Dear Diary Ch. 03

Alexis warned Janice not to cum yet. I could tell by her sounds, her smell and the amount of juice she was spreading on my face that it would be a struggle for her. A selfish part of me wanted her to cum without permission so we both would earn a punishment. Having us simultaneously being over our Mistress' knees for a spanking was appealing to me. Just knowing that she was submissive to younger girls made me want to see her spanked. But before she couldn't help but climax, she was saved by the return of Christine and Megan. I wasn't sure if that was good for me or not, but Janice was clearly disappointed that she was denied the climax she craved. Like me, I'm sure she was excited for whatever the weekend would bring, but that doesn't mean having to wait again to cum was her preferred option.

"We are ready, Mistresses," Christine announced.

"Megan," Alexis added, "Be a good girl and get Janice off."

Alexis turned Janice so her ass was now in my face and Megan could drop to her knees in front of her. I couldn't see what she was doing, but it wasn't exactly a secret.

"Spread her asscheeks and lick her asshole," Kim commanded me. I honestly didn't remember if I ever had rimmed Janice before. I'd rimmed her husband, but at that moment I couldn't remember if she liked it. That didn't stop me from complying. I was sure Megan was well skilled in the oral arts. I knew this wouldn't last. The only question in my mind was if Janice would be allowed to cum or if Alexis was just teasing her. In under 30 seconds Janice was begging for permission to climax. Unsurprisingly Alexis did not grant that permission immediately, but thankfully for Janice, she didn't make her wait too long. Maybe about a minute. I don't think Janice could hold back much longer so I theorized that Alexis didn't want Janice to fail. That meant, at least for now, I was the only one that was going to be punished.

When Janice moved away from Megan, she looked like a glazed donut. Janice's orgasm was definitely juicy. I was jealous as my face had mostly dried, but instead of Janice's arousal lingering on it, I now had Janice's ass scent. Alexis told Megan to stand and Kim tugged on my leash indicating I should rise. I had expected to have to crawl behind her, but when Christine opened the door, I realized we were going outside, so walking was more appropriate. I felt my skin tingle in the chill of the night air. Weirdly I had no worry about being naked. I knew Kim would protect me, but we were far from the prying eyes of a usual neighborhood. I wondered if they were taking us somewhere. Maybe we were going to some kind of kinky party. Instead we walked past the car and about 50 feet past the back to the house. I could see a barn in the shadows. Was that our destination?

Without the aid of a flashlight, our progress was slow as the ground was uneven. Thankfully there was grass so my bare feet didn't encounter any stones or branches. Finally we stopped and I saw Christine open a door in the ground. As she swung it up, I saw a dim light coming from underground. It was then I realized it was an old root cellar. I didn't realize they still existed. There were stone steps leading down. They were a bit rough on my feet, but not too bad. What really was bad was the rapidly decreasing temperature as we descended the stairs. Yes my body was overheated in the house with all that had happened, but it was quickly cooling off since I lacked clothes to protect me from a natural refrigerator.

The girls had set up several candles as there were no electric lights. In old English literature I had read as a child, root cellars were always described as having built in shelves where food was stored. It looked like these had been removed on three of the walls but the fourth still had its original three level shelf. The walls were a mixture of Earth and stone installed to create structure. The roof had wood beams and an old wood ceiling on top of it. I knew the house was built in the early 1900s so I assumed this cellar was that old as well. It had to be over 100 years old, but it seemed as strong as the day it was built. There was high humidity from being underground, so the stones were damp to the touch. The stones glistened in the candlelight. I didn't understand why we had come down here until I noticed two leather cuffs that had been attached to one of the beams.

Looking closer I noticed several modern carriage bolts had been installed through some of the beams. These were probably to hang things the farmer once stored down here, but now were repurposed for our kinky needs. I also noticed a spreader bar leaning against the shelf and several whips and assorted sex toys on the shelf. Then I realized the cellar looked like a medieval dungeon. My knees went weak and I swooned. Thankfully Mistress Kim caught me.

"That's right, my pet," she cooed. "It's time for your punishment for losing the contest."

