My Sex Diary!


Chapter 1 – Hand fetishism

The last day of school before the year-end holiday, I was Secondary 2, once again punished by our Maths teacher Miss Chee to stay back after school. I was only released after everybody had left and as usual, I went up to the top floor toilet for a smoke before leaving school. Before I can finish peeing at the urinal, Meiling slammed the toilet door open yelling, “Andy are you there?”

Meiling was a Secondary 4 ah lian, pony tail with this wow developed C cup with a figure of a vase. She was Andy’s girlfriend. (Andy also in Secondary 4, back then was one of my close basketball teammates, a gangster and a famous bully in school.)

I was stunned by her action as she approached.

Meiling: “Ah boy, you see Andy here?”

Before I can react, she’s already standing beside me waiting for an answer.

Me: “We will meet after school at Macdonald’s, think they are there waiting already.”

Meiling: “Then hurry up small dick!”

I was furious hearing her comments and replied.

Me: “What small, mine is bigger than Andy’s one ok!”

She gave a stare at my 2 IC and grabbed the small fellow and started stroking it, I was embarrassed at first but soon enjoying her participation.

My 2 IC did not disappoint me which grew into a monster soon after a few strokes.

Meiling: “Never thought that guy at your age can grow so big!”

Me: “Not all, it is mine that makes the difference!”

As she was so focused on my 2 IC, I found out that her left breast were rubbing against my right arm while she was doing her stroking, which gave me a good view of her cleavage from the opening of her uniform, wearing a half cup baby blue colored bra supporting her fair white huge boobs. We stayed in that position for about 2 minutes and I ejaculated this thick yellowish cum all over the urinal wall and floor.

Meiling: “Wow, you are not only big, you shoot a lot too!”

She gave me a smile and said: “Now clean up, we need to go!”

I hurried to wipe up the mess and picked up my bag, as I was heading to the door.

Meiling: “Fashion show ah?”

As she zipped up my shorts and gave my 2 IC a gentle pat. I then discovered that in the hurry, I forgot to zip up my school shorts. When we reached Macdonald’s, we saw Andy and three others of our friends sitting in a cozy corner.

Andy: “Ah boy, stay back again ah, now get something to eat and meet us at the billiard center.”

Volunteering to get meals for Meiling and myself, I dashed out of my seat heading towards the counter. When I was back, Meiling was all alone in the corner with her legs crossed wearing this freaking short school skirt, her snow white legs were so sexy and smooth as seemed like ants will slip and fall on them. While I was standing beside her I noticed that I got a good view of her cleavage again. As a greenhorn, I was caught looking as she pinched my arm saying.

Meiling: “Enough already dicopek?”

I kept quiet heading to the seat opposite for her, but were pulled back by her.

Meiling: “Sit beside me, I won’t eat you!”

As instructed, I sat beside her and we started having our meal. She was seated so close to me that her boobs kept knocking my arm when she was taking our consolidated fries on the tray near my side and I felt my heart rate increased and my 2 IC hardened. Out of a sudden, she leaned towards me grabbing my 2 IC with her left hand while reaching for my drink using her right hand.

Meiling: “Hahaha, you are so cute, so fast hard liao?”

She took a few sips from my drink with a very satisfied smile while using her left hand still rubbing my 2 IC, below the table.

Me: “Sis, I can’t liao, I will come in my shorts!”

She laid her head on my shoulder smiling.

Meiling: “Then let it come loh!”

Sure enough, I jacked off my second shot of the day and wet my shorts!

Me: “See lah, all wet, how to go play billiard later!”

Meiling: “That’s your punishment for looking without my permission!”

After our meal, leaving a message to Andy that I was not joining them, I headed home alone.

Chapter 2 – My luckiest moment

Being the only child, with parents working till late nights, I always had the entire house and lots of home alone freedom for myself. I stepped into the house, got naked myself and dumped the wet shorts with my cum (Refer to Chapter 1) into the washing machine and went to bed for a nap.

I woke up around 6 pm, still naked, lying on the bed recalling what Meiling did to me and started to masturbate, suddenly I remembered that my cousin Jess came over to stay at our place for a week for this coming holiday and before I can jump out of bed to get my room door closed, she was already standing there staring at my private act. She paused for a few second eyeing on my full grown 2 IC.

Jess: “Errrrrr… Come down for dinner when you are ready.” As she quickly walked off.

