My Very Timid Sexual Encounters


My first sex encounter

I am an average looking guy with average height and average weight, everything’s average so if I strolled along Orchard Road you will not even take an extra look at me. I was 17 when I first had a sexual encounter (began PCC-ing at the age of 13 though), the girl was my second girlfriend.

It was a hot and humid afternoon after school. We were classmates and we both took up the same ECA at school, in which we spent a few hours having activities during that afternoon. We had been in a relationship for 3 months, and we kept this as out little secrets — i.e. We didn’t let anybody know that we were an item.

Her name’s Germaine, she has big round eyes and a shoulder-length hair that suits her face-shape. She is not particularly beautiful, but definitely a SYT + GND type. She has very sweet voice (that I find it very arousing everytime I talked to her through the phone), and when she sai-nai (撒娇) to me I always cannot tahan.

I suggested to Germaine that we head for my home, which is just 10 mins walk away from school. This is not an uncommon scene as she has been visiting my home for the past month, mainly because of studies and ECA stuffs. She obliged.

In my room, we had no mood to study due to the hot weather (my room has no aircon!) And thus decided to watch some movie together. I still remembered the movie that I played was Titanic (this shows how old I am now, hahahaha).

I switched off the lights and we hugged each other while watching the movie. I wasn’t paying attention though, as I felt extra horny that day. My didi had a hard-on just hugging her. Her hair has this nice scent, and when she lean against me, I can feel her side boobs pressing against my chess. Heck, how am I supposed to concentrate?

She seems to enjoy the movie a lot, not paying attention to my fully erected didi, but I couldn’t hold on any longer. I told her to carry on watching the movie as I needed to use the toilet. I stood up and rushed for the toilet and PCC-ed… And came in no time.

I thought that after unloading my stuff I would be able to control myself better, but hell, I was wrong. After entering the room, I find myself fully aroused by the sight of her lying on my bed, school uniform on (all white! Can see her black bra, which is so so… Seductive?) Instantly my didi marikita again. I had no choice but to join her watching the movie. Afterall, I was the one who started it right?

I had learnt about the birds and bees via the Internet, and has fully understood how sex works (i.e. A guy must enter a girl to call it sexual intercourse), but its all theory (with some help of videos of course, hahaha). And my mind was already filled with all the filthy thoughts — just how am I going to approach Germaine?

I decided to take it slowly, I lay myself beside her and hugged her from the back. She responded with a sweet moan (not lustful moan, just satisfied moan), and gave me a peck on the cheek. After about 5 minutes (I swear I didn’t pay a single attention to the movie, hahaha) I figure it was time, and I started fondling her breasts.

The feeling was heaven, it was my first encounter of female breasts apart from my mom’s when I was still an infant. Her boobs were small but fully developed for a 17 years old. And it made me almost want to explode. Germaine was stunned by my actions, but I can’t say she hadn’t expected this, as she gave me an astonished look, but immediately begin kissing me.

As our lips were locked, we didn’t know what to do. She just laid on my chest, with her head up, and we remained in that position for 2 full minutes. I then tried to slid my tongue through her lips. She shivered, and pushed me away.

G: “What are you trying to do?”

Me: “I am sorry, I just can’t help myself…”

G: “You put your tongue in my mouth for what?”

Me: “This is called frenching… I saw from the movie…”

G: “Its disgusting… I can smell the chicken rice chilli you ate this afternoon!”

Me: “I go brush up right away my dear!”

G: “Hehe… You have an extra toothbrush?”

Germaine joined me in the bathroom, with me brushing up first. She looked at me through the mirror, with a very naughty look.

G: “You are very experienced huh, still know how to french.”

Me: “No la! I swear, I am kissing for the first time, damn gan jiong also.”

G: “Hehe.. Really?”

(She then proceed to give me a hug)

G: “I am giving you my first kiss also oh…”

After I am finished with my washup, I went back to my bed room as Germaine wishes to use the toilet as well. I lay down on the bed and my minds began running wild. What if we had sex later? Where can I find a condom? Or should I do it RAW? Will she get pregnant? What if she gets pregnant? Can we still continue schooling? How to perform abortion? Blah blah blah…

G: “Oi… What are you thinking?”

Me: “Nothing…”

G: “Sure?”

Me: “Ya la… Shall we continue?”

G: “Continue what?”

Me: “…. The movie of course (damn cowardly of me!)”

G: “Hehe… Sure!”

As the movie played on, I can sense that Germaine wasn’t paying much attention anymore. She seems to be waiting for my action (at least that is what I thought), I decided to give it one more try.

Me: “I brushed my teeth le.”

