My Best Friend My Nemesis Pt. 16

Stacey was empathetic, and promised to fix things when Ivan arrived, but I was scared shitless. He had treated me very roughly when I sucked his cock, upon arriving at the Wynn Palace. God knows what he expected from me, if we were alone for eight hours in a motel.

Ivan arrived about forty minutes later, and the two of us loaded the luggage into the huge trunk of the limousine. Adrian gave us strict instructions on how to load the cases. He wanted his loaded first, so we put the six Aluminum cases in the deepest part of the trunk. Sara's six Glacier Blue suitcases went in next, in a particular order, to ensure that the two cases that contained her lingerie, swimsuits, short skirts, Halloween costumes and accessories, were easily accessible. Adrian also decreed that my pink Barbie suitcase rode up front next to Ivan, with my "SLUT" collar resting on top. This presented a visual reminder of my availability to him, should he desire to enjoy me in the hotel suite.

I was so scared I thought I would piss myself, and Adrian was having the time of his life. Ivan was a very scary dude. He had served multiple prison sentences and, according to Svetlana, had intimidated several hardened inmates to become his bitches, while doing his time. I had already decided that Ivan wouldn't need to use any threat of violence towards me. I would just submit to his desires, to avoid getting my ass kicked. I went to find Ivan, to let him know that I was going to be totally compliant on the journey home. Better to get that out of the way up front, I reasoned.

By the time I found Ivan, Stacey had beaten me to it. She had him cornered in my en-suite bathroom, and was working her magic on him. I walked in on them, and Ivan glared at me for my interruption. Stacey was whispering in Ivan's ear, and rubbing his cock through his pants. He had a visible erection, and was breathing hard. I apologized to Ivan, and asked him if we could talk before we got on the road.

"Pink," Ivan growled.

I wasn't sure I had heard him correctly. His first language is Russian, and his English is heavily accented.

"Excuse me?" I said, with as much deference as I could muster.

"Pink," he repeated. "If you came to ask me what color lipgloss I want you to wear for our drive home, it is pink."

Stacey giggled at Ivan's bluntness, and said, "someone is going to to get a little road head on the way home!"

She never stopped teasing Ivan through the fabric of his pants, and he glared at me again, as if to tell me to beat it. I didn't want to have this conversation in front of Stacey anyway. I was about to let Ivan know he didn't need to use any violence, or even the threat of violence, to make me submit to him. I would do whatever he wanted, on the trip home. That humiliating admission needed to stay between Ivan and I, so I turned and left the room.

I heard Stacey say, "So if I sweeten the deal with Svetlana, are we good?" as I left the room.

Ivan found me a few minutes later, and told me to follow him into the media room of the large suite. As he closed the heavy door with a thud, I remembered reading on the Wynn Palace website, that the Garden Villa had a sound-proof media room. My heart sank, as I realized that Ivan had chosen this room to hide my screams, as he was going to either kick my ass, or fuck it.

Fear is a very powerful motivator, and I submitted to him immediately. I sank to my knees and started letting Ivan know my intent.

"Please Ivan," I begged. "You don't have to hurt me to get what you want. I will do whatever you say."

I reached my hand out tentatively to stroke his erection, but it had disappeared. Adrian hadn't allowed me to remove the pink fingernail polish, and my slender hands looked very feminine, as I toyed with Ivan's non-existent erection.

"Stacey sucked me off," Ivan informed me. "She sucked my cock a few minutes ago, to save your ass. She promised me a two-girl blowjob from her and Svetlana, if I leave you alone. You and I need to come up with a plan. Adrian is expecting me to ass-fuck you during our layover in Barstow. He wants some photos of me dominating you. We need to make it appear realistic. Stacey already knows all about it."

I was relieved to find out that Ivan wasn't planning on beating, or fucking, my ass in the media room. The rest of the plan needed a little work, but Ivan said we would work it out.

"Don't worry Chris," he assured me. "As long as Stacey and Svetlana honor our agreement, your tight little ass is safe."

Stacey and Svetlana had let me down so many times, that I did have some concerns about them honoring the deal. However, that was out of my control, so I tried to put it out of my mind.

Once the limousine was ready to go, Ivan took Adrian and the three girls to the private jet terminal at Las Vegas Airport. Adrian wanted me feminized for my trip home with Ivan, and told the girls to make it happen. Luckily, Stacey had a good friend, that was a beautician in the MAC store, in the Miracle Mile Shops. She agreed to come to the Garden Villa, and do my makeup.

