Something happened recently initiated this need for me to put in writing about the lucky and wonderful life I have had till now.
Recently I met up with my ex-girlfriend about 8 years back and we chatted about the time we had together and the threesome we had back then and it hits me like a brick when I totally forgotten some details and the name of her friend who we so intimately share several threesome sessions together.
Such is the effect of getting old.
Instead of going the way of conventional blogging channels, I have chosen to write about my escapade / life story here. The following narration of my experience are 100% my own.
I will write as what I could remember and some of the timeline will be fu*ked-up but what-the-heck.
Never wrote sex stories before and don’t really know where to start so be gentle and accommodating will ya.
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Background:
I am 32years old now, still boyish looking but put on a pound or ten.. with receding hairline, busy working these 2 years, comes from an above average income family back then and would like to think myself as a nice guy.
Back then: secondary school time till late twenties, I am considered good-looking (boyish), lean not fit and bulky (to the extend in sec sch, am skinny), eloquent, playful and excel in everything i touch (games, sports, CCAs etc) except academically which was at best above average.
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Act One, Scene One
“I hate girls!”
Octoberguy when he was in Primary 6 (1989)
I think men will go through a “girl-hating” stage about the time before puberty sets in (and that is before the age of the internet which makes informed-puberty much earlier these days).
Mine was pretty extreme (I guess) where I almost kept avoiding them, too engrossed playing catch, football to realise that many girls are secretly or openly admiring me.
Valentine’s Day of my first year in secondary school, I recieved 6 gifts from admirers same age or older than me. That’s two months in school and I am creating quite a stir the the opposite sex in the new environment.
Still stuck in the “girl-hating” mode, I openly threw all the gifts into the hall rubbish bin (what was I thinking!!??) and quite rightly being confronted by some secondary 3 guys claiming to be the big brothers of their “sister” and demanded an explanation as to why I threw her gift away. Needless to say, they are ah bengs and I went home bruised after they whacked me in the school toilet.
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Act One, Scene Two
“Men and Women lay down together on the same bed will incubate the egg and thus have babies!”
Inside Octoberguy’s mind when he was in Secondary 2
Ignorant, lack of sexual education or parents talking to you about the birds and the bees, this was how ignorant I am back then till the good old age of sec 2 nearly sec 3! Laugh all you want guys.
With no internet, no porn clips, no proper sex education system, no widespread communication channels like sms, mobile phones, liberal TV programmes, kids back then rely on friends (word-by-mouth) to know about sex and even then… misleading and mal-information were aplenty.
I have absolutely no exposure to sexual content until sec 2 when my friends who were all quickly experiencing what their hormones were doing to their body and brains, that only than sexual topics were brought out for public discussion among us.
I have yet to experience puberty; i.e masturbating and watching porn or have a girlfriend, when I was caught by my dad having a “blue VHS tape” in my school bag. And that is so unfair! Because I took the tape from my clique of friends just because they were circulating it and I am afraid of being called a “wooze” if I didn’t . Damn… had a good lecture from that on that one.
Note: Sorry for the lengthy non-sexual content till now. It just came to my mind and being a journal of sorts, I thought I would like to have all the above in it as well.
Act One, Scene Three
“I’ve got a big cock!”
Octoberguy’s mind when he was in Secondary 2 (1992)
It was at a good ripe age of (Sec 2) that my first sexual encounter took place. By then, I had accepted girls in my life and in fact, most of my good friends were females and had quite a number of “jie jies” (self-proclaimed sisters; popular culture back then) took me into their wings and showered me with lots of attention which could make any pop-star proud.
It was close to end year of sec 2 where we were thrown to some leadership training camp for 3 days 2 nights where I discovered something which I should have long ago.
While in the shower after some water activities, we guys were showering in the common bath area, the usual publicly shy me had no choice but to bathe without doors to the shower room. There it was an awakening! - that I realised as well as some of my fellow class and school mates that I am well hung. And the fact they called me names; like elephant make me even more shy and awkward and this was quickly speculated among the girls. I did not knew the good effects and did not use to the best of my advantage until a year later.
Anyway, I fell in love with a cute little classmate of mine whom many would not think much of. My “sisters” were shock when they found out that I liked her and tried to talk me out of the puppy-love situation as there were lots of pretty girls going after me, including 2 of the most prettiest school babes but .. my perception of love wasn’t lust and even until now was unconventional I guess.
During the camp, I made my move and asked her to be my canoe-mate and we had a very good time really knowing each other. Her name is Jessica.
Jessica is short, petite, cute and sweet. Yes, the description were conservative and non-sexual which clearly illustrated my clean and unpolluted mind back then. 3 months after the camp, we were an item much to the dismay of some.
Act One, Scene Four
“Oh my god! You got nice breast” … “Oh my god … so BIG!”)
Octoberguy upon seeing Jessica’s naked body and Jessica seeing Octoberguy’s ….
Sec 3 began with a BANG! We were together.. After a few months of courtship. Pure and innocent as it was, I was growing up fast and finally eager to embrace the calling of puberty.
Till now, the most we did was holding hands and a peck on the cheeks and I had been having thoughts of taking it to the next level! – Frenching….
Little did I know that I am in for a far greater surprise. Upon reaching her empty house one afternoon, I hugged her as we sat down on the couch and eager to stick my tongue into hers only to be pushed away by her..
