What Could Have Been Ch. 04

Disclaimer: This is a taboo story between a family friend, brother, and sister of consenting age, i.e. we are 18+. Like I mentioned in my first chapter, if you're not interested in reading stories of that nature, then I really have to question what the f*** you're doing here in the first place. If you don't like brother sister sex, then seriously turn away now. Not turned away? Then cool, enjoy the story. *Just a note: while the interaction between me and my sister here is a fantasy; the encounter with the family friend really did happen*.

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After our fuck session, Sha and I were acting like how ordinary brothers and sisters would act when our parents returned home from work. With my parents' home, I handed them the gifts I brought over from the U.S, following which we went out for some shopping and dinner.

At dinner, I sat next to my sister who was wearing a loose pale blue blouse and shorts while my parents were sitting across from us in the crowded restaurant. They were asking me about my studies while all I wanted to do was place my left hand on Sha's left thigh.

However, I had enough sense to not do anything that night while we were having dinner and talking to ur parents.

It would be later that night, thanks to my exhaustion, that I crashed five minutes after returning home. I was out like a light when I had the most wonderful dream. You see, dear reader, my room is right across from Sha's room. We share a bathroom with each other, and this night I heard her open the door on her side of the bathroom.

I was sitting up on my bed while the lights were switched off watching videos on my laptop. I was still suffering from jetlag, so sleep didn't come easy at all for me. Then I heard the tell-tale 'click' of my sister locking her door before hearing soft footsteps coming towards the door on my side of the bathroom. I was leaning against my headboard when I looked up from the laptop screen and looked up at my sister slowly open the door on my side.

The light from the bathroom shone onto my room's wooden floor, but it was enough for my sister and me to see each other as she leaned into my room. She was wearing a long shirt and with shorts underneath. And thanks to the warm yellow light from the bathroom, I was able to see that she was wearing no bra. Sha smiled at me and licked her lips before stepping into my room while keeping the door behind her in case our mom entered her room to check in on her and knocked on her door.

Sha then walked backwards, looking at me while licking her lips, to the door that led to my room from the living room hallway outside. And locked it.

"So, Sha," I said before Sha placed a finger to her lips as she walked back into the light. My mind raced with the events of earlier that day, as she started to sway her hips from side to side gently while running her hands through her dark hair. A smile formed on my face as she stared at me while licking her lips. At the same time, she slowly ran her hands over her body.

I closed the top of the laptop and placed it on one side while Sha was dancing to music that only she could hear in her head. She walked to my left side while swaying her hips from side to side slowly and deliberately. I looked up and saw the smile on her face, her eyes showing off her lust, and her tits bouncing with each step she took. I remember breathing in and out deeply before I moved the blanket off me, and then turned around on the bed while she turned around and bent over while her hands travelled over her ass. She looked back at me before she stood back up straight, and then turned around.

By this time, I was already sitting at the edge of my bed in a T-Shirt and pyjamas while I reached out for my sister. She stared at me silently while holding my hand, and then she reached for and held my other hand while she swayed her hips and started to breathe in and out deeply. I saw her chest expand and then fall while her nipples, under the cold air of the air-conditioner, started to get hard and poke out from under her shirt.

She then placed my hands on her hips while she leaned forward, and then whispered sensually into my left ear.

"I've been thinking about this since dinner, bhai." She then bit my earlobe while my hands tightened on her hips. "mom and dad are asleep."

"I know," I whispered as my hands went under the shirt to touch her bare skin. Her body shivered when my fingers brushed against her skin. She then pulled back and took off her shirt before she looked down and smiled at my cock causing my pyjama bottoms to 'tent'.

"What happened to getting condoms?" I whispered as Sha took off her shorts while I took off my pyjama bottoms. But Sha remained silent. She leaned down and kissed me on my lips while my hands cupped her heaving tits, and gently squeezed. I heard her moan while her tongue went into my mouth, and mine went into hers. My hands roamed her naked body, my lover yelping as I squeezed her ass. I was about to pull her down onto my bed when I heard a loud beeping sound, and someone shouting my name.