In short order my wrists had been cuffed using thick leather cuffs above my head and spread just over shoulder width. Similarly my ankles were cuffed using the spreader bar a similar width apart. Basically I was in a standing spread eagle in the middle of the cellar. My Mistresses could walk around my body with plenty of room to tease and torment me. Mistress Kimberly was in charge, but she quickly delegated my punishment.

"Mom," she began, "you won the contest so you get first crack at this slut. I know you are not as into dominating women, but I want you to flog sweet Katie for two reasons. First, she lost the contest. Second, I want you to learn how to do it properly so that you can better continue her training while I am away."

I saw Alexis hand Janice a leather flogger. I didn't get a great look at it, but it appeared to have about 20 tresses, each about three feet long. I felt a shiver go through my body and I didn't think it was because of the cool air of the cellar. Kim motioned for her to walk behind me while the four coeds stood in front of me to walk my reactions. Did I say watch? I meant Christine was recording on her phone.

The first strike wasn't that firm. There was a little sting and my reaction was mostly surprise since I couldn't see Janice begin her swing. Kim took notice and began instructing her on how to hit me harder. She also told Janice to make sure not to strike my kidney areas, but that the top of my back between my shoulder blades, my ass and my thighs were fair game. Janice became more forceful as she became more confident and each impact turned on more and more nerve endings in my body.

After about 10 minutes, Kim told her to stop. She walked forward and slid two fingers into my pussy. I knew I was soaking wet from the flogging so I offered no resistance to her probing fingers. Her purpose was not to please me, unfortunately, but after coating her fingers she pulled her fingers out to show the girls how much my punishment was exciting me. A normal woman may have been humiliated when the girls clapped at her display, but I was not. Any humiliation about how my body reacted to Kim and Janice had long since passed. Kim did say obviously I was enjoying my punishment too much and that they would have to try a new approach. That concerned me.

Janice was ordered to put down the flogger. As she returned it to the shelf, I saw Alexis pick up a riding crop. Kim also picked up a small vial. I wasn't sure what it contained, but I was sure it wasn't good for me. Alexis also told Megan to take a picture of my back. She walked behind me and then moved around in front of me holding her phone so I could see it. My backside was red, although due to the style of the flogger, there were no individual marks. Janice had been fairly consistent about striking me in a balanced fashion. I imagined that I would bruise later, but for now, all I felt was heat.

Kim had a wicked smile on her face as she held up the unlabeled vial. She unscrewed the top and squeezed the rubber tip drawing a clear liquid up into the attached pipette. I was wondering if the vial contained a liquid form of Ecstasy or another drug. When she snapped her fingers in the direction of Christine and pointed at my nipples, I realized it probably was something I had read about but never tried. I had never wanted to try it either.

My nipples were already stiff, but Christine rubbed her fingers across them anyway making them marginally firmer. She then did the same to my clit. It had already been peeking out of its hood. I would be lying if I didn't enjoy her attention even though I wish it had been for a different reason. Kim now put two drops of the mystery liquid on each of my nipples and three or four on my tender clitty. Janice then handed her a butt plug. It was smaller than I would have anticipated. It's funny how you look at something like that and think "that will go in easily." But as my nipples started to heat up, I realized stretching me wasn't the purpose. One of the girls was already fingering my asshole. They didn't lube me up. I suppose that was so the liquid wouldn't be diluted. I guess that's why a small plug was called for. In any event, the plug went in without a fight. My nipples were on fire at this point and my clit was heating up. I knew my ass would soon join them. Later Janice would tell me the vial contained ginger root extract and they didn't bother putting it in my pussy because my juices would have washed away most of the effect.

As it was, three of my erogenous zones were on fire while Alexis started using the crop on my ass. Not to be left out, Kim picked up a second crop and went to work on my tits, tummy and thighs. Megan was recording the event while Janice was kneeling in front of Christine and was eating her out. Kim took caution not to crop my nipples or clit. I guess she figured the ginger was doing enough to drive me crazy. That's not to say she didn't come very close, however.

