Lost Bet Leads To Forbidden Affair

You had a surefire thing in your mind, and so willingly made the bet.

You knew the stakes, and agreed to them as you were certain that you had this one in the bag.

This time it was a bit more than just the normal bottle of wine or sexy picture.

This time my stakes were much higher.

This time the bet was for you. For one night of your naked body to do with whatever I pleased.

Your stakes included a dinner at the restaurant of your choosing, and you could get whatever you wanted, and you intended to make it costly!

The way I saw it, it was a win, win.

Your unbeaten team lost. Somehow their offensive line opted to take the 4th quarter off and as such, your fate was sealed.

You knew this was unlikely, but made the bet anyway. To be paid at sometime in the future when both of us had the ability to step out of our every-day lives.

You made the bet. You lost the bet. You fully intended to make good on the bet.

Time passed and while it was not necessarily in the forefront of your mind, every so often I reminded you of the fact that there was a debt to be paid!

With some maneuvering, I made sure to be in the same city as you for the same meetings. You knew it was not by chance, but made your peace with the fact that the time had come.

I got a room at the same hotel as you and as fate interviewed we were actually put on the same floor.

A full day of meetings followed by a group dinner did nothing to set the mood, but I asked you out for drinks afterwards and we met in the hotel bar.

I gladly paid for your stellas and your wine, sipping slowly on my jack and coke as the evening wore on.

I then told you it was time and that in 20 minutes I wanted you on your bed, naked and face down with your ass presented to me in the air.

You laughed, while chiding me for being too direct. I simply responded that I have waited for this for far too long and was going to have you on this night!

You gave me a key and told me your room number.

I walked in to find you just as I had requested. You had all the lights off, save one and it put out just enough light that I could savor your beauty.

I started by lightly tracing my fingertips down your hips, over your lovely ass and down the outside of both of your legs, kissing the small of your back as I caress each side of your amazing little ass.

Taking my time as I have you in a position that I have longed for.

Slowly spreading you apart so I can see your tight little rosebud and view that silky smooth pussy for the first time.

I know that you like to fuck, but I may never get this chance again with you and so I am going to really enjoy the experience of ever second of my time with you.

Having you spread wide, I begin to kiss closer and closer to your most sensitive parts. Using my tongue to slowly taste your swelling pussy.

You taste amazing and as I am savoring you, I hear you start to moan softly and I know that you are finally in the moment.

I can't help myself as I begin to use both my tongue and my fingers in order to fully bring you pleasure.

And... since you are mine tonight, I think it is also fair that I bring you a little pain as well!

I know you are not an anal plug girl, but you lost a bet and so I have you tonight. I have you!

I bought a special hand-made glass plug that is tiered, starting out small and staging up to somewhat less small. You turn to look at me and ask me what I am doing. I tell you what I am planning and you protest until I remind you that you made the bet and are mine!

With that I add lube to the plug and slowly slide it into your pussy.

I find that you are soaked already and that knowledge puts a large smile on my face. I love that you are enjoying this and that increases my desire to keep going.

I continue sliding your glass plug in one stage at a time, hearing you breathing heavily as it slides all the way to the hilt.

At this, I start to apply my tongue, slowly pulling the plug in and out of you and lapping at your spread lips.

Your juices are incredible and I simply have to have more.

You are moaning audibly now, completely lost with having me take you.

I slide the plug all the way back inside you and leave it there, kissing each of your ass cheeks, followed by a few hard slaps on each side of your ass.

I had no idea this was something that turned you on, but you love it. You are filled with a cold glass plug providing pleasure and the sting of my hand on your bare ass providing you pain brings on your first orgasm of the night.

Your fingers find your clit and start to rub along each side of the glass plug as you ride the ecstasy of the endorphins now filling your brain.

I wait until you have come down a bit and once again spread you wide, this time allowing my tongue to find its way to trace around your ass.

You again moan softly, enjoying the feel of a new lover as I apply some lube so my finger(s) can enter you with ease.

After I have your ass loosened up some, I remove your plug from your pussy as you know what is going to happen next, you spread your legs a bit wider, reaching back with both of your hands to spread your cheeks.

Your juices are now leaking down your legs and this entire view is one of the most sexual scenes I have ever seen. My cock aches to have you. But not yet.

I lube up your glass plug again and press the cold tip against your ass. You moan in pleasure, knowing you are about to take a lot inside your small body.

The first and second stages both go in easily but it is clear you are full as I move in and out with the plug at the second stage and began to build up another long, powerful orgasm. I continue to work it as your legs begin to quiver with the intensity, but I don't let up.

Finally getting to the last stage of the plug so it is fully buried in your ass and I can tell that you are a little worried about what is going to happen next.

I quickly remove shorts, placing my cock between your ass cheeks and liberally apply lube so I can begin to slide between them. I love this feeling and take a mental note of how sensual and sexy you look right now.

I know you are filled with your glass plug, but my cock can no longer be held at bay and I begin to slide up and down your soaked slit.

The sensation of having the plug inside you and knowing that my bare cock is about to penetrate your pussy sends the right signals to your body and you feel another orgasm start to build.

I continue to tease, but my cock is painfully hard and I am pretty certain that I will not last long once I finally enter your body so I am taking my time.

You finally tell me that you need me to fuck you already and I can't wait any longer. Sliding the entirety of my cock into you in one solid push.

You feel so incredibly good, and I close my eyes focusing on every sensation as I begin in earnst to fuck you.

I love the sounds of your moaning and feel as your fingers once again are playing with your clit, but also sliding up both sides of my cock as I thrust into you again and again.

In turn, you are loving this. Everything is so tight and having a plug in your ass and a cock in your pussy is a sensation unlike you have experienced driving you into overdrive with every thrust as it pushes against your plug.

I tell you I am close and ask you where you want me to cum.

You tell me right where I am exactly where I need to be as you thrust back against me.

My orgasm is intense as I moan loudly as I erupt inside you, continuing to push into you until you have fully drained my balls.

I stay buried in you for some time, until you pull off and lay on your bed.

Your legs are still spread and I can see Milky cum is working its way out of your pussy. It is one of the most sexy things I have ever seen in my life and I smile as I lay next to you and pull your face into mine, kissing you deeply.

You tell me you need a break as you are getting sore, but that we are not done. I reach back and slowly remove your plug, setting it on the nightstand.

You kiss me again and stand to go get some of my cum out of your body and I again have to gasp with the sensual nature of your naked body.

I can't wait for round 2.