A Southern Man, Not So Gentle Ch. 02

*For a fan, Arthur, and for the world in lock down*

----JESSIE---

Things between Jack and I had just begun, but I knew I was falling for him hard. He was everything I had wanted in a man, and I didn't even know what I had wanted before I met him. He was strong, handsome, intelligent, and his dominant side was really starting to turn me on. I had heard a few things about BDSM here and there, but experiencing it was a whole other world. I liked that Jack was a dominant man. He was real sweet to me, but also very confident and stern when he needed to be. Jack had started doing things like, picking my outfits for me before he left to go work on his farm if he had spent the night over. Things like this started to give me that needy feeling in my pussy and make my panties wet before I had even left the house. Jack was something new, someone that was so fun and spontaneous. He made my head spin sometimes, just with the feelings I would get being with him. He got me out of my shell and started to push me to my limits, which made me grateful that I had even met him.

---JACK---

I couldn't believe how well things were going with Jessie. She seemed like the women I had been waiting for my entire life, and she just so happened to show up out here in the sticks. So far, she had fulfilled all the challenges I had thrown her way. Even when I asked her to call me Sir, even out in public. I could tell Jessie was shy about certain things but seeing her blush from the slightest humiliation made my cock twitch. I could tell she wanted to be a good girl for me, and I loved that. Jessie was starting to get used to the idea of me having some control over her life and in fact, I think she was really starting to like it. I found her pouting for attention, more often than not. I had not taken her to my dungeon yet, which I had decided to call the playroom, because I could tell Jessie was more of baby doll than some sort of slave. I liked that she was my little lady. I would take care of her and give her more pleasure than she could even imagine, and I know I would receive the same back from her.

---JESSIE---

"Jaaackkk, are we even going to catch any fish today?"

He chuckles, "You have to be patient baby doll, it's only been 15 minutes. I promise you; we will be having fish for supper."

"Don't laugh at me! You know I am new to this stuff Jack. I like it, but only if I'm actually catching something. I thought fishing would be easy!"

"It is easy darling, if you'd just shut that pretty little mouth of yours." He gave me that heart melting smile again and I couldn't help but get a little excited by his comment. Maybe I could get this fishing over with quicker if I tried real hard.

"No, I will not shut this pretty little mouth! Catch me a fish Jack, since you think you are the master at everything." With my hand on my hip, I shot him a big bratty smile that I know would get his blood flowing. Every time I give this southern man a little city attitude, he wanted to break me of it, and I wanted that now. Jack just looked so damn good out here in the Georgia sun, the light off the water glistening on his naked chest. He had just the right amount of chest and tummy hair on his toned and tanned physique, only wearing a pair of tight jeans with boots. I never got tired of looking at this man.

"Babydoll, I know what you are trying to do and believe me you are going to get what you want... Right after I catch a few fish, I will hook you too."

"Ugh fine! I will sit here patiently," giving my best pouty face and sitting down on the cooler, wondering how he was going to 'hook' me.

"That's a good girl now."

---JACK---

I could tell Jessie was trying to be a little brat just to get me to take her home and fuck her, and so she could avoid having to keep fishing in this heat. Her plan had almost worked, because she looked so sexy sitting there pouting. Her in a tight white tank top, with no bra as I had instructed, and very short jean shorts. She had really started to become a wanton little lady and I was loving every minute of it. I was certainly going to teach her a lesson by making her wait until I caught a few fish though, but I was going to give her exactly what she wanted, and maybe a little bit more. I would finally show her the playroom, equipped with all new toys I had gotten just for her, specifically the anal hook. I would teach her the patience in the art of hooking a pretty fish in the honey hole.

"Alright babydoll, I think we have caught enough for me to whip up us a good supper. Are you ready?" Jessie had finally stopped pouting and accepted that fact that we were not leaving, and eventually she caught her first fish. She was so adorable, jumping up and down, tits bouncing, huge smile on her face, over this fish she caught. I couldn't help but smile knowing I had been the one to teach her how. Now all I wanted to do was take her home, punish her for pouting, then reward her for being a good girl.

