Chapter 2

--------------Present day-------------

The Asian girl staggered down the steps from the condo, having taken my cock in both of her holes. Cassie had given her plenty of orgasms, so I didn’t feel all that bad for her. I had made her eat Cassie’s pussy while I’d drilled her up the ass, but she seemed to have trouble concentrating and thus, Cassie hadn’t gotten off. I was angry that she had ditched me, so I left without fucking her. Later that night, I reviewed the video from her bedroom to see that she’d fucked herself in both the pussy and ass with toys right after I’d left.

It was late in the afternoon but I wasn’t quite ready to go home. As I drove through town I realized that I was right next to my old High School, so I decided to drop in and see a friend.

The bell had just rung so students were beginning to exit the building. I parked and strolled in, knowing that I didn’t have any business there but I knew that no one would stop me. I walked down the hallway, feeling the eyes of several of the students on me. I briefly considered stopping to flirt with some of the girls but I was hungry for something else. I grinned as I pushed open the classroom door.

“Carter!” Ms. Bliss cried out.

“Hey there.” I grinned.

“What are you doing here?” She asked, concern climbing into her voice.

“I just came to say hello. What, I can’t stop in to see a friend?” I asked in a hurt voice as I closed the door behind me.

“Uhm, well, sure. Sure you can. It’s just that I didn’t expect you to come HERE.” She replied, emphasis on here.

“What’s wrong with here? I mean, we have all sorts of great memories in this room, don’t we?” I grinned, walking towards her.

“Yeah. Well, yes, we do.” She stammered.

“Do you miss our little tutoring sessions?” I teased, putting my hand on her desk.

“Carter, please. We can’t...” She pleaded.

“Oh, but we can. We can and we have.” I smirked.

Many months ago, Ms. Bliss informed me that she had a boyfriend and that she needed to end things with me. That was a good idea, in theory. In reality, she just couldn’t resist me when I put the pressure on her. I’d spent many evenings drilling her silly and pumping my cum into all of her holes. Every time I did, she swore it would be the last time. But, the next time I’d come over, she’d end up on her knees with my cock in her mouth. We didn’t talk about her boyfriend, though I was fairly confident that they were still together.

I loved tormenting her, though I knew that deep down she loved it as well. She was addicted to me, and seemed to be rendered pretty helpless when I was around. I love it. I craved it. I once thought that money was power. I was learning however, that sex was power. Money can buy sex. Money can buy drugs. Drugs can get you sex. But, getting sex without the help of anything else, that was power.

And it was intoxicating.

I loved making women do things that they hated to do. Candace was taking it up the ass regularly. She was being traded off to random men without complaint. Cassie knew better than to say no to me, though she rarely complained about any of it anyway.

“Carter, we can’t do this any more.” Ms. Bliss begged.

“You keep saying that, but we know what’s going to happen. Stop playing hard to get, we both know what you really want.” I grinned, rubbing my crotch as I walked around the desk.

Ms. Bliss tapped her hand on her desk nervously.

“Carter, please. Understand. Me and Paul, we’re...” She stammered and then looked down at her hand.

I followed her eyes and saw a shining ring on her left finger.

I froze, staring at the small diamond. For some reason I felt hurt, betrayed and abandoned. It wasn’t like I was going to marry Ms. Bliss, but she was mine. I owned her. Now, this other man was going to try to take her away from me?

Not happening.

“That’s a cute little rock. At least he could have gotten something you could see without a magnifying glass.” I snarled.

“Carter, I love him.” Ms. Bliss started.

“You also love my cock and you fucking know it.” I shot back, rubbing my crotch again.

“Carter. Please. Please don’t do this. Please don’t do this.” She begged.

“I’m not doing anything. You on the other hand, are gonna get on your knees and suck my fucking cock. Hopefully you can get me to cum in your mouth. If not, I’ll be forced to pop off in your hot little pussy and send you home.” I grinned.

