Hello r/Erotica! I just joined this subreddit and decided to post my story.

I am reconstructing my story from my diary, emails, texts and memory. Granted, I am definitely romanticizing things, but this is how I remember it. The conversational parts are obviously paraphrased.

-Red

This is the story of my first experience with an older man. It's a bit long, so I'll break it down into parts.

I've always had a thing for older men; there's just something about them that gets me. When I was 20, I hadn't dated anyone older, even though I was curious as hell. My only romantic experience was with my so-called best friend, but after he took my virginity, poof—he vanished, as they sometimes do.

Back in the day, I used to daydream about older guys and how they knew their way around a woman, or at least how I imagined they did. But I was painfully shy, partly because of cultural reasons and just being a young woman, you know how it is. Despite my fantasies, I never had the guts to actually pursue anyone.

Then one day, life threw me a curveball in the form of a coffee shop mishap. I was grabbing my wallet when a quarter flew out of my hand and rolled towards someone's foot. The guy picked it up and handed it back to me with a smile. I mumbled a sheepish thank you, and that's when he hit me with, "Wow, those eyes of yours! They must get you in trouble."

I was caught off guard and managed a bewildered "Excuse me?" It wasn’t because his comment was swoon-worthy (I was used to compliments about my body, especially my chest). He explained that my eyes were super expressive and gave away everything about me.

I'd been hit on before, but this guy… He locked eyes with me, and I couldn't look away. His gaze was intense, almost intrusive, and it gave me such a rush.

I was a mess of nerves, not sure how to respond to him. But despite feeling flustered, I was oddly drawn to his calm demeanor. It was like he was talking directly to me, like I was the only person in the room. All I managed to stammer out was, "I’m sorry, I’m shy and nervous." In any other situation, I’d have bolted, but for some reason, I wanted to stick around.

When I admitted my nerves, he asked if I wanted to bail, and honestly, part of me did. But I shook my head no, and he suggested I sit down. I know, what was I thinking? I wasn’t!

I won’t bore you with all the details, but over the next few minutes, he helped me calm down. We chatted casually—well, as casually as you can with that kind of tension in the air. He asked questions, I answered, I asked questions, he answered, and there was this subtle humor between us that made it all surprisingly comfortable.

After what felt like forever (but was probably only 20 minutes), he said he had to run to a meeting. Before he left, he hit me with one last nerve-wracking line: "I enjoyed your company, Ms. REDiance. I’d like to stay in touch. Would you like that?" I blurted out, "Sure, let’s be friends." That’s when he dropped the bomb: "No, I don’t want you to see me as a friend. I see you as a woman, and if we stay in touch, it’s gonna be on that level." Cue my best deer-in-headlights look. He told me to think about it, handed me his number on a piece of paper, and before I knew it, he was gone... leaving me stunned.

After that encounter, I was left overwhelmed and indecisive, but I couldn't deny that I wanted more. Figuring out how to make contact with him became a mental maze. Should I text him? Should I call? And then the doubts crept in: What if he was married, with kids, living in some perfect suburban home? Those thoughts swirled in my mind, but they didn't stop me from "fantasizing" furiously about what it would be like to be with him. What kind of man was he? Sure, my experience was minimal, but I'd read my share of erotic stories and watched some porn, though I always preferred reading. Porn felt too blunt, if that makes any sense.

More than two weeks passed, and I still couldn't bring myself to dial that number or even draft a message. What would I even say? "Hey, it's the nervous redhead from the coffee shop"? What if he replied with, "Which one?" Maybe that was his thing, picking up girls at coffee shops. What if all he wanted was a quick fling? My mom's voice echoed in my head, calling it "my flower" and warning me "that's all men want". I was a bundle of nerves, torn between wanting to move on but then my brain would chime in, "Move on to what? Hoping another stranger makes a move, because you sure as hell aren’t going to."

I tried convincing myself to let it go, but I couldn't bring myself to toss out that slip of paper with his number on it. Sometimes, after a particularly steamy moment alone, I'd look at that paper and think it might just be a keepsake—a reminder of that intense encounter.

The only time I managed to stop obsessing over this was during school and work; outside of that, my mind was constantly at war with itself. Realistically, I had been sheltered my whole life, with minimal experience with men. I was shy and struggled socially. My only friend literally fucked me and vanished. Social interactions were rare, mostly confined to my part-time job. Otherwise, like most people my age, I found solace in online interactions. Funny how that's exactly what I'm doing now, isn't it?

