The Road to Hell... Ch. 05

(Hopefully you enjoy this next chapter. Make sure you read the others, the cast of characters is getting large. In this one, we get to see more of the slutty office co-worker Diane. Also, Debbie's life gets pretty interesting pretty quickly.)

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The next day things got even better at work. Diane wore a more revealing outfit than normal. Her cleavage was again displayed but this time her skirt was also very short and flirted with revealing her ass when she walked. When I went to lunch, she hopped up from her desk and followed me to the elevator. Getting in with me she immediately came up to me and grabbed my hand. "Is that finger better?" she asked as she shoved it into her pussy. I couldn't believe how wet she was and she was clearly not wearing any panties which I imagine is what she wanted to show me. "Don't go to lunch. Just spend an hour doing this. My husband's at work and my house is close. Let me show you what I'll do that that wife of yours won't."

"Diane... " I said. I'd only planned on a quick lunch and I had a lot of work to do. My boss would eventually start thinking of me as the world's best employee but that might take awhile. "I fucked my wife in the ass last night while she ate a girl out." Okay, okay... That was a couple weeks ago but the point was there to make.

Diane just stood there and stared at me and I pulled my finger out. I gave it a suggestive lick as the elevator door opened leaving her standing there dumbfounded while I walked to my car. I planned on letting her simmer for awhile, curious as to what she'd come up with. Denying her was ramping her up and I wanted to enjoy it when she burst.

I grabbed a quick bite to eat and returned to the office. Diane was obviously not ready to take "No" for an answer. There was a folder on my chair and in it was a black and white picture of her, completely naked. She was as gorgeous as I had imagined. I quickly shredded the picture, however. I planned on getting pictures and video a lot better then a grainy black and white. But I figured this was a good chance to try to prod her a little more. I picked up the phone and dialed her extension, "Diane, can you come in here please?" 15 seconds later she was striding into my office. "Shut the door please," she closed the door with a smug look. She clearly thought she was winning. "Let me show you something," I said and opened up my Gmail account. I clicked on my starred emails and up popped a long list of emails from Kay. Many of them had very explicit headers. I picked one, however, that seemed to be innocuous, "Something for you," it said. Up popped a picture of my wife (post tattoo and bleach job). She was bent over with her hands cuffed behind her back and a dildo sticking out of both holes.

Turning back to Diane, she was standing there staring. "You see Diane. My wife tries very hard to keep me satisfied." Diane shook herself out of her daze and walked out without saying a word. I glanced through a couple other pictures of my wife before getting back to work. There was a consulting job coming up that would be a perfect chance to take things up a notch with Diane. I went down to my boss's office. "Are you still looking for someone to go with me to Miami?"

"Yeah... We've got several people in the office that can go... "

"Let's send Diane. You said you want some of the more junior people to get chances at this stuff. This should be pretty low key so it ought to be a good chance."

"That's a good idea. That'll keep the job cost down, too. I'll get it on the schedule. You're flying out tomorrow?"

"Yeah, just two nights so I'll be back Friday night if you need me." I had our secretary, Laura, make the travel plans and send Diane an email. I didn't want it coming from me because I didn't want her to know how eager I really was. I finished up my work for the day and went home. I was pretty satisfied with the work I'd done both professionally and personally that day. Diane was going to be all kinds of fun for the next two days. When I got home, Debbie's car was in the driveway. My dick got hard thinking about her and my wife going at it inside. However, when I opened the door, I was greeted by an entirely different site.

My wife was sitting on the couch getting yelled at by two girls while Debbie was crying. Kay was trying her best to stay calm but I could tell instantly that the berating had been going on for awhile and was nearing her limit. "What's going on here? Why are you screaming at my wife?" I yelled. I was pissed.

One of the girls broke off and came over to me, "Debbie got home last night and her clothes were ripped. She was a mess. We thought she'd been raped or something. When we asked her about it she said she'd been over here fucking you two!"

"So... " I said, playing dumb.

"Bullshit! Debbie wouldn't even think of that. She's the most innocent, naive person I've ever met," Debbie started sobbing again.

"See, now you've hurt her feelings," I said. "Look... what is it you're worried about?"

