Bobby the Babysitter


Caution: This Erotic Sex Story contains strong sexual content, including mt/Fa, Teenagers, Consensual, Heterosexual, Fiction, Slut Wife, Incest, Brother, Sister, First, Oral Sex, Anal Sex, Masturbation, Petting, Cream Pie, Voyeurism, Size, .

Desc: Erotic Sex Story: It was certainly not normal to have a male babysitter on the job. Bit of a role reversal for everyone involved.

My name is Bobby Brown and I am really just a normal teenage boy with no sense of kinkiness or deviancy hidden deep inside. I know the newspapers and the court system say otherwise but I can assure with utmost sincerity that I am not that kind of person. My mom and my stepdad have pretty much thrown up their hands and shoved me into the "return to sender" slot at our happy little home not wanting to face up to the accusations that their son is some kind or pervert. My sister Ronnie thinks it is all very funny but she always did have a weird sense of humor.

I should state right up front that I am already sixteen and in fact will be seventeen at the start of next month. That makes me old enough to have consensual sex pretty much everywhere but not old enough to be legally independent without my parent's permission. I hasten to add that before the unfortunate incident of the so-called "Halloween Babysitter Affair", I was technically a virgin having never fully inserted my cock into any female happy place and filling her with my untested male juice. I had a chance just after my sixteenth birthday party with my sister's best friend Trudi who had a pair of boobs that defied gravity despite their fully rounded size and shape. I had played with them before and I noticed she did have a lot of fun letting me fondle, lick and suck on them like she was my mama and I was her little baby boy.

She even said things like,

"Don't bite mommy's nipple, you little brute!"

I figured she was into some sort of fetish type thing and was hung up on her breasts being pleasured in different ways. I didn't care because she was being quite generous in allowing me full use of them for my own enjoyment and I really appreciated it far more than she knew. Things progressed accordingly and before we knew it, we were on top of my sister's bed with her knickers down and my middle finger was frantically pumping her wet slit with vigorous authority making her pant like one of the girls on the sex videos that we boys watched in the basement of the church when the priest was upstairs hearing confessions. I had wondered when I watched those things if the girls were just faking it to make the men think she was enjoying it when she really was not having a good time at all.

Now that I saw Trudi almost fainting and out of breath from just my finger and not my cock, I accepted that they were probably not faking their frenzied orgasm.

Trudi told me to put my cock right in her crack and I wondered if she was thinking about actually taking me inside her bum like some slapper on the street corner. But she told me to spit and get it wet to slide on the outside and after a bit of laughing and fumbling around, I gave her my load all over her pretty tank top and all up and down her back and plump rounded cheeks. My sister came in just as we finished and she was pissed that I had "done it" to her best friend. Trudi explained that we were just fooling around had done nothing that could be construed as actual sex in any sense of the word. My sister was acting real unconvinced but I knew her pretty good and I could tell she was just jerking Trudi's chain to make her do her a favor later on to make up for her "slutty" behavior with her younger brother.

Anyway, she was on a promise to actually "do it" the next time and I was certain she would give it up without much difficulty judging from the way she put some of my juice on her finger and licked it off with her tongue to get the taste for next time. I didn't like the way my silly sister was looking at my dripping cock so I quickly shoved it inside my briefs and got out of her room before I got into real trouble. We were not blood-related brother and sister as her father had married my mom after my real dad had been killed in service in the Middle East. Still, we were legally brother and sister and I didn't think she should be looking at my cock like that. Besides, she had a boyfriend of her own even if he did have a bit of a "pencil dick" and I think he was scoping out bent boys as well. I steered well clear of him and he whispered in my ear one late night,

"Don't worry, Bobby boy, you're not my type. I like boys with a little bit of meat on them not fly-weights like you."

I was tempted to warn my sister off but she seemed old enough to make her own decisions and I was certain she had already let him shove his thing up her bum in the back yard when my parents were out on a dinner date. Her groans were so obscene that I had to rub one out on top of my bed hearing her wails of distress waft up from the patio.

My trouble really started when my stepfather lost his job to redundancy and the household income dropped considerably robbing my sister and me of funds for things like movies and snacks at the shopping mall. My sister started doing babysitting to have extra money and she sometimes lent me some money so I would have fun as well. I was in debt to her for the financial transfers with little chance of ever paying her back when she approached me to fill in for her at a babysitting job just a few streets over with a new couple that had just joined our church.

My first reaction was to say,

"Fuck no, I am a boy and boys don't ever fucking do babysitting!"

She told me she would wipe out my debt and let me keep the payment for the three hours' work and I could probably do my homework at the same time. It sounded like a win-win scenario to me and without any further discussion, I accepted providing she promised not to tell any of her girlfriends, especially not Trudi, that I was doing an actual babysitting job.

.... There is more of this story ...

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