I jumped out of my bed immediately pulling on a boxer and went down to the kitchen. As I approach the dining table, I noticed that Jess eyes were looking at my 2 IC, then I came to discover that it was still quite erected. I tried to cool myself down, but damn, to my surprise Jess was not wearing any bra with her hard pointed nipples so obvious underneath her white loose tee shirt.

Jess, a year older than me, was those obedient, well behaved, helpful and good-natured kind of gal, shoulder length hair, small build with about an A or B cup breasts and a face which I considered average looking.

Jess: “Ah boy, your parents left a message that they are not coming back till tomorrow night and I am here to stay till next Sunday.”

Me: “Ya hor, your mom went overseas for some business trip and you are here to stay for a week.”

Jess: “You forget liao right, that’s why you…” (While she took another glance at my erected 2 IC.)

I took a seat hiding my 2 IC under the table and started off our dinner with her. Jess was a very good cook despite her age and our family got to taste them every weekend without fail and that made both our family very close but the first time where Jess came over to stay. We started some conversation while having our dinner, but I was only concentrating on her nipples which I was introduced this very first time. When we were done with our meal Jess stood up, started clearing the empty plates.

Jess: “Leave the washing to me.”

Me: “Do you need my help?”

Jess: “No, thanks.”

As she carried the plates to the basin, I was attracted to her oversized loose tee that covered just slightly below her crotch area which seemed like she’s not wearing any shorts underneath them. I came to realise that she had this flawless slim long legs that I personally fancied a lot.

Jess: “Are you still hungry?”

Me: “I am full already and the dishes you prepared are very nice.” (Thinking that I was hungry to see what’s underneath the tee-shirt.)

Jess: “Good, go make yourself comfortable then.”

Me: “Ok, shout for me if you need any help.”

I stood up, just when I was about to leave the kitchen, this Jess really knew how to please me while she bent over clearing the rubbish bin on the floor with her glossy white panty facing me covering her cute firm small ass. I captured this image in my mind as I rushed back to my room to wank off. When I was half way through, Jess suddenly knocked while opening my room door with a plate of fruits and I was caught doing in front of her once again.

Jess: “Sorry, here’s your fruits.”

This time she really had a close up view of my full grown monster, as she blushed and ran off. Due to this incident, I confined myself in my room during her stay till the second day. As usual with only Jess and me alone in the house, I was in my room playing video games. Having this urge to pee, I used the toilet in my room that was linked to the visitor’s room next door. After I was done, I discovered that the other toilet door was not totally close. Out of curiosity, I went over to have a peep and certainly found my luckiest moment.

Jess was laying on the bed with her legs spread wide, sliding a pillow up and down on her clit as she slowly wet her glossy white panty. She went further stripping her tee shirt off, finger painting her own nipples exposing her little tits to me. Immediately I started to wank behind the door enjoying this free show. She took off her panty soon after, tapping and vibrating her pussy with her palm, given an opportunity viewing her thin layer of bushes neatly spread along her groin area. It wasn’t too long when I saw that she jerked a few times, with her juice splashing onto the pillow and bed with a soft moan reaching her orgasm. She lay there motionless for a while with her legs still wide open. I ejaculated soon after watching, shooting all over my toilet floor extremely satisfied with her live show. As I was about to grab some tissues to wipe up the mess, she came in (Already with her tee shirt on.), and caught me naked again.

Jess: “What are you doing?”

She paused a while… (Noticed her door was not close.)

Jess: “You… You saw it!”

Before I can give her an answer, she stepped on my semen and lost balance, at that point of time, I reached out to grab her. Instead of holding her balance, both of us fell on the floor with me landed on top of her.

She moaned with pain with our body glued so close together, didn’t know why suddenly I found her so attractive from her frowned look and her hair scent followed by her deep breathing. I tried to remove my weight on her while using my palm to support myself back up while my palm slipped on my own semen and I landed mouth to mouth with her.

For some unexplainable reason we started some serious kissing and proceeded to some sexual french kissing. In the process my hands were already exploring everywhere on her body and entering under her tee-shirt. Massaging her tits and tuning of her nipples was done surprisingly without any resistance as my first touch of a female breast made me hard on instantly. My fingers proceeded downwards into her forest (She did not wear back her panty after her orgasm.), and I started dialing the rotary phone. I can feel and see clearly that she’s enjoying so much of my services as she gave out some moan softly with my gentle movements. As I started finger mining her, she grabbed my hand shouting pain and stopping my action. I insisted inserting my middle finger slowly when I felt that she gripped my wrist with all her strength.

Jess: “Boy, very pain!”

