Please don't forget to leave feedback on the stories you read!

Anna’s Story - A Slave’s Journal Entry 11

New to writing? Post your story here. For first-time authors.
Post Reply
Danicali299
Silver Member
Silver Member
Posts: 53
Joined: Mon Apr 27, 2020 3:37 am
Gender: Male

Anna’s Story - A Slave’s Journal Entry 11

Post by Danicali299 »

Slavery..dark topics…you know the deal

When Thanksgiving finally arrived at the O’Connor house, I didn’t know what to expect. Miss O’Connor had already told me while we were at the grocery store that her family was big, and judging by the three turkeys, bags of potatoes, and frozen sides packed into her cart I didn’t doubt it. She even had me grab a large turkey breast, some frozen vegetables, and gravy for the me and the other slaves to eat for our dinner.

I had never seen so much food being bought for one family’s holiday before, and to be honest was shocked by it all. It sounds stupid to be shocked by that, but me and my mother never actually had a Thanksgiving at home that I could compare this to. My whole life we would go to the community dinner at her church, where we all helped prepare it and get everything ready. It was just how we did things in our community, since we were all so poor that we had to chip in for months ahead of time so we all could get a dinner like that. Now here I was helping Miss O’Connor pickup for one family, what made up a quarter of our decent sized church's whole shared dinner.

On the way back home, I was finally getting used to seeing it that way now, Miss O’Connor was just as stressed as her slaves were about hosting her whole family. She even gave me a concrete number and told me that there were going to be almost 30 people in her house. I dreaded having to deal with that many people, but I still couldn’t understand why she was so stressed when her slaves were going to be the ones doing the grunt work that day. Either way, I still had a job to do and spent most of the ride back home wondering what Edna was going to need my help with while she cooked up all that turkey.

When we got back, Earl was nice enough to help me unload the car while Miss O’Connor rushed inside to go over her dining room for the third time today. After all the food was put away she was still stressing out in the dining room and I took a risk. I hugged her and softly said, “Ma’am, Everything’s good. We have everything setup just the way you wanted it and you don’t need to worry about it. Just come upstairs with me and I’ll run you a bath so you can decompress a little bit”. I half expected her to punish me right then and there, but luckily she realized that a bath would probably be a good idea and came upstairs with me.

Just like the times before, I was expected to get in and wash and massage her, but this time she was more chatty as she vented to me about her family. Apparently, both of her siblings ended up becoming upper management at massive corporations, while Miss O’Connor decided to stay working in an ER. Based on what she told me these people somehow considered her the failure of the family, even though what she did was actually useful to society compared to sitting in an office all day.

I ended up asking her while I was massaging her back, “Miss O’Connor, you tell me about all these horrible things you see there and keep going back to save people every day. Would your brothers be able to do the same?”. She gave me a solid “nope” and then said, “Anna, listen to me very carefully. While I appreciate you trying to calm me down. You can never do this again. Slaves can’t touch their master without permission and you can’t talk to me like that. I have to punish you for this, but since your heart was in the right place I promise its not going to be too bad”.

After her bath I dried myself and Miss O’Connor off, got dressed, and proceeded to wait on the edge of my bed the slave quarters for my punishment. My mind was racing, and I didn’t know if her definition of “not too bad” was the same as mine, so I was almost shaking with fear as I waited for her to come downstairs. Then I heard her enter the room and looked up to see what she was carrying, it was that medieval dildo thing that I hoped I would never see again after she brought it in from the store. I was used to the light shocks from the training collar I used to wear, but this was a real punishment and I knew this wasn’t going to be pleasant. Miss O’Connor could see how wide my eyes were getting seeing this thing she put her hand on my shoulder and reassuringly said, “Calm down girl, I’m only leaving it on until tomorrow morning. Between this and no dinner, I think that should get the point across”.

