My Babysitter

I could feel the warm cock in my mouth, it throbbing between my lips. It tasted so good I never wanted it to end. Of course it did, however. Just like every other morning I awoke my fantastic dream to my bed with my hand in my pants, partly dissatisfied because I had another homoerotic dream, and partly dissatisfied because it wasn't real. I really liked the idea of sucking a big juicy dick, but I didn't like the idea of making love to a man. It seemed so disguising to unreal to me, that I would never do it.

I went downstairs with my dad barking at me, as usual. "You're 21 years old, when are you gonna learn to behave yourself?!" My dad was referring to the night before, I was brought home by the police saying they found me drunken on the streets and they said I needed a ride home. Since my dad was on the police force, the cops always cut me breaks. But he gets so embarrassed when his buddies have to drag his son home, so I always get in huge trouble.

"Your mother is leaving to one of her business meetings in Hawaii next weekend, so I'm going with her to have a vacation after the meeting. And now I don't know what to do with you!" my dad said. I knew what was coming next. Since he was a cop, he uses a different form of punishment he knows will change my ways usually. He tries to punish me in the most embarrassing ways, and it works alright. "Since you embarrassed me incredibly bad this time, I think I know what I can do to get you equally as embarrassed as I am." I didn't know what was coming next, but I knew it would be bad. "I'm calling your old baby sitter and having her watch you the whole week while we're gone." My heart skipped a beat.

"Annabelle? No! This can't happen! How do you even know she still lives nearby?!" I shouted.

"Well I guess we're about to find out," he said, picking up his phone. A couple minutes later, he already got it settled. "She seemed really excited to be in on this," my dad said. That was it. There goes a whole week I could have spent in my underwear, doing nothing. "We're leaving in two days, maybe you'll learn your lesson then. A whole week with Annabelle, Sam."

I spent the next day just thinking about my old babysitter. I had her from when I was about 6 to when I was 12. She was 7 years older than me, so now she's about 28. I got to thinking about it, and she was a nice babysitter. She would always play my boyish video games with me and play outside without worrying about a nail or her hair being ruined. She was very attractive, as I remember. She had long red hair, freckles, a nice petite body, and a cute smile on her face all the time.

The days passed and finally it was monday, the day Annabelle would come over. My parents left, reminding me of how embarrassing having a babysitter would be and all of that, but I was looking forward to it, actually. My parents left as soon as Annabelle came over, and she looked just a great as I remembered her, just you could tell she was a couple years older, she had grown to be about average size for a girl, in no ways was she thick though. We had a good day, although it was a bit awkward, we sat and talked and watched movies, and finally we went to bed. She slept in my parents bed across the hall.

My reoccurring dream I have about sucking on the sweet juicy cock was intensified this night, I took it in deeper than usual. I was awoken by Annabelle's friendly face. "Rise and shine, sleepyhead, we have a lot to do today!" she joyously said.

"Like what?" I grumbled.

"I thought today we'd go to the park!" she cheered.

We went to the park and she made sandwiches, it wasn't even embarrassing like I had expected, it was kind of like she was my girlfriend or something, but more like a guy-friend, because she threw the football with me and it was a great time.

When we got home, we were both incredibly tired and we decided to watch a movie. The entire time the movie was playing, I was so scared. I kept thinking about how beautiful Annabelle is and how much I would love to be with her. At the end of the movie, I said "Y'know, my parents meant this to be a punishment, but you're actually really fun."

"And you're sweet." she said, "How about a couple of drinks?"

"I've never considered drinking with my babysitter, but what the hell!" I exclaimed.

As the night grew deeper and deeper away from midnight and towards morning, we got more and more in tune with each other. We kept making eyes at each other and finally it happened. I kissed my babysitter right on her lips. It was better than I expected. She slid her tongue deep into my mouth and I began rubbing her back. I moved my hands to her chest and began massaging her breasts.

"That feels heavenly" she moaned, as she began to rub my thighs.

There was my childhood voice inside my head telling me not to do it, but I felt I had to. Her body seemed so perfect to me.

I began to rub the inside of her thighs and she took off my shirt. "Bow wow! Nice chest," she said.

"Same to you" I joked back. I ripped off her shirt and exposed her pink, lacy bra with a little bow on it. I popped it off and there they hung: the most exquisite breasts I've ever laid eyes on. I send my face between them, and began to suck on her nipples while she moaned.

I began to let my hands explore her body and finally I moved my hands back down to her waist. I began to unbutton her pants and suddenly Annabelle looked panicked. "N-n-no... wait" she said.

"Why? Whats wrong?" I replied.

"It's just.... no we can't do this. I gotta stop" Annabelle muttered.

"Come on, what could be wrong?" I say as I begin to unzip her pants.

After I unzip it, it is apparent. She has a tiny bulge in her pants.

"You'll think I'm a freak!" she started crying.

But the bulge just turned me on so much more. Knowing that the entire time, my babysitter was transsexual is just mind blowing. Every thing made sense, and it was so sexy to me.

"Let me feel." I say as I reach in to her white and blue-striped panties. I felt her tiny soft dick and I got the hardest I've ever gotten. I pulled her pants off and gazed at it's majesty. It was about 4 inches fully harden and it was throbbing at the moment. It turned me on like crazy that I made it get as hard as it did.

"Well?" she said, "what do you think of it? Don't just stare at it! Do something!"

At that moment I sent my lips on it like nothing else. I tasted the salty precum it was producing and it reminded me of my dreams but it was different. It was better.

I began to slowly suck on her little cock and I looked up at her face and she was smiling so big. She was beautiful from head to (pardon for this) head.

I went faster and harder on her cock and she yelled "I'm cumming!" I got so afraid at first because I didn't know what to expect, but she burst in my mouth and it filled my throat with pure ecstasy. It tasted so sweet and indescribable, I wanted more.

"Now it's my turn." Annabelle said with a smirk. She turned around and exposed her juicy ass. "Go ahead!" she turned and said to me.

I was worried because I've never had anal sex before, but I did it like a natural. I began pumping on her in the doggystyle position and it felt incredible. I saw her dick and balls slap against herself and flop all around. She turned around every now and then to express her pleasure, because she could hardly speak out of pure lust. Every now and then she yelled "Mmmm! Fuck me harder!" and things like that that just made me go faster every time.

I finished in her asshole and watched the cum pour out from the sides along my cock and drip down. I knew from that point on I was gonna need a babysitter a lot more, because I've been very naughty.