I Didn’t See This Coming
My name is Sean. I was just a simple corporate employee doing mundane paperwork and attending lots of meetings. Most of my relationships were with younger women until I met Jessie. I wouldn’t actually call this a relationship, because Jessie was married with a six year old son. Jessie was in her late 30s, but kept her figure well (Not the skinny type. A bit fleshy, but still appealing.).
Both Jessie and I worked in the same company. Being employed in a MNC, you don’t get to know everyone. Only after two years, then I got to know of her existence unintentionally during our corporate retreat at a chalet in Changi. Jessie was a member of the organizing committee.
As most of our colleagues were trotting off to happy hour at one of the drinking hole nearby after the retreat, I saw a lone soul looking rather flustered trying to tidy up the area.
Being helpful, I walked over.
Sean: “Need any help?”
Jessie: (Looking up from her squatting position.) “That would be great! But aren’t you going to join the rest for happy hour?”
Sean: “Nah… It is okay… Plenty of chances. Oh yah… My name is Sean, I am from the business planning department. Nice to meet you.”
Jessie: “Hi hi, I am Jessie from HR. Nice to meet you too!”
Sean: (Rolling up my sleeves.) “Okay! Where should I start?”
Both of us managed to get the place tidy up in about an hour or so, I also got to know a little about Jessie. She recently returned to the workforce after her son began primary school. While her husband was doing pretty well to live comfortably, she didn’t want to rot at home.
Sean: “It’s pretty late, I will give you a lift out. Where do you stay?”
Jessie: “It’s okay. I am staying in Boon Lay, will be too troublesome for you. I will grab a cab on my way out.”
Sean: “Not at all, I am staying at Jurong West, can drop you off on my way back. Mai shy, let’s go. Here very difficult to take cab also.”
From that day onwards, the ice broke, small talks if we happened to see each other in the building and slowly proceeded to messaging over the computer and phone. Aware that she was married, I was happy to keep this friendship as it was. Until our company’s dinner and dance.
As the only child in the family, I liked how Jessie portrayed herself around me like an elder sister I can go to with my problems. By the way, she was nine years older than me.
However, our company’s dinner and dance changed my perception of this friendship. And the direction where it was heading to.
While there was no lack of SYT’s in the company, my heads and probably many other colleagues’ too, steered towards Jessie the whole night. Dressed in a one piece body fitting black gown and a pair of matching heels, she almost stole the limelight. There was this air in her that had me fixated on her unknowingly. Nothing revealing about her gown, but it just fitted perfectly on her. Perfectly alluring.
A handful of colleagues tried to invite her to dance, which she declined. Seeing I was sitting alone at the table, Jessie walked over.
Jessie: “Any of the babes caught our Sean’s eyes?”
Sean: “You loh…!”
(She smacked me lightly on the forehead and giggled.)
Jessie: “Haha! Don’t joke. With so many xiao mei mei around, trying to suan me right?”
Sean: “How would I dare to suan my dear Jessie jie?! Some of those xiao mei meis can’t even hold a candle against you. You look really gorgeous today.”
Jessie: “So sweet!”
With that, we carried on with our chat and offered her some red wine. I noticed some of the guys looking over with envy. A few of them still tried to invite her for a dance, but continued to get rejected by her.
As the event was coming to an end, I plucked up my courage to invite Jessie for a dance.
Sean: “Jie, can I have the honor to have the last dance of the night with you?”
Jessie: “I thought you’ll never ask.”
With no further encouragement required, I held out my hand to lead her onto the dance floor. Felt triumphant deep in my heart seeing the rest of the guys stared with jealousy as we swayed along the slow number. I held her by the waist, she placed both her hands on my shoulders, around the neck. I was smitten and stirred. My little head that was.
As the dance floor got crowded, we ended up holding each other closer. Both our bodies met. Impossible to hide, I was pretty sure she felt my hard on. I tried to act normal, but squeezing in the crowd didn’t really help. I gazed at her as her head was leaning on my chest. I can see her cheeks blushed. Probably the red wine, I thought.
The slow number stopped, the event ended. While some of my office kakis headed out for more party in town, I drove Jessie back home.
Jessie was unusually quiet throughout the journey back home. She looked kind of cute with the blush still on her face. I teased her about it and somehow loosened the quietness a little till we reached her place. Stopped the car just outside the main gate of her apartment.
Sean: “Have a good rest jie. You look really beautiful tonight, I mean it. See you on Monday!”
Jessie: “Sweet talk! See you on Monday!”
What happened next surprised me.
