Paying for Mistaes

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Author's note:

This story is meant to be a fantasy. As such, many points of reality are put to the side, such as safety and pregnancy, as well as others.

Additionally, this story will cover a wide range of sexual activities. I will try to cover them in the into, but please be aware. All characters are at least 18 years of age.

This story was written in two versions. Please check out the other version, A Guy's Mistake, and let me know which one you liked better, and your thoughts about the differences between them.

Following comments that I have gotten previously; Everything here is meant for the purpose of telling a story and titillating the reader and is not meant as a portrait of reality. I love hearing from readers, but if you comment that it wouldn't happen that way in real life, well, that's why it's a fantasy.

Thanks to my amazing editor ResqJack!

Topics: MF, reluctance, spanking, anal, oral, incest

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I got a good job right out of college. And by that I don't mean just any good job, I mean a really good job. One that normally requires five years plus of experience and pays triple what anyone else in my graduating class was making. I owed it to my uncle, who was the one who got me the job. That is not to say that I wasn't qualified, as except for the experience, I was, and I proved it by doing the job and doing it well. My uncle, besides for being my boss, was also a mentor, guiding me through the intricacies of the job itself and work politics, of which he was a master. He was my mother's oldest brother, but even in his mid-fifties, he was still in shape and looked good.

Six months into the new job I made a small mistake. I found it out a week later, but I didn't think that it was a big deal, so I ignored it. Everything seemed fine, so I forgot about it. About a month later, it turned out that my small mistake had snowballed into a much bigger problem. I was scared about what was going to happen, not really even in terms of my job, but more of losing the respect that my uncle had for me.

The meeting that I had been dreading finally came. He called me into his office. I entered with trepidation and saw the anger on his face. I knew that, while he was usually calm and collected, he did sometimes have a temper. I had seen it a few times directed at others, but never at myself.

"Close the door and lock it," he said in a frosty voice.

I did as instructed, knowing that I was really in for it, and glad that the soundproofing in the room meant that nobody would hear him ream me a new one. Ashamed and not able to meet his eyes, I made my way to the chairs in front of his desk.

"Who said you can sit?" He asked, once again in the cold, angry tone.

I quickly stood back up.

He just stared at me for a few minutes in silence as I squirmed under his gaze.

"You fucked up," he said angrily, finally ending the silence.

I started to speak up, but he cut me off instantly.

"I didn't tell you to speak." He snapped. "It isn't the mistake you made that I'm pissed at. It was the fact that you didn't tell me about it so that we could fix it. And because of the fact that not only do you work for me, but I also stuck my neck out to get you the job in the first place, this looks really bad for me!"

By the time he was done he was yelling louder than I had ever heard before. He took a few deep breaths before continuing.

"Now, do you have anything that you want to say for yourself?" He asked, his voice back under control, but still obviously seething.

"I'm so sorry. I only noticed it a few weeks ago, and I didn't think that it was such a big deal or that it would cause so much trouble. And I especially didn't want it to reflect badly on you," I said, the words tumbling out of my mouth, trying to hold back the tears.

"I get that," My uncle responded when I finished. "And I appreciate that you didn't want it to reflect badly on me, but you made it worse by not telling me. Sometimes you just need to drop your pants, bend over, and take your punishment like a man."

Even amid everything, I thought that it was ironic that he should say that, because of everything he could have called me, I definitely wasn't a man. My long blonde hair, large tits, and wide hips were testament to that. I didn't know what to say at this point in response, so I just looked at the floor.

"Well?" He asked after a minute.

"What?" I asked, not sure what he wanted from me.

"Are you going to take your punishment like a man?"

I still wasn't sure what he meant, but I knew what my answer was.

"Yes," I said, looking up at him.

"Well?" He asked again after a minute.

I looked at him not understanding. He pointed at the side of his desk which he always kept clear. I made my way around to the side and looked at him again. He once more gestured to the desk and me. I suddenly understood that he hadn't been speaking metaphorically. With shaking hands, I undid my pants and pushed them down to my ankles. As I slowly bent forward over my uncle's desk, I was oddly pleased with the fact that I had chosen to wear nice panties. Once I was in position, he stood up and walked around until he was standing behind me. I could feel his eyes on my mostly bare ass and was doubly grateful that I had chosen to wear a pair of cheeky panties with just a bit of lace instead of either granny panties or a thong.

