In order to convince Diana, who was very strict with slaves, that no special treatment would be tolerated, I was filled with all the motivation I could muster, but...
"Master Neil seems to be all ready to go..."
Diana, in her underwear, says these words to me while looking at my son who is now only partially motivated.
It's hilarious, I'm supposed to be trying to convince Diana, but how did this happen?
Well, about 30 minutes ago, I tried to catch Diana giving instructions to the ladies and convince her that there was some complicated reason for the man to leave the meat, but Diana, who is very strict with herself and others, would not be easily convinced by that.
"If it is a physical problem, I will consider it, but if it is a mental problem, that guy must overcome it. And Master Neil, in case you have forgotten, that man is a guilty man who has been reduced to a criminal slave. A criminal should be punished. Rather, it is impossible for him to get off with such a low level of punishment, isn't it?"
Well, the conversation went on and on, and Diana made a proposal to me, as if she thought we could not settle the matter.
"It's hopeless, huh? Then, Master Neil, please wait in the bedroom. I still have some work to do, so I'll come as soon as I'm done."
"Hmm, I guess I'm interrupting your work. Okay, I'll wait in the bedroom and we'll talk about it there."
In retrospect, I should have wondered why the bedroom was chosen instead of the office, but my mind was so occupied with how to persuade Diana at that time that I could not think that far.
I was lured into the bedroom, and Diana came to me after giving me the instructions.
As I was ready to continue the story, Diana suddenly took off her clothes.
"Huh!? Why are you taking off your clothes!?"
"Oh, did Master Neil prefer to take off my clothes by himself?"
"No, I'm not talking about your preference! I thought we were going to have a talk!"
"It's obvious that neither of us will back down if we continue the discussion. So we'll decide by another way."
"Wh-what other way?"
I ask her in return, though I already know the answer when she takes off her clothes.
"This is a review of the last time, Master Neil, but this time I'm going to move too. The one who runs out of energy first loses."
"What's the point of this game!?"
I argued with her that even if we can't solve the problem through discussion, it's not a good idea, but sadly, despite my rationality, my instincts were reacting to Diana's underwear.
"But Master Neil seems to be ready for this."
And so we come to the present... But no, I'm not ready, I'm just reacting on my own.
"Wait, wait a minute!"
"No wait, the game has already started."
Saying this, Diana deftly pulls off my pants, exposing my son to the air in the face of my resistance.
"Last time, I couldn't see it well in the dark―but, hmm, I see that this is Master Neil's manhood, huh? It's big... isn't it?"
I personally think I have a big phallus because it is at least above the average size of Japanese men, but I don't know what the average size of men in this world is, so I don't really know.
Diana looked at my son with a sly smile, then she held my balls with her left hand as if supporting them and started to move them up and down with her right hand on my pole.
"How are you feeling?"
"Oh, it feels good."
It feels really good, but I wonder if it's my imagination that she seems to be strangely familiar with this technique.
"I wonder why you're not moving with any hesitation..."
"Please don't think weird things during the act... I just got a little instruction from my mother."
Perhaps offended by the question, Diana starts to handle my thing a little harder, a little peevishly.
Although frustrated, she is not rough at all, and her hands are so firmly aimed at making her partner feel good that a clear liquid is already spilling out of my bell mouth.
"Hehe, you're already getting wet. How about this?"
Diana smiles demonicly and kneads the glans with the palm of her hand so that the liquid spilling from the bell mouth is applied all over the glans.
My hips reflexively lifted up at the stimulation, which was stronger than the one from handling the rod.
At my reaction, Diana's smile deepened, and her hand movement on the glans became more intense.
"Diana, if you do it that hard, I'll...!"
"Please, take it out whenever you want."
"Wh-what do you mean, anywhere I want?"
"In my hand, in my mouth, in my breast, and of course inside me."
Diana's words reminded me of the last time I had done it her, and the feeling of Diana's inside, which gave me the final push, and I reached my limit and ended up in Diana's hand.