One day, I had such a great day at work and school, feeling good overall. I remember thinking, "I wish every day could be like this!" Anyway, I told myself, "Okay! Today's the day I'll text him." Then my mind raced: "What if he wants to meet today?" He was clear he wasn't interested in just being friends, so reaching out meant I was agreeing to see him differently, right? Before I could talk myself out of it, I sat on my bed and after a few ridiculous drafts, finally wrote the perfect message. In quiet moments, I still look at our texts... I'll probably delete them one day, but not today. It said, "It's REDiance from the coffee shop. I hope this isn't too forward, but I've been thinking about our conversation and your offer to keep in touch. Are you still up for that? 😊".

And then I hit SEND.

Right after hitting send, I started second-guessing myself: "That was such a dumb message. He's probably thinking 'LOSER' now when he reads it... SHIT SHIT SHIT." I obsessed over it, reading and re-reading, thinking of all the better things I could've said.

After what felt like waiting through two eternities without a reply, I gave up and felt totally rejected, like the biggest loser. I just flopped down on my bed and moped. I thought about sending a lame excuse like "oops, wrong person!" but let's be real, that would've sealed my fate as "loser of the year." So, I just sighed and lay there, phone next to me, clinging to hope.

Then, "DING," I got a message. I was dying to check it, but I also didn't want it to be a letdown from mom, dad, or work. So, I took my sweet time, staring at the screen, hesitant.

Finally, after enough delay, I glanced at my phone. It was a message from him!!!

As I picked up my phone to read the message, it said, "Hello Ms. REDiance, I’m so pleased you decided to take me up on my offer to stay in touch. How have you been?"

So casual, as if I hadn’t been mortified the last few weeks trying to figure out if I should reach out to him, right? I have to admit, I was relieved to see that he wasn’t put off by my message and thinking I was some sort of loser.

Of course, I obsessed over what to reply. I finally decided to be funny. If he could be direct, why shouldn’t I be funny? So I said, "I'm good, a little busy, but I thought I’d send you a message to see how you were doing. I’m still interested in being friends... lol".

His response was a bit more direct than mine. He said, "I'm doing well, thank you for asking. I appreciate you reaching out, but I want to be clear that I'm looking for something more than just friendship. If that's something you're open to exploring, I'd love to get to know you better. Are you open to exploring this?"

I thought to myself, "Jesus, learn to take a joke!" But there was a part of me that was impressed by his lack of interest in mundane humor and his ability to stay on track with what he wanted. This would've killed with a younger guy.

Again, putting me under pressure... but I liked it. I decided to match his directness and sent a message saying, "Are you married?" Jesus! I was so nervous! What if he said "Yes"? Was I ready to be "the other woman"? What if we really hit it off? Was I ready to be a home wrecker? What was I thinking? Of course, he was married! Why else would he be interested in someone like me?!

Now, it was a matter of waiting. I figured it was my turn to turn the tables and put him under pressure. Surely, he would fold.

I figured it would take him a while to respond; after all, he was married. He'd have to come up with a good story like "yes, but we're only together for the kids" or some variation of that, just like my mother said in her "life lessons".

As you might have guessed, he responded right away, saying, "I asked if you're interested? If you're interested, then it won't matter".

Now, I knew no matter what I said, he would come back with, "Are you interested?" So, I said, "Yes, I am interested." I mean, I obviously was, so I might as well come clean.

I remember thinking to myself, "Here comes the bullshit."

His response was, "No, I am not married. What are you looking to get out of this relationship?" WHAT??? He managed to put ME on the spot again? How the fuck did he do that?

If I asked, "What are YOU looking to get out of this?" surely he would see right through it and know I didn't have a real answer. His directness had cornered me into really thinking about things. This was so much easier with younger guys online; I could bend them to my will so easily.

Alright, I decided honesty was the best policy, so I went for it and said, "I really don't know, but I am intrigued".

His response was "Good girl. Honesty is always best. As long as you're honest with me, I have something to work with." How the hell did he know what I was thinking? Then I remembered "ah! older guys, they've heard it all before"... But why did it feel good when he said "good girl"? For some reason, I felt rewarded by his approval. I remember thinking "holy shit... am i one of those??"...

Anyway, now I was even more intrigued than before, I asked him "what are YOU looking to get out of this?".

His response was a simple "Let's get together for dinner, or coffee, and we can talk about all this while getting to know one another. This conversation will be much better in person, don't you think?".

This guy moved fast and made all my anxieties flair up, but also made me excited and curious at the same time. I honestly did not know what to do. Going out with him was something that was nerve-wracking for me, not only was I not used to face-to-face interactions with men, but he was so direct. I was not ready for that.

