Author: Anonymous

It had come to that point in the relationship ­ she was needy, I was bored and it was time to end it. And one day, it happened. I was late meeting her at a restaurant. She showed her displeasure indirectly, never complaining but dropping hints about my lack of consideration. When we arrived back at her apartment building, she commented on how I didn't hold the door for her. Inside her apartment, I blew up and told her it was over, that I was leaving at that moment and not to call me. I was breaking it off. I grabbed my jacket and started walking out.

Caroline didn't take it well. She ran in front of me, barring my way to the door and told me we needed to talk about it. But I didn't want any more. In a matter of fact tone of voice, I told her we were finished and I was leaving. She seemed to think I wasn't serious. We had been together for three months and had fun and good sex. The sex was fairly conventional and she told me I knew how to make her come better than any other man. I hadn't really been honest about the fact that after the initial period of discovery, she became boring sexually. She always wanted the same thing: kissing, rubbing her clit until she became wet, oral sex and then the usual missionary or doggy style position. With doggy style, I was rubbed her clit and she came quickly which she believed was an achievement. "Orgasm guaranteed!" she would often say about it. Her sex talk was really getting on my nerves. I would stop listening when she started in with "Oh honey, oh honey, oh honey" or "Fuck me ‘till I come" which, incorporating the F word, made her feel very dirty and sexy. I'd had it with this little suburban- girl sexual diet.

On occasion, we would do other things at my prompting. I tied her to the bed a few times and fucked her while she was motionless. We did it standing up at the window. Someone did walk by and see her breasts moving up and down from the street and probably figured out what was going on. And I was insistent that she submit to me anally every once in a while.

The first time was interesting. Initially, she acted shocked. It just seemed dirty and non- sexual to her. She gave me the crap about "The anus is an exit, not an entrance". I was mildly threatening about leaving her and she requested that we work up to it. I started with a shower in which I soaped her up and then reached between her ass cheeks and cleaned her anus.

After the shower, I told her to turn around for an inspection. She complied and I spread her cheeks apart and was pleased with what I saw: no hair, nice tight asshole with a sexy fragrance.

The next step was to show her mine. I wanted to make sure that she would look at it closely and lay on my back, legs in the air and somewhat spread. I told her to look directly into my ass. She knelt down and put her face about equal with my crotch. I instructed her to lower her head about four inches.

Now she was looking directly at it. I squeezed my sphincter a few times. My erect dick flopped forward each time and she laughed. But I knew she was seeing my asshole and had a fair impression of its smell (it was clean, as usual).

After a few minutes, she realized that this was actually intimate and relaxed a bit. I then turned her around and started to lick her anus and she stiffened like a board. I asked her to relax and wait. Soon, with a little clit rubbing, she started moaning in the familiar way. Then I told her to lick me. She balked, then slowly started licking my scrotum and finally, when she was satisfied that there was no shit there, started in on my asshole. I knew what to do and moved my mouth to her clit. She immediately started orgasming. She came about five times in ten or so minutes.

Later she was embarrassed by what she was doing. But she knew it felt good. And finally, when her sphincter was relaxed, I started with my finger in her asshole.

Curious, I pulled it out and smelled it. Not bad, no overt shit smell. At this point, I was getting impatient and told her it was time for my dick. I lubed it up, spread some lube on her anus and pressed the head against the sphincter. The usual resistance. I rubbed her clit, whispered that she was hot and slowly pushed further. There comes that moment when the sphincter has to give way. It struggles for a moment and then opens. When this happened, Caroline said "Oh!" and it was clear that she felt a new, total kind of penetration.

Opening up her virgin anus, having her feel the girth of a dick in her most intimate opening really excited me. As I fucked her, her anal smell wafted towards me. She seemed to lose all decorum and was grunting almost like I was twisting her arm. Her asshole was warm and open and I came after about a minute. I wish it had lasted longer. Afterwards, I pulled my dick out of her anus and showed her that there was no shit on it, not even any brown and it didn't smell disgusting. In fact, it had a normal après-sex look.

