I Had Sex with a Friendzone Friend

Happened a few years back in 2013. Daniel (Me.), David, Andy and Jean were a bunch of very good friends. Andy, Jean and I were from the same secondary school. Jean and I were classmates for our entire secondary school life and Andy was from the next class. The three of us got together through classmates from different classes, but had since left only the three of us when the incident happened. David only came into the group during our poly times when each of us went into different poly.

Fast forward to May 2013 when we were all in our early 20s. The guys, David and I had already ORD’ed while Andy was still serving the final few months of NS. While David started his own small company, I was waiting for university school terms to start in July. The only girl Jean was already working as an ad hoc admin in a fitness company.

One Friday, we received a whatsapp message from Andy, who had just returned from an overseas training and was suggesting to meet up.

Andy: “Yo guys! I am back!”

David and I: “Wha like finally! Means your ORD date is even nearer! Haha.”

Andy: “Haha, yeah. By the way I bought a few liquors from the duty free store when I touched down. Wanna meet up at my house to have a drink?”

Jean was usually quiet in the group chat due to her workload. She usually had to work OT almost every day, sometimes even until after midnight. I of course welcomed the idea of meeting for drinks since we hadn’t met for a couple of months due to individual activities, but an idea struck my mind before I replied to the chat…

This was a good opportunity to get into Jean‘s pants.

Jean was considered my childhood crush. She was a girl filled with both sweet looks and personality, however, was a shy girl in everybody’s eyes. She was considered one of the very few pretty looking girls in the class, therefore no doubt she briefly dated a few of the male classmates, one of them being my buddy. Contrastingly, she had no luck in all of her relationships so far, either the relationship didn’t last long (One to two months.), or ended on a really sour note. Of course, I carried a torch for her, but my appearance definitely lost out to the guys that she dated – I was lean build, wearing outdated rounded-frame specs, at that time I didn’t know how to improve my appearance, just go around cracking jokes hoping to impress her with my humor.

Back to that whatapp chat, I could only hope Jean replied and agreed to the drinking session at Andy’s house before coming up with any sort of plan to get her to get laid. Knowing that she wouldn’t reply instantly due to her heavy workload, I went back to playing my PS3 for a couple of hours before checking on my phone in hope of seeing a reply from Jean.

About 4.30 pm that afternoon:

Jean: “Hmm, I am okay to meet. Wah very long never meet you all already leh!”

Me (Heart was obviously skipping fast, but kept calm.): “You finally replied! Haha.”

David: “Haha, she is always busy one leh. Her reply at this timing is considered very lucky already!”

Jean: “Eh, you all don’t like that leh! I am really busy! By the way I think I am able to leave slightly early tonight.”

Me: “Early is how early? Before 12 midnight? LOL.”

Jean: “Haha, not that jialat la! Think 8 plus to 9 plus bah. Just nice when I reach Andy’s house the timing good for drinking right? LOL.”

Me: “First time see you so steady! Very good. In order to reward you, I will sponsor the mixer!”

David: “Wa sure bo! Aiya mixer cheap one leh! But better than nothing!”

Me: “Or you want to drink neat and KO instantly huh? Anyway, Andy, how many bottles you have so that I can buy the right amount of mixer later?”

Andy: “I got one Absolut Vodka normal, one peach flavor and one Smirnoff green apple.”

Me: “So many?” (Obviously, even more thrilled.) “How you buy so many one?”

Andy: “Get my mates to help me buy la. They all not drinkers, so can ask them to help me get extras mah.”

Me: “Wah steady! Ok, leave the mixers to me!”

David: “Haha, see you guys tonight!”

Jean: “See you peeps tonight!”

This must be my lucky day. With Andy’s supplement of Vodka definitely good enough to get all of us dead drunk, I intended to come up with a plan especially for Jean. I began to search on google…

I began to search on google for various ways to make a person getting drunk faster. After a browsing through a few results, I came across this article that said mixing alcohol with diet soda would make one getting tipsy at a faster rate as there was no sugar content. I decided to give it a try since it had no drugs involved.

At about 8.30 pm that day, I made my way to Andy’s house while stopping by at a convenience store to purchase eight 1.5 liter bottles of Coke Light. With each hand carrying a plastic bag of four huge bottles, I dragged my way to Andy’s house.

At 8.50 pm, I finally appeared at Andy’s doorstep. David was already there watching television in the living room.

Me: “Eh somebody please open the door. Very heavy leh!”

