Late Night Confessions: A Steamy Older Man Younger Woman Romance

by Mia Madison

  If I'd met a good guy and become his girlfriend, I wouldn’t be in this situation now. But though I’d dated a little—mostly blind dates my friends set me up on—I’d never had a real boyfriend. And I wasn’t entirely certain why. But I could be kind of shy, especially since I’d spent the last decade being the youngest one in my class. And some semesters when I got involved heavily in schoolwork, I could go months on end without going to any parties or social events. I was an introvert, born and raised.

  TJ: Did you fall asleep on me?

  A sudden image entered my mind, TJ and me on a bed, my head resting on his bare chest as we both panted, spent and satisfied. I didn’t have the slightest clue what he looked like, but that didn't stop me from wondering—and from thinking how good it would feel to be in his arms. And then I had a sudden pang of guilt. I was supposed to be thinking about being in Andy’s arms. Not some man who was all but a stranger.

  Except TJ didn’t feel like a stranger anymore.

  MB: Just thinking.

  TJ: That’s good. I try to do that at least once a day.

  MB: I guess… I can’t really explain it. But I’ve made my decision.

  TJ: OK.

  I frowned at the computer screen. I was a grown woman. I didn’t need his approval. But somehow, the nagging suspicion that I didn’t have it bothered me.

  MB: You think it’s a bad idea.

  TJ: Hey, I’m a guy. Guys never think that sex is a bad idea.

  MB: So you shouldn’t have a problem with it.

  TJ: Agreed. I don’t have a problem with it.

  MB: Good.

  TJ: But I think you do.

  What? He didn’t know me. We’d only met tonight. But then I looked at the clock… it was only half an hour until sunrise. So technically we’d known each other for two days, Saturday and today. Not sure why that made me feel this chat was more legitimate, but at that point in the morning, my brain was pretty fuzzy.

  MB: I shouldn’t. It’s simple, really. You have a problem, you find a solution. I’m still a virgin—the solution is pretty obvious.

  TJ: That’s a very clinical way of looking at it. Or cynical.

  MB: No, it’s not. I want to do this.

  TJ: With him?

  MB: With someone.

  I’d typed the words and pressed SEND before I really considered them. Maybe I was doing this for the wrong reasons. But on the other hand, how could anything with Andy be wrong? He was a great guy. I tried to explain that to TJ. He’s my friend.

  TJ: So go to the movies with him.

  MB: I do.

  TJ: Good. Movies and sex. Plenty of friendships are based on that.

  MB: But?

  TJ: But is it what you want for your first time?

  MB: It’s my only option.

  TJ: No, it’s not. You can wait for something real.

  MB: I have been waiting. Many, many years. And it hasn’t happened yet.

  Suddenly, I was angry. Didn’t he think I’d been over all this a hundred times?

  TJ: Just because you haven’t had a real relationship yet doesn't mean it won’t happen.

  MB: When? When I’m thirty? Forty? Fifty? I’m 22, and I’m supposed to be going after life with everything I’ve got. Sure, I’d like my first time to be with someone I’m madly, passionately in love with. Someone I have an intense connection with. But who knows when that’ll happen—if ever?

  TJ: It’ll happen. And when the real thing comes your way, you might be happy that you waited.

  Pretty hypocritical words from a guy who just said that sex is never a bad idea. You keep saying “real”. But nothing’s real anymore. Everything’s virtual. Social media. Twitter. Facebook. None of that’s real, yet people spend half their day on that stuff. Nothing’s real anymore.

  TJ: I am.

  MB: Maybe. But you could be a sixteen-year-old kid, for all I know. Or an eighty-year-old woman.

  TJ: Are those my only two choices?

  My eyes rolled even as I laughed. He had no right to make me laugh when I was mad at him. Except I knew it wasn’t really him I was mad at. Everything he was saying was stuff I’d thought about, too. And worried about. But I’d made up my mind, and I didn’t need him making me question myself.