“Carter, please! Please stop. I can’t do this!” She cried out again as I grabbed her by the arm and lifted her to her feet.

“It’s up to you teach. What’s it gonna be? Mouth, pussy, or...” I grinned then reached down and squeezed her firm rear.

“The ass.”

I leaned closer to her ear and lowered my voice.

“We both know how much you love my big fat cock up your ass. Would you like me to take you there, right now, over your desk? We never actually did that when I was a student here. Perhaps we should check that box. What do you think, Ms. Bliss? Would you like to feel my dick up that sexy ass before you go home to Paul?” I taunted, sliding my hand down and tugging her skirt up.

“Please no. Please no. Carter. Carter, please.” She panted softly, her eyes closing.

“Pick a hole, Ms. Bliss. Any hole. Any hole.” I grinned, rubbing my fingers between her ass cheeks.

“Oh Carter. Oh Carter. This is so wrong. This is all so wrong. Why can’t I stop you?” She cried.

“Because you fucking love it and you know it. So, what’s it gonna be? On your knees or over the desk?” I asked, pulling her panties out of her ass crack and teasing her anal pucker with my fingertip.

Ms. Bliss shuddered and gripped the edge of the desk as I pressed my fingertip into her ring.

“On your knees, or over the desk?” I asked again.

“This is so wrong. So, so, so wrong.” Ms. Bliss whispered. I could feel her body drop and I pulled my finger out of her ass as she dropped to her knees.

“Who cares if it’s wrong? You love it and you know it and I do love your mouth. Don’t sweat it. It’s just sex.” I grinned, looking down at her as she extracted my cock out of my pants.

“It’s just sex.” She repeated as she sunk her head down onto my shaft.

I did end up fucking her over her desk, but in the pussy.

Pleased with myself, I left Ms. Bliss in a sweaty, stinky mess in her office and strolled out to the parking lot of the school, feeling the eyes of several students on me again. I slid into my car and drove home.

Candace’s car was in the driveway, as was Lindsay’s.

Over the summer, Lindsay had finally found the courage to break up with her girlfriend and move out. I don’t know why or when, but Candace and Lindsay had become relatively close friends and Candace had asked me several times if she could move in with us. I’d deferred. Not because I cared, we had plenty of room, but I wanted to keep Candace in my debt and good graces. I figured that holding something that she wanted over her head would keep her in line.

I knew from the sounds, and from my video cameras, that Candace and Lindsay were fucking regularly. The tone of their sex had changed though. It was much more sweet and loving. Gone was Candace playing the dominatrix with the blond girl. I’d often seen Candace returning the oral favors to her and there was a lot of passion in it. I did have to admit that watching the two of them alone was pretty hot, but I certainly enjoyed getting in the middle of it.

I walked inside the house and paused. I didn’t hear any noises coming from the play room, so I walked up to the second floor. That’s when I heard the very soft but distinct sounds of girl pleasure.

With a grin, I walked towards Candace’s room.

The sound grew louder.

Candace’s bedroom door was open, so I walked in and leaned against the door frame.

The room was a mess of clothes and sex toys. Candace was in the middle of the bed, naked, with her fabulous ass up in the air. Lindsay was behind her, also naked, her face pressed into Candace’s ass.

“Dear God, how long is your tongue?” Candace moaned.

“Do you like it Miss?” Lindsay asked.

“I love it. I love it. So good. Don’t stop. Don’t stop.” Candace exclaimed.

I watched as Lindsay licked all the way up and down Candace’s slit. She spent time dragging her tongue over Candace’s pink pussy before moving Northward and shoving it into her brownish anal ring. My eyes roamed over Lindsay’s tight body and I noticed a round, shining object between her perky ass cheeks.

“Looks like you two are having fun. Mind if I join in?” I called out.

Both girls screamed and jumped. On reflex, Candace pulled a sheet up over her naked body and I grinned as I walked into the room. Lindsay landed on her ass on the floor at the foot of the bed and I could see her wince with the pressure on her ass.