David: “Haha, who ask you to volunteer to treat the mixer!”

Me: “Wa you like that one ah! Treat you all still so much words to say!”

Andy (Just came out of his room.): “Here comes the boss!”

Andy’s house was a typical old-styled two-room HDB flat at the north. He shared a room with his sister with his window facing the corridor. After Andy opened the door and both the guys helped me out with the bottles, I saw the alcohol bottles already being displayed on the dining table along with a few bags of snacks. There was no sight of Jean yet.

Me: “Damn heavy sia. Need to rest awhile.”

Andy: “Hello, you served army one leh, how can complain heavy?”

Me: “You try carrying six liters of water on each hand la! By the way Jean haven’t reach yet ah?”

David: “She said on whatsapp that she leaving the office about ten minutes ago. Should reach here around 9.30 pm bah.”

Me: “Oh, just now I no hands see the phone for messages. Sigh, she always the last to reach one. Then Andy, where your parents and sister? We party at your house they all okay with it?”

Andy: “My sister went overseas, so we can have the room to ourselves. Just not too loud la. Usually my mother comes back don’t care one luh.”

With only the four of us in a room, I was thinking to myself: This is the perfect setup plan. As both Andy and David were watching television and chatting about NS, I was quietly waiting impatiently for the arrival of the female lead here, Jean. My mind was already virtually imagining the situation I wanted to have later.

Shortly after 9.30 pm, we heard a door knock. It was Jean.

She appeared in her work attire – wearing her fitness company’s black t-shirt with denims. The t-shirt looked tight on her, but not overly tight, therefore exposing her nicely shaped rounded B-cup boobs. Her denims, however, was tight, revealing her shape of her thunder thighs. Seeing the shape of her boobs just reminded me of the particular day when I decided I want to see her naked one day:

This was the day when we were celebrating a mutual friend’s birthday when another friend happened to use my camera and the flash flashed directly on us, seeing through her cotton clothing and exposing the bra underneath. Nobody was aware of it except for me, as I was the camera owner. When I first saw the picture, I let my mind run loose. She wasn’t slim and fit, not on the meaty and fat side either, but I would consider her having the right amount of fats at the right place.

Jean: “Sorry ah! Late for a bit. Hehe.”

Her words snapped my imagination just as I was staring at her boobs.

Me: “Ohh. You look kinda shagged leh. You sure you are game for later or not? Hahaha.”

Jean: “Wah don’t look down on me please! But then said, I quite long never drink already leh!”

Andy: “Haha, then you take it slowly la. Here is not club!”

David: “Come, come! Let’s get the game started!”

We took the alcohol, some bottles of coke light and the snacks and proceeded to Andy’s room for the session. I purposely walked closely behind Jean and brushed my hands against her back. It felt good.

She didn’t react, probably because she thought it was accidental.

We sat on the floor in Andy’s room as there was space to sit in a circle. Andy went to take the remaining drinks in, closed the door and switched on the air con. Both of Andy’s and his sister’s bed were placed on two sides of the walls. I obviously waited Jean to sit down before going on to sit next to her. Andy brought the cups in and asked:

Andy: “Eh, so which one we are going to open first?”

David: “Erm, anything la, since all are alcohol hahaha.”

Jean: “I have no opinion, so anything also.”

Andy: “Every time you all like that one sia! Everything also anything! LOL.”

Me: “Eh chill leh bro. Why not we open the normal Vodka first?”

Andy: “Haha ok, steady!”

There’s a reason why I chose to open the plain flavor first. I chose to leave the two other flavors for later because I assumed people would just drink more Vodka with flavorings than the plain ones.

After doing our ‘opening’ toasting, we officially began the game. The first game we played was Monopoly Deal. We agreed on the rules that whoever left with the least amount of money every game ended will drink half of their cup. At first, everyone took turns to lose the round, and then towards the later part, somehow David got really unlucky that he lost four games in a row.

About an hour and a half later, we barely left with a quarter of the plain Vodka and David was already on the verge of knocking out. He was a poor drinker at that time.

David: “Eh, I cannot already sia! My head very pain already…”

Andy: “Haha, don’t be weak leh! Be a man!”

Me: “Ya lor! Don’t know just now who say me complain heavy now you also complain!”

Jean: “Haha David you damn weak leh!”

Me: “Ok, why not we change the game?”

My initial plan was getting each of them knocked out as soon as possible and of course I had to stay lucky for the games as well. So four of us agreed to change the game and Andy went to bring a box of Jenga blocks. My mind was already thinking the idea of Strip Jenga, but the time was not right and too early of course, when most of us was still sober.