Jessica said: “it’s very hot… I want to take a shower…”
“Ok, I’ll wait.” said I slightly dejectedly.
Jessica shocked me and said: “Let’s bathe together.”
I fell off the chair… under the disguise of the innocent face of Jessica, I cannot believe what I’d just heard.
And lo and behold, I said: “no la.. you go ahead” (Go ahead and slap me people)
And Jessica went ahead without me, leaving me on the couch wondering what the hell is wrong with me. Trying to be act gentlemanly at a very wrong time.
She came out of the showers wearing an oversized T-shirt and shorts and she handed me a towel for me to go for my shower. Half-way through my shower, she knocked on the shower door and asked if everything was ok… and I answered yes (ya right.. it’s ok my ass … I just started regretting her offer of showering together!) and suddenly my school uniform, pants and underwear fell to the wet floor.. as her knocking caused the flimsy hangers behind the door where I hung my clothes to dislodged from its position.
I emerged out of the shower with my wet shirt and towel around my waist as my cotton underwear and pants were very wet. Telling her what happened, she quickly went about looking a T-shirt and shorts for me while I am hanging the wet clothes in her room.
From behind me, she said: “Take off your wet uniform first” and I did without turning around and suddenly, she pulled my towel wrapping my naked lower half off and giggled girlishly. I quickly cover my lower body with my wet uniform and turn around and face her wanting to ask what the hell when she said: “oh my god, … so big”
Then I realised that my well hung penis wasn’t properly covered with my makeshift towel. Feeling awkward and not wanting to turn around with my bare butt facing her, I froze and don’t know what to do but to stand there and blush.
“Give me back my towel” I said
“Shy ar? I saw already ..” she teased
“… arr…” I responded. “Not fair, you must let me see you naked too” I mustered.
“Okay” Jessica responded with a soft voice and swiftly pulled the oversized T-shirt off her, revealing her pair of soft, white breasts and walked towards me.
“Oh my god, you’ve got nice breasts” I said as we hugged and frenched.
My cock was erected but our first sexual encounter did not progress beyond kissing and freching in the buff. Partly because, I had absolutely no idea what I am doing and partly because the kissing and the body contact felt so good, and by just doing that was enough.
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Act One, Scene Five
“It cannot get better than this”
Octoberguy’s thoughts
My relationship after that fateful day with Jessica got progressive more sexual. Each time, we ended up frenching furiously naked but no sex, not even close.. no fingering, no blowjob not even masturbation , she did not stroke or out rightly hold my cock except for some light touching and brushing against her body until almost the time when we broke up.
Months on, one afternoon after school at her place, instead of stripping her totally, I told her to leave her uniform on as I unbuttoned her top and unhooking her bra revealing her 32B breasts through the pure white uniform while we fiercely engaged in a tongue battle.
Suddenly, she stopped and mentioned that recently, her friends had been discussing about the size of their boyfriend’s manhood and my penis was the centre of the discussion.
After the sec 2 camp, there already had been talks about the size of my manhood and her friends were saying to her how lucky she was having gotten me; “the boyish boyfriend with a BIG cock” and they had asked her how big my cock really was….. then out of nowhere, she pulled out a plastic ruler (those cheap long white and transparent type) and measured my erected cock.
I find it amusing and try to resist, but sitting on the couch and her kneeling on her knees in between my legs was too arousing and I let her do as she pleased. That was the closest in months that her cute little face and hands were on my cock. She got the cutest smile that I ever seen as she joyfully use the ruler and outline my cock and she glanced up at me and asked: “Measure from where ar?”
I smiled and said:” From the tip of my cock to my balls loe”
And she happily smiled and go back to tracing the ruler on my cock only to proclaim: “ 17cm! … long or not ar?”
I shrugged my shoulders ,speechless.. and she said: “They also got ask me if I had given you a blowjob before?”
My senses went to overdrive when I heard that and replied: “And what did you tell them?”
“Too big la .. cannot put in the mouth and so shy’ she said
She then opened her mouth really wide and move near my cock, trying to imitate doing a blowjob. That scene made me so high and it was lodged in my memory after so many years.
Jessica then dropped the ruler and for the first time, using two hands to wrapped around my cock and looked at me: “You want me to give you a blowjob?”
With a little tinkling sensation in the small of my neck, “If you wanted to …” is all that I can muster.
“But so big and my mouth so small .… ?” She asked coyly
“Seldom” I replied as she started the upwards and downwards motion with her hands.
The fact is until the first time frenching with her I had never masturbated and even after that I had only masturbated without ejaculation a couple of times while thinking of her … (again, I told you I am a late bloomer)
“You want me to suck it?” She asked again
By that time, I was at the verge of going crazy with her stroking and could only say: “ya” … when I felt tongue to my cock.
With 2 hands still wrapped on my cock, Jessica licked the tip of my cock like a schoolgirl with a lollipop and in less than a minute, inexperience and unable to control, I blown a huge load in her face, mouth, hands and hair .. and she scream and recoil like you would when someone spilled the coke from the can on the canteen table.
Embarrassed and quick on my feet, I stood up and reached for some Kleenex and start wiping my cock, trying to stop the ejaculation flowing to the floor.
Jessica sat on the floor shocked and probably amazed, speechless while I panicky trying to recover from the situation, she reached for my cock and grabbed it gently and said: “It’s okay.. Don’t worry, sit back down”
Stuttering and trying to find a word besides repeatedly apologising, I sat back down to her instructions and looked at her.
