You Bet Your Ass 2

This story is based on real events and features my recurring submissive character, Rebecca. It's about anal sex, but due to the overall context of power exchange and female submission it is listed under BDSM. Only consensual (though edgy) acts are depicted. In real life, please take good care of your submissives and always accept no for an answer.

*****

Rebecca and I had been together for years and we knew our roles well. She reveled in being submissive and wanted the dynamic between us to be as realistic as possible. Although we knew the boundaries between play and real-world concerns in our relationship, we rarely needed to invoke them. We didn't even have a "safe word", which I'd insisted on in every other relationship. Rebecca liked having to simply trust my judgment and it reinforced the idea of her choosing to live in a situation she doesn't control.

So I got as much sexual use out of her as I wanted, whenever I wanted. Rebecca stayed naked and exposed much of the time at home and did a lot of begging for the orgasms she was only allowed to have once every week or two. Life was good.

I thought of Rebecca as a kind of extreme athlete. She derived a great feeling of accomplishment from being submissive, especially when she was set a difficult task or ordeal. Although I preferred exploring the emotional side of her submission, Rebecca also needed to endure some physical pain. Every so often, a few times a year, she would beg me to restrain her and deliver a good thrashing. She would begin hinting about needing an "attitude adjustment", and eventually provoke me by breaking a minor rule. She loved being threatened with increasing consequences - a hand spanking, followed by strokes with my belt if it didn't resolve the issue. Usually, Rebecca would persist in her misbehavior until I pulled out the big stopper, a black leather riding crop. A session with the crop was cathartic for her, and afterward she would be sweaty, sore and full of smiles.

But the crop isn't actually the end point of the consequences she might face. There is also the nuclear option.

I've had anal sex with several girlfriends. While anal has its moments, I personally can take it or leave it. The extra preparation and cleanup is a minor nuisance which, for me, usually surpasses the novelty effect. I've had a few girlfriends who liked anal and I enjoyed it with them, but it's not something I usually go out of my way to do.

Rebecca and I have anal sex only rarely, but I enjoy it with her more than I ever have before. She dreads it, finds it painful and humiliating and is always deeply proud of herself afterward for enduring it. When we are both in the mood to highlight her submission and need for pain, it's time to bring out the lube. I've found it best to threaten her with an ass fucking and then let her worry about it for a while.

For the past week Rebecca has been baiting me. Misbehaving more and more blatantly, obviously wanting to be put her in her place. On Wednesday I began hinting that her comeuppance was imminent. Her usual response is to get haughty and taunt me even more. Rebecca knows herself well and has told me when she enters this frame of mind she's looking for me to take charge. "Remind me how things work around here. Take me in hand. Do whatever it takes to wipe that smirk off my face!"

On Thursday I told Rebecca she was on thin ice. If her behavior didn't change, there would be a "correction" very soon. She again doubled down on the sarcasm. Yesterday (Friday) was the last straw. Rebecca woke up cranky and was uncooperative with our usual morning routine. "We're going to do something about this when I get home tonight," I told her as I dressed for the day.

She snorted dismissively. "Oh, really? Are you going to give me a stern talking-to? I'm soooo scared."

I stood silently and smiled back. Then I reached into a dresser drawer and pulled out two objects. I tossed one to Rebecca and she looked at me defiantly. It was the crop. "You know I can take that."

I sighed. "OK, then." I tossed the second object, which was a tube of lubricant. This broke through her show of confidence. She gasped and looked at me fearfully. "Wait... what? You mean..."

"You know what that means," I said menacingly. I advanced on her, backing her up until she bumped into the bedroom wall. Then I seized her by the hair and hissed in her ear, "I'm fucking your ass tonight. And you are going to take it like a good little BITCH. Understand?"

Rebecca swallowed and her voice took on a tone of conciliatory reasoning. "Michael, I'm sorry. I know I've been a little snippy lately. Can we just..."

"You're not talking your way out of this. You've been asking for it all week. Well, tonight you're going to get it." She shuddered, scared but also obviously aroused. "You are not to eat lunch today. Drink only water. Got it?"

"Michael, please!"

I pulled harder on her hair. "Do you understand?!"

"Yes!"

"Yes, what?"

"Yes, sir!"

Releasing her, I straightened my tie and smiled amiably. "See you tonight... honey." It drove her crazy when I called her that sarcastically. She watched me go, wringing her hands and looking anxiously at the tube of lubricant.

Twice during my work day I paused to text Rebecca and twist the knife a little.

"How are you, honey? Having a nice day?"

Her reply: "Hungry."

I responded with a photo of my sumptuous Thai lunch. Her favorite.

Later I reminded her to make some preparations for our evening - cook a nice meal for dinner, put towels down on the bed and insert her butt plug. She responded with a series of angry emoticons I did not attempt to parse.

