getDare Truth or Dare - Non-Fiction: Slave Olympics

Miss Jenn was putting the finishing touches on her bondage work as we entered the room. Dan was tied on his back with both his hands and feet above his head and secured to the headboard. I was thankful I was not in that position as I am not a flexible person and having my legs basically behind my head would have been fairly uncomfortable. This left his ass exposed nicely and I had payback on my mind after he raped my throat the day before. This position also gave him a good view of what was happening to him which definitely added to the humiliation factor. The smile on my face could have lit up the room as I don’t get to experience this level of control very often.

Miss Meg walked toward me and grabbed my shaft. She bent down and lightly kissed the tip of my swelling cock. She took the tip in her mouth and slowly flicked her tongue around my cockhead and it was driving me wild! My cock felt like it was on cloud nine as I felt like all the blood in my body had rushed to this one organ. She released my cock from her lips and Miss Jenn joined the party with a little gift for me.

“This cockring should keep you nice and hard for us slut. We expect a hell of a show and don’t you dare cum until we tell you to or you will be sleeping with dan’s cock in your ass all night long!”

She smiled seductively as she knelt and expertly secured the cock ring around my smooth testicles trapping the blood and ensuring a swollen hardon for the foreseeable future.

Miss Meg slapped Dan directly on his asshole and told him to enjoy as she then took her spot on a chair next to the bed. She immediately opened her legs wide and began to play with her clit as the show was about to start. Miss jenn was in charge of the video camera and after zooming in on Miss Megan working her clit, she turned to me and said,

“Showtime bitch boi…time to win your emmy!”

I hopped on the bed and immediately slapped Dan right in the balls which set him yanking at his bindings and cussing at me like a sailor. Miss Jenn laughed as she came closer and inserted her panties in his mouth.

“Keep those in that naughty mouth of yours! Enough with the foreplay you silly bitches, we have more events planned so drilling must start now!”

I wasted no time lining up my cock and pressing on his exposed asshole. I have never fucked a guy before so this was a bit strange for me but I was not going to let my Mistress down by showing any sign of weakness. I forcefully pushed on the entrance and my cockhead slipped into his hungry asshole. Luckily for him, we had completed the dildo challenge about an hour ago but he was still relatively warmed up still. The tightness of his ass gripped my cock as I pushed further until I was about halfway inside him. I stopped slightly as he yelped and closed his eyes probably trying to block out what was happening to him. I told him to open his eyes and then without warning thrusted forward as my balls hit his ass with a loud SMACK. He jolted back and his cock slapped his chest as I completely removed my cock from his ass and again gave him my entire 8 inches deep into his boy pussy. The way his ass gripped my cock sent tingles up my spine as I now picked up the pace and worked deep hard strokes inside him. I picked his ass up a little bit so I could get a better angle and began thrusting downward so he would feel every inch of me. Watching him moan and tear up as I raped him gave me a sense of power that I wasn’t used to.

With Miss Jenn and Miss Megan cheering me on I fucked him balls deep as sweat began pouring off my body. With each slap of my balls onto his ass he let out a louder moan than before which motivated me to go harder. Miss Megan ordered me to work his cock so I grabbed onto it and quickly worked his shaft as if it were my own. With his face so close to his cock I imagined jerking him off and then watching it shoot all over his face but Miss Jenn ordered me to stop right as I got him to the edge.

“Time out! Batteries are dead, I need some new ones…brb!”

She quickly darted into the living room to find her spare batteries as I pulled from his ass and tried to regroup. I was actually thankful for the break as I was getting very close to cumming and the thought of accidently discharging and then having to sleep with a cock in my ass was not something I wanted.
Miss Megan removed her fingers from her pussy and walked up to the bed. She inserted her fingers into my mouth and I licked them clean. She tasted so good and I could tell she had already orgasmed from watching us. An idea came to me as we waited for the batteries and I asked Miss Megan her thoughts.

“Miss if you don’t mind, can we untie him please? He looks uncomfortable and I have a different position in mind.”

“Sure slut, go for it. But it better be hot…or it’s your ass!”

I untied Dan’s legs as they collapsed onto the bed and I’m sure they were feeling numb. He glared at me the entire time but I think he appreciated my suggestion. Miss Megan ordered me to remove the cockring and I did as instructed. She warned me that if I got soft at any point I would be the one getting fucked.

Miss Jenn returned and was confused about why Dan was untied.

“I asked Miss Megan if we could untie him and she gave permission. I thought for the last scene that Dan should prove how much he likes my cock by riding it. I know if it were me, I would be eager to show you what a slut I am by riding cock without being tied up”
I winked at Dan as I said it and both Mistresses laughed and agreed with me.

I laid on my back on the bed with my cock standing upright and Miss Jenn ordered Dan to mount. I could tell he was pissed about having to do this but I learned in previous sessions it’s never a good idea to disobey your Mistress. His back was to me as he roughly grabbed my cock and guided into his asshole as Miss Jenn began the recording.

“You have 5 minutes to ride him, Dan. If you get him to cum, you will be rewarded. If not, he will finish on your face. Justin, you have permission to cum but if you do during the 5 minutes…….punishment awaits”

That gave him a little motivation as his ass swallowed my dick and he slammed down onto my balls. That sent a jolt of pain into my stomach as I realized maybe this wasn’t a great idea. I put my hands on his hips and made sure I could control his bouncing so he didn’t slam too hard again. I also didn’t want him to ride too fast or I would surely cum and have to face the consequences. He had other plans as he began bucking up and down and increasing his tempo. His insides were driving my cock wild as I could feel him gripping me.

Mistress announced that there were 2 minutes left and he again picked up the pace. I looked over and saw Miss Megan working her clit with her fingers and knew she was about to orgasm again. That was my big mistake…watching Miss Megan expertly work her clit as her perfect tits bounced ever so gently….I lost it and without warning exploded into Dan’s ass.

He felt the cum and tried to hop off as quickly as possible and he was off by the time I let another strand high into the air like a geyser. The room erupted as Dan collapsed to the ground with some of my cum oozing out of his asshole.

I looked at the ceiling as I knew I was going to be punished……