Dear Diary Ch. 03

It looked like oral favors had been traded. I watch Kim lead Cheryl into the bedroom and shut the door. I guess that meant Steven and I had the couch. I moved to give him room and pointed to the cushion. He didn't say anything. He just sat down and I reached for his belt buckle.

I felt a little jealous that another woman was servicing my Mistress in my presence. I knew she obviously was having sex at school, but since I was there I felt it was my duty to take care of her. As I pulled down Steven's pants, however, my jealousy evaporated. Steven didn't have the longest cock I'd seen. But he might have had the fattest. Suddenly I got the feeling that Cheryl should have been the one who was jealous to be sharing his cock with me. He wasn't hard yet, but he was definitely showing signs of life. I took that as a complement as I reached forward and gave him a couple firm tugs to move things along. Then I went down on him.

I fancy myself to be skilled at orally pleasing a man. But as soon as I wrapped my lips around his shaft, all I could think about was how wonderful he would feel in my pussy. Perhaps two hours of remote teasing played a part, but all I could think about was getting fucked. Steven must have sensed that too because after just a minute or two, he pulled my head back and straight out asked if I would prefer him in another hole.

"Yes I would," I said honestly, "but Mistress has me in chastity. Please let me get you off so she won't be mad."

"Show me this chastity," he said. Of course it sounded like a command. As much as I hated to leave his cock, I stood up and lifted the back of my dress.

"Standard TSA luggage lock," he said with a snicker. I then stood up and removed his pants the rest of the way. "On your knees on the couch facing away from me," he said confidently. I immediately complied.

I heard him looking for something in his pants pocket and quickly felt the lock release. As he removed the belt, he didn't seem surprised to find I was plugged.

"I was wondering why you looked so wanton at the party," he said rhetorically. I then felt him fish the Lush out of my pussy. "I can see you're ready for me," he added, although that comment was hardly necessary. I responded, "Yes sir."

As I said, he wasn't overly long, perhaps six and a half inches. But his cock was thick and easily stuffed me. I felt extra wicked just having my dress flipped up over my ass as he entered me. Whether he was worried about how long we had or whether he just cared about getting himself off and not letting me build to my own climax I don't know, but he just started pounding me. At first, his girth was an issue. I would have preferred he gave me a bit more time to properly stretch. But soon it didn't matter as his cock felt glorious. He didn't spank me, which was a bit of a surprise, instead opting to hold my hips tightly and pull me back to meet his thrusts. It was primal and my moans expressed that. Anyone in the hall would have heard me and I'm sure Mistress did too in the bedroom. In fact, that was an issue. Kim walked into the living room far too soon to put an end to Steven pummeling me.

"What the fuck are you doing, slut," she shouted. "I gave you permission to blow him. That's it."

I was too far gone to give a solid answer. I think I babbled, "He made me," or some other stupid response I knew she wouldn't believe. He asked me would have been more appropriate but the decision had been mine. Maybe if I had said no he would have fucked me anyway, but this transgression was my fault.

"Fuck off," hissed Steven. "I'm almost there."

I heard a scuffle behind me and felt his cock slide out of me. I felt very empty. I looked over my shoulder and Kim's arm was around his neck pulling him backwards. He was obviously bigger and stronger than her, but she had the right leverage to stop him. When she spoke again, she surprised me.

"You can finish, but give me a minute."

At first I figured she wanted him to finish on my face. It definitely would be in character for her to have me walk out of the house decorated with a fresh load. I looked down at Steven's cock. It was glistening with my juices but looked angry at not being able to cum. Kim retreated to the bedroom again but returned maybe ten seconds later holding a bottle with a dispenser pump. When she said, "You can finish in her ass," it didn't take a rocket scientist to know what was in the bottle.

Mistress Kim gave me a sharp spank on my right butt cheek and then unceremoniously pulled the remote plug from my rectum. Two pumps of lube, a finger to spread it around and inside of me and then a command to, "Grab your cheeks and hold them apart, whore," and I was ready. At least I was as ready as I could be when Steven took aim for my asshole.

I've learned to love anal sex through my time with my Mistresses and having worn the plug for two hours helped, but Steven's width was still an issue. It was an issue for me anyway. Again, he didn't seem to care. Once the head of his cock was home, he just pushed. I grunted but didn't let go of my ass cheeks. I wasn't going to disappoint Mistress a second time in two minutes.

