The Cougar of Montgomery Ch. 04

Chapter One

I sat at the hotel bar and took nervous sips of my apple martini while obsessively clicking my phone to see what time it was. When I was first served, I nearly gulped the entire thing down at once, then I remembered I had twenty minutes to kill and I shouldn't have more than one of these things on an empty stomach. Not tonight. I did my best to watch people outside the bar in the bright lobby of the hotel. The freshly waxed floors reflected the chandelier lighting from the ceiling as suited men and dress-wearing women filed in and out.

Must be a formal event going on tonight. I thought. Saturday night, maybe a wedding.

It was a fleeting thought that gave me a much-needed distraction. I found myself jealous of this imaginary wedding. A secret bride and hidden groom off somewhere to be wed. I wasn't jealous of their marriage- god no. But of the excitement of possibilities. What will the future hold for them? Will they buy a house? Move to a new town? Start a new job? All the possible outcomes sounded so fresh and possible. Meanwhile, I sat here in the low-lit and musky bar, facing a bleak future.

Over the years, as I crept into middle age, I've resigned myself to realizing the half of the American Dream that called for me to be married and have kids was not my future to have. The fiction of finding prince charming to whisk me away into a happily ever after never interested me. I was a career-minded woman. My life was grounded in a carefully molded reputation as a tenured professor at a respectable university, and my ability to provide for myself was based on this one possible skill of teaching. Now, because of my stupid horny decisions over the past weeks, everything I worked for over the last 20 years was in jeopardy. So much so that losing my job and reputation no longer felt like a possibility but an inevitability. All it would take is a slip of Justin's tongue to the wrong person or an intentional outing of my sexual life with my students by Jessica.

Jessica texted me shortly after her and mine encounter last weekend. She poked and prodded with intrigue at how I enjoyed our little 'meeting,' as she put it and inquired about a future one. Despite my reservation and attempt to steer the conversation to an amicable parting of ways, Jessica insisted on this Saturday. She invited me to make the reservations this time around and I gladly accepted that offer. At least I won't have to worry about bed bugs or getting robbed at some trailer trash motel this weekend.

When I informed Justin about the conversation, I winced the whole time, waiting for him to demand I disobey Jessica or that he would confront her or some other juvenile response to this real danger I faced. Nonetheless, I told him of our hotel room and date and time we were set to meet. He didn't reply at first. He just laid there shirtless beside me on his mattress, quiet and in thought. After several moments, Justin simply said, "Okay." It wasn't until after he gave this simple response that I realized this was possibly the worst answer he could give. It meant that I was alone in this.

Now, five minutes before our scheduled meeting time at the room, I wonder to myself, am I excited or dread going into that room and facing Jessica again? It was true she awakened feeling for a woman inside me that I had never experienced before. And when I did cum, it was strong, but there was something else there, too. A type of aggression that unsettled me. A misalignment in the kind of dom she was and the kind of sub I am. I shook my head; did it matter how I was feeling? I didn't have a choice when it came to her.

I finally downed the last sip of my now warm apple martini and left the bar. On the 4th floor of the hotel at the end of the hall, I found Jessica leaning up against our door waiting with a smirk on her lollipop-red lips. Show wore a bright red glitter dress that clung to her petite frame and barely hung on to her by the two small spaghetti straps on her shoulders.

"You're a little late, professor," she said, tapping her imaginary watch on her wrist.

I gave a quick smile, "Sorry, had to wait for an elevator."

"Don't worry, I'll make sure you're sorry in a minute," she said, hovering over my shoulder as I unlocked the door. The room was as nice as the rest of the hotel. Modernly decorated and spacious. A large king bed with a table and chairs beside it. Jessica walked past me with a smile on her face and her hands in the air, as if she was previewing the room for me. "Wow, look at this place. You shouldn't have." She stopped in the center of the room and made a twirl while brushing off her dress. "Such a fancy place I thought I'd better dress for the occasion."

"You look great," I said.

"Great?" Jessica sounded offended. "Great? Just great? Looks like we're going to have to start early then, huh? I'm going to need you to get on your knees for that."

I felt small and insignificant walking over to her. Like a beat dog walking to its punishment. Standing in front of her, I went to raise my skirt so I could move to a knee when a quick patter on the door was heard.

