Becoming CD Mistress Raven's Slut

"Let's see what else I have for my sissy bitch," Ms. Raven said to herself. I could hear her rustling through a bag on the floor and then she gave another evil sounding giggle, "Perfect. These will do just fine."

A few seconds later, I felt a sharp pain on the head of my cock as she clipped what I assumed was a clothes pin to it. "Ahhhhhh," I gasped into the gag.

"That's one. I bet you can handle at least twelve," she laughed. She then clipped another one to my cock head. "Ahhhhhh," I gasped and squirmed, which elicited an immediate slap across my face harder than the previous two.

"You will take your punishment like the good sissy bitch that you are. Do not squirm unless I tell you to squirm. And I will never tell you to squirm. Got it bitch?" Mistress Raven said severely. I nodded vigorously to make sure she knew I understood. I did not want to get slapped like that again.

"And just to teach you a lesson, the number is now 15 pins instead of 12. You deserve that don't you?" I nodded just as vigorously. "Good. I'm glad my sissy bitch agrees."

She proceeded to place six clips around the head of my circumcised cock taking her time between each so that the pain lingered and grew with each clip. I felt like passing out with each new clip she added. She then started pulling up the skin on my shaft and adding clips to the shaft. My cock was so hard from being turned on and being bound that it was extremely sensitive and every clip brought a new level of pain. I was breathing extremely heavy at this point, sweating profusely and was so into subspace I probably couldn't have told anyone my name at that point.

"There. That is fifteen," she said as she added the ninth clip to my shaft. "We're half way done." I couldn't help but think, "what the fuck do you mean half-way, that's all fifteen." Then she added, "I'm very into balance, I like my art balanced. And so I need to put the same number of clips on your balls too." And with that, I entered a whole new realm of pain as she took her time applying fifteen clothes pins all over scrotum. The last two were particularly sensitive when she clipped them to the base on my sack right next to my taint. I couldn't bear it any longer and screamed into the gag, which of course drew an immediate slap to my face. "Shut up, bitch. We are in a nice resort. You can't disturb the other guests. If you have to scream, scream on the inside!" And she started laughing hysterically.

She then started to move her hand along the pins attached to my cock and balls causing a level of pain that is hard to describe. I started whimpering after less than a minute. "Do you want mistress to stop?" I nodded. "Do you want mistress to take the pins off?" I nodded again. "Will you pay the price?" I nodded again.

What I had forgotten from my prior experience is that the pain of taking the pins off is way worse than the pain of putting them on. And she took her time. She would take one off, then move her hand over the remaining pins, which was excruciating. Then take another off, so that the process took what seemed like an eternity. By the time she was done, I had tears in my eyes. I was broken and just whimpering.

She leaned down and whispered very tenderly in my ear, "You ok, baby?" I nodded. "Good. You forgot to ask the price again, baby. You want to know what this one cost you?" I nodded.

She very tenderly whispered in my ear, "I was going to fuck you with a rubber. But watching you writhe in pain and seeing your sexy body quiver has me so turned on that I have decided that I simply must have that virgin ass of yours raw. And you just agreed to that didn't you, my sweet, sweet bitch? You want me to fuck you like that, you want to feel my hot, uncovered, raw cock in your ass don't you?"

I nodded my agreement. That was exactly what I wanted at that moment.

"Good boy," she said. And the way she said it made me feel so good. I immediately wanted her to say it again. I wanted to earn her praise.

"Yes, I'm definitely going to fuck you bare. And once I breed you and cum in your ass then I will own you. You'll be my sissy bitch forever after that. You want that don't you?" she whispered softly in my ear.

I shamefully nodded my head in agreement recognizing my total submission to Mistress Raven.

She then untied the cord from around my cock and balls. "Let's let them get a little circulation. I might even let you use them later if you are a good little bitch for me." She also took the gag out of my mouth, but she left the blindfold on. "Roll over and get on all fours, ass up," she ordered.

I tried to comply but with my arms tied behind my back the best I could manage was rolling over and kind of holding myself up with my forehead on the bed. She laughed at my predicament. "I guess we can untie you for a little while," she said as she untied my arms and undid the belt she had put around my chest.

"Did you douche before you came here?" she asked.

"Yes mistress. I used the water bottles in my room."