Then she ordered me to open my mouth wide as she slowly slid this thing’s down my throat until I could feel the dildo triggering my gag reflex over and over again. I instinctively tried to breathe through my mouth as she secured the padlock on the rear of the frame, but that wasn’t possible either. Seeing me freaking out Miss O’Connor grabbed my face with her hands and had me look her in her warm eyes while saying in what I assumed was the calming doctor voice she used at work, “Anna, In through your nose, and out through your nose. In through your nose, and out through your nose. You’re not gonna die, you’re not gonna choke, you’re just going to be very uncomfortable for a little while. Now get back to work and think about how you can avoid this in the future. Understand?”

I gave her a quick tearful nod before we both went back upstairs to get back to our days. I still had to finish a few tasks, and the constant discomfort of my gag reflex being triggered made it harder and harder to concentrate on my work. I couldn’t even swallow with this thing on and felt my mouth get drier as the hours passed by. Eventually I fought through the discomfort enough to finish my work for the day, and hoped to sleep for the rest of the punishment. Unfortunately it’s kinda hard to sleep with an 8 inch dildo the width of a small Red Bull can jammed down your throat, especially while hungry and thirsty, so sleep wasn’t going to happen that night and I already knew that Miss O’Connor planned this as part of my punishment.

The next morning I shambled upstairs like a zombie to make Miss O’Connor her breakfast before she came downstairs. A few minutes later, she came down in her bathrobe and sat at her usual spot at the island and said to me sarcastically, “Wow, you look like you got a lot of sleep last night”. I pretended I didn’t hear that as I put her breakfast and her tea in front of her and began to clean the bacon grease off of the stove. I wasn’t mad at her for punishing me, it was my own fault this happened, but I still didn’t want to deal with her right now. Then she had me turn around and said in that tone she always used when she was teaching me something, “ Anna, I know you probably think I overreacted yesterday, but you’re still new and I’d rather give you the harsh lessons early. It’s easier for all of us this way and you’ll thank me later for this. Now do you think you learned your lesson enough for me to get that off of you?”. I nodded yes like my life depended on it and she said after taking a sip of her tea, “Alright then, after I’m done with my breakfast and you’re done cleaning up the dishes we’ll go to your bathroom and get that off your head”.

Once we were downstairs I couldn’t wait for this thing to be off my head, and I couldn’t wait to get some food in me to shut my stomach up. At first I had no idea why this had to come off in the bathroom, or over the toilet, but as soon as Miss O’Connor slowly pulled the last of the dildo out of my mouth the worst coughing fit of my life overtook me and I was lucky enough not to get sick from it. I sounded so bad that Miss O’Connor even felt the need to stick around and make sure that I was ok. My throat still hurt like hell from the gag stretching it like that, and no amount of water would make the dryness go away, but once the coughing subsided Miss O’Connor thought I was good and made her way back upstairs. After I was done cleaning up I followed shortly after and got back to work.

I still had to make Jessica and Michael’s breakfasts before they came down, and Miss O’Connor was still at her perch in the center of the kitchen reading something on her tablet. While making the pancakes I tried apologizing to Miss O’Connor for the previous day, but she stopped me mid-sentence and told me, “Anna, you screwed up, I punished you and now I’m over it. Now it’s time for you to join that party too”. She then put down her tablet and bluntly said, “One more thing. I see how you look at me sometimes, and I can tell you look up to me like a mother or something when I’m teaching you stuff. I don’t mind it, but you need to remember that I still own you and there are boundaries you can’t cross with me. Do we have and understanding?”.

I gave her a sincere “yes ma’am, and finished Jessica’s breakfast just in time for her to come down and eat. As usual she liked everything I cooked even if it was bad and seeing her mother’s mood asked, “What’s wrong mom, why did Anna get punished yesterday?”. Miss O’Connor replied, “Just some boundary issues that she’s learned her lesson on”. After taking another bite of her pancakes Jessica playfully said, “Aww you’re a good influence mom. You should be happy she likes you. Actually, I have an even better idea. Give her Michael’s life and sell him, then you’ll have two kids who are actually gonna be useful”. Miss O’Connor scolded her for her remark about her brother as she left her plate and went back to her room laughing her ass off. I wanted to laugh as I cleaned her dish but I wasn’t that stupid, even if what Jessica said was both truthful and hilarious. Then after a minute of two of bitching to herself about Jessica’s attitude, Miss O’Connor left the kitchen to get ready for work as Edna began bringing in all the side dishes she needed me to precook for the next day.

