Late Night Confessions: A Steamy Older Man Younger Woman Romance

by Mia Madison

  Her eyes closed and her breasts bounced as she writhed in response to my words.

  “Do you think anyone on that website would believe your confession if they saw you right now? Saw how badly you wanted to come? Saw how much you wanted my big, hard cock filling you up?

  “Oh please,” she whimpered, and I could see the need on her face. I loved having her at my mercy like this… and I know she loved it, too.

  “How many times have you thought about me making you come? Making you scream?” I flicked against her clit faster, my finger sliding easily around her wet folds.

  “Every night,” she said, her voice hoarse and strained.

  “This is what you dreamed of, right, baby? Being pinned under me? Being controlled by me?”

  “Oh yes.”

  “Being forced to come hard?”

  “God yes.”

  “Then hold on… you can’t scream, but you can moan and show me how good you feel.”

  She nodded frantically, her eyes squeezed shut. And I pushed an inch inside her tight, virgin channel, and rubbed her clit, hard. Her body jolted, her perfect tits thrusting into the air as her back arched.

  Maya opened her mouth and I could tell she was going to scream, so I leaned over her, closing my mouth around hers, taking her cries into my mouth. Now I could feel her body trembling under mine as she came, her wrists jerking in my hand, her thighs closing around my fingers.

  “That’s it, baby,” I whispered when it seemed she was beyond screaming. “Ride it out, gorgeous.”

  She’d looked so fucking hot as she came. I’d envisioned it a hundred times since our first chat, but the real thing was way better than I imagined.

  My cock was steel-hard and throbbing, but this was about her. This was helping her release the passion I’d always known was inside her.

  And even without coming, this was one of the hottest encounters I’d ever had.

  “Good girl,” I whispered as she came down from her orgasm. “You came so hard for me… such a good girl.”

  I released her wrists and pulled her up against me, her head resting on my chest as her breathing gradually slowed. I stroked her hair and ran my hands up and down her back.

  This felt so fucking right. I didn’t know why, or how it could work, but it felt right. It felt like something I’d been missing for a long time.

  And despite the risks, despite the rules, there was no way in hell I was giving her up now.

  Maya

  TJ: So, how was your day?

  A smile crossed my face as soon as I saw TJ’s words. In the week since our encounter in his office, we’d met every night online at ten. By mutual agreement, we’d chosen not to look for each other earlier so that we could get our grading done. Plus, I had things to do for the classes I was taking. But then at quarter till each night, I’d put that away, slip into something comfortable, and go to CUNFESHUNZ and wait to hear from him.

  MB: Pretty uneventful.

  My grin widened as I waited for his response.

  TJ: Oh really. Nothing out of the ordinary?

  I could picture him with one eyebrow raised. It was a very sexy look on him. Of course, I’d never seen him not look sexy, including today when I got to see his orgasm face when he came in my mouth.

  MB: Not really. I went to the library. Did some studying.

  TJ: Did you do anything else while you were there?

  I wanted to be a smartass and say “you” but it was more fun to draw this out. Umm… oh yeah, I talked to an old friend.

  TJ: Watch who you’re calling old, young lady.

  God, it was fun to tease him.

  TJ: What did you and this “old” friend do?

  MB: We studied.

  TJ: Did you really?

  MB: Well, the little room we were in was called a study room, so we must have.

  TJ: If they really wanted people to study in them, they wouldn’t have provided locks on the door.

  MB: I’m sure glad they did, though.

  TJ: Me too!

  MB: Although I’d say I did some studying. Or, at least, I learned something new today.

  TJ: You were an excellent student.

  MB: You were a good teacher.

  TJ: Glad you think so. If you ever feel you want to practice your new oral skills, just say the word.

  MB: Funny!

  TJ: Sometimes. But seriously, it felt amazing.

  MB: It’ll feel even better next time.

  TJ: Hold on, let me look up how late the library is open.

  That made me laugh. This past week had been so much fun. It had involved a lot of sneaking around, but that had made it even more exciting. Every day except Tuesday, when he taught an extra class, we’d managed to find at least a little time to be together. Just brief moments, but it was wonderful. I’d never dreamed I’d get to do any of those things with a man like TJ.

  Today, when I’d gone down on him, I’d been a little nervous, of course. But even though it was my idea, even though it was something I’d been longing to try with him, he made sure I was comfortable with what was happening every step of the way.

  And when he groaned deep in his throat, his fingers tightening on my shoulders, his cock spasming in my mouth, I’d felt like a million bucks. I’d made him feel that good. I’d made him lose control like that. Me. A virgin who’d never even had a real boyfriend. Now I had a real man in my life, and it was even better than I thought it would be.

  It wasn’t just the sexual things, either. We’d managed to have a quick lunch together twice. The university was so big that there were cafeterias, coffee houses, and snack bars everywhere. Once we’d eaten in a small cafe in the basement of the Genomic Biology building. Not a lot of English faculty or staff made it over to that part of campus.

  And our chats at night were the highlights of my evening. We were still able to talk about anything and everything. I’d shared more of my thoughts, secrets, hopes, and dreams with TJ in the last two weeks than I had to Andy, Tracy, and all my friends in college combined.

