Dee's Punishment

Here is another story about Dee, my online submissive. Dee failed me and needs to get punished. It's difficult to properly punish a slut that loves everything that I make her do. Yes, Dee is a real person. She has been my online slut for about a year now. While the punishment has not actually happened yet, it is being planned. I went ahead and wrote this as I see it happening. It's sort of a guide for Dee so she sees how I envision the evening happening. The parts about her past escapades are true.

All persons are over the age of 18. Sorry, but I can not truthfully state that all persons are fictional and don't resemble actual people. They are real and resemble exactly who they are. Well, Tom might not. He is a real person, but I have no idea what he looks like, as I have never met him as far as I know. All I do know is Dee's opinion of him. That is real.

Dee's Punishment:

I hated my brother-in-law. I absolutely despised him. Ever since my deceased husband first introduced me to his family, he has been trying to get into my panties. He's a slimeball, and he made me sick. He's seriously the last person on earth that I would willingly have sex with. Even then, I would probably have to be drunk off my ass to do it.

[DING DONG]

Fuck! That's the doorbell. He's here.

"Slut! Get the door. It's for you." Miss H called out.

OK. So, you are probably wondering why I'm about to greet my scuzzy BIL wearing only a collar and 6-inch heels. Believe me, it isn't by choice. Well, OK, I chose to do things that got me into this situation, and I agreed (well, that's too strong of a word) to put myself in this position. Those of you who have read about me in the first two stories my Master has written about me know about my life. I'm a slut. A closet slut, mind you, but still a slut. I'm in the closet because of my position. I am a wealthy CEO who runs her own business. If my employees or clients ever found out the truth, I would be ruined. Also, if my family (mainly my mother) ever found out, I would be disowned. It's actually a secret fantasy of mine to have my employees accidentally discover my secret life and turn me into the office whore.

So, what about my Master and Miss H? I have an online Master. I call him Sir. He gives me tasks to complete. Being humiliated and degraded really turns me on. The more degrading, the hornier I get. I've done some really degrading things, and they haven't all been with men and women. Let's just say that doing it doggie style is more literal to me than it is to most other people. I've been a bitch -- literally. These tasks usually involve me doing very degrading things, and most often end up with me being the center of a gang bang. Take last week, for example. Sir had me go to an adult shop and offer myself to the employees and all the customers. I wore one of my high-end business suits. The first thing I did was take a pair of scissors and shred my $2,000 skirt suit. I then got on my knees and began sucking the guys off. From there, Sir had them bind my arms behind my back and make me airtight. Sir had them apply Henna tattoos on me. On one ass cheek I got the 'Queen of Spades' symbol. On the other ass cheek, I had stick figures fucking doggie style. On my right tit, there is a cock with a pair of lips around it, on the other tit is the word SLUT. Just above my cunt are the words CUM RECEPTICLE, and I now have a tramp stamp that says CUM SLUT DEE. At one point, he had the manager whisper in my ear and tell me to scream out that I was thirsty and needed someone to piss in my mouth so I could drink it. That worked too well. I ended up drinking about a gallon of pee over the next hour. In the end, I ended up fucking about 25 guys until they couldn't go anymore. I had to buy the sluttiest outfit in the store to drive home. By that time, I was completely covered with cum, and was not allowed to clean off until I got home.

That's actually how I got into this predicament. Sir was busy messaging the store manager and directing the action. He didn't cum while I was being gang banged. I thought that I had failed him, because I was really wanting him to cum as I was being slutty for him. I felt bad. He said that it wasn't my fault, that he was too busy directing things, but I still felt that I had failed. I insisted that I be punished for that. Stupid me. Sir can be very clever and evil in his punishments. He knows that I don't like pain, so he never does that. Sure, a spanking from Miss H happens occasionally, but he prefers making me do things that I really don't want to do. I was actually shocked at what he came up with.

I opened the door, and Tom stood there smirking. As ordered by Sir, I had written Tom a note and handed it to him. He stood in the doorway as he read it. I was terrified that one of my neighbors would walk by and see me standing in the doorway naked. He chuckled as he was reading.