As she unbuckled the seatbelt and opened the door, she turned back and gave me a peck on the cheek. “Good night Sean.” She said as she turned to alight from the car.
Instinctively, I caught hold of her hand and tugged her back to the seat. I leaned forward, her head turned back towards me. Our lips met.
Our lips met.
Our eyes locked. That three seconds seemed eternal.
As she pulled away, she whispered…
Jessie: “Good night…”
The car door closed and I watched her walking towards the apartment lobby, into the lift. I sat in the car, with my heart still beating fast.
I knew I was in trouble.
Everything seemed back normal the following week in office, except a few colleagues teasing me about how close I was with Jessie.
Even though my mind was pretty messed up with the thoughts of the night, I did not initiate the topic. Both of us did not talk about that night. It just naturally did not appear in our daily conversation.
Weeks passed, nothing much happened. Nothing will happen, I thought.
In and out of relationships for the last couple of years, spending Friday evenings alone had become pretty common. As I was chomping down the famous fried oyster near Jalan Besar, the message tone rang.
Jessie: “Where are you?”
In my mind, I thought it was quite abnormal for her to message me on Friday. She usually spent her weekend with her family. But I replied her anyway.
Sean: “Having dinner at Jalan Besar. What’s up?”
Jessie: “Alone? Want to meet?”
Sean: “Yah… Alone. Meet where?”
Jessie: “Don’t know. I am at home now. Anywhere you suggest.”
My sense told me something didn’t seem right. Leave the questions for later.
Sean: “I will pick you up in thirty minutes. Call you when I reach.”
Chomped down my last bit of fried oyster and sped to her place.
Sean: “Jie, I reached.”
Jessie: “Okay. See you in a minute.”
A minute that was. From the corner of my eyes, I recognized her walking towards the car. In a simple black tank top and floral skirt, she entered the car. She smelled great. My little head stirred. But something was not right. She greeted with a weak smile.
Jessie: “Sorry to call you on Friday evening. Hope I didn’t spoil your plan.”
Sean: “Jie call, I confirm guai guai come down. Any place you have in mind?”
Jessie: “Somewhere to drink and quiet.”
Not often I can find a place that for drinking and quiet at the same time on a Friday night. Then I remembered my folks were out traveling in Taiwan for the whole week.
Sean: “I know a nice quiet place with plenty to drink. Seat belt on and sit tight.”
This was the first time Jessie visited my house. One of those landed properties in Jurong area. As mine was the last unit of the row of properties, privacy was certainly assured. I settled down Jessie at the second floor balcony and went on to open a bottle of red wine.
It was a breezy night. She sat there quietly sipping her glass of wine. Sitting next to her, I admired her features under the night sky, her body under the black tank top. I had a clear view of her cleavage, at least B I guessed. Was a double B later I found out.
Suddenly Jessie broke the silence.
Jessie: “Sean, am I still attractive?”
That caught me by surprise. While in my mind, I wanted to tell her how desirable she was, I felt I needed to find the most appropriate words for her. I was wrong.
Jessie: (Tears started forming in her eyes.) “I know I am no longer attractive. I know I…”
Before she could finish her sentence, perhaps it was animal instinct, I lunged towards her and planted my lips on hers. She kept her eyes closed, we kept in the position for god knows how long, until she opened her eyes. I lifted myself up and said…
Sean: “You can take this as my answer.”
I could see Jessie‘s blush on her cheek and her heavy breathing. She seemed to be in a dilemma of how all this happened. She looked really alluring at that point of time, under the night sky. I looked at her, deeply into her eyes. I knew no words needed. I moved my lips towards hers slowly. She did not avoid, but closed her eyes. It was a long and sensual kiss, our tongues twirled softly against each other, she moved her hands from the chair to my back. I took the cue and moved my hands to her waist. Not wanting to break the moment, I decided to take it slow.
A short break for a breath, she held my head towards her this time. (Like traffic light turned green.) I moved my right hand toward her chest, softly molding her boobs with her tank still on. She gave out a soft moan. If my little head was not hard enough, the moan probably petrified it. I was sure she sensed the bulge in my pants.
Unwillingly, needing to catch our breaths, we broke away from our kiss.
Sean: “Jie, no words can describe how attractive you are to me.”
A sudden tightness felt on my hard on. Not from my pants. I looked down and saw Jessie‘s hand grabbing the bulge from outside the pants. I was practically dead.
