Becoming CD Mistress Raven's Slut Ch. 02

Author's Note: I took some inspiration for this next chapter from some of the comments, both public and private, that I had to the first chapter. In doing so, I've written about things (e.g. forced cross-dressing) that I've never personally experienced. Most of my writing is based on things that I've experienced and that I think I can relate. So, if I've missed something or not captured it right, please let me know. As always, any and all comments are appreciated and I hope you enjoy.

For anyone who didn't read the first chapter, this is about a straight guy getting used and abused by a cross-dressing dominatrix. So if that's not your thing, you probably should just stop reading here. You don't have to have read the first chapter to understand this one, but it would help regarding character development, etc.

*****

After I came back from my swim, Reuben, Kevin and I lounged on the beach for a while. Kevin was on his phone looking for something for us to do the next day and suggested we try the resort's zip-line course. He said it would take most of the morning. I was in, but Reuben said he couldn't because he was "otherwise committed" tomorrow morning.

I was pretty sure I knew what he meant—he, or rather Mistress Raven, was seeing the client that flew him down here and put him up at this resort. But I was curious how much Kevin knew. So when Reuben was off exploring the beach, I took the opportunity to find out.

"Hey, do you know what Reuben meant by 'otherwise occupied'," I asked.

"Yeah, but I probably shouldn't tell you," Kevin replied.

"Why not?" I responded. "We're in Mexico. Whatever is said here stays here."

"Alright. But you cannot let on that you know. So, it turns out that Best Buy is not Reuben's best source of income. In fact, he's making so much money in this other gig that he told me he's going to quit that job when he gets back to LA," Kevin said.

"No shit? What? Is he running drugs or some shit?" I queried as if I didn't know.

"No, but probably almost as dangerous. He's working as an escort. Specifically, he cross-dresses as a dominatrix and sees guys he meets through the Internet. He says he is making a boatload of money letting 'straight' guys suck his dick!" Kevin said making air quotes with his fingers when he said the word "straight."

"Damn. I would never have guessed that. How did he get started doing that and how much money is he making?" I asked.

"As long as I've known him he's been really into women's fashion and enjoyed doing drag shows. He does them a couple of times a month. He's really good and super-convincing." "That's fucking true," I thought to myself.

"So after one show a few months ago, this guy comes up to him, tells him he's married but has a thing for men dressed in drag and offers Reuben $300 if Reuben will come out to his car and let this guy give him a blow job. So Reuben did it and then this guy kept coming back to almost every show. Well, the dude must have posted something on the Internet or somehow told some other guys because there started to be other guys showing up asking for the same thing. So Reuben is making like $500 to $1000 after these shows letting these married guys suck his dick. He said he enjoyed it and really liked the power that he felt he had over these guys. So he created this online persona and now he has so many regular clients he's going to quit his regular job and just do that," Kevin explained.

"Holy. Fucking. Shit. I cannot believe that," I lied, "Absolutely incredible."

"Here's the best part. I've gone online and read reviews about him. He is apparently excellent at this. And he tells me he has taken the anal virginity of almost a dozen guys, just in the last few months! So he is actually getting paid to abuse guys, let them suck his cock, and then he gives them their first ass-fucking!! How incredible is that!" Kevin exclaimed.

"Pretty incredible," I replied, but Kevin didn't know how I really meant that.

"I mean, you won't believe this," Kevin continued. "Reuben told me he has a client that is in to financial domination. Basically, this dude gets off giving his money to Reuben. Dude had some kind of blackmail fantasy. So Reuben takes pictures of this guy with his dick in the guy's mouth, cum all over the dude's face or whatever, and then texts the pic to the guy a week later and the guy then Venmos him $1000. Every fucking month!"

"Damn. That is fucked up. Dude must be loaded," I replied.

"Yeah, Reuben said he's an executive with one of the big media companies. Reuben said the guy told him he masturbates right after he sends the money to Reuben. Weird as fuck, right!" Kevin exclaimed shaking his head. I could only shake my head, thinking that I couldn't really judge the guy given how kinky things got for me the night before.

