Bedding The Babysitter: Ep5

I hung up and saw Jenny had continued our cyber conversation.

Jenny78ph: That is ok, I have to go babysit for my neighbor in an hour.

DrMeg: Fun. I am going out right away. I have a date with my girlfriend.

Jenny78ph: Like a friend who is a girl or a 'girlfriend'?

DrMeg: Truthfully, she is a slave of mine. I have a few women who service me sexually.

Jenny78ph: ???

DrMeg: Just kidding.

Jenny78ph: Oh.

DrMeg: Actually, do you want to know a secret?

Jenny78ph: Yes.

DrMeg: I wasn't kidding. I have a woman coming over tonight I am going to use to release my stress. When you are more confident you will be able to release your stress through sex too. Jenny78ph: Not sure I will ever be that confident.

DrMeg: I promise we will find your happy place. You have already begun the transition.

Jenny78ph: Ok.

DrMeg: I want you to do something for me.

Jenny78ph: Of course.

to babysit, I want you to wear the shortest skirt you have, and thigh highs that

Jenny78ph: To babysit?

Are you going to do

sorry for

I have to go and shave for tonight. Do you

Jenny78ph: I trim it.

it is nice and trimmed before you go out tonight. You always want to look attractive down there, even if you're the only one who

I must get going. I

thank

leather skirt, beige stockings and a red blouse. Jenny arrived dressed in one of her plaid school skirts that she must have first worn back when her legs were shorter,

look adorable, Jenny," I complimented her.

pretty too and no, I was just trying something new and didn't

a DVD if

will,"

picked up a new smaller strap-on I hoped to use on my cute babysitter later tonight. After grabbing a quick bite to eat, I drove home

long enough to savour Jenny's soft moans, before I decided it was time for me to 'return home.' I snuck back out the back door and came in the front door. I closed it silently to avoid startling my in-the-throes-of- self-pleasure babysitter.

face and gasped, faking surprise, "Oops, that wasn't the movie you were supposed to

s-s-so sorry, Ms. Cameron. P-p-p-please don't tell my

from what she was doing and also the shame that came from being caught in such a

so sorry," Jenny continued; I found

you were masturbating to a video of me and my submissive Allison is quite flattering," I mused.

clearly overwhelmed just

fucked?" swearing in front of her for the first time. As I reached her, my hand grasped hers and I pulled her up and asked, "Or did you wish that you

came out. Adding to her confusion, I then leaned in and kissed her. At first it was gentle and sweet, but once she responded, tentatively at first, I used my tongue to part her lips. She responded more actively and our tongues danced inside each other's mouths. The urgency of the kiss increased as my hands slid down past her waist and beneath her skirt. The background noise of

and asked, "What

of

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