Chilly Holidays, Steamy Bets – Part 1

Hey Everyone, I’m Krish, a 29-year-old guy from Hyderabad now navigating life in the USA. I’m back to share another incident from my life during the holidays.

Before I delve into the story, I would like to thank every reader who took the time to read my story and all those who pinged me.

Coming back to the story, this happened during the Christmas holidays. As I was bar hopping, I met a woman. I bumped into her thrice and taking a third time’s a charm, I approached her. The third time was lucky for me, which formed the reason for this writing.

Let’s begin from the beginning. I recently moved cities due to a job change. This was my first time far from my friends and acquaintances. A new city and a new adventure. But it was a journey where I was alone after a very long time. I didn’t know anyone in the town, neither friends nor readers or anyone.

Even Tinder wanted to avoid helping. After settling in and getting into a groove, the holiday season kicked in with Thanksgiving. I was alone and had nothing to do. I started working on myself and joined group classes, slightly diverting my mind.

The Christmas weekend came. The gym where I worked and attended classes was closed, and my gym/ class partner was out of town. That left me with an acute pang of loneliness amidst the holiday cheer. I decided to go bar hopping on Christmas Eve to shake off the boredom and the chill of solitude.

Putting my best foot forward, I checked the Google reviews for hope. My first stop was a cosy bar with warm lights and a festive atmosphere. That’s when I noticed her, Aditi, the star of this story.

Aditi was with her friend, with her eyes bright and wide open. She was leaning on the bar counter, tapping her fingers like a musical instrument. She looked cheerful and was vibing to the music. While she was busy in her world, I checked her out.

I don’t know what, maybe the alcohol or my loneliness or what pushed me towards her to have a conversation. She turned towards me with the drink as I approached her, almost bumping into me. We both profusely apologized to each other. That was the first time Aditi had seen me for the night.

Missed opportunity. I moved away and just stared and enjoyed the quick glances of her from afar. Getting bored, I left the place for another bar. This one has a more German vibe.

Cosy music and an excellent ambience for conversations. I bumped into Aditi again, or rather, she bumped into my back. I picked up my drink and took a step back to have my back touching something. I glance and see a person. I blurt out a sorry as I turn around to see her again, Aditi.

“Second Time is magical,” as a few say, holds true even in this case. Her eyes lingered, a hint of recognition as our eyes met, bringing me hope and courage that I could approach her.

Before anything could happen, I felt a pat on my shoulder. A friend I knew was visiting my city and didn’t know I moved there recently. Cursing my luck at the lost chance, I continued conversing with him for a while. Then, I headed to a couple of other bars as the night fell.

I finally saw her again after a couple of hours and multiple bars. This time, I approached her at a more lively pub, sitting alone, bolstered by the night’s spirit.  I walked towards her. Her eyes widened in curiosity and fear.

Sensing that she might take me for a stalker, I tried to present a pleasantness in my smile and approach. “Third time’s a charm, many say. But I didn’t believe in it until today when our paths crossed thrice,” I said. I stood beside her to start a conversation.

I have no idea what she will think of me. Throwing me back to my early 20s, a bundle of nervousness when approaching a woman.

Before she could say something, I continued, “Normally, I might ignore such a coincidence. But tonight, it felt different. Your eyes were beautiful and magnetic. I couldn’t resist them.”

Slowly, I could sense my confidence growing, evident with a slight smile on her lips. I then asked if I could join her, to which she obliged. Thus began our night as we exchanged pleasantries and details about ourselves.

“Hi, I’m Aditi,” she replied, extending her hand. I took her hand, feeling a jolt of connection.

“I’m Krish. I wondered if I’d need to bump into you a fourth time to converse.” Her laughter was genuine, and it made me more comfortable. We spent the next few hours talking. It wasn’t just idle chatter but a meaningful conversation that flowed effortlessly.

I learned about Aditi’s love for classical music, her work as a graphic designer, and her passion for travel. She was more than just a pretty face. She was someone with debt who laughed wholeheartedly and shared intriguing and endearing stories.

I also learned about how people often confuse her origin. She is a Srilankan-American, but people often assume her to be Indian-American. Her past relationships and what she is currently looking for in a relationship and a guy.

“So, Krish, what brings you out on a night like this? Avoiding Santa’s naughty list?” she teased, her eyes twinkling with humour. Finally, breaking the ice or the unseen barrier of formal conversation.