My cum was all over her face, hair with her hands on my cock and looking at me, she said again: “It’s okay”.
I looked at her and said in my mind: “it cannot get better than this!”
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Act One, Scene Six
" Feel so good Jess, how I wish you to suck it”
Octoberguy to Jessica on a double-decked bus
Jessica and I continued to have a beautiful relationship even without much sexual contact later on as exams were getting close and our time together were restricted.
The pre-matured ejaculation incident was my first taste of a so-called blowjob, I had after that not received another until very close to our break-up. That was near the mid-term exam period
One day after our individual study group session, we met at the bus-stop as agreed and for us to have some time together by sending her home, we board a double-decked bus and sat right at the back and held hands.
She mentioned that she missed petting with me and lament on the fact that how we don’t have time after the previous incident to be intimate.
I moved her hands closer to my crotch and told her that I felt the same way and asked if I could go to her place. She declined as her parents were home that day and she moved her hands and rest on my cock and stroke it. Oh my god, so exciting and stimulating I thought and I moved over wanting to kiss her. She recoiled immediately and said:” cannot la, we in uniform and people will see, you enjoy okay” and she unzipped me and exposed my erected cock and stroke it.
“Feel so good Jess, how I wish you to suck it” I said.
Without notice and in an instance, Jessica bend over and engulfed my cock with her mouth and sucked my manhood. It was the first time I experienced a mouth to my cock and it felt incredible. She was sucking it fast in an up and down motion and her little mouth can only reach one-third of my shaft and her hand was still holding to my lower shaft as she sucked. (It was later when I am more experienced that I understood that she must be uncomfortable at that time especially with her inexperience, the place and knowledge of giving head)
I am totally in the realm of ecstasy and only regret that I can’t enjoy that moment in privacy as I gripped the handlebar of the seats in front of me and look feverously to the front of the upper deck as there were passengers and am worried if they knew what we were doing behind them.
Jessica wasn’t discreet at all due to her inexperience and the sound of sucking plus the pounding of my heart made the entire blowjob loud to me and within a few minutes or even less, I ejaculated into her mouth.
Calmly this time, I let the full ejaculation happened and truly enjoyed it while Jessica’s mouth was ledged on to my cock and swallowing every drop of my cum.
As she sat upright, she gagged as she start to swallow the rest of my cum and a convulsions of coughs erupted. She bended over to “vomit” and spitting out my cum.
She stopped awhile later and composed herself as people in front of the deck turned over to look at the fuss as I pass her my water bottle, then I saw the mess on my cock and pants; they were all wet with a massive patch of a mixture of cum and saliva.
We then frantically try to wipe and tidy up myself as our stop approached and I had to be contented with using my bag and blocking the still wet and unsightly mess in front of my pants.
Act One, Scene Seven
“Jessica said you got a big cock, a lot of people said you got a big cock… sure or not”
Jessica’s friend Limei asked Octoberguy
I am eager for more action with Jessica and the month of examination was simply agonising. Worst was to come when I heard that Jessica will be away with her parents for the weekend to Malaysia right after the last paper and could not join us to a class trip to East Coast.
I prepped the Saturday and headed to East Coast with one of Jessica’s friend Limei, as she was the beverage in-charge and I was staying closest to her hence have to help her carry stuff.
Limei was way prettier than Jessica, curvy and taller. She had a “ah lian” kind of attitude although she isn’t one. I am not sure if she was bustier but her height sure amplified her assets a little. Dressed in a pink tanked top, white shorts and a cap, she emitted a radiant of sunshine when I met up with her.
On board a bus to East Coast, we made small talk and was about to reached the topic of my sexual relationship with Jessica when we had to change bus. Being not a kiss-and-tell person, I diverted the topic while on the next bus.
The day went joyously and I never thought much of Limei as there were many friends and girls around and I being me, were either busy playing ball, swimming and roughing with my guy mates or joking with the girls classmates.
After BBQ, we packed up and headed home and me being back alone with Limei. We small chatted and dozed off on the bus as we reached the interchange.
While walking to her place, she mentioned about their group girls’ talk with Jessica and she ask: “Jessica said you got a big cock, a lot of people said you got a big cock … sure or not?”
Feeling awkward, I stammered and replied: “you ask Jessica loe …”
“Jessica said you got 14cm when not erected and 17cm when erected .. so big meh?” and following that she launched a battery of questions like: “You want to fuck Jessica?”, “is her blowjob good?” while I kept quiet and only occasionally managed a few “arrr..”
Finally we reached the landing and took the lift up, as it was almost 11pm, there were no one along the corridor and her place were dark with her interior lights off. As I put the things down on the floor while she was unlocking the front gate, she said: “You know, I gave Jessica pointers how to give a blowjob…..”
I managed an: “Is it?”
She replied: “Ya, I experience what… so I qualified to teach her.”
“With Mark?” I asked wondering if it’s my lucky friend who had been hitting on her early this year.
She replied as she opens her front door: “Ya .. and another guy of whom I don’t think you know him.”
I picked up the stuffs and move it into the house while thinking of what to say when she close the front door and said: “Can I see your cock just to satisfy my curiosity?”
I choked and froze.
“Don’t worry, my parents sleeps early and just let me see for a while” she said.