---JESSIE---

When we got back to Jack's house, I could tell he was acting a little weird. He was awfully quiet while gutting and filleting the fish. Jack being silent made me a little wary, maybe I shouldn't have tried to be a brat and pouted. I was feeling a little guilty about it now because it turned out to be fun and I caught my first fish all thanks to him. I should just listen to him more often, but I think it's in my nature to try and push buttons just a little bit.

"Everything alright, Jack?"

"Yes, of course baby doll."

Jack still wasn't giving me an explanation, so I figured it was nothing. He was an amazing cook, the fish turned out delicious, and I think it was one of the best meals I have ever had. Damn, why does he have to be so perfect?

"Thank you, Jack."

"For what, babydoll?"

"Making me stay with you fishing and for this amazing dinner. I am a lucky girl."

"Yea, about that little lady, I still haven't forgot about that little fit you threw earlier."

"I'm sorry Jack, you know I get inpatient sometimes. It's a city thing, everything moves a lot faster there, but I had a lot of fun!"

"I think you mean sorry Sir, don't you baby doll?" He stared right into my green eyes with his blue ones. He was serious, I could tell. I could always start to tell when his demeanor changed, and his dominant side was coming out more. Sir, that means I am probably about to get punished for being a brat earlier. Secretly though, that is what I wanted, but I was still nervous. I could feel myself get wet as he referred to himself as Sir and gave me that look.

"...Yes, sorry Sir. It won't happen again; I like fishing now!"

"I'm sure you do little lady. You were so cute when you caught your first fish, but I think I need to teach you a lesson about patience that won't be so easily forgotten, don't you?"

I started to look down at my lap before he grabbed my face by the chin and aimed it at his, "...Yes Sir."

"Now that's my good girl. Are you ready to see my playroom?"

I got giddy after Jack said this. I had not seen his playroom yet. He had referred to it a few times but was wanting to wait until we were more comfortable with each other. It's a good thing he kept the door locked or this nosey brat would have already taken a look inside. I may have already tried once or twice when he wasn't looking.

---JACK---

I could see the excitement light up in her eyes when I said 'playroom'. Even though I was about to punish her, the anticipation of seeing the playroom had built up so much she didn't care. I took her by the hand and led her down the stairs to the basement, where I had built the playroom. I had made some changes since meeting her. All new toys, things I knew she would like. I had added things in brighter colors, such as pink, as I knew Jessie would like that better. Before the dungeon had been exactly that, dark and taunting, but with Jessie I had started to change how I thought about myself in the kink world. I didn't want to be this hard master, I wanted to take care of Jessie, she was my babydoll and that's how I wanted to treat her. This was all sort of new to me too, as I have never had this type of dynamic with a submissive before. I was finding it more and more something that came natural to me, and to her too, I think.

When we got down to the last step of the stairs and you could finally see everything on display, I waited to see what Jessie's expressions would say about what she was thinking.

---JESSIE---

I was surprised to see all the obvious work that Jack must have put into this. There were toys and different instruments, that I had never seen before, hung up around the walls. I was expecting it to be dark and scary, but it wasn't at all. In fact, it was the opposite, I felt invited to start walking around and look at everything as Jack stood and watched. The walls were grey, but everything else was so colorful. I see pink collars and leashes, butt plugs of all sizes with little colorful gems on the end of them, and a white paddle that said baby doll on it. I blushed and smiled at the fact that I know it was for me. There was a bed in the corner of the room with a grey and pink blanket on it, I wonder if we would end up sleeping in here sometimes... There were different types of hooks and cuffs all over the room, the bed, the ceiling. Various vibrators and dildos, of all colors and sizes, laid out on a wooden dresser. There were a few things that did intimidate me a little, a leather handle with thin leather straps connected to it, that I could only imagine being used for spanking. Many of the things Jack had here, I had never used before. I was eager but anxious all at the same time.

"See anything you like, babydoll?" He whispered in my ear, putting his arms around my waist, grabbing me from behind. Jack's voice and hands around me made me jump a little and brought me back into reality.

"Mm yes, I really like it Jack. I think we could have a lot of fun in here but might have to take it slow with some of these things. I have never used most of this stuff."