I didn't even have a chance to open the front door that evening. As I reached for the knob the door was suddenly pulled back and there was Rebecca, looking nicely made up and eager to please. She took my briefcase, helped me take off my coat and put a drink in my hand.

"How was your day, dear?" she asked, leading me to a chair.

I grinned and took a sip of the freshly mixed Amaretto sour. "Not bad."

She beamed. "I'm glad. Let's put some on some music! Dinner will be ready in..."

"Strip."

"Wh... what?"

"You heard me. Strip."

Rebecca wrung her hands (she always does that when she's nervous or scared) and looked at me pleadingly. "Michael, I'm sorry I was a little disrespectful. Please, let me bring you the crop instead and..."

"You'll bring me the crop ALSO. But I said strip. Now."

Her chest was heaving. "Michael, please..."

I took her chin in my hand. "If you're not naked and in your display position in 30 seconds, I'll give you nothing but anal for a month." She froze like a deer in headlights. I repeated, "30 seconds", and clicked the timer on my watch. That snapped her out of it and Rebecca began tearing off her clothes. She made it with five seconds to spare.

I gave her a tap on the elbow and she raised her arms to assume the position for display. Hands on the back of her head, back straight, feet shoulder-width apart. Despite her erect posture, her eyes were down and defeated. But she hadn't given up all hope yet. She assumed her most dramatic, damsel-in-distress voice.

"Please Michael - I'll do anything!"

I shrugged as I circled her. "I know you will."

Her voice was growing more and more desperate. "I'll give you all the pussy you want! All day long!"

"You do that anyway."

Momentarily silenced, she tried a different angle. "I'll do... I'll do something really, really slutty! Something we've never done before."

I considered this. "Like what?"

"Anything! Punish me with something dirty and shameful." Her mind was moving fast, trying to think of a way to save herself from an ass fucking. "Make me perform for your friends. I'll strip and spread for them!" I shrugged again. "Cum on the floor and rub my face in it. And take pictures!"

"That's a thought..."

She brightened for a moment, until I said, "No. Sorry. I definitely want to fuck your ass. But I'll tell you what. We'll make it interesting."

She scowled doubtfully.

"First, bring me the crop."

Slowly, Rebecca lowered her arms and went to retrieve from the crop from the bedroom where we had left it earlier. She was walking a bit gingerly because of the butt plug. She returned and presented the crop to me with eyes cast down toward the floor. Wordlessly, I took her by the hair and pulled her to the couch. She knew from experience how to drape herself over the back and present her ass for a beating.

"Since you have a bigger ordeal coming, it will only be fifteen with the crop."

"Ten!"

"Twenty. I had taken off five because you put in your butt plug as you were told, but since you're arguing..."

Rebecca knew better than to continue this sort of exchange, as it would only lead to more strokes with the crop. She was occasionally in the mood to do that intentionally, but not today. There was only so much she could take.

The crop swished and landed. Rebecca took five silently, then began crying out with each blow. I didn't draw it out, wanting to move along to the main event. So I beat her quickly, turned her to face me and then sat on the couch in front of her. Rebecca was breathing hard and I could tell she was well on her way to sub-space. Good, that would make it easier for her.

"So, here's the game. We're going to play 'You Bet Your Ass'. Say the secret word and win a hundred dollars!" Rebecca looked at me blankly - too young to remember Groucho Marx. So was I, come to that. I waved away the thought.

"Never mind. Here's how the game works. I'll give you three minutes to suck my cock. If you can make me cum we'll just have dinner. But if you fail..."

She was hanging on my words.

"If you fail, I am going to ream your ass. And I promise you, I will enjoy making it hurt."

Rebecca knew I had good self-control. Despite being very talented at oral sex, the odds might not be in her favor. But she knew she wouldn't get a better offer. I reached for my watch and Rebecca sank to her knees. She had a fight-or-flight expression on her face.

"Would you like to take it out for me?" I asked sweetly.

She glared up at me. "You're a bastard."

"And you're a slut who is about to get ass fucked."

"We'll see," she said with as much bravado as she could muster while naked, on her knees and under threat.

I unzipped and took out my hard cock. "Three minutes."

She was thinking, wondering if she could work the terms of the bet to some advantage. "What if you..."

I clicked the timer. Rebecca stopped in mid-question, realized the seconds were already ticking away and dove down on my cock.

It was truly gratifying, seeing Rebecca give such a fervent blowjob. She was absolutely determined to do her best. She deep-throated me, rubbed my cock on her face and used her hand to help stimulate and hopefully push me over the edge. She had no shame and didn't even miss a beat when I told her she was making a complete slut of herself.