"Mmm... did you order some room service?" Jessica bubbled as she skipped over to the door. "I really could go for some Champai-"

She opened the door and froze mid-sentence. Standing on the other side of the door was a larger lady. She was heavy-set but with ample breasts that bounced in her gray dress. Her beautiful long blond hair flowed behind her. It was Amber, my assistant. And she was as white as a ghost. The silence hung almost too long before a familiar voice chimed in.

"I don't know about Champaign, but I did bring some wine," Justin said, appearing beside Amber.

"What- what are you-" Jessica stuttered. "Why are you here?!" The question seemed shot at both of them but with separate connotations.

"We're here for the party," Justin said, walking past Jessica with eyes locked on hers the entire time. Justin was relatively well dressed. He wore a pair of clean black jeans with a black button-up shirt that fit him well. Jessica glared at him, then shot a look at Amber and finally at me. "You invited them?" She spat. The disgust is heavy in her voice.

Before I could even try to stutter a word free, Justin took over. "No," he simply said. "I invited me. And her, you know Amber, right?" Jessica fidgeted, crossing her arms. It was the first time I had seen her uncomfortable and out of place.

"You and Amber have been seeing each other for some time now," Justin said, as a matter of fact, then added, "She told me." I shot a look of shock to Amber, who only barely now crept into the hotel room and let the door shut behind her. Her eyes were low and her fingers were kneading each other. After letting the information sink in, Justin looked at me, "Amber was the one who told you when to walk into Professor Mill's office to catch her in the act- that part I put together for myself." Justin said, leaning against the sink. "And Amber's the one who helped you mess with the professor on the group chat on the computer in class, too."

Finally, Justin waited silently as he stared at Jessica. Until she glared back at him and said, "So you're the side piece she was fucking with behind my back." Justin just stared at her with a ghost of a smile in the corner of his mouth. "Professor," Jessica said with the edge of arrogance back in her voice. "Tell this trailer trash boy to leave and maybe I won't ruin your life." She emphasized that last word as her gaze fell hard on me. "You will fuckn' leave, too," Jessica sent a glance towards Amber.

Amber moved at once, turning for the door, but was halted by Justin's command to stay. "You know, you're right, Jessica. I am trailer trash. We don't travel in the same circles. The few times I've seen you at a party that overlapped with both our crowds, our people never hung out with each other. In fact, this math class created for morons is the only class we have in common." Justin crossed his arms as he spoke. "Your family, I bet, are important people. Rich and established. I bet your Dad's some CEO asshole and your Mom's a stay-at-home alcoholic. That's your Mercedes in the parking lot, isn't it? The one with all the pink shit on the trunk. I recognized it from school. I bet you have some bullshit major to go with it. Like fashion or interior decorating."

"You know, what cock sucker? Fuck you!" Jessica snapped. But Justin continued with his speech, unphased.

"Me? I have an even bigger bullshit major," he said. "Criminal justice. Easiest fucking degree, but I figured such a blue-collar job would be fitting for some trailer trash like me. But you know something I did learn in my bullshit degree this year? Using coercion or blackmail are illegal."

Jessica made a face and shook her head, unimpressed. She was finally starting to see Justin's play in this battle of wills and she didn't think it was a good one.

"I know, I know," he continued. "It's not a common one and I'm sure one of your big wig family members has even dealt with it before. I'm sure you learned your cute little femdom ways from one of them, strong-arming your way into people's lives. Who gives a shit about a little misdemeanor charge of blackmail? But then I looked again and saw if you used coercion or blackmail to force another party into sexual activity... that's not called blackmail anymore. That's called rape."

The hard-jawed grin that was on Jessica's face slowly slipped away now. There was a look of disbelief in Jessica's eyes as she shifted in her stance some. And I, for the first time during Justin's speech, just realized he was talking about me.

"No, it's no-" Jessica started but was cut off.

"And man did you fuck up," Justin's voice boomed louder now. "Creating a digital log-in group chat that can be looked up, not to mention texts, hotel security cameras, involving witnesses that will be compelled to confess against you," Justin pointed to Amber. "Victimizing a well-established professor." Jessica's looks turned inward as she digested the words. "I mean I'm a fuckin' 2nd year CJ student and I can put this case together at ease. And that's just the legal system. Imagine mommy and daddy finding out their daughter is a rapist? Imagine spending the rest of your life registering as a sex offender."