"I know, I will take it slow. This is all for your pleasure, as much as it is for mine. I promise."

Jack's words were reassuring to me, and I knew that I could trust him no matter what. I knew he wouldn't hurt me, at least not more than I wanted him to.

---JACK---

I was pleased when Jessie walked around the playroom. It was obvious she liked what she was seeing, and I was happy to know that. I was going to enjoy this too much. I lead her to the base of the bed that had a cushioned bench that opened and held other goodies.

I sat down on the bench as I commanded, "Undress for me baby doll."

I could tell Jessie was nervous, especially since I was leaving all my clothes on and making her undress in front of me. She started to comply, as I knew deep down, she wanted to. She started with her shirt, slowly lifting it over her head. She had an such perfect tits, a perfect handful for my large hands. Her tan soft skin and long wavy brown hair. I could tell she was getting shy, but she never stopped. Jessie unbuttoned her pants slowly letting them fall over her curvy hips, revealing a hot pink lace thong. I could feel my cock growing in my pants, this was going to be hard for me as well. I am tempted to just fuck her right here and now, but I wasn't going back on punishing her, or she would never take it seriously.

Standing up and touching her pussy through the front of her panties, "Mmm on second thought, leave those on. You are such a good girl undressing for me, and I know you wore those just for me, didn't you?"

"Mhm, yes Sir, I did. I like to please you."

"I know you do baby doll, and you please me so well. I can feel your wetness already. Are you excited by this?"

"Yes Sir, very excited. I want you to use all these toys on me however you'd like," as she pushed her hips harder into my hand, trying to get more friction from my fingers. I could tell it was her pussy talking, as she was being needy and not bratty, for the moment.

"That's a good girl," I whispered as I took my hand away, making her moan and pout a little. "Now get on your knees on the bench, face down onto the bed, knees together."

Jessie quickly complied, getting on her knees on the bench in a comfortable position. I laid my hand on the back of her neck and gently guided her, so her face was on the bed, looking to one side. My cock got even harder at the site of her, ass in the air, pussy wanting attention. I went and got the purple rope from a drawer in the dresser, glad that I had just bought it the day before.

I began tying her feet together at her ankles first, "Now baby doll, you know why you are going to be punished, right?"

"...yes Sir, because I was being a brat at the lake earlier."

I finish tying her ankles, "That's right, and do you know what we do with brats when they act like that around here?" I give her a hard slap on the ass, making her jump up a little.

"Ow! Yes Sir, they punish them Sir."

"Mhm, now be a good girl and don't move. We are going to try something you have never done before."

---JESSIE---

I feel so exposed and vulnerable like this, completely naked, bent over with my ass and pussy up in the air. Jack didn't take his clothes off either, making me feel that much barer. He had tied my ankles and I wasn't sure what was going to happen next. I had a nervousness at the pit of my tummy but the anticipation of what he was going to do to me was making my pussy soaking wet. My face was laid down on the bed so I couldn't see what he was doing now, but I could hear him opening a drawer somewhere behind me. Eventually, I sense him behind me again and look back at him, seeing him squirt some lube on his fingers.

This makes me start to wiggle and move, maybe this wasn't a good idea, "Jack, what are you going to do with that?!"

This gets me three hard slaps on my ass, and I stay still.

"First off, I know you know that calling me Jack is not allowed here. Second, you are my baby doll and baby doll wants to please me, right?

"...yes Sir, but I am scared, I haven't done much anal play before."

"I am going to be gentle, and this is a punishment, right? You are not supposed to love it. Just relax."

Jack was right, so I tried to be still as he pushed my panties to the side and rubbed his lubed finger on my little hole. It felt good, him rubbing it, then he slowly started to work the finger inside. I could tell there was resistance, and knew my ass was tight, as nothing had ever really been in there before. Jack was gentle, like he said he would be. I could feel him work in just the tip of the finger, in and out, slowly. Soon enough, I was moaning a little and his whole finger was now going deep inside my ass.

"Does it feel good, baby doll?"

"Yes Sir, it does feel good. I am surprised at how much I like it."

"Mmm good. I am going to try two fingers now, okay?"

I just nodded into the bed, waiting for the intrusion of the second finger.

