Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 4

Coming of Age Sex Story: Chapter 4 - 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  

“What you are looking at glistening on my cunt is not pee,” Doris informed me like it was not that big of a deal, but she wanted me to understand anyway.

I was back to staring deeply into Doris’s wet pussy and marveling at how the folds and flaps glistened.

I could no longer meet her gaze and look her in the eye after she caught me lying, anyway. I had occasionally been making eye contact with her just so that I didn’t seem like I was staring at her crotch too hard and too long.

Doris’s pussy was fascinating – so many folds and flaps and they all seemed to fold in on each other like some fantastic Escher drawing. Where would the baby come from when they gave birth? Did it just drop out of the meaty flaps on the side?

Where was her cherry? I could see deeper into her pussy than I had ever imagined. I assumed (incorrectly) that all women had cherries. I don’t mean hymens. I had no idea what that was. I thought they had a tiny and perfectly round flap of skin inside their pussy that looked (and tasted) like a maraschino cherry.

I had heard that once a woman had sex, the cherry burst. I assumed that when that happened then the bright red cherry burst and opened like a flower. Then a tiny baby jumped out like Spiderman climbing the walls of her insides. The baby began an arduous climb into their mother’s stomach to hibernate for 9 months and finally pop out.

It sounds so dumb right now. We didn’t have the internet and my parents never explained anything. All I had as my guide was a creative and somewhat warped imagination.

I had so much to learn anatomically about women’s bodies and here before me was a working model – and a very pretty one at that. I was absolutely fascinated by Doris’s bald pussy. It was engorged and swollen in places and parts even throbbed or moved a little as she shifted her weight around. I nearly swooned.

“I am sorry, Doris. I didn’t mean to offend you,” I apologized. It was the first time I addressed her by her first name. It felt very wrong on many levels. I had literally never addressed an adult by their first name in my entire life. It was always Mom or Dad or Mr. and Mrs. Followed by their last name.

It didn’t feel right to address her as an equal like a kid I met in the schoolyard, and yet it was what she had told me to do.

“You offended me when you lied to me about your sexual status. You didn’t offend me at all when you mistook my cum for pee.”

“Cum?” I didn’t understand at all. “Cum from somebody’s thing? I mean their dick?” I stumbled over the question.

Lori laughed so hard that I thought the cage would fall. “She WISHES that was cum from somebody’s dick!”

Lori licked her lips like it would be yummy to gobble some cum. I had tasted my own pre-cum before. I definitely didn’t think it was a gourmet treat. It was incredibly sexy to know that girls liked the taste – or at least Lori and Rachel obviously did.

“Oh hush,” Doris hushed her daughter. “Women can cum too, Brian. I am not going to get into the medical mumbo jumbo, but different types of discharges come out of a woman’s cunt. What you are seeing is arousal fluid, or female cum.”

I shot copious loads of male cum on a daily basis. Mine didn’t look like that. My cum was thick, viscous, and shot out in wads like big balls of snot or sometimes like white oil.

“Just like you have a hard-on right now,” Doris couldn’t even see my waist from where she was swinging. I did have a boner, but I didn’t know how she knew “I have one too. Only it’s a little different for me. It’s all perfectly natural. Vascular engorgement is just the swelling of the blood vessels because a signal in my brain is telling me that it is time for sex. The hornier that I get the more my body tells my pussy to increase blood flow, which creates pressure inside my vaginal walls and fluid is pushed to the surface. It’s totally normal for a woman to feel engorged, swollen, and slippery when you are horny.”

I was jotting down mental notes as they educated me on what I assumed were the great mysteries of the universe that no boy my age would ever know. I felt like I was being let in on some great secret!

“You seem to like conformity, but every woman has different little buttons that send signals to her brain,” Doris said.

“Yeah, I was dating a quarterback in high school, and I couldn’t get wet. I even went to the Doctor because I was dryer than a Popeyes biscuit! It turns out, I just hated that motherfucker. Everything he said and did just turned me off. He was good looking, and he fucked me okay, but he irritated the shit out of me. I got rid of him and voila, back to having a wet pussy!”

I didn’t even realize Lori was joking until she finished telling the story and waited for me to laugh. I think she was disappointed because I thought she was serious at first. I was too naïve to really get the joke.

Rachel returned and hurriedly began to adjust some ropes in an attempt to bind her own wrists. She didn’t seem the least bit concerned that I saw her naked. She had no interest in joking with me. I was glad they explained how pussy worked before Rachel returned. I didn’t want her to think I needed lessons in how women’s bodies worked.