“Don’t stop on my account.”

“Carter! I thought you were out!” Candace exclaimed.

“I was. I’m home now. Room for one more?” I smirked as I walked towards them.

“Uhm, well, you see, we were...” Candace began.

“You two were fucking. I saw that. I got no problem with that, I love to watch you two. I really love watching you two suck my cock at the same time. So, how about it?” I grinned. I pulled my cock out of my pants and stood in front of Lindsay, holding it out towards her. Lindsay glanced at Candace with a worried look on her face.

“Don’t worry, I can share. Come on down, both of you.” I said firmly, grabbing the back of Lindsay’s head and pushing it down. She resisted for a moment and then opened her mouth and took me in.

“You’re getting better at that. Get down here and show her how it’s done.” I said in a strong tone, staring at Candace as Lindsay bobbed up and down on my dick.

Candace slid off the bed and onto the floor next to her friend. I pulled my dick out of Lindsay’s mouth and offered it to Candace. She gazed up at me with a pained look, but sank down onto it.

Lindsay ended up nearly blacking out when I fucked her ass later that night. Candace was eating her pussy while she rode me anally reverse cowgirl and when Lindsay fell sideways off my dick, Candace got a surprise face full of my cum.

-----------Weeks later----------------

I was fighting to stay awake. At Brad’s insistence, I’d begun to attend company board meetings. My father had recommended that I sell out my stake in the company for millions, but Brad recommended that I try to get involved with the company for a little while before making that decision.

The other board members did an excellent job of hiding their annoyance at my presence, but it wasn’t hard. I very rarely, if ever, actually spoke in the meetings. They went on and on about buy outs and mergers while I played on my phone, scrolling through various hook up apps.

Jessica, my secretary, scurried about the conference room, bringing drinks to the various board members. She looked quite sexy today, though I’d been picking out her wardrobe for some time now. She cast me a sideways glance and I grinned at her. She looked away nervously and scampered out of the room.

--------Over the summer---------

She was in her mid twenties, just a touch older than Ms. Bliss. Slender body with handful sized breasts and long blond hair. Just my type. She was married and after chatting with her a bit, I found out that both of them were drowning in student loan debt. She’d taken a secretary job since she couldn’t find anything in her field, which was something silly like basket weaving or art history or something. Regardless, I got the distinct impression that she was dying for money and desperately needed the job.

I’d briefly considered a financial arrangement like I had with Ms. Bliss, but decided that wouldn’t be as much fun.

It started easy with simple comments about her outfit, her hair or her eyes. She’d blushed and thanked me politely, but I could see that it made her uncomfortable.

Watching her squirm was quite entertaining actually and I had to hide my laughter when she jumped in the air the first time I grabbed her ass.

It had come to a head one day hot summer day when I’d asked her to bring me some water. She’d leaned over my huge desk and I’d caught a glance of her pink bra as her shirt fell open.

“Does it match?” I asked, grabbing the water bottle.

“Does what match, Sir?” She asked, standing up.

“Your bra, does it match your panties?”

“Uhm, what. I don’t understand, I mean...” She stammered, clearly uncomfortable.

“It’s a simple question, does your bra match your panties?”

“I’m sorry Sir, I don’t see how that’s relev...”

“I take it you like your job, don’t you?” I said firmly.

“Yes Sir, I do.” She quickly replied.

“Answer the question.”

“Uhm, yes Sir, they do match Sir.” She replied softly.

“Excellent. See, was that so hard to say?”

“No Sir.” She replied, looking away.

“Prove it.”

“Excuse me?”

“Prove it, show me.”

“What! I can’t!” She shrieked.

“Sure you can, it’s simple.”

“I can’t!”

“Yes you can. Unbutton your shirt and show me your bra, then pull your skirt up and show me your panties. Simple.” I said calmly, sipping from my water bottle.