"Oh, you came out already, huh? That was surprisingly quick."
"Hey, don't say it so quick."
I, who had cooled down after having cum once, make a comment on Diana's word, and calmly analyze the current situation.
I feel like I've accepted the game by force, but I realize that the conditions for winning the game are not quite clear.
"Hey Diana, when you say that the player who runs out of energy first loses, does that mean until either of us is exhausted and can't move anymore? Or is it better to make the opponent say, "I can't do it anymore!"?"
"Yes, that's generally correct. It means until it is too hard to continue the action or until the other party gives up."
"I see... yes?"
Wait a minute.
"When you say it's too hard to continue, for example, if I'm squeezed so hard I can't get a boner anymore?"
"In that case, of course, Master Neil loses."
"That's not an equal match, is it!?"
Unlike Diana, who has a pure contest of physical strength, I lose as soon as I shoot all my bullets, no matter how much strength I have left.
"It is a basic rule of the game that players should try to get the upper hand. Master Neil, you lose when you are forced to accept the game."
"Ugh! It's not decided yet!"
Thinking that I can still win the game back, I put my hand inside Diana's underwear and squeeze her breast.
"Hm, you touched my breasts out of the blue, have you forgotten what happened last time?"
"This is a game, I can't win if I'm worried about it."
I roll the hard pointed nipples with the palm of my hand and slide my other hand into her lower abdomen, and I feel a sticky sensation on my fingertips.
"What, you're already wet even though I didn't touch you..."
Hmm? I'm sure she wasn't this upset when I made a similar comment before, and I don't know what happened, but I take this opportunity to push the pace to my side, and I start to torture Diana's secret part.
I wet my middle finger with the love juice overflowing from Diana's secret, and when I slide my finger into her vagina, hot undulating folds entwine with my middle finger.
Diana's vagina is still a little tight even with one finger, so I move my finger and suddenly feel a strange sensation in her vagina.
One side of the vagina feels hard, the folds are the same, but that side doesn't catch my finger at all, or doesn't sink into the vagina at all.
Could this be?
"Diana, don't tell me that you're keeping that thing in?"
"...I would never pull it out without Master Neil's permission. This is a punishment."
"Really, Diana, you're so serious..."
With that, I pull my finger out of Diana's vagina and run it along the back of her underwear, toward her anus, and I feel a knack on my fingertip that is clearly different from the feeling on Diana's soft skin.
"Wow, it's really in there."
"What's that reaction, Master Neil told me to put it in my ass as a punishment, didn't he?"
The punishment I had given to Diana before was a shameful play in which she had to spend some time with a foreign object in her anus.
In this world, this kind of abnormal play is really treated as abnormal, and most of the time, if someone asks for this kind of play, they are seriously rejected.
That is why I suggested that it might work as a punishment, and Diana accepted it as I had planned.
However, there was one thing that I did not expect, and that was the problem of defecation, which is a physiological condition that every human being has.
Naturally, she could not defecate with a foreign object in her anus, so I decided to allow her to remove it only at that time, but she started to ask my permission every time she defecated, because she thought that this was a punishment and that she should ask my permission when she removed it.
In other words, I unintentionally became in charge of Diana's excrement, and I knew when she went to the toilet and how many times a day she did so.
This seemed to be the most difficult thing for Diana, and her face was distorted with shame every time she asked me for permission.
When she once asked me for permission in front of her father, Ronald-san, she must have been so embarrassed that her face lit up.
I pushed Diana down on the bed by surprise and lifted her legs up, so to speak, into a piledriver position, in order to get a better view of her anus.
Thanks to the daylight, I could clearly see Diana's secret parts and her anus.
Her neatly trimmed pubic hairs, her labia and vulva, and her anus, which was furrowed with a foreign object, were too much for a man who had been a virgin only a few weeks before, and my son was again aroused.
I'd like to insert it here, but I don't think I can do so yet, because I haven't fully relaxed her vagina yet... but wait, what if I can't?