It was embarrassing when she first arrived, but she told me she did makeup for a lot of Vegas drag queens, and not to be shy. A few minutes later, she had transformed me into a passable female, through the skillful application of makeup, hair and nails. She spritzed me several times with Svetlana's perfume, and I smelled like a girl.

My Agent Provocateur lingerie was delivered to the Villa, by the hotel dry-cleaning staff, along with my freshly laundered sucky pillow. The young woman held the silky garment up for my inspection, and told me that all of the yellow stains had been successfully removed. The beautician smiled at that remark, and I wondered if everybody in Vegas knew that Adrian had pissed on me.

Once both women left, I put on my lingerie, my butt-form crotchless panties, stockings, garter belt, and my peek-toe Louboutin pumps. My breasts were fuller, and I noticed that someone had sewn larger breast forms, into the top of the camisole. I used the silk-lined leather gaff to hide my male genitalia, and once again I was passable.

I put on the pink choker to hide my Adam's apple, although I fully expected Ivan to collar me with his preferred "SLUT" collar, for the photo shoot. One last look in the mirror, and I was very happy with my appearance. I stood by the front door of the Villa holding my red sucky pillow, and waited for Ivan to arrive.

Ivan entered the Villa shortly after I was ready, and did a double-take.

"Holy shit, is that you Chris?" he asked me, with desire written all over his face. "Call Stacey, and tell her the deal is off," he said menacingly. "I want a piece of your ass."

I felt sick to my stomach, as Ivan approached me, and undressed me with his eyes. He got within arm's length of me, and told me to kneel. I obeyed him immediately, dropped my sucky pillow and sank to my knees on it. I couldn't help but notice that his erection was back, and I swallowed hard.

"Relax, Chris," Ivan said, in a much softer tone. "I am fucking with you. We just need to take a couple of pictures to keep Adrian happy."

Ivan got out his phone and snapped a few pictures of me kneeling before him, on my red silk pillow. Then he stood next to me with his hand resting on my head, and took a few selfies. Next up, one of me from behind with my head in his crotch, appearing to suck his cock. Then one of us in the bathroom, with me bent over the counter, and him positioned behind me, apparently fucking my ass. I could feel his erection against my ass, and he kept sniffing me. He told me to act like I was in pain, and took a few shots of our reflection in the mirror.

Next up, was me on all fours, with him kneeling in front of my head. Again, through clever use of mirrors, Ivan made it appear as though he was face-fucking me. I could feel his cock twitching, as my face touched the front of his pants. We went outside and took a few shots, in and around the limo. He put the "SLUT" collar on me, and took a photo of me, draped across the front bench seat of the limousine, with my head in his lap. He put one hand on the steering wheel, as if to simulate that he was driving, and receiving road-head.

We took a few photos in the back of the limo. Different shots of him enjoying me in various positions, both orally and anally. Then one more of me kneeling by the limo with a chamois in my hand, appearing to have just cleaned the wheels of the car. He took great care not to show the hotel in the background, and ten minutes later we were back in the Villa, checking out his photos. We deleted most of them, but kept about twenty very realistic shots of Ivan, repeatedly enjoying my mouth and ass.

Ivan texted Svetlana, and she walked us though how to download an app, to blur our faces. Then, satisfied with our work, Ivan gave me a warning.

"You need to take a quick shower, Chris," he said in a serious tone. "I am getting aroused by your look and scent. I can't be responsible for my actions, if I am around you for much longer, dressed that way. I have a very powerful sex drive, and have always struggled to control my urges. A lot of the guys I raped in prison, were friends of mine who got in my way on the wrong day."

"I appreciate your candid warning, Ivan," I told him. "I bet I could get you to come very quickly, if you did decide to enjoy me," I joked, for reasons unbeknownst to me.

As soon as I said it, I wished I hadn't. Ivan flashed me a stone cold killer stare that sent chills down my spine. I lowered my head, and went to leave the room to take a shower.

As I left the room to go and take a shower, Housekeeping showed up, and told us it was time to check-out. I was going to ask them if I could take a quick shower, but decided against it. Adrian was a very frequent guest at the Wynn, and it was just his style to ask what I was wearing when I got into the limousine. I got into the front seat of the limo "en femme" and sat next to Ivan.

