The Bet 67

God, she looked good.

Sara came walking out of the bedroom with her silk robe slung loosely around her shoulders. It was open lewdly in the front revealing her nudity. I couldn't help but stare... admire... The click of her heels on the hardwood floors made me look down. I saw she was wearing the 4-inch stiletto heels she liked to wear in bed. Or maybe I should say she liked to wear them because she knew they'd get me into bed. I looked back up at her face as I felt the blood rush into my cock. I fumbled for the remote and turned off the game quickly before rushing over to her.

"Wow, what's the occasion?"

"Does a girl need an occasion?"

I chuckled and then leaned into her. I wrapped my arms around her body and brought her in tight to me. We kissed passionately. She reached down and traced the outline of my erection with her fingers. A low moan of approval escaped from deep in her as we kissed.

Sara was the one to break off the kiss after a few moments.

"Come to the bedroom, I have a surprise for you."

I was excited. We'd been dating for a couple of years and got engaged five months ago. Since our engagement, she had become much more confident and sexually adventurous. She had blossomed into this amazingly exciting person. These changes manifested in many ways and I'd noted her becoming more assertive throughout our relationship. At first, I'd resisted and tension arose but she managed to slowly make me more at ease with her stronger will. Little things like making the bed or doing the dishes were now de rigueur whereas a year ago I would have rolled my eyes at her asking me to pick my clothes off the floor.

As we walked into the bedroom she pointed to the bed indicating for me to lie down. I quickly disrobed and then lay down with my hands behind my head.

"Turn over." Sara said.

"On my stomach?"

"Yes."

I was surprised but did as she said.

Soon I felt her fiddling with something at my ankle. I looked over my shoulder and saw her putting a leather cuff on the ankle.

"What are you doing?"

"I want to do something a little different tonight. Let me tie you up."

She sounded a little nervous... a little unsure, but nevertheless she moved with purpose.

I was again surprised but brooked no dissent. We had played a bit with bondage but it had always been pink handcuffs and silk scarves. The leather cuff felt much more solid. Sara had become more assertive in bed recently but this was more than I would have ever expected. A few weeks before she had caught me off guard at dinner by telling me she had noticed I seemed more sexually excited than normal when she took over. It was true but I hadn't realized she had noticed and honestly, I felt a little embarrassed about it. I had stammered a bit and tried to change the conversation but eventually I admitted I did like it and was open to her being more dominant in bed.

"Scoot down a bit, baby."

I did as I was told. Soon my ankles were hanging just over the foot of the bed. Both were cuffed and while I couldn't see what was going on too well, the immobility suggested the cuffs were attached to the bedposts.

Sara moved to the front of the bed and repeated the exercise with both my wrists. Once she had finished she admired her handiwork a bit.

"Try to get free."

I struggled a bit but it soon became clear that these bindings were the real thing.

"Shouldn't you have done this with me on my back?"

I didn't understand why she wanted me tied down spread-eagle on the bed with my business end unavailable.

"Not yet, baby."

It began to make a bit more sense as she placed some big pillows against the headboard and then sat down in front of me. Her pussy was right in my face. Instinctively, I reached for it with my mouth but I couldn't quite get there. I didn't have to wait long though as Sara slid down just a bit and then wrapped her legs around my head to bring me in.

She gasped a bit as my mouth touched her sex. Fuck, she was really wet already! I tried to tease her a bit, gently tracing my tongue along her outer lips but she had none of it. She pulled me in tighter and I could feel her stilettos digging into my back. Both hands grabbed chunks of my hair and pulled me in further.

I concentrated on her clit. I usually took my time getting her worked up but it was clear that wasn't necessary. I moved my tongue rapidly on her in little circular motions, making subtle variations in speed and pressure to gauge her response. It didn't matter. She was so excited that everything worked.

Her moans got louder and I could feel my erection poking uncomfortably into the bed as her arousal fed mine. I extended my tongue deep inside of her and was rewarded with a copious flow of her juices. It wasn't going to be much longer. Soon she was bucking against me wildly and her breathing became ragged. I moved back up to get her clit in my mouth as her pelvis gyrated all over my face. I sucked on the little petal as hard as I could, using my teeth to bite ever so carefully. She came with an explosion. It had only been a few minutes but my neck was already sore from pleasuring her in this awkward position.