I chuckled. “Well, I’m new in town, trying to make my traditions. And apparently, stumbling into intriguing strangers is one of them.” I found myself drawn to her vibrant personality and quick humour.

“You know, for someone who’s just moved here, you seem to have a knack for finding the most interesting spots in the city,” she noted, sipping her drink.

“I guess I have a good guide now,” I replied, giving her a playful wink. “Maybe you can show me more of the city’s hidden gems?”

She raised an eyebrow, a smirk playing on her lips. “Only if you promise to keep up. I don’t slow down for tourists.”

I grinned. “BTW, tonight, I’ve discovered the most interesting spot in the city.”

“Oh? And where’s that?” She played along.

“Right here, talking to you,” I said smoothly.

Our back-and-forth banter continued. She started to open up, as did I. All of this was interrupted by the waitress who had come to our table to inform us that they were closed.

Disappointed that our night had to end abruptly, we paid the check and left. Outside, I was expecting the goodbye hug and farewell, never to be seen again. Planning quirky or smooth ways to ask her number, I was standing there still when she spoke again.

“I can’t believe how late it’s gotten. I should head home.” There was a pause, a moment of hesitation. I didn’t want the night to end just yet.

“Would you like to continue this conversation somewhere quieter? Maybe at my place? I could whip up some hot chocolate,” I blurted, hoping I wasn’t being too forward.

She stood there unmoved, and then her face broke into a warm smile. “I’d like that. How about I do something even better? Hot chocolate with vodka? I’ll show you how it’s done at my place?”

Her counteroffer took me by surprise but in the most delightful way. We left the pub together, the cold night air feeling less biting as we walked side by side.

The walk to her apartment was filled with light touches and laughter, each step building the tension between us. Her hand brushed against mine, a seemingly casual gesture loaded with intent.

As she unlocked her door, she turned to me. A playful yet seductive smile on her lips. “Ready to see how I make my special hot chocolate?”

I nodded with a bright smile as we stepped in. I got comfortable as Aditi entered the kitchen to prepare the special hot chocolate.

Her hot chocolate contains cocoa powder, unsweetened dark chocolate chips, velvetized chocolate cream in 1 cup, absolut vodka in 1 cup, and milk. The process was simple, but the drink was strong.

She made a lot, which meant we were up for an all-nighter. The first few rounds were slow, with small sips and many flirtatious conversations, teasing filled with laughter. We got comfortable with each other as if we had known each other for a while.

I want to remember which round it was when we started to play the game. Who could chug it down fast? We both won alternately and the tie-breaker, we won’t agree on who won.

But seeing the bottle rolling reminded me of truth or dare and how one such truth or dare led me to have a memorable night in the past. Seeing me chuckle, Aditi asked me, “What happened?” I replied, “Nothing, ignore it,” but she persisted, and finally, I gave in.

Maybe the buzz or I don’t know what, but she wanted to play the game now. Without any resistance, I gave in. But I did warn her that she might not be comfortable with everything I asked and might give up. Mocking me, she sat opposite me, and we started the game.

The usual icebreaker questions happened at the start, which took a sharp turn when I asked her, “When did you lose your virginity and with whom? ”

“With my ex-bf when I was 23 years old,” she replies without flinching. Following it up with “What about you, Mr?”

“With my classmate when I was 19 years old,” I replied

That led to a string of questions in the realm of sex, a few of which were
1. What’s your body Count?
2. When was the last time you had sex, and with whom?
3. FWB or ONS: what do you prefer
4. Cum inside or on the body?
5. With a condom or without?
6. Anal sex?
7. What are your turn-ons and offs and fetishes?
Etc etc.

This discussion went on and on and allowed us to explore the sexual side of each other, learning more about one another. Finally came the question, which led to an adventure unimagined.

“What was your longest session?” she asked.

“I don’t remember exactly, but maybe 45 minutes once was my longest,” I said quizzically.

Upon hearing that, she burst into laughter like a maniac, which took me back and hurt my ego.

“What?” I asked.

“Nothing, leave it,” she replied, trying hard to control her laugh.

“You don’t believe me? Come on,” I asked.

“Dude, I thought we were playing truth or dare,” she says sarcastically.

In a severe tone, I say, “Is that an invitation to prove you, huh?”

