My Elder Sister’s Friend
Story submitted by: Wendy
I was a 15 year old, Secondary 3 boy from a decent school. I was quite popular in school as I looked attractive enough, tanned, sporty and handsome. I enjoyed the occasional flirtations with cute girls, but I wanted to remain free from obligations, preferring the internet porn as every time was a different fantasy and it was so easy. What got me off real fast was my personal fetish of slender legs, short skirts – JC girls, especially because they had well developed figures and especially short skirts. I would enjoy jacking off to gals in school uniform and I had a favorite picture of a particular girl. Her legs were a sight.
I have an elder sister, Jaslyn, 18, who was in J2. She also wore the same uniform, from the same school. They could be friends, but I couldn’t ask my sister about it, of course. I tried to look through her Facebook friends, I only can guess, and hopefully I thought, it was Samantha, the hottest looking chick among my sister’s school friends, there were some uncanny similarities like the sharp pony tail, the length of hair and the rather large sling bag that also appeared in her Facebook pictures. She was the latest object of my lust. I could feel my heart racing faster and the light fuzzy feeling of excitement in my chest when I began masturbating knowing I be cumming for her. I would return to this picture just before I reached the point of no return.
However, recently the feeling had begun to wane and I was looking for more excitement. I tried searching for sex stories, f-Friday, sgerotica, Tumblr etc came out and also a Japanese hentai manga website. I spent hours going through the stories, it was very interesting reading stories for the first time, because you never know how the story is gonna go, and any twist that may come up. Boy, there were many genres of erotica, bestiality among the extreme (Not my type at all.). I found the school uniform to be especially appealing, progressively, it linked to the elder sister, incest genres, hypnosis, mind control etc. Countless hours reading these stories and continually cumming. It was great, dizzying excitement and time passed so fast that it was always past 1 am before I noticed the time to sleep for school.
It was a normal Thursday after school, taking the MRT back home from Bishan MRT. A few stops later, as the train reached Lorong Chuan, there I saw Samantha, the girl whom I had spilled many seeds for, right there in the same train cabin as me. The dormant sexual feeling for her began to come back in a rush. She dressed differently today, wearing black sports shoes and a backpack, my dirty mind began thinking about her, her short skirt, slender long legs, as she stood there swaying slightly with the train momentum, facing me, her shoulders resting against the side panel of the reserved seat, using her phone. I was standing at the same panel diagonally across her. Erotic thoughts crossed my mind and made my consciousness hazy. My basic animalistic carnal desire began to rise. Before long, at Tai Seng MRT, she walked towards the door, our eyes met for a moment and she stopped right in front of me. Her sharp pony tail and well defined pretty face was a beautiful sight. I wished for the train to encounter a system fault right now, the train now coming into the station, fast approaching the door which she would exit. She turned and looked at me for the briefest moment before the door opened and she escaped from the train, away from my preying eyes. Trusting a girl’s sixth sense and peripheral vision, I believed she must have felt my attention and intent.
Being the impulsive me, my legs moved forward and followed her, eyes fixed on my fetish, her legs and skirt. I had some distance to catch up and managed to get behind her. We were at one of the last cabins and there were few people alighting at the same stop. My hands instinctively went to the phone in my pocket as with the habit of people nowadays of always checking on their phone. Suddenly it got to me that this was an opportunity for a candid moment. I did not know why, and had never done this before. It was August and I knew she was in J2, there would not be another opportunity. I swiftly turned on my video as we were getting up the escalator, and she was standing with her casual pose of legs slightly apart. She was not using her phone and looking upwards. It was daring and dangerous, my heart racing extremely fast and feeling the vein in my neck throb. I was also having a massive feeling in my pants. I was comprehensive on the first try, being extremely careful not to touch her thighs, then I looked up, she was unmoved. “Fuck this.” I thought, I couldn’t care anything else at that point. Emboldened, I give it another go, this time going long and deep, exposing her black panties which were matching her black shoes. We reached the top very fast, I kept my phone. I knew I had something that is so private and sexual, it would be my fap material for a long time.