The next thing I know, I'm opening my eyes to find Sha looking back at me. She chuckled before saying that I was sleeping on my stomach, so she had to nudge my shoulder until I was awake. I looked at my sister with sleep still in my eyes while trying to figure out if this was a dream, or if the one where my sister was straddling me naked was a dream.

She nudged me again when I closed my eyes before saying that she was going to leave for school in fifteen minutes, "and I want to say goodbye."

"You're going to school?" I asked while I shifted my body until I was laying on my side. I saw that Sha looked down my body, and a smile appeared on her lips before she looked back at me.

"Yea," she said, "and look who's hard."

"Had a dream about you," I said while rubbing my eyes with the back of my hand as I sat up in bed. My feet were dangling off the edge of the bed as I then looked up and down at my sister wearing her school uniform; a white blouse underneath a blue knee length pinafore, with white socks and shoes. Her hair was tied into a ponytail, her eyes constantly looking at my cock and then back into my eyes.

"What was the dream?" she asked me.

"It was just a dream," I told her before looking down at my erect cock, and then back up at her, "now this is real life. How about you take care of me?"

"I've got ten minutes until I leave," Sha told me before saying that mom and dad would know something was amiss if she wasn't back out there since she needed to leave the house. I told her that I had an idea. I wanted her to leave my room, and then walk out to the living room and tell our parents that she had to go to the bathroom since she wasn't feeling too well. I then explained that I'll leave my room with her, say goodbye to our dad who was going to walk her to the bus stop before going on a walk for thirty minutes.

"And then I'd tell mom and dad that I'm going back to sleep," I said. "I'll quietly lock my door while you walk into the bathroom and lock the door behind you."

Sha smirked before we left the room. The plan worked perfectly, with my dad telling my sister to hurry up. And we did hurry up. I locked my door and then pulled down the pyjama bottoms. My cock was standing up straight as my sister, who was going to be doing her 'A' levels at a Catholic school at the end of the year, went down on her knees and took my cock into her mouth. She expertly used her tongue to caress the shaft while bobbing her head forwards and backwards. I was leaning against my closet as she looked up at me before closing her eyes.

I saw her spit lube my shaft before I closed my eyes and enjoyed the pleasure of my sister sucking me off in her uniform. It didn't take long for me while she attacked on multiple fronts; a hand to stroke my shaft, her tongue to play with my cock head while her lips sealed the head and sucked it gently, and her other hand played with my balls.

It didn't take long for me to grunt as I shot stream after stream of my cum into Sha's mouth while she looked up at me and swallowed. Only four minutes had passed from her sucking my cock, to me cumming in her mouth. Sha then stood up with a smile as she swallowed the last bit of cum, and looked into my eyes.

"Remember to get the condoms," Sha said before she kissed me full on my lips.

"I'll pick you up from school, I'll be going the place nearby," I said after pulling back. Sha nodded her head before she wiped any cum on her mouth and lips with the back of her hand. She then rushed into the bathroom and opened the door to her room before she left. I quietly unlocked the door while my sister said goodbye to my mother, and then left with my dad for the bus stop.

It would be a few hours after my parents left for work that I went to the shopping district. I heard of a shop that carried mostly condoms, and that's where I went after looking up the address. By the time I was done, the time was twelve thirty in the afternoon and Sha's school would be finishing at 3 pm. Having some time to kill, I decided to take in a movie by myself while holding the black coloured bag which contained several packs of condoms, two bottles of lube, and two bottles of scented massage oils.

Walking out of the store, I was surprised to be greeted by an Aunt who had just talked of the store next door. Now, before I continue, in my culture an Aunt can refer to blood relatives or family friends. And this was a family friend. We knew each other ever since moving to Singapore, and I was friends with her son and daughter.

And it was the same with my sister; my Aunt's daughter was her best friend.

"Abe!" I remember her saying as I tried to hide the bag in my hand behind my back. She told me, seemingly oblivious to the fact that I walked out of a Condom shop, that she heard I was back for my Summer vacation. I couldn't help but nod my head while hoping that she would simply leave, and forget about where she met me when she no doubt talks to my parents. However, her obliviousness didn't last long. She looked at the shop behind me, and then at me before saying, "bought something for your girlfriend?"

