The Road to Hell... Ch. 06

Sorry for the long delay. Inspiration had struck me with my other story line and I'd been working on it. I'll try to get back to this one. I've got a bunch written but proofing and polishing takes time. Hopefully you like this next installment. I know it's a little disjointed because so much happens. Thanks for the kind words and hopefully the next installment doesn't take another six months ;)

*****

The light was dim in the house and it took time for my eyes to adjust. Once they did, however, I realized my time away from home had given my bride the opportunity to expand her horizons quite a bit.

What I now saw made my dick hard as iron. My wife was sitting in the same chair I was sitting in the day we first dominated Debbie. In fact, the scene was very nearly a mirror image. This time, however, it was my wife who was being serviced by a girl wearing nothing but some spiked heels and a collar. "This is Jennifer, Sir," my wife informed me. "She's the girl I met online as you instructed. She's even more submissive then I am. She's a complete dyke but she'll also do whatever I tell her. So you can use her all you want." The girl let out some muffled words but there was no way to tell what she said. "How was your trip?"

"Pretty great. Diane here... " I turned to look at Diane who was speechless about the scene in front of her. "Diane has been keeping me company. She actually thinks she can be a better slut than you..." I made it clear with the tone of my voice what I thought of that idea.

"Oh really? Diane, are you trying to steal my Master?" Kay asked her.

She stammered out of her reverie, "N... no... I just wanted to fuck him."

"And did you," Kay asked. Her hand found the back of Jennifer's head and she pulled the girl's head forcefully into her cunt. They both moaned.

"Yes... He was amazing," Diane said. She wasn't really aware of it but she was starting to show some flushed skin and was lightly stroking her neck. She was clearly getting aroused.

"Diane sucks some mean cock. Show her, Diane." To her credit, Diane had already learned to be obedient, especially when it comes to showing off a skill that she thinks might surpass my wife. Diane dropped to her knees and fished out my cock. I sat down in the chair opposite my wife. She and I gripped the hair of our respective servicers and moved them around to our whim. I made small talk with her in what was, I think, one of the most surreal experiences of my life. I got a good look at Jennifer as she continued to work my wife's pussy. She was a beautiful, petite girl with black hair and alabaster skin. Her boobs were little, perky orbs with bright pink nipples. She was probably 20 years old and had a beautifully submissive look to her.

"So have you stretched your plaything out?" I asked of my wife.

She was riding an orgasm and grunted a bit before answering, "Uhnn, no. I figured you'd like her nice and tight. I've told her to stick nothing in her cunt and to save that hole for you. Of course, you can have any of her holes."

The girl again mumbled something but it was muffled by my wife's legs this time. "Maybe we should trade. I've been fucking Diane and you've been fucking Jennifer. Seems only fair we see what the others been up to."

"I figured you'd say that. I went and bought a strap-on just for the occasion. I hope Diane can take it all," she reached down and pulled out a gigantic, almost comically large strap-on dildo. It must have been 9" long and two or three inches thick.

"You'll probably have to loosen her up a bit to get that monster in her. But I bet she'll scream." Diane's mouth was still wrapped around my cock and she couldn't quite see the monster Kay had pulled out. I kept her bobbing up and down on my cock while my wife strapped her new toy on. Jennifer was now sitting on the floor, legs spread and finger working her pussy as she stared glassy-eyed at the scene. I could see that this turned her on tremendously as her juices were starting to get the floor wet.

Kay finished strapping her tool on and positioned herself behind Diane. She started probing at the entrance of Diane's cunt. I knew from experience that Diane was naturally very lubricated and the girl was certainly very helpful. She put both hands behind her back and pulled her lips open for my wife. This gave her no support to hold herself up so, while my wife was impaling her pussy, my dick was buried into her mouth. It felt fantastic. What felt even better was when she started to moan on my cock while Kay started pumping her. After a few minutes of enjoying this sensation, I decided to try out my wife's new plaything. I pulled Diane's head off my cock and slipped out from under her. I'm not sure she even noticed as she immediately flopped her head back down on the chair and started moaning with my wife's thrusts. She was glistening with sweat and clearly still trying to get used to the size.

Jennifer was sitting and staring at my wife. The girl was clearly head over heels for her and completely enamored. I came up behind her and tweaked her nipple a bit. She stiffened and I whispered, "Don't worry. I'll make sure you enjoy this. You want to keep watching Kay?"

