Late Night Confessions: A Steamy Older Man Younger Woman Romance Read online

  Late Night Confessions

  Mia Madison

  Contents

  1. Maya

  2. Maya

  3. Maya

  4. Maya

  5. Maya

  6. Maya

  7. TJ

  8. Maya

  9. TJ

  10. Maya

  11. Maya

  12. TJ

  13. Maya

  14. TJ

  15. Maya

  16. TJ

  17. Maya

  18. Maya

  19. Maya

  20. TJ

  Epilogue

  Backmatter

  About the Author

  Copyright © 2017 by Mia Madison.

  All rights reserved.

  No part of this book may be reproduced in any form or by any electronic or mechanical means, including information storage and retrieval systems, without written permission from the author, except for the use of brief quotations in a book review.

  This book is a work of fiction. All names, characters, events, locations, and incidents are the product of the author’s imagination or are used fictitiously. Any similarities to real people, places, or events are entirely coincidental.

  Maya

  I’m a 22 year-old woman, and I’ve never been with a man.

  Just typing those words on the screen made my heart beat faster. If I actually got brave enough to press SEND, my heart would probably pound a hole through my chest.

  Tonight, like every other night this past week, I was lurking on CUNFESHUNZ, an anonymous website where people shared their deepest secrets with strangers. The things people shared were amazing. Some shocking, some sexy, some sad. Some all three. But I’d never shared anything here. I just watched other people be brave. Sometimes I responded to them, though. When people posted a confession, then others would comment and a thread would be started. A lot of people were supportive, but like anywhere online, some were mean.

  People would probably be mean if I posted my secret. All my friends had slept with at least one guy, often more when we were in college. But not me. And now I was in graduate school and untouched. Probably I was the only virgin in my class tomorrow—and I was the teacher. Well, the graduate teaching assistant, at any rate.

  Strange to think that the undergraduates I taught were more experienced than me in that way.

  My finger hovered over ENTER key on my keyboard. All I had to do was to lower my pinkie a half inch. And my words would post for my fellow late-night lurkers to see. To react to. To comment on.

  What would they say? What would they think? Would they think there was something wrong with me? Half the time I thought that, but the other half, I knew I’d spent the last four years focused on my studies. And holding down a work-study job. I’d barely had time for friends, let alone boyfriends.

  Thinking about friends made me think of Andy. And his offer. An offer I’d considered for months—and finally agreed to. I’m still not sure why I committed to going over to his place tomorrow night. But it was time.

  Slowly, I moved my pinkie finger from ENTER to DELETE. But before I could press that key, my fingers took over, flying over the keyboard.

  And before I could overthink it, I pressed SEND.

  A moment later, I was staring at the screen, at the words I’d typed. Words that anyone on the site could now see:

  I’m a 22 year-old woman, and I’ve never been with a man. But that all changes tomorrow night.

  Maya

  Oh God. What had I done? The responses were coming in fast and furious.

  Hey baby! I can pop your cherry for you.

  Where you at?

  You go, girl!!

  What are you wearing?

  You got video chat? I can teach you stuff.

  You want a real man, send me a PM.

  Disgusted, I pushed back from the computer. In addition to the people posting under my confession, there were at least a dozen private messages, or PMs, waiting for me to open or ignore.

  With a sigh, I went to get a glass of water from the tiny kitchenette of my apartment. I’d lived in the dorms during college, serving as a Resident Advisor to help make ends meet. Now, for the first time in my life, I had my own place. I was in graduate school. I was an instructor. But I still didn’t feel like an adult.

  That’s why I’d accepted Andy’s offer. A kind of friends-with-benefits thing. The friends part was definitely true. We’d been friends since sophomore year when we’d been in the same study group for a general chemistry course. He was a good guy even though he still had one more semester to go before graduation. He’s spent so long before deciding on a major, he was almost a year behind.

  Andy was a good friend, maybe my best friend. Which was probably a weird thing to think, given that I was going to sleep with him tomorrow evening, but what if I didn’t meet the man of my dreams for years? The only thing worse than a twenty-two-year-old virgin was a twenty-five-year-old one. Or thirty.

  Sitting down at my computer again, I thought about it. I didn’t want to wait years more to see if I met the right man. What if he never came along? I was ready now. Well, maybe “ready” wasn’t the exact right word. But twenty-two was old enough.

  My inbox at CUNFESHUNZ had filled up with even more private messages. I deleted the ones that had an attachment. No doubt those were mostly dick pics. Yeah, I was a virgin, but I wasn’t completely naive about the way that men’s minds—and other body parts—worked.

  Other PMs said things like:

  Why wait for tomorrow? Let a real man take care of you tonight.

  I’ve broken in eleven virgins—wanna make it an even dozen?

  I will show you the Best. Time. Ever. lolz

  Delete, delete, delete. That was easy. But then one more PM popped into my inbox. One that made my hand still even as I was already reaching for the trashcan icon. This one just said: Why?

  Frowning, I looked at that one word. How was that even a question? Didn’t everyone want to have sex? For either recreation or procreation, or both?

