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I've always been a bit of a gambler, always liked the thrill. I bet on games, play cards, whatever. Sometimes it's for money, sometimes dares, sometimes to get others to strip. I wasn't great, I end up losing about as much as I win, but I loved doing it. It has stripped me naked in a room full of nothing but guys and it has paid my rent for months at a time, it all depends on my luck. And lately I have been having some good luck.
My name is Tara, I'm a natural red-head, I'm 24, 5'11 and I'm pale white with freckles. I work at home, computer technical boring stuff but at least I set my own hours. Means it doesn't matter if I stay out all night.
So the other night I was talking with a friend Phil about this Sunday's game. We get pretty heated about it, he is sure I'm wrong and I was just as sure he's wrong. So, feeling lucky, I tell him to make a serious bet. He says that if he's wrong I can have his car, and if he's right then I will be his slave for a weekend. I thought it sounded good, I thought I couldn't lose, so I took him up on it.
Turns out I was dead wrong, he had inside information and had made a killing with anyone willing to bet with him. Now I had to be his slave for a weekend and I am not sure what all that means. He showed up with the worst grin on his face I had ever seen. I tried to ask him what he meant by "slave" but all I got was the instruction that I should be ready to start at any time in the next few days or weeks. I didn't seem to have too much of a choice so I agreed and told him I'll see him then.
That day came nearly two weeks later when he came knocking on my door with his big hockey bag full of stuff. He handed it to me and told me to go put it by whatever bed he would be using giving my ass a good slap. I was already begging for the whole thing to just be over. But I but his oddly heavy bag away, then did a whole list of other chores. I made him a late breakfast, got him a drink, cleared off the couch and turned on the TV.
"So," I asked, "what exactly is the plan, what am I supposed to do as your slave? I'm not going to just do anything you ask am I?"
"Well," he said muting the game, "how about this, sure you can refuse something too crazy. But, if you do I'll be here for the whole three days. If you do everything, I'll leave in half the time. Think of it like another bet, you can win the other half of your weekend back. But if you can't take what I dish out then I get you for an extra day. Think you can handle it Tara?"
I thought about it for a while. I didn't know what he meant by "too crazy." I just asked "not going to make me do anything illegal right?"
"No, but anything I can think of. Think you can take the bet?"
I was a little worried, but that same kind of excitement when I make any other bet. "Deal, do your worst and I'll be home free by 8pm tomorrow."
"That confident eh? This should be fun, just don't expect me to go easy."
"Oh I don't, bring it on" I said.
He seemed to be contemplating. "Bring me my bag."
I did and set it at his feet and walked back to the blinds in front of the glass door that lead to my ninth floor balcony. He opened it up and seemed to look for something. He grinned as he apparently found it.
"Ok, strip." He said as he looked up at me. "And make it sexy."
What! Oh so that's how he's going to play it. Well I'm not going to lose at the first minute of our bet. I started with my t-shirt, bringing it slowly up and eventually over my head and threw it to the floor. Then I untied the strings of my sweatpants, I took them off as gracefully as I could but I still almost tripped getting out of one leg. So I stood there in white panties and cream bra. I tried presenting myself hopping this was enough stripping for him.
"keep going" he murmured, apparently wanting me totally nude.
I started with my bra; I walked right up to him and bent over, giving him a great view of my c-cup cleavage. I stood up, reached behind me to unhook it. Slowly, trying to tease him I let it come off, eventually throwing it back to the rest of my cloths. I turned around; showing my unimpressive (to me) flat and skinny ass as I slowly worked my panties down my leg, letting them eventually fall to the ground before I kicked them to the rest of my cloths. I turned around to see a devilish smile looking up at my naked body and I got a little worried.
He stood up and shoved me around so I faced away from him. Then everything went dark as he placed some kind of hood over my face. I reached up to feel it; it was some kind of leather, holes at my mouth and nose but that was it, there was nothing where my eyes should be. I felt him tightening it at the back of my head until I heard the click of a lock. I reached back to feel a locked zipper covering what felt like laces. There was no way I could take it off and no way I could see anything with it on.
"What the hell?" I asked, thankful I could at least still talk.
He didn't say a word, he just grabbed me and forced my hands together behind my back.
