Jackie's First Threesome Pt. 01

Story Info
Maddy and Kelly prepare to turn Jack into a sissy slut.
1.2k words
3.56
24.1k
5
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Set in the hopefully not too distant future...

I sighed as my eyes drifted to the clock for the thousandth time that day. Still an hour left— only two minutes less than the last time I checked. One hour, and then I would rush out of the office with everyone else... I wondered momentarily if any of their plans for the evening were as devious as mine, or if they could ever possibly suspect what I had lined up. Doubtful, on both counts. My coworkers, despite many of their hipster/counter-culture pretensions, were quite tame. They might stop somewhere for drinks first, but then at home it would be some Daily Show then bed; maybe a little missionary with their boyfriend/girlfriend/fuck-buddy if they had one, possibly with some doggy-style thrown in if they'd had a bit to drink and were feeling raunchy. I'm sure they expected even less of me: gym, read something boring, then bed; which, granted, is how I spend many of my evenings. But not all...

I smiled in satisfaction at their ignorance. Most people, as far as I can tell, like people to think that they're cooler than they actually are. I've always been the opposite: I get off on the fact that many of the most interesting things about me are things most people would never guess or even believe to be true. They're too busy stereotyping me as a total nerd, and probably a prude, which is more than fine by me. I'm not sure why... it's almost as if the less people know about something, the more it belongs to me.

Half an hour now. Jack would be landing any minute, and Kelly would already be in my apartment, finishing her chores, getting ready. Of course, neither of them had any idea what they were in for that night. Jack, I'm sure, assumed that he would be in charge. Not that I objected to that (at all), but it was pretty obvious that he was due to be taken, and there would be time for everything else too. Besides, a lot of things had changed for me recently— I was finally out of college, had a real job, my own apartment for the first time in years, and Kelly— I was feeling grown-up, and, more importantly, powerful. Kelly... Jack didn't even know about her yet— I was saving her as a surprise, and now it was time.

Time! I gathered my things, made some lame excuses when my friends invited me out for drinks ("Oh Maddy... that girl needs to learn to have some fun!"), and, a few subway stops and a short walk later, I was home. As I walked upstairs, my phone buzzed. "In cab," Jack texted, "Ready to be a good little slut for daddy?" I smiled. Maybe tomorrow, daddy.

When I got to my floor, I slowed my habitually brisk pace to a deliberate march, so that my steps would alert Kelly to my approach, in case she was not already prepared. At my door, I heard some scrambling inside as I took slightly longer than necessary to find my key and unlock the door. I'm not always so considerate, but she was in for a rough couple of days. I would take it easy on her, for now.

When I finally opened the door, she was in her position kneeling in the front hall, with her head down, where she would stay until instructed to move. "The position" had actually been her idea. I personally found it to be a little over the top— more amusing than arousing, but it did wonders in getting her into the right mindset, which I did appreciate. The outfit, however, was all me. Even on days we did not see each other I would text her instructions on what to wear. Today, it was thigh highs, stilettos, an obscene bustier, and, as always, a collar and leash, with the end of the leash hung conveniently on a hook on the wall. With her head down, she could not see me, but she could hear me, and held her breath as I approached. I walked right past her without pausing. I would ignore her entirely for at least five minutes: partly because I needed to unwind a little after the long day, but also because it drove her crazy. She was forbidden to move— she would wait patiently to be used, much like my furniture and other possessions— and every second of it made her pussy gush.

I walked into my apartment and saw that she had completed all her chores for the day: mainly cleaning, laundry, and shopping. Normally I would have her cook for me as well, but tonight we'd be going out. Today, I also had her pack everything we'd need that night, not that she had any idea what we'd be using it for. I looked inside the bag on the couch and saw everything I'd requested packed neatly inside— clothes and shoes for Jack (wonder what she made of that?), makeup, strap-on, and enough bondage gear to scare the pants onto a pornstar. Good slut, I smiled, satisfied. I did totally get off on the whole domestic servitude thing (as did she).

She was nineteen, six years younger than I was, and currently bouncing back and forth between various fluffy humanities majors at NYU (cultural anthropology that week, I think). We were very different in both personality and physique. Her tiny, curvy, blonde figure and bubbly ditziness contrasted sharply with my tall, slim, almost boy-ish build, dark sense of humor, and intellectual inclinations. I actually found her a bit irritating at times, but hey— this is why they make gags. In another time, she would have been someone's Stepford wife, but modern feminism and a narrow but very deep rebellious streak had delivered her to me instead. I found her the same way Jack found me, years before— on a website designed to help people realize their most perverted and devious fantasies (often so difficult to accomplish "in real life").

I picked up my phone to text Jack back, "I guess we'll find out... I need to shower, then I'll be on my way." On my way to the bathroom, I called to Kelly to go set my clothes out for me: silk top, high-waisted skirt and belt (to draw attention to the fact that I actually do have a waist and hips), and four inch heels. I don't wear heels often— they make me over six feet tall, and cause my legs and ass to attract more attention than I'm typically comfortable with— but Jack loves the way I look in them, which is, admittedly, extremely hot. Kelly would just be throwing on a trench coat over her sex slave garb.

While I was in the shower, I went over my plan of attack. A battle plan was necessary because, although he craved and begged for it when we were apart, Jack was extremely evasive about actually slipping into his submissive slut persona: Jackie, as we called her. A couple of times I tried to take her by force, but Jack is much bigger and stronger than I am, so the contest was over before it even started (although it did make for extremely hot foreplay). The spanking and general manhandling I received for my troubles had, in fact, taught me a lesson, though probably not the one he had intended. It was obvious that if I wanted Jackie to come out and play, I was going to have to get creative. Fortunately, this is an area in which I excel...

To be continued...

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 9 years ago

So sexy

Share this Story

Similar Stories

Lesbian Polygamy: A Beginning The beginning of how a domme began her own lesbian harem. in Lesbian Sex
Seduced By His Mistress When the Wife meets the Mistress the plan changes.in Lesbian Sex
My Weekend Surprise Ch. 01 My wife and friend help out with my fantasy.in Transgender & Crossdressers
Finally Fucked A white couple crosses the line and get what they both need.in Interracial Love
Sam's Panties About a wife, her girlfriend and sissy cuckold hubby.in Fetish
More Stories