  TJ shared a lot with me, too. Sometimes, either in person or online, he seemed a bit bemused by how much he talked with me. About his past. About his short marriage all those years ago. About the path he took to get where he was in the university today. I got the feeling that he hadn’t opened up to anyone like this in a long time, either.

  Now, when I read the confessions posted at the website, I had no desire to post another one of my own. TJ was my secret. My wonderful secret that made me so happy. Each morning getting dressed to go to the university, I chose my clothes which such care, knowing I’d see him.

  And during the TA meetings, it was so much fun to watch him in his professional mode. To see him interact with the others and to know they had no idea about us. Not even Tracy. I felt bad not telling her. I knew she wouldn’t betray our secret and get TJ and me in trouble, but we’d decided it was safest not to tell anyone. Sometimes I felt a little guilt at keeping this from her, but for the time being, I was thrilled with this sexy, exciting relationship that made me so happy.

  Every day was more fun than the last—until the first Thursday in December.

  TJ

  “You've got a really great start here, but you need to go deeper. Get to the heart of what the story’s really about. Revise your analysis and let’s meet again in a week to go over your presentation strategy.”

  “Yes, Professor.” The two undergraduates sitting across from me in my office spoke in a chorus. God, they looked so young. Hard to believe they were only a few years younger than Maya. She seemed so mature, so bright. Personable. Maybe I was biased, but she sure seemed like an amazing young woman to me.

  And there she was again. It was the second time today she passed by my office. She already knew I didn’t have time for lunch today, but it was always a pleasure to see her. For one thing, she looked super hot. She’d taken to wearing more skirts, like she had when I’d made her come that first time. Right here on my desk. Pity that it was c
overed in papers and not her sweet, sexy ass.

  Still, even if we couldn’t meet, it was always fun to see her. To exchange a sly wink when I knew she was watching. To give her a knowing grin and see her blush in return. Making her blush was rapidly becoming my favorite hobby.

  But today there was no blush. No secret smile. Just a quick glance and a small, polite nod when she passed. Was something wrong? I had another group of students waiting in the hallway, so there was no time to find out.

  Of course, wondering if there was something wrong was kind of a moot point. Everything we were doing was wrong. I told myself that a dozen times a day. We were risking both our careers, and hers had barely begun.

  It was wrong and the smart thing to do was to stop seeing her until she graduated. But that was a year and a half from now, and there was no way in hell I was waiting that long. I was the mature party. I was supposed to be the voice of reason. I was supposed to do the right thing.

  And I couldn’t. Couldn’t do the right thing, couldn’t stop thinking about her, couldn’t keep my hands off her. Until meeting her, I’d never spent this much time thinking about someone. Counting the minutes until I could see her. Risking it all to touch her. Hell, I’d risk it all just to talk to her.

  At some point, I was going to have to face the music. We couldn’t sneak around for another eighteen months. No way in hell that would work. But I could give it a few more weeks. A few more weeks to enjoy every minute spent with her, online or off. Just for now, I could allow myself this pleasure before thinking too long on the risks. After all, it had taken thirty-six years to find someone whose company I craved this much.

  Later that afternoon, I called the TA meeting to order, determined not to let any of the other graduate students see how I felt about Maya. I forced myself to spend time looking at all of them equally. Speaking to all of them equally. At least that was the plan—but something seemed to be bothering Maya today.

  “How’s your class going?” I asked her.

  “Fine,” she said, but I knew it was an automatic response even before Tracy elbowed her and whispered something to her. “Well… okay, not so fine.”

  For a moment, relief filled me. I’d been afraid that she might be upset about something I’d done. But she was a new teacher, and it wasn’t easy teaching college students. Especially writing. Though it felt like a million years since I’d been a graduate teaching assistant, I still remembered how hard that first year was.

  “I had individual conferences with my students this week.”

  I nodded, trying to encourage her to go on. All of the composition TAs met with their students twice a semester to discuss their papers.

  “And… and I was talking with this one students, pointing out the kind of errors she frequently made in her writing. And… and… I made her cry.”

  Chris let out a bark of laughter, and I glared at him. This was no laughing matter. Maya looked near tears herself as she continued. “She always tries so hard, but she’s just not a very strong writer. Her grammar, in particular, is pretty bad. She took a couple of classes at the community college last year, but I don’t think they helped her much.”

  “Fairview’s English classes suck,” Tracy chimed in. “My brother took one a few years ago. I think his writing ended up being worse afterwards.”

  She wasn’t wrong. For years I’d been disgusted by the lack of attention that reading and writing skills got at the community college across town. As far as I could tell, their vocational classes were pretty solid, but their writing program, such as it was, left a lot to be desired.

  Maya continued on. “I know I’m supposed to just focus on a few kinds of errors with students, and I thought I did—and I also mentioned a few things she was doing fairly well on—but I guess I told her too much. And she was overwhelmed, and she started crying right there in the TA office. I felt awful.”

