Late Night Confessions: A Steamy Older Man Younger Woman Romance

by Mia Madison

  TJ: And when I’ve licked your fingers clean, I push you back on the bed, climbing on top of you. And I pin your hands above your head, pressing them against the mattress as I kiss you. You beg me to take you, to push inside of you, but I want to see if I can get you even more frenzied first. I want you to beg for my cock to push inside of you, fill you, make you come so hard you burst into a million pieces.

  Good God. My breathing was fast and I’d practically melted into a puddle on my desk chair. I closed my eyes and could picture him hovering above me, teasing me, driving me crazy. I could almost feel his weight on me, his thighs spreading mine open. Heat pooled between my legs as I imagined the tip of his cock right at my entrance, ready to thrust inside me. But that’s where my imagination failed me. I didn’t know what that felt like, but I sure wanted to.

  After a moment—or a minute—or more, I opened my eyes.

  TJ: Still with me?

  MB: I *think* so.

  TJ: I was afraid I’d scared you off.

  MB: What if you did the opposite?

  TJ: Good question. I guess that's better for my ego, worse for our situation.

  That made me roll my eyes even as I tried to catch my breath. Good thing we didn’t cross any lines or anything like that.

  TJ: What lines? We’re just two friends online who have no connection offline. I don’t meet a lot of lovely young ladies in my work as a silversmith.

  MB: You said you were a blacksmith.

  It was fun to flirt with him, but my body wanted so much more. Touch. Scent. Taste. Sound. Not just words on the screen.

  TJ: I took a class at the community college to upgrade my skill set.

  Despite the fact that I was dying to hear more sexy words from him, I had to laugh at that. The local community college was a decent school as far as two-year institutions went, but their selection of classes left something to be desired.

  MB: Smart move. I hear that silversmiths are much more in demand.

  TJ: What about you? What do you do for a living?

  MB: I’m a paranormal investigator.

  TJ: So you’re a ghostbuster?

  MB: We don’t like that term.

  TJ: My bad.

  I sighed. Actually, you sound pretty good. What you said before, I mean.

  TJ: I hadn’t really meant to go there.

  MB: Then why did you?

  TJ: Not sure. But it feels like I can talk to you about anything. It felt like that last weekend, too.

  MB: I know. It’s like that for me, too.

  TJ: So… can we do this?

  MB: Do what?

  TJ: Be professional colleagues by day? And anonymous, flirtatious, talk-about-anything, the-dirtier-the-better friends at night?

  MB: I honestly don’t know.

  TJ: It’s not a good idea.

  MB: No, it’s not.

  TJ: Things could get complicated if we’re not super careful to keep the roles separate.

  MB: Yes, they could.

  TJ: Do you want to do it anyway?

  Still slumped in the chair, my mind raced. TJ was offering two options. Only see his professional side at work, or also get to enjoy his fun, naughty side at home. My mind, my body, and my hormones didn’t have to think very long about that at all.

  MB: Hell yes!

  TJ

  What the hell was I doing?

  That thought crossed my mind about twenty times the next day. I taught in the morning, so now, mid-afternoon, I was in my office, supposedly doing research for a paper I was writing. But instead, I was attempting to figure out my own fucked up thought process last night.

  She was a graduate student. She was my advisee. She was a virgin, for Christ’s sake. Three excellent reasons not to share sexual fantasies with her. Yet I hadn’t been able to resist.

  And that baffled me, too. I wasn’t perfect, but impulse control wasn’t one of my weaknesses—until now, apparently. Never before had I spoken that way to a student. I’d never even come close to crossing a line with the graduate teaching assistants who sometimes co-taught with me. Even the shameless ones, the you women—and the occasional young man—who showed up during my office hours pretending they had some pressing issue that was completely made up. As if I couldn’t tell a sincere student from a horny one.

  I’d never once been improper with a student. Ever. I dated, sure. I fucked, yes. But not my coworkers. Not my students.