"Owe, you're hurting me!"
I felt my elbows being pulled together and cuffed there. I heard the clicking of handcuffs and the cold steel digging into my skin a bit above the elbow. Then a second set of cuffs were added at my wrists. My arms were totally immobilized.
"Give up yet?" Phil asked.
I thought about it, I already couldn't see, I couldn't move my arms and I was totally naked. But I was always a little too prone to let it ride. "What, is this it?" I asked, taunting him. "You'll have to do a lot better than that if your trying to get me to quit! I am you little slave, and I will do what you ask."
"Good to hear" he said. He seemed to just be wanting permission to go further cause he wasn't acting done. He put some kind of collar around my neck which I also heard click shut with a lock. He attached a leash of some kind to the front as he pulled me forward with it. He sat me down on a chair as he put strange boots on my legs, all of this while I am blind.
"Stand up" he ordered. As I did felt the height of the boots, they where the steepest stilettos I had ever conserved of! They must have been 6-7" tall. I tried to spread my legs to balance myself but I found that my legs were chained together with only a little bit of slack. I would have fallen over if Phil didn't grab me as I tripped. Of course he took the time to feel me up as he steadied me.
As he let go he started to pull the leash again. Eventually, I started getting my balance and walking forward.
"Are you getting the hang of it?"
"I guess, it's really ha.." I started saying before Phil shoved something in my mouth. It tasted like a big rubber ball but I absolutely could not spit it out.
"mm you look good!" Phil says as he started to rub me all over. He started massaging my breasts and slowly moving one hand down my stomach reaching the edges of my now wet pussy. I was starting to really enjoy the attention. I even started to breathe a little heavy into my gag. It even made me forget about my sore arms and the hood. I just fell into the moment, enjoying every touch, even hoping for more.
I think Phil caught on, cause just at that moment he plunged two fingers without warning into my wet pussy. I leaned into it and moaned, even if the moan was stifled. He continued to grab my breasts and play with my nipples using his other hand. It felt so good! All I felt was good. I was grinding his finger making every thrust deeper and faster. I was moaning threw my gag as I started getting closer to a climax.
"Do you want to cum slut?" He asked.
I tried to say yes, but with the gag all I could manage was "Jjreuss"
"What I couldn't hear you."
"Rueesz, Troed Rueszz" I tried so hard to beg yes, but the gag stopped me.
"I guess you don't want to cum" he said as he pulled away, leaving my pussy nearly dripping and just so close. I can just imagine the grin he was giving me now.
He pulled me by the leash and told me to kneel. He took out my gag and I gasped to catch the drool.
"now I want you to listen to where I am, find my cock, and suck it in your mouth."
"I'm not doing that! This isn't just a free license to have sex!"
"Well you didn't seem to object when you were getting pleasured. And besides, are you really giving up over a little blowjob?"
He had a point, I was already naked, he had already been fingerfucking me and I certainly fucked his fingers back. I guess the next step isn't worth losing the bet.
So I leaned my head forward, trying to feel for something. I felt a leg and I scooted forward to move my head up and up. Finally I found his cock out. I opened my mouth and looked for the head, licking whatever flesh I passed by. My licking seemed to make it twitch and I used that to find his head and I just went to work. I felt the back of my head getting pushed down and I started to gag. I tried to pull up but he wouldn't let me.
I tried to pull my arms free but those cuffs made it impossible to move them. I tried to get my legs to move but they wouldn't spread and with the heels I couldn't get up. I just kept gagging and gagging until I started to lose consciousness and pass out.
When I woke up I opened my eyes and I could see again. The hood was off. I was laying in my bed tried to turn over but my arms and legs wouldn't move. I looked up and saw that my arms and legs were cuffed to each side of the bed. I was spread naked and vulnerable.
The only thing I saw was a note taped to the ceiling:
Well I thought you could use a rest.
So I laid you down to relax for a while.
You're free and out by 8pm.
But that is still a long ways away.
I hope you get comfortable.
Though I may come back to help with that.
But at least you won this bet!
I looked at the clock, and it read "11:04 pm"
I was pissed at first but after nearly another day of daydreaming in cuffs, I thought maybe I should lose a bet again.