Again, I opted to be honest, that seemed to work with him and I was starting to realize that I felt good after being honest with him, so I went for it and said "Honestly, I am still very nervous about this whole thing. I definitely would like to get to know you better, but this is going a lot faster than I am used to".

He responded very quickly saying "I understand your angst, but I also know that the best things in life come unexpectedly and usually after a moment of discomfort. I certainly want to make sure you're comfortable when we meet again, but I also want to make sure we don't miss any opportunities we have to get to know one another".

As I read the message, I kept thinking that he sounded understanding, but not without expressing his thoughts and desires... I liked that. As I was still processing that message, another message from him came in saying "Here is what we can do, I have to go out of town for a few days, why don't we make plans to meet when I come back?". "Ding" another message saying "Of course that is with the understanding that if you're still not comfortable, then you can let me know and we'll decide what happens then. Is this something that you can work with?".

Again, he sounded very understanding and it felt as if he was trying to take some pressure off of me, which was a welcomed change to what I was used to. I decided to be funny and sent him a "challenge accepted" meme, you know the one. However, there was no response... I waited 15 minutes, nothing... 30 minutes, nothing... after an hour of waiting, I decided to send another message saying "That sounds like something I can live with". He immediately responded "sounds like a great plan. I am looking forward to our first date!"

And that was the end of that interaction, but I was left with more questions: Why was he going out of town? Was it work? What did he do for a living? I also wondered what did he mean by saying "we'll decide what happens then" if I decided not to meet him when he came back? Did it mean he was going to continue dealing with my indecisiveness, or was he going to say "to hell with this, I have many other women waiting in line!"?

Yes, I tend to overthink things...

The next few days were uneventful, and our conversations became rather... "dry," so to speak. Gabriel would send me a daily text wishing me a good day and telling me how he was really looking forward to our date, but nothing much deeper than that.
However, something that stood out to me was how he always called me "Ms. REDiance." It sounded very formal and respectful. I liked it, but I kept trying to figure out the reason behind it. I didn’t want to ask directly because I knew I’d be nervous when we met, so I figured I should have some conversation pieces in store for when we met in person... you know, just in case.

After four days of him being out of town, he actually called me. When I say my heart jumped out of my chest, I mean it almost literally did—I nearly had a panic attack. It got so bad that I didn’t pick up the phone.
I was used to a pre-call arrangement with people (a text asking if they could call and such), which generally gave me time to prepare myself, but apparently, Gabriel didn’t get that memo!

Anyway, after my little heart attack, another thing out of the ordinary happened: he left a voicemail. WTF???

The voicemail, in a very calm and casual tone, said:

"Hello Ms. REDiance, this is Gabriel. I'm calling to let you know that I am back in town and would love to finalize our plans to go on our date or see if you still wanted to go.
Please give me a call back when you are free. Have a great day."

I must've listened to that voicemail ten times before I was able to put down my phone and think about what I should do next. By this point, I already knew that he was very direct and not shy about making plans, so I wanted to have a way out just in case he asked to meet tonight or something like that... I mean, I wanted to, but I was soooo nervous!

So many things went through my head like:

What if he wanted to have sex immediately? Was I ready for that?
What if he didn't like me? I mean, who wouldn't, but you never know!

I remember grabbing my face thinking, "I don't know... I don't know... I don't know!!" and "RED, you're such a punk, no wonder EX-BFF left and never came back." Yeah, I used to blame myself for a lot of things when I was younger. Anyway...

Finally, after having a bit of a breakdown, I decided that I needed to go out with him and that it would be good for me. This, of course, did not come to me naturally; this is something I understood after posting my dilemma on Yahoo Answers.

Now it was time to call him back... well, it was time to look at the phone for 45 minutes and then call him back... I was sweating and stressed beyond belief (kept thinking of the Eminem song where he says "palms are sweaty, knees weak, arms are heavy"), but I kept reminding myself that this was something I wanted, and it was just a phone call... so I hit "send" on my phone and heard the phone ring, longest few seconds of my life.
There was something inside me saying, "Please don't pick up, please don't pick up"... but no luck, he picked up. My heart sank to my belly, and I did everything I could not to hang up the phone. All I heard was, "This is Gabriel, how can I make your day a little better today?"... yeah, I know... WTF???