The combination of heat from the ginger, heat from the impacts and the plug in my ass (even though it was small) was making my pussy drip. I held out as long as I could before begging to be allowed to cum. It was probably two minutes. I knew I wouldn't get permission, but I had to ask. Kim's response was a direct snap of her crop on my right nipple. Fire from the sensation shot through my body and I cried out in pain. But that did little to quench the need in my pussy. She hovered the crop over my left nipple while staring at my eyes. I knew she was asking for consent to crop my left nipple. I didn't want to give it to her, but I could not resist the look in her eyes as they bore through my soul. Exasperated, I finally released a deep breath, nodded and lowered my head.

The snap seemed even firmer than the first time. I know my yelp was louder. All strength left my legs as I hung by my wrists until the pain passed through my body. As I recovered enough to stand again, Kim began rubbing the crop across my clit. My body reacted as you might expect.

"Does my pet want to cum?" Mistress Kim cooed. She obviously knew the answer and was teasing me with her words as much as with the crop. I also knew that implied with my acceptance of her offer was likely a direct cropping of my pussy. As much as the strikes on my nipples hurt, I wasn't sure that exchanging similar treatment of my clit was worth the endorphin release of an orgasm.

Part of me wanted her to just crop my pussy without my consent. After all, subs don't usually have a say in their punishment. I struggled to bring myself to consent to her continued abuse of my body. As usual, she seemed to sense my emotional predicament and take action to make my decision even harder. Or maybe it was easier. She told Megan to help her Mistress put on a cock. I think Kim and Alexis had discussed this plan in advance because Alexis didn't say a word but I soon felt her strap-on sliding into my pussy from behind.

Kim started tapping the crop on my clit while Alexis took hold of my hips. As Alexis began fucking me, Kim started using a bit more force in her taps. Not enough to cause pain, mind you, but definitely enough to drive my arousal higher. Alexis was taking her time. Instead of the rough fuck I expected (craved) she set a slow and steady cadence pulling the dildo almost all the way out and then sliding it back in as deep as it would go. As my arousal built, I realized the girls knew exactly what they were doing. If I told my Mistress to fully strike my clit, I bet Alexis would have slammed her cock into me. Thus I had a quandry. Excruciating pain on my clit in exchange for the rough fuck I needed. My mind started riding the pleasure wave the coeds were giving me and not concentrating on showing another level of submission to my Mistress. I was getting close to a very satisfying orgasm. I kind of thought, if I told Kim what she wanted to hear, I could cum on the first strike of her crop. I knew that was her goal. Well, maybe orgasming after a couple of strikes. She always liked exploring the pain/pleasure principle.

One thing Mistress Kim was exceptionally skilled at was reading my mind when it came to what I was thinking and how my body was reacting to a specific situation. That meant just as I approached giving her consent to crop my clit, she told Alexis to pull out and to also remove the butt plug. I couldn't see behind me, but I hope Megan got the pleasure of licking my juices off the dildo. Kim gave me a passionate kiss and slid two fingers into my needy pussy. "Soon pet," which whispered in my ear. I moaned. She then removed her fingers and wiped them on my lips. She had that evil little smirk she often had when tormenting me. I had a love/hate relationship with that smirk. It made me feel like she never intended to let me cum yet. When I was released from the bondage, I knew I had more to endure before my pleasure.

As it turned out, endure wasn't really the correct word. Earning my pleasure was more appropriate. The group went back to the house. The five women, basically everybody but me, sat down in the living room on the sofa and love seat. Kim spread her legs first. Rank has its privilege. I was promised I would get to cum after I got all the women off. They were seated in my perceived order of their positions in the group. Alexis was next to Kim and would be second. Christine and Megan were next, although I perceived them to be interchangeable. Christine belonged to Kim so maybe that was why she was third. Or maybe that's just how they sat down. Janice was last, but I never tired of licking her pussy, so I certainly didn't mind.

