The Boss's Slut Ch. 06

CHAPTER 6: ANAL TRAINING

"Mr. Woodburn, Tina is here." I was walking toward her cubicle, which had a clear view of anyone approaching from the elevators. As I came to her desk, "You didn't call her, Sir?" She listened and hung up the phone. "Go right in, Tina. Is anything wrong?"

I was usually called up to see him. I smiled, "Just need to discuss something with him."

I pushed through the door and was shrugging my arms from my suit jacket as the door closed. "Good morning, Sir."

"Everything okay, dear?" He was standing with concern reflected in his stance and face.

I assured him I was fine but thought I would get his advice on something. I was removing my blouse, laying it over the jacket, and unfastening my skirt. I let it drop, turned to point my butt to him, and bent at the waist, legs straight, to pick it up from the floor. I turned my head to him as my fingers grasped the garment. Only when I got the approving look on his face did I stand up and take the pieces to hang on the clothes tree.

I stood before my usual chair in front of his desk for his usual moment or two of inspection/appreciation before he gave the signal with his hand for me to sit.

"So, what is your problem?" At this point, I was sure he was expecting something related to an account and maybe it was too complicated to trust to a phone call. Though, we both had agreed this process was more fun than using the phone.

"Not so much a problem, Sir, as your advice about something." He motioned with his hands opening up with his palms out that he was open to helping any way he could. "Anal, Sir." That surprised him.

"Anal?" He leaned back in his chair, a smile growing broad on his face. "We haven't done anal."

"That's my problem, Sir. I never have." He did the hand jester, again. "It came to me this morning as I was showering that it might be an issue at some point."

He chuckled, "In the shower ... you must have been washing very ... intensely for it to come to mind." I blushed. I had indeed. "How might that become an issue."

"When I get involved with a group of men that don't know me, Sir. They may not be as considerate as the men on the Board were. I wouldn't want my first time to be a surprise during a session with clients and have it be painful. It might ruin what we are trying to achieve with the effort."

He chuckled, again. "I am somehow not able to envisioning you involved sexually and it being ruined, but for discussion, go ahead."

I smiled and felt my nipples and pussy tingling, "Thank you, Sir. Your slut is grateful, as always, in the confidence you show. But, Sir, it is in that gratitude of your confidence that I don't wish to ever lose. So, rather than a potential risk of disappointment, I would like guidance in preparing. You have focused on only two of my holes, Sir."

"Are you suggesting, slut, that I have been remiss in your training?" I stammered but he saved me from having to answer. He was leaning back in his chair, gently rocking with a wry smile when he pressed a button on his phone. The door opened behind me. In a moment, Trudy was standing at the side of the desk between Sir and me. She looked at him, then me, "Always nice to see you in here, Tina." She winked and I smiled. Now living in the same building, she and I had gotten together several times when we were alone and feeling the need.

Mr. Woodburn gave us a moment to exchange our meaningful looks. He enjoyed very much that his former mistress and current slut enjoyed each other. It kept open the potential for our threesomes. He described my concern and asked for her recommendation.

"Not a problem. I have a website I use for toys. My boyfriend has become interested in some. I'll give you both the site, but let me go to a 'private window' and show you." She pulled his keyboard over to her, typed in the address, and pulled it up. She quickly clicked to the anal toys for a wide variety of lubrications, plugs, beads, etc. She clicked on one that was shiny metal with a colored, crystal end. "I think these would be very attractive, Sir. They come in different diameters and lengths and jeweled end colors."

He looked at me, "Very attractive, indeed, to see that glassy jeweled end in your butt-hole."

I smiled at them both. "Thank you. I knew you could help me."

* * * * *

"Hello there ... that is a pretty sight."

I was bending at the waist to pick up my dress after stepping out of it. I turned my head to him while remaining bent over for his pleasure, "I think it's cute, very flirty."

"Very erotic, sexy."