G: “So?”

Me: “Can I continue kissing you?”

G: “You very unromantic leh! Why ask so directly?”

Me: “Uhmm, then how should I do it?”

G: “Ah…. Never mind”

Me: “Oh I know liao, can you please close your eyes?”

She closed her eyes. I held her in my arms tightly and we locked lips again. This time she didn’t struggle. She kept her eyes closed but I can sense that she now have heavier breathing. This time around, she kept her mouth opened slightly as we kissed, and I managed to slid my tongue into her mouth. When our tongues met, she let out a slight moan. This time, a lustful moan.

My didi was already at maximum size and I find it very awkward, needing to hug her while avoiding any direct contact that will expose my embarrassment.

I can still remember the taste of the toothpaste, its Darlie brand some more, as we exchange saliva and tongue-fight mischievously. She is beginning to enjoy it more and more, and now her body is leaning towards me, as we faced each other directly. Her breathing is very heavy now, and I can sense her boobs pressing against my chest, I pushed her away to catch some air.

Me: “That was… Great.”

G: “I had trouble breathing leh…”

Me: “Me too.. Too inexperience I think…”

G: “Carry on…”

She hugged me and we rolled on the bed, this time with her on top of me. Her eyes were now open and she looks horny (I am sure I looked the same also). We carry on frenching for another 15 minutes, this time with better breathing control, and both of us fully enjoyed the kissing. It was when I decided to turn her around and be on top of her.

I laid my hands on her breasts, fully cupping her boobs. (Come to think of it, after so many years, I still don’t know what cup is that). I begin slowly massaging her boobs, with her bra on, the feeling is somewhat awkward. I still remember mumbling to myself then, “This is how you do it? Sure bo!”.

Germaine didn’t struggle, but she seems to be either very sensitive, or very worried about my actions. As her body became very stiff, and didn’t dare to move a little. I laid down and whispered in her ear, “Let me take off your bra…”. She nodded. I begin unbuttoning her school uniform, and her black plain bra appeared before my eyes. I had not played with any bras in my life till then, and I had trouble searching for the hook to take it off. Germaine giggled at my clumsiness.

G: “What are you doing?”

Me: “Wait la… Searching for the hook.”

G: “You don’t know where it is?”

Me: “Never open one before leh…”

G: “Come… Here…”

She guided my hands towards her back, and I felt a metal hook on the back of her bra. She said, “Here, you need to pull it outwards then slid back to take it off…” Piak! And I succeeded at my first attempt to undress a lady!~ As the bra was taken off, she immediately use her hands to cover her breasts. I can see that she is blushing.

I still remember having this stupid conversation…

Me: “You are very beautiful.”

G: “What did you see???”

Me: “Nothing, nothing yet.”

G: “Then…?”

Me: “Nothing.. Now you don’t feel that hot le hor? Not wearing anything.”

Germaine chuckled, she is especially beautiful when she laughs. I felt that the atmosphere has became lighter, not so embarrassed anymore. I begin hugging her. She smiled and closed her eyes, hinting for me to french her. I obliged.

As we frenched for the third time, everything became natural, she will now initiate the tongue contact and even twist her tongue against mine. The temperature of the room is rising at an alarming rate, I pushed away her hands and beginning fondling her breasts, I started by pinching on her nipples.

At first it seemed like she suffered an electricity shock, as she quickly pushed me away and let out a high-pitch scream. It didn’t take me long to figure that she was instead being sensitive, as she quickly apologized.

G: “Sorry dear.. Did I just scared you?”

Me: “Its ok… Does it hurt?”

Germaine shook her head.

Me: “You felt uneasy?”

Germaine remained silent, but shook her head.

Me: “You want some more?”

G: “… But be gentler ok? I can’t take it, it was too intensed.”

We stopped frenching, and this time I started caressing her boobs as a whole. It was till this time when I had a full view of Germaine‘s beautiful assets. She has a pair of medium-sized boobs that fit her body nicely. Her nipples were small (some bros here called that eraser tip right?) And light brown in color. I still remembered my brain buzzing with all the weird tones upon the full view.

I started with my hand fully cupping Germaine‘s breasts, and she responded with a series of soft moans. She had her eyes shut and seemed to be slowly relaxing herself to enjoy the pleasure that I am offering. As I felt her lighten up, I begin to attack the nipples again. This time her reaction is smaller, nevertheless she still let out a loud moan.

G: “Ah… My lord…”

Me: “How are you feeling…?”

G: “Very weird… I have not felt this… This sensation before… I feel like.. Exploding…”

Me: “You feel like cumming?”