I stammered an almost-casual, "He-hello, this is RED," and he responded, "Well, hello Ms. REDiance, how are you today?" Again, I opted to be as transparent as I could be and said, "Very nervous." He, very calmly, casually, and reassuringly, said, "Oh, stop, it is not that serious. You will be OK, I promise," to which I just gave a little bit of an audible exhale, and he said, "So tell me, did you decide if you want to go to dinner with me?"... I just said, "I do," releasing a sigh of relief. I won't bore you with any more mundane details about the call because, at this point, they are irrelevant, and I've been paraphrasing this entire conversation.

So, given my indecisiveness during the conversation, he decided that it would be best if we met during the day for a cup of coffee. That way, I would not feel so pressured, and it could be more casual, which was another moment of relief for me.
He really did try to make me as comfortable as possible. He also decided that we should meet the following day at 2 at the coffee shop where we initially met. He said, "We can make that 'our spot,'" which got a little chuckle out of me and put me a bit more at ease.

After the conversation, my anxiety and uncertainty had turned into butterflies in my stomach, and I was looking forward to the next day.

I was still nervous and had a lot of questions, but if I had any doubts about at least meeting him, they were now gone, and I wanted to see it through to the next step.

It was time to overthink the following day...

I couldn’t sleep that night. I was nervous, anxious, and obsessing over everything that could go wrong, but eventually, I managed to fall asleep.
The next morning, I woke up VERY late for class. Normally, this would have stressed me out, but today, the anticipation and anxiety overshadowed everything else. Honestly, I considered canceling. I even caught myself coming up with excuses, but I fought through it.

Eventually, I made it home and took another shower. I’d been sweating all day from nervousness, and the last thing I wanted was for him to remember me as "the smelly redhead from the coffee shop".

As I made my way to the coffee shop, I was sweating again, but I was determined to see this through. I arrived a few minutes early, thinking that if I got there before him, I could pick our table and calm my nerves. But as I turned the corner, I saw him already there. Another pit in my stomach... He was just standing outside, looking at everything and nothing. The next few steps felt like I was walking in slow motion. I was fixated on him, noticing what he was wearing, and imagining his delightful scent.

My moment of serenity was interrupted when he saw me and smiled, acknowledging me with that gaze I remembered so well. When I reached him, there was an awkward moment where I didn’t know how to greet him. My mind raced: "Should I shake his hand? Hug him? What's the etiquette?" We should have discussed this on the phone!

He must have noticed my hesitation because he immediately hugged me—not a romantic embrace, but not a distant acquaintance social hug either. Whatever it was, holy shit! I felt an immediate connection. The hug probably lasted two seconds, but I didn’t want it to end. He smelled even better than I imagined.

As the hug ended, he grabbed both my hands in his, brought them to his face, and kissed them. Holy shit! What is this? What was I supposed to do? His eyes were glued to mine, and I was taken aback, lost in the moment. Without breaking eye contact, he said, "Well, hello Ms. REDiance. I am so pleased to see you again."

I must have looked like a deer in headlights, high on whatever this was.

I managed to say, "You too," but immediately realized it made no sense—none! Embarrassed, I noticed him chuckle softly before he said, "Ms. REDiance, why don't we sit outside? It's such a beautiful day." I nodded awkwardly, but he seemed to understand. He chose a table outside and led the way, with me following.

He asked what I wanted to drink, and I said, "Just a regular coffee is fine." He looked at me and suggested, "Perhaps we should do some tea; it might help you relax a little. Would you like that?" All I could say was, "Yes, please." As he walked inside to get our drinks, I sat there, becoming one with my nervousness and fighting the urge to run away.

Despite the intrusive thoughts and nerves, I realized I was mesmerized by the situation. I was on a date with a man more than twice my age, whom I had met at a coffee shop. I was doing it!

Of course, paranoid thoughts crept in: "Oh shit! Better keep an eye on him to make sure he doesn’t put anything in my tea"... thanks for that baggage, Mom!

Watching him interact with the girl at the counter, sharing smiles and conversation, a little voice inside me whispered, "He is mine, bitch!"... THAT was new.
I’d always had internal dialogue, but never like that or aimed at someone else. There was a strange feeling I couldn't quite identify, a fear of losing him to someone else. It wasn’t the time to dissect it—now was the time to focus on him and try to string together sentences containing more than two words.

When he came back to the table, he handed me my cup and said, "I hope you enjoy your tea. The girl at the counter mentioned it’s her favorite and that it helps her relax." I thanked him, took a sip, and of course, burned my mouth. I sighed, and he smiled, watching me fumble through everything so far. He looked at me with an endearing expression and said, "Relax, it’s okay, I understand." His gaze made me feel so exposed, and I didn’t know why.

