It took a bit to be the Anal Queen (M/F, BDSM) | 2016

“Another UM kinkster?” That was effectively the whole message. He was surprised that I had the gall to try to set up a public munch at our school. I don’t know if the intent was to strike up a conversation or not, but eventually he lured me to a public place to meet up. We decided to meet at the mall, which was easy and fun. He and I wandered around and made small talk, getting to know one another but still putting out feelers in case the other was a serial killer. After a little while, he offered to drive me to one of his favorite spots. I got in his car for the first time. A perfect gentleman, he drove sanely and opened and closed my door. When we arrived at the nearby pier, it had gotten a little late and a little chilly. He came up behind me and grabbed me by the stomach, moving me. I knew that he was testing his ability to dominate me and I certainly didn’t mind.

Once it gotten too cold to stay outside, he pulled me back into the car. We climbed into the backseat and he ordered me to sit on his lap, which I did readily. At this point, he took off my bra and shirt and started to admire my full breasts. Taking them in his hands, he asked if I would be interested in playing a little bit. When I nodded meekly, he flipped me onto my stomach and told me to gauge the level of pain in each strike on a scale of 1 to 10. The first spank was nothing more than a brush of the hand. The second was significantly harder, but it was nowhere near my usual tolerance. We settled on a 2 for his hardest spank. He chuckled and we agreed that we should commence with the training relationship he and I had discussed.

Only a couple days later, he invited me out again. This time, he opened the door for me, but as soon as I sat down, he ordered me to strip out of my panties and bra, keeping on my dress for propriety. I was to climb into the back and not say a word. When I finally got settled, he joined me in the backseat.

“I talked to your Master. He says that you’re not willing to even try anal with him. This is a problem. No respectable slave pushes her Master off when he wants a piece of her. Your Master has said that I am his proxy and since you have no right to tell him no, you have no right to tell me no. That said, I want to be safe. So you have access to a safeword. If you use it, we will stop everything and discuss what went wrong. There will be severe punishment for using it except in an emergency. Are we clear, jade?”

“Y-Ye-yes, Sir… Umm… What else has Master asked that I learn?”

He chuckled. “That’s really none of your concern. Now I suggest you shut your mouth and get on your back.”

I laid down and spread my legs over his lap. I was terrified. The last time I tried anal, I bled and it felt awful. But Sir was going to do it with me? It wouldn’t fit! There’s no way! Lo and behold, Sir unsheathed his cock from his jeans and brought it close to my face. Because of the angle, I was gagging before I had his whole head inside my mouth. He muttered to himself, moved slightly, and shoved his wide girth in. Once I had wet him slightly, he pushed me back down. He warned me that he did not want to see me so much as move while he prepared to enter my ass. To prepare me, he spit on his finger and started to massage my asshole. I instinctively clenched, making the task almost impossible.

“You need to relax. This won’t hurt if you’re good. I can’t promise what will happen if you’re bad. So relax. Tell me about your day.” He used a soothing tone to coax some calm from me as the other hand moved to my clit.

“Well… So I had this task that Master assigned me, but I couldn’t finish it, so I tried to tell him. He was angry that I didn’t do it, but I tried! So I hung up on him. That was basically the highlight of the day.” I laughed lightly, thinking that I was so clever for “winning” the argument. But halfway through my giggle, he stopped gently rubbing my clit. “What? It’s not like he was being reasonable!”

“You disobeyed a direct order, got into a fight, and then hung up on your Master? Is that so?” I nodded. “Well. Text him and apologize. Tell him that you will be punished shortly. Now!” he barked. With shaking hands, I told Master I was sorry for my behavior and that I would have a fitting punishment. “I do not want to hear one instant of sniveling. I am going to take your ass. There’s nothing you can do about it. You will not treat your betters like that again. Is that clear?” I whimpered and whispered “yes Sir” before lowering my eyes.

In a blink of an eye, he had pulled me into a missionary position and spat on his cock. He angled the head at my asshole and started to push it in. It was excruciating. I could feel the skin tearing. I held back my noises and instead let myself cry. He spat on his hand and used it to lube himself up slightly. Each time he pushed, it felt like he was driving a stake into my bowels. I couldn’t handle it any more. “Red! Please. Sir. Please. No more!” He glared at me and stopped moving. I knew in that instant that he had talked to Master about punishments. After all, I was not allowed to use a safeword during a punishment, no matter what. He had obviously decided that not having any communication during punishment was dangerous, but he was displeased.

“Explain why you stopped me. Now, slut.”

“Well, Sir, it’s too painful. I can’t do it. I don’t know how far in you are, but I can’t do it.”

“Here’s the deal: you’re being punished. I am not damaging you. It should hurt. Now, if you take it like a good girl, I’ll buy you ice cream. If you don’t, I’ll make sure it’s worse for you. And for the record, the punishment ends once I get the head in.” Wait, what?! He wasn’t even done with that?!? I gritted my teeth, nodded, and let him push himself inside me again.

After a few more grunting thrusts, he announced that I had been good enough to be done, but in order to earn the ice cream, he needed to get off. And that would take some sex. He leaned down and kissed me, claiming my mouth. If I tried to kiss him back, he would bite my lip. I just enjoyed the sensation. Little did I know, he was moving inside me. It didn’t hurt when I was distracted. He let me float a little while longer.

Eventually, he pulled away from the kiss and started to push inside me. I had never had anything in my ass, not like this, at least. A few minutes later, I felt his orgasm. With a smile, he pulled out. “That’s a good girl. Put on your bra. Leave your panties off. We’re getting ice cream.”

And so we did.