I look down a little from Diana's secret opening to her anus, which is now wrinkled from the foreign object in her mouth, and compare the size of the foreign object in her anus with the size of my own son.
"Looks good to me... Well then."
"Master Neil? What are you doing―!?"
I grab Diana's ass slowly and pull her ass outward with both hands as hard as I can to make her open her anus.
Then the foreign object in her anus is slowly pushed out and starts to come out.
"Look, I'm giving you permission to let it out."
"No, I can't, Master Neil! No way!"
"Don't be shy..."
I grabbed the end of the foreign object and pulled it out of Diana's anus at once.
The moment I pulled out the foreign object, Diana's back arched up, her whole body convulsed, and her vaginal opening was overflowing with her love juice.
Is this reaction really...?
"Diana, did you come in the ass by any chance?"
"I see, you've been taking this thing in and out for two weeks, so it's no wonder..."
"No, no way! It's not possible that I can feel it in my ass."
"Well, do you want to give it a try?"
I say, and place the tip of my glans into Diana's asshole, which is now empty after the foreign object has been removed.
"Try...? Master Neil, what the hell are you―!?"
As soon as Diana realizes my intention, I thrust my hips forward.
As soon as my rigid dick sinks into her anus, Diana lets out a moan like a beast from her mouth.
And I was also recoiling from the sensation of anal intercourse, which was different from that of vaginal intercourse.
Unlike the tightness of the vagina, the anal sensation gently enveloped my pole as if it were sucking it, while the chrysanthemum gate tightened around the base of my pole as if it refused the entry of foreign substances.
If I move my hips back and forth in this state, it is as if the rod is being handled tightly with my fingertips making a circle, but at the same time, the tip of the rod is gently coated with something hot and sticky, and the feeling of being properly engulfed is a perfect description to stimulate all of my parts.
They say that some people are addicted to anal sex, and I see, I might get addicted to it.
"Aah, aah, ahhhh!?"
With each thrust of my hips, Diana's mouth emits a moan-like gasp, and when I pull my hips back, her back arches in pleasure, making her scream lewdly.
"This! I can't do this!"
"I see! Diana is feeling it in her ass right now!"
"No, no way! I'm not a... I'm not that kind of woman."
Diana denied it desperately, but no matter how hard she tried to deny it, every time I moved my hips, the love juice from her vaginal opening overflowed into her anus and my rigidity, and Diana's moaning started to have a lusty color.
Diana's buttocks were bouncing with every slam of my hips, her breasts were shaking, her secret was dripping love juice, and her anus was sucking my son and I was getting close to my limit, partly because of the lewd sight in her eyes.
"Diana, I'm going to do it a little harder!"
"Huh!? No, I can't go any further...! I can't do it!"
Diana said such words to me as she felt the pleasure of getting her ass gouged out, but I ignored her words as my limit was approaching and started to give the last spurt.
"Now, I'm going to cum!"
"No! Don'tttt! I don't want it! I don't want any more―"
Feeling my limit, I drop my hips deeply and release my semen into Diana's intestines.
I was so excited that I could not believe that I had already cum once, and the amount of semen passed through my testicles to my urethra and soiled her intestines.
"Oh, ah, ah...! Hahh, hahhhh...!"
Diana's whole body jerks and twitches as semen pours into her intestines, and then she lies down on the bed exhausted.
Diana's whole body was covered with beads of sweat, and fluid was spilling from the corners of her eyes and mouth, and she was staring at the canopy in a daze.
Diana's obviously "after the fact" appearance and the lewd smell that rose from her whole body made my son get hard again, even though I had already let it out once.
"Diana, I'm sorry to leave you in a daze, but I'm still ready to go."
"So you're going to stay with me until you run out of energy."
"Wait, wait, I can't go any further..."
Diana, who had regained her senses, was about to say something, but I resumed the action regardless.
Because this is a game, and it can't be over until there is a winner.
So I humiliated Diana with my anal sex, and I was victorious and sexually satisfied.
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