"And it is perfect for him," Kevin continued. "As long as I've known Reuben, he is the kind of person that uses people. If you can't do something for him, he really doesn't even bother with you. So it's like he has fallen into the perfect spot where his penchant for using people fits exactly what they want. It's like that old '80's Eurythmics song, 'Some people want to abuse and some people want to be abused' right?"

"I guess so, wow, I didn't expect to hear all this today," I again lied.

"So whatever you do, be careful with Reuben. I know you guys barely know each other, but he will still try to use you. Like how he got your dumb ass to pay for this cabana and our mimosas all morning! Cheers!" he said lifting a glass of the mimosas I paid for and toasting me.

"Cheers, asshole," I replied, lifting my own glass to his. "If he's like that, why do you hang out with him?"

"I know what he's about, so I watch myself," he answered. "He and I have some mutual friends and we have some mutual interests, so it works."

"Interests?" I asked curious about what that meant.

"It's a gay thing ... I would tell you but then you'd have to suck my dick," he laughed off my question. Kevin and I were totally cool with our different sexualities and him joking about being gay was nothing new for us. But I also knew him well enough to know that he used humor to deflect stuff he didn't want to talk about, so I let it go.

***

That night the three of us were having dinner together. We were all pretty tired having been on the beach most of the day and Reuben was spending time texting people. As soon as he put his phone down on the table my phone binged telling me I had a new text. I picked it up and saw it was from Reuben. The text read, "Your Mistress requires your service again tonight. Be at her room at 10:30. Prepare yourself well - in/out. And have some champagne sent to her room beforehand. Just reply, Yes Mistress to confirm. If you don't, you will never see her again."

Even though I was really tired, I immediately replied, "Yes Mistress" and hit send. A few seconds later, Reuben's phone pinged with a new text alert. He didn't even bother looking at it. He knew what it was.

Reuben excused himself right around 9:00 saying he was tired and wanted to pack some stuff early since we were leaving the next day. Not long thereafter, I used the same excuse to call it a night. I went up to my room and called room service and ordered a bottle of champagne for Reuben's room. I then again used the water bottles as enemas, groomed my pubic hair with a set of clippers I'd brought thinking I might meet an available lady, showered and prepared to see Mistress Raven.

At 10:30 exactly, I knocked on the door to Reuben's suite. The door opened immediately and there stood Mistress Raven. She had the same long flowing black hair and leather bra as last night. But she was wearing red fishnet stockings and a red shiny thong. Her cock more than filled the front of the thong and was noticeably looking to burst out.

"Enter slave. Strip. Then kneel before your Mistress."

I immediately obeyed. She sat in a chair in the living area of the suite near a small table. The table had a wig, lipstick and other items that I couldn't really tell what they were from my position on the floor in front of her. "Be a dear and open that bottle of champagne and pour me a glass, slave," she commanded.

"Yes mistress," I got up and did as she ordered and returned to kneeling in front of her.

She began to gently stroke my cock and balls with her right foot as she began speaking to me, "Last night was fun. I enjoyed myself and I enjoyed you being my slave. Did you enjoy it?"

"Yes mistress," I replied keeping my head bowed and watching my cock grow as she continued to gently rub it with her foot.

"Of course, last night we did all the kinds of things that you told Reuben at the bar that you liked doing. Did you notice that?" she asked sipping on her champagne.

"Yes mistress. Thank you, mistress."

"But I expect more from my slaves. I expect you to get off doing things you don't enjoy. I expect you to get off from your pure submission to me, whatever it is that I require of you. Do you understand that?"

"Yes mistress," I replied looking down at my cock which was now at full attention.

"Is that the kind of slave you want to be—one that gets off serving me no matter what I desire?"

"Yes mistress."

"Very good. You are going to be a very good slave," she said as her left foot now joined her right and started jacking me off with her feet.

"You told Reuben that you did not have a foot fetish. You said you thought feet were disgusting. Didn't you?" she asked.

"Yes mistress."

"And you said that you did not enjoy it at all when that dominatrix you saw made you dress like a woman. Right?" she asked.

"Yes mistress. I just wasn't into that particular kink," I replied honestly.

"But we are not here to find out what you are into are we?" she asked.

"No mistress. I am here to serve you." I replied.

"Good boy," she said as she wiped a drop of pre-cum off the tip of my dick with the big toe on her right foot and held it out to me. "Suck it!"

