My attempt at sharing my experiences… (Part 55)

By EnigmaofSorrow

Anyway, as expected, Charmaine and I did not last. Her insecurities and
infrequent mental breakdowns pushed us apart.

I tried my best to be a caring and understanding boyfriend, but the stress
eventually got to me. I was juggling track and field, studies and Charmaine.

I did manage to get her to see a psychiatrist about her condition, but she
only attended the first session reluctantly, and begged me not to force her
to go for the rest. She feared that she would be labelled as a
“psycho-case”.

It was after my mid-year common tests that the relationship fell apart. I
flunked pretty badly and had to go for numerous remedial lessons. I was even
counselled by my tutors who told me that I needed to focus, otherwise I
might not pass my ‘A’ levels. My track and field performance also suffered,
and I had a falling out with the coach and the team.

While Charmaine was going through a rough time in her life
relationship-wise, I felt my world falling apart as well. I did not know why
I was even in JC, or how I was going to pass my exams. Charmaine did not
seem to understand this and demanded that I spend time with her after
school. She was relatively free at that time as the University intake had
not started yet, and she was not working part-time. It seemed like I was her
only entertainment and she could not live a normal life without me.

I felt myself drifting further apart from her, and she seemed to notice it
too. We quarrelled frequently and she would vent her frustrations on me.
However, every quarrel often ended with sex. I guess she was trying to use
sex to keep me.

It was also around this time that I became closer to one of my classmates,
let’s call her Nicole.

She was a quiet girl, one of those that you would not give a second look.
She was slim, had neck-length hair, and was not one of those JC girls who
would alter their skirts so short that you could get a hard-on just by
walking behind them. In fact, she was so quiet that I never really talked to
her despite sitting next to her for a couple of months.

Nicole noticed that I was constantly falling asleep in class, not handing in
my assignments on time and generally being an ass to the people around me.

Anyway, I fell asleep during a GP lesson one day and was nudged awake by
Nicole.

N: Hey! The teacher is staring at you.

I groggily awoke.

Me: Huh?

N: Don’t sleep.

Me: What ever.

And I placed my head on the desk again but she nudged me again.

Teacher: Enigma and Nicole, get out of my class!

I awoke.

Me: What the fuck is this? Primary school?

A collective gasp was heard around the class. Suddenly, it really felt like
Primary School.

Teacher: What did you say??!

Me: I said fuck. What’s the big deal?

The whiteboard marker flew towards my direction. Somehow I caught it, and
broke it in half on purpose.

Me: What’s your problem?

Teacher: Get out now. Both of you. And Enigma, go straight to the Discipline
Master.

I looked at Nicole. I could tell she was really embarrassed as her face was
reddening. She quietly packed her stuff.

Just as well, I thought. It was the last period anyway. I packed my own
things and walked out. Nicole followed behind me.

I made my way to see the Discipline Master, some short, middle-aged Chinese
guy who thought that his moustache made him look fierce, when it actually
made him look stupid.

Nicole was still behind me. I turned around. I snapped at her.

Me: Why are you following me?

She stopped.

N: Sorry.

She was shocked and a tear rolled down the corner of her eye. Suddenly I
felt bad. I reached out and tried to wipe the tear off. She moved back and
slapped my hand away.

N: Don’t touch me!

Me: Sorry.

I turned around and continued on my way to the office, leaving Nicole there.

Apparently my GP tutor had SMSed the DM about me and he was waiting in his
office.

DM: So what do you have to say for yourself?

Me: Nothing? But leave Nicole out of this, she was just trying to wake me
up.

DM: I will not tolerate rudeness in this college, especially to a teacher.
Furthermore, your usage of vulgarities is unbecoming.

Me: What ever.

DM: Are you not in the least bit remorseful?

Me: Not really. Only that I caused someone else to get chased out of class
as well.

DM: Do you have anything else to say?

Me: Nope. Even if I did you probably wouldn’t understand.

DM: What’s that supposed to mean?

Me: Forget it. Just do what you have to do.

The DM sighed and shook his head. He took out his ‘yellow slips’, otherwise
known as punishment forms and proceeded to fill it up. Then he handed it to
me to fill up my details.

I expected him to pass me a pen but he did not. So I dug into my bag for
one. Dumb luck caused my pack of cigarettes to fall out and onto his table.

DM: YOU SMOKE??!

Me: Yes. So?

DM: Show me your IC.

I showed him.

DM: You are damn lucky you are legal. Otherwise I’m calling the police.

Me: Go ahead.

DM: Don’t try my patience.

Me: Screw you.

The DM was extremely pissed. He grabbed the form once I was done, scribbled
something else and handed it back to me.

DM: Pass this to the general office and get out of here.

Me: Bye.

I took the piece of paper and looked at it.

Two weeks suspension. Wow.

I grabbed my cigarettes and headed next door to the general office to hand
in my form. After that, I headed towards the main gate.

As I exited the school, I saw Nicole standing there, as though she was
waiting for me.

My attempt at sharing my experiences… (Part 54)

By EnigmaofSorrow

Charmaine appeared to be enjoying the anal penetration, judging by her soft moans, and vice-like grip on the bedsheets. I wondered how she coud take it, considering it was not the usual hole used for penetration. Perhaps it was the pain she took pleasure in. But I could not be sure.

On the other hand, I was going crazy trying not to cum so fast. The tightness and friction was wreaking havoc on my dickhead, and I had to slow down the pace to prevent myself from premature ejaculation.

It did not work.