I thought I'd probably be bleeding as he began to fuck me. Mistress wore longer strap-ons, but they were narrower. Thankfully he really had been close to cumming and the tightness of my ass and the overall kinky situation proved to be too much for him. With one last thrust he grabbed my hips and held me tightly against him. I suppose I should have been grateful Kim didn't order him to cum on my face as he shot what felt like a gallon of jizz deep inside of me. He held me tightly for about 30 seconds, at least half of which was spurt after spurt of cum splashing my bowels. The other half was him catching his breath before he pulled out leaving me gaping for my Mistress' enjoyment. I suppose it was my enjoyment too, although I had not cum.

"Cheryl is still on my bed," Kim told Steven. "She can clean you. I have to plug this slut back up before she leaks on my couch."

I maintained my position on my knees on the couch. I felt the plug sliding back up my ass. Of course now there was zero resistance. In fact, I hoped I would be able to hold it in. Part of me wanted her to reattach the chastity belt, especially since I now knew it was a tiny lock and I could break it if I got really desperate.

Instead, Mistress ran her fingers over my pussy. "Such a good and needy sub," she told me. "How should I punish you?"

I was pretty sure that was rhetorical. Mistress didn't need my suggestions on how to punish me. It was then Alexis, Christine, Megan and Janice walked into the room. Janice was still wearing her dress, but she looked like she had been used. Kim pulled my dress down over my ass and told me to stand up.

"Mom, take Katie to the house you rented and prepare for our arrival," she told us. We made a quick retreat from the room making a joint walk of shame through the house. I don't know if the girls played further with Cheryl or Steven. At that point, my only worry was losing control and having the plug slide out of my ass. Steven's cum was starting to leak around the edges. I needed to get out of the house as quickly as possible. We walked by Tori who was near the front door. I was petrified she would want to talk. Thankfully she just shot us a knowing glance and smiled. I took Janice's hand and rushed to the car. Once we were safely inside, I turned to her and said, "What the fuck was that?"

She smiled back much like Tori had. "Last year Alexis seduced me. I thought I was a Domme and had never had sex with a woman before. But it was amazing. I don't know how she has learned as much as she knows at so young an age, but she opened my mind to how amazing submissive sex can be. When she told me Kim had taught her, I was shocked."

"So you didn't know your daughter was a dominant?" I asked.

"Well, I'd seen signs, of course," she replied, "but it was always in the context of her boyfriends. I knew she knew I dominated her father so I figured that was where she picked it up. It was only after Alexis seduced me I found out she was bisexual."

"Um," I stammered.

"No, we've never played together, if that is what you're wondering," Janice reassured me. "Alexis told me that Megan is her submissive and Christine is Kim's. She also told me that in the context of this weekend, all four of them would be above us in the hierarchy."

"And you would still be my Mistress," I added. I mean, being submissive to four college hotties was an amazing opportunity in my mind. But I didn't want to give up serving Janice to get it.

"From what I understand," Janice continued, "Kim is in charge with Alexis, her number two. I get the sense from Alexis that she still takes orders from Kim on occasion. Megan and Christine will still answer to them, but outside of any conflicting orders, we will have to do what they say as well."

"What about you and I," I asked, sounding hopeful.

"I am still your superior," she replied allaying my fears. "But for the next two days, I'm not sure how much that means. It might be a distinction without a difference."

"I don't understand," I replied.

"We both have to do whatever the girls say," Janice told me. "Whether I will have any say in what you do, I'm not sure. Honestly, I kind of doubt it. But don't worry, when we leave on Sunday, you'll still be my sweet submissive slut. OK?"

"Yes Mistress," was the easiest reply I had today.

Janice didn't make any demands of me on the way to the AirBnB. The plug kept my mind occupied along with the thought of having five Mistresses to serve. Well, maybe four and a half. The house was a few miles out of town on a farm. An actual farm. There was a barn and several sheds and everything. It looked like the farmhouse was more profitable as an AirBnB instead of the farmer living there. I wondered if he knew what was going to happen there this weekend.

