A Babysitter to Remember - Cover

A Babysitter to Remember

by DevilDog

Copyright© 2005 by DevilDog

Erotica Sex Story: True story of a boy's discovery of what a women really wants

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Consensual   Interracial   Black Female   White Male   Oral Sex   Babysitter   Size   .

I have remembered the summer of my fouteenth year with great fondness on two levels. First my stepsister moved in and second it was the summer I had my first experience with a real woman.

The woman in questions name was Dana and she was a cheerleader at the local high school in her senior year ... I know what you're thinking, a cheerleader, fourteen years old boy YA RIGHT ... well ... It really happened!

It just so happens I am what you would call "extremely" well endowed. To the extent that I had stopped taking showers after gym solely on the fact I was teased endlessly by other boys who "thought" I had a hard on and 10" dick, even soft, can look hard to some. I thought I was abnormal looking after at the dicks around me and just kept myself out of sight.

Being almost 15 I was well beyond the babysitting age however I was hanging out with friends of mine and was asked to spend the night so my parents hired a last minute babysitter for my new step-sister so they could go out on the town for the evening and stay downtown for the night.

As fate turned out my friend got really sick and I was sent home around 10pm.

I opened the front door quietly not wanting to wake anyone when I heard "sexual healing" playing softly in the background ... I almost laughed yet on the couch in my living room was a sight to behold ... my sister's babysitter was on her knees sucking her boyfriend's very small 3 inch cock! She went at it like a woman possessed and I watched until I saw him cumming in her mouth ... I think because she had his whole cock in her mouth with him shoving her head from behind ... she did not look pleased ... She then lay down in front of him and pulled her cheerleader panties aside and asked him to "take care" of her.

He just laughed at her and said that was disgusting and all the guys had told him what a slut she was but if she got him hard again he would consider it ... she started to suck and he did get hard and within seconds he came again but this time all over her uniform! It was then that he started to pull up his jeans with Dana asking "why he had to leave" ... he gave some excuse about homework and getting home too late and getting in trouble and besides they were done right?

I saw it was time to leave so I crept around the corner to my room and shut my door quietly. My cock was as hard as I have ever been and I stripped off my clothes as fast as I could, laid on my bed and proceeded to jack off like crazy ... I was going nuts with the image of her sexy face burned into my mind!

I had both hands around my cock, pumping hard and fast with my eyes shut tight imagining her sucking my dick like I saw! I was about to cum when I heard what sounded like a loud slap and crying coming from the living room.

I pulled on my shorts and ran into the living room to find Dana with her face in her hands sobbing uncontrollably with no sign of her boyfriend. I asked what was wrong. That scared her so much she almost hit me in fright ... I forgot she did not know I was home! I told her the sleepover had ended and I had only been home awhile. She seemed to calm down somewhat and she said I wouldn't understand 'at my age' what was wrong. Dana was still crying and told me that boys are just selfish, she then asked when exactly I had gotten home?

I told her I wasn't sure what I saw that it was kind of dark and had gone straight to bed ... and it was at this point I noticed her eyes where fixed on my boxer shorts ... I was still completely hard and it looked almost comic like in appearance tenting out like a light pole! My eyes adjusted to the light and I was mesmerized by what I saw, this was by far the most beautiful woman to that date I have ever laid eyes on ... sex, long, black luxurious hair, dark green eyes, flawless mocha complexion and to top it off pouting, thick gloss covered light flesh colored lips and not to forget a body most playboy bunnies have to purchase to look that pretty ... her breasts were what I would say now a 38dd and 5'6" of perfection however that hourglass figure till this day has never been repeated by any woman I have ever laid eyes on ... I just stared at this girl!

I came out of my staring trance when I realized she had just asked me a question "What made you so hard little Steven?"

"I get hard when I see a pretty girl." and I just kept staring at her like a dumbass!

She reached her hand over and lightly touched my cock with her well manicured fingers while her right hand touched the back of my head guiding me to her now uncovered breast.

I was face to face with the first truly mature bare breast I had ever seen up-close and I was savoring every second!

As she guided me to her hard nipple, I sucked for all I was worth. Dana giggled telling me to be gentle and not to suck so hard ... I adjusted and continued while her hand stroked my dick ... it was then I heard a gasp "this is the largest cock I have ever seen ... ever. I want to fuck you but first I have to do something..." with that she slid down and engulfed the head of my cock in her hot little mouth and then she tried to put it in her throat with no luck as her gag reflex was in full effect. She kept at it and soon had me to where I could not hold back "I am Cumming...!" She just held me in her mouth and drank me down like crazy.

 
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