  Sure, Maya wasn’t my student. But she was a student. And twenty-two. My impure thoughts about her were wrong on so many levels. There was the age difference. The experience difference. And most importantly, there was the fact that thanks to Carolyn White’s family emergency, I was now Maya’s advisor.

  Briefly, I wondered what would have happened if I hadn’t had to take over for Carolyn. Would Maya and I have kept chatting online in the evenings? Probably. That all-night chat that first weekend had been so… I wasn’t even sure of the word for how much fun it had been. How intimate it had felt. Some English professor I was. But somehow it had woken something up inside me. Something that had been dormant for a long time. Lust? No, that flared up all the time. Excitement? That happened sometimes. Not recently.

  It sounded corny, but the word that seemed to fit best was hope. Talking to Maya, opening up to her, it had made me feel hopeful. Optimistic. That someday I might feel the connection that I’d lacked with my ex-wife.

  It had been stupid for us to get married so young. But we’d had sex, we’d been dating for a while, we graduated, and it seemed like the thing to do. I know that sounded fucked up, but that was pretty much my thought process at the time. I’d been only a little older than Maya, and a lot less mature.

  She’s show more wisdom and good sense when I’d told her about my failed marriage during our chat than I had the entire eighteen months I was married. Maya hadn’t judged when I said I’d never been in love. She’d been sympathetic. Insightful.

  Now I’d repaid her kindness in listening to me by pressing her about her fantasies. And sharing mine with her. With a virgin. But she wasn’t a complete innocent who knew nothing about sex. She knew enough to suspect what kinds of things she’d enjoy. Being pinned down. Being overpowered. Being taken.

  Even now, thinking about the things she’d said made my cock twitch. Her interests and mine seemed perfect. Two sides of the same coin. I couldn’t help but think that if we’d met under different circumstances, we might be pretty damn perfect for each other.

  But I needed to stifle those kinds of thoughts because it was almost time to see her. Her and the other TAs. They were all bright, eager young instructors. I enjoyed working with them more than I thought I would. But the thought of seeing Maya right now at the meeting was painful. Being near her in person and knowing that I could never talk to her the way I did last night online was an exercise in frustration. And disappointment.

  So yeah… I sorely needed my legendary impulse control more than ever, but it had been nowhere in sight last night. But I’d sure as hell better muster it up for today. I’d worked very hard to get to this point in my career, and I didn’t want to risk it. But more than that, I didn’t want to doom her career when it was just barely getting started. I had a feeling it was going to be a pretty damn spectacular one.

  The TA meeting started off well. Maya sat next to her friend Tracy, as she always did. We exchanged polite, professional smiles when I came in. That was okay, wasn’t it? I sat at the head of the table and mostly listened. Midterm grades were due next week, and the TAs took turns talking about what they’d been doing in class. Chris, a bright young man who was in his last semester, talked the most.

  “I just can’t seem to get through to her, Dr. Jenson,” he said.

  “Call me Thomas.” I’d said that to them before, but they all insisted on Doctor or Professor. Except when Maya had called me TJ last night during our chat. But probably best not to think about that right now.

  “I know she can do better, but she’s just not applying herself. I’
ve tried everything to get her to focus more on her writing,” Chris continued.

  “You can lead a horse to water, but you can’t make her drink.” Not that I usually spoke in trite clichés, but I’d been watching Maya out of the corner or my eye, and she was biting on the end of her pen. The sight of her full, pink lips closing around the pen made me catch my breath. How I’d love to feel those lips on mine—or my cock—or really, any part of me. I wanted to touch her so badly it was almost painful.

  “So should I give her the higher grade?”

  “Sorry?” Clearly, I had missed something. Maya was looking at me curiously now, which wasn’t helping.

  “I said, if I cut off the midterm grades from Monday, then she’ll get 69 percent, a D minus. But if I count the grades through this Friday, she’ll likely squeak by with a D.” He consulted the papers in front of him. “Yeah, if she turns in the next draft on time, she’ll get a 71 percent. So what should I do?”