Barely five minutes of poking her ass, I felt the familiar sensation building up in my balls. Charmaine sensed it too and clenched her rectal muscles. It felt as though a champion bodybuilder was giving me a handjob. I tried to pull out, but was unable to do so, as the first wave of semen erupted from my volcano. I stopped thrusting, but Charmaine did not let me, pushing her ass towards me again and again, thus forcing a second wave. The blood rushed from my head and limbs and into my nether regions. I felt faint and on the verge of collapsing. She was one crazy bitch. I tried to pull out once more rather unsuccessfully. My semi-hard dick flopped around like a fish out of water as I fell out of bed and landed on my ass on the floor. I immediately lay back and tried to catch my breath. Charmaine scrambled out of bed and squatted over my abdomen, the lava from my volcano trickling out of her ass and onto me.

I wanted to protest, but she seemed to be enjoying herself.

An amount definitely more than the scientific amount of 10 cubic centimetres was pooling at my belly button.

Me: What the fuck. You’re sick.

C: Who asked you to cum in my ass?

Me: You didn’t let me withdraw!

C: Too bad.

She lay down beside me on the floor and kissed my forehead.

C: I enjoyed that…

Me: You prefer anal to normal sex?

C: Not really. But it seems like your cock is a little to big for my pussy…

Me: That’s still quite sick…

C: You didn’t like it?

Me: It’s weird. You’ve got strange fetishes. Didn’t it hurt?

C: A little. But I liked the way you pounded my ass.

Me: You like pain?

C: I don’t know…

Me: You BDSM freak.

C: Haha. It’s kinda fun.

Me: What are you going to do next? Tie me up and spank me?

C: I didn’t think of that. But now that you mentioned it…

Charmaine got up and opened her drawer, removing a few scarf-like pieces of cloth and a leather belt.

Me: Oh shit.

I tried to move but I was seemingly paralysed after the recent exertions. She tied one scarf over my eyes and bound my hands over my head with the other.

Me: Charmaine? This isn’t funny…

I struggled to move. She did not make a sound.

Me: Charmaine? What are you up to?

Still no response.

I felt my arms being stretched back as she tried to drag me somewhere. Not knowing any better, I assisted her to drag myself. It was a bad idea and I soon found myself bound to her bedframe.

Me: Fuck! Fuck! FUCK! Charmaine! I don’t want to play this game!!!

She slapped me across the face.

C: Shut up and call me Mistress!

Me: FUCKING HELL! Charmaine! This isn’t fun!

She grabbed my balls and squeezed hard.

C: Apologise slave!

Me: OW! OW! OW! Sorry! I’m sorry!

She grabbed my dick and twisted it.

C: Sorry who?

Me: SORRY MISTRESS!

What in the world did I get myself into?

Me: Charmaine! Stop it!

She did not seem to hear me and continued torturing my cock and balls.

I struggled hard and managed to break free from my hand restraints.

I sat up and grabbed her hands. My cock was a little sore from her
over-enthusiastic twisting.

Charmaine started sobbing.

Me: What’s wrong?

She did not reply.

I got up and headed to the toilet.

C: Don’t go.

Me: You’re mad.

C: Sorry.

She crouched in a corner of the room, hugging her knees to her chest,
sobbing.

I ignored her and proceeded to take a shower. When I was done, Charmaine was
still in her corner.

I tried to make sense of her behaviour.

Me: What’s wrong?

C: I’m sorry.

Me: Sorry for?

C: I didn’t mean to be rough.

Me: Why are you acting like this anyway?

C: I don’t know.

Me: It’s your ex isn’t it?

C: Maybe.

Me: He treated you bad?

C: Sometimes.

Me: How?

C: I don’t want to say.

Me: I know he hit you. But during sex?

C: Stop asking please.

Me: He hit you during sex?

C: Shut up.

Me: Come on. I’m your boyfriend. You can tell me.

Charmaine looked up at me, the only emotion in her eyes was a mix of
sadness, and a burning hatred. She moved towards me and started hitting me,
fists closed, pounding on my chest and shoulders. I grabbed her and pinned
her to the bed.

Me: Stop that.

The tears flowed freely.

C: You like this?!

Me: What?

I released her. She grabbed my hand and swung it against her face. For all
my strength and composure, I did not manage to stop in time. My hand, open
palmed thankfully, struck her across her face. Her cheek turned red, and
blood trickled out of her nose.

Me: What the fuck?

C: Fuck me.

I grabbed tissue from the bedside table and wiped off the blood from her
nose.

Me: Is this what he did?

Charmaine nodded.

Me: And you liked it?

C: No.

Me: Then?

C: Every time we had sex it felt like he was raping me. He didn’t care if I
was turned on or not. He didn’t care if I was wet. All he wanted was to
stick it in. And when it couldn’t go in, he would hit me and force it in.

That was utterly shocking, especially since she was around 15 at that time.

Me: So why did you tie me up?

C: I don’t know.

Me: You enjoyed that?

C: I don’t know.

Me: Were you taking revenge on the male population for what he did?

C: FUCK! I SAID I DON’T KNOW!!!

She started crying again.

Me: Pull yourself together. I’m trying to understand you.

Charmaine looked up at me with tear-stained eyes.

C: You’re won’t leave me right?

Me: I don’t think so.

C: Why?

Me: I don’t think I can handle the abuse.

C: Sorry. It won’t happen again.

Me: You sure? Can we be a normal couple? Have normal sex?

C: Yes.

Me: And if you go into your crazy mode again?

C: I don’t know what came over me…

Me: Can you try to remain sane? For my sake at least.

C: I’ll try.

Me: That’s good.

C: You won’t leave?

Me: I won’t. Now go wash up. It’s time for bed.

She wiped her face with the back of her hand and got up to go to the toilet.
Halfway there, she turned back.

C: Don’t go ok?