But we did this sort of thing infrequently and it too had become somewhat predictable. So I was there at the threshold of her apartment, about to leave for good. When it became clear that I was serious, she lost her normal composure and asked me not to leave, to sit down and talk about it. "There's nothing left to say" I answered and motioned for the door. She then pushed her back hard against the door and said "Don't leave!" I started to forcibly push her out of the way. She then started crying hysterically and begged me not to go.

"Please! Don't go! Don't go! I love you. I can't be without you. What did I do wrong? Please. Whatever's wrong, I'll fix it. Don't go! Don't go!"

Her voice became and agonized, throaty whine, repeating "Don't go, don't go." She had slid down the door and was now hanging on to my ankles. It was truly pathetic. Any semblance of dignity was gone. At this moment, something occurred to me. It wasn't a conscious thought. It was more like the feeling of an emotional resolution. I didn't predict it, it just came. I paused for a minute or so with her whimpering on the floor, still holding onto my ankles. Then, in a low voice, I said:

"Caroline, I'll stay, but only for tonight. And you will have to do everything I say. Later, I will punish you -- tie you up, spank you very hard and sodomize you. I will penetrate your anus very deeply until I come. You must accept this without any discussion or complaints. Do you still want me to stay?"

"Yes, yes, anything. You really will stay?"

"Yes, if you do exactly what I tell you to do." She whimpered a little and said in a soft, high, dejected voice, "yes."

I realized this was a turning point for both of us. Before this, I had a mild leaning towards dominance that generally manifested itself through fantasies. I didn't know what a rush it could be. But, standing over Caroline, seeing that I was completely in control, I was intoxicated. I had a huge erection. And I couldn't wait to punish her and take what I wanted, selfishly. For Caroline, it was an acknowledgment that she had lost control of the relationship. She could have been repulsed by my demand and I would have left. The fact that she agreed was a step over the line of submission and subservience. And it redefined our relationship in a new, exciting way.

I spent some time with Caroline calming her down, soothing her with a glasses of water and wine and some kind words. I talked about music and movies for a while until she had stopped crying and was basically composed. All the time, I could see the tentative look in her face, wondering when I would start the punishment. After I went to the kitchen, I came back and sat on the edge of the bed.

"Caroline, I need to talk to you before we go any further. I meant what I said, if I stay, I will punish you. But we don't have to do this. I can just go. But if I go, it's final." She started to cry again, though she was still listening.

"Don't go" she said softly.

"OK, I told you what will happen if I stay. Do you remember what I said?" She nodded. "Then what did I say?"

"You would punish me."

"How?" I wouldn't stand for any prudishness or reluctance. She was going to submit completely. I gave her a choice and she wanted it this way.

"You're…going to tie me up and spank me and have sex with me."

"No! Not clear enough! Try again." No let up from now on, I thought.

"You're going to tie me up, spank me hard and…have sex with me in my ass." Still prudish.

"I said that I'm going to penetrate your anus very deeply until I come. Let me be more specific. I'm going to put you on the bed, face down, tie your arms to your sides, tie your legs so that they are spread. At this point, you can't move. I will then take your large hairbrush," it was a very light hairbrush with a large, flat back, "and spank you. I will spank for a few minutes and then let you rest. This will go on until I can see your cheeks getting very red and that it has the proper affect on you. Then I will give you a special secret spanking. After that, I will get some lotion and smear it on your anus. I will start loosening your anus with one finger and then two. As I go deeper into you with my fingers, I will inspect them for signs of shit or stain. If I see any, I will repeat the spanking exercise. When was the last time you shit?"

She was shocked at the question. I don't think she'd ever been asked before. She tried to answer. "Uh….I, uh…"

"When!" I yelled. No let up.

She swallowed, obviously mortified. "Last night," she said.

"Did you wipe?" I said, wanting to continue the privacy invasion.

"Yes" she said, her face turning red.

"Good. Then it will probably be OK. After I loosen your sphincter, I will position my dick at the opening to your anus…"

"Will you untie me for that?"