  I thought about it for a minute. He was thinking about what was best for his students—that was a sign of a good teacher. Probably I shouldn’t analyze what kind of teacher I was being since I felt my pants tighten every time Maya shifted in her seat, making her breasts bounce lightly. “You can do either as long as you’re consistent with the other students. So, whenever you cut off the midterm grades for her, you’ll have to do the same for the other students.”

  “Okay, but which do you think is better? Giving her the 71 percent so that she’ll have some hope of a higher grade at the end of the semester? Or using the 69 percent as a wake-up call? Maybe it’ll motivate her to try harder.”

  Using one of the oldest teacher tricks in the book, I said, “What do you all think?”

  Two students voted for giving her the higher grade, but Sandy disagreed. “69 is the best. Definitely. It’ll be a shock to the system. Maybe get her to move her ass. Definitely do the 69.”

  I fought the urge to laugh. What was I, fourteen? But Maya looked amused, too. Somehow, it was encouraging that her mind was in the gutter, too. I asked her what she thought.

  She was silent for a long moment, her eyes on mine. “I think I’d probably try a 69.”

  I arched an eyebrow at her. She returned my stare for a few moments before a flush graced her face and she looked away.

  “Good to know,” I said.

  TJ: So, you're interested in trying 69?

  MB: I had a feeling you were going to bring that up.

  TJ: You know me too well already.

  It was eleven at night, and I’d spent half the evening grading papers and the other half trying to resist finding her online at CUNFESHUNZ. Obviously, it had been a losing battle.

  MB: That was pretty damn funny when everyone kept mentioning it during the meeting.

  TJ: I know!

  MB: Afterwards, I ducked into the restroom and laughed my head off.

  That made me grin. Somehow, the idea of her losing control turned me on, whether it was her writhing with pleasure, screaming my name, or even just giggling uncontrollably. An image of me tickling her and making her laugh entered my mind and my balls ached with longing.

  TJ: Do you think you’d like it?

  MB: I don’t know. Do you? I assume you’ve tried it.

  TJ: Of course. It’s one of my favorites.

  MB: It seems like men really like it.

  TJ: And you think that women don’t?

  MB: Well, I don’t know. It’s not like I can poll my friends about this. I’d definitely be willing to try it, but it seems like… sort of… multitasking.

  That nearly made me spit out the Merlot I’d just sipped. Multitasking? It’s a sex act, not a To-Do list.

  MB: I know.

  I was pretty sure she was blushing now, and it made me long to see her face.

  MB: But, well, the first time I… do that… to a guy. I want to give it my full attention. Do my very best to make him feel amazing.

  TJ: I’m sure he would.

  And just like that, I imaged the nameless, faceless guy who would pop her cherry. Who would first feel her lips wrapped around his embarrassingly small dick. I hated that guy for being able to move in where I couldn’t. He didn’t deserve her, whoever he was. She deserved someone special.

  TJ: And what about the other part of it? The guy going down on you? I presume you’ve never experienced that?

  MB: Of course not.

  TJ: Do you think about it ever?

  MB: Sometimes.

  TJ: Are you blushing now?

  MB: I usually am when I talk with you.

  TJ: Good.

  MB: Why is it good?

  TJ: Because I don’t get to touch you. I don’t get to be with you. This is the only way I can have any effect on you at all.

  MB: If it makes you feel any better, you do have an effect on me. I was squirming in my chair all during that meeting today.

  TJ: What meeting are you referring to? Were you at the Council of Silversmiths this afternoon?

  MB: Yes. It was a slow day for ghostbusting.

  I laughed. She really was a charming young woman. But she hadn’t answered the questions. Do you dream about a man’s head between your thighs? His face buried in your pussy? His tongue flicking back and forth, his fingers pushing into you, easing you open?

  MB: Holy crap.

  TJ: I’ll take that as a yes.

  MB: Yes, it’s a yes.

  TJ: Do you think you’d like it?