I took her toes into my mouth and began to suck. "Good. Worship my foot. Kiss it, lick it, adore it like the little slut we both know you are."

I did as she asked. I was honest when I had told Reuben that I thought feet were disgusting and I had to hold back a gag as I did it. But I continued to kiss each toe and then suck each one into my mouth one at a time. I then kissed the underside of her foot and then licked her from heel to toe. I then did the same on the top of her foot.

"Good. Now this one," she commanded as she held her left foot in my face. I repeated the same thing on her left foot, licking her toes, sole and top of her foot. Again, I had to hold back a gag because I really don't like feet.

She saw my discomfort and laughed as she then put both of her feet in my face and began to rub them around. I could feel the soft fabric of her fishnet stockings rubbing all over my face. "Does my slave want more," she laughed.

"If it pleases my mistress," I replied.

"Good answer, slave! It does please me so lick them more, especially sucking my toes. I really like that." So I did as she commanded and licked the bottom of her stocking-covered feet and continued sucking her toes. Despite how disgusting I found this act, I couldn't help but notice that my cock stayed rock hard the entire time.

Mistress noticed that too and commented, "I think maybe you like feet more than you think. Or maybe you just are a very submissive little bitch."

She pulled her feet away and said, "We're going to find out how submissive. Stand up." I stood and she took a piece of cord from the table and began wrapping it around my balls separating them from my body. She pulled by balls down with her left hand stretching my scrotum so the she could keep wrapping the cord around my balls with her right hand, which was really stretching my sack. She tied it off. She then got a rubber cock ring and slid it down my cock and secured it at the base. My already hard cock became instantly fully engorged and hard enough to cut steel. "That will do just fine," she said giving my cockhead a hard flick from her fingers.

My scrotum ached she had stretched it so much. She began to run her finger nails across my ball sack. As stretched as they were, it felt like she was dragging them across gravel. She then started flicking them hard and repeatedly to the point that my knees buckled and I crumbled before her.

"Stand. Up. Bitch," she ordered.

I did and she handed me a riding crop. "Swat the tip of your dick and you better do it hard or you will regret it." So I tried to hit my cockhead with the crop hard, but there is an instinct of self-preservation that makes that pretty hard to do.

Mistress was not impressed with my effort. "No!," she exclaimed ripping the riding crop from my hand, "Like this!" And with that she swatted the tip of my dick so hard that I immediately crumbled to the floor again in pain. I started whimpering, my heart started pounding and I started sweating.

"Stand up and do it right this time," she commanded as she handed me the crop.

This time I closed my eyes and swatted my dick as hard as I could. I saw stars and had to drop to a knee.

"Good! Do it again bitch." I stood and did it again with the same result of me having to take a knee.

"Stand and do it one more time you fucking little pain slut," she ordered. I again complied with the same result of me on my knees now gasping for air.

"Good boy," she said. "Step 1, you did something you did not like for me. Step 2, you hurt yourself for me. But Step 3 is going to be the best of all. Follow me," she said.

I followed her into the bedroom and saw that there were nylons, panties and a teddy on the bed. "Get dressed like the sissy slut you are," she commanded.

"Mistress, if a may, I'm really not into ..." I started to complain when she slapped me harder than she had ever slapped me before. It was more like an open-handed punch to my jaw than a slap.

"Shut up. You will dress like the sissy you are or you will leave. Are you my sissy slave or are you not?" she glared at me.

"Yes mistress. I am." I replied softly.

"You are what?"

"I am your sissy slave."

"Then dress like it bitch," she said harshly as she turned to leave the room. As she closed the door she said, "You have five minutes."

I seriously considered leaving at that point. My hands weren't tied, I could just undo the cord around my balls and get out of here. But I was overcome by my submissive desires. I wanted to please Mistress Raven. So I walked to the bed and picked up the pink, frilly panties and pulled them on. They were soft, satin-like and had lacy fringes around the top. I was embarrassed by the realization that the soft material actually felt good on my engorged cock which I was barely able to stuff into the panties. The panties bulged grotesquely with my cock and balls in the bound condition they were in.

