Bobby The Babysitter, a short story by harrylime

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.
My Ronnie told me we had to kiss to seal the deal. I wanted to know what ever happened to just shaking hands like friends. She told me that since we were almost brother and sister it had to be something more personal and kissing seemed like a good choice. I could see the logic of that and she insisted on putting on a thick layer of lipstick before we locked lips. I was pleasantly surprised because she didn’t make any attempt to keep my tongue out of her mouth like most girls do for the first time. In fact, before I knew it, she was deep inside my mouth with her tongue making me beg for mercy as I was having trouble breathing. She just laughed and told me I was being more like a girl than a boy and that got me so mad that I kissed her so hard that she started to shake like she was having some kind of fit and she got up on my lap and bounced like a little girl with a friendly Uncle from out of town. My cock was pretty aroused now and I was certain she was getting the brunt of it in her female place. After she went through a short period of having some shakes, she shook my hand and told me we had a deal and that she would set it up for me. I just hoped she would keep our kissing session a secret from Trudi because I was still on a promise and hoping for some quite action.
The Adams family was small.
There were only the parents, Dominick and Louise and their little daughter Amanda who was only eleven years old. I had seen Amanda in school and she was a nice kid with braces and had not even a hint of breast development as yet. I figured she was not into guys yet so there were no problems with her trying to get me in trouble doing my babysitting duties.
Mister Adams was on the heavy side and I figured it was because he worked in an office and rarely did any exercise. They had the child within a year of getting married and I suspected that was the reason they got married in the first place because they really seemed ill suited to each other. Dominick was a sort of a prick with a sarcastic remark for anyone and everything. He was always sniffing after other female’s bottoms like some wild dog sowing his wild oats. On the other hand, his wife, Louise was a real “goody two shoes” who was into the church activities and the choir and she was constantly quoting the Bible to make a point about things she managed to have an opinion about even if she had no experience with the subject.
Normally, that sort of attitude would turn me off because I was a sort of scientific or logical person and didn’t set store in agendas that were set up just because of someone’s bias or personal preference. In Louise’s case however, I could adjust to her way of thinking because she had the prettiest bum I had ever seen inside a tight skirt in my entire life. Just looking at her lovely “shelf” when she stood up and the heart-shaped hour-glass figure when she bent over to say “goodnight “ to her daughter was enough to give me a super hard-on and make me wish I was her husband and could do it to her each and every night.
Actually, old Dominick seemed like he had lost interest in his wife. It was difficult for me to judge because I had not seen how he had handled their relationship previously. Still, it was noticeable that he never ogled her body when she was squatting down to pick up the car keys that she had dropped inadvertently when she picked them up off the hallway table.
They were a bit overdue but I was just finishing my homework when they came in the front door. I immediately jumped up to help because Mister Adams was totally drunk and almost unable to stand or walk a straight line. Louise and I managed to get him into the upstairs master bedroom without waking up the daughter. I helped her remove his shoes and belt and assisted her to pull his trousers down revealing a very limp dick and a pot belly covered with lots of hair. We went downstairs and she told me that she would probably sleep on the downstairs sofa because he would snore all night and toss and turn. I stupidly asked her,
“But what if he wants to, you know, do something and you are not there to give him what he wants?”
Louise laughed and told me,
“Honey, his cock hasn’t gotten hard from the first year we were married and I don’t expect it to get any better any time soon. I usually just use my battery operated boyfriend to help me go to sleep at night. Unfortunately, I left it upstairs and I have no intention of going back upstairs and retrieve it now.”
She had just made up the sheets and pillows on the sofa and was bent over right in front of me and before knew what I was doing, I had both hands up her skirt and was spreading open her cheeks to give me ready access to her pretty cunt and even sweeter brown eye. We fooled around for some time but I managed to make her wet at least two times and I knew she was having a good time even before I got my cock out and into firing position.
I did the Mrs. at least a half dozen times in the next couple of hours. I vividly remember managing to cram my dick up her bum the last time and listened to her squeal each time I punished her bottom with my greedy cock. I thought I heard a noise on the stairs but when I looked there was nobody there. The first load that I put in her pussy was so creamy that it constantly leaked out the remainder of the night. She told me that she had not had that much juice inside her ever before. A couple of times, when I was flagging behind her needs, she whipped up my erection with her skilled tongue making me spill more of my seeds inside her topping her off like a road racer in a race to the finish line.
It was the next day that we both discovered her daughter had taken shots of me pumping away on a very naked MILF backside with both of our faces up high and proud in the throes of ecstasy.
That was my crime in a nutshell and the headline said it all,
“BOY BABYSITTER RAPED BY DEACONESS MOM IN FIT OF LUST AND ILLICIT SEX”