Oh What a Night, Part 2

December 31, 2019/January 1, 2020

I heard the dungeon door open and Sir began to talk to Tripp. “Anywhere within the heart is fine”, He said. “You can also hit the ass and the thighs, but don’t go outside the heart or you can damage the kidneys. Hold the flogger like this, put your right foot forward and put your weight on it, raise your arm, and let the weight of the flogger fall. Try and hit the same spot every time to start.” Tripp practiced on my back for quite some time. Towards the end, he was actually getting pretty good. Sir and Tripp took turns flogging me, with Sir demonstrating technique and coaching Tripp.

When they were finished, I was taken off the cross, still blindfolded, and led to the sling. Sir guided me into the sling and reattached the wrist and ankle restraints. I could feel Sir running his hands over my cage and balls and my ass. My cock was pressing tightly against the walls of its prison. “Tripp?” I asked. “I’m right here” he answered and kissed me. “You’re doing so well” he said as he lightly brushed and played with my nips.

Sir is very verbal during a scene. I really like that. Tripp is usually very quiet during sex, which is funny because he otherwise talks all the time. I absolutely get off on humiliation and dirty talk during sex. Call me a whore, a bitch, a fag on the street and thems fighting words. Say it in a scene and I get so fucking turned on. I’ve been locked for almost 500 days by this point and I hadn’t been allowed an orgasm for 235 days. As Sir started fingering my hole and yanking on my balls, I was extremely hard, the head of my cock pooching out of the vent holes in my cage. Sir started talking to me. “Do you like that? You like my fingers in your pussy, slave?”. “Yes Sir, I love that”, I answered. “Are you my pig?” He asked. “I’m your fucking pig, Sir” I responded. “Whose my bitch?” He demanded as he slid 4 fingers into me. “I’m your bitch, Master”, I cried out. I could feel the pressure in my cock, the pre-come flowing, and the beginning tingle of an orgasm, but I generally can’t come without some form of direct penile stimulation which is why my cage is so effective. Then Tripp put his mouth to my ear and whispered “You’re my bitch too” and I came. I came hard. I screamed and convulsed and I shot my 235 day load. My cage points downward and the hollow PA allows piss and cum to exit in an almost normal fashion. So it was like a cannon pointed directly at Sir. A cannon with 235 days of ammunition. “Well”, Sir said, “you came all over my dick, slave. What are we going to do with this?” and then he proceeded to fuck me using my own come as lube. He plowed me until he shot his seed into me. When he finished, he replaced my plug and walked around the sling so I could lick his cock clean. The taste of His come mingled with mine was intoxicating.

They removed my blindfold, released the restraints, and put me in Sir’s cage with a bottle of water and my phone, so I could entertain myself while they went to the house to have Champagne and watch the ball drop for New Years. As they left me, Sir remarked that I was his last fuck in 2019, and in a little while, I would be his first in 2020.

They returned about an hour later with the Champagne bottle. I was released from the cage. Sir took a swig from the bottle, pressed his mouth against mine, and spit the Champagne into my mouth. “We didn’t want you to feel left out”, he said. I gulped it down. It made me hiccup as it was quite a lot. The plug was removed and I was put back in the sling as it was time for Sir to ring in 2020 and get his first fuck. Before He fucked me, He asked Tripp if he would like a go. Tripp doesn’t really get hard because of the chemo, but Sir had left out several large dildos and Tripp has a strap on harness. He selected a rather large one and impaled me with it. Tripp pegged my already stretched ass, pulling my hole closer and closer to him. I was so hard, I thought I might shoot again. When he was finished, Sir moved behind me and rammed His cock into me. He fucked me hard. His balls were slapping against my ass. He pounded me mercilessly until I felt a second load fill my ass. I was absolutely spent as Sir replaced my plug. I was going to stay plugged until I got home so that Sir’s DNA would remain in me for as long as possible. They took me out of the sling and both kissed and hugged me. I curled up on the floor at Sir’s boots and licked them. He didn’t order me to, I just did it. I needed to do it. I was deep in sub-space. Tripp placed his hand on my bruised back and rubbed it gently. We stayed that way for some time. “It’s time to go home, honey”, Tripp eventually said. I gathered myself as best I could and we headed to the car.

I think that was the best New Year’s eve I have ever had, and I think, at least for a little while, I had two Masters owning me.

Hugs and happy New Year to you all.

-Doc