Tom,

I am really desperate for your cock. I can't tell you how much I need you to fuck me in all three holes. Please let me give my body to you for the evening. I want to suck your beautiful cock and swallow every drop of your magnificent cum. Then, I need you to fill my unworthy cunt. Make me cum several times on your cock, so I will remember for a long time to come that it is truly magnificent. Last, I need you to fuck my ass. I need your cum filling my ass, then you need to plug my ass, so I don't lose a drop of your gift. I will keep it inside me all night as a reminder that I am blessed by your marvelous seed inside my unworthy body. After you have fucked my ass, I will bathe your magnificent cock with my mouth and tongue to cleanse my filth off of your god-like body. Please allow my offering of my unworthy body to bring you all the pleasure you deserve this night.

Slut Dee.

Cheesy, I know. The point was to humiliate me in front of Tom. Besides, he's a narcissistic asshole. He ate it up. He looked at me with a big grin on his face. I stepped aside to let him in, then led him into the livingroom where Miss H was just finishing setting up the video cameras. Yes, she was going to video my humiliation and keep it for her records. As we walked in, she turned the cameras on and began recording. Tom walked over and sat on the couch as I kneeled in front of him.

"May I offer you something to drink?" I asked.

"Yeah. Get me a beer, slut." He replied.

My cunt gave a little spasm at that humiliation, but I got up and went to the refrigerator and got him the requested beer. I don't normally have beer at my house. I don't really like it that much. I prefer a good wine. Since I knew he would be here and what kind of beer he liked, I got a 12-pack of it. He took the opportunity to grope my tits as I leaned over to hand the can to him. I was disgusted because he didn't even have enough couth to drink bottled beer, much less drink his beer from a glass. As Sir likes to say, Life is too short to drink cheap beer. Tom drank the cheapest beer there was.

"So, Slut. You're desperate for my cock, huh?" He asked.

"Yes Sir. I really need it. I've been dying all day waiting for you to fuck me with your wonderful cock." God, how it degraded me to say that to him.

"Well, you have to earn it then. Take my shoes and socks off and lick my feet clean. Make sure you suck each of my toes really well. My shoes and socks have been on all day, and they could use a good cleaning." He ordered.

Holy Shit! This was going to be humiliating. As soon as I pulled his shoes off, I could smell the sweat coming off his feet. Still, I knew that I would have to go through with this. After I laid his socks on the floor beside his shoes, I lifted one foot up and began to lick the top of his foot. It tasted horrible. Odd how that horrid taste added to my feelings of degradation. I could feel my juices beginning to trickle down my thighs. I also began to feel myself slipping into subspace. That's the place in my brain where my natural submissiveness comes out. I go into full on slut slave mode and will do just about anything I am ordered to do. It's gotten me into trouble a few times. That's why I need a strong Mistress and Master with me to keep me out of trouble.

The more I licked his foot, the farther I fell. The humiliation was beginning to lead me farther down the rabbit hole. I began to lick the sole of his foot. I licked until I could no longer taste the nastiness. Then I began with his little toe. I put it in my mouth and began sucking on it. I acted like it was a little cock and pretended to give it a blowjob. One after another, I sucked each toe on his foot until all the taste was gone. Then, I repeated the entire process on his other foot.

Once I finished bathing his feet with my mouth, I sat back on my heels and spoke.

"Please, Sir. I really need to suck your cock. I need to feel it in my unworthy mouth and worship it until you cum. Please, let me taste your cum and then swallow it for you."

"Hmmmm. Maybe. I admit that you did an acceptable job on my feet, but I have one more task for you to do to prove to me that you really deserve it first." He stood up. "Take off my pants and underwear." He said as he began unbuttoning his shirt.

I unbuckled his belt, then undid the button and unzipped his pants. I slid his pants and underwear off together. As he was stepping out of his pants, his 4-inch dick (Sorry, I simply can't call anything that small a cock without busting up laughing) was bobbing up and down in front of me. I had a fleeting thought wondering how the fuck I would ever even feel that little thing in my cunt. My mouth? Sure. My ass? Yeah. My cunt? Doubtful. Not after all the gang bangs Sir and Miss H have had me do. Seriously, after that night last month where I took on seven black guys -- the smallest cock in the group was still over twice the size of Tom's dick. That's not even mentioning Miss H's strap-on that's nine inches long and a full two inches in diameter. She fucked me for over two hours with that monster last night. And, let's not forget all the dildos Sir and Miss H have me using while I humiliate myself in front of delivery people, repairmen, door dash deliveries, random strangers, etc.