Me: I’m still here.

She gave a half-smile and entered the toilet, not shutting the door.

I had unwittingly fell victim to her psycho attack. Maybe me mentioning BDSM
triggered something inside her. It was not something I enjoyed and hoped it
would not happen again.

What Charmaine showed me today was two sides of her. One sweet, demure, and
vulnerable. It was the other side that was freaking me out. She had the
capacity for violence, and had no qualms about inflicting physical pain on
herself and others. I assumed that the faint horizontal scars on her wrists
and forearms were that of self-mutilation, and I hoped that all that was in
the past.

As she showered, my mind was filled with thoughts.

I seriously wondered how long we could last.

My attempt at sharing my experiences… (Part 53)

By EnigmaofSorrow

Me: Charmaine?

I shook her a little more violently. She opened her tear-stained eyes.

C: That hurt a lot.

Me: Sorry. You forced me in.

C: I think there’s internal damage.

Me: Yeah. You’re bleeding.

I stuck my finger in and removed it. It was coated with blood.

Me: It’s quite bad.

C: Maybe it’s my period.

Me: Is it supposed to be here?

C: Not for another week or so…

Me: That’s bad.

C: I don’t know.

Me: Do you want to see a doctor?

C: No.

Me: You sure?

C: Yeah. It’s embarrassing…

Me: Go to KK then? They probably have female doctors there…

C: No need.

Me: Seriously?

C: You haven’t finished yet…

Me: You gotta be kidding. How can I possibly continue when you’re in pain?

C: Just continue…

Me: Er. I think it’s better not to.

C: You scared of a little blood?

Me: It’s not little. I might have torn something inside there…

C: Then do it slowly.

Me: You’re mad.

C: But I love you and want you inside me…

I looked at Charmaine, then at my deflated cock. The blood-stained condom was slipping off so I removed it and tossed it aside.

Me: I can’t. Not hard anymore.

C: Then make it hard…

She sat up and started wanking me. I tried to resist but the little head took control again.

C: Put it in. Slowly…

Me: Wait. Let me get another condom.

C: No need. If it’s my period, I won’t get pregnant.

Me: What if it is?

C: Don’t shoot inside then.

Me: Erm.

C: Come on. Don’t make me wait.

Me: Are you still in pain?

C: A little. But bearable.

Me: Ok.

I positioned my cock at her pussy again and tried hard not to think about the various bodily fluids that were inside. It did not work and I deflated slightly. Semi-hard, I pushed in. Charmaine flinched a little but took it in anyway. It was, warm, wet, and a little sticky. I thrusted a few times. Strangely it felt damn good, even though I could see reddish stuff coating my cock. Charmaine appeared to be enjoying it.

C: I think you’re not supposed to be fully hard when entering. This is nice.

Me: I can’t really feel much. Other than it’s wet and sticky.

C: Can you still cum?

Me: I don’t know. I suppose I could.

C: I want you to cum…

Me: I don’t have to you know. Sex is not only about my pleasure.

C: You already made me squirt. I wanna do the same for you.

Me: You don’t have to.

C: Just fuck me.

I continued thrusting slowly, watching Charmaine’s face for any signs of pain, and if I should stop. Instead, she spread her legs wider to accomodate me. My semi-hard cock became harder as I thrusted, and soon it was almost at full length and girth. Charmaine had a slight pained look on her face but she did not let me stop.

Me: I can’t. Really.

C: Why?

Me: Psychological I think.

C: Want to try the other hole?

Me: Which one?

C: Ass.

Me: You’re kidding right?

C: No.

Me: Your pussy is torn and now you want me to tear your ass as well?

C: I have shat stuff that’s bigger than your cock, I think it can go in.

Me: What the fuck. That’s too much info.

C: Sorry. But should be able to right?

Me: I don’t know. Never tried anal.

C: Oh. I have.

Me: With your ex?

C: Yeah.

Me: But you said I’m bigger?

C: Just try?

Me: You have lube?

C: Not really. Use my pussy juices and blood?

Me: You’re sick. You know that?

C: Don’t guys like this kind of stuff?

Me: What kind of stuff?

C: A girl who will do anything sexually…

Me: Probably. But this is a little too much.

C: Are you going to try or not?

I thought about how Tanya had told me previously that I would enjoy fucking her ass, but I never got to try. Now Charmaine was offering hers. I thought about it for awhile and decided that disgusting or not, I might as well try for the sake of trying.

Drawing on my memory of certain porn scenes, I spat on her asshole and inserted a finger in, trying to expand the hole. Charmaine flinched at first but slowly relaxed her muscles to accomodate my finger.

C: Haha. I think my ex’s cock as as big as your finger…

Me: Very funny.

I spat on it again, and on my cock as well, to ensure that it was sufficiently lubricated.

I positioned at the entrance.

Me: You ready?

C: Just give it to me baby. I want your hard cock in my ass.

Me: Wow, you’re the first girl to talk dirty to me.

C: Do you like it?

Me: I think I’m neutral.

C: Well, put it in then?

I pushed the head into her asshole, she relaxed her muscles and allowed me entry.

Tanya was right. Assholes were extremely tight, and the lack of natural lubrication added friction. The sensation of my first anal fuck was out of this world.

My attempt at sharing my experiences… (Part 52)

By EnigmaofSorrow

Charmaine walked unsteadily to the bed, her juices dripping down her thighs.

C: That was amazing. My legs never felt this weak before.

Me: So did I pass?

C: Yeah. I guess.

Me: Well, it’s your turn now…

C: But I don’t really know how to do it…

By sheer luck or coincidence, Maria Ozawa started giving the guy a blowjob.