“Let me guess, you explained how pussies work to him?” Rachel said as she struggled with her rope. She obviously assumed I had no clue.

“Yes,” Doris said with a trace of a smile.

“Did you let him touch you?” Rachel asked as she focused on trying to tie her own wrists. She wasn’t doing a very good job of it and seemed to be getting frustrated.

“No, but he didn’t ask. That’s up to your father anyway,” Doris replied stoically. She asked me if I was ever a Boy Scout.

I was in luck! I had spent three years in the Boy Scouts. It was mostly because I didn’t have many friends and my mother thought it would be a great way to make friends. It really wasn’t.

I didn’t like camping or the outdoors. I didn’t like getting messy either. I did enjoy the arts and crafts and that included mastering knots. I assumed tying knots was a largely useless skill like origami that I’d never really use unless I went boating or camping. I was sure glad I was wrong about that!

“Did you ever get knotty with the other boys you were scouting?” Lori asked me. She implied that I might be gay. At the time, that was considered very taboo and I insisted that I didn’t.

“Pity, the girl scouts didn’t teach me a lot, but it sure was fun eating cookies at summer camp,” Lori implied that the cookies were other girls’ pussies.

“Brian, do you know how to make a single column tie?” Doris asked me as we watched Rachel struggle to get her wrists bound behind.

“Yes, why?” I asked.

Doris suppressed the urge to smile. I suppose I should have picked up on the fact she was asking me if I knew how to tie knots while her daughter struggled to tie one.

“Her father will like that very much,” she replied. “Do you mind helping Rachel tie her wrists up?”

“No, not at all,” I didn’t question it at all. Rachel didn’t say anything to me. She turned around and faced her ass toward me. Then she presented her wrists and crisscrossed them.

It had been a little while since I had done any knotwork. It all came back to me after a few quick attempts. I made what is called a bight with a loop of the rope. I described what I was doing as much for them as myself. I didn’t want to do something wrong and hurt her.

They didn’t seem concerned in the least that I was touching her or that I might make a mistake. Rachel presented her wrists and stood impassively waiting for me to finish.

“Wrap the doubled length around their wrist twice. Then take the bight beneath the wraps. to get the rope through, pull, don’t push,” I said. It was all coming back to me. “Use your finger like a crochet hook, reach beneath the wraps, and pull your bight through. Now, take the other end, make a loop, twist it, and leave this free end of the rope dangling to the inside of the loop.”

I checked to make sure that the knot was sound and wouldn’t cut off her circulation. We did practice these on each other at camp. It wasn’t gay though. “Now, take your bight, and run it through the loop!”

“Just put the end in the hole,” Lori smiled when she made her double-entendre’ joke. She was good at that. She wasn’t using sarcasm and her jokes put me at ease. I might have freaked out if I really thought about what I was doing.

I WAS TYING UP MY BABYSITTER! AND SHE WAS NAKED!

“And finally, put the bight back through your loop, and using your working end, pull the loop shut,” I said as I tested the rope. It was pretty secure and wouldn’t cut off her circulation. It was a little sloppy considering how rusty I was. I was happy with what I had done.

“Well, you DO have your uses!” Doris seemed pleased as well.

“Thank you, Brian,” she turned around to face me. I was standing impossibly close to her butt cheeks. Intentionally, on my part. She looked a little surprised and then asked if I could “tie my boobs the same way?”

“Together?” I asked. I tried picturing how I could tie her tits together like two balloons. The look on Rachel’s face suggested she wasn’t amused. I wasn’t joking though. I really thought they were asking me to try and do that.

“Oh, Dad would love that!” Lori laughed. She was obviously joking. At least, I thought she was.

I couldn’t imagine my father inviting me into any sort of party where women were naked. It was no wonder to me that Brad had grown up to be so gregarious and confident. I don’t mean that he got to boss the women around. I think it was just that growing up around girls who didn’t make you feel like a goofball for not knowing how their bodies worked probably helped a lot.

The women were not meek by any stretch. Lori was out-going and so was her mother. Rachel was a little stand-offish but none of them seemed like doormats that could be trampled on. They did seem very supportive and open-minded...

“No, just tie my tits around the base,” Rachel clarified politely what she wanted me to do. Her tone made it sound like this was a perfectly normal request to make. She made it sound like she was asking me to pass her the butter at the dinner table. I expected her to grin like a ninny because I probably was as I stood there wondering if this was a waking dream.

“I’d have to touch them,” I warned her as I began to put the bight together.

“Okay,” Rachel said.

