Diary of a Submissive Babysitter
Chapter 1

Copyright© 2012 by harry lime

Babysitter Sex Story: Chapter 1 - Amy just turned 17 and is embarking on a new babysitter business. She has her backup sitter, Sally, to help her when she has excess customers. In the absence of current boyfriends, Amy becomes very close to Sally and decides maybe she doesn't need as much cock as she thought she did. The babysitting jobs turn out to be a lot more interesting than she ever thought they could. Her diary is an erotic account of all her new adventures.

Caution: This Babysitter Sex Story contains strong sexual content, including Ma/ft   Fa/ft   Mult   Consensual   Lesbian   BiSexual   Heterosexual   Fiction   Spanking   Humiliation   Group Sex   First   Oral Sex   Anal Sex   Masturbation   Petting   Squirting   Cream Pie   Exhibitionism   Voyeurism   Teacher/Student   Babysitter   Clergy   School  

August 14 ... Today is a very happy day for me. I am finally 17 years old and I will be allowed to stay out until midnight and even start my babysitting business without parental interference. I am starting this new diary today to keep track of all my customers and as a tool to help me be a better babysitter. My old diary is filled with a lot of junk about boyfriends, real and imagined, and the petty problems experienced in high school. I still have another year to go in high school but I could have graduated early if I wanted to because all of my work in the last year was at the university level. I just didn't want to rush things and I felt a little too immature for the university crowd.

I should insert a quick run-down on my particulars before making any more entries in this book.

My name is Amanda Johnson. Most of my friends at school call me "Amy" for short. I have not had very many boyfriends. I guess you could count them all on one hand. I don't have one right now, because I am still pissed at my last boyfriend Peter, whom I caught humping that slut Tiffany Jones under the football bleachers. Lately, I think most boys are just looking to get into any girl's pants to see how tight their pussy really is. Not that I mind that much because I like getting humped too. It just seems so immature to me now. I don't mind giving up my pussy or ass, but I don't like being made a fool of.

I am a short girl, sort of on the "petite" side, and I tend to be quite slender because I have a high rate of metabolism that disposes of the junk food I like to stick in my mouth.

I have not had too much experience with actual fucking because it is hard to find either the right place or even the right guy for that matter. However, I have had extensive exposure to oral gratification of boys ever since I was initiated to sucking cock at my sweet sixteen party and the taste of various cocks never failed to make my female juices flow like a river.

In all honesty, I must admit I have never had a cock inserted right into my brown eye but like to have one sliding in my ass crack making me feel like a very bad girl. My boobs are not much worth mentioning, at least in my opinion, but some of my boyfriends got off by sucking them and playing rough with my nipples. I kind of liked it but just didn't understand why they would enjoy that sort of thing when I was available for a quick cock sucking or playing with my ass or pussy.

I tend to take most things at face value and try my best not to lie to my friends about anything. I guess I have always been pretty submissive and like to take orders instead of giving them. I fantasize about being made to take it in the ass by an older, big strong guy who treats me rough and forces me to do a lot of kinky sex things with a very firm hand. I really love to be humiliated that way in private in a role-playing way. Sometimes I think about being spanked really hard by a uniformed policeman for being a bad girl and made to suck his cock after he spanked me.

I wonder if I will ever get that chance someday.

August 17 ... I got Sally Randell to be my backup for the babysitting business. Sally is only 16 and a year behind me in school but we are real good friends ever since she went with me and my mom on a swimsuit shopping trip to the mall last month. We were giggling like stupid schoolgirls in the changing room and grabbing each other's goodies making me very excited and wanting my pussy taken care of. My mom was all tied up gabbing with the manager and I spread my legs for Sally to shove her head between them to lick my greedy pussy. She seemed to enjoy it so much that I started letting her do it on a regular basis ever since, even though it was not quite the same as a nice long cock. I began to think that maybe I was a lesbian or something, because Sally's tongue in my mouth made me hot as a firecracker and ready for getting my pussy stretched real nice. She admitted to me she was still a virgin and only sucked guys off just to keep her real pussy-loving agenda a secret. We agreed that I would get 20% of her backup money and I would give her some of the prime Friday night business when the parents always came home late and had to pay overtime.

August 18 ... I lined up 2 jobs tonight. I gave the easy one to Sally because she was really cute eating my pussy right after school ended on Friday. I knew she wanted me to do the same for her, but I was not ready yet to commit to a girl/girl relationship just yet. I took the more difficult job over in the ritzy part of town where the houses were a lot bigger and the yards had high fences and gates. Mitzi and Floyd Anderson were a typical power couple with lots of money and a precocious 2 year old girl who made their life a living hell. I let little Annie know right away who was boss and she sat at my feet until it was time for bed. I tucked her in and she asked me to give her a good night kiss. It was kind of sweet and I figured she didn't get much attention when there were no servants or babysitters around.

When the Andersons came home late, I was starting to drop off on the soft leather sofa. I had some of the dirty Japanese comic books that made me horny as hell and hid them under my waist band so I was not thought to be a perverted young girl. Mrs. Anderson, I guess I should say Mitzi was really soused from too many martinis and Mr. Anderson was none too happy about it. He put his finger to his lips to signal me to keep quiet and led her unsteadily up the stairs to their bedroom. When Floyd came back into the living room, he told me they were celebrating his promotion to district manager with a large increase in pay and other perks. He was standing over me and I looked up into his eyes and saw they were undressing me with raw desire. My pussy started to leak big time and then I noticed that his trousers were bulged out with a huge erection. I leaned forward and kissed the outline with some gentle little baby kisses like a bad girl with no control over her emotions.