Me: Hey! You can watch, learn and practice!

C: Idiot.

But she watched anyway, heading back to the chair to sit down while I stood beside her. She held my cock in her hand, eyes glued to the monitor.

I found it a little strange that I did not get hard watching Maria Ozawa give some Jap dude a blowjob, my dick seemed to be dead. Maybe it was time to cut down on cigarettes.

Charmaine watched in earnest as Maria Ozawa wanked the guy, licked his shaft and balls, before starting to suck him.

C: I don’t think I can. You’re bigger than him…

I looked at the guy onscreen. He was probably 5 inches or so, and Maria Ozawa took his entire shaft into her mouth with ease.

Me: She’s a porn star. You don’t have to follow her exactly…

C: But I want to… Just for you…

How sweet.

Charmaine started wanking my cock and massaging my balls. She ran her tongue along the shaft and around the head just like Maria Ozawa did. She kept licking for quite awhile, as though she was afraid to take it in her mouth. By now, Maria Ozawa was already being pounded by the guy, and my cock had reached its full length and hardness.

Charmaine looked up at me with a slutty look as she wrapped her lips around my dickhead. Inch by inch, she took it in before stopping halfway. She was choking herself.

Me: Er. You don’t have to deepthroat you know…

She coughed.

C: Just trying. Who asked you to be so long?

Me: It’s not that long… It’s just nice I think…

C: Not for me!

That was quite true. Charmaine was, after all, a petite girl, compared to Tanya of course, and my 6.5 inches might have seemed to be a little intimidating. Still, she tried.

Me: Just concetrate on the head…

She did, twirling her tongue around my dickhead while it was still in her mouth. I wondered if she had practiced on those frozen ice lollies, as that was exactly what my dick felt like, except that her mouth was warm. She bobbed her head up and down my cock, taking care not to choke herself again. She was a fast learner. But I was not going to cum anytime soon.

I stopped her and led her to the bed. She lay down and spread her legs.

C: Please be gentle. I’m like a virgin…

I positioned my cock at the entrance of her pussy, rubbing her clit with my dickhead, mixing my pre-cum with her juices. With one swift motion, I inserted about an inch of my cock into her, feeling the extreme tightness of of warm, wet hole. Suddenly she pushed me off.

C: Condom!

Me: Oh yeah…

I found the box of condoms that Charles had left behind. It was a twelve pack of ribbed ones, but only a few were left.

Me: Looks like your brother is quite active himself…

C: Strange, he doesn’t have a girlfriend…

Me: Hmmm.

C: And this is going to hurt I think…

Me: I haven’t even entered…

C: But it’s ribbed…

Me: The box says added pleasure…

C: The box lies…

Me: Right…

I capped myself and repositioned for entry. It certainly helped that Charmaine was still very wet, and my cock slid in easily, and inch of it of course.

Me: Ready?

Charmaine bit her lower lip and nodded. I pushed in another inch, then another. She closed her eyes and bit her lip harder, grabbing the pillow and bedsheets. I was halfway in when she screamed.

C: It hurts!

Me: Sorry…

I withdrew my cock.

Me: I think let’s not…

C: No, it’s ok… I have to get used to you anyway…

Me: How should I do it?

C: I don’t know. Just stick it in.

Me: All of it?

She nodded.

Me: You sure?

C: Just force it in or something. Maybe it will create a new opening.

Me: Are you serious?

I knelt there between her legs, dick half inside her pussy. I felt myself getting soft.

C: The other guys were small. I thought cocks were that size. Yours is different…

Me: I don’t want to hurt you…

C: Just do it. Otherwise we may never have proper sex…

Me: Want to try another position instead?

C: No…

Me: But…

C: Stop whining and stick it in!

She grabbed me and forced the full length of my cock into her. I definitely hit her cervix. Thankfully, I was not fully erect, otherwise there might have been some permanent damage.

Charmaine screamed in pain and tears flowed freely out of her eyes. She stopped grabbing the bedsheet and her hands fell slack by her side. She was breathing heavily. I immediately pulled out and saw blood on the condom. I tapped her shoulder.

Me: Charmaine?

She did not respond.

My attempt at sharing my experiences… (Part 51)

By EnigmaofSorrow

C: Now?

Me: Yes.

C: Could I not? It’s embarrassing…

Me: What’s so embarrassing about pleasuring yourself? I do it daily…

C: It’s different. You’re a guy…

Me: It’s not different. Do you just do it, or do you watch porn while doing it?

C: Er, sometimes I watch porn…

Me: Really? What kind? Show me!

C: What? No!

I headed over to her desktop and turn it on. It took awhile to boot up. Charmaine stood behind me, arms folded.

C: You are a sick, disgusting pervert.

Me: I’m also your boyfriend, who wants you to be pleasured…

C: Erm.

Her computer finally started up and I opened the search function and searched for video files. It took another few minutes to search and display the results. When it was done, I was stunned.

Charmaine had tons of porn, way more than me, and it was neatly categorised into different folders, Asian and Western. Even these folders had sub-folders, such as Jap, Local, Homemade etc.. I opened the Jap porn folder, it too had sub-folders. It was truly amazing. I was tempted to open the Bukake folder but decided against it. What truly disturbed me was the folder labelled Extreme. I opened it and saw some BDSM clips. No wonder she did not really complain much when her ex mistreated her. It seemed like she was into this kind of stuff.

C: What are you looking for?

Me: Stuff I can take. Remind me to bring my hard disk next time…

C: Well, you better have a hard dick when you’re done…

Me: Not funny… Anyway, how come you have so much porn? And it’s in neat folders?

C: I’m curious I guess.

Me: These seem like normal porn. There’s no lesbian or anything.

