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Heretochillx 25-04-2025 03:41 PM

(Story) Have You Ever Wondered
 
[Slow burn, work of fiction]

Do you ever find yourself wondering, in the course of your everyday life, about the women who cross your path?

Maybe it’s the neighbor who doesn’t wear a bra when taking out the trash. Or the moms of your kid’s friends, always in those tight, flattering yoga outfits. Maybe it’s a coworker — the kind you get to interact up close and objectively rated her a solid nine — or a stranger who locks eyes with you for a fleeting second.

And in that moment, quiet and unspoken, do you ever wonder… what it would take to sleep with her/him, if the opportunity ever came up?

These are a series of stories about those moments and what comes after.

Before our meet up last Friday, I already had a feeling there was something different about it. Alison is a coworker who I’ve been working with for the past five years. I have so much fantasies about her because she is my cup of tea/vege. I had not made any moves as office romance is almost never a good idea. Last Friday we decided to try out a new bar that night that we had been talking for a long time.

Alison and I occasionally saw each other outside of work, usually at team bonding dinners that sometimes turned into late-night hangouts with colleagues. We both enjoy a good bottle—whether to unwind, loosen up, or simply to enjoy a conversation with good company. And sometimes, after a few more drinks, those conversations took a different turn—especially when we were the last ones standing after everyone else had called it a night.

We had been talking about visiting this speakeasy bar in Joo Chiat forever and finally decided to make a reservation to go last Friday. It was not the first time we met up for drinks, but I felt there was something different about this time. On my end, I paid attention and planned for what to dress in advance to hopefully impress her. I didn’t want to overdress for the occasion and to put her in an awkward situation the whole night. So, with that in mind, I casually prompted her in WhatsApp with a celebratory tone that the place warrants good outfit to match, and she responded saying she has already got a nice dress in mind. Somehow, I felt that we were in-sync for our intention but I wasn’t certain. Typically, we would ask colleagues to join but none of us suggested that for this Friday, but I knew she would happily welcome the idea if I were to suggest. I chose not to do that this time and she didn’t as well. The vibe before leading to Friday felt like a date night, but I tried not to see it that way, I guess it’s a way to put a distance between our relationship, she is happily married with a boy.

Heretochillx 25-04-2025 05:37 PM

Re: (Story) Have You Ever Wondered
 
It took forever to finally arrive on the day - Friday. I managed to clear my work early so I can go home to prepare for the evening. The whole day has been fueled with excitement that I could not explain, it’s really not the first time we met for drinks and other than some steamy conversations we never had anything beyond, did I want more? Yes. Did I fantasize doing it with her, absolutely. What stopped me from even suggesting it to her was we had been talking like friends, never flirted, and She also never showed she was attracted to me in any way. You must be thinking I was being insensitive. Believe me, I would know. And…she is happily married and a caring mom to a cute little boy. Even hinting at that feels too disrespectful to her. Worse, she might see me differently, and our relationship could go south.

I arrived early at the speakeasy bar, sitting at the lounge waiting for Alison. Tend to adjust and check on my outfit every now and then to make sure they were impeccable. I wore a navy linen jacket with a dark brown shirt inside. I chose the material carefully so they are cooling and airy considering Singapore’s climate. It’s hard to do layering in this warm and humid climate in order to give out that visual impact without sacrificing comfort and getting warm and sweaty inside. Linen garment is the solution. As for the bottom, I paired the top with a tan chino and a brown suede chukka that scream masculinity. With the new Tudor dress watch and a fresh haircut, I felt like a million-dollar buck. As the clock ticked closer to our meeting time, I was feeling anxious and excited, while keeping a look out for her, I saw through my peripheral vision that someone was walking towards my direction, I turned to face the person straight and it was Alison who showed up in a nice darker tone olive dress, , she looked gorgeous in that dress, it draped nicely and followed her curvature, she has quite an impressive physique considered her busy work life. My heart was racing while greeting her with a warm hello and a gentlemen hug. Her perfume for the evening was refreshing and feminine, so addictive, her skin was smooth to touch and her slim body felt I could crush it easily. I had a little hard on down there for a brief second while staring into her sparkling eyes. Her grin made me melt.