  MB: I’m just saying, very few things are real in this world.

  TJ: Fair enough. Check your inbox.

  What? I looked up at the corner of the screen, and sure enough, I had a message. A message with a picture. I stared at the little icon for a few seconds before returning my gaze to the chat window.

  MB: If you sent a dick pic, just FYI, most guys lead off with that.

  TJ: That actually made me laugh out loud. Believe me, I’m well aware that my fellow males are not the most original online correspondents. But my message is safe. You can open it.

  MB: What is it?

  TJ: Something real. And now, my dear, though I’ve truly enjoyed our chat, I have to hit the sack or I’m going to sleep the entire day away.

  MB: Me too.

  My tired mind was momentarily distracted from wondering what he’d sent to thinking about how much I didn’t want our conversation to end. But he was right, it was time.

  MB: This probably sounds dumb after our marathon chat, but it was nice to meet you.

  TJ: Nice to meet you too, Miss MayBee. Sleep well, lovely lady.

  MB: You too.

  The minute the chat window said that he was offline, I clicked over to the mailbox and opened his message. It was short: Some things are real. And they’re worth the wait.

  Blinking at it, I let the words settle into my mind. Maybe I could try harder to find a real boyfriend after I lost my virginity tomorrow night—actually, since it was Sunday now, that meant my date with Andy was tonight. That thought made me nervous enough to have to try twice to click open the attachment TJ had sent.

  On the screen in front of me was a picture of a man. And incredibly handsome man with dark wavy hair and piercing blue eyes. Sexy, scruffy whiskers adorned his jawline. And that grin on his face… I’d never used these words to describe anything in my life, but his grin could only be described as panty-melting.

  That couldn’t be TJ—could it? I mean, the age was about right. The man looked like he could be thirty-six. His hair was dark, but there were a few strands of grey in it, especially near his temples. So the age fit, but the man in the picture was just too good-looking. He had on a long-sleeve t-shirt, but I could see muscles straining the material covering his upper arms.

  No way. First off, people didn’t send their real pictures on anonymous websites for scandalous confessions. And secondly, that just couldn’t be the man I’d been talking to the whole evening. No way in hell. But then I squinted at the screen. The gorgeous, god-like man had a post it note clasped in one hand. I’d been so busy looking at the rest of him, I hadn’t noticed it before.

  Enlarging the picture on my screen, I looked at the note and gasped. Handwritten words were scrawled on the note.

  “MayBee, I’m real.”

  It really was him. It had to be, he’d spelled “MayBee” the way I did in my screen name, MayBee3. Oh my God. I’d spent the whole night talking to a man who looked like that? It didn’t seem possible. He’d seemed so normal when we chatted. Well… except for being funnier and more interesting and a better conversationalist than pretty much anyone else I knew. But he certainly hadn’t sounded like he looked like that.

  Which didn’t make any sense. I guess it really was time to go to sleep. After all, I had a big night to plan for. But before I shutdown my computer, I transferred TJ’s picture to my phone. And before I went to sleep, I looked at it a half a dozen more times.

  Maya

  “I want to do this,” I said out loud. Not to Andy—I was still in the car driving over to his place. So great, now I was talking to myself. That couldn’t be a good sign. But maybe it was a good thing. Maybe after I lost my virginity, I’d want to tell myself all about it on the ride home.

  My mi
nd was racing, but luckily, my old Nissan knew the way to Andy’s apartment very well. I usually hung out with him a few times per month. We’d been friends for years, and even when school got insanely busy, I made time for him.

  But this time was different. This time we were going to be friends with benefits. That was an entirely different kind of friendship. Sure, Andy flirted with me from time to time. Teased me about what a proper young woman I was, never giving into his charms.

  Once or twice over the years, we’d taken the flirting a bit farther. I’d never been the party every Friday night type, but I’d attended a few events with Andy. Once, while drinking out by a pool, Andy and I had kissed a time or two, his hands tentatively roaming across my back, then squeezing my ass. But we’d both known it was a momentary whim due to alcohol, not romantic affection.

