Chapter 1

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, .

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

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.

The sound of the Andersons coming home stopped us from doing anything else and I was bit relieved because I knew I would feel real guilty if I let Harry break my cherry or take my ass like some biker guy with no mercy. We left the house and were halfway home when Harry pulled over and told me he was going to show me how my sister took it up the ass like a real woman.

That sounded almost like a challenge to me and I wanted to blurt out that I could do anything my

Sister could do and in fact do it better if the truth be known.

Somehow, he got me sideways on the front bench seat and hooked my panties down exposing my tiny rear door to his busy fingers. He probed me, stretched me and eventually got as many as three fingers up inside my sphincter before he started to bounce my sister’s future property on my tiny pucker hard enough to make a fearful believer out of me. I went into a completely submissive mode and simply waited for him to shove the whole thing up deep inside. Of course, he didn’t disappoint me and that is a fact.

I think it was that experience with my brother-in-law’s business pounding my teenaged rear end that I suspected turned me into a “dyed-in-the-wool” bum-humping freak. After that first tingling kinky session, I made every effort to make my bottom presentable for male attentions and everything else was just icing on the cake in my humble opinion.

My last few babysitting jobs were so profitable that I decided to invest into a “butt-shaping” exercise class at the local dance studio. The husband and wife team of dancers were from Brazil and they knew all the little tricks to make one’s cheeks stand tall and proud even when merely walking. Most of the women and the light sprinkling of males were a lot older and a lot stouter than me, but they certainly were serious about getting their buttocks shaped up for the approaching summer.

The husband’s name was “Ricky” and the wife was “Ronnie”. Actually, in my opinion, Ricky had a better bottom than his wife Ronnie. I think I was a bit prejudiced because I had these fantasies of the long, lanky Ricky giving it to me in my rear door from behind to test my determination for shaping up.

I often caught Ronnie giving me a glaring look that promised dire action. if she caught me serving up my flanks for Ricky’s inspection. I knew that look, because my brother-in-law Harry’s former girlfriends threw it in my direction, when he was ogling my bum. I think my sister Veronica had all but eliminated the buggering sessions from her wifely duties with my brother-in-law, due to the fact that she never was comfortable with the necessary submissiveness required for such kinky activities. She was independent-minded and assertive in all her interactions with the other gender and Harry was no exception. I guess my arse was too tempting for my brother-in-law to overlook. There was no doubt; it was constantly readily available for his pleasure, whenever Veronica was busy with other things.

The butt-toning sessions were getting hot and heavy and I found that Ricky was becoming free and easy with his hands and groin on my backside. I would often walk home unsteadily, twisted with the frustration of not getting Ricky’s business up my sweating flanks to stamp me as prime grade “A” arse-pounding material. His wife Ronnie was busy giving special instructions to a buxom blond from the Midlands that involved a lot of slapping and tickling of her jiggly bits with indecent enthusiasm. I found the sight amusing but Ricky was truly pissed at the sight and he pulled me into the locker room with a pulse-racing determination. I didn’t say a word because I knew exactly what he expected of me. Sure enough, I was bent over the wooden bench like some fetish-minded submissive and he pulled my thong to the side and introduced me to his Brazilian home-grown cock of magnificent proportion.

At first, it was more of a rude awakening to the world of anal perfection, but then, the waves of pleasure overwhelmed me completely and I was his plaything with total obedience.

I didn’t see his wife come in and catch us with my arse up high and my fingers in my mouth to keep me from yelling out like some silly schoolgirl being corrected by the master. When I did see her reflection in the full-length mirror, I saw that she was totally naked and wearing an imitation male appendage strapped to her flat tummy. I didn’t know if I wanted to laugh or to cry, but I did neither.

Ricky’s steady humping accelerated rapidly when she mounted his fabulous buttocks and gave him the same treatment that he was dishing out to me. I looked at the three of us in the full-length mirror and it filled me with such heated passion that I felt my liquids flow freely in front and I squirmed vigorously to get Ricky’s beautiful tool a little bit deeper.

The inspired Ronnie started to spank both her husband and me with her vicious palms filling the small room with the sound of meaty smacks and gasps of uncontrollable indignation. She was so good at dishing out the punishment that tears formed in the corners of my eyes and my teardrops wetted the top of the wooden bench.

We all took a shower together after that joyful session and I found that the wife Ronnie was hot-blooded but she was not a vengeful person or one that held a grudge. In fact, right there in front of her own husband, she got down on her knees and licked me to show there were no hard feelings. That was all I needed to decide me to expand my horizon of possible partners to include those of my own sex. It was something I had never considered before, but my eyes were opened to the endless possibilities of spirited coupling behind a locked bedroom door.

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