Babysitting Fantasies Phonesex

Kayla Cumsalot 1844-33-CANDY ext 357
Babysitting fantasies are quite common in my line of work. Older men…young girls…it’s a convenient scenario to make this coupling happen. To be sure, I enjoy indulging them. But I have encountered another angle to this storyline in my real life.
A couple of years ago, I was asked to babysit for the friends of a friend of mine. She couldn’t make it and referred me instead. From the moment I arrived, I had a feeling it would be a unique situation. The mom was more condescending than I liked and I barely got a glimpse of the father before he was in the car waiting on her. She gave me the rundown in excruciating detail like I was the one who was in need of care and finished with telling me what a good boy her son is and how I should make sure he isn’t exposed to anything that would tamper with his angelic soul.

Most moms are overprotective of their boys but her tone just rubbed me the wrong way. It’s not like I was going to pimp him out, for fuck sake! I walked up the stairs and knocked on his bedroom door in the hopes of introducing myself and building a connection. Even though the mother’s attitude was poor, the pay was good, and I didn’t mind getting in the son’s good graces so I could be asked back. I opened the door after hearing his approval and saw pretty much what I expected…skinny boy, glasses, tousled brown hair, reading a book in bed…nerd central.
I quickly ascertained that this youngster was too nice to give me any trouble so I figured it would be a quiet, non-eventful evening. We exchanged pleasantries and I sat on the end of his bed as I asked him questions about his life. He liked sports but wasn’t terribly great at them (shocker) and did very well in school. I was impressed at how mature he was and how easily he carried on a conversation. But I was even more impressed when my eyes slipped lower and landed on a bulge in his shorts that just had to be a function of the material bunching up. It HAD to be, right?
I asked him to show me around the room so he had to get up and I could see if the bulge moved. It didn’t. I heard myself swallow in disbelief as he showed me his baseball pictures on the wall and his baseball card collection in the closet. All the while, I was looking at him in a new way…a way that I knew I shouldn’t…but how in the world could I not?
We heard some boys playing baseball in the field behind his house and I asked him to go over to the window to see if he knew any of them. He said he knew some and that they were better than he was. I walked up behind him and whispered in his ear that there are other things to be good at besides sports.I wrapped my left arm around his chest as my right hand slowly slid down his body until I reached that bulge. He tried to bolt out of my arm as I first made contact but I held him close and told him it was ok as he started to calm down and lean back into me.
I could tell that his conservative upbringing had left him repressed and in need. Not only could I help this young boy…and myself for that matter…but I could pay his mother back by removing that halo from her “perfect” son. I told him to just keep watching those boys play baseball as dusk began to settle in. My hands worked together to slowly slide his belt off and then his shorts. His white briefs came into view and I have to admit finding arousal at that tight, young ass. I slowly eased them down and over his stiffening cock as I undressed him in front of his window. His bedside lamp illuminated us softly as I finally helped him lift his arms and his shirt came off without complaint.
It had been less than an hour and I already had him naked. I hadn’t actually seen his prize yet but my hand found it before my eyes. I moaned into his ear as I felt manhood where there should have been boyhood. I began to softly stroke as I whispered encouragement in his ear. My other hand found his swollen balls and I couldn’t believe their weight. It turns out that he had never actually cum in his young life. Repressed, indeed.
As my strokes grew faster, his cock grew thicker. Instead of resisting, he leaned back into more and let me have my way with him. I knew that if anyone looked up into his bedroom window, they would be able to see him, but that thought only excited me more. I worked him harder…wanting…needing him to explode for me. I wanted that first experience to be with me. I heard him cry out as I felt his large cock twitch in my hand…and then it happened.
Thick, white ropes of cum began to erupt from his pent up cock. I watched in awe as they spurted in the air, landing on his window and the wall next to it. Again and again, he let his loads go…some straight up in the air that landed on my hands. The feeling brought me over the edge as I shook in orgasm behind him. He finally stopped exploding just as I came down off my wave of pleasure and we fell to his floor together as I cradled him in my arms.
It was the beginning of a beautiful friendship.