My Best Friend Employs Me

I felt Svetlana apply a glob of something to my asshole, and then she placed a tub of Vaseline on the desk. I braced for the pain, as she lined up the strap-on with my sphincter. Then I felt her slowly ease the massive phallus between my ass-cheeks. To Svetlana's credit, she was not trying to injure me, temporarily or permanently. She got off on inflicting humiliation on men, and dominating them through fear. However, she wasn't trying to hospitalize me with a torn rectum.

I wouldn't characterize her treatment of me as gentle. However, she waited until my anal passage had adjusted to the invasion, before she really start to butt-fuck me. It was uncomfortable, but not painful, thanks to the large glob of Vaseline that she had shoved in my ass. Humiliating, but nothing that was going to make me cry. I just sucked it up, and let her fuck my ass as my punishment.

She was having a great time. She was whooping and hollering, and would periodically slap my ass very hard and call me her bitch. The spanking glove hurt like hell, and the pain increased, as she hit me on the same spot each time. My upper body was resting on the desk, as I was trying my hardest to obey her directive to not move. However, after each spank, I would recoil, arch my back and my little bell would ring.

I was very surprised how painful the repeated spanking was, although the actual ass fucking wasn't even that unpleasant. I did decide to cry though, albeit fake tears. I hadn't been punished since I was a kid. However, a memory stirred of my punishment being increased, because I wasn't crying enough. I didn't want Adrian to decide I need more punitive measures, because I wasn't showing any signs of distress.

So I whimpered and cried out in pain occasionally. I even went as far as to beg Svetlana to have mercy on me.

"Sara, see if my bitch is faking it," Adrian said sternly.

The poppers had already brought tears to my eyes, so Sara was able to report back to him that I was actually shedding some tears.

Svetlana was enjoying it more than me obviously, but it wasn't nearly as bad as I had imagined. I think she fucked my ass for about thirty minutes, before she finally slowly withdrew the massive strap-on. I heard the click of the harness as she removed the black strap-on. She laid it on the desk next to my face, and I was shocked as soon as I processed what I had seen.

The dildo that Svetlana had fucked me with, was about the thickness of two fingers, and was about five inches long. It was white in color and made of glass, so it was really smooth. There were no signs of any fecal matter anywhere, so my anal cleanse had worked perfectly. I assumed my punishment was over, but Svetlana had one more trick up her sleeve.

She laid a prostate massager on top of the desk.

"Have you ever been milked before, handsome?" Svetlana asked.

I moved my head from side to side to indicate no. She reached for the Vaseline that was still on the desk, and lubed up the tip of the sex toy. Then she inserted the prostate massager into my ass, and immediately found my magic spot. She had obviously done this before.

She started to manually massage my prostate using the massager, and I felt my cock throb in my latex shorts. I had been erect ever since Sara removed my cage. Now as Svetlana expertly massaged my prostate, I could feel myself leaking into my shorts.

The shorts were designed to be skin tight, but they had a silk lining to prevent chafing. As Svetlana was massaging me, my cock was getting rubbed by the silk and I was leaking pre-cum. It didn't feel like an orgasm, but over a period of several minutes, she milked me dry. My latex shorts were wet with my semen. Once she was satisfied my nuts were completely drained, she turned to Adrian.

"Do you want to fuck Chrissy, while he is ripe for the taking?"

I felt very vulnerable, bent as I was, over Adrian's desk. I had my asshole lubed, my rear zipper opened, and my anal passage already opened up, from Svetlana's prolonged ass-fucking. I couldn't be any more available to this man.

The conversation between Svetlana and Adrian took a sinister turn.

Adrian said, "I do want to show Chrissy who is the boss. I do want to fuck him in the ass. Make him my bitch."

I gulped as I processed his words.

"However," he continued, "I don't want him tied up like some non-consensual prison rape. I want him to willingly submit to me. I want him to get a Brazilian wax, cleanse his anal passage with an enema, wiggle his ass seductively and invite me to fuck it. I might even make him wear lipgloss and lingerie, when I do finally fuck him."

I shuddered when I heard those words. They seemed like a prophesy, and etched themselves into my memory.

Svetlana grabbed the leash, and tugged on it to force me to stand.

"Shall I put him back in his cage?" she asked Adrian.

Adrian took a look at my tear-stained face, and concluded that I had been taught a lesson. He dismissed me with a wave of his hand. Svetlana took me out of his office by my leash, my tiny bell jingling as we walked down the hallway.

As we walked down the long hallway from Adrian's office, Svetlana's tone softened.

"Great job handsome, for taking your punishment like a man. For not crying out like a bitch. For sucking it up. I thought you were going to change your mind for a split second though," she said. "I had been looking forward to taking your anal cherry all morning," she continued. "I am so happy I talked you off the ledge."

It was then that I realized that her words of comfort during my panicked moments, were not driven by empathy. She was worried I would change my mind, and she wouldn't get her jollies fucking my ass.

"I am very proud of you, handsome. I am going to suck you off before I cage you, like I promised."

I was always bewildered around Svetlana, because I never knew which of her two distinct personalities was the real one. There was sweet Svetlana, who I had made out with, as she rode my strap-on for over an hour.

Then there was the young Czech sadist, who terrified me. Sadistic Svetlana had fucked my ass. She had put the cock-cage on me, before it had cooled to a safe temperature. She had rubbed medical grade BenGay into my nuts, to cause me severe discomfort. Now, as I walked down the hallway with sweet Svetlana, I was hoping her sadistic alter ego would not surface.

She took me into the pool house, presumably for privacy. We wouldn't have been too hard to follow. My bell jingled the entire time that she walked me through the huge house, by my leash. When we got to the pool house she patted the bed, motioning for me to sit. I cautiously lowered myself onto the bed, and was happy to feel no pain. She removed the leash from my neck, and then took off my pink choker and that emasculating tiny bell.

After she untied my hands, she told me to lie down, and together we managed to extricate me from the skin tight latex briefs. I had leaked a copious amount of semen into them when Svetlana milked me, and they needed washing. However there was no blood inside them, so that was a relief. She got a wet wipe and cleaned my ejaculate from my genitals. It was all over my cock, balls and pubic area, contained as it had been by the tight shorts. Her touch felt great, and she was being tender now and talking sweetly to me.

After she was satisfied that I was clean, she grabbed my hand and pulled me up into a seated position, on the edge of the bed. She told me to wait a few moments and she left the pool house. I watched her tight little ass wiggle in her skin tight latex catsuit, as she walked through the door.

Strangely enough, there wasn't much reaction from between my legs, and as I glanced down, my cock was completely flaccid. It did occur to me, that Svetlana hadn't bound my hands together when she left the room, which was the required protocol, whenever I was released from the cage. She had seen my cock was soft, but in my current state of arousal, as I waited for my upcoming blowjob, we both knew I would be hard very shortly.

I think she knew that my fear of retribution would prevent me from jerking off. I sat on the edge of the bed, and waited patiently for Svetlana to return.