“I mean, that’s like, okay?” I asked again as I touched her boobs and gave a little squeeze to the side part. I realized that sounded stupid and insecure right away. I was so nervous. I was going to actually TOUCH booby! I had dreamed of this moment. Rachel didn’t have big tits like her mom and older sister. They were decent size for a girl her age. There were girls at school who had huge bazoombas.

“I don’t have to ask your dad first, or anything?” I wanted reassurance that this wasn’t going to get me in trouble. My question only seemed to annoy her. I thought she’d appreciate it if I were polite and respectful.

“It’s not my hand in my marriage, Brian. It’s just my tits,” Rachel made it seem like it was no big deal. Her wrists were bound behind her. If I had wanted to I could have reached between her legs and felt her meaty pussy flaps. She made it seem like her boobs were nothing special any way.

You already know how infatuated I was with this girl. I thought this was the best day of my short fucking little life!! (and it was).

She could have reported me or asked me to leave, I guess so there were consequences. Still, there was nothing she could have done to stop me in that moment. I was briefly tempted to grope her and honk her knockers. It would have been silly but the just looked ripe to be squeezed and it would have felt so good!

Instead, I focused on her request and tried not to enjoy it too much. I avoided her areola entirely. They were very puffy and it was hard to tell where the nub began and the areola ended. I began to tie one tit and she looked straight ahead as if she were bored.

“Do you like this?” I asked. It was a silly question. It was obvious she “liked it” or she wouldn’t be doing it.

“Yes,” she said without a lot of passion to her voice. Rachel made it seem very mundane like playing racquetball or going swimming and perhaps to the Wagner family this is what it was.

“When my dad gets here, will you tell him that I did this?” She asked if I would say she tied herself up.

“What did I just say about honesty?” Doris scolded her daughter.

“Sorry Mom,” Rachel apologized and didn’t ask me to do that again. I had her first tit bound and tied at the base. It wasn’t tied to anything though so it could easily slip off. It slipped off because her boobies were so slippery due to the cocoa butter she applied earlier.

“Could you tie it tighter, please?” she asked when she tested the bindings to see how snug they were.

“I don’t want to cut off your blood supply,” I said.

“Try.”

“Try to cut off your blood supply?”

“Yeah, if you actually can, I’ll kiss you. Okay?” Rachel promised. It was an offer I found impossible to refuse.

“Why would you want me to hurt you?” I said as I thought about the most comprehensive knots that I could remember from my Scouting days.

“Because I like it, and I don’t think you can. If my tits start turning purple, I’ll beg you to untie me and give you your kiss,” Rachel said.

“Stop teasing him,” Doris told her she was being unreasonably cruel. I don’t think she believed I could bind her tits so that it was very tight. I managed to get the rope on her boobs nice and tight, and it did slow her circulation and force them to swell but they certainly didn’t turn blue.

“Okay, frog tie or hogtie?” she asked her mother and Lori to decide.

“It should probably be your guest’s choice if he is going to do it for you,” Doris offered politely.

I didn’t fully understand what she was asking.

Rachel went down to her knees at my feet. She lay flat on her belly. Her wrists were already cuffed behind her back. She brought her legs up and put her feet together very close to her wrists. I could see the raw, red, pinkness of her actual asshole as she lay naked at my feet.

I was truly mystified. I wanted to warn Rachel that I could see her asshole when she spread like that. I assumed she might not want me looking at it and just didn’t realize how exposed it was. Her asshole was so pink and puffy! Like candy!

“Hog Tie?” she asked as she got to her knees and presented me with an “Or”. Then she laid upon her back on the cold tile floor at my feet. Rachel spread her legs so that now I could see her open pussy and her asshole VERY well. She folded her legs so that brought her knees up to her chest and indicated that I would need to tie her ankles to her thighs. “That’s Frog Tie. Which would you prefer?”

I would have instinctively refused to pick and asked her what she prefers but there was no question that Frog Tie exposed the most girl flesh and excited me. “Frog Tie”

“Cool,” Rachel remained in that position. I was able to leverage the ropes she had already tied around her legs calves and thighs to connect them. I think that was the purpose in the first place. She had created bands or belts that could be easily used to bind her in different positions.

Her pussy glistened and became slippery as her body opened before me. In this position, I could see where the dick went into the pussy. The slit that I thought was a butt crack was very narrow. Down toward the bottom, slightly under her hips was an opening similar to her mother’s but not quite as wide and with a completely different topology of wrinkles and folds.