It was nice not having to clean the house with how tired I was that day, but just the sheer volume of cooking that needed to be done had me exhausted by the early afternoon. Edna even felt bad for me for once and covered the kitchen for half an hour while I got a sandwich and some nasty energy drink Michael gave me in my system. It tasted like I was drinking gas, but it helped me just enough to keep going. Luckily all that was left was the obscene amount of mashed potatoes I had to make and I would be able finish all the sides before Miss O’Connor got home.

She walked in while I was cleaning the kitchen and I was about to ask her what she would like for dinner, but to my delight she had three pizza boxes in her hands, and a few cokes in a bag. Not realizing that one of the pizzas was for the slaves yet, I internally celebrated not having to cook anymore that day. Then she called Edna and Earl to the kitchen and said to all of us, “You guys have been busting your ass for the past few days getting everything ready. Here’s a little thank you before the craziness tomorrow”. I didn’t expect a reward, let alone really good pizza and the first soda I had drank in a year, but I appreciated it as I savored every bite of this pizza and every sip of that coke she gave me. Then Jessica got out of the shower and requested my presence.

Jessica was nice enough to wait for me to finish eating, but being the creature of habit she was, it was her sex night and I needed to get cleaned up and join her upstairs for another kind of meal. When I entered her room however, something was different. Instead of the normal cuddling, fingering, and eating out, Jessica was putting on something called a strap-on as big as the gag that was just in my mouth and telling me coyly, “We’re going to try something different tonight”. She proceeded to grab some handcuffs and a ball gag from under her bed and handcuffed me face down on the bed with the gag in my mouth.

I didn’t know what was going on behind me after that, but once I felt her lubed fingers enter my ass, I took a deep breath and knew exactly where this thing was about to go. I had no idea how this was going to feel, but I had to try and enjoy this at least. She even reassured me that she would be gentle before she started, but that didn’t mean anything once I felt this thing stretching me inside and out as I made a painful noise through my gag. Jessica could see that it was hurting me and paused for a moment saying, “You need to relax or it’s gonna keep hurting, ok”. I took her advice and tried to relax as best as I could, which made it feel a little bit better, but it was still uncomfortable and couldn’t wait for it to be done. Then for some reason, I my ass contracted a few times as I began to have an orgasm from this of an intensity that I had never felt before. Not long after Jessica had hers, and she uncuffed me from the bed and let me cuddle up with her.

I was still shaking and hurting from the pounding I just had, but according to Jessica, my first time was supposed to hurt and over time I would like it. I doubted that, but her aftercare felt nice as I cuddled up against her chest and kissed her breasts while she played with my hair. I was so exhausted by this point that I even fell asleep while we were cuddling and she let me sleep with her that night. Luckily for me, she didn’t want me to get in trouble as much as I didn’t, so she was nice enough to set an alarm early enough for me to get back to the slave quarters without her mother noticing I was in her room all night.

The next morning, Miss O’Connor let me sleep in a few hours, while Edna and Earl got the snacks ready for the guests’ arrival. Then by 9AM I was up and working getting all the plates and silverware ready with Earl. This wasn’t exactly the fine china and family silver, as Miss O’Connor thought buying that stuff was a waste of money, but the way she had us polish and present it all looked beautiful still. Then it was my turn to help Edna while she was slaving away, no pun intended, over two of the three turkeys Miss O’Connor bought and our dinner as well in a slow cooker on the counter. Earl was currently deep frying the least dangerous looking bird under Miss O’Connor’s overprotective supervision, but I had the task of stuffing these two monsters until I was elbow deep in the things. It was nasty work that neither of us wanted to do, but in Edna’s case seniority has its perks I guess. Afterward we were able to stage all the sides in the old summer kitchen in the garage and all we had to do was get ready for Miss O’Connor’s family to arrive.