G: “Coming…? No… I feel funny downwards… I think… Its wet… And I have an urge to… Explode”

Me: “You’re wet already?”

She blushed even more. I can feel my heart pumping hard and fast. All my blood flowing to my didi.

I didn’t know what to do next, my didi says to bonk her immediately since she is already ready for action. But my conscience says that she is still a virgin, and the bonking process can only take place if I have her consent. And I know that Germaine is a decent girl, she will not allow me to go as far as having intercourse with her at this stage. I decided to take another approach.

I continue to fondle her breasts, and I buried my head into her boobs and began sucking her nipples. This may not be the first time I suck a nipple (remember? We were all babies ), but definitely is the most erotic suck i’ve done. Germaine was surprised by my actions, but it seemed that the sensation was too strong and the pleasure too intense to let her sensibility take over her, she arched her back, pushing her nipples deeper into my mouth. Again she let out a heavy moan.

G: “Ooooohhhh… That was so good, I am… Oh god.. I am feeling very high now..”

Me: “You are feeling horny?”

G: “Uhhhmm…. Yes… I am feeling… VERY horny now…”

Me: “You want me to take a step further?”

G: “You mean… You want to enter me…?”

Me: “Yes, but I will not force you if you are unwilling…”

G: “No… Then don’t enter me…”

Me: (Disappointed) “Okay…”

As I have been rejected, I continued sucking her nipples and fondled with her breasts. Another 5 minutes passed.

G: “Ahh… Not enough…”

Me: “Not enough?”

G: “I need it… I need something..”

Me: “What..?”

G: “The way you stimulate me… Its not sufficient, I need something more…”

I kind of understood her meaning. It is her first sexual encounter, and she will strive for more if she hadn’t been satisfied. I acknowledged that by moving my hands towards her lower body. The moment I reached her skirt, I hesitated.

Me: “Look… I know what you mean… You are not satisfied…”

G: (Nod nod)

Me: “Let me.. Undress your skirt, I promise you, I will not take advantage of you, ok?”

G: (Nods again)

Me: “Ok… Now close your eyes.”

I begin unzipping her skirt, her school uniform’s skirt was zipped from the sideway, I had no problem finding it, and the unzipping process was smooth. I now have full view of her lower body, with her undies on. She was wearing a matching black underwear. Due to its color, I cannot tell if her panties was soaked with her juices. I proceed to remove her panties.

This time she hesitated.

G: “What are you trying to do?”

Me: “I will make you ecstacy later…”

G: “You sure you won’t enter me?”

Me: “I swear.”

G: “Ok…”

She lifted her buttocks so that I can easily strip her, she has very firm butts and the skin was silkily smooth. I was astonished by the sight of it. As I strip her, her legs remained tightly shut, a last defence of dignity (perhaps shyness?). Her body is now fully exposed to me. And I had the privilege to admire the perfect body a young girl has — perky boobs, flat tummy and a pussy that has just reached puberty, some very scarce pubic hairs.

I spread her legs, she struggled but eventually gave in, as I suspect the urge in her to fuck was too high to keep her sensible. I leaned close to observe, as this is the first time I get so close to a girl’s pussy since the day I was born. There were no foul smell, instead I can smell the scent of the shower gel she used. If I didn’t remember wrongly, she used Lux.

My fingers roamed around her tummy before striking south, and I think that she had already given up hope of holding back, as she twisted her body in anticipation. Finally my fingers reached her pubic area, the hair were smooth and soft, like baby’s hair, and I started off by tickling it.

She let out a sheepish grin.

G: “Hey… Its very itchy…”

Me: “Doesn’t it feel good?”

G: “No… It makes me even… Hungrier… Hungrier for more…”

Me: “I know, that’s what it is all about…”

G: “You are teasing me…?”

Me: “The hungrier you get, the better climax you will enjoy later…”

G: “You sure?… But I can’t take it anymore, I want to do something about this… I am so hot… Down there…”

Me: “You want it now?”

(She nodded vigorously)

I let my finger caress her outer vagina delicately, she jerked and moaned so loudly that I fear my neighbours might overheard us. As I brushed pass the outer portion of her pussy, my fingers got sticky, it is till now that I had an idea of how wet she was. Her juices were clearly visible.

I didn’t know I can take it this far without jerking off, but I felt the job was done yet, and thus I continued to attack her pussy. After the first brush, I made sure that she can cope with the sensation and begin caressing her pussy. I have learnt from the AV movies which part to caress and which part not to be too rough. As I stimulate Germaine‘s pussy with a circular motion and a consistent tempo, she begin to let loose of herself and wriggle her body in ecstacy.