  Andy was a good friend, and I loved him like a friend, but there was no way it was ever going to lead to anything more. Suddenly, I recalled TJ’s words, and a shiver of unease went through me. What was it he’d said? Being in love means that your heart beats faster when you think of them. It means you can’t stay away from them.

  But it was okay. I knew that this wasn’t a happily ever after situation, and I accepted that. This was a friend helping me gain some experience. A very specific experience that everyone else around me had already had. But then TJ’s words popped into my head again. That’s a very clinical way of looking at it. Or cynical. I’d never heard his voice, but somehow, I could imagine a deep, rich, cultured voice saying those words.

  Without realizing it, I missed the turn to Andy’s street. Great. Now I’d have to make a difficult left to get back. Or maybe I could just drive down to Main Street and then take Third Avenue. It would only take another ten minutes.

  Once I was back on track, there was a parking space right in front of Andy’s apartment building, but I drove slowly past it. Which was stupid. What good would having to walk farther do me? It’s not like burning an extra thirteen calories would make me look better naked.

  Oh God, I was going to be naked in front of Andy. That was going to be so awkward. But he was a good guy. He’d make me feel comfortable. He’d keep things casual and humorous.

  I thought about my word choices. Comfortable. Casual. Humorous. Those words were the polar opposite of the things I’d told TJ I wanted. Passion. Intensity. Connection.

  What the hell was I doing? TJ was right, this was much too important to be treated like an item on a To Do list:

  Graduate from college… check.

  Get accepted to grad school… check.

  Become a teaching assistant… check.

  Lose virginity to friend…

  Oh God, I couldn’t do this. Blindly, I pulled into a parking space at the end of the street. Tears leaked from the corners of my eyes, and try as I might, I couldn’t quite identify why. Disappointment? No, not really. If anything, I felt a little relief. TJ was right, I deserved more than this. My first time should be real.

  Gradually, the salty tears stopped dripping down my cheeks. I texted Andy, and he immediately texted back that he understood. He really was a good friend, but that wasn’t enough for me anymore. I wanted something real. Someone real. Someone who loved me. Someone in love with me—and someone I was in love with in return.

  For perhaps the hundredth time today, I swiped open my phone and looked at TJ’s amazing picture. If men like him were really out there, I shouldn’t settle for a first time that wasn’t the real thing.

  Maya

  “Damn!”

  Unlike the rest of the world, I didn’t harbor a hatred for Monday mornings. I loved being in graduate school. I loved the classes I took and the one I taught.

  But today felt different. It was ironic. Forty-eight hours ago, I would have thought that I’d feel different on Monday morning because I’d had sex. Never would I have guessed that I’d feel different because I hadn’t had sex.

  When I’d gotten back home last night, I’d felt exhausted. The lack of sleep the night before definitely had taken its toll, but that was only part of it. It just felt like it had been a whirlwind of emotions. Chatting for so long with TJ. Feeling like I could talk to him about anything. Then going to sleep at five o’clock in the morning was disorienting. After that, it was a mad scramble to shower, shave, moisturize, and do anything else I could think of to be physically prepared for sex. But mentally I wasn’t prepared at all. Making the decision not to go through with it had taken a lot out of me. When I got home, I collapsed into bed, exhausted but unable to sleep.

  Now it was a new day. A new start. I was eager to get to the university. Though my four years of college had been marked by a lot of insecurity and introversion, graduate school seemed to agree with me. Majoring in English was a natural fit for me since I loved to read and write. Most Mondays I was the first one in the graduate teaching assistant office. But today, there was something I needed to do first.

  The CUNFESHUNZ website was pretty empty when I logged in. Clearly, it was more of a late night kind of place, not a morning one. A stab of disappointment rocked through me when I checked for TJbard—he wasn’t online. And no new messages in my inbox, either.