Before I could think anything else, I felt a sharp crack as he brought his hand down on my exposed ass. My head shot up at the pain and shock radiating through my body. I didn't have time to react more than that before another and then another slap landed hard on my backside. Unable to hold it back, I cried out as my uncle, my boss, spanked my ass over and over. I quickly lost count of how many times he spanked me, the pain and humiliation being all that my body could process.

The spanking eventually stopped, and my crying settled down, first to sobs and then to sniffles as the final tears rolled down my cheeks. I went to stand up, but my uncle's hand pressed on my back, forcing my large chest back against his desk. I felt his other hand take hold of my panties and pull them down. I was mortified not only by the fact that I was completely exposed to him now, but also that the smell of my arousal suddenly filled the air. I felt betrayed by my body and the wetness that I felt dripping out of me. My uncle chuckled softly behind me, but I didn't even really notice, because, at the same time, I felt something cold and wet press between my ass cheeks and up against my asshole.

My eyes went wide, and a gasping whine escaped my mouth as my uncle forced his cock inside of me, stretching my virgin asshole for the first time. I wanted to scream and fight, but aside from knowing that nobody would hear me and that my chances to stop him were small, I had also said that I would take my punishment. I had let him down enough as is, so I tried to relax and let it happen. Feeling my body relax, my boss removed his hand from my back and grabbed my hips with both hands, and slowly started working his way deeper into my bowels. I had never felt so full in my life as I did by the time his thighs pressed against my sore ass. I had tried to be silent as he buried his dick in my ass, but soft moans kept escaping me as he stretched me further and further. I was embarrassed by how wet my cunt was when his balls pressed against it. I didn't want to be turned on by this, and even if I was, I didn't want him to know it, but my body betrayed me.

My uncle held inside my ass for a minute, enjoying my tightness and letting my body adjust to having him inside me. But all too soon, he pulled out and then thrust back inside. I couldn't help but moan again as he fucked my ass. He started thrusting slowly, but once my butt was stretched enough that his cock slid in and out easily, he picked up speed. Before long, my boss was fucking my ass with abandon. Each time his thighs hit mine, the ache from the spanking flared up, mingling with the sensations coming from my ravished ass. To my horror, I felt an orgasm building deep inside of me and heard the involuntary moans of mixed pleasure and pain coming from my throat. My uncle, my boss, thrust deep into my ass one final time and held there. I could feel his cock twitching deep inside me for a moment before I felt him start filling me with his hot cum.

Feeling him coat my bowels with his cum was too much for my poor, abused body. I let out a guttural moan as the orgasm that had been building deep inside of me burst out. Both my pussy and my ass clamped down and my body shook as I rode out the most intense orgasm of my life. I could feel my juices dripping down my leg, but other than the physical sensations, my brain had turned off. I vaguely remember protesting incoherently as my boss pulled his cock out of my ass, but it was a few minutes before I could stand up. Finally standing up I saw that my uncle was once more sitting in his chair, completely composed. He handed me a package of wipes and pointed to a wall closet he had opened that had a small sink and mirror inside of it.

Blushing, I quickly wiped down my legs from the juices that had run down there, and my ass from the remains of the lube that he had used. I wasn't yet leaking his cum from my sore ass, but I was pretty sure that it was going to happen soon. I pulled up my panties and my pants and washed my face in the sink. Looking in the mirror I could see that it was obvious that I had been crying, and one would assume that the flush across my face was from that, if they didn't know better. Finally, as composed as I could be, I turned back to my boss. He pointed at the seat that I had gone to take when I first walked in. I walked slowly over, my sore, violated, ass making me waddle a bit. I sat down gingerly, heat from my spanked ass spreading through my body as I put my weight on it.

"I treat all my employees equally," my uncle said once I was settled. "And I believe that once punishment has been administered, the transgression is, not forgotten, but forgiven. That being said, in addition to today's punishment, I would like you to set a series of ten, fifteen-minute meetings, first thing Tuesday mornings, to evaluate the status of this little blunder and to make sure that you don't make this kind of mistake again."