“Here?” I asked and frankly, I am more afraid, helpless than anything and my wet shorts and the pressure means my cock was at a limbo at best. I was thinking how to get out of this situation when she reached for my hand and pull me deep into the kitchen near the toilet.
“Here, it’s safe here and show me, I want to know if you are really that big” she said.
I stood there dumbstruck and motionless when she lean forward and yank at my shorts: “Quick”
With my shorts elastic band caught on my cock (I am not wearing underwear because while playing in the water a second time during BBQ, I wet it and anyway my shorts had a lining so I went bare) she was unable to see anything and she said: “Just show la, see only.. quick leh…”
And without thinking and seriously just want to get out of there quickly, I pulled down my shorts and look away avoiding looking at Limei.
That’s when she goes: “Fucking Big man” and I felt her hand touching my non erected but well hung cock. My eyes darted back to where Limei was standing and only see her back bending over and heard her say again: “Fucking big man” while examining my cock which was steadily woken up to life by her warm attention.
“Jessica’s mouth so small how to suck your cock man??” she asked. “Fucking big man, much, much bigger than Mark!” she continued to manhandle my manhood and twisting it around in close proximity of her face. Then before she said another word, I took a step back and pulled up my shorts.
“It’s getting late, I better go …” I said.
I went home thinking about the whole incident and found it to be very kinky .. maybe , just a little maybe that one day Limei can suck me.
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Act One, Scene Eight
“You failed the test, how could you??!”
Jessica to Octoberguy
My mind was starting to think about Limei when my phone rang the next day.. (house phone.. no handphone that time and no caller ID for me)
It was Jessica: “Free to meet today, I am back”
We met at her void deck and I could swear that I flew to her place in record time.
I wanted to hug her so bad and then I noticed her swollen eyes.
I approached and asked: “Are you okay?”
“What happened?” she replied.
“Huh”
“Why did you pull your shorts down and show Limei your cock?” Jess started to tear up.
“Let me explain, she asked me if she could just see and I actually …” I replied slowly choosing my words carefully and still in shock when she interrupted.
“It was a test, we think you are a playboy, it’s a test, it’s just a simple test and you so freely show her your cock. If she wanted to suck your cock you would have let her right?? Right??! “You failed the test, how could you??!” and she ran sobbing back to her place.
That was the end of my first relationship and needless to say, I tried all means to explain but Jessica will hear nothing of it and with her friends of Limei and others bitches awared of the incident and around her constantly didn’t help either.
I was heartbroken and I hated Limei at that time. Nothing could cure my broken heart, and so I thought.
Act Two, Scene One
“Shit it’s them again! Charlene, protect me ar!”
Octoberguy to his friend on the bus
My June holidays passed slowly as my broken heart begin the healing process. Once school reopens, I was forced to try to reconcile with Jessica as we meet each other in school. But when love turns to hate, there was nothing I could do.
I had been harassed by three Convent girls every afternoon when I am taking a bus home when I am in Sec 4, even, during the time when I am with Jessica. They were bold, loud, daring and irritate the hell out of me and other passengers as they board the bus at the usual bus stop.
Charlene stays about 5 bus stops from me and often goes home together with me. She was more like a sister I never had. She was pretty but a bit big-boned but she was really a nice person.
The three convent girls were my age, two Chinese girls of very lean figure and average breasted, in fact both were very pleasant looking was Linda and Jaime, the other a bit like Malay, Mathilda but fairer, bigger breast and had a very cute smile looks okay.
The first time we bumped on the bus, they pissed me off so bad that left a negative impression. In fact I am scared of them when Charlene weren’t around with me. (Ya .. go ahead and call me a wimp)
The first time we met, I was with Charlene, that day Charlene was wearing her very ugly specs and had a bad hair day I guess so she actually looked horrible. The three convent girls boarded the bus and kept laughing loudly.
Actually I found them cute on first sight until they stood quite near where Charlene and I were sitting. We were sharing the earphones on a walkman when they noticed me and started whispering and looking my way. I knew that my boyish looks got the charms but am getting a weebit uncomfortable by their increasingly indiscreet way of trying to get my attention when Mathilda mentioned loudly: “Such a cute guy with a pig” and three of them erupted into laughter.
I looked away in disgusted immediately and they continued their taunting, while Charlene was dozing off and listening to the walkman.
I told Charlene later on and she always stared and be more fierce-looking whenever they were onboard.
After that incident, they had tried many things like, walking up to me and talk to me, throw things and notes at me etc when Charlene was not around. I never responded in anyway to them and always avoid them until some months in August after my break up with Jessica.
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Act Two, Scene Two
“Hey, how about coming to Mathilda’s place to study Saturday?”
Jaime to Octoberguy
After the break up, I took a more heck care approach to girls and the three convent girls were my distraction, I guess.
During one of the trip home without Charlene, I bumped into Jaime on the bus. She saw me and smiled and sat beside me. Somehow, she looked less evil alone than with her evil twin sisters…. And I smiled back.
She initiated small talk by saying hi and stuff which I can’t recall. She sounds absolutely harmless and sweet and we exchanged numbers at that first time alone.
She actually called me few days later and chatted about school and relationships stuff. A week later, she invited me: “Hey, how about coming to Mathilda’s place to study Saturday?”
And I went.