  Perhaps that wasn’t too surprising. He probably didn’t want to bother me on my big night. Despite what he’d said about not having a problem with my plan, it seemed like he had. Which should be infuriating. It was none of his business. But instead, it felt to me as if he cared. And that made me feel good in spite of myself.

  Since there was no new message from him, I clicked open his other one and looked at his picture again. He was certainly easy to look at. There was something about his grin that looked somehow both friendly and hot. There was something about his eyes that looked amused and intelligent. Maybe I was infusing qualities based on our long conversation, but the more I looked at his photo, the more I thought it matched his personality.

  I still couldn’t believe he’d sent a real picture. Who did that from a website that values anonymity above anything else? But he’d done that for me. That gesture more than anything had gotten me to reconsider yesterday.

  My hands moved on their own accord, smoothing back my wavy chestnut hair. I sat up straighter. I smiled into the built-in camera at the top of my desktop. And before I could think too much about whether it was wise or not, I took a picture. Then another. Then another.

  The second one was the best, so I attached it to a message to TJ. Inside the body of the message, I wrote: Still a virgin.

  And then I pressed SEND, my heart pounding with excitement. What would he think of that? What would he think of me?

  I was pretty sure I wasn’t going to think of anything else except him all day.

  Maya

  “Good morning, everyone.”

  At the sound of the unfamiliar feminine voice, I looked up from the conference table. My friend Tracy exchanged glances with me. Why was Dr. Harper, the head of the English Department, at one of our twice-a-week graduate teaching assistant meeting? That had never happened before.

  “I’m afraid I have some bad news,” Dr. Harper continued, and I braced myself, wondering what it could be. “Dr. White’s husband had a stroke over the weekend—a bad one. Carolyn’s taken a leave of absence for the rest of the semester so that she can assist with his care.”

  Murmurs from my fellow TAs greeted this news. I’d never met our advisor’s husband, but I felt bad for him, just the same. And for her. Carolyn White was a dedicated professional who had helped the six of us overcome our fears this semester. She’d guided us all to become more comfortable in the classroom.

  “That’s horrible. We’ll have to send flowers,” Tracy said, and the rest of us nodded.

  “Who’s going to be our new advisor?” Sandy asked. She’d voiced the question that had popped into my mind right away, too. The Rhetoric and Composition Division of the Department of English was rather small. Most professors had full schedules between their own teaching and their research duties.

 
; “We’re going to try something different for the rest of the semester. We’ve asked a member of the Comparative Literature Department to take on the mentorship of this group.”

  “But we teach Freshman Composition, not Shakespeare!” Chris, the TA sitting to my right seemed to immediately regret his outburst in front of the head of the department, but she just smiled.

  “Dr. Jenson is an excellent writer and is more than capable of steering you along the path that Carolyn has started you on. He’s eager to work with you, and should be here shortly—ah, here he comes now.”

  Dr. Harper looked down the hallway, as the six of us stared at each other, shrugging. This was the first semester of graduate school for all of us except Chris, and it appeared that no one had yet taken a class by this Dr. Jenson. Tracy raised both eyebrows at me, a definite “we’ll see” gesture.

  And then Dr. Harper said, “Welcome, Thomas.” A tall man with dark hair entered the conference room.

  Tracy turned, took one look at him, and then turned back at me, grinning broadly. But I barely noticed. I couldn’t tear my eyes away from professor who was currently sitting down at the head of the table. At his vivid blue eyes. At his dark, glossy hair. At the short beard adorning his cheeks. At the muscles evident even under his shirt and suit jacket.

  My mind was a swirling race of jumbled thoughts. This couldn’t be happening. It couldn’t be possible.

  Dr. Thomas Jenson just couldn’t end up being the man I’d spent a whole evening talking to about my lack of a sex life.

  Yet it was true.

  My new advisor was TJ.

  “Do you want to grab some lunch, Maya. Maya? Are you okay?”

  The meeting was over, and Tracy and I were the only ones left in the room. With great effort, I turned my attention to her. “What?”