As I said, I was an impulsive guy, I followed her on, turning right after exiting the gate, she took a glance to her right towards the gate and continued walking on and going up another escalator again, I already had my shot so I don’t want to risk myself again. I stayed more than a few steps below her. We got off and I continued following her down the few steps of a stairway. She turned around to look at me and we froze there for like 2 seconds.
“Yes? Are you following me?” She asked me suspiciously.
I kept silent before answering her meekly, “Yes. I think you are beautiful.”
“You fucking pervert, following me with your eyes all the way in the MRT and coming out here. Do you live here?” She knew I was staring at her in the train.
“I don’t live here, I also don’t know why I do this… I don’t understand… I am sorry, I will leave right away.” I did not want to bring up my sister and wanted to leave as a stranger in her life.
“You think you can get off like this?” her temper rising.
“I did not do anything at all.” Knowing in the safe knowledge that she would not know about the video
“Taking video of my upskirt is nothing right? So only raping me counts?” she said with a wry smile on a corner of her lips.
I was taken by surprised. Many thoughts came to me at once. I knew she purposely didn’t expose me, and I think I was having a chance right now. She might be interested in hooking up or blackmailing me of sorts. I had to be careful in this dangerous situation.
“Hey, I didn’t do anything like that.” I was trying to deny if she were just making a false allegation based on her guess.
“I saw your phone underneath my skirt and I can see your reflection from the side glass of the escalator. You were so busy that you didn’t notice me. You are a sick bastard.” She continued.
She might have glanced down without moving her head, and girls have excellent peripheral vision to notice something on the corner of their sight.
“Then why didn’t you do anything?” Knowing that I was exposed, I spoke more directly.
She paused. “Because I want to know why you would do that?” Not giving much away about her intentions.
Caution. I did not want to sound like a pervert so she had no choice but to report me.
“Sorry, it is my fetish. I am really sorry, I don’t know what got into me. If you can give me a chance, I will be really grateful.” pleading her with my charismatic eyes.
“If you can give me this chance, I will be thankful. I am truly sorry, and I have never done anything like this before.” I continued as she was unmoved. “I still have my studies and everything, I really regret this already. What can I do for you to let me off?”
“Depends.” that was all she said. Hinting at something that I could provide her.
Thinking hard for a good way to offer her. I thought no words would be the best way.
I removed the left side of my backpack and brought it forward, took out my wallet and gave it to her.
And she smiled. Bingo. Money makes her world go round. She gestured for us to move over to the vacant bus stop, away from any person that might be passing by. She sat down with her knees closed together and her short skirt ride up her thighs, exposing about half the length from her knee up. She tried to flatten the front of her skirt and pulled it down. I glanced at her pair of smooth fair thighs.
“So, how much would a secondary school boy have in the wallet?” I was from a prestigious school and others normally thought of students from my school as well off. I was from a pretty well off family, so they were right in my case. I carried around a $50 note and some $10 in case for any purchase that I might need on the spot. I also carried 2 ATM cards and a sub card so it would be convenient to for me to withdraw cash from different local ATM’s or when I don’t have cash and need credit on the spot.
She saw what I had in my wallet, and I thought she would be satisfied with the cash I had. I thought I saw her eyes widening up as she took out my sub card and other miscellaneous cards – retail membership cards, country club card, etc. I knew this that she was a gold digger there and then. It was just a matter of how much I was willing to afford her.
“That’s all I have, $80 something.” trying to pull a quick one on her. I knew she wouldn’t take it, it was to lighten the mood.
“Ha! Right. You think $80 something is enough for even a shawl from *high-end fashion boutique, name have a number 21 in it*?” This further confirmed her materialism.
“Okay, but how much? I cannot give you everything right?” I got a little uneasy contemplating what she might ask for. I got a hand in my pocket feeling for my phone.
“Pass me the phone first, I want to see the video.”
I passed it over. She looked around as if she was doing something dirty watching her own upskirt video.
“Sicko.” she exclaimed as she watched her own discriminating video.
“Delete it then.” I teased her.