"No! But your ass cheeks will have relaxed and your anus will be slightly exposed. I will rub my dick on your anus to judge how tight the sphincter is. Then I'll begin to press until it starts to give way. I will repeat this until I get the head in. Then I'll do this again a few times until I can enter easily. Then I will stop for a couple of minutes." She was silent. "After I rest, I will position my dick in the same way and push it ALL the way in with a single stroke. Then I will stroke you until I come." Pause. Then the punishment will be over."

"Then what?" she asked.

"Then I'll clean myself off and spend the night. That's what I promised."

"Then what? What about the next day?" She was clearly anxious and wanted the punishment to have brought us back to couple status. This was too much like her old, cloying self and I exploded.

"Shut up! This is just about tonight! We'll take it a step at a time after that." I liked being unrestrained in my anger towards her. My dick which was getting hard in my description of the punishment, was now like a rock.

We were silent for a bit and then I asked. "Am I staying?" implying the punishment. She was silent again and then said, for the final time, in a very meek voice, "…yes…". I had only one other thing to clarify.

"Caroline, I'm going to cause you discomfort. And if it gets to the point that you feel you are being injured or that you really can't take it any more, you must say this word: ‘arête' which means ‘stop' in French." I had learned the "safeword" concept from reading about dominance/submissive activities. "If you say the word, I will stop immediately and untie you."

This seemed to make a difference. But then a shadow of worry crossed her face. "But if I say the word, what will you do then?"

"I'll leave," I said matter-of-factly.

"No! No!" She started to get really upset again. Apparently I wasn't going to be the kind boyfriend she thought I was implying.

"I won't take this past the point of endurance for you. But I don't have to stick around afterwards either. I told you what I wanted to do. You can take it or leave it." We sat in silence for what seemed like a long time. I could see that she was struggling with the whole situation. She wanted me as her boyfriend. I wasn't offering that. Instead, there was this forced sex which had a very uncertain meaning and outcome. She had to weigh her dread at seeing me go with the risk of doing what I had described and then possibly losing me anyway.

In the end, she chose for me to stay. And I started in on her.

"Stand in front of me." Fully clothed, she stood about three feet away from me. I was sitting on her couch. I looked into her eyes to discern how she was feeling. I detected anticipation. She hadn't ever done anything like this before. And she didn't really know what would happen next.

"I'm going to teach you the first steps in becoming sexually submissive. This will be necessary to get through the night. And it might be useful after that." I thought I'd tease her with this hint of a possible future for us. "The first thing to remember is that my sexual satisfaction is absolutely the most important thing in your life. You will do anything to please me. And my satisfaction must be immediate and amazing. Just doing what you think will get me off is not nearly enough. You must try as hard as you can to do better and more than last time so that I am more than satisfied."

"How do I know what to do? Can I just do the things we've done already? I'll do them really well."

"No! That's a lot of the reason why I wanted to leave. You need to break out of that mold and go all out."

She looked troubled. "I…don't really know what you mean. I think I'm pretty good at sex."

I looked sternly into her eyes. "You can get me off. But you are far from amazing. You'd better show a thousand percent improvement or it's over."

Now she was really confused. "Like what?" she said softly.

I was getting bored with her questions. I also wanted to get on with her punishment. I wondered whether her talk was subterfuge to somehow soften or avoid the upcoming ordeal.

"Caroline, I'm not going to spoon feed you. But I'll give you a quick example. Before you, I had a girlfriend who was very submissive but extremely passionate and inventive. One day I was at her place taking a bath. She came in wearing a only a sheet and stood there for a moment. When I told her to take it off, she dropped it, turned her back to me and bent over. She had inserted a peeled banana into her anus. It was amazing. It looked ridiculous and yet turned me on at the same time. She stood very close to me and slowly pushed it out of her anus. I could see her sphincter straining.

When it finally came out, I saw her little anus close up. I was really hot at this point but she wasn't finished. She picked up the banana and put her face close to mine. She brought the banana between us so that we could both smell it. She then crushed it into pulp and smeared it on her hands. She put the tip of my dick in her mouth and started sucking it. She then used one pulp-lubed hand to stroke my dick and the other to put a finger into my anus. I came in about a minute, really hard against the back of her throat. After I had come, she handed me another banana. I know that if I had put it in her ass, she would have eaten it if I had wanted her to." I paused and inspected Caroline's face for her reaction. She looked overwhelmed. "That's what I mean by amazing."