C: I’m not lesbian.

Me: True, but lesbian porn usually involves pussy eating…

C: Not interested…

I continued to click around.

Me: Holy shit.

C: What?

Me: Erm, nothing.

I closed the folder.

C: What, what?

Me: Didn’t know you had animal porn.

C: Like I said, I’m curious.

Me: Right. So what do you normally watch when you want to masturbate?

C: Normal porn.

Me: Jap or Western?

C: Both. Doesn’t really matter.

I opened her Western porn folder and saw a familiar name.

Me: Haha. You watch Peter North too!

C: Ya, why?

Me: He’s got a lot of cum.

C: Can you do that too?

Me: I don’t think so.

Suddenly she was really excited and sat on my lap. She took over the mouse.

C: I like this one.

She opened a clip with featured Peter North and Cytherea, the squirting one.

Me: Hmm…

C: I can’t squirt. Been trying for a long time.

Me: Keep trying then. I don’t know how to do it either…

She watched the clip intently, watching Peter North get soaked by Cytherea.

Me: Looks like she’s pissing.

C: I read up on the net. Girls can really squirt. But I can’t seem to do it.

Me: Maybe you aren’t a girl…

She squeezed my cock, hard.

C: Idiot!

She closed the clip and went back to the Jap Porn folder, opening a clip with Maria Ozawa.

C: She’s hot.

Me: Yeah.

C: Bet you would do her if you had the chance.

Me: Which normal guy wouldn’t?

C: True.

Me: Anyway, are you gonna masturbate, or are you going to just sit there?

C: Wait. I’m getting wet.

Me: Really? So am I.

C: Idiot.

I carried her off my lap and let her sit on the chair. She propped her legs up and her fingers went to her clit, rubbing it, as Maria Ozawa produced one of her many vibrators and started using it.

Me: You have one?

C: Nope.

I watched as she rubbed herself, eyes fixated on the screen. I went forward, sat in front of her and inserted a finger into her pussy. She gave a soft moan. I finger fucked her for awhile, feeling her extremely tight pussy contract against my finger. I tried to find her g-spot as how Tanya taught me. I hit the spot. Charmaine’s moans became louder, and her clit rubbing got faster. I decided to try my luck.

I brought my face towards her pussy and ran my tongue along her labia. At first she squirmed and seemed to slow down her clit rubbing, but I persisted, using my tongue on her pussy, and licking her fingers, trying to push them away so that I could access her clit.

It worked, and she started caressing her breasts while I flicked at her clit with my tongue, while fingering her g-spot at the same time.

Along with Maria Ozawa, Charmaine’s moans got louder and louder, and she grabbed my head, pressing it to her pussy. I felt her body convulse and squirm in the hard, plastic chair.

C: IT FEELS SO GOOD! I’VE NEVER FELT LIKE THIS BEFORE!

I ignored her and continued with the clit licking and g-spot rubbing.

C: OH MY GAWD!!!!! I FEEL LIKE I’M GONNA PEE!

I slowed down the pace.

C: DON’T STOP! PLEASE!

I quickened the pace.

C: OH FUCK! YESSSSSSS!

I felt a stream of liquid flow out from her pussy and onto my hand. It did not squirt out like in the Cytherea clip. Maybe she was not there yet. I continued.

C: OH FUCK! FUCK! FUCK!!!!!!

Another stream.

C: OOOHHHH! YESSSSSSS!

More liquid flowed out. Then I remembered that Peter North had to withdraw before Cytherea could squirt. I stopped licking her clit, but continued fingering her. Then I removed my fingers and rubbed her clit.

C: OHMYFUCKINGGAWDENIGMA!!!!!!!!!

She squirted. And it landed on my face and chest. I kept rubbing. She squirted again twice more. I continued rubbing.

C: Stop, stop! I can’t take it.

She leaned back and almost fell off the chair as it rocked backwards. I caught her in the nick of time.

Me: Congratulations.

C: Huh?

I tasted the liquid on my face. It did not taste like urine.

Me: I think you just squirted.

My attempt at sharing my experiences… (Part 50)

By EnigmaofSorrow

Me: You left it on the sofa? Someone came back. How?

C: Hope they don’t see it.

We heard footsteps coming up the stairs and sure enough, there was a knock on the door.

Charles: Charmaine. You left the lights downstairs on…

C: I did? Oops.

Charles: You also left your bra on the sofa.

C: Erm.

Charles: I’m hanging it on the door knob.

C: Thanks.

Charles: And if you’re having sex, please use protection…

C: Yes kor.

Charles: You need any? I’ll put it at your door.

Charmaine looked at me. I shook my head to indicate I did not have any.

C: Er. Just put everything there.

Me: Your brother is cool…

C: Idiot.

Charmaine was blushing as she opened the door to retrieve the stuff Charles had left outside. The excitement and arousal from our making out on the sofa had died down. I sat on her bed and she sat down next to me.

Me: That was awkward.

C: Yeah.

Me: So what now?

C: We could start again…

Me: Ok…

C: Or we could just talk…

I stared at her, clad in only her panties.

Me: Right. Your breasts are staring at me.

C: Pervert.

Me: Hey, you’re the one who’s not covering up!

C: But you like it right?

We edged closer to each other again, our noses pressing. I stared into her eyes.

Me: Sometimes I can’t figure you out.

C: Shut up and kiss me.

I lowered her onto the bed and lay by her side, brushing her hair off her forehead. Our lips met again as I planted soft kisses on her. Her hands roamed around my body, and mine on hers. She stopped at my crotch, her small hands invading the frontal slit of my boxers. My semi-erection poked out and she played with it, much like petting a snake. It grew in size gradually. She slid my boxers off.