I giggled as I moved to the clothes tree to hang my dress. As I approached his desk, he twirled his finger for me to turn around. I anticipated his intention and bent over at the edge of his desk and pulled my butt cheeks apart so he could have an even better look. I had received my order of two sizes of butt plugs and several tubes of lubrication. They were both stainless steel and jeweled ends. The smaller one was clear and the other was blue. I was wearing the smaller one today. It was the first time I had them in when I stripped in his office. I had been experimenting with them at home and finally ventured to wear them for a couple of hours at a time in the office. I had just re-inserted it before coming to his office.

"How does it feel?"

"God, Sir, I love them. I had no idea anal could be so erotic." I turned around and saw the look on his face. I knew we would be having anal sometime soon. As I sat down, he wanted to know more. "I wasn't sure about how it would be so I was cautious about how long I would have them in. Mostly I have used the small one, but I have progressed while at home. After only a few days, I put the small one in, then the medium one after I feel loosened up. The medium one makes me feel full, but even this smaller one gives the same sense." I blushed, "I have started using a dildo along with this one inserted. It's an amazing feeling! Since I've never experience anal before, I never knew how double penetration would feel."

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. "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." I 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.

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

She opened my jacket and seemed to decide 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 was 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? I 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 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 intended to be worn without a bra. Or, maybe it was but not for work, which is why I wore a jacket with it. I received several interesting 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 were ordered, Mr. Woodburn directed me to unbutton one more button. They both watched as I moved my fingers to accomplish the task as discreetly 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 I 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. I 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 stoplight. Blouse, skirt, shoes, and stockings until I was naked sitting in the front seat. There were more stoplights 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 work. Your hole is gaping."

I looked back over my shoulder while my hands were still moving the toys inside his wife while I 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 it 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 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 ..."

He had previously cum with his wife and he was showing some staying power now. With one orgasm under my belt, I settled in for a long fuck, but I was wrong. My second was building when he suddenly began thrusting strongly into my ass. I strummed my clit viciously, then fingers were pinching and twisting my nipples. I looked up to see her intent on sending jolts of stimulation through my body. When I felt his cock jerk and pulse inside my tight anus, I pressed hard into my clit and came with him. My first ass fuck and I loved it!

* * * * *

Mrs. Woodburn managed to get Mr. Woodburn off to play golf with the reminder that he had the rest of the weekend to enjoy us. With that, we had at least the entire morning to ourselves. We were standing on the patio looking over the backyard and in the direction of the neighboring yards. They were very comfortable in telling me that the yard was very private so I could be naked, but when I suggested she be casually naked in the backyard, it suddenly required a little more consideration. There were a few places where someone might see if they were aligned perfectly and she finally agreed it was unlikely.

She was wearing a light robe she had put on for breakfast before Mr. Woodburn went off to golf. I was, of course, naked since sometime last night. I pulled the tie loose from around her waist and her robe gaped open. My hands moved inside and caressed her naked body underneath, finally cupping her more substantial breasts and I leaned in to kiss her. As I pulled away, I slipped the robe from her shoulders and she allowed it to slide down her body to the patio blocks at our feet.

It astounded me how the act of being taken anally by Mr. Woodburn last night still had me stimulated in attitude. What I had said to him in the heat of the moment, now still seemed to be true inside me: being taken in the ass was a truer appreciation of being his to have and use. I felt consumed to discern what that meant.

We had agreed on a lazy morning of girl-girl loving and mostly outside. Mrs. Woodburn's acceptance of being outside naked was just beginning and to add our sexual exploration of each other on top of it was bound to be a heightened experience for her.

The slut within me, though, was breaking the chains binding her and she fought to not only find her freedom but to take a measure of control over me. It was a measure of control I welcomed giving up to her. I welcomed her presence alongside my control and professional self. I relished the very idea of seeing my world through the eyes of this slut and experiencing life through her wantonness and completely uninhibited nature. I wanted this part to stand beside me as equals, professional or slut, different sides of the same.