“Oh, come on, you won’t last five minutes if I blow you. Forget 5 minutes of fucking me,” Aditi counters with pride in her eyes.

Filled with rage, I sat straight, looking dead into her eyes. I say, “Fine, make me cum in 5 minutes. Whatever you name it, I shall do it, no questions asked. But if I win, then what?”

I could see the smile on her face fade, and she also got into a serious mood.
Thinking momentarily, she stares at me from top to bottom and then says, “Okay, fine. If I win, then you better be ready to go viral. If you win, then you can fuck me for life.”

Shocked at the offer, I agreed without a second thought. Also, to taunt her, I said, “Not 5, let’s triple it to 15 minutes. If you can make me cum in 15 minutes, I will do whatever you say. If not, then get ready to become my fuck toy.”

The pride and ego in either of us is at its peak. Aditi, in her t-shirt and jeans with her hair flowing over her shoulders and back, pulled it together to plait a pony and further wrapped it in a bun.

She looked desirable as she was doing it, making me stare at her. It eventually caused me to have a boner, which she noticed and smirked. I was unsure what was happening in her mind. But I was determined to win and teach her a lesson. I wanted to win to boost my ego.

Standing up, I started to unzip and get into my boxers. Signalling with my head, I ask her if the sofa is good enough. She signals it’s okay, so I remove my boxers and sit on the sofa with my legs wide.

Aditi comes and settles between my legs. She looks at my dick which is semi-hard and already oozing pre-cum. Smiling as I guess she thinks her work is half done, she looks at me.

“Is this okay, or do you need anything else, Sir?” she asks in a husky tone.

“Sure, remove your top. Let me see what I’m signing up for,” I reply.

Removing the t-shirt, she throws it away, revealing her dusky skin-toned boobs in a black t-shirt bar. The view of the cleavage and her dusky skin tone and clean armpits were enough to raise my dick and salute her.

Picking her mobile, she opened her time, set 15 minutes 1 second, and pointed it to my face. I gave a nod as she pressed the start and pushed it aside. She caught my dick with her hands.

Aditi’s sudden action of catching my dick made me jump in my seat. But I settled quickly as she started her game plan. Aditi started stroking my shaft and running her hands on the entire length of my pole. She started moving the foreskin up and down vigorously, making me moan and shout in pain.

She started giving me a hand job in a blink, and you miss pace. Slowly she moved her mouth and face close to my dick. She started kissing and licking the end of the shaft region, which caused a ticklish sensation in me. Going along the length, she was licking my precum and the shaft, making it wet and slurpy.

While her one eye was constantly checking out the time, her hands and mouth were fixated on my dick. Licking the mushroom tip, she circled the top and inserted her tongue into the opening on my dick. Time passed, and my moans got louder. But nothing was happening, and she was getting desperate.

A seductive dance between her lips and my tool occurred. Each gulp and lick caused a tantalizing embrace in me. Aditi’s grip on my dick started to get firmer over time. Her forehead started to show her worry. Yet she was determined and started to take my dick deeper into her mouth, making her gag.

Increasing the intensity and the vigour, she moved her head even faster. At around 10 minutes, I guess she stopped and paused the timer. She looked straight into my eyes, with her hand still wrapped around my dick.

“Dude forgot to ask, do you like to touch me when I’m blowing? Is that something you do?” Aditi asked, wiping her mouth. “Okay then, go ahead,” she continued as I nodded in affirmation.

Resuming the sucking and the timer, Aditi was even more aggressive. I slowly bent over and started to touch her boobs on top of the t-shirt she was wearing. They were massive and firm. I started to play with both her boobs on top and from inside the t-shirt, touching the bare skin.

Though that excited me and made me more horny, it didn’t help her cause. Finally, the timer started to beep. I had a bright smile while she had her face hung in defeat. I smiled and said, “Tough luck,” as I didn’t want to rub it in her face.

Aditi was graceful, stood up, congratulated me, and asked what I wanted to do. I looked into her eyes and said, “Well, you gave me a blowjob, which I would rate as one of the best and most exciting I ever received. Let me return the favour now.”

Saying that I jump up and push her down on the couch. I pull her pants down along with the undies and pull her legs wide.

That’s it for this one, folks. What happened next I shall write in the second part. Until then, have fun, and please feel free to write feedback or comments to [email protected].

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