C: Oh my god.

Me: What?

Charmaine grabbed my dick with both hands, there was a good inch or so left. And I was not even fully hard yet.

C: This is huge.

Me: You’ve got small hands.

C: No, I mean seriously. I don’t think it can fit.

She wanked my cock.

I removed her panties to reveal a neatly trimmed bush, and a love hole that was very wet. I traced the outline of her pussy lips with a finger. She gave a soft moan. I slid one finger in slowly. She was right. She was extremely tight, and her pussy muscles strained against my finger. I withdrew my finger, letting her love juices coat it.

Me: Hey! It’s like mozzerella too!

C: Very funny.

I sucked on my finger, tasting her juices.

C: That’s disgusting!

Me: Not really…

I spread her legs and prepared to eat her out. She clamped them shut, almost choking me.

C: Don’t do that! It’s disgusting!

Me: You mean you’ve never been orally pleasured before?

C: No…

Me: Have you orally pleasured a guy before?

C: Not really… Once maybe? I don’t really know how to…

Now this was getting interesting.

Me: Will you let me eat you pussy?

C: I don’t know…

Me: Wait, you aren’t a virgin right?

C: No…

Me: Didn’t you enjoy sex before?

C: Not really. He put it in and it was over in minutes…

Me: I see…

C: My fingers have given me my only orgasms so far…

Me: That’s really sad…

C: You should be quite good at sex right… Considering the rumours…

Me: Not all of them are true…

C: Damn…

Me: Have some faith in me…

C: So how many times have you had sex?

Me: Erm, once.

C: I’m your second?

Me: Yeah.

C: That’s nice to know…

Me: You were expecting a sex god?

C: Not really. But someone more experienced would be good…

Me: I will make you feel good…

C: You sure? Based on what you just said, I might as well masturbate…

Me: That’s not fair…

C: Well, at least I’ll definitely get an orgasm…

Me: Show me.

My attempt at sharing my experiences… (Part 49)

By EnigmaofSorrow

It was shortly after 8 when we arrived at Charmaine’s house. The Hyundai
Accent was parked inside, while the Honda Civic, her father’s car, was on
the outside.

We entered and was greeted by her parents.

Me: Hi Uncle and Auntie.

I had met her parents before when I was over at her place but we hardly
exchanged more than pleasantries.

Dad: Hello Enigma. Charmaine, didn’t you get the sms Stanley sent you?

Stanley is Charmaine’s third brother.

C: No?

She fished out her phone from her pocket.

C: Opps. Didn’t see it.

Dad: Anyway, we’re driving to Genting for the weekend for a short holiday,
and to celebrate the end of your exams.

C: Oh.

Dad: Go get packed then? Don’t you want to go?

C: Not really. Who’s going?

Dad: Stanley, Simon, your mom and I. She wants to try her luck at the
casino.

C: Is Charles going as well?

Charles is the brother who is my sister’s church friend.

Dad: No, he’s working tomorrow. So are you going or not?

C: Dad, could I not? I don’t want to be stuck with Stanley or Simon. And
Enigma and I had plans…

Dad: Oh. You sure? He can come with us too…

Me: Er. Thanks. But I’m not really into Genting…

Dad: Well, in that case, enjoy yourselves then.

C: You too Dad.

Dad: Stanley! Simon! Ten minutes!

And they carried their bags to the car.

We sat on the sofa and started channel surfing. Starhub really sucked. There
was nothing good on TV on a Friday night.

Soon, Charmaine’s two other brothers left the house as well. I wondered
where Charles was.

We were still channel surfing and somehow landed on a movie channel, either
HBO or STAR Movies, and Species was on. It so happened that it was the scene
where Natasha Henstridge was seducing the guy in the bathtub.

Me: Nice show.

C: You like her boobs right…

Me: No la…

C: How about my boobs?

Me: Of course I like them!

C: They’re small, compared to hers…

She cupped her breasts through her t-shirt.

Me: No, they’re just nice.

I cupped my hands over hers and we started making out. Suddenly we stopped.

Me: Your brother is still around…

C: Yeah.

Me: Too bad…

We continued watching the show.

It was another boring hour or so when Charles came down.

Charles: Oh, hello. Didn’t realise that you were here.

Me: Hi.

C: Kor, where you going?

Charles: I’m going to a pub with my friends. Wanna come? Wait, you’re
underaged. Haha.

Me: Very funny.

C: Kor, means you not driving right?

Charles: Yeah. You need to send your toyboy back home?

C: Wei, don’t tease him la.

Charles: Haha. Ok. It’s still funny. Enjoy yourselves then. No hanky-panky
ah.

C: Yeah, yeah.

And he left.

Me: Hey, guess what.

C: What?

Me: We’re alone…

C: Hmmm. So?

Me: So…

I pushed her hair aside and planted my mouth on hers, she parted her lips
and let her tongue slip in. Our tongues met, and the battle began. I slid my
left hand under her t-shirt and unhooked her bra. I gave her breasts a light
squeeze and tweaked her nipples. She moaned into my mouth.

Remembering that I had yet to venture south, I slid my other hand up her
calves, caressing her thighs. I sneaked a finger into her shorts and traced
the outline of her pussy lips through her panties. She moaned and squirmed
and struggled to remove her shorts. She finally succeeded, leaving her
panties on. I removed her t-shirt and mine, and we continued frenching while
I rubbed her pussy through her panties. She unbuttoned my berms and slid
them off. My erection was poking through the slit in the front of my boxers.

She ran her finger along the length of my shaft and stopped at the head,
feeling the sticky pre-cum that was leaking out of it. It was the first time
she actually touched my cock.

