Becoming CD Mistress Raven's Slut

**Author's Note: This story is very kinky. It has a lot of BDSM and is about a straight guy having an encounter with a cross-dressing dominatrix. It's definitely not for everyone. Hell, it might not be for anyone. But hopefully a couple of you will enjoy it. All comments are welcomed. VJ**

*****

Kevin looked at me and just shook his head. "You gotta snap out of this, bro. Your marriage is over, but your life isn't."

He was right. But it didn't feel like it. It had been six months since my divorce and all I wanted to do was stay in bed. Just crawl into a hole and fall asleep.

"I got an idea," he said. "Why don't you come to Mexico with me and Reuben. It'll be fun."

"No, I can't do that. It would be weird. I'd be a third wheel," I replied. A word of explanation is in order. Kevin has been my best friend since junior high. We had been through a lot together, including our first year of college when Kevin came out as gay. He and I were roommates at the time and I was there for him through it all. Now, fifteen years later, my marriage was over and Kevin had been through a series of relationships. I assumed that Reuben was the latest. Reuben was younger, Latin, and that tended to be Kevin's type.

"No, it's not like that," Kevin responded. "He and I are just friends. He's real cool to hang out with but he's into some, well ... he's just not my type. Let's leave it at that. We're not even sharing a room at the resort. He got a suite, but I'm in a regular room. He's actually going a couple days earlier than I am to meet someone there."

We kept talking for another thirty minutes and Kevin finally convinced me. Part of it was that he was right, Reuben was pretty cool. He was flamboyant and very effeminate, always wearing tight clothes and kind of swishing his hips when he walked. He had a high, almost feminine voice too. But his flamboyant personality was also hilarious. He was always the life of the party and things were never boring when he was around. So I went online and booked my flight and a room at the resort. It was surprisingly cheap, probably because of all the violence from the drug cartels in the news lately.

Ten days later, the three of us were in an amazing swimming pool at a resort in Mexico. We were all drinking rum drinks and ogling the beautiful bodies all around. They were of course trying to identify any gay guys and were commenting on everyone's bodies. I was only commenting on the women that seemed to be there without a male companion. We were all feeling good and having a good time.

Standing in the pool was the first time I realized how small Reuben really was. He was only about 5 feet 6 inches and was very thin. But he did have good muscle tone and a very flat stomach. It was also the first time I realized that he must shave his entire body or something. Dude had no hair anywhere other than his head it seemed—arms, legs, chest were all completely smooth. I wondered if it was a gay thing, but Kevin had typical body air, so I really wasn't sure.

When the pool scene had started to die down, Reuben suggested we liven things up with a game of "never have I ever." It's the game where someone throws out a statement of something they have never done, and if anyone else has done that, you drink. It was pretty easy for me, as the only straight guy, to make them drink, "never have I ever sucked a dick" and they both drank. "Never have I ever had a dick in my ass" and they both drank. But Reuben got me with this one, "Never have I ever paid someone to dominate me." When I drank, both Kevin and Reuben started laughing hysterically.

"You have to tell us about that," Reuben demanded.

"Seriously? I didn't even know about this one and I know everything about you," Kevin chimed in.

I told them I'd rather not get into it but Reuben wasn't having any of that. "I simply must insist that you divulge your kinkiness. Inquiring minds want to know, honey," he said.

So I told them that I had seen a pro dominatrix several times during a rocky point in my marriage. I wasn't getting any sex at home and wanted some excitement. I had always been somewhat submissive sexually and so I gave it shot. I saw her probably 10 times over about a year. They both started asking me for details, but I just played it all off hoping the subject would just go away. And I was thankful when Kevin, obviously sensing my discomfort, moved the conversation in a different direction. "Oh my god, Reuben, look at that guy in the speedo." Reuben must have agreed with Kevin's assessment because he made a bee line for the guy without saying anything else to either of us.

But later that night, Reuben brought the subject up again. Kevin wasn't feeling well after dinner and went to his room early. So Reuben and I were alone at the bar when he started asking me about it again. I had had enough to drink at that point that I didn't really mind talking about it with him.

"Did she tie you up?" he asked.

"Every time. She would tie a cord around my cock and balls, almost like a cock ring at the beginning of every session. Then she would usually chain me to a standing cross or she'd strap me to a table. It was hot."