As we were doing this, Miss O’Connor had us go and change into cleaner clothes one by one, and for some reason she asked me, “Can you do makeup on yourself without looking like a sex slave when you’re done?”. I should’ve been insulted by that question, but to be honest, the answer was an embarrassing no. Laughing at me for a second, Miss O’Connor said, “That’s ok Anna, I expected you to say that. Go tell Jessica I need her to doll you up a bit for the company”. I gave her a quick “yes ma’am” and ran upstairs to deliver the message to Jessica, who seemed happy to listen to her mother after her joke got her yelled at yesterday.

It was odd to see the young woman who had torn me up yesterday sizing me up like a stylist, but she seemed to know what she was doing as she began trying to match her products with my skin tone. Unfortunately, Jessica was white and I was brown, so there weren’t a lot of products she could use on me but she picked out a few and went to work. She was able to show me what she was doing so I could do it myself later, and with a little lipstick, eyeliner, and mascara she was able to make me look pretty good. She was even able to show me a few styles that worked with my now shoulder length hair beyond whatever crime against beauty I was already doing with my comb, before settling on a traditional braid that wouldn’t get in the way of my work. For the first time in a while I felt beautiful and forgot I was even a slave for a moment as I looked in the mirror.

Unfortunately those moments always have to end, and Jessica had me follow her until I was told to keep out of sight and. I had no idea why until she playfully said to her approaching mother, “May I present your humble servant, Anna, whatever her last name was, for your viewing pleasure”. Miss O’Connor looked amused as Jessica had me come out of my hiding spot and curtsy in front of her like she was my queen. Still laughing at the situation she started inspecting my face and and hair and said, “Damn, I was right. A little bit of makeup did wonders for you girl. I want you to learn to look this good every day. Now both of you need join everyone else in the kitchen so we are all on the same page for later”.

I was standing with the other slaves and Jessica And Michael were standing opposite us on the other side of the island. In the middle, we had Miss O’Connor dishing out assignments. First to get their role was Edna. All she had to do was keep cooking and make sure everything came out good. As much as I didn’t like her, this was the perfect job for her since she was objectively the better cook out of the three of us. Earl’s job was to take everyone’s coat and play bartender until it was time for dinner. Then he became a waiter for one side of the table and made sure nobody had to even lift a finger to get more food or even a napkin. Then came my job, and since I was all made up I got to rove around the house and play cocktail waitress bringing people snacks and drinks wherever they were hanging out. Once dinner was being served, I was then supposed to become the other side of the table’s waitress. Then in a twist she said to her kids, “Michael, here’s 100 bucks to disappear for the day so you don’t embarrass me in front of the whole family like last year. Take the car, do whatever, I don’t care. As long as you aren’t here I’m happy. Jessica, I want you to just be your normal self and show off Anna as much as you can to your snooty uncles. And don’t forget to help with the dishes later on, the slaves deserve a little help tonight”. She then looked at us slaves and said with a smile, “If today goes good, I’ll give every one of you 50 bucks and a day off at some point to go to the store and buy yourself something nice with it”. A 50 dollar reward reward for doing a good job? To a free person that’s not much, but to a slave like me that was a lot of money and a lot more motivation to not fuck this up for Miss O’Connor.

After our little meeting, Miss O’Connor’s family started to arrive around 1PM and were almost all here by 3PM. The only straggler was the one I wanted to see the most, Mistress Robins. Until I could see her and personally thank her for getting me into a good home, however, I had a job to do. To be honest, these people exceeded my expectations and seemed more privileged than Miss O’Connor described. If I heard one of these conversations correctly, one of her brothers even said this house was a dump compared to his ranch in Texas. I couldn’t believe that someone could talk shit about their own sister’s home, while enjoying her booze and her hospitality. It honestly made me wonder why Miss O’Connor even bothered trying to impress these people as she circulated around the house trying to chat with guests who were just calling her “poor”and “trashy” before she got within earshot.