Jessica was stuck in a state of shock. Her speechlessness was only matched by mine. This sounded like some kind of trick. Like Justin was at a poker table trying to sell a bluff. I felt like I was watching a chess match. I had no say in the play out in front of me. And Jessica had just lost her queen.

"Feel free to do a search on your phone or call daddy's lawyer if you want to verify that you're fucked," Justin said. "You can fuckin' leave now."

Jessica smeared a look of defiance as she rallied her shoulders back for a fight. "You don't talk to me like that you trailer trash!" She shouted. Justin walked slowly towards Jessica until their shoulders were squared another. For a moment, I was worried it was about to get physical with one of them hitting the other. But Justin simply turned to Amber and I with a light smile and asked us to leave the room.

Without a word, we left the room. It was kind of humiliating. I, a 40-year-old woman being sent out of the room like a child so the adults can speak. But at the same time, I really did not want to be in that room at that moment. I stared at the door for a minute from the hallway, listening for shouting, breaking glass, and a gunshot. Anything was possible at this point. When I finally did turn back to see Amber, she was already a mess of tears.

"I'm so sorry, Professor Mills!" she cried. "Since my divorce, I've been a mess and I haven't been sleeping and putting on weight and these diet pills don't work and have been putting me in such bad mood swings. And Jessica- she was just so- I don't know- she came out of nowhere and it had like a calming effect on me, the way she punishes me and helps me and I never told her anything about you at first but-"

"At first? How long have you been Jessica's sub?" I finally interjected.

"3 Months," she sniffled.

"And you told her when she could walk in on me in my office?" Her response was an even louder and messier cry. "Why were you with Justin tonight?" I asked.

Amber sniffed and shook uncontrollably as she tried to center herself. "He- he asked me out on a date last week. He brought me here- I- I thought it was a hotel room for us. But we never- we never even kissed!"

I sighed, closing my eyes as I leaned against the hallway wall. A few well-dressed women exited the elevator and stumbled into a hotel room across the hallway. After a long moment, I looked back at Amber. "You helped her blackmail me?"

Amber immediately began crying again. "Amber stop," I commanded. And to my surprise, she did. "You put my career at risk. My entire life really, just to make your girlfriend happy. You almost cost me everything..." I took a deep breath. "You're going through a lot. I understand that," I said calmly. "Jessica, she helps you... deal with things?"

Amber nodded while looking down at the floor. "You're quitting your job. Effective immediately," I said. Before Amber could break down in tears for the 5th time, I quickly added, "But... since I wasn't the most professional person either, I'll put in a good word for you with another professor. I hear Professor Tibbits and Steele are looking for an assistant."

Amber's eyes lit up. "Thank you!" She cried. I nodded and felt in control for the first time in weeks. They stood outside in silence for five minutes more before Justin opened the door and signaled for them to enter. Jessica was kneeling in the middle of the room in her dress with her eyes locked on the floor. The sheer lack of her presence in the room was astonishing. It was as if she wasn't even there. Her shoulders were caved forward, and her hands were resting on her thighs. It was clear who had won in the battle of the wills.

"You may go," Justin simply said. Slowly, Jessica stood and walked towards the door. The closer she got to the door, the taller her spine became and the higher she held her head. She didn't look at me as she passed but glared at Amber.

"Outside, Amber," Jessica snapped as she went outside. For the briefest of moments, the smeared sad look on Amber's face turned to a wicked flash of delight at the prospect of what was to come, and she quickly disappeared out the door.

Chapter Two

I watched Justin move to the hotel door and casually peer out the peephole as he latched the chain lock. "You shouldn't have any more issues with Jessica," he said.

"What happened in here?" I asked.

"We had a conversation, and she listened for a change," he said. He opened the bottle of cabernet Sauvignon wine near the TV and poured a glass for each of us in silence. We sat listening to some music I never heard before play from his phone for several minutes while drinking our wine and relaxing. Oddly enough, sitting together and not speaking wasn't as uncomfortable as I would have thought. After the past few weeks, it was a welcome moment of peace. My career, my livelihood, and my life felt secure for the first time in what felt like forever. I could breathe and live in the moment.

"I like this music. I've never heard it before, who is it?" I asked.