He sat back down, then pulled his legs up to his chest. "OK, slut. Now prove to me just how bad you need it. Lick my ass. Make sure that you stick your tongue up inside my asshole too."

DIS. GUSS. TING. That echoed from a small part of my brain that had not fully gone away. The bigger part that had gone over to slut mode dove in. With my nose pressed up against his small testicles, I pushed my tongue out and began circling his starfish. I swiped all around his ass, licking and sucking everything up. I made sure to drool a bunch of saliva all around, then loudly sucked it back up.

"Oh God, Sir. I love licking your ass. Thank you for allowing me this pleasure, Sir." I said to him, then continued my oral assault. (Yes, that was one of the degrading things that Sir had ordered me to say to him if I had to lick his ass.)

I continued to lick and kiss his asshole. I stiffened my tongue as much as possible, and I began to push it against his shit hole. Eventually, I managed to get it inside. I thrust it in and out, then began wiggling it around inside. Occasionally, I would pull back to tell him how much I was enjoying the privilege of kissing his ass. Finally, he told me that I had done well enough to earn the privilege of sucking his cock.

He lowered his feet back to the floor, and I moved forward to take his dick in my mouth. That little thing never even reached my throat, but I had to pretend to gag on it. I seriously don't know how I managed not to crack up laughing, but I did. I slathered it with saliva and brought my tongue into the game to sipe around his dick as I was bobbing up and down on it. I took it all the way down and pretended that I couldn't breathe. I kept my eyes on his eyes the whole time. I'm a slut, so I've had lots of practice in giving blowjobs. I'm a fantastic cock sucker. Maybe if you ask nicely, Sir or Miss H will order me to suck your cock and I can prove it to you.

So, here I am, sucking my despised BIL's dick. I pulled off and began licking up and down his shaft, then I took his balls in my mouth and sucked on them for a bit. I took his dick back in my mouth and continued sucking on it. A few times, I took it all in, then stuck out my tongue and licked his balls. Soon enough, I felt his dick begin to swell. I took his balls in my hand and began massaging them. When he came, he blasted a small load of bitter tasting semen inside my mouth. I had pulled back so just the head was in and let his spending coat my tongue. I let it fill my mouth, and when he was finished, I pulled off and opened my mouth to show it to him. Then I closed my mouth and made a show of swallowing all of it. Miss H made sure to get everything on video. Even my mouth full of cum and swallowing.

As he finished his beer, I was using my mouth to get him hard again. Honestly, I was wondering if he would even be able to go three times. With my manipulations, I did manage to get him up after about 20-minutes. This time, it was going to go in my cunt.

"You know, I think that you should do all the work this time. Last time I fucked you, I had to do all the work, since you were locked in that pillory." Yes, he fucked me at the Halloween party Miss H took me to. Sir wrote about that and posted it as Dee's Halloween Party Debauchery. So, what Tom wanted was for me to climb onto his lap, guide his dick into my cunt, then ride him until he orgasmed. Making me fuck him, rather than simply letting him fuck me increased my degradation.

I climber on top and sank down on his dick. I was so loose that I barely felt it. Still, I went slow and made lots of noises about how he was stretching me out and that it was almost too big for me. At least this way I could grind my clit on his pelvis and bring myself to an orgasm or two. I just had to be careful and not bounce up too high and have him slip out. As I began slowly grinding on him, I noticed Miss H slipping something into Tom's hands. I didn't catch what it was, but I found out very quickly. Before I realized it, Tom was attaching nipple clamps to my tits. I'm not much of a fan of pain, but nipple clamps are a bit different. Bolts of electricity shot straight from my nipples to my cunt. My arousal jumped four levels instantly. I began grinding harder and bouncing up and down more as well. He, of course began playing with my tits. He's a guy. What guy is going to pass up playing with a set of D-cup tits that are bouncing right in his face? I didn't even have to fake it. The combination of my grinding, the nipple clamps, and the humiliation of being made to fuck this man that I despised all worked to send me over the edge. My hips began bucking automatically as I orgasmed on his dick. I guess the spasming of my cunt as it contracted during my orgasm was enough to take him over the edge as well.

