Jan

This story was told to me by a woman named Donna. At one point in my past, as I was learning the ropes of D/s, I met a woman named Jan. I was more into the D role at that point, and we forged an online relationship.

Jan was my so-called online submissive. I gave her tasks to perform and, using the honour system, she completed them for me.  We were in the early days of digital technology back then, so photographic evidence was understandably lacking.

Part of her obligations to me were to give me access to her email contacts so that I could disclose our relationship to them.  Then, being an enterprising Domme, I would solicit their help in Jan’s “training.”  This provided a nice touch of humiliation for Jan, and also allowed me to get off on the notion of “owning” her. Truth be told, these people I recruited had way more fun than I ever did!

Donna worked in the same office as Jan, and while not in a supervisory role, was at a higher level within their company. Donna was also a lesbian, and Jan told me that they had a shared a kiss at some point.

The setup was the most fun, emailing Donna out of the blue, explaining about my relationship with Jan. She was NOT receptive in the least – initially. I went on to explain that Jan would do anything she wanted, etc. Finally, only after a discrete display of urine drinking in the office did we convince Donna to come aboard!

So, after much preamble, following is Donna’s recap of her first night with Jan…

Jan arrived at my flat promptly at 8pm, as instructed.  She was wearing a thin, tight, white blouse atop her short plaid schoolgirl skirt.  Standard white knee socks for good measure.  I could see the outline of her bra, and I would later find out she was wearing white knickers as well — granny style lol.

[Jan was around 5’3”, probably about 135 pounds — curvy, busty, sturdy.  Petite, but not fragile, yet completely feminine in every way.  In my mind, she would have been a complete delight in the outfit Donna has described.]

Just to reinforce what you and I had spoken of earlier in the week, I had her state for me the purpose of her visit.  “Mistress Steph would like you to help her in my training,” is what she told me.  Perfect!

[I had explained to Jan that she must be well-behaved with Donna and that if she did a good job, we could continue to involve Donna further.  Jan had sort of come out as bi to me earlier in our relationship, so I thought this would be good for her.]

With that, I let her in and we shared a few glasses of wine.  I asked her a lot of questions about her time with you, how it got started, etc.  I could tell she was getting aroused just talking about it, and then the part about Steve! [That’s a whole other story]  Her face turned so red when I pressed her on the details, but it was like she loved being humiliated at the same time.

I asked her to go into the kitchen to fetch the scissor for me, and when she returned with them I had her stand in the middle of the room.  I walked over to her and cut off the top two buttons of her blouse.  In taking a step back, I realized that one more would be just right.  So off went the third button, now revealing her bra.

That would not do, so I handed her the scissors and instructed her to cut the bra off herself.  “No more bras when you’re with me, do you understand?”  Poor thing.  Bras aren’t cheap!  But I was drunk with power at this point.

I helped her pull the remnant of her bra up and out of her blouse and cast it on the floor.  I did sort of a 360 turn around her, drinking in the view of her breasts now being contained only by her thin, tight blouse.  I ended behind her and pressed my body against hers.  My hands went to her hips, and my mouth to where her neck meets her shoulder.

Jan’s hands came up and latched onto my wrists, but not as means of protest.  My tongue and lips were now dancing, slowly, into the crook of her neck.  I asked her if she ever thought about the time we kissed several months earlier, and she said she did and that she thought about it often.  With that, I spun her back around to face me and indulged myself in our second kiss together.  She tasted delicious!

As I pulled out of the kiss, I told Jan that we had to continue with her training — didn’t want to upset Mistress Steph did we?  I instructed her to get down onto her knees and remove my heels, skirt, and panties.  I had shaven my legs and given myself a nice trim just for the occasion 🙂

I sat myself onto my couch and waved her over to me and sit on the floor between my legs.  I can’t remember exactly what I told her at this point — I was really starting to get consumed with the power, you know?  Anyway, there were lots of “you’re going to be a good girl for us” and “you’re going to do everything I tell you to do” statements, all while I was stroking her hair with her head resting on my leg.  I’m sure I had created a massive wet spot on the couch cushion!

For the next few minutes I had her bathe my feet and legs in licks and kisses.  Her tongue and lips were heavenly.  I slid my pelvis slightly forward and laid back into the cushions, putting my pussy right into her face.  My hand grabbed a fistful of her dark hair and I guided her face to my now dripping wet cunt.  No verbal instructions were necessary.

I’d say I had her under the hood for about 30 minutes!  I didn’t know who would ask to quit first — her or me!  Well, it was me!  I had never had so many orgasms in my life.  After that, I had her remove her panties and we snuggled up on the couch together for a bit.  I lazily fingered her, taking breaks to have her lick my fingers clean.  She definitely came a few times, but I was mostly interested in simply luxuriating in the feel of her body.

We drifted off to sleep shortly thereafter.  In the morning I told her that she would wear what she had on to work (no bra, no panties — ha!).  It was a Friday, and the office dress code really goes quite casual on Fridays.  Perhaps not as “casual” as Jan was going to be, but oh well…

And that was the first of many similar messages from Donna.  Like I said, Donna got a way better deal than me on that one!