My Best Friend Employs Me Pt. 13

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This might hurt a little!
1.5k words
3.94
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Part 13 of the 19 part series

Updated 06/10/2023
Created 08/13/2020
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After Adrian had finished working out, he took his coffee in the study. I was summoned to meet with him and both girls escorted me there. "Chrissy's" sucky pillow was at his feet, so I knelt on it. He kept me waiting for a few seconds as he read his Wall Street Journal. He folded the paper neatly, and turned his full attention to me.

"Did you choose your punishment?" he asked.

"I want Svetlana to fuck my ass," I said quietly, almost choking on the words.

He let out a chuckle and said "Ouch!"

"Ask Svetlana nicely if she has time later this morning to punish you," Adrian said, relishing the control he was exerting over me.

Everything Adrian did was planned to either emasculate or humiliate me, or to diminish my value in Sara's eyes. I asked Svetlana, and she said she could fit me in at 11am.

Adrian said "11am it is then Chrissy," and I slinked out of his study clutching my heart-shaped sucky pillow.

I only had an hour to prepare myself, so I had two very stiff vodkas to try and relax. About five minutes before my appointment, I inhaled a very large dose of the liquid in the vial. Combined with the vodka, it went a long way to reduce the anxiety and, hopefully, the pain. Two minutes before my punishment time, Sara tied my hands behind my back and released me from my cock-cage. Mary, Adrian's private nurse, examined me briefly, but her main concern was heart palpitations, and she deemed me "good to go".

I went into the office at my appointed time feeling no pain. I just hoped to God it stayed that way! I was dressed exactly how Svetlana had told me to, and I felt very self conscious. I was wearing my skin tight latex briefs that Svetlana had modified slightly. To facilitate her access, she had cut a small hole in the rear of the shorts, and sewn in a very short zipper. I didn't see the point of the zipper. It seemed to me, that the hole itself served the purpose of enabling her to stick her cock in my ass. However, I didn't ask any questions. I also had on my feminine pink choker with the tiny bell attached. Other than that I was naked. I looked like a house-boy for a wealthy gay man.

Sara and Adrian were there sitting together on a love-seat. It looked like they had tickets to a barbershop quartet, the way they sat they expectantly waiting for the show to start. I had quite a buzz from the vodkas I had just pounded, and I was really light headed from the poppers. I walked over to the desk as I knew this was where Svetlana planned to violate me. I stood there with my head spinning, praying to God that I didn't pass out.

Svetlana strode into the office at exactly 11am. She walked right behind me and grabbed me by the ear. I let out a squeal of discomfort, as she twisted it and then yanked me by my ear to the middle of the room. She told me to kneel and look up at her. I dropped to my knees, and slowly raised my head to meet her gaze.

She looked quite fearsome the way she was dressed. She had on a black skin-tight latex catsuit, that accentuated her toned body perfectly. The front of the catsuit pushed her tits together, and showed lots of cleavage. She was wearing a black leather spiked collar, onto which was clipped my cock-cage key. Her black leather boots were knee high with metal spiked heels. The boots had been recently polished, and gleamed.

Her hair was pulled straight back into a ponytail, which made her look much harder. She had on one black leather glove, which I later learned was a "spanking glove." Who knew such a thing existed? It was made of hard leather, with pads inside the glove, designed to protect the spanker's hand from impact irritation.

Around her crotch there was an ominous looking leather harness. I assumed she would attach the strap-on to that harness, before she impaled me with it. Her beautiful natural green eyes were gone, replaced by black contact lenses that made her look soulless. She looked like a Nazi interrogator, and I felt a shiver go down my spine.

She was holding a black leather dog leash in her spanking hand. She allowed me to check her out for a few seconds, enjoying the palpable fear in my eyes. Then she affixed the leash to my choker, and told me to stand. My legs were trembling as I stood, and for a few seconds I thought I might actually piss myself. At least she wasn't going to make me crawl to the desk like a dog, the way Adrian had treated my wife.

When we reached the desk, she walked around to the other side of it and tugged down on the leash. This forced me to lower my upper body against the desk, so that I was bent at the waist.

She didn't even bother to tie my leash off, but said, very firmly, "Do not move an inch, bitch."

Then she turned to Adrian and Sara. "Fear will immobilize this pussy," she said proudly. "No additional restraint necessary."

I heard her walk behind me, and then she picked up the strap-on and put it on the table, right by my eyes. I tried to remain calm, but that thing was way bigger than I remembered it. It was massive, and even though it was slick from having been already lubricated, it was never going to fit in my asshole. I prayed that the poppers would relax me enough to take it. Svetlana picked up the black cock, went slowly around the desk, and got behind me. I heard the click of the strap-on being secured into the harness, and a shiver went down my spine.

I tried to look back, but Svetlana growled, "Don't fucking move," and I followed her directive.

Svetlana slowly undid my zipper, and I understood why she had taken the time to modify my briefs. It added an extra element of suspense, to be bent over and have her make me more accessible, by unzipping me.

It was right at this moment that I changed my mind. I had never had my ass fucked before, and the thought of that massive silicone strap-on, getting forced into my virgin butthole scared me. No, worse than that, it terrified me. I think Svetlana may have anticipated a possible change of heart on my behalf. This was probably why she had bent me over the desk at the waist, and told me not to move. Sara had also bound my hands behind my back, and between them, they really had rendered me immobile.

Then I started to stress about why Mary was there. Was she going to give me medical aid if something went wrong? How would she be able to help me if Svetlana tore my rectum, or worse? I started to breathe heavily, and was on the verge of a panic attack.

This was obviously not the first time Svetlana had fucked a guy's ass. She recognized the signs of panic in me, and sought to ease them. At first, I thought she was acting out of empathy. I would learn later that this was not the case. Svetlana leaned over me and started to whisper in my ear. Her spiked collar was digging into my the back of my neck, and I hoped it wasn't sharp enough to draw blood. I could also feel that hideous black cock, as she leaned over me. It felt like it ran from my lower back to my shoulder blades. Fuck!

"I won't hurt you if you remain passive throughout your punishment," she assured me. "I have done this before, many times. The only injuries I have ever seen, were when my hapless victim struggled to resist, or moved around too much. Trust me. You are in expert hands. There is a nurse here, in case something does go wrong. This is your better option. By lunchtime, all that will remain of this punishment, will be you with a very sore ass. Maybe a little blood in your latex shorts. However, if you change your mind, and allow Adrian to send compromising photos to three random people on your email list, your life will forever change."

Svetlana's pep talk did calm me down a little, and my breathing slowed.

"Are you going to gag him?" Sara asked Svetlana.

"I was wondering the same thing," Adrian chimed in. "The first time I butt-fucked Sara over Chris' office desk, I stuffed her panties in her mouth, as a makeshift gag."

"This is completely different," Svetlana said to Adrian. "You and Sara were enjoying a consensual sex act, and the gag was done to enhance your dominance of her. My upcoming assault on Chris' virgin ass, is punishment. The three of us need to hear his cries, both to gauge the sincerity of his remorse, and to establish that he has been sufficiently punished. I am not going to stop fucking his ass, until he has cried genuine tears, and has begged me to stop."

Sara and Adrian high-fived each other, and agreed "no gag!"

Svetlana stood back up, straight behind me. "This might hurt a little, handsome," she said coldly.


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