We had about a two and a half hour drive to Barstow, and we ended up talking non-stop. We had a lot of shared interests, and would have been great friends, had we met under different circumstances.

"I really don't like Adrian," Ivan told me. "I work for him because the money is good, and the work is consistent, as Adrian travels frequently. However, I hate the liberties Adrian takes with Svetlana. She is a sweet young Czech girl."

I found that a little ironic, as Ivan had come in Svetlana's mouth, just a couple of days ago. However, I took the opportunity to throw Svetlana under the bus.

"Svetlana is far from sweet. She is actually a very submissive girl," I lied. "She loves being sexually abused by men, the rougher the better. She told me that the highlight of her week, is waiting on her knees in the shower for Adrian to chug his beers, and urinate on her."

Ivan smiled at that revelation, and asked me about my relationship with Adrian. I shared a few of the indignities that Adrian had heaped on me, and Ivan seemed really interested.

"When Adrian fucked my ass," I told Ivan, "he looked at me in the mirror and proclaimed that the next time he butt-fucked me, I would have piercing blue eyes."

"Do you even have a pair of blue eye contact lenses?" Ivan asked.

"No," I told him, "but I could use Sara's if I needed to. However, the point is Adrian obviously plans to fuck my ass again, before he releases me from his service. I am dreading it. It was very uncomfortable, and I know we will have an audience."

"I butt-fucked loads of dudes in prison," Ivan said coldly. "Whenever I got a new cell mate, I would rough them up on the first night, to put the fear of God in them. The threat of serious injury was usually enough to get a guy to completely submit to me. Once they feared being permanently injured more than they feared anal sex, I could take whatever pleasure I wanted, day or night. That said, I never made one of them wear blue eye contacts," he added. "Adrian is messed up."

As we drove towards Barstow, Ivan shared some prison stories. He had fucked up lots of inmates, broken several jaws, stabbed a guy in the eye with a pencil. Turned some of his long-term cellmates into sex slaves. He was definitely not a guy to fuck with. Ivan said that he hoped that I got out from under Adrian's thumb, before too long. I told Ivan that I was considering leaving California, but it seemed like the long arm of the Russian Mafia would find me wherever I hid.

"Not in Hawaii," he responded. "You would be safe from us in Hawaii. The Russian Mafia has no presence in Hawaii. It is run by Samoan and Japanese gangsters. It is too far for us to go. We would not enjoy the protection of safety in numbers, no back up. You could live there peacefully without any threat of retaliation. Adrian is not a gangster. He only has access to our hired muscle, because he wraps our investments in with his NFL portfolio, to give us tremendous returns on our cash."

I was pleased with this news. Both the fact that I could move to Hawaii and start my life over, and knowing that Adrian was not connected in any way to the Russian Mafia. He just hired Ivan and his crew as mercenaries, when needed. The drive to Barstow went very quickly, as Ivan and I chatted amiably. When we got there, I stayed in the limo, and Ivan checked in. We were in the nicest hotel in Barstow, which isn't saying much. However, it was clean, and I relaxed in the air-conditioned suite, as Ivan brought in two of Sara's cases, and my pink Barbie case.

My ass was feeling much better, and I told Ivan I could drive the rest of the way home, if he wanted to have a drink. I guess you should never say that to a Russian, because he was delighted with that idea, and ran straight to the liquor store to get some vodka. When he returned, we closed the black-out curtains, so that you couldn't tell if it was day or night, and began the photo session.

We opened the two suitcases of Sara's that contained her costumes and lingerie. Most of Sara's clothes were too small for me, but we found that anything made out of Lycra, elastane or spandex, would stretch enough for me to wriggle into. It would be a tight fit, and obviously shorter on me than Sara, but that was the look we were going for anyway.

Ivan picked out five outfits that were made of stretch material, and handed me the first one, telling me it that was his favorite. It was the pink Playboy Bunny uniform with all the accessories, still in its dry-clean bag. It was quite small on me, and as I struggled to get it on, I was grateful for the fact that I had taken it to get it dry-cleaned. Emasculating as it was to be dressing up in fantasy costumes for Ivan's photo shoot, it would have been worse to wear that ridiculous Bunny costume, with Adrian's semen splattered all down the front of it.