"Damn. Did she do CBT on you? Please tell me she tortured your package."

"Yeah she did, in all kinds of ways. She would slap my package. Kick it. She used an electric wand on me a couple times. She even put sounds in me and fucked my cock hole one session. I can't lie, I was into it."

"Oh fuck, that is so hot," Reuben responded. "So, what else? Did you do golden showers or did you try pegging?" he asked. "You can tell me honey, whatever is said in Mexico stays in Mexico."

I laughed, "Yeah, we did all that. I can't believe I'm telling you this. But she pissed all over me at the end of every session as I jerked myself off in her bathtub. I actually got to where I liked the taste of her piss. And she fucked me good. She had this purple dildo that she would strap on. She used it on me three or four times. She would make me suck it to get it wet. Then she would lube my ass and fuck me, sometimes all soft and sensual, but sometimes she would just plow me. She would tell me I was her bitch and she would bang my ass hard."

"Oh my god, you kinky motherfucker, you are almost turning me on with this shit. Please do tell me more. So you liked it?" Reuben asked.

"Yeah. It was hot. She pushed me way past anything I thought I would do. I came one time just from her fucking me with the dildo. She wasn't even touching my cock."

"Damn! You nasty slut! So what happened. Why did you stop going to her?" Reuben asked.

"That's around the time I lost my job, which was really the beginning of the end of my marriage. I couldn't afford it. By the time I found a new job, I guess I had moved on and never really thought about it anymore. But now that I'm thinking about it, maybe I should call her again."

"How did you find her?" Reuben asked.

We ordered more drinks.

"Internet. Where else?" I pulled out my smart phone and went to the web page where I had found her. I scrolled around a bit but couldn't find her. "I guess she's moved on," I told Reuben.

He asked to see my phone and started scrolling through the website. Living in Los Angeles, there seems to be an infinite supply of people into kinky stuff, so there were a lot too choose from. He asked me about some of the dominas advertising there and whether I was interested in them or if they were my type. Some were, some weren't. We'd look at the pictures and comment on them. Finally, Reuben zeroed in on what he thought was my type, "You like the smaller, petit, brunettes, especially the ones that are into pegging and golden showers, right?"

I was started to get a little uncomfortable because he pretty much nailed it. "Uh, I don't know, maybe something like that, but it's hard to say," I responded trying to deflect this conversation.

Then he looked at me mischievously and said, "Hmmm. How about this one?"

The add said, "CD Mistress Raven - Come be my sissy bitch." I opened the ad and started scrolling down. Mistress Raven advertised that she was an "aggressive CD dom." She said she was a 28-year old Latina and her measurements were 5'6", 130 pounds, with "9 glorious uncut inches." Her favorite activities included "CBT, bondage, golden showers, turning straight men." She had several photos of herself in a sexy leather miniskirt, fishnet stockings, and high heels. There were no pics of her face, but she looked pretty passable and I have to admit I felt my cock stir a little looking at the pics. There was a pic of her ass in a red thong and it looked like a nice round woman's ass, you'd never know from the pic that it was a CD. And then there was a close-up pic of her crotch in red satin panties and her obviously erect cock was impressive as it poked out the side. I let myself linger on that pic for a little too long and I felt my cock twitch in my pants as I stared at it.

"So what do you think of that one?" Reuben asked with a glimmer in his eye.

"I have to admit. She's attractive. But I don't know if I could do that. That would be pretty kinky."

Reuben laughed, "It would be the same as your other dom. Just this one doesn't have to strap on anything." And he laughed again.

"Maybe so. But I don't think that she's really for me."

He glanced down at my crotch and made sure I caught his glance. "Are you sure?"

I was embarrassed that my cock had actually gotten hard enough for him to notice.

"I don't know. Maybe, I guess," was the best response I could come up with.

We ordered more drinks.

"Well, at least you referred to her as 'she'," Reuben said. "At least that shows you're sensitive to transgender issues and not some sasquatch savage."

"C'mon, I'm Kevin's best friend," I replied. "What would you expect?"

"I just appreciate that. You're a sweet guy. I have to admit, sweet, submissive, straight guys kind of do it for me," Reuben said with a glimmer in his eye and a slight laugh that was actually kind of awkward.