  God, I wanted to go to her and hug her. Or pick her up in my arms and carry her back to my office and comfort her. But she didn’t need me to be her boyfriend right now—she needed me to be her mentor. Over the years, I’d had more than a handful of students in tears. It was never pleasant, and for a sensitive young woman like Maya, it was clearly extremely upsetting.

  Tracy reached over and patted Maya’s hand. At least someone could comfort her since I couldn’t. “Have you talked to her since?”

  “No, but I sent her an e-mail.” She paused and looked down at her notebook. “She’s a single mother.”

  “What’s that got to do with anything?”

  This time, both Tracy and I glared at Chris.

  “She works, and she takes classes, and she raises two kids.”

  “That doesn’t mean she gets a pass on her writing,” Chris said.

  “No, it doesn’t,” I said before anyone else could respond. “But knowing something about a student’s background, the education they’ve received, the situations they currently face, can help a good instructor know when to push, when to support, and when to back off.”

  Chris looked skeptical. “So if someone’s a single mom, you don’t tell them what mistakes they’re making in their writing?”

  “You don’t tell them in a way that overwhelms them,” Maya said. “That doesn’t help anything.”

  “Exactly,” I said. “What would you do differently at the next conference, Maya?”

  She spoke a little about focusing on one kind of error, and then she had a good idea.

  “I guess I could show her her paper from the beginning of the semester and compare it to her most recent one. She’s definitely improving—she just still has a long way to go.”

  “Sounds like it might make her feel more confident if she can see some improvement.”

  “I guess.” Maya still looked glum.

  “You don’t have to wait,” Tracy said. “Why don’t you ask her to come talk to you again? That way you both can feel better.”

  It was a sound idea, but by the time the meeting was over, my sweet girl still looked upset. As soon as I got back to my office, I texted her and asked her to come by at the end of the day.

  A few hours later, she was in my office. In my arms. I held her close, stroking her back, burying my nose in her hair.

  “I just feel so bad.”

  “I know. But it happens to all instructors. I wish I could say that it’s the last time, but it won’t be.”

  “I don’t like this part of being a teacher,” she said, her voice muffled as she spoke into my shirt.

  “You’ll get more used to it, but it’s never much fun. You’re a student, you know how hard it can be sometimes. How overwhelming.”

  Though I didn’t particularly want to let her go, I guided her into one of the chairs in front of my desk. I sat in the other one, scooting near enough so that I could still touch her.

  We talked about the situation for a little bit longer, and I tried to be what Maya needed. I was an experienced professor. I was her mentor. That’s who she needed. But I felt this powerful urge to drive her to my place, and make love to her. Make her feel better. Make her feel amazing.

  She wasn’t ready—and that wasn’t the way to solve a professional problem—but I’d thought about it so many times. How to make it amazing for her. How to introduce her to the act she’s been waiting so long to experience.

  To my surprise, Maya’s thoughts weren’t that far from mine. “I was hoping you’d be alone when I passed by your office this morning.”

  “I saw you, both times, and wished I was too.”

  “It was three times, actually.”

  “How’d I miss such a beautiful sight?”

  She smiled a little at that, but all too quickly, her face fell again. “I just—sometimes I wish you could be my boyfriend.”

  “I am your boyfriend,” I said, automatically. Then I hesitated. “Aren’t I?”

  “It feels like you are. But I meant openly. I wanted to talk to you when I was upset. To tell you about it. And I wanted you to hold me.”
>
  “I did hold you,” I said, not argumentatively. I wasn’t sure where she was going with this, but I wanted to know.

  “I know. I just mean that sometimes I wish things could be different for us.”

  Ah. Somehow, I’d naively assumed that inexperienced as she was, what we had right now was enough for her. And maybe it had been—but she was right. Today she’d wanted a man by her side. And on her side. For support. But I’d only been able to support her in a professional capacity.

  “I do, too,” I assured her.

  “Do you?” Her quick glance at my face surprised me again. How could she doubt that?

  “Of course I do. Maya, I know you haven’t dated many men, but, well, this is what it looks like when one is crazy about you.”

  Leaning in, I kissed her, burying my hand in her hair. Her lips tasted sweet. Firm. I remembered them wrapped around my cock the other day and that thought made me want to take her right here in my office. But that’s not what she needed.

  “I just wish we could… have more of a normal relationship,” she said when we broke away.

  “Like what?” I knew what she meant, but I wanted to see what she’d say.

  “Well… it would be nice if we could go on a date. A real one, not in a study room at the library.”

  “How about tomorrow night?”

  Her eyes lit up. “Really? But what if someone sees us?”

  “So we’ll go for a drive. There’s a great Italian place in Riverside.” That was about forty miles up the highway. Should be safe enough. And she’d love it. The food was incredible, and the atmosphere was classy. Romantic. The last time I’d been there with a woman, that fact had annoyed me. But now, because I knew that Maya would like it, it made me want to take her there.

  “Really?” she repeated again.

  “Really. It’s about time we had our first date.”

  Way overdue, in fact. Since this was Maya’s first real relationship, I was determined to make it as normal as possible under the circumstances. Which wasn't all that normal, but I’d make tomorrow night special for her.