the car, managed to get it into gear. Engaged the headlights, and I was driving the car. I wasn’t thinking about it. I was just following the instructions that he had given me all night while he was talking about other things.

“The girls are down at the end of THIS street though?” I asked why he wanted me to turn when we needed to go straight to pick them up.

“Yeah, but we are in a jeep, and we can get there faster. I want them to sweat. I let everybody know that judgment wouldn’t be until after midnight so we have plenty of time.”

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