  MB: When you put it that way, definitely. But I think I’d also worry about it a little. You know, to have his face right there in such an intimate place.

  TJ: I think most women worry about that from time to time. But a man who knows what he’s doing will make you feel relaxed first. I’d start by massaging your shoulders, or your head and neck. I give a world class scalp massage.

  The thought of feeling her silky bronze tresses sliding through my fingers as I made her luscious body relax, one muscle at a time, was intoxicating. Far more so than the Merlot.

  MB: Sounds heavenly.

  TJ: It is. And once you were relaxed, my fingers would move to your breasts, squeezing, cupping, tugging. Then I’d capture your nipples in my mouth, and by the time I kissed my way down your body, you’d be begging for me to touch your clit.

  MB: Ooo, that’s hot. Getting so worked up that I’d beg for your touch.

  TJ: I could get you that worked up.

  I knew that with 100 percent certainty. And apparently, she did too.

  MB: I believe it. I, umm… I fantasize about it.

  TJ: Me too, sweetheart.

  There was silence for a minute. According to the private message window, she wasn’t typing anything.

  TJ: You still there?

  MB: Yeah. It’s just… when you call me something like that, sweetheart, it makes me wish our situation was different. That maybe… there was a chance for something more.

  TJ: I wish that, too.

  She had no idea how much that was true.

  Maya

  TJ: Pssst… what are you wearing?

  I grinned. He’d just seen me thirty minutes ago. We’d passed in the hallway downstairs when I went to make some copies.

  It was the last week in November. Last week I’d flown to Ohio to be with my parents for Thanksgiving. During that time, TJ and I had taken to texting through the CUNFESHUNZ private message feature on the phone app during the day. Now that we were back at work, we’d continued the habit.

  So far, we usually saved our most risqué conversations for our evening chats, but it was kind of fun to hear from him during the day. Especially after seeing how handsome he looked today. He’d been wearing black pants and a white dress shirt open at the neck. He looked super hot, unlike my fellow students who usually dressed down. I’d take a guy in a white dress shirt over a dude in flannel any day of the week.

  How I wished I could take TJ—or better yet, that he could take me.

  MB: My ghostbuster coveralls.

  TJ: I bet you could mak
e even that look sexy. Does it have a zipper in the front? How low is it unzipped?

  MB: Almost all the way down to my—oh wait, we’re supposed to be good during the day.

  TJ: Tease!

  MB: Well, you’re the one who is always saying we should be good.

  TJ: You must have misunderstood me. I said that I *am* good. In bed. And with my head between your—

  MB: Don’t worry, I believe you.

  TJ: Are you sure? Because I could give you more details. Describe a few scenarios for you.

  MB: Can I take a raincheck on that? And hear about it tonight?

  TJ: It’s a date.

  Date. Interesting word choice. Our chats in the evening weren’t dates, but I sure as hell wished they were.

  For most of my adult life, I’d struggled with meeting a good man. I never envisioned that I’d meet one and not be able to be with him. It was just so against the rules. I was grateful to be able to teach in the English Department. I was learning so much, and I knew I couldn’t jeopardize that. But sometimes I wished I could just say screw it and then go screw him.

  Every time I saw him at work, I ached for him. He was so damn good-looking. Even Tracy mentioned it all the time, and she had a boyfriend. And at night online, TJ’s hot and sexy words worked me into a frenzy. I wanted him with every fiber of my being.

  But it was more than a physical desire. Chatting with him was the highlight of my day. He was smart and funny. Yes, I liked it when he flirted and teased, but I loved it when we talked about other things, too. About anything, really. He was so easy to talk to. Such a good listener. Too bad I couldn’t just spend all my time reading his messages instead of the literature I was behind on reading for the classes I was taking.

  So yeah, I was a bit behind on my own classwork, not to mention my grading, but I was having so much fun. I couldn’t ever remember being this excited about anyone.

  Maya

  “Are you nervous?” Tracy asked.

  “Yes,” I said, truthfully.