Bobby the Babysitter Revisited - Cover

Bobby the Babysitter Revisited

Copyright© 2014 by harry lime

Chapter 4

Erotic Sex Story: Chapter 4 - Bobby is not quite up to his babysitting tricks in this story but has lots of interaction with his not-really-a-sister Ronnie as well as her best friend Trudi who is ready to fulfill her promise for complete submission.

Caution: This Erotic Sex Story contains strong sexual content, including mt/Fa   Mult   Teenagers   Consensual   Heterosexual   Fiction   Incest   Brother   Sister   Spanking   Group Sex   First   Oral Sex   Anal Sex   Masturbation   Petting   Cream Pie   Exhibitionism   Voyeurism   Size   Teacher/Student   Babysitter  

Mrs. Cummings my homeroom teacher dropped a detention slip on my desk without saying a single word. I knew she was entirely justified in the punishment because of the shameful way I kept falling asleep in her classroom like I had some sort of medical condition.

I couldn’t explain that my exhausted physical state was the result of a tiring weekend of babysitting duties with the new couple from Colorado that seemed more interested in mountain climbing than in raising their small daughter. Susan was a precocious tween on the verge of budding nobility. She was the shyest child I had ever met and seldom opened her mouth except to say “thank you” or “I’m sorry”.

Her mom was an entirely different story.

Vera Golightly was definitely the one that wore the pants in the family and she had the muscles that confirmed her dominance over her bookkeeping husband Mark.

Mister Golightly was sort of small and slender and wore glasses but he was a nice guy with a smile for everything even when Vera was prodding him with her constant nagging and ass-pinching motivational inspiration. I bet he was the one that changed Susan’s diapers most of the time when she was just a little tyke barely able to navigate on her own. I was respectful of Mrs. Golightly because I was a football player and spent a lot of time in the weight-room so I knew how much effort Vera had put into her muscular development and recognized all the hard work she had done to get lean and tough.

That first night of babysitting, she had challenged me to a wrestling match right there on the fluffy white carpet in the den and I thought she was joking and discovered she was not the type to joke about wrestling because it was a sort of fetish with her. I saw Mister Golightly look at me with pity in his eyes and I knew right away I was not going to win this match no matter how hard I tried or even cheated to come out on top.

I knew right away that Vera was not a woman who ever lost a contest or finished on the bottom of anything.

Susan put away her homework and gave us her full attention pulling her long blonde hair back into a pony-tail and letting it stick up like a stiff bun in the back. She looked real cute sitting there in her “Hello Kitty” pajamas and her fast-developing breast was evident under the close fitting fabric. I quickly looked away because the last thing I wanted was to get involved with a twelve year old, even if I was still officially a minor as well. It was a lot safer to stick with the married moms and in all honesty they needed some up close and personal attention a whole lot more than one of the under-age pretty young things that still had their cherry intact.

I was surprised when Vera stripped down to her undies and told me to do the same. I was a bit nervous standing there in my jockey shorts trying to keep my eyes off Mrs. Golightly’s camel toe that was prominent enough to advertise the fact she shaved down below. I could see Susan giggling at my nervous frame of mind and I suspected her hand was busy under the throw covering her bare legs from the chill of the air conditioning unit right over the sofa.

I looked at Mrs. Golightly and all I could see were her nipples pushing stiffly against her running bra like soldiers at attention. We wrapped our arms around each other and I was glad she didn’t insist on starting from a crouched over all fours position. I had no doubt I would be the one on the bottom in such a situation and unable to forestall her easy win by simply riding me down prone on the fluffy white carpet and twisting my arms or legs until I surrendered to her will.

Of course, I lost that match and sent Susan to bed and her husband to go with her to read her “A story from the Bible book”. She motioned me to sit on the sofa and I was mortified because all I had on was my jockey shorts. The fact that I was sporting a terrible erection was so embarrassing that I didn’t even try to hide it from her and just hoped it wouldn’t pop out like some wayward cowlick just before a photo session. She was sweating heavily from the exertion of pinning me to the floor and wrapped the towel around her neck to catch the perspiration before it got her bra soaking wet and easy to see right through.

Vera plopped right down next to me and I could feel her wet thigh on my leg like a hot poker ready to brand me as her property. Her camel-toe was blinking signals in Morse code, but I never could understand that stuff even back in the boy scouts.

At this point, I was a bit confused and what to do about Mrs. Golightly.

She was not the sort of married woman I liked to bend over a sofa or cuddle between my knees whilst she showed me her oral skills. In fact, she scared me a bit and I didn’t like that because it was my belief that no male should ever be afraid of a woman unless she had a gun in her hand.

Vera scared the hell out of me because I sensed she was unpredictable and that deep down inside she truly hated most men, myself included, and was ashamed of the fact she just had to have what they all were issued at birth unlike the females of the species. Once she had her strong hands on my family jewels, I knew enough to let her take charge because she was generally pretty single-minded about getting down to business and almost running to the finish line like a sprint instead of a marathon.

It was no different this time.

She stuffed me inside without ceremony and got on top with that smile of hers that told me I better not wilt until she got what she needed. It was almost enough to make me fail her kinky performance test, but my sturdy “peter” took care of business with a determination that I was not sharing way down deep in my gut. My gut was telling me that Vera was a dangerous female and not the kind of woman a punk like me should be fooling around with because it was like playing with fire.

I wanted to escape her arms but she tucked me under her stronger body and spooned me like I was the girl and she was the guy getting his jollies. It was downright humiliating and the touch of her hands all over my backside was downright degrading. I felt a bit cheap and used just like most of the girls I had diddled with little thought about their personal feelings. I guess I was experiencing some regrets at my shameful actions now that I was on the receiving end.

Still, I just nodded my head in agreement when Mrs. Golightly told me the next morning,

“Be here Friday night, Bobby, I am going to have a couple of my girlfriends from the gym over for drinks and I want to show them how easy it is to pin you to the carpet.”

That thought haunted me for the entire next day and I guess it what was causing me to drop off in Mrs. Cummings classroom.

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