“I forgot my weights,” she realized about the time I finished securing her thighs to her calves. She could have at any time closed her legs. She wouldn’t be able to stand up. She didn’t have to expose herself by keeping her legs apart, but she did it anyway.

I was looking for dumbbells on the table to bring her weights. All I saw were pyramid-shaped lead weights that fishermen attach to their rods. I wasn’t a very outdoorsy type. I did grow up in Florida and my dad used to drag me along and take me fishing on Marco Island. It wasn’t something I enjoyed but I did it.

I knew all about weights used in fishing. The purpose was to make the line sink lower and catch bigger fish! I would never imagine anyone attaching them to their body for a sort of thrill. The lead weights were in plain sight, but I kept looking past them.

“There are three pounds of lead on the table, you can’t miss it,” she was hurrying me in a sort of panic. I picked them up. They were attached by wicked-looking clips that supported the weights on chains.

“Yes, attach the lighter one to my clit please?”

“Five bucks he attaches it to her hood,” Lori whispered a bet to her mother. I had no idea what these body parts were.

I knelt between her legs and held the alligator clip open. It had jagged sharp teeth and I didn’t want to hurt her. “That feels nice but that’s not my clit,” Rachel writhed around in pain. She still didn’t close her legs. My fingers were sticky. I was touching a woman on the outside of her pussy!

I felt like I was traveling to the moon, and I had all the power in the world. Words cannot explain how badly I wanted to take a picture just to prove this was happening because no one would ever believe me.

“I knew he wouldn’t get it right off,” Lori teased. Doris reminded Lori that I was just learning and not to be so critical. “I am just teasing,” Loria said. “Hey, you can do me next when you finish with her. I need a little touch-up before we begin. It’s been a long day!”

I didn’t know what Lori meant. I was busy concentrating on her sister. I let the clamps bite into the fleshy part underneath the biggest fold in the center of her pussy.

“Oh!! That’s way up inside me,” Rachel sounded like she was in distress. I released the pressure of the clip. “No, you can put it there. Just um, put the other two a little closer to the outside. Okay? Thank you. Yes, that’s good.”

She had four clips she wanted me to hang from her right pussy lip. I didn’t know why she had stretched them out. I assumed that at one time there was some symmetry between pussy lips and they were relatively the same size. She sighed through her teeth and thanked me again.

Her tits still weren’t purple. I wasn’t sure if I would have wanted to ask her for a kiss anyway at that point. I WANTED to kiss her don’t get me wrong, but I’d have to do it with her mother and sister watching. I had just touched her pussy and bound her tits in front of them, and something about kissing still felt like it would cross the line.

I also just didn’t want to take advantage of her while she was tied up. Rachel could have closed her legs if she had chosen to do so and crawled away on her knees but there wasn’t much she could have done if I wanted to flip her over and have my way with her.

A big part of me wanted to do that! I couldn’t tell you why. If I had to guess, it was because she looked so exposed and vulnerable, and it turned me on. I loved what I was seeing. I’d never heard of bondage or BDSM. It looked so cool and there seemed to be an order to everything. I was just touching the tip of the iceberg!

“Do me next, please” Lori begged. I felt a little guilty like I was cheating on Rachel by offering. Her sister was writhing around on the floor as if she were trying to wallow in the pain. It seemed to me like she was warbling and purring at the same time as if it hurt and felt good all at once but that didn’t make sense to me either.

“What would you like me to do?”

“Oh, you DO like to please,” Lori smiled at me brightly. “I’d love to slap your sweet little fat face. Those chubby cheeks! So cute, like a chipmunk.” she remarked. She didn’t wait for a reply from me. “On the table are some nipple clamps, can you bring them over and I’ll tell you which ones I want.”

I had no idea what a nipple clamp was compared to any other type of clamp. Lori had a laugh about what I showed her initially. Apparently, they were very extreme, heavy gauge steel that served some other purposes.

“I am tough, but I don’t think I can handle that much weight on my nipples. I am not Mom!” Lori said. She seemed so at ease with her sexuality and the fact that I was offering different attachments that could be applied to her nipples.

Doris blushed a little and appeared flattered by Lori’s comments. Eventually, Lori told me to just grab the mouse traps and give her those.

“Are you sure? Your father will want you to wear them for quite a while?”

“Mousetraps?” there was quite an assortment ranging from heavy to small. I’d seen one snap a mouse’s head completely off.

“Yeah, just lift it and clip it, no fuss, no muss,” Lori suggested. I wasn’t quite sure how to do it so that I didn’t snap her titties or touch her actual areola. “Just grab my nipple, pinch and let it snap-on,” Lori said.

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