We took a quick tour of the house. Two bedrooms upstairs with queen size beds. A large country kitchen attached to a dining room, a bathroom and a living room on the main floor. We didn't find a basement. We found instructions from the owner about how to access the barn if we wanted. He didn't have any livestock, but there were his tractors and implements. He warned renters to be careful. The sheds were off limits. There was satellite TV and a bluray player in the living room, but nothing in the upstairs bedrooms. Then Janice reminded me we had better prepare for the girls arrival. I must have looked confused so she told me to "Give me your dress." She also started taking hers off. Well duh. Of course we should be naked.

Janice did take care to hang up both our dresses in the front hall closet. I wondered if I would see it again before we left on Sunday. We then knelt next to each other about four feet inside the front door. She reminded me to kneel with my knees spread apart and to cup my breasts in an offering position. I hoped the girls would arrive soon. When Janice reached over and started rubbing my pussy, I hoped they would be delayed. "We have to be sure you're nice and wet for Kimberly," she told me. I took that as permission to reach over and start rubbing her. "And you for Alexis," I replied.

I wish we had a camera recording us as we rubbed each other while our free hands played with our own nipples. It was straight out of a cheesy porn movie. But if it were a movie, we both would have cum. As it were, we were both fighting not to let that happen. Janice was the first to switch from teasing fingers to trying to get me to climax fingers. As my Domme, that is her right. But I knew she had orders not to climax as well, so I picked up the speed of the assault on her clit. I was going to try to make her cum, at least until she ordered me to stop. But Janice didn't do that. She was definitely enjoying herself. So was I. In fact, neither of us heard the girls' car pull up or noticed the door opening. We were both caught in full out making each other climax masturbation. When I saw Kim, I lost control and started cumming. The day had been too much for me to hold back. Alexis was next in the door. Looking up at her Mistress and feeling my climax on her fingers was too much for Janice as well. We were both bad, needy sluts who needed to be punished for our transgressions. But that would have to wait a bit.

"Well sluts," Kim began. "Obviously you will need to be punished for this transgression, but that can wait. We had a game prepared for you that was going to have pleasure as a reward, but I think we can modify that a bit."

I had assumed we would be playing kinky games so I wasn't upset by what Kim said. Then Alexis continued by telling Janice and I to go out to their car and bring in the luggage, toys and food. This was a little nerve racking as we both were naked, but the house was private enough that it really wasn't a problem. Each girl had a suitcase, there were three bags of groceries and one big box that was taped shut. I assumed that was the toys. The box was large enough and heavy enough to make me wonder just what they brought. It took about 15 minutes for us to bring in the items and then unpack the girls. As I expected, Kim and Christine were in one bedroom and Alexis and Megan were in the other. They had not brought much in the way of clothes, just a couple casual outfits and some lingerie. Kim and Alexis also had matching leather bustiers. My mouth watered just thinking of what they would look like wearing them. The toy box remained sealed and my mind continued to race thinking about what it contained.

It was time for the first game. It was very simple. The basic idea was Janice and I would lay on the dining room table in a 69. The first person to climax again would be punished and the sub who didn't cum, would get some kind of reward. I assumed that would be permission to orgasm, but it wasn't defined. Kim then took a quarter and told her mom to call it in the air. She said heads but it came up tails.

"Katie, you get to choose top or bottom," Mistress announced.

Usually in a 69 I was always on top, but that was because I was sucking a cock. I was also smothering the guy with my pussy trying to make myself cum. Since the object of the game was not to orgasm, I quickly picked bottom and crawled up on the table. I don't know if Janice was happy or sad about being on top. As aroused as we both were, even though we had cum 20 minutes ago, it probably didn't matter. She immediately pressed her mouth against my pussy and started giving me head. And she was good. She also was holding her pussy a few inches above my mouth meaning I couldn't easily reciprocate. It was then I realized I'd made a bad choice about being on the bottom.

All was not lost, however. I was able to reach up and grab her ass. At first I used my strength to lift my head up and get access to my objective. Once I did that, Janice lowered herself down so I could lick her with my head still on the table. I was focused 100% on making Janice cum and winning this challenge. She seemed to be doing the same as her tongue dove into my wet folds. I couldn't see the girls, but it wouldn't surprise me if we were being recorded on their phones. I found that thought exciting imagining Kim using a video of me to seduce other girls on campus.