Mathilda stays in an upscale neighbourhood and I had to meet Jaime for her to guide me to the secluded neighbourhood far from the main road.
My eyes popped when I saw the huge bungalow and the even bigger front yard when we reached her gate. In fact, so huge her place was that there was a Jacuzzi indoor and pool outdoor. Mathilda is from Indonesia and her parents were rich business people who stay in Indonesia to care their business for half of the year. She stays alone with three maids and a guardian in Singapore during school term.
That day, we were all alone while her maids went lucky plaza for their day off. This is one adventure that changed my life.
While exploring her huge house, we finally rested at the big air-con living room and naively, I started to take out some books and place on the table. The three girls started their nonsense by joking and teasing me for being so studious when Mathilda took out a pack of cigarettes and some beers instead of my familiar coke and chocolates.
They cracked open the beers and passed around and I took a sip and a draw of the ciggs. Although never tried before, I sure hid and took it like a seasoned drinker and soon we were joking and laughing at how red my face was and some rubbish chit-chat.
Then out came the poker cards and we played heart attack for awhile and before long, we were behaving like long time friends; laughing and patting each other backs and giving hi-fives.
Fuelled by the fun and beers, Mathilda took off her top and revealed her lacy black bra and urged us to follow her for dip in the Jucuzzi. She pulled me and the other two girls to the basement where the Jucuzzi was; waiting, already filled with bubbling water.
I was stealing glances at Mathilda’s big breast when she took off her shorts and jumped into the Jucuzzi with the two girls following suit, leaving me wide-eyed and mouth opened.
“Come on” they urged “Don’t be shy, we already in our undies also not shy already”
Not knowing what to do and totally unprepared, I was thinking about how awful I will look with my ugly underwear and unappetising skinny figure when they start splashing water at me.
“I don’t have any spare clothes ….. Do u have a burms or swimming trunks?” I countered desperately.
“No need la, just stripped naked loe” said Mathilda, definitely high on something.
“Cannot la, you all also not naked, I shy man.” I said
Next, Mathilda’s bra came off, her at least C cup breast bounced loose from the constricting bind and off came her undies and she threw at me and said: “na.. naked already, come on” The two girls screamed and cat calls wildly.
“Fuck it la” as I started to slowly take my Tee off and pulled my shorts off as the catcalls got even louder… I stopped at my underwear and turning my back against them. (I almost considered wearing my underwear into the Jucuzzi) when Jaime and Mathilda cooed: “Take it off and turn around”, “Don’t be shy”
So off came my undies and I backed up and turned around and the girls collectively exclaimed: “wow .. !” and I was in the tub.
Act Three, Scene Three
“Fucking shit! Oh noooo..”
Jaime exclaim
Mathilda threw a pack of playing cards on the floor and proclaim that we shall play Truth or Bare.
I caught her smiling at me and she said it care freely: “Surprise”
Although all of us protest in different degree, it was obvious that the Birthday Girl was going to get her way and I believed Jaime and Linda won’t be too shy about it. We had a bit too much raging hormones mixed with alcohol in us to actually reject such a game. Kelly also seems cool about it and claimed that she won’t mind at all but from my observation, I KNOW she is scared and just a loud mouth.
The game was nothing like the normal “Truth or dare”. It was the steroid and sexual version. The game goes that everybody will draw two cards and the one with the highest sum of the two will be the winner and the lowest will be the loser and has got to do a forfeit pre-determined by the loser of the previous round. In the event of a tie for winner and/or loser, both will have to draw a third card. After spending quite some time haggering over the rules of the game and nature of forfeit, we agreed that the forfeit must be agreeable with at least 3 people out of the 5.
Mathilda being the host will start the game by naming the forfeit. “Loser of the first round will strip naked for the rest of the game. Nobody except for me and Linda opposed and were overruled.
I had a strange feeling about what Mathilda told me the other day to be daring and not to be shy had to be my guiding light that night.
After some anxious moment, the result was out and to my delight, Jaime lost and she openly performed a lap strip dance for Mathilda as her birthday present. I was already hard before she even took off her dress. Jaime being the loser named the next loser would also need to strip, then the rule’s weakness was exposed and Mathilda quickly pointed out that should Jaime lose again and she can’t performed that forfeit, the winner will have absolute say as to what she will do.
Without too much hesitation, we proceeded.
“Fucking shit! Oh noooo..” Jamie moaned when she lost the very next hand.
“You can’t be any unluckier, haha” We burst out.
“Woah ..! Okay now you got to jiggle your breast throughout the next hand” Mathilda instructed and laughing
“Wa Lau… lame leh” Jaime exclaimed “Okay the next loser will strip! And if I lose again, I surrender.”
The sight of Jaime trying to deal the cards and shaking her boobs was more hilarious than sexy for me.
It was a feast to my eyes as Linda and Kelly subsequently lost and was naked. Kelly had an athletic body with small but cute firm boobs.
I am sooooooooo lucky and I said a silent prayer.
[b]Act Three, Scene Four[b]
“Next loser will have to lick me till I reached orgasm … now that I am totally aroused.”
Mathilda dictated
I was next to lost and Kelly seeing me naked for the first time had the same awe reaction as the other three. She was sitting directly opposite me and the look on her face when she saw my giant cock while I was stripping was priceless. I had trimmed a few days before and it definitely had an effect of not obscuring any length of my 17cm rock hard cock.