I didn't know how my story sat with her. I figured that if she had a negative reaction, she could just leave. I also wanted to give her an idea of how hard she had to try to please me.

Caroline had relaxed a bit. I renewed my command. "Stand in front of me. Stand up straight." She came to attention. "Now answer my questions. Has anyone ever fucked you in the ass besides me?" I thought I'd start easy.

"No."

"Do you like being fucked in the ass? Be honest."

She paused. "It's not bad once you get inside. But it can hurt."

"And after I come, do you shit out my sperm?" Now I crossed the line.

"What…do..you…" she was stammering.

"Just answer my question. Do you go in the bathroom, sit on the toilet and shit out the sperm I put in you?"

"…Yes, it has to come out."

"And does shit come out as well? Does the sperm have a laxative effect?"

She didn't want to answer. "Tell me!" I yelled. "Do it!" I startled her and she started to weep.

"Yes, usually."

"Usually what?" I wanted it all.

"Usually I…shit…after you come in me."

"And does the shit come out easier than usual? Does coming in your ass help you shit?"

"Ummm…yeah, I guess so." She didn't see where this was going. She thought she would just get spanked and fucked.

"Then I can be your personal physician for constipation." I smiled. She didn't. And I wasn't quite through making her uncomfortable.

"Tell me, Caroline, what do you think of the smell of your asshole? Do you ever scratch your ass and smell your fingers?" Once again, I embarrassed her. She started to sweat.

"No! I don't."

"Well, let's do it now. Unbutton your pants." She was motionless. "Caroline, either you unbutton your pants or the evening is over." It was a standoff for a few moments, then she reluctantly did as I asked. I reached down into her panties and rubbed my middle finger right on her anus. I could feel the moistness of the sweat that had formed there. I pulled it out and smelled it. It was pungent but nice. I put it under her nose. "Smell," I ordered her. She just stood there. "I want to hear you sniffing through your nose." I dipped my hand between her ass cheeks again to renew the smell. I stuck my finger under her nose. This time she inhaled loudly. "Well?" I asked. Silence. "Well?"

She paused and said "It's OK."

"OK? OK?" I yelled. Do you like it? Yes or no?" I was pressing my finger to her nostrils. The smell was strong enough so that we could both smell it. Her embarrassment increased as well as her trepidation. She seemed to be wondering how far this would go.

Finally she said, "Yes, I like it."

"She likes the smell of her asshole," I said to punctuate her statement. I had gotten through. Her embarrassment was complete. I looked into her eyes, smelled my finger again (it really smelled good) and then said, "Now pull down your pants just over your ass and turn around." She paused, wondering if the punishment would start now.

"Do it!" I yelled. She pushed her pants down. I could see the top of her pubic hair. Her ass was sticking out. She turned around. "Now spread your legs apart about twelve inches and bend over and put your palms on the ground." She was confused. I repeated the instructions slowly and demonstrated the move myself. She did it and immediately realized that this was a hard pose to hold. But it was great. Her ass was spread just enough to show her anus. A little bit of her cunt was visible. She was breathing hard due to the effort it took to hold the position. After two minutes, she stood up. "I didn't say you could move," I said sternly.

"But it's hard to stay that way," she said as if reasonability would make a difference to me.

"I don't care," I said plainly. "Now get back in that position." She complied and in a few seconds was breathing hard. I moved close and sniffed her cunt and anus. Nice smell. She was aware of my actions and was embarrassed but this was outweighed by her physical discomfort. I started to work my index finger into her anus, pulling it out every few seconds to smell it and to have Caroline smell it as well. When her legs seemed to get weaker, I put my mouth to her ear and said "I'm going to have to fuck your anus very, very deeply." That caused her legs to buckle and she fell down. I stood up and put my foot on her thigh to keep her down. "You are pathetic. You can't even hold a simple position. You're weak and clumsy." I was pressing my foot on her for emphasis. "Now get me the hairbrush on your bathroom sink." Once again, she was immobile, thinking (or hoping) that I wouldn't go through it. "Go!" I yelled. She slowly got up and went into the bathroom. It occurred to me that she might just lock herself in there. Fine, I thought, I'll just leave. But she walked out with the brush.

