Unspoken Pleasure

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.

DrMeg: When you go to babysit, I want you to wear the shortest skirt you have, and thigh highs that match.

Jenny78ph: To babysit?

DrMeg: Yes. Are you going to do as I say?

Jenny78ph: Yes, sorry for questioning you.

DrMeg: It’s ok. I have to go and shave for tonight. Do you shave your special place?

Jenny78ph: I trim it.

DrMeg: Be sure 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 knows.Belongs to NôvelDrama.Org - All rights reserved.

Jenny78ph: OK.

DrMeg: I must get going. I will talk to you later tomorrow.

Jenny78ph: Ok, thank you… Bye.

I got ready for my fake date. I would go out for an hour or so, giving Jenny enough time for my plan to kick into action. I was dressed in a black 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, mocha thigh highs, and her white school blouse. You could clearly see her nylons were thigh highs.

“Wow, you look adorable, Jenny,” I complimented her. “Do you have a late-night date?”

“Thanks Ms. Cameron. You look pretty too and no, I was just trying something new and didn’t have time to change.”

“Well it really works for you,” I said, gently squeezing her shoulder. “I’ve got a hot date. Max is already asleep, so you can watch a DVD if you want. I think you’ll like the one in the machine, it’s a fun movie.”

“Ok, have fun,” she said, her usual bubbly self.

“Oh, I will,” I said ever-so-coyly.

After I left, I drove to a nearby adult store and 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 and snuck in the back door, quiet as a mouse.

From the dark kitchen, I checked in on my babysitter.

She was on the couch, her legs open and her hand assumedly pleasuring herself as she watched a scene of me fucking the pussy of a pretty 21-year-old coed I had seduced a while ago. The girl, a sweet submissive volleyball player named Allison, was screaming “Yes Mistress, fuck me, bang my tight pussy!” I allowed the scene to go on for a couple of minutes, 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. The sounds of the DVD echoed through the house, “Yes Mistress, pound me, I’m coming!” When I entered, Jenny scrambled to cover herself, but couldn’t do so in time.

I looked at the TV, a sly smile on my face and gasped, faking surprise, “Oops, that wasn’t the movie you were supposed to see!”

She stammered, apologized and begged me “I-I-I am s-s-so sorry, Ms. Cameron. P-p-p-please don’t tell my mother!”

Her red cheeks expressed both guilt from what she was doing and also the shame that came from being caught in such a compromising position. “It’s ok, my dear, masturbation is natural.”

“I-I-I am so, so, so sorry,” Jenny continued; I found her embarrassment so cute!

“Actually, the fact that you were masturbating to a video of me and my submissive Allison is quite flattering,” I mused. “What turned you on the most?”

“I-I-I don’t know,” she replied, clearly overwhelmed just that we were talking about such things.

“Did you find seeing me with a strap-on exciting?” I asked, moving closer. “Or was it Allison being 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 were the one on all fours getting fucked by my big strap-on cock?”

Her mouth dropped open and she froze in place, speechless. Her mouth opened and closed several times and faint sounds emerged, but no words 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 Allison coming on my strap-on enhanced the intensity of our kiss.

I finally broke away and asked, “What does my Jenny78ph want?”

“Pardon?” she asked, the significance of the words not immediately registering.

My hand traced her pussy lips through her wet panties. “Hmmmm, you are very wet, Jenny78 pantyhose.”

She let out a soft moan from my touch. “H-h-how do you know my MSN name?”

“Oh, Jenny, Jenny, Jenny. Have you not figured it out?” I smiled, my finger tapping her protruding clit.

Her breathing increased, and my finger was causing her so much distraction she couldn’t make the obvious correlation.

I asked, “What is my first name, Jenny?”

“M-M-Megan,” she moaned. I watched her face and her lips as she moaned with desire. It was so adorably cute as the light bulb came on and her face brightened to astonishment. She asked, her words coming out stunted as my finger continued putting pressure on her clit, “Oh, um, wait, oh my God, are you Dr. Meg?”

“The one and only,” I purred, as my finger slipped past her soiled panties.

“I-I can’t believe it,” she gasped, astonished by my revelation.

“Yes, my dear, and I am now about to relieve all your stress and satisfy all your curiosity,” I promised, my finger now between but not inside her wet pussy lips.

“But how?” she asked, overwhelmed as she began seeing further implications that could stem from this sudden new level of our friendship. I had baked cookies for her when she was fifteen, and now I was touching her twat!

“I’ve always thought you were sexy… shy but sexy. When I overhauled your computer I searched for clues and found which sites you usually frequent,” I explained, before adding with a playful smile, “By the way, for future reference you need to erase your daily history if you don’t wish people like your Mom, or conniving neighbors like me, to learn all your secrets.”

“Aaaaaaah,” she gasped as my finger took the plunge and slowly penetrated her fevered pussy.

“Jenny, it’s all right. You’re a lesbian and submissive; I am a lesbian and dominant,” I explained.

Jenny, still trying to get the whole picture straight in her mind with one less player now on the field, stood there in a sexual trance. Her mind was trying to process the bizarre reality currently happening around her while within, her body was begging for the attention it had long craved.