After her orgasm she got up without a word. I could hear her in the bathroom but I couldn't see much as it was hard to look over my shoulder. I put down my head to rest my neck and waited for her return. I tested my binds again and it was clear these things were legit. The cuffs were thick leather attached to a solid chain that snaked its way around the bedpost.

I was relieved when I felt her return with a shift in the bed. I felt her weight as she straddled my lower back.

"What the fuck?", I gasped as I felt something cool on my ass.

Sara laughed at my shock. "Remember this?" She didn't sound nervous anymore. I sensed the orgasm had soothed her nerves and that my acquiescence in pleasuring her had established her control.

I could feel her gently probing my ass with something solid. I quickly realized that the cool sensation was lube and she was using the butt plug I had bought a few weeks ago!

"What the hell are you doing?"

"Don't worry, I'll be gentle. It won't hurt... much."

I realized these were my own words being used back at me. I had fucked her ass for the first time about two weeks ago. Funny story about that actually... but we'll get to that later. I bought a few toys at the time to loosen her up and apparently Sara had gotten into the stash.

"I'm not sure about this."

"You were pretty sure about it before!"

"That's different."

"Uhhh." I let out a little grunt as she slowly pushed it in.

"In what way?"

"It just is."

She pulled it in and out a few times before sliding it all the way in again as though to demonstrate my argument carried no meaning to her. The toy felt huge inside of me.

"Is that the big one?"

"No silly, it's the little pink one. Do you think I'd start with the big one?"

The implication that there was more to come hung in the air as she shifted back around to the front of the bed again. Sara presented her sex to me. Once again, there was no hesitation as her legs wrapped around my head and brought me in. I enjoyed going down on her but it had always been as a prelude to sex and I'd certainly never done it twice in rapid succession like this. Her forwardness excited me enough to distract me from the discomfort in my ass.

"Look up at me."

It wasn't easy to do but I strained to look up into her eyes.

"Keep that tongue of yours working." She'd rarely used a condescending tone with me before so I wasn't sure I had heard her correctly. As she continued it was clear something was up.

"I have something important to tell you. I don't want you to talk. You are just going to keep licking me."

"Do you understand?"

I pulled my neck back a bit to mumble a weak yes. I wanted to ask her what the hell was going on but she pulled me back in before I could get any more words out.

"A little slow, huh? I said you aren't going to talk."

I could feel her stilettos digging into my back to drive her point home.

"Any question I ask you is rhetorical. I know the answer and so you'll just keep that pretty little mouth of yours doing what it's meant to do. Got it?"

This time I just kept on licking. She was very wet and smelled strongly of excitement but at the same time seemed poised and clearly wasn't close to orgasm.

"Gently. Long, slow strokes. There's no rush... we may be here a while."

She had never directed me before so boldly. I was a little perturbed but followed her instructions.

"Good boy, just like that."

"Something funny happened last weekend. When I was out with the girls, Jenn asked me if I've ever taken it up the butt before! Isn't that weird?"

She paused to make sure I kept licking her. I could see a brief smirk of satisfaction on her face as I followed her instructions not to talk. My neck and head were getting sorer and sorer.

"I've known Jenn for 6 years and the first time she asks me about anal sex is a week after I did it for the first time. I didn't think much of it at first. It just seemed like a weird coincidence but the other thing that bothered me was it just seemed so out of place. She was trying to be nonchalant but it just didn't seem like something she would ask. Like maybe someone put her up to it? But who the hell would put her up to it? Only her asshole boyfriend would do something stupid like that but he'd just ask you at your poker game. So then I think, maybe she knows and is just confirming."

"I figured that had to be it. You must have bragged to Jason and he told her but she wouldn't believe it until she heard it from me. I was so pissed when I figured that out."

I was taking all this in. I didn't know what to think. I just kept trying to please her as though that would make this all go away. "Keep looking at me."