Her head nodded and she relaxed a bit. I slid in behind her with one leg on either side of her and lifted her onto my dick. She was slick and dripping and she slid down onto me easily at first. But Kay had been right. She was the tightest thing I'd ever felt. Even tighter than Diane's ass. I got about halfway in before she started to struggle with the effort. "Take your time," I whispered to her. She relaxed a little more and bent forward a bit. That gave her just a little more room and I was able to slide in. She moaned loudly and Kay looked over and smiled. Then we both went back to work, Kay hammering Diane and Jennifer fucking my cock from her squatting position. It was a huge turn on and there was no way I was going to last long like this. Finally, I gripped her hips and gave her one good pump into her pussy.

"Kay, get over here and put Diane on top of you." My wife eagerly obeyed, placing her head between Jennifer's thighs and pulling Diane on top. Diane slid down onto the strap-on easily, having already grown accustomed to the size. I moved from behind Jennifer and got behind Diane. I pushed her forward until her mouth was at Jennifer's cunt. "Lick it slut," I told her as I poked my dick at Diane's ass. As she tentatively reached out with her tongue to lick her first pussy, I slid my dick into her ass. My wife's strap on was stretching her fully and I could feel the sensation of her pumping shaft on the underside of my cock. Jennifer started to come almost immediately and Diane followed. There was no way I was going to come so quickly after the last time but my semi-hard cock was getting harder in Diane's ass. Eventually Kay came underneath Diane who was riding a nearly continuous orgasm from all of the stimulation. I pulled out and gave Diane's ass a slap.

I cleaned up and told Jennifer and Diane that they would be spending the night with us. I was going to fuck all three of them one at a time while the others watched. The night went by in a blur and I honestly remember very little of the details. Diane took the strap-on to Kay's cunt and clearly was trying to get some sort of revenge. I also fucked Diane's ass while she pounded my wife. Diane was really starting to enjoy the ass-fuckings. Finally, we all fell asleep in a jumble on our bed.

I woke up the next morning to a wonderful blow-job. Surprisingly, it wasn't Diane OR Kay but instead it was Jennifer who was slowly going up and down on me. Diane and Kay were laying on either side of me each running a hand along my chest and playing with each other's tits. "Jennifer wanted to thank you for being so gentle with her last night... Her past experiences weren't like that... "

I looked down at the girl and realized that some of the other pieces were falling into place. "She's quite good for someone with limited experience," I said as the girl mumbled something in acknowledgment of my praise. "I guess we're going to have to start establishing some rules around here. I don't want my harem to be left to their own designs." Kay shuddered visibly and reached out to push Jennifer's head down on my cock. I arched my back and enjoyed the sensation before continuing, "Kay, we're going to have to look for a bigger house I think something very, very large. With everyone's combined income we'll be just fine. Jennifer, you will move in with us immediately. Diane, you're going to lay down the law to your husband. He will never again have you. Do you understand?"

"Yes, Sir."

"Can you handle that?"

"He's nothing compared to you. I'll let him know that he can sleep with whoever he wants from now on but the intimate side of our marriage is over."

"Good," I turned back to Kay. "Debbie will also need to move in with us. From now on, the four of you are to only wear lingerie when at the house. Kay, when you start looking for a house, try to find something secluded so that we can have parties and not have to worry about neighbors."

"Yes, Master."

"Kay, you are in charge of the harem's dress code. Each girl will have one expensive slutty outfit. Something elegant. One cheap slutty outfit. And something sexy and casual. That will be their entire outfit for outside the house unless they're working. I don't want anyone getting in trouble for wearing something crazy to work so don't mess with their work clothes. Everything else they own will be lingerie. Go ahead and purge out every plain bra, every pair of pantyhose, every pair of granny panties. G-Strings, thongs, shelf bras and garter belts should be the clothes of choice. That goes for you too, my love."

"Of course, Master."

"Actually, go ahead and get Jennifer and Diane set up. I want to be the one that shows Debbie what she'll be wearing from now on. In fact, that sounds like a good project for today. Let's go shopping. Kay, you take Diane home so she can break the news to her husband. I don't want anything violent to happen there. Then take her and Jennifer to get them their new clothes. I'll go pick up Debbie."

"I was hoping to go with you, Sir," Diane said.