Despite my feelings, I still had to cheerfully serve these people while also having the time for Jessica to show me off like I was a new car. It was challenging, but I did well and towards dinner time she finally showed up. Miss O’Connor greeted her at the door hugging her like she hasn’t seen her in a while. This seemed to be the one relative here who didn’t look down on her and it felt good to see Miss O’Connor so happy to see her. By the time she was done greeting her relatives, I was in the garage grabbing more wine when I bumped into her on my way back to the kitchen. She didn’t recognize me at first with all the makeup, but as I apologized for running into her she said with a smile, “Never thought you’d see me again, did ya slave?”. I tried to thank her for getting me into a good home, but all she had to say to me was, “I didn’t do that for your benefit, but I’m happy you work well with this family. You even got your hair back. Now get back to those drinks before those rich assholes get too whiny”.

I didn’t expect much of a reaction from her at all, but I was still happy that she accepted my gratitude. Then it was dinner time. Everyone was seated, with Miss O’Connor at the head of the table, while me and Earl went from person to person filling up their plates with whatever they wanted from the buffet worth of food we had set up in the kitchen. It took a few minutes to get 32 people their plates, but they were patient and in less than 15 minutes everyone was served their first plate. We still had to do fancy waiter/waitress things like put butter and gravy on their food for them, but once everything was staggered it was much more manageable for me and Earl. Eventually we served dessert, which was a homemade peach cobbler that Edna had been working on over the past two days and these beautiful mini pumpkin pies that were just made that morning by Miss O’Connor herself.

After everyone was stuffed and quiet, Miss O’Connor called Edna into the dining room to join me and Earl and made a slightly drunk speech to her family. She said to the whole group, “Thank you all for coming to my home tonight to spend Thanksgiving with me and my family. I may not have the giant ranch in Texas, or vacation homes in the Catskills, but I have my family and my slaves who worked hard for days to make this dinner possible, and I’m thankful for them all. Michael can’t be with us tonight because of the fight he caused last year, but he sends his regards”. She then turned to Jessica and said, ”Jessica, I am so proud of the woman you’re turning into. I hope your internship goes well and you find that perfect specialty that lights your fire and gives you the motivation to push through all the stress and help people every day”. Then out of the blue she turned to me, Edna and Earl and said ,slurring a few words, “Edna, Earl, you two practically raised me and I couldn’t imagine life without you. Sometimes, you two were there more than my own parents and I love both of you for that”. Then she pointed me out and said, “Anna, you’ve only been with my family a short time but you’ve proven yourself to be a hard worker and a good person to keep around, even if you’re a little emotionally damaged sometimes. Adrea [Mistress Robins] made the right choice choosing you to be there for Jessica when she finally goes out on her own and I’m proud to have given you a better life than that slum you used to live in”.

To us slaves, this was heartwarming to hear, and most of the guests agreed with her in being thankful for the people who made their comfortable life possible and raised their families. To some of her other relatives, however, they thought her speech was funny and openly laughed at the idea of being thankful for their own property doing their jobs. A couple of them even jokingly put a couple dollars on the table as a “tip” for us like it was an insult. In the end, Miss O’Conner ended up leaving the table to go upstairs while Jessica and Andrea[Mistress Robins] politely told everyone that dinner was over and it was time to leave. We offered everyone plastic to-go containers of whatever they wanted, but most of these people turned their noses up at the food we made after they weren’t being forced to eat it, with a some even having the gall to try and make dinner reservations for later before they even left the house.