Andy: “Come! Let’s play Jenga! Whoever makes the block fall drink!”

David: “I don’t want to continue can…”

Jean: “Play lah! We still have two more bottles you so fast gone! Who is going to help us finish?”

David: “Ok ok I try I try…”

And we continued our round two of the games. David was trying very hard to stay awake and upright that he made all of us laughed. Each time he attempted to remove a Jenga block, we attempted to distract him and he lost a few more rounds. Of course, we gave chance to him in between and the remaining three of us had quite a few sips. We finally opened the second bottle, the peach flavor Vodka.

We came to a point that David just went flat on the floor and no matter how we called him or shook him, he wouldn’t respond, or at times gave out a shout, which made us laughed even harder especially when the alcohol effect was starting to kick in. Seeing David at such a state, I suggested to carry him onto one of the beds.

Me: “Eh, he really KO liao leh. Let’s move him up the bed lah.”

Andy (Still laughing pretty hard.): “Hahahaha… Haha… Ok, ok… Give me a while… I need to stop laughing to have the strength to carry him…”

While moving David to the bed, I sneaked a peek at Jean. She, like Andy, was still laughing at David or the way both of us were carrying him. My mind was wondering: Is she finally drunk? Or is she still sober? It was still dangerous to try to take advantage now.

After finally settling David, who was lying like a corpse on the bed, the three of us got back to sit on the floor, wondering what we should do next.

Me: “Haha, that was really funny… My stomach damn pain.”

Andy: “Stop saying la hahhaha… The moment you said it make me laugh also… Hahahha.”

Jean: “Hahahahahah yeah lor!”

Me: “Eh, we still got one more bottle left leh. How ah, you all can continue bo?”

Andy: “Come lah! Let’s see who is the next one KO!”

Jean: “Hahaha, I think I half half KO already. Andy you got other games to play or not? If not the Jenga blocks fall quite loud.”

Andy: “Let me go see…”

Andy needed to hold on to the wall in order to get up and search his cabinet. Meanwhile, I tried to act like I was about to get knocked out also. I shifted my body near to Jean and pretended to tap lightly on her thigh.

Me: “Eh, you ok or not?”

She didn’t seem to react to the tap, but managed to reply me as usual.

Jean: “Haha ok la. But I a bit hungry.”

She went on to open a bag of Ruffles chips and started eating. By then, Andy just managed to come back with a deck of poker cards.

Andy: “Ok, final game! Blackjack! Play until we finish all the Vodka!”

Me: “Game!”

Jean: “Hahaha ok! But I think I will be the next to KO! Hahahaha.”

The final game was pretty much even to everyone when each of us had to drink sips after sips. Occasionally we looked at David and just laughed at his sleeping manner and posture. Finally, the point when the three of us barely finished the last sip of the apple Vodka. Each of us was lying on our back either on the floor or against the wall. Me, barely sober enough, pretending to ask out, who was still sober.

Me: “Eh! Who still alive ah…!?”

Andy can only laugh with his eyes closed.

Jean: “Hahahahahahaahaha… I very tired. I want to sleep.”

Me: “Let’s go sleep then!”

The three of us barely had the strength to stand up. The question was, where do the three of us sleep? The way David was sleeping, it was impossible to share the single bed with him with his four limbs spreading out wide. Seeing that Jean and a barely there Andy still able to stand up, I guessed they were pretty good at tanking the alcohol effect too.

Naturally, the three of us just slammed our butts at Andy’s bed and lie down perpendicularly to the length of the bed, with Jean lying in between me and Andy, with just a bit of a gap between each other. We shared the blanket as the three of us were feeling the chill of the air con, probably part of the alcohol effect too. After a long, long silence, I turned my body towards Jean to check if both Andy and Jean had already knocked out. Andy was facing the outside and not moving therefore I assumed he had knocked out. However, to my surprise, Jean‘s eyes were still open.

Me (Whispering.): “I thought you said you very tired want to sleep?”

Jean (Also whispering.): “Somehow cannot sleep… Haha.”

Me: “How come leh?”

Jean: “Because not my own bed mah. Naturally must sleep own bed, then can sleep easier… Hahaha.”

Then there was a long silence. Suddenly our eyes were locked to each other. Somehow our eyes were looking at each other for a good five seconds, before Jean giggled shyly and looked away.