C: Haha. It’s like mozzerella…

She played with the pre-cum, coating my dickhead with it.

Suddenly, we heard the front gate rattling.

C: Oh shit!

Charmaine quickly turned off the TV and grabbed her clothes. I grabbed mine
and we ran up to her room. The sudden re-appearance of her brother had
caused my dick to go soft.

We rushed into her room and she closed the door, locking it behind her.

C: That was close.

Me: Yeah.

Then I realised something.

Me: Where’s your bra?

C: Oh no! I left it on the sofa!

My attempt at sharing my experiences… (Part 48)

By EnigmaofSorrow

I met Charmaine at a coffeeshop near her place for dinner. I cannot explain
why but I got a hardon when I saw her, even though she was dressed normally
in t-shirt and shorts. Maybe it was the anticipation of us having sex later
that night, even though it was going to be tough, especially with her
parents and brothers around.

After dinner, we took a slow walk back to her place.

C: You seem nervous?

Me: Really?

C: Kind of… Are you expecting something tonight?

Me: Not exactly… Since your parents are around and all that.

C: Hmm… But I want to have sex…

My dick started to get hard again.

Me: Seriously?

C: Why not? Exams are over, and I’m pretty much free to do what I want
now…

Me: Sex is taking our relationship to the next level you know?

C: Oh my god… Please don’t tell me you are that old-fashioned… I thought
you aren’t a virgin?

Me: That doesn’t mean I’m sexually active…

C: So you think sex should be left until marriage?

Me: It depends…

C: Well, I don’t see myself marrying you… I want a career first.

Me: Haha. Marriage is far away for me.

C: Truthfully, I think we have reached a physical standstill in our
relationship.

Me: Meaning?

C: We aren’t going anywhere… Come on, you haven’t even touched me below my
breasts!

Me: Er. I like things slow?

C: No wonder you only had one girlfriend…

Me: Hey, that’s unfair. You only had two boyfriends…

C: You do know how to make a girl wet right?

Me: I think so…

C: Well, you made me wet a few times, and did nothing about it. I was so
frustrated…

Me: Erm, how come you’re so horny now?

C: I’m always horny. Most girls are I guess. I just had to put it aside and
concentrate on the things that matter.

Me: Oh. Do you masturbate?

C: Of course? How do you think I destress? Especially after you leave me
wanting more…

Me: So we really could have done it earlier?

C: Yes.

Me: I guess I was afraid.

C: Of?

Me: I didn’t want to spoil anything between us.

C: Haha. You know I like you. And you’re a nice guy. But sometimes you can
be really dense.

Me: Very funny. So you’re saying I should sleep with every girl I go out
with on the first date?

C: No… But after a few dates? Like I said, keep us waiting too long and
we’ll lose interest…

Me: Wow, and you’re still interested?

C: I love your hot body, and they way you kiss me. The way you tease my
nipples with your tongue…

Me: You’re turning me on…

C: I’m getting wet just thinking about it…

Me: This is not good…

C: Why?

M: We might not even get to do it!

C: I guess I’ll have to be quiet then…

Me: Oh wow. Then how will I know if I’m pleasuring you right?

C: Hey… I think you watch too much porn. Not all girls are screamers or
moaners you know?

She grabbed my crotch.

C: Unless you’re as big as they say…

Me: Hey! Don’t make me drag you somewhere and…

C: Oooooo…. Public sex. Kinky….

Me: You’re crazy.

C: Nope, I’m just really really horny and I want you to make me feel good…

I stopped walking and grabbed Charmaine by her shoulders, pulling her
towards me and stuck my tongue into her mouth, forcefully frenching her. She
responded likewise.

C: Stop teasing me please.

Me: We don’t have a place to go! That’s the best I can do…

C: We’ll wait for my parents to go to bed then.

Me: You sure you can wait till then?

I pulled her in for another french kiss, this one lasting slightly longer
than the first. When we parted, she was breathing heavily.

C: Stop that! I want you so bad…

I tried to pull her towards me again but she managed to avoid it. Her cheeks
were slightly flushed.

C: Please don’t. I might just explode.

Me: Surely it can’t be that serious…

Charmaine grabbed my hand and stuck it down her shorts. The front of her
panties were soaked.

Me: Oh my-

C: You see what you do to me?

Me: Erm, there’s a playground nearby right?

C: Haha. I’m not that crazy, there’s still kids around…

Me: Ok. Back to your place then.

C: Yeah. I can wait a few hours…

My attempt at sharing my experiences… (Part 47)

By EnigmaofSorrow

I trawled the internet for cheap hotels to no avail. Most were out of my price range and I needed to be 18 years old to book a room.

I thought about giving up the chance to sleep with Charmaine. I called her and told her the bad news.

Me: Hey… I can’t get a hotel. How?

C: Too bad lor.

Me: You don’t sound disappointed.

C: Should I be?

Me: No…

C: You mean you were with me all this while just so you can have sex with me?

Me: No. It’s not like that…

C: Then?

She sounded really pissed over the phone.

Me: I don’t know. I just thought that maybe we could take our intimacy to the next level.

C: Is sex that important to you?

Me: Well…

C: It’s either a yes or no.

Me: No.

C: Then why you want to have sex?

Me: Er.

She seemed to be having a mood swing.

C: If you said yes, maybe I would want to have sex with you.

Me: Huh. So it was a trick question?

C: Yes. And you failed.

Me: I don’t get it.

C: Look, I like where our relationship is at, and I do want to take it to the next level. But your answers cannot be wishy-washy. You have to tell me what you want, and not what I want to hear.

Me: Wait. Let me understand this. You want me to say I want to have sex with you?