OK, so my punishment was two-thirds done. I just had to get him up for the third round. Naturally, a cum coated cock doesn't bother me. After recovering from my orgasm, I pulled myself off of Tom, knelt down, and began to suck and lick his dick clean. The taste of my juices made the bitter taste of his cum on his dick more tolerable. Yes, I happen to like the taste of pussy. I'm an equal opportunity lover. I go down on Miss H all the time. I can't even begin to count the women that my deceased husband (Who was my first Master), Sir, and Miss H have had me go down on. I also have standing orders to clean all the toys that are used during parties and tasks with my mouth before washing them.

It took about 45-minutes to get him hard again. Finally, he was ready. I got the jar of lube off the end table and applied it generously to my ass. I then spread more lube on Tom's dick. Yes, I admit that I spent more time than necessary giving him a hand-job. I hope Miss H and Sir don't realize what I was doing. Finally, it was time. It wasn't that I was avoiding getting fucked in my ass, I actually enjoy anal sex. No, the issue wasn't getting fucked in the ass, it was the person doing it. At least he would be behind me, and I could pretend it was someone else -- or so I thought.

"I want you on the couch, face up, and with your knees pulled up. Lay with your ass just off the edge of the couch so your ass is exposed. I want to look in your eyes as I fuck your ass." Tom ordered.

Shit! I was expecting that I would be on my knees with my face on the floor so he could do me from behind. Now, I would be forced to look directly into his face. There would be no escaping the fact that it was him fucking me. My body betrayed me again as it got more aroused by the increased humiliation. As per the note I had given him when he first got here, Tom set one of my bigger anal plugs on the floor beside him as he knelt down into position.

Tom is anything but a caring lover. Besides that, he had been anticipating this since I called him and invited him over for this. I again thanked the gods that he has such a small dick. With absolutely no fanfare, he simply shoved his dick into my back door. Yes, there was a slight amount of pain, but that was far from the biggest thing I'd had up there. At least I could feel it more than when he had it in my cunt. It only took a moment for my ass to adjust to him and pleasure to overcome the pain. My humiliation at being forced to let this despicable man fuck my ass was ramping up my arousal. Added to that, I was talking really dirty to him. I made exaggerated noises, telling him how great it felt and how good he was fucking me. He took advantage of my position and began playing with my still clamped tits.

I looked over and saw Miss H typing on my phone. She held it up and snapped a picture of me being analized. Tom's face was away from the camera, so only my face was visible. Miss H was giving Sir a play-by-play of my degradation. The thought of Sir being witness (OK, only through words, not video) of my humiliation caused an orgasm to break through me.

"Oh God! Yessssss! Fuck my ass. Treat me like the depraved slut I am!" I cried out.

I guess the contractions of my ass clamping down on his dick pushed him over the edge. I felt the spurts of his cum as he unloaded what little sperm he had left in his balls inside me. Once he finished ejaculating in my ass, he picked up the plug, pulled out, and quickly jammed the plug inside me. The plug was about 7-inches long and a little thicker than his dick. I was just coming down from my orgasm, and it was pretty well lubed up. The plug slipped in rather easily, but there was still a bit of pain as I had to stretch out for the increased thickness.

He flopped down onto the floor to recover. I pulled myself off the couch and positioned myself between his legs. Bending down, I took his dick in my mouth again and began sucking it clean. Thankfully, it only took a couple of minutes, and he was too worn out to get another erection. I don't think he would have been able to get it up for several more hours anyway.

He rested for another 15-minutes, then got up and began to get dressed. I walked him to the door, then outside. My house is somewhat secluded, but I do have neighbors that walk along the street occasionally. Miss H ordered me to walk him to his car anyway. It's not the first time I've been out in front of my house naked. I'm pretty sure that a couple of my neighbors have seen me naked at least once. As he was getting into his car, I handed him the 'Thank You' card I got for him. Inside, it thanked him for a wonderful time and hopes of doing it again. Yes, that was written per orders from Sir. I waited for him to drive off before strolling back into the house.

"Sir said you did well. We are both pleased, and your punishment is complete. Go clean up, then you can come back in here and service me. I got kind of hot watching that, and I need you to get me off a few times." Miss H announced as I walked through the door. I was all smiles as I walked to the shower.