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Chapter 89
by
Nevermore
A roleplay with Kara:
A visit to the doctor.
“Please doctor, I need help.” Kara entered my office / man-cave.
I should have known it wouldn’t be only a man-cave for long.
“Why don’t you sit down for a bit?” I gestured her to the chair in front of the desk.
“I can’t doctor...”
“You can’t sit, or you can’t be here for a bit?” I asked, almost smiling.
Fuck... these fantasies are sometimes so funny. The scripts are ridiculous, but their fantasy roleplays were a lot more visualized in their dreams, not so much on paper though.
“Are you smiling at my misery, doctor?”
Uh-oh... best to stay in character then.
“I wouldn’t dare. You are one of my favorite patients.”
“Ah... good.”
“So, what is preventing you to sit on a chair?”
“It’s my ass, doctor. It hurts. A lot.”
“Hmm... What happened, Kara?”
“I’m not sure, doctor...”
No reason then... I guess the script didn’t cover this in more detail... Ah well...
“Well, without knowing the reason, I am afraid I will have to take a look.”
“Oh...”
“Yes, oh... Why don’t you remove your pants and bend over on the desk?”
“Are you sure, doctor?”
“Well, if you don’t want me to take a look, I can always ask my assistant Emma... I’m sure she can find the time for it, while I proceed with another patient... who’s next? Ah... I see, Kate...”
“No... no... doctor, I will, I mean, I want you to look at it.”
“Are you sure, Kara? You seem a bit hesitant, perhaps we can reschedule.”
“It’s fine, doctor, it’s just that... no one ever looked at my ass, in that way.”
Probably a lot of people looked at your ass in other ways, as I did quite a few times, more than a few times...
“Okay, then. So, remove your pants, please. Bend over the desk.”
“Yes, doctor.”
She had to make a show of it, unbuttoning her pants, wriggling her ass out of it, while I was standing behind her with my arms crossed.
“Please remove them from your legs, Kate. If you close your legs like that, I will not be able to see a lot.”
“Oh... of course, doctor.”
Kara was nubile, could bend over and easily reach her own shoes, untie them and kicking them off.
“Good, Kara, now please stand at the desk.”
“You don’t want me to remove my panties?”
“I’ll check your thighs and lower spine first, Kara. Perhaps the solution is there, before we have to proceed.”
“Oh... okay, doctor.”
Slowly I caressed her lower legs, creeping up to her thighs. When my hand caressed her inner thigh, almost touching her panties, her breathing became shallower, she shivered involuntary.
Quite aroused, already?
I admit it had been a while since I gave some of my attentions to Kara and she had been waiting for this for the longest time.
“Hmm...”
“What is it, doctor?”
“I am not sure, but I have an inkling what is causing this pain of yours.”
“Already?” Disappointed.
“But I’ll have to remove your panties to make sure my diagnosis is correct.”
“Ah... Please go ahead, doctor.”
“I’m just not sure, if I should be the one going ahead, Kara, I am a male doctor and you are female patient. Perhaps you want me to call in my assistant?”
“No! I mean, no, doctor. With you I feel to be in most capable hands.”
“Okay, as you please, then.”
I took the hems of her panties at both sides and slowly slid them off. She stepped out of them and opened her legs wider.
I caressed her inner thighs again, up and almost reaching her slit, down before I reached it. She knew I would eventually touch her, but not when. Her anticipation for me to do so became higher.
“Please, doctor, it hurts a lot more now.”
“Are you sure, Kara?”
“Yes, doctor, I am sure.”
My hands touched her vagina, she shuddered when two fingers suddenly entered her, palm down and started rubbing her. She was wet. It had been a long time for her.
“Poor Kara, I see now what the problem is.”
“You... do...?”
“Yes, it seems your nether parts are under-stimulated as of late. It makes you hurt, every time you touch something.”
“Ah... ah...”
“Or every time something touches you here.”
“Ah... ah... in my ass too?”
“I am afraid so.” I said, while I continued fingering her with slightly bent fingers.
“Is... there... any... so... ah... lution... ah... to it?”
“There is, Kara, it is called an overstimulation of those parts of your body.”
“Ah... ah...”
“Luckily for you I have the right instruments for that.”
And I had. I was rock hard.
“Ah... go...od...ah...”
She was almost to the point of coming now. Sadly for her, I withdrew my fingers just in time.
“No...o...h...”
“Don’t worry, Kara, I will treat you, right here, right now.”
I undid my pants, shorts and upper clothing. She heard it, but couldn’t say anything. She saw me reaching for the bottle of lube, heard it clicking open before I lubricated my fingers.
“Kara, I want you to open your ass cheeks for me, so I can see more clearly.”
As if I was planning to look inside. Jesus... Where did I get these silly lines from?
I poured a decent amount of lubricant between her ass cheeks and as I held my hand below her anal flower, it flowed upon my hand. I started rubbing her ass groove from bottom to top. I proceeded with slowly encircling her anal ring with my fingertips.
