Winners & Losers

Both of us were eagerly counting our money hoping to win but in a way, hoping to lose also.  My friend Stacy and I had a bet.  We would play Monopoly for 1 hour and whoever had the most money wins.  The loser must then put themselves in self bondage while the winner has their way with them.  During the course of the game, the odds went up to 3 different self bondage positions.  What was even better was that we could tie ourselves up anyway we wanted, without having to worry about release mechanisms.  Butterflies filled my stomach as I counted my money, dreaming of what I might do or have done to me.  The money was added up and we both had a smile on our faces. 

We exchanged totals.  By $200…I lost. 

Stacy smiled and whispered “Get your self ready slave.”  She didn’t have to ask me a second time.

I went down to the basement where we had our toys waiting.  Our basement looks almost like a dungeon anyways.   I pretty much had an idea of what I was going to do so I didn’t waste much time debating, I went right to work.  I took off my clothes and put on a black silk bra with matching thong.  I put on my shiny black shoes with 4” heels and locked the strap on them tighter than normal.  I wasn’t planning on using any torture devices such as clamps or butt plugs because I knew Stacy had something nasty planned for me.  The excitement was building really fast and I wanted so badly to play with myself right there but I held off.  

Focusing on what I had to do, I grabbed some bondage gear and went to work.  I stood in the center of the room, directly under an eyebolt that hangs from a beam on the ceiling.  I placed a leather strap around my ankles and another just above my knees.  It was hard to keep my balance but I managed.  My hands would be locked in metal handcuffs that would be padlocked to the eyebolt, keeping my hands and arms well above my head.  I locked the cuffs to the eyebolt and placed a bit gag into my mouth, strapping it on tightly.  One final thing and I was ready for Stacy’s punishment. 

“Click, click”.  

My hands were locked into the metal cuffs and I was completely helpless.  I stood there for what seemed like 30 minutes, and still no Stacy.  I wondered if possibly she got hurt or something and there would be no way for her to release me.  I started to get a little worried but then I heard the door open and footsteps on the stairs.  There she was, dressed in red leather hot pants and a red leather bra. 

“Good job” she said with an evil grin as she slowly walked towards me.  Excitement filled me once again!

She circled me slowly, moving her hands softly over my body.  Needless to say I was getting wetter with every touch.  She caressed my breasts making the silk bra feel all the more erotic. 

“Time for your punishment slave.” She whispered in my ear.  A groan of excitement came from my bit gag. 

I watched her walk over to the table that our toys were on a pick up a riding crop.  She ran it through her fingers with a smile and walked towards me.  Without a word she began to whip my ass, the thong I was wearing provided no protection at all.  Slow strokes, fast strokes, both hard and soft, my ass absorbed every blow she dealt.  The pain got worse with each hit but I loved it all the more.  Moans rang through my mouth as my teeth bit down hard into my gag.  I wanted so badly to touch my wet pussy but there was no chance of that. 

I was completely at her mercy.

The whippings from the riding crop had stopped.  Stacy once again began running her hands over my body, but not in the places I wanted.  My eyes, wet from enduring the pain and suffering stared into hers.  I mumbled words that couldn’t be understood because of the gag.  She knew what I was asking.  

“Oh, no sweetie, you’ll have to wait for that.”  

She teased me by moving her hand close to my pussy, but never touching it.  She enjoyed watching me beg and squirm, trying to convince her to satisfy me.  Quietly she walked over to the table again, this time picking up a leather strap.  

“You need to feel more pain before you can endure pleasure.”  

Once again that evil grin filled her face and my torture began a second time.  The strokes were hard and painful.  My knees gave way and I was suspended by the metal cuffs.  My wrists hurt and I forced myself to stand up straight.  Stacy continued with the spankings, not stopping for anything.  My body thrashed all around and sounds of agony echoed past my gag.  I felt as if I was going to pass out when finally she stopped.  She unlocked my cuffs and I dropped to the floor in exhaustion.  

“Rest for a little, but don’t you dare pleasure yourself” she ordered.  “You have 30 minutes to get in your next position.”  

I laid there, my ass stinging with pain, my arms sore from being held up for so long and a thong dripping wet from my excitement.  The urge to make myself cum was so unbearable, yet I managed to hold off and get ready for my next self bondage position.
 
 
 

12.10.03