It all started with an innocent bet over dinner one evening. With nothing more than a quick check of the internet I had won the bet, but I was not ready to collect. That would wait for another time and place. We did not even decide what the reward was. All she knew is that she lost.
Weeks later, I decided it was time to collect. The kids were gone for the night and we would have the place to ourselves. If only she had known it was time to pay up, but that was part of the surprise. I spent the entire day thinking about the evening. Weeks of planning and preparation were about to kick into action.
Allison returned from a day of errands and I met her at the door. We unpacked the car and I decided it was time. It started simply enough with an embrace in the kitchen and a kiss. I then asked her if she had forgotten about the bet. She said "no", but I could tell she had not really considered the payoff and had no thoughts of paying up now.
"Tonight" I said. She gave me a puzzled look and did not quite know what to say. "I made plans for you to pay off the bet."
She replied with a sullen "oh" that was more like a grunt. She obviously was not excited. In fact, I started to wonder if she would play along. While she was looking at me, wondering what she had to do, I was lusting for her, knowing what she was going to do for me. Little did she know that it was more about her pleasure then mine.
I told her to relax and that I would explain later. I am sure that did not sit well, but I know it also left her wondering. The mystery had started.
The evening progressed into drinks and a special dinner. Since the theme for the evening was "hot", I went with the Caribbean theme. Fruity drinks, an island themed meal, and even a little desert (although that would not be the evening's only desert). She was loosening up, even though the evening was still early.
Next was a movie. I found one of her favorites. A few more drinks and I could tell she was feeling frisky. We still hadn't talked about the payoff, but she seemed to be more open. A joke. A little sexual innuendo. Maybe she was starting to think of ways to pay off? Little did she know that the evening was already planned.
With a few passionate kisses, it was clear she was opening up to the idea of a quiet night together. My plan was that it would be anything but quiet. We kissed passionately. We held each other close and enjoyed time we rarely had without the kids. Before long, my hands were exploring her like we were teenagers. Her breath told me she was enjoying it.
"Let's go upstairs" I said. "It's time to finish the bet we made."
She stared at me. Her look said it all. Her body was ready for more, but her mind was worried about what I might demand from her. A blow job? Anal sex? Something more kinky? Her thoughts were running wild, and while the passion of the drinks wanted to let go, her conservative upbringing was hanging on. I was loving every minute. I knew tonight was not about me. It was about her, but she had no idea.
I followed her upstairs to the bedroom, grabbing her ass several times on the way up. I could tell she was feeling horny, but I could also sense the tension. Fetish and kinky was not her thing and while we have always had a good sex life, there were boundaries. Tonight, boundaries would be crossed.
As we entered the bedroom, she turned, threw her arms around me and asked "what was the bet again?" She was nervous and sizing me up for how far this might go.
Sensing the anxiety, I asked "You don't remember?"
With that I gave her a kiss and headed to the bathroom to freshen up. She was stunned. You could have heard a pin drop.
"Oh god, what did I promise him?" she wondered.
I knew the truth - she had not promised anything, but the mystery of the evening was causing her mind to race, and it was racing to places she dare not go. How far would I make her go? Might she have to swallow my load? Or worse? There were so many possibilities.
Her heart was racing. Her legs were tingling. Her nipples were hard and even though we were in the sanctity of our bedroom, there was a strange mix of excitement, anticipation, and apprehension.
The anticipation was too much. She stripped right then and there. While she longed to know the bet, she wanted to be fucked. There was no hiding that as her body gave every clue. As I walked from the bathroom she was already laying naked on the bed. Her ample tits were calling me with rock hard nipples. Her eyes begged me. Too bad it wasn't time yet.
I joined her in the bed. As I lay next to her, she got the first brush of my hard cock. Nothing had happened yet, but I was so excited I was ready to pop. My cock was throbbing anticipating the rest of the evening. She stared me in the eyes and asked "so, what do I owe the winner?"
I did not answer at first. I nibbled on her ear with a soft moan and a kiss. I nestled my cock up tight against her leg, continuing to kiss her neck. She whispered in my ear "so what do you want tonight?". That just made it worse. I almost abandoned the plan right there. My balls were tightening, my cock was aching and her breath in my ear put me on the edge, but I held out. Tonight, I was in control.
As I pulled away from her neck, I gently caressed my hand across her stomach. She jumped. She wasn't ticklish, so I knew it was the anticipation of touching her bare pussy. But I didn't. Instead I pulled her closer. I looked deep into her eyes and kissed her softly. A long passionate kiss, my tongue intertwined with hers.
As we finished, I asked if she really did not remember the bet. By now, the bet was no longer important, except to me. Still, she answered. "I know I lost, but what did I promise you?"
"Nothing" I said and I kissed her again.
"Nothing at all which is why tonight is my night."
She kissed me again before I could finish. Hot. Horny. Wanting me now. "Fuck me" she said. As hard as my cock was, I passed on her advances.
"Not yet" I said. "Tonight is going to be different. Tonight you have to do what I tell you."
She gulped and stared at me for what seemed like minutes. Stammering, she asked "like what?"
I kissed her passionately again, my right hand caressing her breast as my cock pulsed against her leg. Her imagination was running wild. As we finished our embrace I whispered into her ear "you don't have to do anything but enjoy." Now, she was as confused as ever.
"I want you to roll over on your stomach" I told her. My plan was in full motion. She hesitated, but I think she felt better that I had not demanded something crazy, something she was mortified to try. She rolled over and all I could focus on was her sweet ass. Still as gorgeous as the day we got married.
I stood at the side of the bed and stretched her arms above her head. I began her massage with some lavender oil working the full length of both arms. She lay patiently enjoying the feeling, but wondering what was next. I took her by surprise when I pulled a necktie from under the bed. In a matter seconds, I had tied her wrists together - not hard, but just enough that she could not get free.
She was not into bondage, so she really wanted to resist. She looked at me trying to protest.
"Really?" she asked.
I kissed her softly and whispered "you lost."
Now it was full speed ahead. Tonight was about her feeling things she had never felt before, mastering her senses. I pulled a blindfold from the nightstand and straddled her back, her arms still bound in front of her. I put the blindfold on. She stirred as if she wanted to refuse but soon realized it was futile. Her anxiety was way up now. This was not her and she wanted out. I started to massage her shoulders giving her no choice. At the same time, I leaned down and whispered "trust me and it can be the best bet you ever lost".
While she wanted to relax, there were things going through her head. Bondage? Anal? A threesome? What? We had never ventured this far, so she had no idea where this might go. She wanted it, but was nervous what "it" might be.
I had one last element of surprise. Music. I put the earbuds in her ears and turned on some music. That confused the shit out of her. Depriving her of her key senses – touch, sight, and sound- would allow her to focus on what she was feeling. The fires would burn hotter than ever from her brain to her pussy. My cock was already yearning for more.
With my version of "fifty shades" in place, the full massage began. I dripped a few drops of the warm oil on her back. As I enjoyed the scent, I started to work the oil, kneading the muscles in her back to chase the tension away. She was starting to live in the moment and to forget about what might lie ahead.
I straddled her ass as she listened to the carefully selected music. I reached for her shoulders and her neck. With every long stroke she could feel my rock hard dick press against her. I would push hard up her spine to her shoulders, then down her shoulders under her arms stopping long enough to caress her tits which were pressed on the bed. I knew it was working by listening to each breath.