The Boss's Slut - S01 E32

Story 1 month ago

The Boss's Slut - S01 E32

Read Story: SEASON 1 EPISODE 32

ANAL TRAINING

He shook his head and smiled. "Have you mentioned these to Deborah by chance?" I nodded. She and I have taken to calling each other ever since that day with the dogs. "She asked me about anal. She's never had any interest before."

The taxi left me at the front door of the Woodburn estate. I knocked on the door holding my purse and overnight bag. I never quite knew what to pack for visits with them. Sometimes I needed an evening gown for the club or dinner. Sometimes all I needed was clothes for the return trip.

Mrs. Woodburn opened the door and immediately enveloped me in her arms. She pulled me into the house and gave me a deep kiss. After, I put my bag against the wall out of the way and began taking off my suit jacket. Mrs. Woodburn had decided to duplicate Mr. Woodburn's rule about my nudity. When I agreed to extend my arrangement of being a personal slut to include her, she added the rule that I was to be naked inside her house unless otherwise directed.

"No. Let me take a look at you." shrugged my jacket back on and stood erect in front of her. She was something of a student on how 'proper ladies' carried themselves, standing and sitting. She had been working with me on those things during my visits while I had been working with her in more sexual matters, including the dogs.

"We're going out to dinner. I see you've come directly from the office." I nodded.

She opened my jacket and seemed to make a decision by taking my jacket off and laying it over my bag. She then opened the buttons of my blouse until the first one buttoned was just below my nipples. Not being allowed to wear a bra meant my nipples were vaguely visible through the thin, satiny material of the blouse. Another button undone and things would be blatantly displayed. As it was, my jiggling breasts would be partially visible whenever the blouse gapped open.

"I think that will work." Mr. Woodburn arrived from upstairs. She turned to him, "What do you think? think by opening some buttons and leaving the jacket here..." They both looked at me while I remained still. She twirled her fingers, just like he does in the office, so I slowly turned in a circle.

He volunteered, "It would be nice if the skirt was shorter away He volunteered, "It would be nice if the skirt was shorter away from work, but...", he got a guilty look about him, "I may have forgotten to mention dinner." I felt relieved that I hadn't missed something during the hectic day while she muttered something unintelligible about men,

The blouse wasn't really intended to be worn without a bra. Or, maybe it was but not for work, which why I wore a jacket with it. | received a number of interested looks upon entering the restaurant. My breasts jiggled as I walked and my nipples were poking prominently at the thin material. After a starter drink and our meals ordered, Mr. Woodburn directed me to unbutton one more button. They both watched as I moved my fingers to accomplish the task as discretely as possible. They smiled at each other, much better apparently. I looked down and was sure I would be flashing the waitress and other staff during the evening.

Through dinner, Mrs. Woodburn leaned in to ask questions about my use of the butt plugs. Then she blurted out, "Do you have one in now?" She put her hand over her mouth and giggled with embarrassment, but was doubtful anyone around had a clue what the 'one' was. I nodded to her that I did. I had added it just before leaving the office. She looked at me, "Naughty girl, did you put it in while in your office?" I nodded, again. Mr. Woodburn smiled big. 1 suspected he was Imagining being the one to happen to walk in on me at that moment.

She asked more questions, some we had covered in other talks. Yes, it feels full and erotic. Even simple things like walking, sitting, shifting positions and angles have an erotic effect. Yes, sitting takes some getting used to. It drives the plug deeper and is felt more intensely. Yes, with it inside and adding something 'next door' produces a very full and exciting feeling.

The discussion in the restaurant was having a powerful effect on me. It was also making me much more aware of the plug in my ass. I could feel the juice leaking from my pussy and we could all see the effect on my nipples. The waitress did, too. She began standing on the other side of the table to take orders so she had a better vantage point to me. She might have been missing out on looking down my blouse, though.

On the way home, they raised the stakes significantly. As we waited for the valet to bring the car around, my blouse was unbuttoned to my skirt. It now billowed up with the slightest breeze and it was that night. As I got into the car with the valet holding the door, he was torn between what he might see under my skirt and what he was seeing inside my blouse. On the way to their house. I was instructed to strip, with one item removed at each stop light. Blouse, skirt, shoes, and stockings until I was naked sitting in the front seat. There were more stop lights but all that did was allow someone outside to get a look before the light changed.

Mr. Woodburn brought glasses and wine to the bedroom, finding his wife and me already engaged in the downturned bed. He quickly undressed and arranged us. He wanted to fuck his wife's pussy while she ate my pussy with my feet toward the headboard. At first, this didn't make much sense to me until he started moving the plug in my ass. All three of us came quickly and I was sure that was the idea.

Then, as we gave him some recovery, I retrieved the small plug from my case, lubed it up good and twisted it into Mrs. Woodburn. She moaned, groaned, and gasped, but I did push it past her reluctant sphincter. Then, she went nuts when I insert a smaller diameter, vibrating dildo into her pussy. From my own experience, I knew the vibrations from the pussy were transmitted directly into the anus. Her orgasm was rising quickly.

I felt the bed behind me sag, then, "No time like the present to truly become my slut."

I felt the plug in my ass being pulled. There was a moment my body resisted, the natural reluctance of the sphincter to open. I pushed to relax and the plug came out. "They really work. Your hole is gaping."

I looked back over my shoulder while my hands were still moving the toys inside his wife while was on my knees bent over, "Better fill it, then, Sir. Make me truly your slut. Seed my ass and claim me I understand a slut is only truly owned when her ass is taken." I think it turned him on as much as did me.

I felt his cock head at the entrance to my asshole. I held my breath and concentrated on relaxing just as I did with the insertion of the medium sized plug. There was pressure and he was in. The plug really did prepare the anus for penetration... that and lube.

Mrs. Woodburn came, first. Then I did as I used fingers on my clit for extra stimulation. I was wondering about him, though.

"God, your ass is still so tight. I love both of your pussies (smart man to include his wife lying right here with us), but your ass ohhhhh, this is wonderful. I never knew..."