He told me to stand up and bend over the end of the sofa and I obeyed his orders without hesitation.

When he pulled down my panties, I knew he was going to make me do it. The touch of his cock on my pussy slit was like a jolt of electric current shocking me into a juicy orgasm. I looked over my shoulder wanting to ask him to "go slow" because I knew my pussy was tight from non-use. Right then, he shoved it in all the way and gave it to me hard just the way I dreamed about getting it. I bit my thumb because I didn't want Mitzi to wake up with my shouting and have her catch us fucking in the living room.

Floyd pounded my slender teen-aged ass pretty hard. It was a lot different having a full-grown mature man giving it to me back there. My ass cheeks were bouncing and I could hear the slap ... slap ... slap of his meat hitting the back of my legs. I think I had 3 orgasms before he was ready to shoot his stuff. Just before his shot his load, he pulled out and put his cock right on my face and let his cream hit me full blast all over my face. I had to shut my eyes so I wouldn't get the juice in my eyes. It was a first for me and it made me feel deliciously dirty.

I stayed bent over and the cum was dripping off my face when we both heard his wife call out from the top of the stairs. I pulled up my panties real quick and he gave me a towel from his golf bag to wipe off the sticky stuff from my face.

Mitzi came in and asked,

"Did you give it to her yet, dear?"

I looked at her with a blank expression and kept my mouth shut.

At first Floyd looked guilty as all get out, but then, he smiled and said,

"We have to give her extra for being late, honey bun!"

He took a hundred dollar bill from his wallet and pressed it into my palm, telling me,

"You did a great job, Amy. We will want to use you again next week, if you are free."

I thanked the Andersons and promised to be on time next Friday night. I wondered what Floyd would want me to do the next time. I had all week to think about it.

August 19 ... Sally stayed over at my house after we finished our short babysitting jobs this evening. We both finished up well before midnight and my parents were already asleep when we silently climbed the stairs to my bedroom.

I gave Sally the bottoms of my "Hello Kitty" pajamas and I wore the top.

I told Sally we had to be quiet and not wake up my parents. She buried her face in my pussy and I had to put a pillow over my face to keep my groans muffled and low. It was so cute the way that she even went all the way back to my brown eye and licked it like a lollipop. When she did that, I felt so close to her, more than any other person in the whole wide world.

When I told her about Mr. Anderson, she masturbated her pussy and twisted her nipple until she fell face down in a happy orgasm. She asked me if it "hurt" to take a man's cock into a pussy slit as tight and inexperienced as hers. I told her that it did hurt for a little while but then it just "loosened up" and seemed real natural. I warned her about the guys that wanted to do it in her rear door because until she was real ready for ass fucking, it was not a good idea to open up that entrance for guy's cocks.

I was so grateful for the way Sally took care of my pussy and ass, that I finally broke down and licked a pussy for the very first time. It was so different than sucking a cock. I found that my greatest pleasure was in giving pleasure to Sally with my busy little tongue. I had to keep my hand hard over her mouth or we would have been found out for sure. She told me later that my hand on her mouth was the best thing of all and it made her feel like she had to come for me gushing her female juices. It certainly was not the same as giving up one of my holes for a cock but I liked the feeling of making Sally feel good.

August 22 ... I decided that I would put in any unusual things about my doing stuff with guys or even girls that got real close to me, like Sally. I won't bore anyone with the normal stuff like spreading my legs for guys or giving out freebie blowjobs. But special things that I did for the first time or that made me feel real good I will put in this diary.

Today at lunch was one of those special times.

I had to go to the registrar's office to fill out some background information for some of the college applications. The guy who was working for the application service was really good looking. He was kind of dark and with a name like Carmine Antonelli, I figured him to be Italian. He was in his late 20s and had a little wisp of hair that kept falling down onto his forehead. The slight stubble on his chin looked so macho and masculine that my pussy started to leak even before I sat down across from him. He asked me if I would be living on campus and if I minded being in a coed dorm. I joked with him and said coed was just fine with me because I planned on having a lot of social interaction in college. He told me that was fine but I had to be careful about family planning. I jokingly said that was easily solved by "taking it up the ass" because no girl ever got pregnant that way. He asked me if I wanted to give it a try to see if I liked it and I nodded my head yes. I was really scared because I had never taken a cock inside my brown eye before but I didn't want this good-looking guy to know I was a novice.

He slipped the bolt on the door and closed the blind on the window.

When he pushed me face down over the desk, all I could see was reflection of my quivering body in the mirror on the side wall. My ass was bare because he had already pulled my panties down to my ankles and his cock looked so huge; my knees started shaking in anticipation of being skewered like a bug on a pin. We didn't have any lube, so he told me to spit in his hand and he rubbed my saliva all over his hard cock pushing it right up against my tiny anus. My juices were dripping down the insides of my legs and I hoped he didn't see just how perverted I was waiting for my anal impalement. My muscles gave way and he took up residence just inside my rectum and waited for me to adapt to the stretching of my sphincter. I looked over my shoulder and told him to put it all the way up inside and give it to me nice and hard. It was so very strange being fucked like that. At first, I was certain I did not want to do it again, but after a bit of pounding, I started to really like it and rolled my hips trying to get him to go deeper. I don't remember what I said to Mr. Antonelli, but I know I used the word "fuck" an awful lot. When he shot his load, it felt wonderful up deep inside my gut and I giggled when he pulled out with a little popping noise and I let go an embarrassing noisy explosion of gas that made us both laugh. I promised him I would consult him about my school decision real soon and we exchanged telephone numbers. It was too bad he was already married.

I hope you liked a week from my diary; I will be making weekly reports about my activities and my adventures in babysitting.



Chapter 2 »