Both of us knew something was going to happen. I shifted my body towards her, crossed my leg on top of hers. Now her face was right in front of me. We looked at each other again and I made the first move to lightly kiss her on her lips…

She didn’t show any sign of rejection. She could only look at me and gave her trademark shy smile. She tried to avoid direct eye contact with me. I knew that she only treated me as a friend and nothing else, but from the situation, I could tell that her body wanted something that her mind didn’t. Even though she was sober, the alcohol effect was clearly taking control of her mind.

Before I already knew it, both of my hands were already on her body unknowingly. I lowered the blanket and my right palm was stroking her hips while my left was stroking her gentle arm. She still didn’t show any sign of rejection. All the caressing on her was already making my dick hard. I decided to take a bold step further.

I moved my groin towards her and started to rub against her crotch. She could obviously feel my hard on dick. I was already half expecting that she would resist and push me away, but to my surprise, she didn’t. Again, she looked at me and giggled shyly. She was enjoying it so far. Seeing her reaction, I slipped my right hand, which was caressing her hip underneath her shirt, directing stroking her smooth skin. I could feel the adrenaline rush down my stone hard dick. Seeing that she didn’t resist any further, I moved my head towards hers and whispered:

“Take off your shirt, Jean.”

She smiled at me, giggled, and proceeded to remove her shirt. I was totally amazed that she obliged. I then assisted her in removing her top as we tried not to awake Andy, who I presumed to be knocked out.

I stared in disbelief at her body for a good ten seconds. Fair, smooth with the right amount of fats in the right place. She was almost naked, leaving only a white underwire bra covering her round B cup breasts. Again, my hands were already all over her body while my stone hard dick continued to rub against her crotch. While my hands were enjoying all the caressing, I was questioning my mind: Why was Jean allowing me to do this? Was she sober or drunk? Should I continue? What if I continue and spoil our friendship?

With all these questions recycling in my mind, Jean suddenly let out a soft moan that disrupted my thoughts.

Jean: “Uuuhhhh…”

Me (Whispering.): “You are enjoying it right?”

She could only react with her usual smile. We didn’t kiss. No words. I could feel that she wanted more, just that she was too shy to say. We didn’t talk about dirty stuff or sexual topics to each other before.

I proceeded to grab her whole body and pull towards mine. My body started to rub directly against her almost naked body at an increased tempo. My head sank to her shoulders and kissing all over her smooth skin while both of my hands were fondling her nearly bare back. I pressed my body against hers to feel her breast. Man it already felt like I was in heaven. I could already feel the pre-cum at the tip of my dick. How would I react when she will be fully naked in just a while? After a good two to three minutes of excessive heavy petting, my hands automatically went to the bra clip and unclipped it. Jean then put her hands on my chest. Was this an indication to stop?

Without looking at each other:

Jean (Whispering.): “Eh, what are you doing…?”

Me (Still in the midst of kissing her body.): “Mmmm… Mmm… I want to see you naked… Mmmm… I don’t care… Mmm…”

Without waiting for her reply, I used one of my hands and gently moved her arm and slightly pushed away her body from me while the other hand gripped the front of the bra and pulled it off her body and over her hands.

Now, Jean was completely topless in front of me. I had never seen a girl topless, let alone naked with my eyes before. I stopped my caressing and fixed my eyes on her breasts with my mouth wide open. Beyond the bra was a pair of dark pink nipples which were slightly pointing outwards combined with her perfectly soft, round breasts.

Jean was giggling as always while shyly trying to cover her breasts with her arm. I pushed it away so that I can admire something which I had never seen in my life before. “Oh my holy mama.” Was the words I whispered to her while she could only giggled all the time. She did not show any sign of resisting and my mind was set to carry on with the plan of getting her to get laid.

I moved my hands towards her bare breasts in an attempt to feel a boob for the first time in my life. Suddenly a hand appeared underneath Jean‘s arm and grabbed one of her boobs…

Jean and I stared at each other looking petrified. It was Andy’s hand. He was pretending to be asleep all this while. While Jean was continuing to be in a semi state of shock, my mind was wondering, what was Andy doing?

Andy was in a relationship with a girl named Wendy at that time. They knew each other during their poly days, but had been in an unstable relationship all along. Andy, in fact like some of us, could not stand Wendy’s bitchy attitude and her attempted dominance over Andy in their relationship, often forbidding him in doing the things he liked and forced him to accompany her when she had nothing to do instead of hanging out with his bunch of friends, including us. We had seen them quarreled often and advised him to break off with her, but he always rejected the idea being fearful of the consequences of Wendy taking revenge if he did that. To add salt to his wound, Wendy was neither pretty nor having a good figure.