Jessie: (With a smile.) “I believe you…”
Overwhelmed by the pleasure from her touch, I hugged Jessie tightly. She began to rub on my hard on with my pants still on, I feel pre cum forming at the tip. Desperately wishing to be released from the pants.
I started to nibble on her eyes. Licking her neck. That drew her moan out. While one hand continued to mold her soft boobs alternatingly, the other hand unbuckled my belt and unzipped my pants. Naturally, Jessie moved her hand into my pants and grabbed my hard on. With four fingers wrapping just below the girth, her thumb started to rub on the tip repeatedly. I let out a moan.
Like an invitation, she moved her hands up and down sensually.
I pulled her tank up together with her bra and started kneading one of her boobs. My mouth moved towards the other. My free hand moved under her skirt and started rubbing her clits from outside her panty. Her breathing fastened as my finger slowly went under the panty and onto her clits.
While her moan was not loud, the privacy we had allowed us to exhibit our lust without worries. I matched my finger movement with her hand. Our lips back together. With stimulation from my hands on her boobs and clits, she was nearing to her climax. I fastened my finger motion and rubbed on the pink nub.
She trembled and let out a loud moan. Her hips jerked involuntarily and juice dripping down my hand. I kept my finger inside and wait for her to slowly drop her hips back to the seat. I moved forward to kiss her. I was still not done yet.
At this moment, her phone rang.
Jessie walked away to take the call.
As the phone call took quite a while, I had kind of cool down. Not wanting to disturb her phone call, I went back to my bedroom to change my work clothes to my usual berms and tee at home. Also dropped by the kitchen to prepare some light bites, worried that she will feel hungry.
As I walked back out to the balcony, Jessie was back sitting on the lounge chair in deep thoughts.
Sean: “Jie, what’s the matter? Plenty of thoughts?”
Jessie: (She turned her head toward me, I can see a little glow on her face with a weak smile.) “No Sean. Nothing.”
Sean: “I thought you’ll be hungry. Here have some small bites, that’s all I can offer for now.”
Jessie: (Chuckled a little.) “I didn’t know you cooks. Whoever with you will be blessed.”
Sean: “Hahaha… Stop teasing me jie. My eyes only have you.”
Jessie: “Only for now Sean. Only for now.”
I sat beside her on the same lounge chair and shared the food and wine. As I reclined to the back rest, Jessie adjusted herself to lay her head on my chest. She revisited the topic on her attractiveness.
Sean: “You are really beautiful, jie. Do you know how many male colleagues were ogling at you during the dinner and dance? I count my blessing for being the only person that night to be able to dance with you.”
Jessie: “And pressing your hard-on on me!” (We both laughed.)
Sean: “And he is still at attention for you now.”
Both Jessie‘s eyes and hands moved towards my berms. She grabbed the bulge to have a feel and let go. I grabbed her hand to stop her from moving away and guided her to roam the bulge momentarily till she took control of it. As she slid her hand into my berms, I tilted her head towards me. We kissed and our tongue wriggled sensually, enjoying the very moment. With one hand caressing her ears, the other hand went under her tank to cup her breast and was playing with her nipple.
My berms was unzipped and my little bro was already out of it without me realizing. She continued to pump my little bro sensually as we locked in our kiss. I moved my hand towards her clit, but her hand blocked me.
Jessie broke away from our kiss, but her other hand was still pumping my little bro. She sat up a little and gave me a wink. I swore I saw a glitter in her eyes. What came next almost made me climax instantly, if not for my oyster earlier and the wine!
Jessie took in a mouthful of wine and went straight to engulf my little bro with her mouth! The movement was so swift that I can feel the wine as her tongue twirled. I moaned out loud. She continued to give me head and slurping the wine that were still in her mouth. Once the wine out of the way, her tongue came into action. Circling the tip a few rounds and deep throat slowly and back up again. I was in heaven…
As I felt my climax building up, I told Jessie.
Sean: “Jie… Jie… Erg… I am coming… Erg… Soon…”
Hearing that, her head movement fastened, as well as her hands. She took a glance at me and went back to concentrate on working my pending climax. Her eyes. Her eyes looked triumphant. Like she was about to cross the finish line in the race.
I placed both my hands on the head, as my climax nearing I looked up into the night sky.
Sean: “Erg… Erg… Jie… Coming…!!!”
Blast after blast of semen shoot out from my little bro, Jessie took it all in. She continued to lick until the last drop.
Sean: “Jie… This feel so good… I am in heaven…”
Jessie: (Chuckle.) “Only for now.”
I wondered what she meant.
Jessie slowly adjusted herself back to my chest and we cuddled together till both of us dozed off. Only to be woken up from another phone call.