"No, you need to take care of things with your husband. Besides, I'm going to enjoy my day alone with Debbie." I stopped talking and concentrated on Jennifer's tongue. She WAS remarkably skilled for someone who hadn't done this before. Before long, I was shooting into her mouth and then we were getting ready. As I left, I remembered Debbie's roommates. I figured I'd leave them with a little surprise. I burned a new copy of one of my wife's chick flicks and then overlaid my program onto it. I thought about the messages and how I wanted to mess with them... Especially Daphne.

-Jay turns you on-

-Kay turns you on-

-You have to obey Jay-

-Resisting your urges turns you on-

-Obeying Jay and Kay turns you on-

-You hate obeying-

-You hate being forced to obey-

-Being forced to obey turns you on-

-You want to watch Jay's porn-

I hit the execute command and headed over to Debbie's house. I knocked on the door and was surprised to find Tiffany answering the door. She saw me and paused for a second and then smiled, "What's up," she said and kind of twirled her hair.

"Is Debbie here?" I asked, looking over Tiffany's shoulder into the apartment.

"She just went for a jog. I'm sure she'll be back in a minute. Why don't you come in and sit down," she said and turned. For the first time, I noticed what she was wearing. It was a pair of short, exercise shorts and a tight, white t-shirt. I realized that her nipples were practically poking through the front of her shirt and I was mildly upset at myself for staring into her eyes when she answered the door. "You left a pretty big impression on us the other day. Daphne does NOT like you."

"Fuck her," I said. I was remembering Tiffany's reaction more at this point. "What about you?" I called after Tiffany who had walked into the kitchen.

"I'm a lot more... uhmm... free-spirited you might say," she said as she walked back into the apartment. Her hands reached for her t-shirt and she pulled it over her head. Then she turned her back to me and pulled her shorts down slowly. "Daphne doesn't know but I used to work as a stripper when I was still in school. I didn't even do it for the money. I have a trust fund. I did it because there's nothing like a hard-cock rubbing up against you. We'd better hurry if you want to be fucking me when Debbie gets back."

She was so matter of fact about it that I was still speechless. She bent over the table and reached between her legs to spread her lips for me. I'm no fool and I quickly recovered my composure. I dropped my pants and moved up behind her, "She's been getting herself off every night. I can hear her saying your name and your wife's name. I've just got to know what she's getting."

"Here it is," I said as I jammed my cock into her. She screamed like an animal and gripped the edges of the table. I was slamming her for about 20 seconds before we heard the door. Her screaming and wailing was so loud that I'm sure Debbie heard it on the other side and she started to rush in.

"What's wro... oh god," she said. The effect was amazing. She had an orgasm right in front of us and collapsed against the wall.

"Holy fuck... " Tiffany said breathlessly as I pounded her, "Daphne's right... uhnn... about you... uhmm... being a slut now... "

Debbie was recovering and flushed afresh from her roommates words. "Don't say that," she said with barely mustered resistance.

"No... No... I'm... oohhhh... really proud... of you," Tiffany grunted. I was getting close to orgasm.

"Debbie, come over here and kneel down," I told her. She dropped and crawled to me. When she got close, I pulled out from Tiffany and shot my come all over Debbie's face, hair and shirt. She came again and collapsed while Tiffany giggled. Tiffany leaned down and gave Debbie's face a nice lick.

"MMmm.. you even taste good. No wonder Debbie's gone all turbo-slut for you."

"She's about to complete her transition. Debbie, you're going to move in with us and you and I are going to go shopping for your new clothes." If she'd had any resistance left in her, the two orgasms had ripped it out of her.

"I'll go change... " she said but I put my hand on her shoulder.

"No, you'll be wearing that. And you won't be cleaning up," I told her. She shuddered but didn't object. "Tiffany, do you have any scissors?" Tiffany hopped up and went to the kitchen. I watched her ass for a moment before turning back to Debbie. "Give me your shirt and take your bra off." Again, she did as she was told. Tiffany came back with the scissors and stared openly at Debbie. Debbie flushed red all the way down to her full, lovely breasts. I took the scissors and cut off the bottom third of the shirt and gave it back to Debbie. The cloth that was left was now short enough that it hung off her breasts and, if someone was below her, they'd be able to get a full view of her tits. "Now, give me your shorts and take off your panties," if I'd thought she couldn't get any redder I'd have been wrong. She was shaking from embarrassment, humiliation and arousal.