The girls carried on casual conversations about school life and mutual acquaintances as I worked to get them off as quickly as I could. I wanted my reward and saw that happening once Janice orgasmed. I got Kim off pretty quickly. I knew what she liked after all. Alexis, Christine and Megan were tougher and I just had to rely on raw skill instead of inside knowledge. Megan came very quickly. I think she was just a slut :-)

Janice came quickly too. Like Kim, I knew just how to make her cum when I wanted to instead of prolonging my time between her legs. I prayed I had earned my reward and I had. It just wasn't exactly how I envisioned it going. Mistress Kim always kept me surprised. She ordered me to move a couple feet away from the couches and to lay on my back with my legs spread. As I moved into position, I realized how lewdly I would be displayed showing them my soaking pussy.

"You are to masturbate and show us how desperate you are to cum," Mistress Kim commanded. That seemed easy enough. I'm sure her intention was to make me beg like the slut I was born to be. That certainly was part of it. I kind of expected them to toss me a dildo so I could fuck myself for their amusement as well. Instead Kim handed me her crop. I didn't even notice she had brought it with her from the cellar.

"You have permission to cum when you are ready, but not on your fingers. You will cum by striking yourself," she told me. "You may cum more than once, if you want, but the same rules apply. Fingers can get you close, but the crop has to make you cum."

A wave of pleasure flowed from my clit to my brain as I began to rub it faster. Kim's plan was diabolical. If I wanted to cum, and I did obviously, I would have to strike myself hard enough to trigger the appropriate pain response. If I did it too hard or too soft, my permission might be rescinded. In a way, it would have been much easier for to have Kim crop me while Alexis fucked me. That way I wasn't responsible for my body's reaction to those stimuli. But doing it myself meant I was in control of my lewdness. And of course, the event was being documented via video.

You would have been proud of me, gentle readers. I lasted at least three minutes rubbing my clit with my fingers. As required, when I knew I was on the precipice of a wonderful climax, I grabbed the crop. Admittedly my first attempt to strike my clit missed. I got more inner thigh than dripping pussy, but since my thighs were wet from my leaking juices, the instrument still made a sloppy noise and elicited cheers from my voyeurs. But that wasn't going to get me the orgasm I craved. I swung again. My aim was much better, although I am sure I wasn't as forceful as Kim would have been. Still, the razor sharp bolt of pain shot through my clit to my soul. It didn't go to my brain. It was much deeper than that. It was primal. But I didn't climax.

Snap three was also well aimed and this time with more force. Probably 50% more force. Although the pain was perhaps worse than anything I had ever felt, I moaned instead of crying out. I recognized that I was falling into subspace. As I did, my strikes with the crop became both more frequent and also more forceful. By all accounts, I should have cum already, but my pleasure core felt like it was floating above my body just watching me strike my pussy over and over again. My submission to Kim and Janice was so complete that even though I had permission to cum, I knew they were enjoying watching me crop myself and that overrode my carnal desires. Each strike was greeted with the sloppy wet sounds of my labia wrapping around the edge of the crop, an involuntary squeezing of my legs together and a deep throaty moan. But quickly my legs spread apart again without my conscious effort.

Later as I reviewed the video, I would see that I had beaten my pussy raw. But in the moment I didn't care. I was on a different emotional plane of existence. I'd forgotten I had an audience. My world was entirely the pleasure flowing through my body as each self inflicted strike of pain drove me deeper and deeper into subspace. At some point, I heard the words, "Cum now whore!" and I did. It wasn't gentle. As deep into my submission as I was, I almost didn't feel my own massive climax. Again, reviewing the video would let me understand just how much of a sub slut I had become. My body was wracked by a series of convulsions as if I was having a seizure. I suppose in a way I was. My thighs were locked together around the crop and my body rocked from side to side. The command to cum was given simultaneously by my five weekend Mistresses and they applauded while I was rolling on the floor. I should have been embarrassed. But watching the video I felt nothing but pride in how I'd served Kim and Janice. I was sure Alexis, Christine and Megan were jealous that I didn't belong to them beyond the next 46 (or so) hours.

I lay splayed on the floor for an indeterminate amount of time. It could have been 15 minutes, half an hour or two hours. When I did recover enough to get up, Megan had Janice over her lap and was spanking her. Kim, Alexis and Christine were sitting at the table. Kim told me she had originally had more plans for me the first night, but she thought it would be better to postpone them until tomorrow. I was a little disappointed, but as always she was right. I needed more time to recover emotionally.