“I told you that he got a big cock; bigger that you’d ever seen” Mathilda told proudly to Kelly. Kelly just acted cool and mumbled something I can’t really remember.
I named the same forfeit and I lost, Mathilda ordered me to suckled on Kelly’s nipples for 1 minute. Kelly was very against it was trying very hard change the forfeit. I felt totally uncomfortable as well since its my first day knowing Kelly, but the idea of sucking on nipples can’t be too bad for me.
Mathilda’s order can’t be change and I sat down beside Kelly and with some awkwardness and catcalls from the girls, I bend over to place my mouth on her nipple as they counted down the minute as well as tell me to lick. The minute seems like forever and I did nothing but open my mouth slightly for the nipple to disappear into my mouth.
The level of play was still at a safe stage at this point and again I said out the same forfeit.
Linda lost the next and my surprise was revealed.
“Take away that boy’s virginity, Linda” said Mathilda with a wink and smile.
“What?!” exclaimed Linda “No man”
“Come on Linda, you lost!” everybody except me cheered on.
I was totally excited at this point and I gentlemanly opposed to this forfeit. The arguing and haggering was a lifetime to me when I saw Linda stood up and with a sigh of defeat said: “Okay, but just have the cock inside me and no fucking okay.”
There were many helping hands as Linda stagger over to me and Mathilda told me to lie down.
Linda spread her legs stood over me and said: “Fuck man, this gonna hurts” as she squat down and for the first time I felt Linda’s hand holding my cock trying to position herself when using another hand to caress her virginal.
“God, this is for real” I said to myself and Mathilda crawled nearer to have a good look.
I felt the the pressure of Linda’s weight as she slowly sat on me while in a circular motion, she guided my cock, sliding it up and down her clitoris. The warm and moist feeling of near penetration was intense. My cock head had the tingling sensation and I was totally speechless and not knowing what to do when I felt it, the penetration of the body.
The tight warm love hole of a girl.
“Arhh… arhhh…” moaned Linda in an almost painful pitch. “Arhhhhhhhh…” The little scream followed as she puts her whole weight down and sat on me with my cock totally forced into her.
Instinctively, my hands held her hips and I moved a little when she sat on me when she scream: “Don’t move, don’t move, it’s a bit painful” Her arms holding mine tightly. I was hoping that this moment last forever.
Totally oblivious to my surrounding, Mathilda, Jaime and Kelly had moved closed to me watching intently.
“Can already” asked Linda
With the teasing delay of response from Mathilda, three girls finally gave Linda a break. Linda, stood up in a flash and I got a rush of feeling equalling in the nice sensation of the penetration. She fell back to the floor looking totally overtaken by physical exertion and her virginal was red and with a little moist.
If only I could make love instead of losing my virginity like that.
As everybody settled down, I looked at my moist cock and touch the love juice of Linda on the length of my shaft when I heard Linda said: “Next loser will have to suck Octoberguy’s cock.”
I was in heaven as I felt Mathilda’s mouth engulfing my shaft. The feeling was very different as of Jessica’s. Jessica is tiny, has a small mouth, and lacked experience, Mathilda actually puts a lot of tongue and up and down motion. She totally came over and immediately took over my cock and when I saw she was actually able blow me almost my entire cock; I was very much aroused and so ready to ejaculate. But it was not meant to be my day as Mathilda sat up and ended it prematurely for the watching girls and for my ejaculation.
“Next loser will have to lick me till I reached orgasm or Octoberguy, if you lose then you can fuck me; now that I am totally aroused.” Mathilda dictated
There was strong protest for this forfeit as neither have the girls perform fellatio on a girl before. All of us denied and Mathilda whined and whined and finally she gave in and finally all agreed that the game had gone on far enough but in actual fact we were only playing for about 40mins.
I glanced occasionally at Linda and caught her eyes a couple of times. There was surely a little awkward, shy yet lusting look and I felt connected to her.
That night, we slept late and in the leaving room after many crazy running around the house naked, chasing each other, chatting and drunk in the end. I remembered hugging all of them.
Also another little episode of Jaime and Mathilda trying to force the loud mouth Kelly to suck my cock when she talks about something that she can give an excellent blowjob.
It was with the three of them that I have grown sexually so quickly. Sadly but truly, I also learned that with some looks and charm, you can get into the pants of just any girls.
-——————————————–
[b]Footnote[b]
That day… seems unreal and if you think it is just a fiction story spanned by my imagination, I will leave you at that and never will I defend it. I had said it in the prologue to this writing before.
The names I used were very close to their real names either same sounding or starting with the same first letter. Most of them I still remained in contact with now, although not as much as before.
Please quit asking me for their contacts. You must be crazy to actually ask me for it and expecting me to oblige. I will be even be crazier if I ever thought of giving away their identity. So please…
As I grew older, I heard stories of how wild convent and rich girls can be and I always nodded my head in silent consent but never shared this experience with anyone except a very selected few; who are all girls.
PS: Thank you for all the comments and patience.
woah man..wish i had led a life like yours bro!! must feel damn good to be gd looking..love ur life story (and very envious!!)
Act Four, Scene One
“Be bold, be bold”
Octoberguy
Can’t remember exactly when but it was about the time of the O Levels that I was talking on the phone with the three more often than meeting them for obvious reasons. They are wild but they sure study hard and had fantastic grades.