After exchanging a few words, we then headed towards the waiting counter to be seated in. I gestured her to make a move first and I’ll follow suit, and while walking right behind her, I had a clear view of her back and I swept unapologetically, her dress has a bareback opening that showcased her fair and silky-smooth skin, wait a minute…, she didn’t wear a bra, and her tight-fitting silhouette from her waist down meant she had to wear a thong for the underwear line not to be shown. My heart was racing or even blushed when I thought of her melon C cups just hanging there bare and open, perhaps with some nipple covers stuck on. My firmness down there increased.

We enjoyed the speakeasy bar, it was nice and has a cool theme, we got out around 2 hours later, a little tipsy from a couple of cocktails but the night was still young. We moved to a nearby roof top bar after researching a little in Google maps. As we chat, she opened up the private side of herself while sipping a glass of cognac. I have taken note of the Cognac name. We exchanged glances throughout, I was really enjoying the moment, we had really good and carefree conversation, we talked about anything, aspiration and dreams, as the alcohol slowly kicked in, our topics got more NSFW and explicit. With Alison sitting right next to me, I could smell all the pleasant scent that coming off her from the breeze that kissed my face, I can hardly hide the bulge in my pants by now.

Our eyes locked and I maintained my gaze with confident and curiosity, she then told me she wanted to do something for some time now that I may not like it, and asked if I’m cool with it, I tried so hard to contain myself, not letting myself to believe she was asking what I was thinking. I jokingly asked if she wanted to punch me, and I said yes nonetheless, while holding her glass, she leaned forward to my face and closed her eyes when her lips were about to touch mine. I reciprocated and we started light kissing, and it got really wet when we transitioned to tongue fighting. I felt all the softness and suppleness of her lips and her breath was nice. I felt my heart was almost jumping out and not sure what’s happening in the moment, lots of thoughts that I had on her flashed back in my mind, and the rational part of me was trying to make sense of the WHY. There were other guests around us and I didn’t give a fuck if anybody was staring, obviously Alison didn’t care as well.

I told her that her lips were soft and she said mine too. We stayed in silence for God knows how long, I guessed we were processing what had just happened, and later when I recalled, it’s more like I was the one who needed to process, where she appeared to be savoring the moments. I asked if she was drunk. She said she was tipsy, but not drunk—she knew exactly what she was doing. I nodded and sat with the silence. I didn’t know what to think. All I knew was that I wanted more…

We finished our drinks sometime after that, and headed down and out. Both of us didn’t feel like going home and to end the night right there and then, so we strolled around the vicinity and continued chatting. It was a nice evening, the weather is cool with occasional breezes, my jacket was still on and I had not broken a sweat. As I walked, there were a lot of questions going through my mind that I wanted to ask Alison but I decided to play it cool, my heart was still beating fast inside. As we walked, what had been breezing turned into a drizzle, we quickly find a sheltered place and dashed into it. We were waiting for the rain to pass in this what appeared to be a small recess area of the building which the other end connects to the other side of the shop lots. The light was dimmed and the surrounding was quiet. My heart was pounding because the setup and vibe in this moment looked a lot like those you will see in drama that ultimately led to a romantic scene.

A few moments later, she turned to me and told me that she had always been wondering how I taste like, and she had the answer now. Did she just tell me that she did what she did out of curiosity? While I was still trying to take it all in, the rain outside had grown rampant and deafening. I could no longer tell if it was the downpour hammering the ground or the fluttering of my heart that was causing the chaos inside me. I turned to look at her, we locked eyes, I mustered up my courage and seized the moment by pulling her in to me and start kissing her, with aggression and passion. She did not resist and responded the same. I held the back of her head and embraced her body with my other arm, I pulled her closer and she could definitely feel the swollen bulge in my pants pressing against her crotch area. The kissing was so good that she started moaning, I stopped to let her breathe and listened to her breathing. She must have realized her own moaning and giggled with embarrassment.

“Shall we?” I asked, intently waiting for a positive response—hoping she understood.

She took a moment and followed by a nod.

“Are you sure?” I didn’t want her to regret it.

“Let’s go,” she pulled me to walk along.