The brush was made of a very light wood, perhaps five or six inches wide and rather thin. I chose it because it was like a paddle, not too severe due to its lightness but it would definitely make the point. I took the brush and fondled it. "Take off your pants," I said. She did so slowly. "Now lie on the couch, stomach down and put my dick in your mouth." She arranged herself awkwardly, propping herself up with her elbows so that she was lying down but could suck me. She started in with the familiar licking. I swatted her ass so that a smack was audible. She stopped and looked up at me, surprised.

"Ow!" she cried.

"Shut up!" I said. "Suck it better!"

"How?" she said, sounding annoyed. I swatted her again. She yelled out with pain and jumped up on her knees.

"Just do it better!" I said, pushing her back down. She stretched out and started sucking fairly hard which felt better. I swatted her again. Again she jumped. "Suck it deeper" I said, not knowing if she could or not. She started sucking it harder and more slowly. She stroked my scrotum with her right hand. It felt great. I didn't want to come too soon and pulled my dick out of her mouth, feigning discontent with her work. I hit her ass with the brush and said one word at a time with each swat: "Suck it better, suck it better." Then she did something unexpected. She spit on her hand and started to rub the shaft up and down quickly with her thumb and forefinger. She put the tip in her mouth and sucked hard. Her other hand played tentatively with the opening to my anus. I could have come in a second. "That's better," I said and rubbed her ass a little then worked my middle finger into her anus. I took it out and smelled it. Then I told her to stop sucking and smell it as well. She did, breathing deeply. I could tell she was giving in and was just accepting my orders.

It was time for the beating and told her to lie on her stomach with her head hanging over the edge of the bed. I moved a chair next to the bed and put a pillow on it to hold her head. I bent her left leg up at the knee and tied it to her left wrist and repeated this on her right side. Her legs and arms were thus bent and tied in back of her. She was immobile. I moved to the edge of the bed where her head was. She was looking at me expectantly. I just stood there, taking in the scene. She couldn't move. She was ready to be spanked and anally penetrated. I could do anything I wanted. I almost said something but decided it would play better if I didn't. Instead, I got the brush and, with her looking hit my palm a few times with it. Then I went behind her.

I could see her cheeks tighten. She expected to be hit right away. I just stood there. Her cheeks relaxed. I traced the line of her ass crack with my finger. When I touched her, she squirmed then relaxed. I touched the brush to her leg. Again she squirmed. I breathed in hard and she tensed her cheeks again. I laughed. She whimpered a little and asked me what I was doing. I didn't say a word. I counted slowly to sixty silently.

During this, I noticed that she shifted her weight slightly and swallowed. I sensed that she expected me to warn her somehow before I started hitting her. It was at that moment that I began. I gave each cheek five swift strokes in very quick succession. I made sure to make a lot of noise. She yelled out. Her cheeks were clenched very hard awaiting the next blows. But I held off. She was trembling a little. I told her to relax her cheeks. She didn't. I gave her a quick swat on the left cheek and said "Do it!" and she complied. I spread her cheeks apart with my left hand. I noticed that her anus was clenched. I let go and stood back.

At this point, she was expecting another set of strokes. This time I waited two minutes and started suddenly. I hit her twenty times on each cheek, again quickly. She was crying now. I asked her softly if she needed to say the word to me. She was silent for a moment and said no. I told her that we were far from done. I could see her fright at this idea. I then started hitting her in random patterns, this time keeping it up for thirty seconds which must have seemed like an eternity to her. I paused three minutes and then gave her another thirty seconds, this time hitting her squarely across both cheeks. She stopped holding back and yelled continually as I gave it to her.

Along with her yelling, she was grunting in a very guttural way. I realized that I had broken her and now she was just dealing with her fate as it came, no longer trying to control or anticipate. When I stopped, her cheeks were very red. I touched them lightly with my lips and they were very hot. I could smell the sweat in her ass crack and crotch.