My eyes and neck were killing me but I strained upwards to keep looking straight in her eyes. I had never felt inferior to another person before, but at that moment I did. I felt completely subservient -- being made to please her and hold her gaze while she vaguely admonished me. It was a surreal experience. The erection that had abated when she violated my ass was returning. I was glad she couldn't see it.

"But then, get this. Stephanie overhead our conversation and comes over laughing about how hard Joe has been trying to assfuck her for the last few weeks. Practically begging her. Next thing I know, Austin is saying just about the same thing. Then I realize they are all attached to men you play poker with. Aren't they?"

She remained silent for a few minutes.

"I was furious because I realized you must have all had a bet and Jenn was asking me in order to get confirmation to Jason so you could collect."

She stared straight into me. I was too scared to look away from her and buried my tongue deep inside her as though to beg mercy. Did she really figure all this out on her own or had someone squealed?

"Keep licking me the way I told you... yes, like that."

"But then I calmed down because I knew you would never pull a total asshole move like that. Right?"

She actually looked away for a moment. The condescension in her voice had been replaced by pain.

"I mean, the man I love, the man I am going to marry would never... would never do something like that to his fiancé."

"Right?"

I kept licking.

She smirked again and the pain left her voice. She was more matter of fact now without condescension.

"Because you know if I ever found out you had done something like that it would be totally over between us. Just over. No questions asked."

Was this it? I felt scared. All I could do was concentrate on licking her and maintaining her gaze.

At that point she lay back and relaxed a bit. She closed her eyes and began to concentrate on her pleasure. She brought me in closer and her breathing slowly became heavier. I placed my mouth over her clit and began sucking it in. It began to swell between my tongue and lips and a gasp left her lips. She started bucking again but I could tell she was a bit numb from the prior orgasm. This time would be work.

I kept sucking on her clit. At times I would stop and use my tongue alone to apply pressure. I tried to enter her with my tongue as before but she told me to stop and concentrate on her clit.

As my tongue tired I had to move my entire head to create the movement she wanted. My neck was killing me but stretching it a bit helped. I could taste her juices getting thicker and this gave me a second wind as I knew it meant she was nearing her climax.

I kept at it with vigor and was eventually she was cumming again. The orgasm was much slower and more drawn out than before.

Afterwards she just lay there. It seemed like an eternity. She began to gently rub my head with her hand and I was grateful for the affection. I took it as a sign that as mad as I thought she might have been things were probably not over between us. Words kept running around my head but I couldn't think of what to say. I wasn't sure if I was even allowed to talk. How could I not be allowed to talk? Anger welled up in me briefly but I calmed myself down. I wasn't in a position to yell at her and any misstep now seemed like it would have disastrous consequences.

She reached over into the drawer on her nightstand and fumbled around for a while before leaning back over and placing a blind fold on me. I was grateful for the anonymity.

She then got up again. I maintained my silence. She didn't say anything as she moved around the bedroom for what had to be at least 15 minutes. Was she preparing something or just giving me time to think about what was going on? The suspense was eating away at me.

I finally felt her straddling my back again. She yanked the butt plug out of my ass and before I had a chance to react she shoved it back in.

"Uhhhh, fuck," I muttered.

She hadn't shoved the same one back in. It had to be the bigger one because my ass felt like it was on fire.

She slapped me lightly on my ass and said in a joking manner, "remember, no speaking." I was grateful for the lighter tone in her voice even at the pain increased in my backside.

She shoved the plug in and out of me a few times, more gently than before. I kept quiet other than a low groan between clenched teeth. I didn't like where things seemed to be going but felt powerless both emotionally and physically to stop things. 

Sara slowly twisted the plug all the way into me and gave it a few light taps to make sure it was in to the hilt. Each tap took my breath away. I thought of asking her to please stop but I couldn't get the words out.

Sara got up again and wandered around the room for what seemed like another 10 minutes. The room was deathly quiet the whole time. I concentrated on breathing quietly in order to keep my focus off my ass and slowly stretched my neck and jaw to get the kinks out.