Reuben then picked my phone back up and started looking at the Mistress Raven ad again. "What if she was here at this resort right now and you could see her in Mexico and no one would know a thing. Would you do it? C'mon be honest."

"I don't think so, I guess I might. But no, I don't think I would."

"I bet you would. I'll bet you $100 you would. I can see it in your eye and your pants." He glanced down at my crotch again to let me know that he knew my cock was still bulging in my shorts.

"OK. It's a bet Reuben. If you see her here, let me know and we'll find out," I said laughing.

"This is my favorite pic of her," Reuben said as he held my phone so I could see it. On it was a picture of Ms. Raven standing with her arms out away from her body stretching a whip. That's when I noticed she had a bright blue and green butterfly tattoo on the inside of her arm. And then I literally gasped when I saw that same tattoo on the arm holding my iPhone.

"Holy shit!! You have that same tattoo! Is that ... holy shit that's you?!?!" I exclaimed.

"Hush. You'll cause a scene," Reuben laughed. "I can't believe your cock just got hard looking at my pics. That's sexy. I'm honored. And I'm turned on too." He looked down toward his crotch, inviting me to do the same. I couldn't help but look to see if he was being honest. He obviously was. There was clearly the outline of a massive cock visible through the thin fabric of his shorts and it went part way down his thigh.

He caught my glance, looked at me and smiled. "Impressive. Right?"

"Ugh. Yeah, it is," was the best response I could stammer as I blushed and pounded down the rest of my drink in self-defense.

I ordered another round of drinks.

"So, do you want to meet her?" Reuben asked with a big smile on his face.

"Ugh, well, ugh, did you actually bring your all of your ugh, ugh, Mistress Raven stuff?" I asked sheepishly.

"Yes, silly," Reuben responded. "I saw one of my regular clients earlier. That's why I came down early. You don't think I paid for the suite at this place on my Best Buy salary did you? He paid for it and my flight too. He's here with his family and I will see him one more time before we leave. So back to my question, do you want to meet her?"

I have to admit, I had no idea what to say. I was turned on by the pics and the ad. But I was not attracted to Reuben. It was a very, very weird situation. "I admit I'm turned on and tempted, but I'm going to pass. Mistress Raven is hot. If I'm going to be honest with myself, if she was a total stranger, I would probably do it. But I know she's you and sorry Reuben, I'm not attracted to you."

"Suit yourself, baby. She could do wonders for a sweet bottom boy like you. She can put a man into subspace like no other. But I get it. I will tell you that when I turn into her, I feel like a completely different person. So it might not be as weird as you think."

"Um, I have to admit my head is spinning."

Reuben laughed, "One of your heads is spinning, the other one is still trying to get out of those shorts you're wearing! Ms. Raven is the illusion that causes confusion honey! Straight boys pay to be with her all the time. But I get that this is different because we know each other. So no worries. Forget I even mentioned it."

We tried to talk about other stuff for a while, but the conversation kept coming back to BDSM. What I liked, what Mistress Raven liked (Reuben would always refer to his alter ego in the third person). The whole conversation was sexual and I was getting incredibly horny. So around 10:30 I decided to call it a night; I knew I needed to get out of there. I asked for the check and when it arrived, Reuben put his hand on my thigh and said, "Be a dear and pick that up."

"Sure no problem," I said.

"Thank you, baby." And Reuben's hand grazed my still semi-hard cock as he lifted it off my thigh. I realized how that whole check / thigh thing that just happened was a dominant move by Reuben and I had totally submitted.

My head was still spinning as we left the bar and made our way across the lobby to the elevators. Once we were in the elevator, Reuben made a sudden move and kind of pinned me against the wall of the elevator. I'm six foot two, so I tower over him, but he was surprisingly quick and strong. "I'm going to go to my room and dress. If you want to meet the Mistress, knock on my door at midnight exactly. If you don't do it tonight, you will never meet her. So go to your room and decide." With that, the door opened on my floor and I got out. "Don't miss this chance. You will regret it. Mistress will make you feel like no other," Reuben whispered as I walked out of the elevator.

I went to my room and flopped on the bed. What the fuck? This situation was crazy. My cock was still hard. I was a little drunk. I could not get the images of Mistress Raven out of my head. And I was also thinking about Reuben's cock. What the hell? Why am I thinking about a dude's cock? I took out my phone and looked at Mistress Raven's pics again and decided I would do it.