I ignored her while inserting further in and out diverting her attention by lifting her tee-shirt and began sucking and licking her pinkish nipple like a hungry baby. While she was enjoying with her eyes closed, I positioned myself on top of her stroking her clit while quietly sliding my 2 IC into her. With one push I entered her while she gave out a mournful cry, gripping my arm again with all her might. I felt so warm, wet and tight inside her while penetrating in and out, it felt so good as I bonked her harder and harder, she gave out this moaning softy with every charge I made which brought me to my peak and I came in her. Having this satisfaction that no words in my dictionary can describe.

We stayed hugging each other for some time till I found that my 2 IC was bloodily stained. Wow, she’s a virgin!

Jess: “Did you shoot in?”

Me (Acting blur.): “I guess so!”

Jess: “What if I get pregnant?”

Me: “Then you will be the mother of ah boy junior loh!”

We both laughed away…

Chapter 3 – Happy family

Jess became my FB during her week stay at our house when finally her mom (Aunty Amy.), flew back from her business trip, which meant she would fetch Jess back. Jess was very sad on her last night so I accompanied her in the room till morning without any sleep.

Soon dawn broke, as she volunteered to visit the supermarket, wanted to make me a special meal. She insisted that I took some rest and promised to wake me up once lunch was ready.

Aunty Amy reached our house around 10 am directly from the airport with her luggage as I invited her in. Aunty Amy had divorced with her husband when Jess was 4 years old, she was only 20 years old when she brought up Jess all by her own. Yes, Amy was 31 years old now, a very successful career woman, got the brain, had the looks with a lot of suitors but were all rejected. She was about the same build as Jess, but with loaded front and back.

Amy: “Ah boy, how are you? Where’s your parents?”

Me: “They went for mahjong session last night and won’t be back till late noon, make yourself at home aunty.”

Jess: “Mom, I am heading to the supermarket to prepare lunch for ah boy, can we leave after that?”

Amy: “Sure darling, I miss your dishes too. I can wash up before joining you both for lunch.”

When Jess left, I guided Amy to Jess’s room. While having some short conversation, I monitored Amy body comparing them with Jess (Wondering if Jess would out beat her in the near future.). Leaving her, I went back to my room to take a nap. I was fast asleep while a shadow woke me up from my dreams. It was Amy that was standing beside my bed with only a towel wrapped over her, those curves, those B+ cup boobies, her wet looks. OMG, that was really a MILF. When I was drooling, I noticed she was staring at my 2 IC where I came to discover that it was sticking out from my boxer stiff and hard.

Amy: “Ah boy, you have grown well.”

Me: “…”

Amy: “Is that the longest you can get?”

As she sat on my bed, she grabbed my 2 IC and started to pamper it. She was good at it, mingling my balls with her left while stroking with her right. While to my surprise, she bent over and started licking and sucking my monster. Just when I was enjoying her skills, she started deep throating that really weakened my legs. When my 2 IC reached its potential length, she moved on top of me positioned my monster into her clit and started riding and rocking above me.

She removed her towel revealing her great assets bouncing vigorously in front of me, her pokey, light brownish nipples, and her model like figure… Stretching out my hand cupping and squeezing her wobbling boobies while tuning her nipples made me felt so high.

Amy: “Let me know when you are coming, I don’t want you to ejaculate inside.”

Me: “Ahhh ahhhh … Ok!”

After a nice three minute ride, changing to a few other positions.

Me: “Coming coming!”

Amy quickly escaped and stuffed my monster into her mouth as I released my army with great pleasure. She sucked so hard again, giving me a weak feeling as I saw that she had swallowed all my cum and she proceeded licking my dick dry.

Amy: “I must admit that you have a huge and powerful penis that adult men envy!”

Me: “…”

Amy: “I was just curious where the other bathroom door link after my bath and happen to see your penis! We should try this more often ya?”

Hearing the opening of the main door, Amy rushed back to the bathroom.

Chapter 4 – It was my moves

The school holiday ended as I was promoted to Secondary 3.

Miss Chee, who became our form teacher, was a 23 years old NUS graduate. She had a shoulder length straight hair with short fringe covering all her forehead, oriental looks, about 1.6m tall, slim build with about 32C – 26 – 32. She used to have a boyfriend that came to fetch her every day, but MIA for already a week. It’s unavoidable to get punishments from her, even just for not paying attention in her class, so my stay-back after school occurred almost every day. I even got a nickname as Miss Chee’s pet.