Tiffany knelt down and said, "Let me help," as she slowly hooked her fingers into the waistband of Debbie's cotton underwear and pulled them down. Her mouth was inches from Debbie's snatch and I'm sure Debbie could feel her hot breath. Debbie looked down to see Tiffany stick a long, pointed tongue out and move it closer and closer to her clit. When it had just barely grazed it, Debbie came again, leaning against the counter to avoid falling to the floor in ecstasy. I took the scissors to Debbie's shorts, cutting off the bottom third and putting a deep slit on each side. When I gave them back to her she slid them on. The effect was perfect. She looked like a gym teacher...in a porno. Her ass cheeks were hanging out and it was obvious she had no underwear on.

"Go put on some heels so we can go shopping," Debbie walked into her room and Tiffany and I both watched her ass shake as she went.

"What about me?" Tiffany asked. "Mind if I come shopping with you?"

"Not at all," I told her. Shortly Debbie came out wearing a pair of 3 inch, very conservative heels. "Is that the best you have?"

"Yes... " she said meekly.

"I guess that's one more thing we'll have to buy while we're out. Tiffany's going to come with us and help us find 'appropriate' clothing for you," I told her. Debbie nodded. We all went down to my car and got in. "Let Debbie ride up front, Tiffany. She's going to have her mouth busy." Tiffany grinned, opened the door and gave Debbie a swat on the ass as she climbed in. Debbie moaned a bit and blushed red again. I just unzipped my pants and pulled my dick out. Debbie knew just what to do and wordlessly bent over to start working my cock. Tiffany and I made small talk while we drove. I'm not sure if Debbie was humiliated by being ignored or if she was just embarrassed to be acting this way in front of her roommate. Either way, the effect was intense. She moaned endlessly on my dick and got herself off two or three times before we got to the store. I had driven to one of the "nicer" sex shops in town. I don't really like the seedy places.

"Oooh. I love this place," Tiffany said as she hopped out. Debbie unlatched from me with a gasp and climbed out herself. There was still some dried cum in her hair and her lipstick was a mess. I was sure that Kay was going to be amused by the lipstick ring around my dick when I got home. I had told Debbie what her new dress code was already (that certainly caused one of the orgasms while she was blowing me).

When we got inside we were treated to a whole building full of erotic stuff. This place catered to everyone's kinks. "We're looking for something really slutty for her, Tiffany. I mean really, really slutty." Debbie was trying to hide the little moans, "Something that's so slutty that people will be CERTAIN she's a whore." Debbie put one hand against the nearest clothes rack. Fortunately, places like this weren't particularly crowded so Debbie's little display went unnoticed. Tiffany just smiled and continued looking through the clothes.

"Cheap and slutty should be easy here," Tiffany said as she held up a skirt that could have passed for a thick belt. "I think you're going to have trouble with elegant slutty, though."

"I have a thought for that. Let's focus on something really, really trash for her for now,"

"Oooh... I like this," she held up a bright blue jean skirt. It was longer than some of the crazy micro-mini skirts they had but it was still going to be dangerously close to having her ass hang out. There was a slit up the side that went all the way to the belt loops and had triangle cut outs in the middle of the front and the back that would make sure that everyone knew she wasn't wearing underwear and she probably kept herself shaved.

"Nice... Now what kind of shirt would go with something like that." We found a variety of shirts of various shapes and sizes. I wanted something that accented Debbie's large chest and cleavage. Tiffany found a couple great shirts that would have looked terrific. But nothing that was really "cheap" enough for what I was going for. and certainly nothing that would was going to go with a trailer trash skirt like we'd picked out. Finally, I realized we were making this entirely too difficult. The perfect shirt for the outfit was something simple. Something like...

"This," I said. It was a simple black polo type shirt. It was a size too small and the buttons went down farther than normal. Tiffany kind of frowned because she didn't quite get it. I pulled at the string of one of the buttons until it fell off on the floor and Tiffany realized what I was going for. There were four buttons and when we were done, the shirt would never be buttoned again. That combined with the small size would ensure a glorious expanse of breast to be exposed. "But the best part is this," I turned the shirt around and showed the girls what it said on the back, "If you can read this you're doing me right!"