u/Agile_Owl1471

After posting my first confession, my DMs were literally flooded....so many “hi”, “hey”, “hello beautiful” messages, all sounding the same, all trying too hard. I was just scrolling through them without really caring, opening a few, replying to none. Then his message came....simple, calm, “enjoy whatever you’re doing.” And for some reason, that caught my attention. In my head I was like, okay… nice guy. But he turned out to be something completely different. We started with normal hi-hello, random basic talk....where I live, what I do...nothing unusual. Then suddenly he said that our chats could be NSFW if I wanted. I told him honestly that I had never done anything like that before, and he just replied, “there’s always a first time.” I don’t know what made me go along with it, but I did. I thought, what’s the worst that can happen?

He was 34, I’m 20...almost a 14-year gap....and you could actually feel that difference in the way he spoke. He wasn’t like guys my age; he had this calm, dominating way of taking over the conversation. He didn’t hesitate or soften things, he just kept asking questions....back to back....about what I like, what I think about, what I imagine. At first, I was a little intimidated, not going to lie. It was that “I know what I’m doing” kind of energy, almost like those daddy-type vibes, and it made me pause. But instead of pulling away, I stayed. The way he spoke, the way he built things...it pulls you in. He didn’t just talk randomly; he created situations, slowly building them layer by layer until it didn’t even feel like a chat anymore, it felt like stepping into something else. Some of the things he said would’ve sounded weird or even wrong if I thought about them normally, but in that moment, it didn’t feel like that. It just felt like imagination, like a space where nothing else mattered. you won’t believe the kind of roleplay this guy got into. Like he literally created a whole scene where he was acting like my cousin and I was just me, and it started with teasing and building tension…about to fuck each other, and then suddenly he twists the whole thing by bringing in another character (my jiju) and changing the situation completely. My jiju wants to fuck me now. The way he builds it is so smooth that in the moment it doesn’t even feel weird, it just pulls you in deeper.

Time passed without me even realizing it. We started around 8 in the evening, and before I knew it, it was 1 or 2 at night. The conversation never stopped...constant teasing, constant back and forth, him pushing, me pretending I wasn’t affected. He had this habit of saying something bold and then pausing, like he was waiting to see my reaction, and I’d act casual, like nothing got to me, but inside it was completely different. Sometimes it genuinely felt like he could read my mind, like I didn’t even have to say anything and he already knew where my thoughts were going. Somewhere in between all that, I crossed lines I never thought I would. Without even realizing it, I ended up sharing things I normally wouldn’t with anyone, let alone a stranger. And the strange part is, in that moment, I didn’t regret it.

And I swear, he clearly has a thing for these family relation style roleplays… like that’s what turns him on the most. Not gonna lie but I liked it too.

He also told me about his past...about his ex and how wild things used to be....and I remember thinking, damn, she must’ve been enjoying it a lot. And somewhere deep down, I wanted to match that energy. I never told him what was actually going on in my head while we were talking, but girls know how to hide that well. Still, he kept talking like he already knew, and maybe he did. At one point, I even caught myself thinking, why am I not stopping this? But I didn’t want to. It wasn’t just chatting anymore; it felt like a game, and he was clearly better at it than me. The way he controlled the flow, the way he kept things going without a single dull moment...it was addictive.

Also, not gonna lie… the whole time we were talking, I was completely into it. I was wet. I didn’t even tell him anything directly, but he could just tell.

The way he kept going, the confidence… he knew I was enjoying it. And he was clearly turned on too, like he literally said it without hesitation.

It was crazy honestly… like I didn’t expect myself to get that involved in a conversation like that.

By the time the conversation finally slowed down, I just sat there staring at my screen, smiling for no reason, a little shocked at myself but not really regretting anything. He’s crazy, freaky, maybe a little messed up, but he knows exactly how to keep someone hooked. And out of all the DMs I got that day, he’s the one I still remember.

Real BTW.

I have this colleague who works WFH for our company. A South Indian guy. He lives in the South while the company is based in the North, and somehow, I ended up coordinating with him for work. He’s almost 8 years older than me.

The first time we interacted was during a meeting over VC. I still remember hearing his voice and thinking… damn. Calm, deep, slightly intimidating, but weirdly comforting too. Back then, it was all professional. Work updates, deadlines, shared documents, formal conversations.

Very “Good morning, sir” energy.

But somewhere between endless work calls, random late-night texts, and checking up on each other after long days… things changed.

Slowly.

Unexpectedly.

What started as business conversations somehow turned into daily conversations. Then personal ones. Sharing random thoughts, memes, complaints, little moments from our day, advice, teasing each other for no reason. Calls that were supposed to last 2 minutes somehow stretching into hours.

And one day, “Good morning, sir” quietly turned into “Hello, baby?”

It’s been 2.5 years now.

And honestly, I never thought someone from work would become this important to me.

The flirting got dangerously natural between us. The kind where you don’t even realize when it stopped being “just joking.” I think he caught feelings first… but maybe I was already gone too.

Something that started with sharing pictures of documents slowly turned into selfies, random mirror pictures, half-nudes, secret moments meant only for each other.

The funny part?