One fine day, I was caught fighting with a schoolmate in school and got confined in a class by our discipline master. Miss Chee pulled me out after she found out and provoked a meet-the-parents session in another class. (I was not at all afraid due to my rebellious character.) I was brought to a room all alone with her and also our first time that we sat so close together where I got to smell her perfume and had some body contact.

Miss Chee: “Ah boy, why did you fight? You made me very disappointed and heartbreak you know? You were a brilliant kid, always did well in exams, but followed the wrong group of friends. That’s why I always hold you back after class trying to separate you from them!”

Me: “Miss Chee, the guy that I whack said bad things about you!”

Miss Chee: “What did he say?”

Me: “He said that you are a slut that needs men accompany, that’s why you made me stay back to be your sex slave. I was so agitated and was uncontrollable that time.”

Having eye contact with her, I saw tears forming in her eyes, after I replied and added on saying.

Me: “I love you and I cherish our relationship, I won’t allow anyone to spoil the image of you and I swear.” (Raising my volume.)

She immediately broke down and cried, hiding her face on my shoulder. Comforting her by patting her hair, I got a chance to see her pink loose cardigan exposing her tank top with opening showing her cleavage. Covered with these oversized white lace bra just loose enough for some spectacular view of her pinky little nipples. I got aroused by the sight and my 2 IC responded to it. When patting her back, I was stroking her bra strap taking some advantage of her. It took a while before she gained her calm, withdrew her head away from my shoulders. While she was gaining her upright position, her hand accidentally brushed on my hardened 2 IC.

Miss Chee: “What’s that? Is that a weapon that was not supposed to bring to school?” (Without much thinking.)

Me: “It’s a weapon all right!”

She immediately insisted that I surrendered the weapon to her.

Me: “Miss Chee, it is not what you think!”

Miss Chee: “Take it out now! You bad boy hiding it there!”

As she started checking and touching my pants.

Me: “No, there’s nothing there!”

The more resistance I made, the more eager Miss Chee reaction was. As we struggled, her cardigan happened to get tangled with my pants and snap, my pants gave way and down it went, greeted by my full grown 2 IC head peeping above my undies.

We both went stunned for a second as she blushed.

Miss Chee: “Why are you wearing an undersized underwear?”

Me: “Not undersize, my dick was just too big!”

Miss Chee: “Ya, right!” (While she gave me an opposed face.)

Could not bear to lose, I pulled down my underwear showing my red full grown monster. She responded with a dropped jaw, with her eyes nearly popped out as she bent for a closer look, tapping my dragon head like a curious cat while exposing her cleavage of her 32C boobies again. When I was so engrossed on targeting another view of her nipples, she turned bolder exploring my monster with both her hands. I went on coaching her my regular stroking method which she adapted quickly. Happily playing with her new toy, I began my attack on her boobs unhooking her bra strap at her back which she jumped to a shock.

Miss Chee: “What are you do…?” (Before she can finish her sentence, I kissed her.)

To my delight, she did not move an inch but gave in to my approach. She was so engrossed with my kissing where she never even stop my hand, which was already there squeezing and pumping her boobies. Shifting my kisses to her ears and neck, I managed to distract her taking her cardigan off, lifting her tank top and bra to a level, revealing her two proportionate round firm melons.

My sucking of her nipples made her so vexed that she barely looked at me. Working on her clit, my hands went into her panty stroking her frontal wall making her so wet ready for my insertion. It never took too long to position myself on top of her and stuffed my entire monster into her as she gave out a soft moan. I increased my momentum ramping harder and faster that made her moan louder in pleasure, breathing deeply like she was running a marathon. I covered her mouth to sustain her volume while enjoying a good five minutes of ramping till I exploded all onto her belly. She looked so exhausted jerking away with her eyes shut while I added another wonderful moment to my diary.

I was told that Miss Chee’s boyfriend broke up with her a week before, that made my early approach successful.

Chapter 5 – Dreams came true

There was this girl named Wendy who got transferred to our school this year. She’s about 160 cm tall, long hair, and got the looks that stood out in class photos and made you want to look again. It so happened that she joined our class and made going to school more interesting. Soon she became our hottest topic and many guys’ dream girl in less than a week, making her so unpopular with girls in our school. She never had any close girlfriends and was always surrounded by guys and due to my relationship with Miss Chee, I never got any chance to get near her.

When I thought nothing was going to change this situation, Meiling suddenly appeared in the picture. I don’t know when they became good friends when one day, Meiling tapped my back as I was heading to the toilet for a smoke.

Meiling: “Hey, dua ki (Big one.). How are you?”