"You better be clean. If you get any shit on me, I will lose it and beat the hell out of you. Understood?"

"Yes, Mistress Raven."

I could hear her rummaging through the bag on the floor. I then felt her applying lube to my ass and assumed she was about to fuck me. Instead, she inserted a butt plug that slid in with no problem and stayed there. "I need to ready you for my cock. I guarantee I'm bigger than anything you are used to having in there. So that will loosen you up just enough. But after all those drinks at the bar, I have to piss. So go kneel in the bathtub like a good little toilet bitch."

Of course, I couldn't see a damn thing with the blindfold on so she had to help me to the bathroom and into the tub. "Kneel ... face me ... open your mouth as wide as you can." I did as she instructed. "If you waste so much as a drop of my glorious piss, you will regret it. Do you believe me?"

"Yes Mistress Raven."

"Do you promise not to waste any of my pee?"

"I promise."

"You know that I'm about to give you a gift, right?"

"Yes mistress. Thank you. I won't waste it."

"We'll see about that ... Open wide."

And with that she let out a torrent of piss straight into my mouth. I did my best to swallow and keep up, but there was just way too much. She then started squirting it on my chest, my cock and back to my face where I opened wide and tried my best to get it into my mouth. When she finally finished I felt her gently tapping the tip of her cock on my nose, shaking off the last drops.

"You wasted some my precious bitch."

"I'm sorry mistress. I tried my best."

"Well, you still have to be punished. Take off the blindfold. Shower and get back out here and lie face down on the bed. You have three minutes."

I immediately complied. When I walked out of the bathroom, the bedroom was completely dark. I had trouble making my way to the bed in the unfamiliar room. But finally I did and I laid down on my stomach as I had been told.

"Put your arms behind your back." I did and they were immediately tied again.

I then heard her moving behind me and positioning herself off to the side of me. Then I heard the whoosh of the belt moving through the air before I felt it and heard it slap on my ass. I buried my head in the bed to stifle my cry of agony. I immediately started panting again and felt the sweat again start to form on my body. "Please, no more of that Mistress."

"Shut up and accept your punishment." With that I heard the swoosh and the stinging pain and the slap of the belt on my ass. Then after a few moments a third. She waited an agonizing amount of time and delivered the fourth blow to my ass that literally had me crying into the bed. Then after a few more moments, another harsh swat across my buttocks that I thought might make me black out.

"Will you ever waste my pee again, slut?"

"No mistress," I cried.

She then gently caressed my bruised buttocks with her hand. "Good boy, you took that beating well." Again, hearing her say "good boy" made me feel proud.

"I think you earned a reward." She untied my arms and told me to kneel. She turned on a lamp, so that there was a little light in the room and she walked over to me and stood looking down at me. She had removed her skirt. She was standing there in the leather bra, thigh high boots, and a black, silk thong that was straining to contain her cock.

"Am I your Mistress?"

"Yes."

"Do you want to suck your mistress's cock?"

"Yes, Mistress Raven. I want to suck your cock."

"Will you worship it?"

"Yes, mistress. I will worship your cock."

With that, Mistress Raven pulled down her panties and revealed her magnificent cock. It was already semi-erect and hanging about seven inches. It was not circumcised. Her cock was very thick at the base and narrowed as it went to the head. It looked like a missile. I was mesmerized by it. I reached up, took it gently in my right hand at the base and lifted it to my lips. I kissed the tip, first with just my lips and then with my tongue. I then opened my mouth and gently started sucking on the head as I slowly started moving my tongue around the head.

"Mmmmm. Good boy," Mistress Raven moaned. "Take more."

I opened my mouth wider, curled my lips over my teeth and sucked more of her rapidly stiffening cock into my mouth. Mistress Raven grabbed the back of my head and forced the rest of her cock into my mouth and held it there with my nose against her cleanly shaved pubic mound. I gagged as she forced it down my throat and I could feel her cock hardening in my mouth. As it grew it went further into my throat and eventually cut off my air supply. After a few seconds I pushed back off of her cock and gasped for air.

"Good boy. You're going to be good at this. Now put it back," Mistress commanded.

I did as she told me. I gently slid my mouth over her cock until it was once again down my throat and I could not breath. I held it there for as long as I could until I had to breath and again pushed back and gasped and gagged for air. This time a long trail of saliva connected my mouth to her cock, which was now fully erect, easily nine inches long, thick and pointing straight at me.