At this point, I stopped and looked between her legs. Sure enough, her cunt was wet. Little beads of syrupy moisture had formed on the lips. There was a long drool from the back of her slit to the bed. I knew at this point that she responded to submissiveness. After the initial shock of the beating, she gave in to the feeling of expanding her limits and putting her fate into another's hands. I was tempted to tease her clit to point out that she was turned on but thought I should wait. I sat there, looking at her drooling cunt and the redness of her ass cheeks for a few minutes. Then I gave her one last volley of strokes, this time twenty on each cheeks. She cried out again and started whimpering a sort of "Oh…oh…oh." It seemed that she was feeling sorry for herself and despaired that the beating would never end.

It was at that point that I walked over to the edge of the bed, knelt down and looked her in the eyes. I knew she had forgotten about the "special secret spanking" I spoke of earlier. I said "Caroline, now it's time for the special spanking I mentioned earlier." I waited for her to ask the inevitable question. She was frightened since she assumed that a spanking was a spanking as I had just administered to her. Her mind raced. Was I going to use a different paddle? A whip? She looked at me through tear-soaked eyes and said meekly, "What's that? Are you going to hit me harder?"

"No," I said, "actually, this spanking isn't nearly as hard as the last." I could see the confusion on her face. But her anxiety grew. Even if the spanking were softer, it must be worse in some way or else I wouldn't be making such an issue of it. "It's a very intimate spanking." I looked her in the eyes again. "And one you won't forget soon." I walked slowly back to the other end of the bed. She squirmed, straining against her bonds. The fact that she didn't know what was next was making me very hard. But I continued.

I sat on the edge of the bed and rubbed her reddened cheeks very softly. They were still very hot. I slowly spread her left cheek open. As soon as I did this, she clenched her anus. I kept the cheek spread. After a few seconds, she relaxed her sphincter and the little rosebud spread a little. Drops of sweat were visible in the crack. As I repositioned myself slightly while keeping her ass spread, she began to formulate what might happen. And then she started to whimper again.

She was right. I positioned the brush about five inches from her left inner ass cheek and gave her three quick swats. Her anus clenched hard and she whined "Ow!" like a wounded puppy followed by a bout of crying. I repeated this on her right inner ass cheek with similar results. I then hit her directly on the anus a few times. All of these strokes were gentle. They did however, make a little slapping sound. I knew that each one gave a slight sting. That coupled with the novelty and privacy invasion of this punishment clearly touched a hidden place in her. She stopped crying and just started breathing hard. I gave her a few more strokes on each side and on the anus. I noticed that after her anus clenched and relaxed, it was more open that before. That was my secret agenda and the desired effect. She was ready for the next event of our evening together.

I gave her a few minutes to rest then lubed her anus with lotion. She took it all motionlessly, submissively. I quickly took off my pants. My dick was ragingly hard. I slipped a finger in and moved it in and out for a while. Then I used two fingers. She gasped. Clearly she was anticipating the next step. I stuck my middle finger in all the way to the hilt and pulled it out to examine it for signs of shit. None. I showed her this. Then I positioned my dick at the opening to her anus. I pushed it in so that just the tip penetrated her. It went in easily. Then I repeated this.

When her sphincter was adequately loose, I slipped it in fully. She gasped slightly though I'd done this before. I started to stroke her, softly but firmly. The pliancy of her anus was amazing. I decided that I should sink it to the hilt. I did this and she grunted slightly. I kept pushing it as deeply as it would go and she muttered an "Uh" each time. Without meaning to, I squirted all my sperm into her. I pulled out my dick and looked at her ass. No sign of come on her anus. I then rubbed her clit very lightly. She responded heavily. I kept it up, watching her anus open and close rhythmically. It took her about a minute to come. As she did, a little bit of sperm seeped out of her anus with each contraction.

When it was all over, I untied her. She was sore and curled up in a ball. I said softly "You did pretty well," and slipped under the covers.

I would stay the night and more.