My fingers were then soaked with her juices, making out the piak piak piak sound everytime my finger stroke against her pussy wall. Aroused by the sound and sight of this, she sat up and looked at me, eyes filled with desire.

G: “You will… Make me cum right…? (She blushed, its the first time I hear her say something dirty).”

Me: “Not that you beg me (I thought of teasing her..)”

G: “You… Are bad… Please… Will you… Make me cum?”

Me: “Yes my lady, I hope I am able to make you cum.”

I slid a finger into her pussy, it was so wet that it went in without any fuss. She screamed and I pulled out immediately.

Me: “Was it painful?”

G: “NO! But I thought you said you won’t enter me?”

Me: “If I don’t enter you, how am I going to satisfy you?”

G: “What if I lost my virginity?”

Me: “You won’t dear, a finger is only a finger, its not a full blast manhood.”

(I wasn’t sure that time, but I just wanted to get things going)

G: “You sure…?”

Me: “You want or not?”

She nodded.

G: “But… Do it slowly will ya? I did feel a slight pain…”

Me: “Okay…”

I carefully moisten my finger with her juices (its everywhere, on her thigh… On my bed…), and tried to caress her pussy a bit before inserting again. She got high easily, and I hoisted her to watch as I inserted my finger…

Me: “See.. If you watch me do it… You will not feel that scared”

G: “En… Ah….”

Me: “I am slowly inserting it … You saw my finger right, they are so wet…”

G: “En… Slowly… I scared pain…”

Me: “Now… I am caressing your vagina, I am still outside, you feel the pleasure right?”

G: “Yes… But it wasn’t enough…”

Me: “Yes, and now I will insert my index finger into your vagina… Relax…”

G: (Very tensed and stiff)

Me: “See… If you don’t relax, you will feel more painful and less pleasure…”

G: “Okay… I try to relax…”

Germaine lightened up a bit. And I spreaded her leg even further.

G: “No, don’t do that, its very embarassing…”

Me: “No its not, you’re very beautiful my dear… This posture of you is very… Seductive…”

G: “(Smiled) Really, you like to see me do this?”

Me: “Why not? I am damn horny now.. But I promised you not to take advantage of you… Otherwise I already eat you up liao!”

G: “(Gave me a long kiss) I love you… Now… Give me…”

Me: “Okay…”

I slowly inserted my index finger into her pussy, the process was smooth and I doubted that if Germaine was a virgin (I didn’t mind though, virginity means nothing to me), 1/3 of my finger entered her pussy, and she started breathing very heavily.

G: “I felt very tight… You sure you can do this?”

Me: “Of course I can, your pussy hasn’t been entered before right? That is why its so tight!”

G: “Okay…”

I begin to pressed against her vagina wall, and she shivered immediately. Her face was then fully blushed and sweats were rolling down her cute face. It is time she enjoy her climax.

I thrusted my finger further in, she reacted with even heavier moanings. Her eyes were now glued to the amazing scene of my finger fucking her tight little pussy. I can feel her contractions surrounding my finger as her pussy fully buried it. I begin caressing and striking slowly.

G: “Oh no… Stop stop!”

Me: (Stopped) “Why?”

G: “Oh no… Don’t stop!”

Me: (Continues)

G: “Oh… I feel so good, so filled…”

Me: “I am taking this slowly… I will let you explode… You just need to let me know…”

G: “Oh please.. Let me explode now, I am so high…so hot… So desperate….”

Me: “Now?”

G: “Yes, now!!… Please… Now…”

I fingered her even harder, and the piak piak sound of my finger banging against her pussy became so loud that I had to switch the movie back on. Germaine has lost her mind now as she is screaming and yelling nonsense at very high pitch. The scene is finally set for the climax.

I used my left hand to hug her and we begin frenching like hell, my right index finger continues to stroke her even harder, and at a higher speed. Her mouth now filled with my tongue, she was not able to let out any moans, the sound of the moans stuck at her throat was a big turn on to me…

G: “Oh now… I think I am cumming…”

Me: “How you know?”

G: “I don’t know… Don’t stop… Harder… Harder…. HARDER……”

Me: “I love you…”

G: “Ohhhhhhhhhhhhhhhhhhhhhh….”

Her body wriggled in ecstacy and she hugged me so tight that I have had trouble breathing. The whole motion lasted for 20 seconds as she came. Slowly… Her breathing became normal and she let go of me, still panting.

G: “That was… Heaven…”

Me: “How you felt..?”

G: “I don’t know… I just felt like I was at heaven, I can’t control my body, can’t control my mind..”

Me: “You just kind of let everything go?”

