First Strokes

I remember I was ten when my parents signed me up for swimming lessons at my condo. Seeing that the coaching was done by a female instructor, they felt safe despite the late training hours. I enjoyed being in the water, but would be in danger if I did not know the basics. So, the first lesson commenced on a Wednesday evening, starting from the baby pool.

When I was ten, I did not know anything about masturbation except that it felt good when I pulled my blanket against my penis, the pleasure of ejaculation was quite foreign to me then. Jolin appeared in a purple translucent type of top, with a pair of white bikini top underneath. For someone like me who had not really found how to admire women, she was pretty. She placed her belongings on a tanning chair and she stripped her top and sexily wriggled out of her short dark blue denim shorts.

My mum came up to her and handed her a white envelop which she pulled open the unsealed cover to take a peek before keeping it in her bag. My family was not any richer than most, staying in a condo unit provided the safety and amenities like swimming pool and gym, but they did not save on my education, be it academically or on sports.

Jolin rinsed her body and the water flowed down her body, which I had no other words to describe in except ‘flowing’. She introduced herself and we chatted for a bit, then knowing she was still in poly first year. Poly sounded a big deal back then, and the impression was short of someone being in JC, but slightly wilder and had more freedom.

In the baby pool, she made me hold onto the edge and lifted my tummy up, exposing my back to the cold winds. Followed by dipping my head into the water, I stuck to her instructions to breath out through my nose, repeating for as long as I needed. Well, I had no idea what she was doing then, bearing in mind that she’s my teacher.

Jolin: ‘Keep your butt raised, body straight. See? Your buttock is sinking again.’

It wasn’t my tummy that had problem, in fact, my body was as straight as I could get it, but I had no way to know what’s wrong with my butt. Suddenly, she stroked her fingers down my back at the spinal area, and I felt the over curvature of my ass. Yes, I got what she was saying. But.. the trail of her fingers did not just showed me how off I was, it made another part of my body ‘straight’ too.

While she frequently placed her hand on my stomach to help me float, she also had been moving her fingers, sort of adjusting her position on my tummy too. My trunks was getting tighter without her knowledge.

Me: ‘Teacher, I have to go to the toilet!’

Jolin: ‘Huh! Go go! Don’t pee into the pool!’

I waded with my neck to the steps and ran off to the bathroom, trying my best to calm down and put my little wiener pointing upwards to my belly button. I then ran back to the pool and got into the water before she saw me. She was texting on her phone until I reached her and she resumed the lesson. I did a few more times of trying to hold my breath underwater and had grasped the idea of it.

Jolin: ‘Let’s go to the shallow part of the big pool.’

Killer sentence. My hard on had not gone down, and it was because of her constant contact with my body. She stepped out of the baby pool and walked ahead, so I quickly followed her, hoping to get into the water before she did. But it wasn’t the case. She turned around once she was two steps away from the ledge (it was a shallow pool, and she was taller too). Her eyes immediately saw the bigger-than-earlier bulge in my trunks and was stunned for a while even though I was already sitting in the water.

Jolin: ‘You want to take a moment to relax first?’

I nodded eagerly. It was so embarrassing, to have my wiener up for whatever reason. She sat down beside me and did not speak a word. The lights then went out as the digital timer showed 10:00. The pool main lights had gone out, but not the lights at the side. So we could still see each other pretty clearly.

Jolin: ‘I got a method to help you umm.. calm down. Follow me.’

We walked to the deeper part and the water reached my chest. A little scary for someone who did not know how to swim, but I had the ledge to support and I learnt how to hold my breath longer too.

She faced me towards the wall and leaned her body against my back. She felt warm, and the bikini top did not help much as I felt her nipples on me. Her hands then reached for my hands and showed me how to execute the ‘freestyle’. I continued swinging my hands forward after she left my wrist and practised. Her hands then held my waist down into the water and slowly dug into the sides of my trunks.

Doing this will help my hard on go soft? I had no idea. I then felt her fingers on my rod and she wasn’t just holding it, her hand was going up and down, draining the blood away from my brain till I was a bit drowsy. The feeling was weird, but good. I placed my head on my folded arms on the ledge and she continued jerking.

Playing the tip of my penis felt the best, but it got intense in a while and I could not breath normally. I was literally breathless from not doing anything. Hot air could be felt on my ears and I pushed myself away from the ledge before turning over.

Me: ‘Teacher, you okay?’

Jolin: ‘Can you do what am I doing now?’

She turned around and held onto the ledge, while I went behind her and slipped my hands into the front part of her bottom. I could not feel any hair and since she had no dick like me, how was I suppose to do what she did to me? Her legs opened and it was just her crossed arms hanging her body in the water. I reached deeper to her pussy and fondled around, still untrained in whichever sensitive areas of a woman. A few minutes into exploring the folds of her pussy, I hit a spot and her head fell onto her arms, breathing quicker and feeling warmer.

Jolin: ‘You can put your fingers inside.’

Huh? Inside where? Wouldn’t it hurt to have something go into your pee hole? I did not ask her, but pushed my fingers lower and found a really small opening. ‘Here?’ I asked. She nodded subtly and I went right in, digging at the same time to make space for two fingers and then continued wriggling.

Jolin: ‘Move your fingers in and out.’

I nodded this time, and followed her directions. Although my fingers were short, I moved as quickly as I could and felt a sudden squeeze from her insides, and a smooth slimy liquid coated my fingers. It made me move easier and I just continued fingering her, until she squeezed a second time and just pulled my hand away.

She turned towards me and I saw her blushing face, and the same breathlessness that I felt. She gave a weak smile and walked to the deeper part of the pool, stopping at the vertical steps. That spot was the darkest corner and I sat at the top most step, which still hid most of my waist. She pulled my trunks lower and her hands stroke me again, this time, I felt even more excited as I could watch her breasts closer and even make out her bottoms which was lowered to her thighs.

My teacher then took a breath and went into the water, sucking my dick and going up and down, sending a cold shiver up my spine. It was the best feeling I ever had, even better than her hands. She went down on me for a few short moments and finally gave up. Using her hands to jerk me instead. My mind was literally clouded and could not think straight at all.

Jolin: ‘You can last quite long huh?’

Me: ‘Last what?’

She gave me a sly grin and jerked even faster. I was shocked to see my dick grow to a size longer than the width of her palm and so was she, happily surprised. Within a minute or two, I grabbed the railing at the side tightly and felt death. Something was coming for me, something big. She continued the handjob until I felt my dick explode and the force was so strong that the first few shots disturbed the water. Sticky white sperms had took their first swimming lesson too and the load simply got washed into the drains around the pool.

Her hand stopped moving and her head disappeared into the water again, sucking the life out of me. My legs and hands gave way and I fell into the pool, which she caught and carried me to the shallower part.

Jolin: ‘You like it?’

It was my first ejaculation, and it took my ten years of life out. I was took weak to give her an answer. She got out of the pool and helped me up. Before bringing me into the female’s shower room in with her. She soaped me up generously and gave me another round of craziness, this time with a proper blowjob that she took no break in between, until I blew the second load into her mouth.

With her head at my dick and knees on the ground, she opened her mouth and showed me the thick white substance before swallowing it. I guess that was how my favouritism to cum-in-mouth and swallowing started. We washed up promptly after and I returned the favour by fingering her another two orgasms before we were done for the night.

My mum allowed me to go to bed directly, reminding me that swimming could get very tiring. And I sort of understood. Since then, the learning part of the lesson had shortened to 1.5 hours and the last half an hour was an intense exchange of orgasms and climaxes. Crazy? Yes. Impossible? No.

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