The Babysitter's Brother-in-law - Cover

The Babysitter's Brother-in-law

Copyright© 2016 by harry lime

Chapter 1

Erotica Sex Story: Chapter 1 - Being a babysitter is a profitable business. This babysitter likes the perks even better than the cash.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Teenagers   Consensual   BiSexual   Heterosexual   Fiction   Cheating   InLaws   Spanking   Humiliation   Group Sex   First   Oral Sex   Anal Sex   Masturbation   Petting   Sex Toys   Squirting   Voyeurism   Size   Babysitter   Public Sex   Workplace   Nudism  

I hated to advertise the fact that my only source of income was from my earnings as a babysitter. My key to success was my reputation of being willing to take any job on extremely short notice. My parents were totally on board with my business venture, because they were a little bit on the stingy side, when it came to financing my trips to the mall or paying for my fetish of a caramel cappuccino every day like clockwork after school.

Not that I was loose with my money.

In fact, just the opposite was true. I guess my thrifty attitude was in the genes and I was a mini-replica of my penny-pinching parents.

My sister Veronica was just the opposite. She was constantly borrowing money from me with the promise of paying me back. I knew she had no intention of ever doing that but I didn’t mind too much because she helped me with my homework and gave me all the inside scoop on how to make a boy happy. I was a bit of a nerd when it came to mingling with the opposite sex and she supplied me with a couple of her boyfriends to demonstrate the workings of a real live cock like a practical application lesson to learn a scientific fact. We had a lot of fun with those willing pricks eager to show me the fastest way to drain their pent-up spunk. I got a lot of “hands-on” experience with manipulating the things into doing their duty. I was initially reluctant to get into the mechanics of using my mouth and lips to pleasure her willing boyfriends. Then, the sight of her obvious enjoyment with the gross things sliding into her mouth was enough to induce me to imitate her technique.

My sister was now engaged to be married in the spring. I thought it was too young for her to get married, but not too young to have sex with as many boys as possible. I was in no position to be critical because other than learning how to use my hand and my mouth at my sister’s kind tutoring, I had no experience below the waistline. That was sort of not normal for an eighteen year old senior with a great body and a willing attitude.

I expect you might want to laugh when I describe my body as “great”.

Just a few years back, I would have hesitated to make that claim, because I still had the vestiges of baby fat and my disastrous braces put a serious kink in my kinky use of my mouth and tongue in making male friends out of the sight of others. All of that was gone now and I had emerged as a veritable swan from my “ugly duckling” childhood. It had gotten to the point that even my uncle Vincent wanted to allow me to taste his manhood. Up to that point, he had basically ignored me, even when I romped around the living room in nothing but my training bra and “Hello Kitty” knickers. I used my babysitting money to purchase some risqué French undies and would “accidently” display them, when I wanted some young lad to beg for an “on your knees” performance in the boy’s bathroom. I sort of drew the line at teachers, because most of them were married and they all had a horrible reputation for “falling in love” with the hot little teenagers under their control. I certainly didn’t mind dishing out the odd oral session here and there, but the thought of being young and hot for passion in an old man’s hovel was definitely not on my agenda.


Veronica was almost twenty and anxious to have her first baby with her steady boyfriend Harry after a few years of doing everything possible to avoid just that. She had even taken it up her backside more often than not whenever they did not have a condom available to forestall the chance of an unwanted pregnancy. She told me that it was a bit painful at first, but she soon adapted to the terrible stretching and now took it all the way up with little difficulty. That was surprising because Harry’s cock was oversized and thick as a metal pipe right down to the very tip. She let me watch her take it in her pucker hole one afternoon just for kicks and I could not get the image of the unnatural sight out of my impressionable mind. I vowed that I would never let a man do such a nasty thing to me because it seemed about the grossest thing in the entire world.

With Veronica’s permission, I gave her future husband Harry my best oral sex to see if I passed the grade of being an accomplished cock-sucker. Harry gave me an “excellent” grade and I could see that Veronica was a bit jealous that he seemed so pleased. I decided that any future explorations with Harry would not be in my sister’s presence because she could be a vindictive person when her chain was pulled.

The weekend before the wedding, I took a job with the Andersons over on Lakeshore Drive. It was an easy assignment because their young daughter Nancy generally slept the entire night without any trouble. They called and told me that they would be held up a bit later than usual at the dance and I informed Harry and Veronica I would be late coming home from the job. Usually, Harry would pick me up because I had some trouble with some of the husbands getting fresh with me in the car on the way home. I did my best to keep it on the hush-hush because I didn’t want my parents putting the kibosh on my only way to earn money before graduating from high school.

Harry came over to be there when they returned to whisk me back to the relative safety of my parent’s home. I was glad he was coming and planned to give him a nice “on my knees” performance before the Anderson’s returned. I just had to be careful that young Nancy was sound asleep and tell Harry to keep the noise down to avoid any trouble. It might be the last chance we had to “do it” before the wedding. I knew that after the wedding, I would be real guilty about putting out to Harry without my sister’s permission and I felt reasonably certain she was not inclined to be so generous with her new spouse’s tool of creation.

We barely made it back to the living room and the soft sofa cushions.

Harry’s thing was tickling the back of my throat with determined explorations and I had my fingers pushed up in his heated crack showing him how it felt to have his sphincter messed with when he was humping a young girl’s mouth. He didn’t seem to be disturbed by my liberties and after I managed to get my middle finger buried up to the hilt, he rewarded me with his full load of pent-up boy-juice in generous brother-in-law fashion.

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