Justin smiled to himself as he poured a third glass of wine for the two of us. "I'm not surprised you haven't heard it before. It's my band. You really like it?"

"Really?" I asked, turning to him. The music switched from a full rock chorus with drums pounding in the background to a lighter almost indie guitar plucking solo. "Yeah, I'm feeling this. Especially this. Are you the singer?"

He laughed, blushing some, and crossed his feet on the bed. "Hell no, you couldn't get me to sing if you put a gun to my head," then he pointed casually to his phone. "I'm the one doing the guitar solos."

"Really?" I said, feeling the flushness warming my cheeks. "That's like my favorite part."

"Thanks," Justin adjusted in his seat while taking another gulp of wine. It was the first time I'd seen Justin not in control and even slightly uncomfortable. It made me smile how cute he was when he wasn't busy being his usual in control sexy self. My eyes washed down his body, pausing on the crotch of his pants and I felt a warm swirl rise from his thighs. I sipped my wine as I softly grind my thick thighs together in warm circles. Biting my lip, I released a long sigh.

"Was that true?" I asked. "What she did- said- what she said to me- sorry. But does that make it rape?"

Justin shrugged, finishing his glass of wine. "I would think so, but then again I'm a third-year cj student so-"

"I never thought about it like that. I mean, I was scared she was going to ruin my life and all. And getting fucked by her wasn't, like, a goal of mine but I didn't not like it," I realized that I was rambling and slurring her words when I saw Justin just sitting in silence watching me talk. "I mean I'm not wanting to be with her and glad it's over with- with her and- I'm just going to stop talking now," I laughed, covering my mouth.

Justin smiled, his red cheeks being the only thing giving away his inebriation. "You're cute when you're drunk," he said.

I stood and immediately had to brace myself on the bed in front of me as I felt the wine spin inside me. "I'm not- okay maybe I'm a little tipsy," I giggled as I staggered a step closer to Justin, who put his feet down, making room for me between his legs. I braced myself on the arms of his chair as I leaned in. The long line of my cleavage dangled in his face as my hair draped to the sides of his cheeks. "I may be a little drunk," I whispered, kissing the right side of his neck. "But I think I can still show you my appreciation for what you did for me." Kissing the other side of his neck, my plush lips slowly and gently pressed and dragged down his neck. My hand rested on his thigh and rubbed up and down slowly as I cooed in his ear.

Justin allowed my hand to stay on his thigh and cupped my neck, holding my lips to his neck for a moment as I kissed and sucked light hickies on him slowly before he pulled back. "You owe me nothing," Justin said, staring into my eyes only inches from his face. "You can walk out that door and forget all this ever happened. You are the one who has ultimate control over all this. All you have to say is, 'No.' Do you understand?"

"And what happens if I say, 'fuck me, Daddy?'" I said with a devious grin.

Justin pulled my lips to his kissing me deep and hard. I instantly released a high-pitched moan into his mouth. I tasted what remained of the cabernet on his tongue as it swirled with mine. My fingers subconsciously rubbed on the crotch of his jeans; I felt the bulge growing inside. When we finally broke the messy kiss, I realized I was half sitting on his lap. His hand was cupping my ass through my skirt and his lips moved to my neck. He kissed and sucked down the length of my neck to my cleavage. He roughly pulled my left breast from my dress and I felt his warm, wet lips close around my nipple. Sucking so hard, I had to gasp and cry out into the top of his head. As I squirmed in his lap my skirt stretched and inched above my bare ass cheeks. Justin's hand quickly seized the opportunity to slide down my ass crack and between the tender skin of my thighs. As his fingertips kissed my already moist pussy lips, I gripped his neck, holding his lips tighter to my breast. "Oh fuck, sir..." I cried out needing more.

Lost in the moment with my eyes closed, I hadn't even realized my hand was wrapped around Justin's hard, tender cock until I heard him release guttural groans into my stretched breast. My hand was gentle but firm on his shaft. Squeezing as I pressed to the base, then pulled to the tip and repeated. His fingers began to dart in and out of my pussy and my quivering thighs rocked on his lap as I felt the wetness drip down my leg. As I curled into a tighter ball in his lap and thought I could stay in this position for hours, I was abruptly lifted into the air and scrambled to grasp Justin's neck.