We’ve never even met in real life.

And somehow, he still feels closer than most people I see every day.

He’s always busy. Traveling. Working. Handling a hundred things at once. But no matter how hectic life gets, he never makes me feel forgotten.

Sometimes I wonder how someone sitting so many miles away can still affect my mood this badly.

I still remember casually showing him my tattoo once. Such a normal moment. But with us, nothing ever stays normal for too long. One flirty comment led to another, the tension shifted, and suddenly we were both lying in separate beds, staring at our phones like idiots, wishing distance didn’t exist.

We’ve tried meeting so many times.

Failed plans. Bad timings. Work trips. Last-minute cancellations.

Every single time.

But he always says the same thing to me:

“When we finally meet, I’m not gonna leave you.”

And God… the way he says it makes my heart melt every single time.

I think some people in the company already have an idea about us. Maybe the way we talk. Maybe the way we instantly notice each other in meetings. Maybe the jealousy when someone else coordinates with him instead of me.

Because yes, I get jealous.

And he does too.

But honestly?

Who cares.

There’s something stupidly beautiful about having someone who feels like home even before you’ve touched them.

Maybe someday we’ll finally meet.

And maybe all those years of waiting, teasing, flirting, missing each other, almost-meeting… will finally make sense the moment I see him standing in front of me.

Never thought I’d actually meet someone I met online. I was supposed to ghost him after the first meet, disappear like I always planned to. I was scared of meeting strangers in real life, kept cancelling plans again and again, but somehow… this one felt different.

Now I sit here wondering whether meeting him was the best decision of my life or the worst one.

He’s in his 30s, I’m in my 20s, almost a 10 year gap between us, but the way he looks at me makes it feel like age doesn’t even exist. What started as random late night chats turned into something way too intense, way too real.

And now his marriage is happening very soon.
Still, he keeps telling me the same thing over and over, that he’ll never regret meeting me. He asks me,
“Shaadi ke baad bhi milogi na?”
“Tum mujhe regret feel toh nahi karvaogi na?”

Maybe that’s what messes with my head the most… because he sounds so sure about us, even when life is clearly moving in another direction for him.

I don’t know what this is anymore. Temporary? Toxic? Real? Maybe all three.
All I know is that I was supposed to forget him, and instead we became each other’s addiction.

Maybe I should’ve never met him.
Or maybe some people are meant to ruin your peace a little before they become a memory.

What can I say… I’m just a girl.

I never thought I’d ever meet a guy from online in real life. I was always the type who found it risky, weird even. But then in January this year, I started talking to this guy on Telegram. At first it was just casual flirting, late-night conversations, sex chats, exchanging pictures, fantasies… things that slowly became part of our everyday routine. We would talk almost twice a day, every single day.

The strange thing was, we never showed each other our faces. It was all words, voices, imagination, and desire. Yet somehow, we got attached. He kept asking me to meet him in person, again and again, but I always backed out at the last moment. I was scared of online people, scared of what could happen. There was also almost a 10-year age gap between us, which made me hesitate even more.

But after months of talking, I finally agreed. In March, after office one day, I went to meet him at the hotel he was staying in. It was the first time I was actually going to see him. I remember my heart racing while standing outside the room, wondering if I was making the biggest mistake of my life.

When he opened the door, I was honestly shocked. He was handsome. Way more attractive than I had imagined in my head all those months. The moment I entered, we hugged for what felt like forever, maybe three whole minutes, without saying much. Then he started kissing my neck slowly, touching me like he had wanted to for months. Clothes came off one by one, and suddenly everything we had imagined online was happening in real life.

He kissed my body everywhere, touched me everywhere, and then asked me to go down on him. I did. But we didn’t have sex that day. I was still a virgin, and honestly terrified. I didn’t know how any of it would feel, or what would happen, so I told him no. He didn’t force me. He was surprisingly patient and cooperative, and we just stayed wrapped around each other the whole night.

The second time we met was different. I was still nervous, but I wanted him too. Maybe because by then I trusted him, or maybe because desire had already taken over fear. So we finally had sex. My first time. There was blood everywhere, on him, on the sheets, and I remember feeling overwhelmed more than anything else. Somewhere between pain, nervousness, and excitement, I realized I wasn’t a virgin anymore.

We’ve met four times now.

And lately, I’ve started realizing something that’s difficult to admit to myself. I like him, maybe more than I should, but sexually… I never really feel satisfied. I always want more — more intimacy, more passion, another round, maybe even a third. But somehow it always revolves around him. He keeps asking me to please him, to suck him off, to fulfill his fantasies, but he rarely focuses on what I want. He barely kisses me the way I crave, barely touches me the way I wish he would.

The last time we met, he even asked me to kiss his asshole because it was his fantasy. And while I didn’t completely hate the idea, somewhere deep inside I kept thinking — what about me? What about my pleasure? My desires? My satisfaction?

Sometimes I feel like I push myself harder for him than he ever does for me.

I’m 20 now, and no longer a virgin. My first time happened with someone who was technically a stranger once. And maybe the strangest part of all this is that I still don’t know whether this story is about desire, attachment, loneliness, or just me trying to feel wanted.