  Without thinking about it, I opened the private message. That was all he’d written, just that one word. The sender went by TJbard. Was he some kind of musician? Or maybe a poet? It was hard to guess from usernames. Mine probably wasn’t providing him with much information, either: MayBee3. The May was for my first name, Maya, and the B for my last name, Bruckner. The three was just because it rhymed.

  I typed out a response. What do you mean why?

  His response was quick. Why tomorrow?

  I sighed. I didn’t want to explain about Andy’s offer. Because it’s time.

  TJ: Is tomorrow your birthday or something?

  MB: No, why?

  TJ: I thought maybe that might be the sense of urgency.

  There didn’t seem to be much difference between a twenty-two-year-old virgin and a twenty-three-year-old one. Both were rather pathetic, in my opinion. And I told him so.

  TJ: Not pathetic at all.

  MB: Seems like it to me. Everyone on this website is confessing to doing all this crazy stuff. Threesomes. Sex in public places. Joining the Mile-High Club.

  In actuality, people talked about far worse things than that, but those were the tamest examples I could think of off the top of my head.

  TJ: That last one’s overrated.

  MB: You’ve tried it?

  TJ: No, but most of the airplane restrooms I’ve seen are barely big enough for one person, let alone two.

  I had to agree with him there. I’d only flown twice, but the restrooms had been very small. And not really the type of pl
ace to make a person feel hot and bothered. More like claustrophobic and confined. Out of curiosity, I looked at his profile. Not much info there. He hadn’t added a picture or user avatar. Not even an age. But then I did a search, and found the last confession he’d posted:

  I’m a 36 year-old divorced man, and I’ve never been in love.

  Wow. That wasn’t the kind of thing people usually confessed to at this website. It seemed more honest. More real. Time to see if he could answer questions as well as he could ask them.

  MB: Why didn’t you love your ex?

  TJ: I loved her at the time.

  MB: Your confession says otherwise.

  TJ: I said I’d never been in love. Not that I didn’t love her.

  Now I was curious. I’d never heard that distinction before. What’s the difference?

  He was silent for a moment. Then little dots appeared on the screen next to his user name indicating that he was typing. To me, love is what you feel for family. For good friends. For your boyfriend, girlfriend, child, and spouse. It’s admiration, affection, genuine caring. But being IN LOVE is more. It’s meeting someone and your heart beats faster. Your whole body is pulled towards them. You think about them all the time. You can’t stay away from them.

  Involuntarily, I felt a chill run up and down my spine. What must it be like to have a man feel that way about you? To feel that you’re his whole world? Of course, that kind of thing was rare. It had never happened to me, and apparently, it hadn’t happened with him and his ex-wife, either.

  MB: So if you didn’t feel that way, why’d you get married?

  TJ: We were young. And stupid. At least I was stupid.

  MB: How young?

  TJ: Around your age, if you’re really 22.

  MB: I am. How come you never tried again?

  It was a forward thing to ask, but that’s what this website was all about. It was far easier to be direct and brave on an anonymous website than in real life. At least it was that way for me.

  TJ: How come you’re so eager to lose your virginity?

  MB: Nice subject change.

  TJ: I thought so.

  I was pretty sure there was a smirk behind those words. Briefly, I wondered what he looked like. It’s just... it’s long overdue.

  TJ: That’s a reason to do laundry, not to have sex.

  MB: All my friends first had sex a long time ago.

  TJ: And if all your friends—

  MB: Don’t say ‘if all my friends jumped off a bridge, would I?’ You’re 36, not 86. If that’s your real age.

  TJ: Touché. Yes, I’m 36. But don’t change the subject. Your first time should be because you really, truly want it. Not because you think it’s time.

  MB: I want to. I mean, I think I do.

  TJ: Shouldn’t you know for sure?

  MB: Probably.

  I slouched in my desk chair in my tiny apartment and stared at the screen. All the things he was saying were things I’d asked myself. But somehow hearing someone else say them, even an anonymous stranger, made me reevaluate my answers.

  TJ: So, about tomorrow night... none of my business, but is it someone you’re in love with?

  MB: No.

  TJ: Someone you love?

  I hesitated. Kind of. He’s a good friend.

  TJ: So, a ‘friends with benefits’ thing.

  MB: Yeah. Ever do that?

  TJ: Not really. Mostly, I meet women, we start dating, we have sex. Usually in that order.

  A laugh escaped my lips. If I met a guy who said that in real life, I’d probably run the other direction, but online, in a safe, anonymous space, I liked that he was telling me things. That he was treating me like an adult. The last thing I wanted was for him to talk down to me just because I’d never had sex.

  MB: How old were you when you first had sex?

  TJ: It was in high school, so I guess I was seventeen. Junior year.

  MB: I was sixteen in my junior year. I skipped a year in middle school.

  TJ: Smart chicks are really hot.

  I laughed. TJ was certainly easy to talk to. Try awkward, immature, and shy.

  TJ: Sounds hard.

  MB: It was. I guess that’s why I never dated. I always felt like a baby compared to my classmates. Like I could never catch up to them in maturity.