I did manage to squeeze into it, but it was very tight and form-fitting, and there was no rear access for anal sex. Adrian, of course would have known this, as he had enjoyed my wife several times in this costume. Sara even referred to it as her "Blowjob Bunny" costume.

"We could take some pictures that simulate me giving you a blowjob, Ivan," I offered. "We just won't be able to go any further, due to the limitations of the access this costume provides."

"Adrian knows me too well to believe that I would stop at a blowjob," he said laughing. "If you were on your knees blowing me, wearing that, he knows I would rip a hole in the rear of that Playboy Bunny costume, and fuck your ass."

"Well, we don't need to be destroying any of Sara's costumes," I said, timidly.

We agreed that we needed a change of outfit, and Ivan seemed more than disappointed, when I removed the "Blowjob Bunny" costume.

Ivan's disappointment was very short-lived. Sara had a yellow cheerleader costume that was made of Lycra, packed in one of her suitcases. I put that on, with some matching yellow bobby socks, that had a lace ruffle around the top. I arranged my wig in pigtails, tied with a couple of yellow silk ribbons, and held the matching Pom Poms. That put the smile back on his face! Ivan snapped a few photos of me, apparently dancing a cheer routine for him. Then we went through an array of submissive poses, blurred our faces, and then forwarded the time on the clock, so that we could repeat with a different outfit.

We did this four times, advancing the clock about ninety minutes each time, so that it appeared that Ivan busted a nut four times in the eight hour rest period. We had pictures simulating me getting fucked in doggy-style, cow-girl, reverse cow-girl and on my back in the missionary position. There was photographic evidence to prove I had knelt before Ivan and sucked him off, that he had straddled my face, and that I had laid across the sectional and sucked his cock.

We took dozens of pictures, and chose the most realistic and demeaning ones to send to Adrian. According to the photos, Ivan violated me dressed as a cheerleader, a nurse, a schoolgirl and finally in an obscenely tight, hot pink, off the shoulder Lycra dress that was several inches too short for me. After forty-five minutes we had the photo session complete, and both of our faces were blurred. Ivan had consumed six vodkas, and had a very noticeable erection. I was sitting on the sectional still dressed in the pink Lycra dress.

I was going to suggest to Ivan that we just get on the road. We no longer had to wait eight hours for Ivan's rest period, as I was going to drive. Then, I realized that Adrian expected us in San Clemente after midnight. He liked to control everything, and it really wouldn't go over well if we showed up six hours early. So, even though I wasn't ecstatic about being alone in a hotel suite, dressed as an alluring female, with an increasingly inebriated Ivan, we stayed put.

Ivan stood up to pour himself another vodka, his cock straining against the fabric of his pants. As he staggered over to the kitchen, I questioned whether it was a good idea for me to be in this hotel room, with this ex-felon gangster, who was getting drunker and more aroused as the evening progressed. He poured himself a very large vodka and then sank into the recliner.

Ivan kept looking at the photos we had taken, and adjusting his crotch. He occasionally would look over at me, and mumble something in Russian. He was slurring his words, and I knew I was on the menu for Ivan tonight.

"What a fucking idiot I am," I said quietly under my breath. "What did I expect allowing him to get drunk, and parading myself around in slutty outfits for forty-five minutes? Why the hell would I simulate sex with this man in multiple different positions, and not expect him to get aroused?"

I was in deep shit now, and my mind was racing to find a way out. I had done it the last time I was in this position, in the limousine, when Ivan told Svetlana or I, to suck his cock. I miraculously got out of that situation. I needed another lucky break.

I couldn't leave the hotel room dressed as I was, "en femme". It was only 3pm, sunny outside and I had nowhere to go. There was a truck-stop a few hundred yards from the hotel, but I had no cash on me. That would put me in the same position as I was now. I would be forced to suck a trucker off, for a ride to Orange County. I assessed my options, and decIded that I would give Ivan what he wanted. Hopefully, he would pass out after he ejaculated, and would remain asleep until we needed to get on the road.

Then it hit me. The key to my freedom from a good ass-fucking, from this increasingly drunk Russian, was to make him pass out. I got up from the sectional, grabbed my sucky pillow, and walked seductively over to Ivan. He was looking at the pictures of me, and had his hand down the front of his pants. It seemed as if he had abandoned the nice guy act, and had decided that he was going to fuck my ass. I had never seen someone consume so much alcohol, in such a short period of time.