Perhaps being in a stressed-up relationship, Andy sorely needed some fun, which was why he would get turned on when Jean removed her top? But he knew that I had a crush on Jean all these while so why was he doing this?

Before I could act impulsively to stop Andy from spoiling my night, I calmed down and think twice. Instead of stopping Andy and spoiling the sensual atmosphere, why not let Andy join in the fun?

Yes, I was thinking about having a threesome with my best friends.

It wouldn’t hurt to share your favorite girl with your best buddy right? I got that idea when I suddenly remembered watching a college threesome video on a porn site a few days ago and that was when I developed a fetish for a threesome act. However, I needed to convince a semi-drunken Jean as well.

I looked over Jean‘s bare shoulder and gave a smiling signal to Andy. He was obviously thrilled given that how quick his tempo was when his hands were on Jean‘s soft breasts. By then, Jean was tightly sandwiched in between Andy and me, her bare body being fondled in every place. Moments later, she finally snapped out of her petrification, turned her head to and fro both of Andy and me and spoke in a giggling manner:

“Eh guys… I never do with two guys before leh…”

This time, I was the one who was staring in amazement at her. Was I dreaming or did I really just heard what she questioned? I then proceeded to think, since she said she didn’t try it before, she would also mean she was willing to try right?

While Andy was still busy fondling Jean, I sat up and began to undress myself. I couldn’t resist any longer, hurriedly taking off everything as quick as possible. Soon Andy saw what was coming and he too followed the suit to strip himself. Both of us were caressing Jean while stripping at the same time. Finally, I quickly pulled down my underwear and exposed my already rock hard uncircumcised 4.5 inch dick to Jean. Being a guy inexperienced with sex, the pre-cum already dripping out as I couldn’t contain my excitement.

Jean stared at my uncircumcised dick for a moment, giggled.

Jean: “Eh your one is uncut ah…”

Me: “Yeah, no choice leh. You know how to do uncut one?”

Jean: “Haha, never see before of course don’t know… And you already like want to come already haha…”

Without any indication, she wrapped her palm around my dick. I tried to guide her by holding her hands and asking her to play around the head of the dick with her fingers without pulling the foreskin back too far. Man, I felt I was already on cloud nine.

Andy finished stripping soon after and positioned his erected dick asking for a hand job from Jean as well. Now Jean looked really busy as she had to carefully handle my dick while serving Andy at the same time while we guys were just placing our hands all around Jean‘s body at will. She was half dazed but clearly enjoying the situation so far.

Within a minute, I could foresee that I could come any moment. I needed at least a blowjob from Jean. I stood up, kneeled on the bed and quickly positioned my dick right in front on Jean‘s face.

Me: “Suck for me Jean… Please… I am coming soon…”

Jean (Chuckled while looking at my dick.): “Heh so fast…?”

Me: “Just suck please… Faster… I will have round two…”

Jean: “Heh… But how to suck yours…”

Me: “Just suck normally…”

She seemed to take some time to absorb what I had said, just staring at me. Unable to hold any longer, I grabbed her head and forcibly pushed my dick into her mouth and started thrusting vigorously. She reacted by shutting her eyes while trying to slow down the tempo by placing her hand on my crotch. I grabbed her hand to negate her resist while using my lower body energy to thrust with my might.

Me: “Uuhhhh! Uuhhhh! Uuhhhh! Shiok… Uuhhhh! Uuhhhh!”

Jean: “Ggrrrhhhhh… Ggrrrhhhhh… Ggrrrhhhhh…”

Andy was obviously enjoying the situation, probably witnessing friends fucking each other for the first time as well. His hands were all over Jean‘s breasts all the time.

After the supposed ‘forced’ blowjob for thirty seconds, the moment I had to unload came.

Me: “Uuhuuhhh… Jean… I am coming… Shoot where… Faster… Where…”

I finally pulled out my dick from her mouth while she caught her breath before replying.

Jean (Panting softly.): “Below my neck…”

I pushed her body towards my dick and positioned it at her neck with one hand holding my dick and unloaded my cum. She was looking at where I will shoot while preparing for the load.

Me: “Uuuuuuuuuuuhhhhhhhhhhhhh aaahhhhh…”

Damn, I never felt so good before. I leaned on the bare back of Jean while she gave me the disgusting-yet-naughty-yet-shy look.

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