I was talking to Linda over the phone much more after losing my virginity to her. Jaime was a great friend to chat with though and Mathilda was as before not much of a phone person and eccentric in her communication with me blowing hot and cold.
I generally know two things for certain. One, I am fucking lucky to have met the three “wild” girls. Two, I had the feeling that Linda kind of like me but there was something stopping her from being too out forth with it.
It was very close to the finals one day and I was out studying with my two of my female classmates, Adeline and Ivy at Far East Mac. It was very common to hang out with girls back then and some times it was totally random and spontaneous instead of a fixed clique of friends in the study group.
Adeline was plumb, but not too bad looking actually and has a great personality; very charismatic for some one not pretty. I guess that was the reason why she was the class monitoress for 2 years and the current head prefect.
Ivy was slim, short much like Jessica’s figure, spotting a trendy frameless specs and very adorable and girl-next-door looks. She wasn’t gorgeous or anything and in fact she walks with a little (just a little) limp on her left leg as she wasn’t born with both legs of equal length.
Nobody takes much notice of her much and I admit that a lot of my friends while comparing notes on girls always thought that I had weird taste. I seriously thought she was cute, not as cute as Jessica or any of the three convent, but she was kinda my type, quiet, sweet and I compared her looks to be like the younger version of Zhou Huimin but without makeup and wearing specs; a bit exaggerated I admitted.
Late on, I sent Ivy back as Adeline got to run for tuition and we chatted heartily. She was from a different class from I was and my episode with Jessica did not reached the ears of hers. I can’t help but noticed that Ivy must have a liking for me.
With my heighten sense of confidence and a new found flirtatious nature; well enhanced by the three convent girls, I flirted carelessly with her all the way to her place. Mathilda’s words were floating in my mind: “Be daring, bold ….”
We reached her place at about evening and it was about the time to say goodbye and leave, I plucked up some courage and ask her: “Hey, not inviting me up to your place?”
“Sure, why not, if you don’t mind my messy room” she replied much to my surprise.
Her room was a cosy set of girly furnishing and a touch of artistry with a piano in it. She immediately went to the bed and tucked some clothing away and invited me in for a tour. Her parents were not coming home anytime soon and I was beginning to think that she was cute and what pleasure must be able to have sex with her in her uniform.
I told her to play a tune on the piano and I watched from the chair behind her. “Be bold, be bold” said I to myself again and again.
I walked towards her while she was still on the piano and places my both of my hands her shoulders giving her a gentle squeeze at first and she stopped. I squeezed again and began to massage her and told her to continue and commended that she played well. I sense my chances as she continued with a soft tune and the fact that she did not reject our first-of-any sort of a bodily contact.
I took another step forward; as I pressed my crotch and stomach on her back as I continued my massage. The tune slowed to a wrong rhythm but never stopped. I was embolden and too horny to stop trying my luck and my lower body contacted her body, moving in sync with the tune, my cock rubbed against her back strap of her bra through the uniform and I can feel my cock awaken to the physical arousal.
My cock grew to its full length as I continued the unusual dance of arousal with Ivy and I am sure that she could feel my enlarged crown jewels against her. While enjoying the moment and contemplating my next move, the music stopped and like a well rehearsed dance, the massage and the rubbing stopped.
She stood up and turned around and looked at me and knowing I must say something before she does: “Like the massage?” I managed to ask softly and bend over to kiss her on the lips.
My lips touched hers lips gently and coyly retracted a few micro-millimetres as I looked her in the eye and repeated the action several times as I walked closer to her body.
The experience was like your first kiss, a little uncomfortable, very much enjoyable. Our lips locked, tongues met and we engaged in a well matched tongue twister as my hands guided her body closer to me.
I held her tightly and closer to me and continued my lower body movement, rubbing against her.
Our frenching grew intense as we laid on her bed, laying on top of her, our lips seldom separate, though still fully dressed, our movement mimicked the motion of having sex, as my legs went between hers and slowly spread them apart and my cock went between and rubbing against her privates. I tried to unbutton her blouse slowly but Ivy stopped me by holding on to my hands, then, I heard her moaned as our lips parted for a second.
She must be enjoying it, I thought, as I intensify my lower body movement, pressing harder against her with every up and down motion more deliberate. Though the intention was to get her horny, the gratification had the intended effect on me as my inexperience got the better of me when I felt myself on the verge on ejaculation. I almost slowed to a halt to control it when I felt Ivy’s legs lifted up and gripped on to my hips.
I am glad the gratification got her into the mood too as she took the initiative of rubbing against me with increasing speed. I looked at her intently only to realise that she had her eyes closed tight, breathing heavy and face flushed. I couldn’t hold back any longer and came on my pants when a few seconds later, her legs’ muscle contracted, her fingers dug into my arms and with a few more thrust against my cock, she shivered violently and let out a soft scream.
I collapsed on top of her and we shared a moment, listening to each other’s breathing slowly returning to normal. It was awkward wondering what to do next.
I went back home wondering what was to be of me and Ivy. I had left her place; both feeling embarrassed and had not talked much.
I contemplated calling her when I reached home, but did not know what to say when my pager beeped.
Act Four, Scene Two
“Will you be my girlfriend?”
Octoberguy asked
“Yo! What ya doing?”
I immediately recognised the energetic voice at the other end.