As it was quite late and Jessie couldn’t stay over at my house, I sent her back home. Even though I would love my little bro to feel what it was like inside her. But I knew there would still be chances.
Woke up the next morning for my usual weekend run. My routine for years since NS.
Looking at my watch, 8:07 am. Still got plenty of time before meeting my housing agent at 3 pm later. Was planning to move out of my parents’ house since I now had a better job and better income. Also to have more privacy. Even though I really loved the estate here.
Walking back to my parent’s house after cooling down, thinking about what to have for breakfast. One familiar figure was in front of the gate. It was Jessie!
Sean: “Morning jie! Why are you here? What’s wrong?”
Jessie didn’t speak a word. I quickly ushered her into the house.
Sean: “Jie, had your breakfast?”
She shook her head a little. Looking rather perplex.
Sean: “Give me some time, let me whip something up to fill our stomach.”
As I turned around towards the kitchen, Jessie rushed onto me and hugged me from the back. I can feel the intense heat emitting from her.
Jessie: “I need you… I need you Sean.” (As she hugged me tighter.)
I loosened her hug to turn and face her. Our eyes locked and our lips followed. Sensing her desire, I let her take control. Unlike the previous night, the kiss was long and passionate. In no time, our clothes were off our bodies.
My sweat after my run seemed to have stimulated Jessie much more. She slowly broke off from our kiss and lowered herself kneeling in front of my manhood. It was yearning to be released from the last layer of brief that was still on.
Jessie slid one hand in from underneath the brief and grabbed my manhood. While her eyes were watching her hands were pumping behind the brief intently.
Jessie: “I need this.”
With her word, she swiftly pulled down my last remaining piece of cloth on my body and engorged my manhood into her warm mouth, bobbing her head furiously. I placed both my hands on her head as she continued to blow, trying to control her momentum.
“Damned… This feels good.” I mouthed out my pleasure and I looked at Jessie blowing me like no tomorrow.
She slowed down her momentum, but the pleasure heightened. She would roll her tongue up before taking my manhood in. As she took it in, she will release her tongue by flicking it on the underside of the shaft. I almost ejaculated! Can’t let this end so fast.
Stopped her after a while and seated her on top on the dining table. Spreading her legs, I moved towards her clits. The familiar musky smell. Attacked her with tongue slowly and fingering her at the same time. Jessie was moaning. Not loud, but stimulating. Probably due to her desire and the passion, she had her first orgasm in no time. As she cummed, my mouth was shot with her musky nectar. A squirter! How much better can this get? In my past relationship, I had yet to meet one.
Went forward to hug Jessie and she recovered from her orgasm.
Jessie motioned me to sit on the dining chair as soon as she recovered from her orgasm. From her look, she craved for more.
Giving my manhood a few pumps, she inserted my manhood into her drippy love hole while facing me with ease. We locked in a passionate kiss as she gyrated her hips to take my manhood deep.
Jessie: “Erg… Erg… Erg… Argh… This is good. Sean… You make me feel good… Erg… Erg…”
Sean: “Jie… I… I… Feel goo…od… Too… Jie. I wan…t to. Make yo…u… Fee…el… Goo…d…”
Jessie: “Sean… Erg… Erg… I am com…ing. Erg… Fuck! Fuc…k! Fuc…k!! I am fucking coming!! Argh… Argh… Argh!!”
She shook violently as she orgasmed for the second time. Her vagina walls gripped tightly onto my harden manhood and her squirts created the upward motion to push her up and her body weight pushed her back down. Jessie opened her mouth wide, grasping for air as she continued to be attacked by the voluntary motion.
First time hearing Jessie spoke vulgarities. It kind of turned me on further. To keep the mood brewing, I carried Jessie onto the dining table and pumped her in quickened pace. The whole house was filled with Jessie‘s pleasure moans. Jessie‘s face was now flushed. Turned her around with belly on the table and legs rested on the ground, I penetrated Jessie‘s warm love hole doggy style. I had wanted to do her doggy since the dance. I grabbed both her ass cheeks as I pumped her with strength.
Jessie: “Sean… Sea…n fuc…k me… Yo…u… Fu…ck… M…me… Rea…l… Goo…od… I… Wa…ant. You… Ins…ide… Me… Fu…ck… Erg… Erg… I’m… Comi…ing… Soo…on… Sea…n… Comi…in…g…”
Her dirty talks seemed to arouse me to climax. With all my strength, I pumped her quickly and the feeling to ejaculate drew near. With a few more pumps, both of us climaxed together. Due to exerting too much strength, I fell onto Jessie and hugged her from behind while she lay on the dining table. In the quiet house, only the panting of two sexually satisfied bodies can be heard.