I then put on the thigh-high nylons. They were a light shade of pink to match the panties and also had a lacy pattern at the top. They had a pronounced seam that ran up the back. I felt my legs after I had put them on. Again, I felt embarrassed that I liked the feel of the soft material against my legs.

I then slipped the lacy pink teddy over my head. It was mostly shear and see through. My humiliation deepened when I realized there was a bra on the bed as well. I took the teddy off and struggled with the bra. With all my practice snapping bras off girls, I still couldn't figure out how to get to snap into place. So I slipped my arms out of the straps and turned it around so I could snap it in the front. I then shifted it to the back and slipped my arms through the straps. I was so embarrassed to be doing this I could feel my face flushed. I then put the lacy teddy back on and was about to go out the door when my humiliation deepened even more. There, next to the door, was a pair of pink, high heel shoes. I hoped they were Reubens and would be too small for me. But they weren't - Reuben had obviously brought these down for his client. They slid on easily and actually were about my size; but I had trouble standing steady in the five-inch heels.

I awkwardly walked out of the bedroom and looked at Mistress Raven. Her face lit up with delight. "Oh my god, you are a sexy, sissy slut. I bet there are lots of guys at this resort that would love to fuck you. Hell, I bet I can find someone that will pay me to fuck you!" she exclaimed.

I lowered my head in embarrassment as a pang of fear went through me. I really, really hoped she was just teasing me.

She walked up to me and gently rubbed my stiff cock through the soft material of the panties. "Mmmmm, still nice and hard for me. Good. Does that feel good, baby?" she asked.

"Yes mistress," I responded.

"You like the feel of these panties, don't you sissy?" she teased.

I hesitated, but finally confessed, "Yes mistress."

She rubbed my ass gently and felt the panties on my ass. She then ran her hand on the back of my thighs. "And you like the way these nylons feel too, don't you? Admit it, you are a sissy."

My face flushed with embarrassment and humiliation. "Yes mistress," I softly admitted.

"Yes mistress, what?"

"Yes mistress, I'm a sissy," I said, my humiliation complete or at least so I thought.

"Come here and kneel before me," she commanded as she again sat at the chair near the tale. I awkwardly walked to her and kneeled where I had earlier with her sitting in front of me. She then took a tube of lipstick and applied it to my lips. "That's a cute color for you," she said to herself. She continued to apply make-up to my cheeks, eyelids and eye brows. "Oh damn, you are going to be a sexy bitch."

I felt absolutely, completely and totally humiliated by what she was doing to me. I have never had a fantasy about being cross-dressed and had felt bored by the whole thing the one time the dominatrix I saw before did it. Now I was just embarrassed and broken that I was powerless to stop this.

She then put the wig on me. "Perfect! Let's let you see the new you! Stand up."

I stood and she positioned me in the room in front of a mirror. I was shocked at what I saw. Looking back at me was the most humiliating thing I've ever seen. I looked ridiculous. I had platinum blond hair in a bob to my shoulders. Lipstick and make-up covering my face, but with my two-days of beard growth it would obviously fool no one.

Mistress was laughing hysterically at my reaction. "Look what a submissive, sissy bitch you are. Even though you hate it, you dress like a woman for me. You are mine bitch. I own you. I know that now and so do you!" she exclaimed with true excitement in her voice.

Sadly, I knew she was right. If I would do this for her, what wouldn't I do. Standing there, I began to wonder where that line was or if there even was one. I humiliated myself for her and it turned me on beyond measure.

"Look bitch!" she said pointing at my crotch, "See, you are completely mine!" My humiliation only deepened when I saw that pre-cum had soaked through the panties leaving an obvious wet spot.

"My glass is empty bitch," she said simply. I walked clumsily in the high heels to get the champagne bottle from the ice bucket and refill her glass. "The ice is melting. Here," she said handing me an empty ice bucket. "Go get more ice."

"But ... Mistress ... I can't ..." I started to say in a soft whisper gesturing to how I was dressed.

"Oh, you're right silly. I can't send my sissy bitch out like that. There are kids at this resort after all, you'd frighten them," she said much to my relief.

"Here, put this on," she said handing me a small thin robe. It was kimono that when I put it on barely covered my ass. The tops of the thigh highs were still completely visible. "You can go like that."