I am AK – name changed; 33Y, 5’7″, a working professional, and someone who enjoys weekend-long drives more than parties. I’m good at what I do, passionate about driving, and have always been curious about exploring different sides of myself – including the more intimate ones.
Until recently, I’d never considered putting my personal encounters into writing. But something about sharing these real experiences – the awkwardness, the chemistry, the surprises – felt worth expressing. So this series will be a candid look at the relationships and situations I’ve found myself in, from awkward first messages to intense physical connections. All real. All anonymous. All me.
Trying Something New:
A few months ago, I decided to try dating apps after my last bad relationship. I’m not really ready for a traditional relationship, but more out of curiosity and a desire to meet someone open to Friends with Benefits or a short-term connection. I figured, why not? I’m divorced, honest about what I want, and open-minded.
But to be honest, it wasn’t as easy as I expected. Matching with someone is one thing, but actually getting to the point of meeting them? Way harder. Most conversations just faded out, and some matches didn’t even reply.
The First Real Connection:
In the first week itself, though, something different happened. I matched with a woman who was 30 years old and seemed refreshingly direct. We chatted for a bit – not too deep, not too personal – but there was something comfortable about how it flowed.
We both agreed to meet for a date – no names, no personal questions, no expectations. Just two adults curious to explore, meeting in neutral territory.
Still, I was nervous. Thoughts like “Is this safe?” or “What if she’s not real or it’s a scam?” kept running through my mind. Funny enough, when we finally met, she told me she had the same fears.
This is where it started – my first real FWB date arranged through an app.
She was 5 feet tall, chubby, fair, and confident- dressed in jeans and a modern top with a deep neckline that made her look effortlessly attractive. We met at a quiet coffee shop in South Chennai ECR Road. The moment I saw her, I felt a rush of emotions – curiosity, nervousness, excitement. It felt like meeting a woman for the first time all over again.
Our conversation started off light. We talked about life, work, and the awkward world of dating apps. Over time, the comfort level grew, and so did the flirting. Nothing forced – just small smiles, playful teasing, a little spark in the eyes. After coffee, we decided to continue the evening somewhere more relaxed. There was a beachside less than a kilometer away, and I offered to take her there on my bike.
She held onto me tightly during the ride, and I couldn’t help but notice how natural it felt. At the beach, the conversation shifted. We talked about past relationships, about what we were looking for – she openly shared that she wanted a genuine, no-strings-attached connection. I shared my side too.
That night, after I got home, the connection didn’t fade. We continued texting, which soon turned into flirtatious sexting. It was clear we were on the same page. We planned to meet again early the following week.
The Surprise Morning Plan:
I assumed our next meeting would be casual – maybe a breakfast or a walk by the beach. But she had other plans.
We met at a common location, in the morning at 9 am. She was dressed in a flowing long frock that complemented her curves perfectly. She greeted me with a warm hug and a soft kiss on the cheek, which I didn’t expect. My heart raced for a second. I parked my bike and got into her car. We drove along ECR in silence at first, letting the morning breeze fill the space between us.
Then I broke the ice, teasing her about the kiss and gently touching her hand while she drove. There’s something intimate about being driven by someone—especially someone you’re just getting to know in a different way.
About 20 minutes in, she stopped the car at a quiet spot and turned to me. “Are you ready?”
I said, “For what?”
“Tell me – what would you do if I pulled you closer right now with no one watching?”
She asked with a mischievous smile, before leaning in for a deep kiss. That was the moment the tension broke. It wasn’t just physical- it was a release of all the anticipation built up since our first meeting.
We kissed with raw hunger, our hands exploring, and I started pressing hard against her breasts. For a moment, the world outside didn’t exist – it was just us, tangled in heat. But then, like a jolt, reality crept in. We paused, breathless, lips barely apart, and slowly pulled away, our hearts still racing.
“Let’s go from here,” she said, her voice low but steady. I assumed we were heading to a café or another beach. But soon I realized- we were pulling into a gated villa. A private 2BHK Airbnb with a small pool, tucked away along ECR.
We checked in and both gave our IDs. Finally, the name I heard was Isha (name changed).
She told me she had booked the place two days ago – she had planned this. I was stunned, impressed, and genuinely excited.
Inside, the villa was clean, cozy, and intimate. It was the perfect setting – not just for passion, but for connection. Once inside the villa, the energy shifted. The wild tension from the car gave way to something slower, deeper.
She slipped off her shoes, looked around, and asked, “So… what now?”
I smiled. “You tell me. You planned this.”
She didn’t say anything. Instead, she walked toward me and gently took my hand.
We stood there – just inches apart – and I traced my fingers over her, starting to seduce her.
She leaned in, and I started kissing and biting her lips. “You’ve no idea how long I’ve wanted this…”
We sat in silence for a few seconds after that kiss – our lips swollen, our breath uneven, our eyes locked like we were both asking, “Did that really just happen?” She looked away for a moment, let out a smile, and I could tell she was just as rattled and turned on as I was.
I lay on the bed and let my hands slide under her dress, feeling her skin tremble under my touch. I lifted the dress slowly, undressing her piece by piece, feeling a deeper closeness, and started pressing hard and fingering her. “God, I love the way your fingers feel – don’t stop.”
Every breath she took, every soft moan, it pulled me deeper into her.
She undid my T-shirt, her fingers lingering over my chest before she leaned in and kissed. The bed was firm, and the air around us heavy.
We didn’t talk much – we didn’t need to. It wasn’t just sex. It was instinct, chemistry, and something neither of us had expected with strangers. We were both far from first-timers, so we knew what we wanted, and what we needed to do. I slipped the condom on, and teasing her slowly, tracing the edges of her thighs, letting my cock do the talking….
“Harder… don’t hold back now,” she gasped, her nails digging lightly into my back.
That one line flipped a switch in me. I gripped her tighter, matching the rhythm of our breath, our bodies now fully in sync. Her legs wrapped around me, pulling me deeper, her moans rising with every thrust.
All I could focus on was the way her body responded to mine. The way she arched her back, the way she whispered my name like a secret she couldn’t keep.
She looked into my eyes, biting her lip, and whispered, “Right there… stay there……….ahh”
It wasn’t just lust – it was a release of tension, of craving, of everything we’d held back in words. And when we finally collapsed beside each other, drenched in sweat, still catching our breath, the silence between us wasn’t awkward.
It wasn’t just sex. It was the kind that makes you forget what time it is, where you are, or whether the rest of the world even exists. It was rough and slow, fast and soft, urgent and careful – all at once.
“Look at me when you touch me. I want to see it in your eyes.”
“I don’t want gentle tonight. I want you raw.”
“Now tell me… what haven’t you tried yet, but want to?”
“Next time, I want to take control. All of you. No rules.”
“Let’s not wait next time. No coffee, no talk. Just you and me.”
She turned to me and said, “I haven’t felt like this in a long time.” Neither had I.
I’ll share more of those moments – the details, the emotions – in the next part.
Would love your honest feedback on the tone, flow, and overall feel.
Let me know what works and what doesn’t! Email: [email protected]