"We think you forced her to do it. Either you got her drunk or you blackmailed her. You did something." She was close to the truth and yet so far away. I had planned for something like this and had made a quick addition to the video from last night. I was pretty sure that one or both of Debbie's roommates would pull something like this. From what I'd heard from Debbie, they were pretty bossy and nosy and treated her like she was a little girl.

As preparation for this, I had burned a couple quick messages onto the video from last night already.

-You trust Jay-

-This video is sexy-

-This video turns you on-

-Jay is sexy-

-Girls are sexy-

I had no idea what effect these would have. So far I hadn't tested the messages on someone who saw them once and never again. The effects didn't appear to be incremental, they appeared to be abrupt at the time limit for that individual but I had no idea. This gave me the opportunity to mess with Debbie's roommates while experimenting more with the technique.

"Debbie, can you think of some way to reassure them that you were 100% willing last night?" I asked.

Debbie looked downward at the ground and said, in a soft voice, "The video... "

"Oh that's right, we videotaped it all last night, didn't we." I looked over at my wife with an evil grin. She was beaming back at me. I'd forgotten that she'd thrown out all of her old clothes so she was sitting on the couch wearing Daisy Duke shorts and a tube top. She'd probably been dressed for me when the girls got there. I pulled the DVD out of the computer and put it into the player. While it was starting up, "What are your names, girls?"

"Tiffany and Daphne... " one of them said before getting a "why-the-fuck-would-you-tell-him-that" stare from the other. I looked at the girls for the first time. Tiffany was a lithe redhead who reminded me a lot of the stripper from a few weeks prior. She looked like she might have been a dancer at some point but her breasts were larger than you would have expected for a dancer type. Daphne was shorter and blonde. She was a little curvier than her friend. Both of them were very cute and I was already mentally adding them to my harem.

The video started and the five of us watched. Kay had pressed up beside me and Debbie was clearly aroused from the whole situation. The humiliation and embarrassment of all this was driving her crazy and I could see her trying to inconspicuously rub her legs together.

Tiffany and Daphne both gasped as they saw Kay blowing me on the video. I knew that this part went on for 15 minutes but I was content to let them watch. The more they watched of the video the more (I hoped) that the messages would take effect.

"We didn't come here to watch some homemade porn of you and that slut wife of yours," Daphne said. Instead of being upset, Kay just beamed a smile and reached over to place her hand high on my cock and rub it as if showing it off to the bossy girl. This seemed to upset Daphne more and she turned back with a "humph".

"I can fast forward it if you'd like."

"Yes please," she said indignantly. I noticed that Tiffany wasn't nearly as upset and seemed to be staring at the video. I hit fast forward and Kay's image started bobbing frantically up and down on me. The effect was comedic and helped to break the ice just a little bit. I stopped when I saw my head turn toward the front door.

The scene unfolded on film exactly as I remembered it. Tiffany and Daphne stared for awhile at the film, unable to believe their eyes. Kay was now overtly stroking my cock through my pants while Debbie was practically shaking in the corner. I think she had come a couple times already. When we got to the part about my declaration that I wanted to show the video to her roommates she came again, twitching like she had last night.

Daphne snapped her head and yelled at me again, "You wanted to show this to us? What is wrong with you?" Tiffany was still watching the video. I was pretty sure that she'd be interested in fooling around without the messages at all. On screen I was now pounding away at my wife.

"Nothing's wrong with him," Kay said defensively.

I smiled lasciviously at Daphne and pointed back at the screen, "This is the best part." When she turned back around, I unzipped my pants and motioned for Kay to service me. My dick was rock hard after the flirting with Diane and the current encounter and it filled Kay's mouth. Daphne was watching, slack jawed, as Debbie started eating my wife in the video. On the other hand, Tiffany's legs were now rubbing together and her breathing was shallow. Debbie, for her part, had now openly crammed a hand down her pants and was sitting on the floor behind her roommates. The smell of sex was thick in the air.