G: “Yeah… And suddenly my body exploded…”

We hugged, and as Germaine‘s climax subsided, I helped her to put on her clothes. She has returned to her normal self and insisted on putting on herself.

G: “Close your eyes, don’t peek.”

Me: “Whaaatttt? I’ve seen you whole body.”

G: “Cannot!~~~ Close your eyes!”

Me: “Orh…”

G: “Eh… How do you feel now?”

Me: “Me? What feel?”

G: “You said you were very horny just now… How is it now?”

Me: “Still horny…”

G: “Sorry… I don’t think its a good age to have sex now…”

Me: “I understand…”

G: “Why not…”

Me: “You want to help me unload?”

G: “Why not you go toilet and let go?”

*Chehhh…. Disappointed again…*

It was then I decided it was time to send Germaine back home. I walked her back her home, and we parted by frenching in the lift again. Alas, my first sex encounter was sexless on my end, but it did opened up the door for future actions… Which will be posted later

The second try

Just 3 days after our first sexual encounter, Germaine and I decided to spend our weekend at home to further explore our bodies. This time, we decided to meet at her place, her parent will usually visit her grandparent during the weekends, and it is a perfect time (as she was the only daughter, thus nobody will be at home) for us to have some fun.

We started the day with some windows shopping at the nearby shopping centre where we live (in the west, a very big one). We had some light snacks and the conversation popped out naturally.

Me: “When can we go back to your home?”

G: “You very eager hor…?” (Teasing tone)

Me: “Nothing much to do here also mar…”

G: “Wait la… Must be after 2.. Dad and mum will leave for my grandparent’s place around that time…”

Me: “Which is… 30 minutes later?” (Delighted)

G: “Hehe.. Ya”

One thing I noticed about Germaine is that she seems bolder and more direct when it comes to some of the more intimate topics, now that she and I had the first intimate contact. It seemed like a new world to her, and she is very curious about almost everything. She understands the birds and bees, but couldn’t imagine her body’s reaction and all the reasons behind getting wet, horny and orgasming. I took some time to explain to her… In which that I might not sound like an expert, but at least I had the basic ideas all from the porn sites that I frequently visited (not sure about SBF that time… Think not yet founded ba?).

At first she seemed disgusted about herself, she felt that the way she reacted towards my actions were very bad (she used the term ‘Whore’). But after some explanations to her that sexual responses were perfectly normal and instinctive, she appeared to accept the theory (whew!! I felt like luring a little cat into my demon hand, hahahaha) and is more opened to further discussions and explorations.

We continued sitting in Long John Silver and were engaged in a conversation that covered almost every available topics. For my part I thought the time went by DAMN slowly, I had to refrain myself from watching the time on my watch almost every minute… After all, I have been waiting for this chance for… Say, the past 3 days?

Me: “I see, it is about time.”

G: “Now?”

Me: “Yes, by the time we reach your place, just nice your parent has left ma.”

G: “Ok, lets go then~”

We stood up, and as I turned to lift my leg, Germaine raised her hand and gave me a hug. I can feel her chest pressing against my hand. It was definitely deliberate. She grinned naughtily.

Me: “Hey… Don’t seduce me in the public leh…”

G: “You don’t like?”

Me: “I scared I cannot tahan only…”

G: “Hehehehe…”

Germaine looks stunningly beautiful today, she wore a little black dress that was low enough to show off her assets (not that she has something BIG to show off, but it was nevertheless… Very alluring). The cutting of the dress was so fitting that her perfect curves were a constant distraction to me. As I have always thought, why and how on earth did I manage to get to have a gf that perfect? (Later only I know… This is what people called ‘Love is in the eyes of the beholder’, kekekeke)

I held her hand and we left the outlet and headed for her home. Her home is just across the street of the shopping center (Ok ok… Jurong Point it is ). And by the time we reached her place, her parent has apparently left. Perfecto.

This is not the first time I visit Germaine‘s room. I have been here a couple of times, with her parent around of course. We didn’t do anything intimate that time, we were good students and most of our time spent, apart from playing and chatting, was studying.

Her room was not the typical girlish (or pinkish, or whatever you call it) room. According to her, she dislikes pink and prefer blue (weird for a girl right… But I am ok with that). Apart from the bed, which is a queen-sized bed with a Garfield stuffed toy on it, the room is filled with book shelves and a very cleanly tidied study table. The wardrobe is situated beside the bed, and there is a big mirror attached to it.

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1 Response

  1. Niverty says:

    Only didnt like the 3some parts and you letting her have sex with another man.she could juz cheat on weird.hahahxx.

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