“Oh... Oh...”
“Does it hurt, Kara? I can stop, if you don't want me to continue.”
“Yes, I mean no... eh... please continue, doctor.”
Slowly I entered her anus with my index finger, just the tip of it, turned my wrist clock wise and counter clock wise.
“Ooh...”
She had been preparing for this occasion, perhaps had the butt plug in her just before we started this play. I could easily enter her with one finger and soon an extra finger followed with just the tip. Turning and twisting I lubricated I anal ring more and more.
“This might hurt a bit, Kara.”
It didn’t really, I knew it to be a fairly pleasant feeling and she knew it too. Otherwise she wouldn’t have plugged herself for this long.
I entered her with two phalanges now, with two fingers and slowly bent them, turning my wrist again, feeling and lubricating more of her inner flesh.
“Ooh... Ooh...”
I straightened my fingers and plunged deeper now, my entire two fingers, bending them and touching her inner anal walls.
“Ooaah...”
I squatted down readying my other hand. Gently I entered her slit again, at the same pace as my fingers in her ass.
“Aah... Aah...”
Entering and withdrawing, she sped up her breathing considerably. But as before, I exited before she came too close to coming. She protested again.
“Please, doctor...”
“All in good time, Kara... I will now enter your ass with my instrument.”
“Ah.”
I lubed up my cock, lubricated her ass some more, directed the head at her anal ring and steadily pushed inside.
“Oooh...”
“Keep your cheeks open, Kara. It will hurt less.”
“It doesn’t hurt, Alex, I mean doctor.”
“Okay, I will now slowly enter you completely. Just stay still.”
“Ooh...”
“I’m in now, Kara. But I will not withdraw for now. Get used to the feeling. Say when you are.”
“Oh... Al... doctor, it feels so... full... so nice... so much... better...”
“I will pull you upwards at your shoulders and we will both step backwards to sit on the chair behind me.”
“Ooh... o... o... o... Ooh...”
It was a low chair, looks like it was made to fuck in. Not to sit at the desk. They knew what they were doing when they made this. Comfortable, simple, no armrests. Just a tilted seat with a hundred and ten degree angle and cushions nailed on it. I spread her cheeks while she sat on my lap with my dick still lodged in her ass.
“You decide the rhythm, Kara, lift yourself up with either your legs, or place your hands on my knees.”
“Oh... o... kay...”
She slowly raised and lowered again, impaling her ass on my hard cock. She was tight, but the lube made it easy. Her insides were sensitive, she moaned in pleasure. Her breathing was shallow, trying to get the right angle to feel it inside her, wriggling even a bit. It felt like heaven for me, my breathing became louder, at the same pace as she moved.
“Good, Kara, now sit back on my lap. Move your hands upon my knees, and move slowly forwards and backwards.”
“Oh... god... oh... oh...”
I let her tilt forwards and backwards while gently I let my hands fall upon her thighs. How much pleasure I felt, this slow stroking of my cock would not do it for me. I would stimulate her the same way she was stimulating me. My fingers slowly crept to her slit and to her clit. Two fingers of one hand entered her pussy, two fingers of the other hand were on her love button.
“Ohah...”
When she moved back, my fingers inside her rubbed her sensitive spot, the fingers on her clit slowly rubbed it with small circular movements.
She was panting now, but I didn’t move faster with my fingers.
“Please, Alex, faster...”
“As fast as you are... Kara...”
She sped up her tilting and felt my fingers following her pace.
“Much better, Kara...”
“Oh... god. Oh... god. Oh... god.”
I sped up the movements of my fingers, she was close, it was difficult for her to keep up the pace as her panting and gasping became irregular, unable to control herself.
“Alex... Alex... I’m... I’m...”
She came, squirting all over my thighs and knees. She clenched her ass in spasms. I groaned, trying to control my breath I whispered loud:
“Continue, Kara, please...”
“I can’t...”
I lifted her up while standing up, my cock fully lodged in her ass and dragged her weak legs with me, bent her over the desk. I withdrew and entered her, slowly but gradually faster. My arousal heightened, I felt myself on the brink, and finally I came too, cumming deep into her. I withdrew slowly, my cock kept on spurting.
“Alex... I can’t stand up...”
She was convulsing still, trembling legs, but with a last effort I dragged her backwards again, sitting on the chair, falling with my spine against the soft back rest. Both we rested there, trying to calm ourselves.
“Oh... Alex... that was... that was... amazing. It felt so... good.”
“Glad you liked it... I did too.”
“It didn’t... hurt... at all.”
“It’s not supposed... to hurt.”
A roleplay with Kate:
War!
Finding some happiness in catastrophic and terrifying times.
A story of a soldier in the greatest of wars, looking out for his people and searching for some happiness for others and himself.
Updated on Feb 25, 2022
by Nevermore
Created on Jan 3, 2022
by Nevermore
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- 155 Chapters
- 122 Chapters Deep
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