"Yea," I replied while nodding my head as I placed my arms by my side since there was no use hiding the bag of condoms, lube, and massage oil.

"What did you get?"

I was surprised by the question, and all I could do was stare at her while several people walked past us. She then chuckled before inviting me to lunch at a nearby hawker center. I told her that I should be heading off since I was picking up my sister from school.

"When is Sha done?"

"At three," I admitted before she insisted on buying me lunch. She said that it had been a long time since we talked and I accepted. I just didn't want to spend more time with her than I had to, which was why I didn't tell her that I was actually wanting to watch a movie. My hope was that we'd go our separate ways after lunch, and I could still catch a movie before meeting my sister.

And I should tell you, my readers, that I don't want to spend more time with my Aunt than I have to because of how she looks. My Aunt was about forty-nine at that point in time but she didn't really show it. She had a head full of waist length black hair, brown eyes, hardly any wrinkles on her face despite being an academic in a different Singaporean university- a stressful job in itself. She was about 165cm tall with a slim body, what looked like D-cup tits under her loose blouse, and had a fondness for wearing long skirts. So she was attractive.

I just didn't want to spend time with someone who I knew saw me getting out of the condom store. Once we reached the Hawker center, we got a place to sit before she handed me some cash and asked me to get something for the both of us. I was about to walk away with the bag in my hand, but she insisted on holding it while I went to order. I opened my mouth to say something, but she pre-empted me by saying that she was coming with her son and daughter to visit my parent's apartment later that night.

"And Uncle?" I asked when she didn't mention him.

"We're divorced," she said before saying that she had a class in two hours. She told me to leave the bag with her while I went to get the food. Surprised at the revelation that she was divorced, I placed the bag on the table while my Aunt, probably sensing that I was surprised, said that she would explain when I got back.

When I got back a few minutes later with two plates of food, I saw her smirking at me while she was holding onto the bag.

"So, I take it you looked?" I asked while handing her the food. I looked into her eyes which looked back at me before I heard a hushed yes. I watched her look at my face, and then at my crotch before looking into my eyes. Without a word, she then started to eat her food while explaining how her marriage had broken apart.

All I could say after she finished talking was that I didn't know, especially since I hadn't talked to her son and daughter lately. I added that my parents never told me either, and neither did my sister.

And then the conversation went into a sudden tangent.

She said that she was out for an errand before she was due to get back to her office. She was going to stay there until class, but she met me instead and she wanted to change her plans. My Aunt then leaned into my ear while I sat next to her and asked, "how big are you?"

"Auntie?" I asked surprised as she looked back at me with a gleam in her eyes.

"How big are you?" she repeated before placing a hand on my thigh, and gently squeezing it, "Abe? How big are you?"

"Seven inches," I replied. She bit her lower lip before standing up. She pulled me up as well and took the bag in her hand before pulling my arm with her other hand, leaving the half-eaten plates of food on the table.

It was a few minutes later that we entered a nearby hotel. My Aunt paid for the room before we went up the elevator to the fortieth floor. Going up the lift, I heard my Aunt panting as she looked at the numbers on the panel changing... increasing one by one as our floor approached. I bit my lower lip and shuffled over to her side and placed my hand on her lower back before asking why she was doing this.

"Because I was going to my office early, and then I was going to call my Research Assistant," she admitted, "I was going to... to..."

"Fuck?" I asked as I lowered my hand to her ass, and gently squeezed. My Aunt closed her eyes before admitting that ever since the divorce, she's been feeling free. She said that she and her ex-husband hadn't been having sex for years and that she was horny. But she couldn't have an affair since she was stuck in a sexless marriage, but now she wasn't married any longer.

And for the last six months, she had been gathering the courage to call her Teaching Assistant.

"But now I met you," she said looking at me as her chest heaved up and down while I rubbed and squeezed her ass. "and I don't need to call my Assistant. I have you until my class."

The doors to the fortieth floor then opened with a beep, and my previous thoughts about not wanting to spend too much time with my Aunt melted away. I saw that beads of sweat were already gathered on her forehead as I pulled her out of the lift. We rushed to the room door, opened it, and just before it could completely close, my Aunt pulled me close and kissed me.

