The Overseer

A captured slave tells the story of his life in Alabama in the 1800's.

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 14. 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.

Kevin got 20 brutal swats. I was determined to beat that defiant attitude out of him. His bad attitude failed him along about swat number four and he started screaming and sobbing at every swat. Then, somewhere in the process, he came on the floor; his cock spurting its load six or seven times. When he was able to stand, I tied his hands in front of him and stood him against the wall. Ann watched with nothing but fear on her face.

Ann was terrified because she knew she was next. Over the bench she went. I don't know what's up with kids these days, but around swat number 10, she squirted girlee juice all over her thighs. I stopped at 15 swats because a girl's ass is softer and more tender than a boy's, so I had gotten the same amount of reaction from her, that I had from Kevin, with fewer swats.

I stood her against the wall, next to her brother, hands tied. They stayed that way for an hour so they could do nothing to sooth their damaged rears. Then, I sent them home.

And, I went back to my 'making sure everything got done' routine.

I was awakened one night by a screaming in one of the slave huts. I ran down there to find a Mom hysterical because her daughter was very very sick. The sick girl was Malinda and she had a very high fever. Malinda was lighter skinned and smaller than most of the other kids because she was one of Massa Kevin's bastards, so was half white. I had known her most of her 14 year life.

We called the doctor who got there about an hour later. I also sent one of the boys to the main house to let Massa Kevin know. He came about the same time the doctor got there.

Things were different in the 1800's and doctors had a different attitude about things, especially when they were treating slaves. After examining Malinda for a few minutes, he came out of the hut and spoke to Massa Kevin and I.

"She's in the butt of heat, that's all. She needs to get broke in and she'll be fine".

I was surprised, but Massa Kevin accepted what he said. He turned to me and told me to take care of it.

I asked Massa Kevin what he meant and he said, "take her to your hut and break her in. The doctor says that's what she needs and we can't have a sick child around. She won't be able to work."

"But sir, what if she gets pregnant?"

Massa said, "if she does, she does and you'll have a permanent house wench for yourself. As a matter of fact, you keep her after you break her in. You've been alone since you've been here. It's time for you to mate up".

And, with that, I told the Mom to get Malinda cleaned up, get her things together, and send her to my hut. I also told Mom to get rid of Malinda's pussy hair. I didn't like hairy pussies and, if she was going to be mine, she was going to be hairless down there.

It was two hours before Malinda got to my hut. I guess it had taken her Mom quite a while to clean her up and shave her. I imagine Mom also took some time to explain sex to her too.

She still looked sick when she got to my hut, so I wanted to help her get better first. I told her to put her things away and get ready for bed. She asked me where she was to sleep. I told her, "Massa Kevin says you're going to be my mate, so you'll sleep in my bed with me. So, take your clothes off and get to bed girl".

She had a scared look on her face, but did what I told her. When I got undressed and climbed into bed next to her, she was surprised when all I did was cuddle her next to me. She was burning hot, so I made sure she had plenty of water to drink and just hoped her fever would break on its own.

I had never seen Malinda naked before now, but she had a great body. Almost flat chested, she had big, dark nipples that stood straight out and we're about thumb sized. Her belly was flat and hard and she had a rounded ass that begged to be touched. I knew her tits would fill in nicely as she got older.

"Aren't you going to do me, Mr Charles"?

"First child, you're my mate now, so you call me Charles, not Mister. And, I want you to get well before I break you in. It's going to be rough enough for you and I don't want it to be worse because you're sickly."

"Yes, Charles. Thank you for caring about me." We fell asleep with me on my back and her on her side, facing me, with her head on my shoulder.

I woke up in the middle of the night to her gently stroking my cock. She must have been doing it for a while because I was as hard as a telephone pole. With one hand, I began massaging her lower back and ass and, with the other, reached between her legs and ran my finger up and down her virgin slit.

Malinda must have been awake and thinking for a while because her pussy was soaking wet. If she wasn't in heat before, she definitely was now.

I pulled my arm out from under her head and rolled her on her back under me. She spread her legs and I lay between them, looking in her eyes.

"My Momma told me I should be on my hands and knees when we do it."

"That's how people breed when they don't care about each other, Malinda. Since you are my permanent mate, we're not just having sex; we're 'making love,' which is a lot more. Do you understand?

"I think so."

"I wish I didn't have to Malinda, but this first time, I'm going to have to hurt you - to turn you into a woman. I promise to make it as quick and gentle as I can."

I rubbed my huge cock against her tiny pussy until I found her opening. I had to push hard to get her pussy lips to separate enough to get the head of my cock into her. When it did, there was almost an audible "pop" and tears came to her eyes, but she didn't cry out.

I hooked my arms under her knees and pushed them back until they almost touched her tiny tits. That opened up Malinda's hips. I pushed hard and buried about four inches of cock in her all at once, breaking through her hymen and causing her to scream. I knew it was loud enough for people in the other slave huts to know what had happened.

I held still for a few minutes even though her pussy was squeezing my cock painfully. Damn, she was tight. But, I was going to fix that. I tried to comfort Malinda by looking into her eyes and said, "the hard part is over. As soon as you're ready, I'm going to give you the rest of my cock."

I didn't have to wait. After she had taken a couple of minutes to get use to the invasion of her body, Malinda's hips started moving. She wrapped her legs around my waist and pulled towards me, gradually burying more and more cock into her incredibly tight pussy. All I had to do is hold still; she wanted it and she did all the work to get it.

In about ten minutes, our bellies touched together and my balls slapped against her ass.

Now it was my turn. Slowly, I pulled my cock out of her until only an inch or two remained; then, I pushed back in until I felt her cervix. In and out. In and out. In and out, until I felt my cum rushing down my cock. Spurt after spurt of man creme flooded her, trapped by my cock that was plugging her pussy. I felt her cum at the same time, her girlee juices splashing all over my balls as she squirted over and over.

We laid there, breathing hard and kissing, while my cock gradually softened and popped out of her pussy. I rolled off her and laid next to her. Both of us looked between her legs to see her pussy gaping open with a mixture of sperm and virgin blood running out of her. It was going to take quite a while for her pussy to shrink back to its 'pre-fucked' size

Malinda looked up at me and said, "Can we do that all the time?"

"Of course we will."

And, I went back to my 'making sure everything got done' routine.