The combination of Janice licking my pussy and my own enjoyment licking hers plus the vision of performing for four college girls was an incredible turn on. Although I was holding her ass tightly trying to keep my mouth against her pussy, Janice was squirming a lot and kept breaking contact with me. I don't think she was doing this in an effort not to cum. I think she was just as turned on as I was and her motions were involuntary. As for me, being on the bottom meant I was going nowhere and even involuntarily I couldn't defend my clit from the assault of her tongue.

Did I "lose" the challenge? I'm sure you know the answer to that without having me tell you, although I did last longer than I would have predicted. I'm pretty sure Janice was about to crash over the edge as well, but Kim ordered us both to stop after I came and Janice, hopefully with reluctance, crawled off of me. I continued to lay on the table. I was pretty spent. My heart was racing, my breathing was ragged and I needed some time to recover. Kim ordered Christine and Megan to "prepare the surprise" and they grabbed the toy box and walked out of the front door. I was curious where they were going, of course, but I didn't ask what they were doing. It wasn't my place to ask. I was here for their enjoyment, although I was glad I got my own pleasure. I had to wonder, however, if that was my last orgasm for the night. Or worse, for the weekend.

Janice asked if she could get a glass of water from the kitchen. Alexis told her yes, but reminded her not to masturbate. That probably wasn't necessary as I got the sense Janice was a good sub to Alexis and already knew the rules. But still, it was a good reminder to me that she wasn't the person I had thought she was before this weekend. In the meantime, Kim put a thick leather collar around my neck. As I was the low woman on the totem pole of the four submissives at the house, it was expected. As Janice returned, with two glasses of water, Kim snapped a leash on my collar and pointed to the floor. I immediately dropped to my knees. She also thanked her mom for bringing me a glass. "We have to make sure you stay hydrated this weekend," she told me. "Drink up. The girls should be ready for us soon." That sounded ominous, but I took the glass and quickly drank the water.

Nobody talked for about a minute. Alexis and Kim were looking at Janice and I with a predatory look. I was sure they had already planned almost every minute of the weekend. Well, maybe not the encounter with Cheryl and Steven, but then again, maybe that too. I remained kneeling on the floor while Alexis walked behind Janice and wrapped her arms around her. I admit I was jealous when Alexis started teasing Janice's nipples and then moved her hand down to finger her pussy. When she rubbed her clit, Janice moaned.

"Oh, was my baby close to cumming when Katie ate you out?" Alexis said with more than a hint of mocking in her tone. Janice didn't answer, but her moans became more forceful. It was then that Alexis proved to me she had a sadistic streak in her the same as Kim had shown to me so many times. She grabbed Janice by the back of the neck and guided her over to stand in front of me. From my position, I was faced with a view of Janice's very wet and needy pussy. Alexis then began to rub her clit again.

"My slut didn't get to cum thanks to you, Katie," she said. "Do you think I should let her cum now?"

I wanted Alexis to push Janice forward so I could get a second chance at making her orgasm. I admit I was greedy to taste her again. But I also recognized this was part of their game and the proper response was, "Whatever you decide, Mistress Alexis." She then commented to my Mistress that I had been well trained. That made me happy. Mistress Kim, however, had another plan. "Just let my mom rub her slutty pussy on my slave's face. She doesn't deserve to enjoy eating her yet.

Alexis put her left hand behind my head to hold me still while using her right hand to press Janice's butt and force her pussy against me. I opened my mouth and stuck out my tongue, but Alexis ordered Janice to move up and down, denying me the pleasure of capturing her clit between my lips. Janice seemed happy to hump my face. I knew that could make her cum, but the result was her scent was pressed over my nose and basically all over my face. I knew I would be smelling her for the next hour no matter what happened next. I also knew that would keep my arousal level high, although I doubted that would be much of a problem. The masochistic part of me figured Kim would edge me over and over as punishment for losing the contest. But was that really a punishment? I mean, I hated it when I had to masturbate every hour. But I always had a massive orgasm eventually. Maybe her plan was to edge me continually. To keep me on the cusp of cumming for hours. My mind was reeling at the possibilities. I should have just tried to relax and realize that whatever Kim had planned was going to happen and I would just have to go along. But a slut like me doesn't think that way.