THE BOSS’S SLUT 7: Anal Training

CHAPTER SEVEN: 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 really 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 really 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 the purpose of 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 hours at a time in the office. I had just re-inserted it prior to 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 really 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 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.” 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, 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.