  TJ: But I take it you more than equaled them in the brains department?

  MB: Maybe sometimes. Okay, probably most of the time. But there’s more to life than that.

  TJ: Yes, there is.

  My fingers hovered over the keyboard for a moment. Did he think I was bragging? But somehow, I felt he understood me. That I could say things to him without being judged. Maybe it was the anonymity of the website—or maybe it was just him. He was very easy to talk to. Or at least chat with.

  So maybe he wouldn’t laugh at my next question. I typed it out and hit send before I could chicken out. Did everything feel different after you had sex?

  TJ: You mean before or after she finished gushing over how wonderful I was?

  I grinned at that. Young men were not known for having a lot of finesse the first time. Clearly, you were a child prodigy.

  TJ: Naturally. She said it was the best thirty seconds of her life.

  MB: Lucky girl! But it’s a serious question.

  TJ: Okay, I’ll quit joking. It didn’t change anything about my life… but I felt different afterwards.

  MB: Different how?

  TJ: More mature. Or at least it felt like it. And all the jokes about sex suddenly made more sense.

  It wasn’t often I was able to ask people things like this, so I wanted him to give me real answers. Do you think you were actually more mature?

  TJ: Probably it just felt that way. But it also felt like I’d crossed a threshold somehow. And it made me more comfortable with her. My girlfriend. We didn’t date for all that long after that, but for the few weeks after that, we were just more… connected. I was always touching her or she was always touching me. Holding hands. Rubbing each other’s back. We just had this connection. Maybe it was just physical, but it felt like something more.

  MB: Why’d you break up?

  TJ: She was a senior, and after she graduated, she got a summer internship and then went to school out of state.

  MB: An older woman—how exciting!

  TJ: I thought so at the time. But there’s a certain appeal in younger women, too.

  MB: Oh really?

  In my eagerness to hear more about that topic, I scrolled quickly through some emoji and tried to send him a little smiley face that had one eyebrow raised. In my haste, however, I sent him one that appeared to be snoring. Oops.

  TJ: People react that way a lot when I talk.

  MB: Somehow I doubt that. But I was going for a different one.

  TJ: Good to know.

  Maya

  He excused himself to get some coffee after that—who had coffee at 11:30 on a Saturday night? While he was gone, I got up and took a stretch break. I felt oddly excited. TJ was very fun to talk to, and I was already eager to continue our chat. It was nice to have something to look forward to.

  Then I stopped cold. I did have something to look forward to—my date with Andy tomorrow night. Well, maybe “date” wasn’t the right word. But “appointment” wasn’t right, either. Whatever it was called, that was what I should be thinking about, not some random guy online. Yet as soon as my desktop app chimed indicating I had another message from TJ, I rushed back to my desk.

  The next time I looked up at the clock, it was almost two in the morning. I couldn’t ever recall chatting this long with anyone. But I didn’t want it to end. I felt as wide awake as I usually did at two o’clock in the afternoon.

  By four, though, my vision was starting to get a little blurry.

  MB: I can’t believe we’ve chatted this long.

  TJ: Me either, but I didn’t want to stop.

  MB: I didn’t either.

  TJ: But I probably should. I’m an old man. I
t’s past my bedtime.

  I giggled. You’re 36. That’s not old.

  MB: It’s old enough.

  TJ: Old enough to know that some things are important.

  MB: Like what?

  TJ: Like your first time.

  MB: Oh.

  That topic hadn’t come up in the last few hours. We’d talked about travel, music, and dozens of other things… but not that. In retrospect, I think I was hoping he’d bring it up again since I wasn’t brave enough to ask him what I really wanted to. Do you think it’ll make me feel different?

  TJ: Maybe. Sorry, I meant MayBee3.

  My screen name. He was funny. I just feel like I’m ready.

  TJ: I’m sure you are. You’re an adult. You’re funny, smart, and confident. You’re ready.

  Little dots appeared at the bottom of the chat window, indicating that he was typing. But then the dots disappeared without any new words from him.

  MB: But?

  TJ: How’d you know there was a but?

  MB: As you said, I’m smart.

  TJ: And modest! Okay, here’s the “but”… are you doing this because you’re ready or because you really want to be with him?

  His words seemed to hit me in the gut. I’d asked myself that question many times over. But I’d already been over all this, and I’d made my decision. I didn’t want him to be all insightful now.

  MB: Both.

  He sent me the little raised eyebrow emoji that I’d tried to press but missed before.

  MB: Okay, more the former.

  TJ: That’s what it sounds like to me.

  MB: Is that bad?

  For some reason, I didn’t want him to think less of me.

  TJ: Of course it’s not bad. People have sex for all kinds of reasons. But it is really how you want your first time to be?

  Slumping a bit in my chair, I thought about it. I’d always imagined that I’d lose my virginity to someone I loved. Someone I planned to spend the rest of my life with. Well, at least when I was younger and more idealistic. And when I reached college and all my friends started spending the night with guys, I realized that sex wasn’t something that only happened when you met the love of your life. Probably most kids in high school already knew that, but I was a slow study when it came to guys.