A few relatives like Andrea and one of her cousins stuck around to comfort her with Jessica, but we could see Miss O’Connor crying in the living room while we cleaned up the house. She was crushed, and we were even upset seeing our hard work scoffed at like it was nothing. Eventually, Miss O’Connor got herself together and came into the kitchen to talk to me and Edna. With her makeup still running from the tears she said woefully, “All of you did perfect, it just wasn’t good enough for them. Again”. We weren’t going to ask about the 50 dollars out of respect, but luckily she still gave us all our reward even though we didn’t feel like we even earned it. She even changed into some better clothes and joined Jessica in helping us clean up the mess her family left, saying, “Let’s get this place cleaned up so we can forget this night ever happened”.

She wasn’t the best at cleaning, but we appreciated her help and by the time we were done she had sobered up and looked at me and said, “Anna, I could use one of those special baths right about now. Can you meet me upstairs after you get all that makeup off of you?”. I obliged, and after Jessica gave me one of her makeup wipes I made my way upstairs and found Miss O’Connor crying in the tub as I took off my dress and slipped in the water to start trying to make her feel better. I let her vent as I massaged her, and respecting the boundaries I was to remain within, I offered no commentary beyond telling her that I was going to be alright and other pleasantries. It took a while but I calmed her down, and got her to bed but as soon as I was dressed and about to leave she asked me, “Anna, Can you just hold me tonight? I just wanna feel someone for once when I go to sleep. You can even wear one of my husband’s old t-shirts from the dresser over there if it’s more comfortable for you”.

I didn’t know how to even respond to this, but seeing how bad she was at that moment I went down to just my panties and her husband's shirt and held her under the covers while she was finally able to fall asleep in my arms. A little while later I finally got as comfortable as I could with this awkward situation and fell asleep as well. Hopefully putting this disaster of a “holiday” behind me for good.
These users thanked the author Danicali299 for the post (total 3):
ZeeChromosomeJustBobTauriRed

ZeeChromosome
Platinum Member
Platinum Member
Posts: 219
Joined: Thu Jul 29, 2021 5:42 am
Location: Northern Virginia, Just North of Real Virginia
Gender: Male
Contact:

Re: Anna’s Story - A Slave’s Journal Entry 11

Post by ZeeChromosome »

Dan, great chapter. I'm really getting invested in this character. I feel like you're really starting to tell us more about her and it's really good stuff. Additional comments sent via DM. Let me know if you don't get them.

Zee!

Danicali299
Silver Member
Silver Member
Posts: 53
Joined: Mon Apr 27, 2020 3:37 am
Gender: Male

Re: Anna’s Story - A Slave’s Journal Entry 11

Post by Danicali299 »

ZeeChromosome wrote: Fri Jan 27, 2023 11:26 pm Dan, great chapter. I'm really getting invested in this character. I feel like you're really starting to tell us more about her and it's really good stuff. Additional comments sent via DM. Let me know if you don't get them.

Zee!
I did not, but I’ll give the site a little bit to do it’s thing just in case there is a delay or something
These users thanked the author Danicali299 for the post:
ZeeChromosome

ZeeChromosome
Platinum Member
Platinum Member
Posts: 219
Joined: Thu Jul 29, 2021 5:42 am
Location: Northern Virginia, Just North of Real Virginia
Gender: Male
Contact:

Re: Anna’s Story - A Slave’s Journal Entry 11

Post by ZeeChromosome »

Yeah, doesn't seem to be going through. You have PM's turned off somehow? Email me at zeechromosome@gmail.com if it doesn't work.

Danicali299
Silver Member
Silver Member
Posts: 53
Joined: Mon Apr 27, 2020 3:37 am
Gender: Male

Re: Anna’s Story - A Slave’s Journal Entry 11

Post by Danicali299 »

They’re allowed on my profile. IDK What the deal is with that but I did send you an email so I could read the feedback to see if there could be a few improvements

JustBob
Bronze Member
Bronze Member
Posts: 40
Joined: Tue May 10, 2022 3:36 am
Gender: Male

Re: Anna’s Story - A Slave’s Journal Entry 11

Post by JustBob »

I don't have a lot of feedback, but this is a really good story. Thank you for your work.

Post Reply