I nodded and he waved me out. I slowly made my way to the door and composed myself best I could before unlocking and opening the door. I forced myself to walk quickly and confidently back to my desk, and only slightly regretted sitting down normally as the pain in my ass flared again. I tried to focus on work, but my mind kept going back to the heat from my spanking, the soreness from my fucking, and the memories of everything that had transpired. I was so caught up in myself that I didn't notice my uncle's secretary walk up to my desk.

"My first big mistake was in my first week," she said to me quietly. "Most people wind up there within the first couple of months. This cream will help cool the heat," she said and placed a small bottle of cream on my desk. "Just remember that he has your best interest at heart, and everyone in this office would do anything for him because they know that he cares about them."

She walked away, and I took the cream to the bathroom. As promised, it did calm the heat from the spanking and make it easier to sit, but the sight of the red handprints that covered my ass made my cunt wet again, even as I rubbed the cream into them. I somehow made it through the rest of the day and even managed to get some work done.

When I got home, my mother asked how my day was. I stopped and looked at her for a moment. How could I tell her that her older brother had spanked me, and then fucked my ass? After a moment I said "Good," and was surprised to find that I actually meant it. I hurried to my room under the pretense of needing a shower, but really just needing to be alone to try to process. Standing under the hot water, the heat soothing my aching parts, I realized that what his secretary had said was true. Regardless of anything else, he cared. That, combined with how he had treated me up until that point was enough for him to earn my trust. Especially considering the orgasm they came with it. I found myself masturbating in the shower as I went through everything again. I was scared about what Tuesday would bring, but I would face it, as my uncle said, like a man.

The next morning, I wanted to talk to my uncle about what had happened. I didn't even know what I wanted to say, but I felt like I should say something. I glanced at his calendar to see if he was available and saw that he was in the middle of a fifteen-minute meeting which was marked as private and was in the same slot as our meetings on Tuesday. Curious, I made myself a coffee and hung out where I had an unobtrusive view of my boss's door. A minute later one of the guys from the sales team unlocked and opened the door. He hurriedly walked away from the office in the direction of the bathrooms, looking embarrassed and glancing around to see if anyone had seen him. I slipped back to my desk without being noticed. Thinking back, I remembered that the guy I had just seen come out of the office had lost a major client not too long ago, apparently because he said something stupid. It seemed like my uncle really did treat all his employees equally.

When Tuesday morning finally came around, I was both nervous and excited. I put on a pair of black lace panties, wanting to look nice when taking my punishment. I got to the office early and presented myself at my boss's door exactly on time. My uncle called me in, and I found him sitting on his couch, sipping a cup of coffee. I closed and locked the door before turning back to him.

"Have you done anything that I need to know about that you haven't told me about?" he asked.

"Not that I know of."

"And if you do?"

"I will tell you right away so that we can deal with it appropriately and will accept punishment accordingly."

"I'm glad to hear it. Come here."

I approached him and he stood up.

"On your knees," my boss instructed.

I complied, and he continued.

"As I said the other day, you caused me not a small amount of trouble. Therefore, once a week, you will come in here and not only be reminded not to make the same mistake again but also to repay some of the debt owed."

He opened his pants and I found myself face to face with the cock that had violated my ass the week before. Here I was in much more familiar territory than I had been when my uncle took my last virginity. I was surprised by the size of it, especially since if it hadn't already happened I never would have believed that it would fit in my ass. I must have been staring for longer than I realized, as my boss put his hand on the back of my head and pulled my face towards his cock. Coming back to the present I opened my mouth and grasped the base of his erection with one hand. I darted out my tongue to lick the tip, tasting him for the first time. I was going to play some more, but the pressure on the back of my head told me what he wanted. I opened my mouth wider and took the head of his cock into my mouth. Wrapping my lips around his shaft, I slid my mouth down his shaft sweeping my tongue around as I did. As I began bouncing my head up and down on his shaft, my uncle let his hand drop from the back of my head to my shoulder. It didn't take long before I was rewarded with a mouth full of cum that I quickly swallowed. Letting his spent dick out of my mouth, I sat back on my heels and looked up at him as he tucked himself back away.