Pulled out my limped manhood, strings of white cum dripped out from Jessie‘s love hole. I got up and carried Jessie to my bedroom, rested her on my bed. Jessie was totally exhausted.
I gave Jessie a peck on the cheek and said, “Jie, you have a rest first. I will wake you up when lunch is ready.”
“That was one hell of a breakfast.” My mind thought as I walked out of the bedroom.
Simple fare like egg omelets with bacon and sausages posed no problem for me. Quickly whipped up the lunch, with sautéed Portobello mushrooms to have a balance diet.
Walked back to my bedroom and saw Jessie still fast asleep on my bed. The picture right in front of me, I thought was rather perfect. Not wanting to disturb her rest, I decided to take a shower. A much needed shower after double doses of exercise in the morning.
As the tepid water rained down washing away the sweat, I felt refreshed again. I didn’t know how long I was standing under the shower, the thought of sex with Jessie earlier and the touches from the water awakened my manhood once again. I felt a hug from behind and a pair of soft breasts brushing against my back.
Jessie was awakened by the sound of dripping water of shower and decided to join me. Her hands slowly moved towards my already awaken manhood.
Jessie: “Looks like someone haven’t had enough.”
With that, she pulled a fast grab on the head of my manhood and started giving it slow pumps under the shower. I closed my eyes and enjoyed the touches, my two hands moved to grab Jessie‘s well-endowed bosoms.
I turned myself to face Jessie, gave her a peck on her forehead, and then turned her to face the mirror while she was resting on the wash basin. Spread her legs slightly, I rubbed my manhood just outside her love hole. Jessie gyrated herself to feel my harden manhood. Her breathing heightened.
Jessie: “Sean… Sean… I want… You… Inside of… Me… Right now… Sean… Right now…”
Sean: “How much is your desire jie?”
I continued to tease her, not wanting to give in to her request. Both of us were looking at the mirror in front.
Jessie: “Erg… Sean… Stop teasing… Me… Sean… I want you in…side… Me… Please…”
Sean: “Jie… Will you be my slut? Will you let me fuck you as and when I need you?”
Jessie: “Yes… Sean… I am your slut… I am your bitch… I will let you fuck me when you need me… Please… Sean… Fuck me right now…”
With her words, I slid my manhood in her already flooded love hole. Damned. That warm and wet feel gripping my manhood and I pumped her in slowly doggy. Jessie was moaning without restrain, totally lost in her sexual desire to get fucked.
Jessie: “Sean… Faster… Fuck me harder… I am coming soon… Erg… Sean…”
Looking at Jessie in trance through the mirror and her dirty talk aroused me further, I sensed my load was building up. I strengthened each pump and gathered the speed. It didn’t take long for Jessie to climax, her eyes rolled back and gave a loud moan of pleasure. I continued to pump her in front of the mirror till I emptied every single drop into her warm love hole. I leaned on top of Jessie and hugged her as we both gathered our breaths.
Sean: “Jie, let’s clean up and have our lunch. Do you have anything in the afternoon?”
Jessie: “No Sean, why?”
Sean: “I am going house viewing, want to accompany me?”
Jessie: “Sure. Let’s go!”
We cleaned up and had our lunch before heading over to view the house. It was one of the matured condominium near Lakeside. The apartment was really well maintained as the owner (Some rich Indonesian businessman.), bought it as their vacation home. He was letting go of this one as he bought another at Sentosa Cove I heard. The price was pretty reasonable and I didn’t have to spend much on the renovation. Jessie seemed really happy with the place too.
I instructed my agent to help me settle the deal, as Jessie stood by the balcony overlooking the lake. I walked over after settling the administrative matter and hugged her from behind.
Jessie: “This place is really nice.”
Sean: “Yes, indeed. I am glad you like it too.”
Jessie: “Me? What is it to do with me?”
Sean: “You are my slut remember? This will be our den in the future.”
Fridays and Saturdays were quickly becoming a regular meet up after work between me and Jessie to satisfy our sexual needs.
Jessie‘s husband was always busy with his business, flying around. While her kid preferred hanging out with their friends than with Jessie. Which was also why Jessie was always free to meet me on these two days weekly. Sunday was her usual family day.
The purchase of my house went on smoothly and I moved into the new house after three months. Sometimes Jessie would stay over if her husband was overseas.