When I told Debbie to leave on screen, Daphne once again turned to me and started to protest. Instead, she was cut short as she watched Kay bob up and down on my dick. She quickly shook herself free, "You people are sick!" she said and then realized that Debbie was frigging herself on the floor with abandon. "Tiffany, let's get out of here!" she said, getting even more irate. She realized that Tiffany was still watching the video and her hands had drifted to her chest. She grabbed her roommates, pulling Debbie's hand out of her pants and breaking the spell over Tiffany. The three of them left though only one of them really wanted to. Kay simply continued working on me and I quickly shot my come into her mouth.

After licking me clean, she looked up at me and said, "That went well."

"Did you see that Tiffany chick? I bet she'd have stripped right there for us if her bitchy roommate hadn't been here."

"And Debbie. She came just watching the video," Kay said.

"By the way, I'm going out of town tomorrow. I'll be gone for a couple days." Kay pouted.

"Big job? Who's going with you?"

"Small consulting job. Just Diane and me."

"I'll be sure to send you videos every night," she said seductively.

"Be careful, Diane's hot. You wouldn't want me getting uncontrollably turned on would you?" I was testing for the effects to take over. I knew they'd hit today or tomorrow.

"I thought we discussed this last night. Your cock is for me," she glanced at the video which had started looping back. "Well mostly me... "

"Of course dear," I told her.

The next day was a rough one. I woke up early for the flight and drove to the airport. When I got to the gate, Diane was already there. She was dressed very professionally. I'd actually worried a little bit about that but she must have realized that flirting with me brazenly in front of clients wasn't going to when me over. We sat together and talked briefly about the job. It really was a simple job and should be relatively relaxing. When they started boarding and the crowd around us cleared out a bit, Diane said, "Let me show you something." For a second, I thought she was going to flash me in the airport, but I needn't have been alarmed. She unzipped her carry-on and showed me what she'd packed. Inside were two work outfits and then a huge pile of lingerie, toys and pornos. I was impressed. She had to take the bag through security and most people wouldn't be crazy about the x-ray tech seeing their vibrators. Let alone the chance of needing a full bag search.

"That's... interesting, Diane. We'll discuss this more tonight." I boarded the plane and she followed me. We had a layover in Atlanta that forced us to pretty much sprint across the airport. I enjoyed running just behind Diane as she jogged the concourse. We got to our plane and arrived in Miami without further incident. I got a bit of work done on my computer but it's not that long a flight and I was distracted thinking about the evening ahead. We got the rental car and hopped in. Diane was sitting very close to me but keeping the discussion professional. And when we got to the client and she was stayed professional (thank goodness) after that. If anything, I think she was trying a little bit harder to impress me then normal. I'm not a partner so there's no reason to kiss up to me professionally. I can only assume that she thought this was yet another way to seduce me. Either way, it made the day fly by quickly and we drove back to the hotel. She still hadn't tried anything and i was wondering if I had rejected her too hard. We got our rooms and headed to the elevator. I was on the 2nd floor and she was on the 3rd. However, she decided to get off on my floor with me. "Where are you going?" I asked.

"Jay, stop it. We both know that you're going to fuck me. We both know that I'm going to do whatever you ask."

"Diane, let me show you something." I asked her to my room.

"Is this more of your wife's porn? I don't care. Fine, she's a cock pleasing slut. But she's not here right now. Unless she's flying down to meet you and fuck you in the hotel room, the fact is you won't be sticking your dick anywhere fun tonight unless it's in me." She was completely brazen now. We were standing in front of my room and I swiped the card. I opened the door and then grabbed her and pulled her in.

"Blow me," I told her. She didn't hesitate a bit. She dropped to her knees and unzipped my pants before the door even had time to swing shut. I grabbed her by the back of the hair. "Man you can suck cock," I told her as I tried something I'd always wanted to do but my wife wasn't able. I started thrusting my dick into her mouth, basically fucking her face. She took it like a champ. No gagging whatsoever and her tongue continued to work on me while I did it. Finally, I was ready to finish and pulled out and told her, "This is going to be the most degrading night of your life," as I shot my come all over her. Her face was covered but her tongue was working to wipe it all up. I opened up my overnight bag and took out my camera to snap some pictures. "I think I'll be sending these to Kay. She'll probably finger herself to sleep watching them. She's usually the one sending me naughty pics so this will be a good way to return the favor."