"Again," Mistress commanded. And again I slid my mouth down her cock and again took her past my gag reflex and into my throat and held her cock there. But this time Mistress forcefully grabbed the back of my head and held me there. "Mistress decides when you breath, right sissy bitch?" I could only nod with her cock deep in my throat. But I couldn't breathe. My eyes started to water. I started to gag and mistress took mercy and moved my head back. I gasped for air and there were now tears and saliva dripping down my face. "Awww. What a beautiful, little cock sucker you are turning into," Mistress said.

"Again," she said and we repeated the exercise. When at last she let me breathe again, I was a mess with tears and saliva all over my face.

"Now. Give me head like a good little sissy," she commanded. "Suck me good baby."

I again took her dick into my mouth and started sucking hard on the head. Mistress slapped me. "No, the head of my cock is very sensitive. So be very gentle with the head. Take it all into your mouth. Then slowly move your head up and down and be careful with the head. Understand?" she instructed.

"Yes mistress," I answered as I began following her instruction. I took her cock into my mouth and slowly started bobbing my head. Gently in and out. I used my tongue on the underside of the shaft as her cock slipped in and out of my mouth. It would sometimes trigger my gag reflex when it hit the back of my throat, which she seemed to enjoy. "That's right, gag on my cock, you slut." But for the most part I was able to keep a steady rhythm sliding her cock in and out of my mouth.

"Mmmmm. You're a natural cocksucker. Keep it up, baby. You're liking this too, I can tell. Look at your little cock."

I looked down and saw that my cock was at full attention. She called it little, but it's not. It's a nice six inches and decent thickness. I never had any girls complain. And right now it was leaking pre-cum like crazy. "Get that pre-cum and rub it on your lips," Mistress ordered. I did as she commanded and took my pre-cum on my finger and rubbed it on my lips.

"Look, there's more already. Eat it, little sissy bitch," Mistress commanded.

I did as she told me and caught more of my pre-cum on two fingers and put them in my mouth. "Good boy, does that taste good?" she asked.

"Yes, mistress."

"Mine will taste better. So get back to work, cocksucker."

"Yes, mistress," I replied as I resumed sucking her cock. I continued the slow, steady pace on her cock that Mistress enjoyed. But I started humming as well. "Mmmm. Perfect. You're such a good cocksucker. Good boy, keeping going like that," Mistress said.

Her encouragement was all I needed and I kept at it for several more minutes. Still gagging on occasion, but really getting into it. I was doing my best to make her cum.

"Get up. Get on the bed in doggy position," Mistress Raven suddenly ordered.

I was disappointed to take her cock out of my mouth. I was worshipping it and I wanted to continue. But I did as she commanded.

She then pulled the butt plug out of my ass and showed it to me. "Look what you've been keeping in your ass," she said. It was a black butt plug shaped like a cone with a handle of sorts at the fat end of the cone. It was about two inches in diameter at the base and I was surprised how easily it had slipped into my ass and stayed there.

"Lucky for you, it's nice and clean. If any of your disgusting shit was on it, I would've made you lick it off," Mistress warned.

She then began to apply lube to my ass and to her cock. "I love fucking virgin ass. I'm going to enjoy this. But so are you, my little bitch. Put your head down so your ass sticks up more," she ordered.

I lowered my head so that it was against the mattress and immediately felt the tip of her cock probing my asshole. Standing at the edge of the bed in the high heeled boots, she was at the perfect height to take my ass and she gently pushed her cock in. At first, it just felt uncomfortable. But as she started to push more and more of her cock into my ass it started to hurt. I couldn't help myself and cried out, "Awwww. Mistresss. Awwww."

"Shut up, bitch. Take my dick and shut up," with that she jammed her cock balls deep in my ass.

I couldn't help but to again cry out in pain as it seriously hurt my ass. She then slapped my ass with some kind of rubber paddle. "I said shut up bitch!" While keeping her cock in my ass to the hilt, she started smacking my ass hard with the paddle five more times. I was in tears by the time she delivered the last blow.

"I'm sorry mistress, I'm sorry," I literally cried.