Thanks to how efficiently things run in Singapore, checking into a hotel is quick and easy. I had never been to this hotel in Tanjong Pagar area before, so I wasn’t sure what to expect. It’s a French themed hotel, I guess you know which one I am referring to. As I am typing now, it was all a haze to me for what happened in between checking in at the counter and opening the room door. I could only remember that my heart was beating fast nonstop, and was still in the state of disbelieve that I was really going to fuck her in a short while. I could feel that we were both nervous on how things unfold. I laid my eyes on her, Alison turned to me, and gosh, she gave me this sultry look and I could not stand that. I tilted my head back to look at her ass, her olive color dress just draped nicely and showcasing her round and full buttock, I reached out and naughtily grabbed and hold it a little, she gasped and moaned, obviously wasn’t expecting that. I felt like my pants were getting ripped open down there anytime soon with that serious bulge protruding. She didn’t complain nor even annoyed by my sudden cheekiness, she looked like…she enjoyed and welcomed that act. How could she blame me, she has that kind of ass that made you want to misbehave, beautifully round and firm, it’s screaming for grab. I couldn’t wait to rest my shaft in between her juicy ass and let her do the work.

We stepped into the room; the light was already on and it’s well lit. The decoration and smell were pleasant, the room was spacious and had a long sheer curtain that covered the floor to the ceiling glass window panel. I’m sure you can already guess what I plan to do with Alison in front of that glass panel.

“Hey, I’m gonna use the bathroom real quick,” Alison said, not looking at me.

“Can I join you?” I asked, keeping my tone cheeky.

She paused mid-step, surprise flickering across her face. Then she turned, met my gaze, and said, “In five minutes,” as she walked away, I couldn’t tell if I’d imagined the brief grin playing at the corner of her lips.

I quickly set my things down on the table and slipped into the bathrobe provided. With a few taps, I put on something sensual from Spotify and dimmed the lights, letting the room ease into a soft, seductive glow. I was setting the mood—for whatever come next.

Outside the bathroom door, I could clearly hear the showerhead being turned on. Looking down at my watch, I murmured to myself, “Is it already 5 mins?” I then removed it from my wrist and rested it on the table next to the bed. I pushed open the door and it wasn’t locked. There she was standing in the shower room in her birthday suit. Water shooting her body from the showerhead and her body was glowing. I got an instant hard on seeing what was presented before my eyes and could not believe that it’s happening. I walked my steps lightly and pushed open the glass door to the shower room and stood before her, the water is now splashing on me. Alison opened her eyes and we look at each other for a few seconds, the feeling was strange, it wasn’t awkward, it felt natural. I put my step forward and grabbed her waist, I can see her fair and soft melons bounced before me, I then launched my tongue into hers, we were enjoying the moment, the kiss was sensual and sexy at the same time, my steel hard cock down there pressing against her, our kiss got passionate and we were panting, I took the chance to slid my cock in between her legs, and she didn’t have any public hair, it was cleanly shaven, so was I. When I brushed my cock in between her soft lips down there and drew it out, I looked down, and saw some transparent sticky substance were drawing strings in between my cock and her lips, gosh… she was horny and ready for me. I didn’t let her have it. I took a mouthful of warm water that sprayed out from the showerhead and went down on her. I went straight to her clit and gently eat and suck on it and to let her experience the warmth in my mouth. She held my head and let out a sultry moan with subtle trembles. I can see her eyes were rolling back and lids closed, I took it as she was enjoying the pleasure deeply. In my mind, I was trying to send her the message that I do know some tricks to pleasure, willing to experience sexual techniques and open-minded and absolutely qualified to be her great sex partner. I also wondered if her husband does this to her. I began to work my magic on her, giving her the maximum pleasure through my “tongue-fu”. Not sure if she had any pent-up needs before we met, as she appeared to immerse in this pleasure play very much and her moaning simply made my cock throbbed.

After tongue fucking her a little, we dried ourselves up and can’t wait to move over to the cozy bed for more actions. Before I could climb onto the bed, Alison stopped me, and loosen my rope’s belt carefully and that revealed my still erected shaft, ahh, it’s her turn to go down on me, my turn to enjoy her tongue’s work. It was amazing, the bobbing of her head up and down, the slurping sound and the licking of the tip and looking up face simply made me want to explode all the cum into her mouth right there and then. But no, not like this, I held back, barely, it was so good, the just nice pressure in sucking, and good speed in going up and down and she moved on to my balls as well. At one point, she told me I could shoot the load into her mouth if I wanted to, how can I end this without the main show, no way. I suspected that she knew how good she is in giving blowjob.