"So is that what you like? You want to control a girl? You want her to be a cheap gutter slut for you?" she said. She was stripping out of her clothes as she did and I marveled at the sight. Her body was so much nicer than the photo she'd sent me. Her tits were firm and her waist tiny. Without her clothes she could pass as a pornstar. Her mocha skin contrasted nicely to mine and the pinkness of her areolas matched her lips almost perfectly.

"If you want to be with me, that's what you need to be. If you can't do that, you can get out right now." I told her.

"You can make the decision after tonight." She said. "Just give me a chance."

"Fine. But don't fuck up. Like I said, I've got a nice cunt at home waiting for me." I knew the constant reminders about my wife would drive her. She was a classic Type A personality and I had intentionally played on that.

She stood up and took her bag to the bathroom. While she did that, I went over to the bed and laid out my clothes, hanging my suit up in the closet. By the time I was finished, she came out from the bathroom. I felt my dick go hard again as soon as I saw her. She looked like the hottest $50 whore you've ever seen. She was wearing a tiny jean skirt and garter belt and stockings. Her heels were 5 or 6 inches. She was wearing a tiny halter top that left parts of her tits hanging out the bottom. Best of all, she hadn't bothered to do any cleaning up from the cum that I'd blasted on her face. I took a picture of her then set the camera up to record. "Well you do look like a cheap gutter slut, I'll give you that." I motioned for her to spin around. She wasn't entirely comfortable on the heels but she gamely pirouetted anyway. The skirt was so short that her ass was hanging a little out of it and that made me twitch yet again. "Now that you know what I like, tell me what you want me to do to you."

"Anything," she said trying to sound seductive.

"I don't want submissive, bitch. I get that from my wife and her friend. I want a slut under my control but I want her to be slutty first and foremost. If you can't figure out the difference then this isn't going to work. I'm sure Laura would be happy to take your place," I said, raising my voice. I think that was the opening Diane needed. Now she knew how she could be "better" than my wife and boy did she run with it. The best part was, this wasn't her kink. I hadn't changed that. I just made her want me and prodded her enough over the last few days that she'd do anything. That thought made my cock go completely rigid.

"I want you to fuck my ass. Not gently either. I've never been fucked in the ass but I'm sure you'll make me like it. I want to fuck you in the hotel pool. I want you to fuck me while room service watches. I want to spend every car ride with my mouth wrapped around your cock. I want you to make me do things that I would never do otherwise. I want to be your personal whore and cumdump. I want to fuck anyone you tell me to for any reason."

"And what about your husband?"

"Fuck my husband. He's never made me feel like this. What you and I have is nothing like what I have with my husband. I wouldn't even call it cheating."

"Go back to your room and hang up your work clothes. You will NOT let your work suffer because of this and I want you looking and acting presentable. Do you understand?" Diane nodded "Good. Then come back here ready to get everything you want." When Diane walked out I watched her ass go and then I called my wife. I was fairly certain the next wave of programming had kicked in so I was prepared to have a little fun.

"Heya honey," she said when she picked up the phone. "I've got someone here who wants to say 'Hi' to you. She can't come to the phone right now, though. She's got some work to do. Isn't that right bitch?" she said.

"Tell Debbie I said 'hello'," I said with a chuckle. "Guess who just threw herself at me?"

"You're kidding? Diane? Isn't she married?"

"Yup... but that didn't stop her from coming up here dressed like street trash trying to get me into bed,"

"That little slut! I hope you fucked her good... uuhhh... right there slut," she said while clearly being distracted.

"I didn't want to do that until I talked to you. I wanted to honor your concerns,"

"Don't worry about that. I realized that with you on the road, you're going to have some little escapades. Besides, with all these women throwing themselves at you, we really should start a little harem. That's why I've got Debbie over here. I want her to be well trained by the time you get home." Yup, the programming had kicked in.

"Well, you'll be happy to know I came all over her face and then sent her back to her room."

"Oh that is hot, baby!" I wasn't sure if she was talking to me or Debbie.

"I've got a picture if you want it," I told her. I had already queued it up to send.