Her First(s)

Hmm.. this entry sure did bring back some memories. Maybe bad, but still, memories of my ex-girlfriend, Peiling.

Peiling and I use to play at Block 1 along Thomson Road, opposite Thomson Medical Centre. It was about 4pm if I remembered correctly. For that area, 4pm is pretty quiet. But bright enough to be spotted from the hospital.

To many, I think you would think it’s quite boring and childish. But well, that was what happened for a start.

Because of her conservative and innocent mind, I would respect her as much as I could, while slowly showing her the fun side of pleasure. I would try as much  to wear bermudas of thin materials. We would meet at that spot to have fun, usually after dinner at Novena. She would be in her white ITE uniform most of the times (standard skirt length, she’s not into super short ones).

In the beginning, I would push her against the wall while kissing her in every way and hands massaging her breasts outside her uniform, trying to get her horny. She is a girl who doesn’t masturbate, doesn’t watch porn, very innocent and pure – until she met me. Her moans and hugging would get tighter as I tempted her with pleasure . As I get hornier, my bulge would be very obvious. It was mine (dick) whom she felt  for the first time. Though it was just outside my shorts on my bulge for this part, the previous sentence would apply in the later parts.

I guided her hands to move up and down my shorts to keep me hard. Then, I will push my bulge around her pussy area through her skirt and and move rhythmically to masturbate her and myself. It would be a treat to her when I occasionally moved randomly and violently. She loved it, she felt good but she didn’t know anything then. She just knew she had to continue making me hard so I could pleasure her. The only way I remembered to get off was for her to masturbate me through my undies, and she would hold tissues in front of my dick as I unloaded, without her touching my dick at all.

I remembered there was once she overdid it unknowingly and made me cum in my underwear. It was quite epic as I struggled to clean it.

Soon, it was time to use the vibrator I bought a few years ago from Japan. It was clear in my head. We sat at the stairs and she was convinced by me to try the ‘scary’ vibrating device on her pussy through her skirt. She began liking it and soon, the vibrator was part of of the play we had.

I couldn’t go further than her skirt until much later, she wanted to feel more from the vibrator. My hand would disappear under her skirt and the vibrator would make her high from outside her panties. I wasn’t allowed to even see her panties except when she was too high to care, I would catch a glimpse. That was quite about all she wanted. We could spend two full hours, making each other horny and all sweaty, before letting me shoot.

After a couple of months of playing at Block 1, I asked her for a handjob. She didn’t know how to go about it, and was very unwilling. For her first attempt, I bought an extra thick Durex condom and capped so she would not be too scared to touch it. She gave in and did as I said and made me cum after struggling to keep her tired hands moving. To think we took turns jerking ME off. Lol.

After a few handjobs with condoms, she decided not to waste anymore money and would give me a handjob without condoms. I remember sitting in front on the steps in front, back facing her, and opened my pants (along with undies) for her hand to enter. She didn’t want to see it, but she trusted me and touched it. . From then, she got used to using her hands and handjob became part of our usual play. Most of the sessions, she would sit between my legs a step lower from me, and I would use the vibrator on her while she jerked me off.

I was sure we had fun. I would cum on her hands and we would skip to the kopitiam nearby to clean up – hand in hand.

Finally, it’s time for the blowjob. It was unforgettable. We were making out at the middle part of the stairs, like 2.5 flight of stairs or somewhere. My hand was under her grey denim skirt, rubbing her wet panties, while her hand was in my shorts, getting me off. As I got very very hard from her random speed and movements, I asked if she wanted to try using her mouth and being in a ‘high’ mood, she knelt down and took my dickhead into her mouth, she wouldn’t try taking more of it into her mouth, but was more than sufficient for me.

She didn’t like the taste, but I think she continued because of my ecstatic facial expression. All I knew was my head was spinning and being bombarded with pleasure and numbness. I remembered my eyes were on her all the time, letting her know I was enjoying it.

Although she didn’t suck for long, I enjoyed it and felt especially good after we cummed together. We sort of upgraded from Block 1 after a few months, to her place, my place and hotels. And I’ve even got a powerful pink bullet vibrator for her.

The phrase I remember her telling me is still very loud and clear in my head, ‘我每次想起你的时候都觉得horny,会想要玩。’ I guess she was effectively destroyed at this stage.

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