C: Yes.

Me: Won’t it make me seem desperate?

C: It might, but at least it makes me feel wanted. Desired. You know what I mean?

Me: I guess.

C: So what’s your response now?

Me: You and me, in bed, tonight.

C: Where?

Me: I haven’t figured that part out yet.

C: Then do something about it.

Me: Ok. Anyway, why are you doing this?

C: I’m training you.

Me: For?

C: To ask for what you want. You can’t keep a girl guessing you know…

Me: It doesn’t seem right just to ask for sex you know? There should be the right feelings and stuff like that.

C: We’ve been together for what, more than 6 months?

Me: Yeah?

C: Seriously you got me wondering whether you really wanted me or not…

Me: Huh?

C: I would have slept with you early on in the relationship if you asked, and if the conditions were right…

Me: Now you tell me…

C: I’m not a loose girl, but I did like you, a lot…

Me: I didn’t want to spoil things, plus you had your exams…

C: Who knows. The sex might have done me some good…

Me: You’re strange.

C: You too.

Me: So I guess we’ll just be hanging out tonight?

C: Yeah. Come over to my place to chill?

Me: Why not? But won’t your parents mind?

C: Don’t think so. Exams are over. You’re a nice guy. We aren’t doing funny things…

Me: We aren’t?

C: Depends. Haha.

Me: We’ll leave it at that. See you tonight then dear.

C: Bye baby.

I could not wait to see if anything would happen that night.

My attempt at sharing my experiences… (Part 46)

By EnigmaofSorrow

I did not go to school the entire week. No one really cared anyway. Only my Track and Field coach bothered to call me to find out where the fuck I was. But I told him I was involved in an accident and was covered by MC.

Charmaine went to school as usual. She did not talk about it when we met after school, nor did I probe. I guess she could take care of herself. Either that, or Nick had threatened grievious bodily harm on those bastards.

The two weeks flew by in a flash and soon school started again.

We did couple stuff during those two weeks. Dating, movies, meals, coffee, long walks on the beach. Entire weekends were spent together. We were inseparable. And yet we still did not have sex. We hugged and kissed and fondled each other, but the sex demon in me was under control. We had something special going on, and nothing was going to change that.

Back at school, our relationship was kept under wraps, save for a few people such as Nick, Amanda and Jason knowing. Nick did not care if we were together, he just wanted to know when I was going to start training again, as there was a Athletics Meet coming up and he wanted some representatives. Amanda warned me constantly not to break Charmaine’s heart, otherwise she would stick a javeline into where it would hurt. Jason was just glad that I was attached and would stop whining about not having a girlfriend. I bet he was a little peeved though, having lost a Counter-strike buddy for clan matches, not that his clan was that fantastic anyway. My brother Andrew and I took out their entire team of five during an ‘audition’ match to join the clan. And he had yet to take his PSLE.

Charmaine and I carried on like this until her GCE A Levels when we separated briefly so she could concentrate on her exams. I was bored during that period, and hit the gym more often instead of studying.

I also went out with other people, girls included, with Charmaine’s permission of course, so that I would not come across to my classmates as aloof or antisocial or even worse, gay. Something did happen though, between me and another girl, but it happened after Charmaine and I had broken up, But that is another story for another time.

Anyway, after her last paper, Charmaine and I went out as usual.

C: Don’t you have to study?

Me: My exams were over long ago. Don’t worry. How was your Chem paper?

C: Should be good, I think. A little nervous though.

Me: Chill out. It’s finally over. You can start thinking of which Uni you wanna apply to!

C: I hope.

I gave her a hug.

C: Hey! We’re still in school!

Me: So? I wanna let everyone know that this hot babe is my girlfriend!

She blushed and shrugged me off. My GP tutor, Mr. Nathan walked by.

Mr. Nathan: Ahem. Less PDA more study please.

Me: Yes Mr. Nathan! Don’t worry!

Mr. N: Oh I’m not worried about your GP. It’s your other subjects that are a cause for concern. Now’s not the time for BGR.

Me: Er. I’ll keep that in mind Mr. Nathan…

He walked off.

C: See la! So paiseh…

Me: He’s like that la… Haha. So where you wanna go?

C: I don’t know.

Me: You know we haven’t been intimate in awhile…

C: Yeah…

Me: So you wanna go somewhere quiet and you know?

She poked me.

C: Disgusting idiot.

Me: Hey, it’s not as if we haven’t done it before…

C: Not with each other!

Me: So now can try la…

C: Well…

Me: You need to destress…

I sounded very desperate.

C: Um, you gotta get me really drunk…

Me: Not a problem.

C: And we can’t do it at my place or yours…

Me: That’s a problem. Damn.

C: Er. Then how? Too bad…

Me: Crap. I tahan very long already leh. It’s like my body resetted, now I’m a virgin again…

C: Very funny. Like that I was a virgin when I entered JC.

Me: You haven’t had sex for 2 years?

C: Yeah.

Me: Wow.

C: I’m not as horny as you.

Me: Haha. Ok. It’s time to change that.

I whispered in her ears and nibbled her earlobe while doing so, knowing it turned her on.

C: OIIIII! Still in school!

Me: Let’s go somewhere then.

C: Where?

Me: I don’t know.

C: Too bad lor.

Me: Your parents home?

C: Yeah.

Me: I thought they go overseas quite often?

C: Not this month.

Me: How about a hotel?

C: Isn’t it expensive?

Me: I go check it out and let you know.

C: So we meet again tonight?

Me: I guess.

C: Alright then. Call me.

I kissed her goodbye and watched as she let her hair down as she walked out of the school gates.

I had to find a place. Fast.