I used one of the bottles of water in my room as an enema and then repeated with a second bottle. I took a shower. I paced the room back and forth and just kept thinking that I should just go to bed instead. So I brushed my teeth. Went to bed. I laid there staring at the ceiling for five minutes. Got up. Got dressed. And went to the elevator. I looked at my watch - 11:56 pm. I was standing in front of Reuben's door at 11:59. Am I really going to do this? My heart was pounding so hard that I could hear it in my head, like it was going to beat right out of my chest. My watch turned to 12:00. No, I can't do this and I turned and started to walk away. I took three steps. Stopped. Turned around and knocked on the door.

The door opened immediately. There stood Mistress Raven. She was obviously wearing a wig, but her hair long black hair looked natural. Her makeup was dark and severe. Deep red lipstick, dark colors on her eye makeup and cheeks. But to my amazement, it didn't really seem like Reuben standing there. It was instead Mistress Raven and she was wearing a black leather bra, the black miniskirt from the ad, with black, thigh-high patent leather boots with thigh high fishnet stockings under. "Enter, my sissy bitch. Get naked right here. Then go into the bedroom and kneel. Now!"

I did exactly as she told me.

She smirked. "Oh you are a little submissive bitch, aren't you?"

"Yes mistress."

"Yes what?"

"Yes. I'm a submissive bitch."

"Well. We'll find out. Put your hands behind your back."

I complied and she got a cord of some kind and tied my hands very tightly together behind me. She then took a couple of belts that she had tied together and put those around me to secure my arms to my chest. She then put a blindfold of some kind on me.

"Open your mouth, slut," she commanded. I complied and she stuffed something into my mouth and then secured it there with a strap around my head.

"That's a rubber cock, my little slut. But don't worry. I'm sure you will earn a chance to suck the real thing if you're a good boy. Now, stand up!"

I did as she said and stood up, which wasn't easy with my hands tied behind my back. As soon as I was standing she shoved me hard and made me fall backwards onto the bed.

"Now, let's see what you're packing here," she said as she started to gently caress my cock and balls. "Mmmm," she moaned, "It's kind of small, but Mistress approves." She used both hands and gently continued to massage my cock and balls using both hands. I was hard as a rock, when she slapped my cock with an open hand so hard I cried out into the gag, "urggggghhhh, ohhhhhh" was all that could be heard.

"Did I give you permission to get hard?"

I could only shake my head no. She then slapped my cock again. "Uggghh" and I began to start breathing heavily.

"Clearly I need to somehow restrain this thing because it has a mind of its own," she said. I then felt her wrapping a cord of some kind around my scrotum separating my balls from my body. After winding the cord around my balls three times, I then felt her tying it around the base of my cock. It was very tight and uncomfortable. But the effect was to make my erection even harder than it already was and my balls felt like they were being pinched off my body.

"You have really big balls, did you know that?" I nodded that I did because other girls had told me that before.

"I bet they are super sensitive, let's see." She then started gently tapping my balls with her open hand. At first it felt kind of good, but as she kept tapping it started to hurt and I started getting the dull ache in my stomach like someone had punched me in the balls. She was relentless with the pounding and I started to whimper.

"Ahhh, does that hurt my sissy bitch? Does it?" I could only whimper "uh, hmm" into the gag in my mouth. "Want mistress to stop?" I nodded. "OK, but it will cost you? Will you pay the price?" she asked as she kept tapping on my balls. I felt like I was going to throw up and I wanted to roll over to protect my nut sack, but I couldn't. I nodded and whimpered "uh hmmm, uh hmmm." She stopped.

She giggled kind of an evil laugh. "You stupid bitch. You didn't ask the price. Do you want to know what it is? ... It's your ass, I'm going to fuck your ass." And with that she slapped my face so hard I thought I saw stars. "Dumb fucking whore that you are, didn't even ask the price!" And she slapped me on the other cheek, even harder. "Are you a dumb fucking sissy whore?" I nodded and whimpered into the gag, "uh hmmm." "Well, at least you have some self-awareness," she said as she laughed again.

I was seriously going into subspace now. My mind was turning to mush. My heart was pounding. I started sweating even though the temperature in the room was cool.