The Overseer
by Flier1948
Copyright© 2026 by Flier1948
Fiction Sex Story: In 1855 Alabama, a slave becomes the overseer responsible for the women and children slaves. He controls them and finds a mate in the process.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa Ma/ft Slavery Heterosexual Fiction Historical Spanking Black Male Black Female First Oral Sex Pregnancy .
Life in Alabama in 1855 wasn’t too bad, well, it wasn’t now anyway. My name was Olatunji when I was captured in Africa five years ago. I’m called Charles now. When I got to America, I was sold to Mr Kevin Nichols. His wife is Miss Catherine.
Luckily, I wasn’t put out in the fields. I knew how to cook and am very organized. Not to mention, I was a Prince in Africa and the other slaves who were captured with me knew it and respected me. So, I became the overseer for all of the female slaves and the male children until they’re 12. After that, the women stayed working in the main house and the slave huts while the males went to work in the fields
The women on the plantation take care of the house, the cooking, and the slave quarters, making sure everything is cleaned every day and the master and misses have every whim catered to. And, it’s my job to make sure they do it.
The male field hands have a rough life. They work hard, maybe 12 hours a day. The field bosses treat them terribly and the whipping post is where they end up if they need to be disciplined. I never liked that. The whip would strip the skin from their backs and leave scars that lasted forever.
Of course, there had to be discipline for the women and young boys too, but I handled that with my trusty paddles. The fear of getting their ass worn out by me was what kept them in line; well, most of the time anyway.
Today was just one of those days, I guess. Mistress Catherine called me to the main house because of trouble between two of the house girls. One was Phoebe, who was about 25 and the other was the oldest house girl, Hannah, who was over 50. They had actually gotten into a physical fight over something stupid. Mistress Catherine wanted them disciplined and right now.
I told the two girls to follow me out to my cabin in the slave quarters area. By the time we got there, both of them were pleading with me, but we were way past that.
In my cabin, I had a table, shorter than a normal table, that I used as a work area, but also for paddling when needed. I told both of the girls to pull off their dresses; there was no need for them to remove underwear as the slaves never wore any.
Hannah was the one who should have known better; she was going first. She is a big woman with a hugely wide ass. I bent her over the table and quickly tied her hands to the front legs and her knees to the back legs. Spreading the knees that wide tightened up the ass skin like a drum and spread the cheeks apart to expose the tenderest skin between the ass cheeks.
She was sobbing and begging, but I wasn’t there to decide if they should be paddled; Mistress Catherine had already done that. I was there to make them wish they had never gotten into a fight with each other.
My paddle for the adults is about 3/4” thick with a business end about 30 inches long. It has penny sized holes drilled in it for the skin to pop through which created blisters that would last long after the paddling was over.
Hannah’s ass cheeks were clenching and unclenching, as she wiggled as much as she could, and her asshole was doing a winking motion. She was ready.
Hannah’s butt was so big that my paddle would only cover one side at a time. It was going to take six swats to cover the entire expanse of it, so I told her that she was getting 24 swats; enough to punish every square inch of her ass four times. I didn’t really like putting the wood to the older women, but she had to stay in line, same as the rest, or Mr Nichols might decide to send her to the whipping post.
She was in the middle if begging when I reached back as far as I could and slammed the first swat into the top of one cheek. It dented the flabby flesh of her butt about an inch and shut her up in mid-sentence as she inhaled deeply. When she exhaled, she screamed like someone had branded her with a hot iron.
She was in the middle of more begging when the second swat landed on the same side, but where her cheeks met her thighs, the ‘sit spot’. Another massive inhale and another animalistic scream.
The third stoke landed between the first two and even overlapped them a little. Hannah was hysterical, choking and sobbing out random words that made no sense.
I repeated the same process on the other cheek of her ass with the same results. I was determined that she remember this ass beating for a long long time. By the time I was half way done with her punishment, dark blisters were forming on her dusky black ass cheeks; blisters that would keep her sore for a week or more after the initial pain left her ass.
Phoebe was standing next to the wall watching what was happening. I saw her knees get weak as she was already sobbing, just thinking about her being next.
By the time I was done with Hannah, her breathing was labored as her sobs made it difficult to inhale or exhale. She was too weak to stand for about 20 minutes. I released her from the table, but left her hands tied together in front of her so she couldn’t reach back to sooth her damaged rear. She’d remain tied for an hour to let her think about what she did to cause the burning and itching in her ass.
I stood Hannah next to the wall; it was Phoebe’s turn. Phoebe was much younger than Hannah, so her ass wasn’t nearly as big or nearly as tough. It only took four swats to completely cover her ass which meant each area was going to get pounded more often than Hannah’s. Phoebe didn’t fair nearly as well as Hannah and I had to stop three or four times to throw water on her head when she passed out. About halfway through, she peed herself.
After they had both spent their hour thinking about their damaged asses and Phoebe had cleaned up her mess, I told them to get back to the main house, apologize to Mistress Catherine, show her that they had been punished, and get back to work. And, I followed that with, if I have to whoop them again for the same reason, they will get twice as many swats. With that, they put their dresses back on a hustled back to the main house with their hands rubbing their burning behinds.
And, I went back to my ‘making sure everything got done’ routine.
Then, one afternoon, one of the older wenches came to talk to me. She has two children, Joshua and Ann, and was concerned because she had caught them, more than once, fooling around naked with the other teenagers. Joshua was 15 and Ann was 13. Ann had just gotten her blood so both were old enough to breed, something that wasn’t allowed without Massa Kevin’s permission.
I had Mom send her kids to my hut after dinner the next night. They knew why they were there and were fidgeting around, unable to stand still.
“What’s the matter with you two? Joshua, you could get a girl pregnant and Ann, you could get pregnant. If either one happened without Massa Kevin’s permission, you’d be in a lot of trouble. Do you have anything to say for yourselves”?
Ann spoke up first. “No sir. It just feels good and I’ve been having these urges”.
“Me too”, said Joshua, “and the wenches, they want it.”
“Well, I’m going to give you another feeling to think about. A feeling that you’re going to feel every time your Mom tells me she caught you naked with another child. Now, get undressed, both of you. Everything off”.
Joshua had a defiant look on his face and Ann started sobbing as they both got naked.
I put Kevin over the paddling table first. For some reason, his dick started to harden as I was tying him down.
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