But an interesting thing had happened. My ass cheek was stinging from the pain of the paddling, but my ass wasn't hurting any more. Mistress gently caressed my ass where she had swatted it and just kept her cock in my ass, not moving. "You need to learn how to be a good sissy bitch. My job is to teach you. You want to be a good cock whore for Mistress, don't you?"

"Yes mistress."

"Yes Mistress, what?"

"Yes, Mistress, I want to be a good cock whore."

"Good boy. Now, you're going to feel what it is like to get fucked real good."

With that she started gently fucking my ass. She started with small, slow strokes at first and let me adjust to having her cock in my ass. After about a minute or two of that, she started to fuck me more vigorously. She started pulling her cock almost all the way out and slammed it back inside of me. She started a rhythm and I could feel our bodies both starting to fall into that rhythm and started smacking together. Smack, smack, smack her body started tapping mine and I started moving my hips to meet her thrusts. I could also feel her balls slapping against my balls. Then she started talking dirty to me.

"Take that cock bitch."

"You like my cock in your ass, baby."

She paused and pulled her dick all the way out of my ass and looked at it. "Oh my god, you're gaping. I'm going to take a picture so that you can see what a fucking whore you are. Your ass is begging for my cock right now."

After she took a picture on her phone, she showed it to me. Sure enough, my asshole was wide open. I was actually a little worried that it might not go back to normal. But I don't think Mistress cared because she threw the phone on the bed and immediately started fucking my ass again. Now she fucked me without mercy. She just plowed her cock in my ass and kept humping me. She was using my ass now and I was loving it. My cock was hard and leaking pre-cum all over the bed.

She pulled her cock out and ordered me to roll over onto my back. "Slide to the edge of the bed and pull your legs back against your chest, bitch." I did like she ordered.

She put some fresh lube on the tip of her cock and on my ass and then slid her cock all the way in. It felt good before. But this position was even better. Her cock was hitting my prostate gland perfectly and it felt amazing. Her raw, well-lubed cock was sliding in and out of my ass so smooth, it felt amazing. I didn't want her to ever stop.

Mistress saw that my cock was leaking pre-cum. She caught it on two fingers and then stuck those fingers in my mouth. "Suck it, bitch. Eat your own cum," she laughed.

She then started seriously pounding my ass. She would draw her cock back so that just the head was still in my ass and then pound it in. "That's good, baby. You take Mistress's cock so good." And she kept fucking me relentlessly.

She then put some lube on her hand and started jerking me off as she pounded my ass. "You better not cum without asking permission first, bitch."

"Yes Mistress," I groaned. It felt so fucking good with her pounding my ass. I was in complete bliss. And I could feel my orgasm building rapidly.

"Mistress, I'm going to cum! Mistress, can I cum, please, please?" I begged.

"Not yet, bitch," she responded, yet she continued to stroke my cock even faster and pound my ass even harder.

"Mistress, please, please I'm going to cum!!" I yelled.

"Don't you dare cum bitch. If you do, it will cost you!" and she squeezed my cock even tighter and pumped it even harder.

There was no way I could hold back any longer and started shooting rope after rope of cum. It was an amazing orgasm. The first shot went over my shoulder and part of it landed on my chin. The next few shots were all over my chest and Mistress's hand as she continued to stroke my dick and pump all of my cum out.

She then started almost growling. "Ohhhh, you motherfucker!! You are going to pay for thaaaaaaattttttt." As she said that I felt her cock start to spasm in my ass and I felt the hot rush of her cum start to fill my ass. "Ohhh, fuck, I'm filling your ass right now bitch!!" Mistress screamed as her orgasm overtook her. It felt like her orgasm would never end. She continued to erratically pound my ass as I could feel her cock continue to spasm inside of me. I couldn't imagine how much cum she must be shooting because it felt like she was filling me completely with her cum. Finally, she stopped and collapsed on me but making sure that her cock stayed in my ass.

After a few moments she caught her breath, she said, "That's it, bitch. My seed is in you now. Your ass is mine. Whenever I want it. However I want it. I own you bitch."

I was still basking in the afterglow of my own orgasm. I could not remember ever having another orgasm as powerful. This was by far the most intense sexual experience of my life. "Yes Mistress, my ass is yours, I'm yours," was all I could say in response.

"Good boy," she replied with a devilish, beautiful smile. My heart jumped at her words. She then used her hand to scoop up most of my cum off my chest and fed it to me. She told me to lick her fingers and get it all.