---JACK---

Fuck, this was so hot. Here I am, slowly working two fingers into Jessie's tight little ass. My baby doll's ass. She was being such a good girl too. I was astounded at how well she was taking it. My second finger met resistance, but it soon too, was sliding in and out of her ass fairly easily. I was finding myself groaning a little with her moans, wanting to fuck her so bad. It was time to teach her a little lesson on patience though, she was ready, and I must have patience also.

"Now baby doll, remember earlier when you didn't have the patience to sit and hook a fish at first?"

"Yes Sir, I remember, but then I caught one!"

"You're right, you did catch one, but not before you pouted like a brat. So, I'm going to teach you the art of hooking a fish and having the patience to catch one. This is an anal hook."

I moved to the edge of the bed where her face was laying and facing out to the side. I held up the anal hook for her to see, wanting her to know what was going to go in her ass. A large metal hook, with a medium sized ball at one end, and a circular loop to tie rope to on the other. Jessie's face was priceless when she saw it, it even made me laugh a little bit. Her eyes got big, but soon glossed over with excitement.

"You're going to put that in my ass, Sir?"

"Yes, baby doll, just the ball part, and it's my ass."

I moved back behind her and lubed up the metal ball at the end of the hook and her opening again. I gradually worked the ball in her ass, pushing it in a little, then pulling it back out. I was working it into her ass until it slipped in easily and her tight hole closed up around it. She let out a deep moan, and I began rubbing her pussy through her panties. They were sopping wet, making me glad she was enjoying it now, because this next part she wouldn't.

---JESSIE---

I couldn't believe that I was taking all this in my ass. Jack's fingers, and now this anal hook. I was genuinely enjoying it though. He was patient with me and took his time, making it much more comfortable to take. Now he was rubbing my pussy through my panties, and I know I am shamefully wet for him.

"You are soaking wet baby doll. You must be enjoying your punishment a little too much."

I could feel a tug on the anal hook inside my ass. I watched as Jack tied a knot through the loop at the end of it, taking the loose end up the rope, and going towards the front of the bed. At the front of the bed was a hook on the wall a couple feet up, where he tied the end of the rope, making the anal hook real snug in my ass, keeping me in place.

"That feel okay?" I nodded my head, accepting whatever he was going to give me, "Good. Now hands behind your back."

I was hesitant at first, before a slap on my ass got me moving quicker. I put both hands behind me, Jack then held my wrists together with one of his large hands. I could feel ropes start to tighten around my wrists, then tied tight to the hook to where I couldn't move them.

"Now, I think I have you exactly where I want you baby doll. Feet tied together, anal hook secured, and hands tied to it too."

I felt helpless. I was ass up, anal hook in, and could not move without tugging it tighter in me. Just then Jack began spanking me with his bare hands. He gave me 5 hard swats on each cheek, making my ass hotter with each one. I had not been spanked much, but Jack somehow knew exactly how much I could take.

"Now here comes the real punishment baby doll."

"Sir! I thought this was the punishment!"

"No, the lesson is to teach you patience. So, I'm going to go back upstairs, take a shower and relax a little bit until I feel you have learned a little patience."

"Jack, NO! You can't just leave me here like this, and I am ready for you to fuck me, please!"

"What did I say about calling me Jack little lady? And this is exactly why I am going to leave you here for a little while. You think you get what you want when you want it, but not with me. Just for calling me Jack and being a brat again, I think I'll gag you too."

"NO! Please I'll be good." It was already too late. He had grabbed a pretty pink ball gag and was placing it in my mouth.

"There, now it's perfect and you look so sexy baby doll. I will see you in a little while. Remember, this is for acting like a brat, and you are trying to learn some patience, understand?"

All I could do was nod yes and try to get a 'Yes Sir' out from behind the ball gag.

---JACK---

I did feel slightly bad about leaving Jessie, but the guilt quickly faded as I pictured her bratty little ass wiggling around down there. Wet pussy begging for attention and not receiving it. She truly was a little brat, and this might do her some good. In the meantime, I took a shower, drank a beer, until my cock had been hard so long, I couldn't take it anymore either. I wanted to fuck my baby doll.