"Anything else?" I asked.

"That's it for this meeting."

"Ok," I said, standing up. "Next week, if you are interested, I can take my time. I'm actually pretty good at this."

I said the last bit with a wink and headed out.

The next two months went by smoothly. My boss took me up on my offer and his Tuesday morning blowjobs were more enjoyable for both of us. I did make a few other small mistakes, but I quickly brought them to his attention, and they were easily corrected. I found myself a bit sad when I realized one Tuesday morning that the meeting wasn't on my calendar anymore. I swung by his office anyways, but he seemed surprised to see me.

"Your punishment and reminder period are over," he said. "It's also clear that you learned your lesson. Go have some coffee. We have an important meeting in a half-hour."

I nodded and walked away, not sure how I felt. On one hand, I knew that this was a punishment, but on the other, I had enjoyed it, and he had too. Plus, every Tuesday night I had gone home and fingered myself to an amazing orgasm thinking about it. The next meeting turned into a major project that left me without time to think about anything besides work for the next three months. It was a major team effort, but I was, under the guidance of my uncle, spearheading a large portion of it.

Three months later, we were wrapping up one of the final presentations late at night. It was not unusual for the two of us to be the last ones in the office. What was unusual was the fact that I couldn't focus. I had been going non-stop for the months, working ten-to-twelve-hour days. Seeing my frustration, my boss stopped me.

"Go home and get some rest," he said. "You look exhausted."

"No. I need to finish this tonight so that it is ready for tomorrow."

"You can finish it in the morning."

"I need to be able to prepare to present it tomorrow, not still be working on it. I just need to blow off some steam clear my head."

"So go do that, and finish in the morning," he said, again.

Frustrated, I threw myself onto the couch in his office. I looked back at him and saw the clear side of his desk. The memory of being bent over it sparked in my mind. Before I could think too much, I stood up and walked over to his desk.

"Actually, can we pretend that I messed up?"

"What do you mean?" he asked, genuine confusion on his face.

I undid my belt and pushed my pants down, making sure to push my plain panties down with them, and bent over his desk.

"Let's pretend that instead of convincing our client that they needed to expand the project, I screwed it up so badly that they dropped the entire thing."

"Are you sure?" he asked sincerely.

"Oh god, yes. This is exactly what I need right now."

He didn't say anything else, but he stood up. When the first smack landed, I let out a small moan as the pain flashed through my body and my cunt spasmed slightly. My first orgasm hit with tears streaming down my face after a minute of hard slaps raining down on my ass. The spanking stopped and I took deep breaths, recovering from the orgasm and the rain of blows that had me shivering and crying. I heard my uncle opening a cabinet and moving things around. I laid on his desk, breathing, trying to regain my composure. I didn't need to wait long before I felt his lubricated dick once again press against the entrance to my ass. I moaned in pleasure as he stretched me open again. My second orgasm hit when he bottomed out inside me, the exquisite feeling of being used, stretched, and stuffed full, with his balls pressed against my soaked cunt, pushed me over the edge again, this one stronger than the last. He started fucking me even as I rode out the orgasm, and I felt another one start building deep inside with each hard thrust. I nearly blacked out when it finally hit me as he exploded inside my ass. I screamed wordlessly in pleasure as shot after shot of cum filled my bowels.

I came to a few minutes later and stood up gingerly. Looking around I saw my boss sitting on his couch, a satisfied look on his face. I kicked off my shoes and pants and stumbled over to the cabinet with the sink. I washed my legs and made sure that my ass was clean as well, but that had to be done more carefully. I didn't bother to wash my flushed, tear-stained face, and headed back to my computer. I didn't even try to sit, but I got back to with. Even with the heady smell of pussy and sex filling the air, and the pain and heat spreading out from my ass, I found myself much more focused than I had been. I finished and showed it to my boss, who looked it over, standing next to me, with one hand gently resting on my sore, sensitive, bright red ass. He pointed out two minor changes, which I made quickly, and we closed things out.