Casual Hookup With A Colleague

Mail me on [email protected] for any queries, advice or friendly meetups. 😉 So let’s start our sex story.

Twinkle is her name, is the secretary of our office, a large corporate sprawl set in the heart of the city. Twinkle is a regular middle-class girl, always dressed simply. She isn’t very good looking, a bit on the heftier side. Her stats would be roughly about 34-32-36, and since she was only 5 feet 2 inches tall, these stats gave her strangely an attractive shape, mainly because the assets spilled over a bit in whatever she wore, which was mostly salwar kameez.

She is dusky in skin tone. She must be in her early 20s, never bothered to confirm it though. I did know she is single and always in a positive mindset at work. Which I rarely was, cos of the workload. She always managed to smile every time she passed me. I never bothered to notice if she did that for others, but I didn’t care. I was in a relationship for past 5 years and just had a breakup, that added to my workload, made me crankier and less friendly to all around. But Twinkle saw past that, she would never fail to greet or smile.

I once passed her in a pantry, I was having coffee and she was seated there eating some fried snacks, guess that explained her figure. She greeted, as usual, I smiled back. She then asked if I was fine.

I asked her why she asked me that, she instantly replied saying I seemed low past few days.

I thanked her for noticing and said it might be the workload.

She offered me some snacks, I moved ahead and took a piece. She asked why I am not sitting.

It was around 5 pm and the workload was a bit less today. I took a seat opposite her.

We then spoke casual stuff, the stuff you make small conversations with, like where do you live? How do you commute? etc..

She then asked me if I was single, I responded by explaining my recent breakup.

I asked her the same, to which she said she was single. I started getting a hint that she was interested in me. But I wasn’t even remotely interested in her, but I was enjoying the attention. It seemed cute.

She then got up to get a coffee for herself from the machine, I then observed her ass. She was gifted in her assets, she’d be a handful in bed. My previous relationship was with a skinny girl.I then thought to myself that I’ve never been with anyone like her. She came and sat down.

I asked her what time she gets off work today, she said 6:30 or 7 pm. She asked me the same, I replied “7 pm”. After this I was running out of things to ask her, she was getting a bit shy too to make small talk. I had set the idea in my head, as to what it would be like having this girl in bed.

I then asked her number, she instantly gave it and took mine too. We saved each other’s contact numbers. She was peeping into her phone, she then asked me what my Whatsapp DP meant, I told her it’s a quote from a book. I went to see her DP too, which was her in tank top t-shirt and jeans and posing with her friends.

I messaged her on WhatsApp itself, saying nice DP. I have mostly seen her in salwar, and on weekends she does wear casuals, but not such tight tank tops.

I then messaged her saying she should dress up like this more often. She was blushing, then she looked up at me. She said she mostly dresses up like this when she’s out with friends, and worries to dress up in casual cos of strict work rules.

After a while, we both took leave and went to our desks. At around 6:30, the office started clearing up. She messaged me saying that she’s waiting till 7, so we can leave together. At 7 pm we both met at the front desk and left. We spoke quite a lot, our routes were apart, but we walked to a fast food joint and had something and passed our time.

Around 8 pm, we parted ways. At night, we started messaging each other and chatting.

We started harmless flirting with each other, nothing exotic or alarming. This continued for few days. It was one Friday, which is the beginning of our weekend, we started chatting at night from our respective homes. I asked her as to what she wears at home, within few minutes she sent me a selfie from a mirror. She was in a blue tanktop, with a black legging.

She asked me what I was wearing, I sent a pic of me in a t-shirt and three-fourths.

She then jokingly replied that I should wear this more often, clearly she was joking about what I said to her the other day. We continued chatting, she asked me about my dinner, I told her I ordered it from outside. I live in a rented flat sharing it with my cousin, and my cousin wasn’t home that night. After a while of more chatting, I asked her to send more pics of hers. She asked why. I said I just want to see more of her. She sent a blushing smiley. She then said she would like more pics of me too.

After few minutes I got 2-3 pics of hers, she was in the bathroom and posing fashionably, pouting her lips. I sent few pics too of me making funny faces.

I complimented her that her supermodel poses are superb and that she should think of it as a career option. She was LOLing! I then asked her to try out a bikini and let’s see how she looks in that. She said she doesn’t have that. I then suggested “Lingerie”. She didn’t have that either, not that I was expecting her to have it either, I was just taking the conversation further.