When she climbed back on the bed she assumed her prior position at the head of the bed. I still couldn't see her but strained forward a bit to taste her again. My neck and tongue felt rested so I welcomed the opportunity to please her again hoping foolishly that it would make amends. At the same time I was fearful that I couldn't keep this up much longer.

She stopped me though... I felt her hand on my forehead push me back a bit. She took some time to get herself comfortable.

"Get to work again baby." 

She pulled off the blindfold as she said it. The light was low in the bedroom so it didn't take long for my eyes to adjust -- instead it was her position that took me aback. She was no longer sitting in front of me. Now she was kneeling on the bed facing away from me. She was leaning onto the headboard with her back arched obscenely in a way that made it clear what she expected. I could see her little asshole right in front of me.

This was too much. I had done it before but not with Sara. Not with my fiancé. Not like this. But she kept backing into me and I felt like I had no control of the situation. She knew about the bet. I was sure of it and she would only feign ignorance so long as I did her bidding. In a moment I chose not to end the charade and stuck my tongue out to gently lick her asshole. I pulled back as soon as I made contact but the taste was OK. A little musky... but also sweet. I placed my tongue back on her and let out a low moan of supplication.

She responded with a moan of pleasure.

"Oh God... that feels good." I couldn't see but it seemed like her hand was busy rubbing her clit as I worked on her backside.

"Fuck, I really like that."

She reached back and pulled me in closer. I began to probe gently with the tip of my tongue to moans of approval.

The aching in my neck and tongue returned much sooner than I expected.

"Mmmmmmmm."

As her rosebud wettened from my saliva it brooked less resistance. I probed gently with the tip of my tongue. I was scared to go much further but Sara's moans of approval made it clear that that was what she expected. She pulled me in tighter with her hand. Once my tongue got past the first bit of resistance it slid in easily.

Soon my tongue was rapidly shooting in and out of her little asshole.

"Yes! Yes!"

She had several brief orgasms in rapid succession. I was grateful these came much more rapidly than the last one. She slowly regained her cool. Her hand stayed on the back of my head keeping me at my task -- now it seemed more as though it was an indicator of my status rather than a sexual act.

"Just lick, OK? In little circles. Mmmmm, yeah. That feels good."

"So where were we?"

"Oh yeah, the bet... Everyone was convinced there had to be a bet. Jenn, Steph, everyone.... Everyone,but me that is. Like I said I knew you would never do that to me. "

"It was funny because they were all so mad but then I had a great idea!!! I was thinking about that Vegas trip we have coming up and I figured I'd bet all my friends that I would be the first to nail her man in the ass! I got everyone up to $500 a head -- it was so easy given how emotional they all were. Think about it -- that's a $3000 pot. That'll pay for the plane, the hotel, a show and we'd still have a grand to gamble with. And all you have to do is what I just did for you. Well maybe a bit more... my cock is bigger than yours." The words stung just as they were designed to.

"I know I should have told you about the bet ahead of time but I think as long as I tell you about it before I try to fuck you then it's still consistent with an honest, open relationship. Don't you think so?"

My tongue probed into her ass as a sign of acquiescence. I was scared. I didn't see any way out of this.

"Good, I know how competitive you are and so as soon as we made the bet I knew you'd want to win it!"

She began to shift her weight and turn around. As she came to face me I found myself staring straight into a purple phallus arising from her pubis.

"So, I went to the store today and talked to a woman there. She sold me this thing. Isn't it cute! She told me it'd be perfect for what we have in mind. Look this end fits in me."

She pulled the dildo away from her and showed me a smaller end that fit in her vagina. She put it back in and began to lightly slap my face with the dildo.

"Isn't that clever? I hold it here at the base and then... well I bet you know where the business end goes."

"The lady told me that if you got me real excited I might even be able to cum when I fucked you. Well, that magical tongue of yours has done a great job getting me excited. And see, this part here rubs against my clit when I'm fucking you. She said with an enthusiastic, vocal partner who bucks back against the dildo sometimes you can get just the right pressure to orgasm. Isn't that crazy? I really want to fuck you until I cum."