I gently pushed her so that I could take off my clothes, eventually standing naked with my erect cock pointing towards her as she took off her clothes as well.

"Oh God!!" she exclaimed as I pushed her against the wall and kissed her. I kissed, sucked, and bit on her skin causing her to moan in pleasure while her hand travelled down to my cock. I moaned in turn as she started to stroke the shaft while I kissed her shoulder, my tongue leaving a trail of saliva.

I then kissed her neck again before going back to her ear, and growled, "what do you want me to do? Tell me, Auntie."

"Fuck me, Abe. Fuck me, baby." she moaned as she stroked my cock faster. I was panting into her ear as sweat gathered on my forehead. I then remembered that we hadn't turned the air-conditioning on. And I didn't care.

And neither did my Aunt.

"Take me, Abe. Take me hard."

"You're a slut," I breathed before leaning down and putting her nipple into my mouth. I stroked her nipple with my tongue until it hardened before I bit down. She then arched her back while yelling out loud, "AIIIIII! AIIIII!". At the same time, she quickened her strokes before she let go of my cock and placed both her hands on the back of my head. She was pulling my head onto her tits while I was roughly sucking, licking, and biting her nipple and areola.

"I'm a slut, I'm a slut," she wheezed. My ears couldn't believe what I was hearing as I pulled away from her grip and stared at the panting and sweating woman in front of me. She was covered in sweat, from her face to her large D- cup tits, to her abdomen, and to her hair covered pussy. I looked back at her eyes which looking back at me before I grabbed her arm, and then I grabbed the bag on the carpet.

I pulled her to the bed and then told her to lie down while I took out a box of condoms as I was panting. I opened it while she lay down staring at my cock. Licking my lips as I looked at her and then my eyes travelled down her body, I put on the condom.

I didn't wait for an invitation as I roughly spread her legs and then went straight for her pussy. My Aunt's back arched immediately before she released a scream of pleasure. She repeatedly called my name while I licked her soaking wet slit. I looked up her body while wrapping my arms around her legs as she started to buckle and writhe while I latched onto her clit and sucked.

"Oh FUCK MEEEE!!" she yelled out loud as I licked her clit at a fast rate of speed until my tongue hurt. But I didn't stop as she released one scream after another as her body quivered. Her legs then pressed in against the sides of my head while she held my head down against her pussy so that I wouldn't stop what I was doing while she buckled. "Oh God, Oh God! Fuck me... fuck me."

I moved my wet face off my Aunt's pussy, and then I crawled up her body between her legs as she panted while saying that she hadn't orgasmed like that in years. She then opened her mouth as I kissed her, and she tasted her own pussy juices mixed in with my sweat.

"Tell me how you want it," I hissed as I looked down at her while she wrapped her legs around my waist while reaching down to grab my shaft, and then aimed it at her opening. "Tell me, slut."

"Hard," she said, "hard. I just want to be fucked and... OH GOD!!"

I slammed my cock into her before she could finish what she wanted to say. I continued pounding into her while she screeched into my ears and gripped my back with her hands. We could hear the 'plop' sound of my cock being rammed into her wet pussy while she was screaming in pleasure. All while telling me not to stop.

"Cumming... I'm cumming... cumming.. cumming!!" she yelled just as I felt her pussy walls closing around my cock. It was at that time that I said I was going to cum as well, "cum in me!! Please baby, cum in me!!"

"Fuck!! Fuck!! FUCK!!" I grunted as she screamed thanks to another orgasm, while I came into the condom. I continued pumping in and out until I collapsed onto her body... our skins were on fire as they touched. And it led to me firing a few more strands of cum into the condom while my Aunt came once again.

"Oh God," she wheezed as I kissed her neck. "That was so good, Abe."

"We have more time to kill," I said as I looked back at her while she bit her lower lip. I pulled my cock out of her pussy, and then took off the condom full of cum before taking out another one. I looked at my Aunt who was panting and smiling at me before managing to say that she was willing to go for another round. She spread her legs wide and stared at me with eyes filled with lust as she bit down on her tongue.