Lost in thought, I suddenly realized he was speaking. "So, Ms. REDiance, is that what you prefer to be called, or is there another name you prefer?" I replied, "REDiance is good," but saw this as a perfect opportunity to ask, "Why do you call me 'Ms. REDiance'? It sounds so formal. Why not just 'REDiance'?"

With a small smile, as if expecting this question, he said, "Well, Ms. REDiance, I believe in treating everyone with respect. If you were a man, I’d call you 'Mr. REDiance.' It also helps avoid ambiguities. No one can accuse me of being disrespectful if I address them respectfully. It helps me maintain a respectful relationship with people."
As I focused on what he was saying, I noticed he used his hands a lot when he spoke, and his facial expressions were very apparent. I had to admit, his gestures and expressions helped me understand him better.

I asked, "What if your relationship with the person is casual, friendly, or family? Do you still talk the same way?" This conversation was fascinating to me.
His response was simple and direct. "Of course, I have relationships that aren’t this formal. It depends on the relationship I have with the person. I have brothers, and we still talk very casually and playfully. I have friends with whom I don’t have to worry about how they interpret my words. It all depends on the relationship and the chemistry we’ve developed."

Then it occurred to me that I had the perfect question to transition into discussing the nature of our relationship. I was very proud of myself at that moment. I said, "So, if I decide that I want to have a relationship that is more than friends with you, will you still call me 'Ms. REDiance'?"
Wasn't that a great question? I thought it might stump him for a second or two... but nope! Not even a flinch. He immediately replied, "If WE opt to have a relationship, what I call you will be determined by our chemistry and dynamic, but I can guarantee it won’t be 'Ms. REDiance'".

While his response was clear, I still felt the urge to poke around a bit more, so I said, "So what would you call me?" He replied, "As I said, that would depend on our chemistry, but maybe something like 'Red-iculous'." We both laughed.

The more we talked, the more comfortable I felt, slowly allowing myself to open up and eagerly listening to him. I was enjoying myself; he was fascinating and more charming than I had ever experienced. My nervousness had completely subsided, and I found myself in a state of serenity with another person. I wanted more and more.

I completely forgot all the questions I had prepared and didn’t feel the need for backup topics; everything was just flowing. He made it easy to be myself, and it felt so good. His conversation was engaging and sincere, putting me in a trance. After a while, I realized it had been more than two hours, and my cup of tea was cold and barely touched.

During this time, I learned he was 44 years old and had been married in his 20s. After a few years, they realized it wasn’t working (holy shit! when I was born, he was having marital problems!!!).
No kids. He didn’t want to discuss his job, explaining that he didn’t want my perception of his profession to affect my opinion of him. He emphasized that his work was just a way to earn a living, nothing more. Whether he was a janitor or an executive, it shouldn’t influence how I saw him. What he did not realize is that I paid attention to his hands and they were definitely not janitor hands.

He asked if I had anywhere else to be and said he would understand if I did. I said, "No, I'm fine," but I thought it would be polite to ask him the same question. He said, "I’m exactly where I want to be; I set my whole afternoon for this." While a simple yes or no would have been enough, his response made me feel like I mattered, like I was the only person in the universe that mattered to him at that moment. I could feel my face turn red and normally that would be something I would shy away from, this time I allowed myself to just feel it.

He then said, "I’m going to get another cup of tea. Yours is cold. Would you like one?" The way he phrased his questions made me feel good, protected, almost spoiled. I wasn’t used to that, but I liked it. I got up, grabbed my purse, and said, "Don’t worry, I got it." I figured it was only fair, but honestly, I didn’t want to send him to "Ms. Smiley Pants" at the counter—don’t judge me!

He looked into my eyes and, with a warm yet firm tone, said, "It’s okay, I’ll go get it." For some reason, that moment, those words, sent warmth throughout my body, and all I could do was sit back down. Jesus! What was that?

While he was gone, I had time to think about what had happened so far and where it could lead. I liked everything up to this point, but I kept fantasizing about the future, even tonight!

One thing I noticed while he was gone was how obvious and almost unpleasant his absence felt. I couldn’t wait for him to return.

After what felt like an eternity, he finally came back, placed my tea in front of me, and smiled. "I'm back. Did you miss me?" he asked with a sarcastic grin. I wanted to yell, "YEEEEEESSSSSSSSS!" but instead, I just smiled back, unable to think of anything clever to say, settling for a flushed face and nervous laughter.

As he sat down, he sipped his tea, savoring it—or at least that’s what it seemed like. Then he said, "So, the other day, you asked what I’m looking to get out of this. I can answer that question. Would you like that?"

Deer in headlights, again... for fuck's sake!

to be continued...