“Jaime? Where are you? Didn’t recognise the number.” I replied
“We’re at Kelly’s place, want to come over?” She asked.
“Na, I can’t, parents will kill me to go out at night on a week night.” As she continued to pester me which later on I politely reject.
The truth is, I am exhausted and am much thinking about Ivy and our episode earlier. I have to think through my course of action before tomorrow. I seriously hope Ivy is not the kiss-and-tell kind of girl or else, the school will have yet another juicy story of me.
The next day, I avoided looking Ivy in the eye as much as possible during recess. I lunched with my guy mates and were pre-occupied with some discussion when Ivy came over and passed me a book saying it was mine and returning it to me; it wasn’t but I got the hint. There was a note in it as I read it while in the class. A few simple words: “Please don’t kiss-and-tell, I am not that kind of girl. We are still friends right?” I heave huge a sigh of relief; exactly the kind of situation I was hoping for.
The next few days, I continued to study with a few girls including Ivy and each time, I sent her home and we ended up doing the same thing as the first time. We are taking our little orgasm time a bit further progressively with a little touching and groping. More importantly, we talked about it and got to know each other better. Ivy is still a virgin, while I made her think the same about me too, which surprised her because of the rumours in school with Jessica and Limei.
Within that week, she finally unzipped me and held my naked cock in her tiny hands. She marvelled at the cock, totally unfamiliar with it and exclaimed that it’s the first time she seen a cock. She was not too in awe with the size, attributing to her innocence I guess, but she did comment that how such a big thing can go into a virginal. Cute.
I was standing with my pants down on the edge of her bed as she used two hands and tugged at my cock. I beckon her to suck my cock as I move my cock closer to her mouth and she shrugged away like a frighten school girl. Well, she is an innocent school girl alright.
“I don’t want” she said “So gross”
“Its okay” I replied with a smile “It will make me feel very good and guys love to see their girl going down on them.”
“But I am not your girlfriend” she looked up at me, holding my cock anguishing close to her mouth.
“Will you be my girlfriend?” I murmured without conviction, knowing very well I just want to get my blowjob.
“Really!?” I felt her grip tighten with that exclamation.
“Yes” I replied loud and clear as if she tightening grip jolt me out of my half heartedness.
She looked at me and looked at the gigantic cock that she was holding so close to her face. Her hands moved along the shaft as she continued to look at my cock. It was a scene to savour but I can’t wait for my cock to be in her mouth. I am going crazy as she continues her slow hesitation and examination of my cock. I inched forward. I reached for her top button of her uniform. I am determined to she her breast today and have her sucked me off.
I unbutton the first button without difficulty or resistance. I try my hand on the second and off it came together revealing a white undergarment. I felt a squeeze on my cock and as I look at what she was doing, I felt a flick of a tongue on my cock head.
“Is that sperm?” She asked.
“I think it is, and it’s called, pre-cum I guess” I replied.
“Don’t taste that bad as they put it.” Came her reply.
I felt another flick of her tongue and another and another. I leaned back to look at her licking. It’s so cute as her action is that of like juicing a ice-tube. She squeezed my cock with her hands and as the pre-cum came out of my cock, she flicked her tongue and devour my juice.
I inched forward and continued to unbutton her top, revealing her bra totally. Rushed and unpolished, I pulled up her bra and grabbed her B-cup breast. Then I felt it, the undeniable sensation of the warm and moist inside of her mouth on my cock. I closed my eyes to enjoy that moment and she said something while my cock was inside her mouth.
“Huh?” I asked and leaned back and look at her just in time to catch her sliding my cock out of her mouth and said:
“Am I doing it correct?”
“Yes. It felt very good” I encouraged.
“Okay” She smile and looked at my wet cock and opened her mouth.
She did not use her tongue much and only trying to go as deep as she could, in and out motion. But the sensation of her seems different as she made a low humming sound which makes me feel…. like I never felt before.
I fondle her breast and played with her nipples. She was moaning as well as taking as much length of my cock as possible. Within minutes, I was close to Cumming.
“I am Cumming, Ivy” I said expecting her to stop but she continue sucking me.
“I am Cumming” I said again.
Out came my cock from her mouth and she looked at me and at my cock again, all these while, both her hands were tugged and pulling at my cock. Not expecting what to do I guess, she continue to tugged at my cock and looked curiously at my cock.
I uncontrollably placed my hands on her shoulders and without delayed, I came. Spraying my cum all over and directly at her face, she let out a scream and pushed me away although my hands on her shoulders were restricting her escape.
My grip loosens soon and she lay back on her bed, exposing her panties underneath her skirt. I stepped forward to look see if she was alright and found her breathing hard, face with a thick white creamy layer of my cum as she lay there hands on her exposed breast.
“Are you alright?” I asked
“Wow ….” She said “Yeah, it’s …. weird, sticky and warm.” She added not daring to move so the sperm will not flow onto her bed.
That’s when I realised that my sperm had plastered not only her face but her specs, uniform, breast and skirt. It’s fucking kinky! I pulled her up and held my cock to her face, still feeling the pulse of sperm rushing through the veins of my hard cock: “Suck it, dear”
She hesitated awhile and opened her mouth.
She devoured my cock slowly, licking up the remaining cum on my cock; her face twitches as if she sucked on a lemon.
thanks for the great story bro! brings back fond memories lol
makes me think of the good old days when the girls were still so innocent