Not that I was completely free to taunt her. A blowjob from Rebecca is no small thing. She's talented and eager even when not trying to save herself from an anal assault. The best I've ever had, in fact. So I had to concentrate to avoid letting her get the upper hand. I tried to enjoy her wanton display dispassionately, which was not easy. I focused on calling out the time. "You have two minutes."

She grunted and forced my cock further into her throat. "Two minutes, 30 seconds." Rebecca sped up. "One minute." She re-doubled her efforts, clearly terrified she might lose this bet. At 30 seconds I knew I would make it. I counted down the final ten seconds out loud until the timer went off. Rebecca kept going and I had to take her by the hair to pull her off my cock. She looked like she had just been read her own death sentence. I looked her in the eye. "That ass is mine." I pulled her into the bedroom and tossed her down. "Give me the lube and lay on your stomach with your ass up."

"No! Please, not like this!" she cried dramatically.

Snatching the lube from the end table myself, I pushed Rebecca down onto the towel-covered sheets. Pinning her there, I pulled out the butt plug. "Spread your legs and keep still."

She was whimpering. "Michael, no!"

I shucked my own pants off and grabbed another item from the end table. I showed it to her. "Hey, I'm not a monster. I understand this isn't comfortable for you. Look what I got to help you through it." It was a thick leather strap. I smiled and petted her hair lovingly. "You can't bite down on this when it really starts to hurt. You're welcome."

Rebecca turned her head as far as her position would allow and gave me an evil look. "Bastard! YOU bite on it!" With that she gritted her teeth and pressed her forehead to the mattress.

I quickly lubed my cock and Rebecca's asshole, and so began her ordeal. Having reluctantly surrendered to the situation, she had the presence of mind to at least try to relax. The first moments were always the hardest. She winced as I slowly pushed in, then cried out twice. I held her shoulder firmly, preventing her from squirming away.

At this point, I was splitting my attention between the wonderful sensation of penetrating her ass and carefully monitoring Rebecca's reaction. So far I had detected no signs that she was reaching an actual limit. But a limit could be reached much more quickly during anal sex than with most other activities. She liked pushing herself, but I didn't want her to be actually hurt. Being the dominant has its responsibilities.

Rebecca was huffing and grunting as I worked myself in farther. Finally at my full length, I pulled back. She exhaled and then yelped when I pushed back in firmly. She told me later that it's always this moment when it gets truly real, when she knows she's being taken in her most private area and will just have to accept it.

I put my mouth to her ear again and taunted her. "I love fucking my little slut's ass. Does it hurt?"

"Yeeeeeeesss!"

I gave a firm push. "Good!"

She was whining into the mattress, but still seemed all right. I thrust harder for a moment, which elicited another yip. It was possible Rebecca would orgasm from this. That was allowed during anal, no permission required. Positive reinforcement, you see.

After a few minutes of this I pulled out, causing Rebecca to exhale with relief. The break didn't last long. I flipped her onto her back and moved between her spread legs. I had never taken her anally this way before. "I want to see your face this time."

I enjoyed watching her features contort as I again plundered her ass. She turned her head to the side, as if disassociating from the pain. This might have been worrisome, except that it's something she does regularly to highlight her sense of submission and humiliation.

"Are we going to have any more sarcasm from you?"

Rebecca shook her head. "No! I'll be good!"

I nodded and put my head down as I continued using her ass. It wouldn't take long for me to finish.

Moments later, as I was approaching my climax, Rebecca said, "Michael, I think I'm going to need to stop."

The tone of voice was different. It was real, she was reaching her limit. Not an emergency, but she really would have to stop. Then again, I was almost there. I made a quick judgment.

"Stay still. I'm almost done."

Rebecca gasped, but obeyed. I thrust into her for a few more seconds and then exploded. The orgasm began in the back of my skull, passed through my shoulders and then through my whole body. My entire being clenched with the sensation and idea of cumming into Rebecca's tight, submissive ass.

Rather than stay on top of her and bask in the glow as I would under other circumstances, I quickly pulled out. We were both out of breath. "You OK?" I asked?

Chest heaving, Rebecca looked up at me and nodded wordlessly. She continued breathing hard for a moment and then her mouth curled into a wicked smile. "You kept going."

I nodded.

"I really took it, didn't I?"

I nodded again.

She was beaming now. "I'm getting better at that! Aren't I?"

She was proud of herself. "Yes, you are."

"Shower. Dinner. Sleep. Please."

I nodded, approvingly. "You're my good girl."

Rebecca sat up to kiss me deeply. "Always. Um... I think I've earned an orgasm tomorrow night, don't you?"

I smiled indulgently. "Maybe." Actually, I planned on letting her cum her head off, as much as she wanted. But let her wonder.