I then messaged her, “Ok, just normal pics in undies will do… :P”

TWINKLE: Shutup!

ME: Hahahaa, kidding re! Anyway, what color underwear are you wearing now? 😀

TWINKLE: Oh my god! You’re mad kya! I’ll kill you.

ME: tell na.

TWINKLE: seriously?

ME: Yes

TWINKLE: You’re an idiot! White and black.

ME: White what and black what.

TWINKLE: Oh god!. White bra and black underwear.

ME: Hmmm…

TWINKLE: Happy?

ME: Yes. M already imagining you in it….. Hmmmm

TWINKLE: I will kill you.

I then sent her a selfie of me on the bed, without a t-shirt, and lowering my pants a bit, not revealing anything.

TWINKLE: What??? My god!

ME: what happened?

TWINKLE: hmm. It’s a nice pic…

ME: thanks. Want more?

TWINKLE: Yes. 🙂

I sent her a pic of me only in the underwear now.

Just then I got a pic of her in white bra.

I complimented her, it was stunning. I then sent her a pic without the underwear, but my hand covering the crotch.

TWINKLE: Oh god.. this is nice, but remove the hand na.

ME: Why?

TWINKLE: I want to see it

ME: come here and see a.

TWINKLE: Can’t now. Too late to get out. Tomorrow we’ll meet?

I agreed. I then asked for her pics, to which she said, let’s keep it for tomorrow.

Next day, my cousin wasn’t home then too. I got her home. She went around to see my place and loved it. I was very neat for a bachelor.

I then held her from behind and started kissing her neck. She turned around.

We then stared into each other’s eyes and moved closer to kiss. We french kissed for a long time, salivating in each others mouth.

I then made her lie down on the bed, She then told me she’s a virgin. I responded by telling her I’ll be gentle with her and save the roughness for a later day.

I got her undressed, she helped me undress too. I went to play with her breasts, pinching the nipples and sucking them, occasionally biting them a bit. She moaned a bit. I then moved down to her crotch, with one of my hand still pinching her nipple. I started licking her pussy. My tongue flicking it, also occasionally rubbing my finger too. She was moaning loudly now, getting more restless, she pulled me up to kiss me, we kissed more. I was playing with her breasts.

She reached out for my penis and started stroking it, I stopped her. She asked if I had a condom, I said yes. I then took it out and wore it. Gently I pressed the head of my penis on her pussy. Slowly inserting, she was moaning loudly. It didn’t hurt her terribly, but slight pain. I pushed it gently inside, she was writhing restlessly, I calmed her and told her to trust me, I slowly thrust it more inside, she was writing more. I then pushed it inside a bit more and started stroking it, she was restless, moaning louder and the pain had subsided. She was now completely dazed.

I took long strokes, kissing occasionally, We lasted in this position for 6-7 minutes, then moved to doggie style, which had her co-operation in terms of movement. After few minutes we returned to the missionary position, where we both were moaning loudly. I kept thrusting inside her. She had already gotten her share of orgasms. I requested her to let me know when she is close to another one. As I was feeling the pressure building within me and I had to cum.

After a while, she yelled, “I am close, ahh, baby I am close,” I increased my speed and started thrusting faster till we both stopped moaning and collapsed. We were now in a tight embrace after having achieved mutual orgasm. It was a satisfying experience. We both got dressed and went out to eat something.

After a while, we returned home and began another session of crazy sex.

After this, we hooked up a lot. Neither of us ever made our affair public in the office and we behaved casually. We never spoke to each other for the nature of our relationship, we had both accepted it as purely physical. She later revealed that she had a crush on me and was planning to flirt with me for a casual hookup, but she never had the guts to it.

She then got into a relationship with a friend of hers and we stopped hooking up. Until one day when she was feeling low as she had got into a fight with her, we got in touch and had sex. It wasn’t planned but happened incidentally considering our history together. That was the last time we hooked up, we avoid it completely now. She has gotten better in bed now, I take full credit for that.

Since our first time, she has even started getting better at blowjobs, which is a skill I feel most girls lack. Thanks for reading my sex story.

About Abhilasha Bakshi

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