After a good few minutes I was afraid that if I didn’t do something, I’ll just surrender my load to her, I grabbed her arm and told her that if she was ready to let me fuck her. While undressing, she looked at me with wetness around her mouth from her tremendous work down there. Right after she let her robe dropped straight to the floor, I pushed her to the bed with her back facing me, I leaned forward and pressed down on her, kissing her ear and neck, my rock-hard shaft is poking at her clit. I asked her softly if she had any condoms, she said no, she didn’t plan to get this far, I said neither did I. Alison asked if I’m clean, I said 100% since I’ve just got my health screening report, she said she hasn’t been sexually active and free from any STDs. I guess we were still trying to maintain our cool to have the precaution check given the heat at that moment. She said she will take Plan B before I thrusted in as if she could read my mind about the worry on pregnancy. With those out of the way, I felt like my senses were enhanced, I could smell her pleasant body scent, from her skin, from her hair, I felt like my shaft was burning and Alison was the water tank that could cool it off, I aligned my cock nicely, with a quick finger touch, I can feel the wetness at the tip of my finger that she was ready to fuck, I inched forward, and slowly slid it in, she let out a soft moan, as my tip was entering, I experienced the full sensation of her tightness, and wondered how can she be so tight as a married woman and a mother, as I slowly entered, I felt like entering rings of ribbed wall that was warm and wet, I penetrated gently. I used my both hands to spread her full and round buttock to give me a better angle to get deeper, Alison knew what I was trying to do, she moved herself slightly, and sat backward a little, with that move, I felt I have reached and hitting her deepest spot, she felt the same and gasped. It was such a wonderful feeling and sensation that your cock is fully wrapped. I asked if she was alright, she said don’t stop there. With her permission, I increased my speed progressively, with each thrust, she looked back at me biting her lower lip, she looked like she is in pain but I knew she was enjoying every inch of my cock and each stroke that I gave to her. I varied my speed and be careful not to finish too early, the action we had earlier had already put me on the brink of cumming all over her, guess she liked what I had to offer at that moment. The sound of our skins slapping when my hip hit her buttocks was simply musical, together with her sexy moaning I just wished this would never end. Each stroke that I pumped into her awoke all the sensitive cells of hers and mine, each wet thrust gave out a very clear watery schlick repeatedly. We were both panting, and her fingernails sank deeper into my arm I was using to hold her. She is tsunami level wet.

While still pounding her, I took a second to look down, I slowly pulled my cock that had plunged into her great depth, when it was gently pulled out from her juicy slits, a good drape of glossy love juice clung and wrapped onto the cock entirely, I was amazed by how wet she was, was I really that good? When I pulled the last bit of the tip out, Alison gasped again. A few drops then hit the bedsheets from my tip while it pulsated.
Alison turned around and gave me the sultry look as if she can’t wait to have more of me. I gestured in a way that ask if she felt adventurous to go to the window panel, she hesitated but slowly crawled out of the bed nonetheless with that strong come fuck me look.

“Can you spread for me?” I whispered gently while guiding her to allow me pressing her against the window. For privacy, we kept the sheers on and were still able to lookout to the Shenton Way district with all the colorful lighting emitted from the buildings.

She nodded while slowly spreading her legs outward like the letter A.

I used my fingers to swipe in between her legs and to rub my cock with her wetness. I adjusted myself and angled in slowly; she could feel all the sensation when it’s inching in. This position allowed me to have the tightest possible contact, I don’t have a long cock but it is rather thick, I wanted her to experience the whole of it.

She requested for a faster pump and I happily obliged her. I felt my crotch area was a bit cold, and that was because her generous supply of love juice has spread all over that area and felt cooling when the 18-degree Celsius aircon blew air through them.

I could not hold off any longer, Alison was moaning like crazy and kept telling me to keep going, if there were people walking outside our room, I have no doubt that they can hear her moaning in waves clearly. The moment has come, I asked where can I shoot to, she said inside, I asked again to confirm her order if she really would like a cream pie and she said yes, I exploded everything into her and with what must have been a good month of storage, I gave her a strong 7 or 8 loads before I felt I have emptied my tank; I withdrew my cock slowly and it didn’t disappoint me which I got to watch how my cum slowly dripped out from her lips and on the floor. Alison turned around and with no hesitation kneeled down and went straight to my pipe and gave it a good cleanup using her tongue. That was simply out of the world experience. We lay on the bed, resting, feeling extremely satisfied…

strout 26-04-2025 04:55 PM

Re: (Story) Have You Ever Wondered
 
Fantastic start TS. More please!

meijipcc 26-04-2025 08:18 PM

Re: (Story) Have You Ever Wondered
 
Nice story, camping for more.


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