Me: “Hi!” (Surprised to see Wendy walking beside her.)

Wendy: “Meiling, why you call him dua ki?”

Meiling: “Haha, I show you. Come with me.”

As Meiling grabbed my arm, dragging me into the gents.

Wendy: “Meiling, it is a boy’s toilet!”

Meiling: “Come in lah, don’t worry!”

Me: “Don’t play lah!”

Before I could resist, I was then being forced into the toilet while Wendy followed behind us. Before I can dodge her approach, Meiling’s fast hands already started unzipping my pants pulling out my 2 IC. Wendy was shocked, speechless and standing there watching while Meiling already started stroking it. Soon my 2 IC turned into a monster, while she pulled Wendy’s hand on my monster.

Meiling: “See, isn’t it big?”

Wendy was rather conservative at first, but blended into the stroking quickly. Having a school flower masturbating for you was so much enjoyable. I hugged Meiling as we started french kissing. Meiling was so good till I lost control and started unbuttoning her school uniform. I took off her bra and exposed her boobies and started pumping and squeezing them.

Meiling: “Ah boy, aren’t you afraid of Andy if he finds out?” (She whispered softly to me when she’s already panting away.)

I was so engrossed that I went on sucking her nipples without thinking of the consequences and the consent from both the girls. I went further down to explore Meiling’s clit where I found that her panty was already soaking wet ready for my insertion. I turned Meiling around to have her back facing me and started mining her wet juicy pussy with my experienced fingers. She looked so sexy bending slightly with her skirt rolled up waist high advertising her freshly ass as I smacked them. Enjoying as they trembled.

I finally made my move, inserting my monster into her and began to bonk her. It will seem like she was craving for my monster as she rocked herself without me putting any effort. While Wendy was so lost at the time, staring at our progress, I grabbed her in my arms and started kissing her. She tried to push me away, but was locked by my arms with my hands already on her boobies. She soon found that struggling was useless and surrendered herself to my control. I went wild, unbuttoning her shirt stripping her naked with only her panty on and started some serious petting with her.

She looked so shy with her blushed face standing beside me motionless, waiting for my next move. As I brushed through her body and started licking and sucking her gorgeous pink cute nipples. I changed my target and inserted my monster in her. She was so tight as compared to Meiling as I can feel her trembling in pain while giving a loud moan with my monster forced into her clit. Meiling participated by kissing me and stroking her own pussy while my hands were grabbing her well grown boobies. It never took me too long to ejaculate raw into Wendy, while kissing Meiling which I never expected and felt so extremely high in my life.

I was then forced to buy Meiling lunch for the entire week after she made Wendy lost her virginity to me!

Chapter 6 – Strange encounter

After having 3P with Meiling and Wendy in the toilet, we managed to follow up with a few more wonderful threesome successions in my house and Wendy became my official girlfriend. As I thought I already had enough girls in my diary, I met this JC girl.

It happened on this day when I was going up to Wendy’s house. I was on this bus sitting near the exit when a group of JC girls in their uniform came abroad. They all stood near the exit as all the seats were all occupied, chatting and laughing loudly. There was this girl that drew my attention, standing next to where I was seated, looking somehow very familiar. She was standing so close to me that she was actually leaning against me while talking with her friends beside her. The bus jerked and rocked her body against me which she didn’t seem to bother, giving me a hard on. She smiled at me and continued chatting with her friends. The bus was not really that crowded, which she definitely had plenty of room rather than standing there having body contact with me which lasted about ten minutes.

As I stood up ready to alight, the bus gave a sudden jam and yes, we all lost our balance as she accidentally hit my monster to gain her balance. She blushed, releasing her hand.

Girl: “Sorry, sorry!!!”

Me: “It’s ok.” Smiling back as I made my way out of the bus.

When I hopped out the bus, I found out that I should have alighted at the next bus-stop cursing myself as I walked all the way to Wendy’s unit. When I was outside Wendy’s corridor, I overheard a conversation between Wendy and another girl.

Girl: “His one was damn big lor!”

Wendy: “My ah boy’s one is the biggest!”

Girl: “How big can a Secondary 3 boy get?! This guy on the bus was handsome and I purposely touch his dick and wow it is huge!”

Wendy: “Ya ya, you pervert. Ok, I take photos of ah boy’s one and show you!”

I was shocked when I heard that and went on pressing the doorbell. After being invited into her house I found the JC girl that I mentioned on the bus was sitting in the living room. I can sense that she was shocked too when she saw me, with her face blushed having this really shy look on her face.

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