“Not so soon idiot. I want $500.” She demanded and kept my phone.
It was too much for me. I was not willing to give this much just for nothing in the end. I had to think of a proposition so she might consider accepting.
“It’s too much, I have to check my accounts first.” Of course I knew I had more than that, $500 was the minimum sum for each account. And I couldn’t let this opportunity with a pretty JC girl go.
“$500 and I get to keep the video.” I broke into a weak smile, trying to set a boundary with her.
“No, you will delete the video and give me $500 first.”
“I don’t know if I have enough, have to check first.” thinking of which card would have a lower amount.
Lightly reaching around her waist and bring her closer, “Would you be keen if it could be more?” Trying to inject the idea into her mind.
“It depends on what you have in mind, I may not agree to it.” she was coy about the idea, but at least she’s listening.
“Okay, let’s see how much I have left in my account first” knowing she have to see the money first.
I tried to take her hand and she seemed willing at first but she let go of me when we approached the stairs back down to the MRT station’s ATM.
There was only 1 ATM anyway and I checked my account, she tried to get closer, but I told her to stand aside before I would do anything. It was good. $2,153.32 I had a stirring in my pants as I knew I could go further.
So I withdrew the $500 and passed to her. I tapped on her shoulder to bring her closer and whispered in her ear, “What if I give you $300 for a blowjob in the toilet over there?” I purposely lowered my intended amount to have some room for negotiation.
“No way I would do that.” she replied. I was catching it as a vague answer that $300 was not enough.
“Okay, how about this, you can have $500 for it, that is another $500 on top of what you have now. You are running me broke, dear.” sounding desperate to make her agree.
“Alright. Give it to me now.” she relented to the amount.
“Okay, and I get to keep the video right? And your face is not in it anyway.” trying to push further.
“No, you pervert…” she sounded tame as if I had the right to ask for it after giving her that much amount of money.
“Okay girl, anyway, what’s your name?” I asked knowingly, as if I just realized that I didn’t get her name.
“Just call me Sammi.” was all she could think of immediately, something close to her real name.
“Okay Sammi, $300 for keeping the video and that is final.” playing along with her false identity.
“Go on then, pass it to me.” she wanted it enthusiastically.
And so, I was being suckered off because of my lust. I took back my phone after handing over the cash and while she counted the money, I switched on my voice recorder.
“Shall we?” I couldn’t wait.
“Okay (:” So willing that it felt like she was my girl.
We proceeded into the female toilet after she checked out the inside for any person, and took the furthest cubicle from the entrance.
I reached over and kissed her, she embraced me and we hugged like lovers. I took each of her hands and pinned them on the wall, beginning to rough her up. Our tongues met and we french-ed passionately, twirling my tongue with her’s as she was just as willing. The feeling in my pants begun to stir and my dick started to stiffen.
I reached down with one hand to feel her breasts through her beige blouse and tried to open up the buttons. I used both hands soon as it was clumsy trying with one hand, she wore a matching soft black bra, I pulled one of the cups down and lustfully licked her tits, softly biting on the nipple, Samantha trying hard to hold back her muffled moans. I went further south with my right hand, closing in on her pussy through her skirt, Samantha tried to resist with a cute frown on her eyebrows and slight shaking of her head as if I was forbidden to enter, but there was no resistance at all when I forcefully reached directly underneath and deftly shifted her panties aside with my fingers. God, she was soaking wet already. My index finger went inside first, just to test how tight she was. It was a tight and smooth entry, I reckoned one finger would get her off. Alternating between shafting my index finger into her love hole, I randomly stopped abruptly and twirled my index finger, rubbed my thumb on her clit with my tongue adding to the pleasure. She would give off a weak open smile whenever I did that, her eyes closed, enjoying the moments in time.
“Sammi… Ready to cum?” I whispered and smiled.
She nodded once, so swiftly like she was desperate to cum.
I upped my tempo and then slowed down just to tease her one last time. I smiled as I withdrew my finger from her dripping love hole. She looked a bit pensive, a little sad that I did not proceed on faster. This time, I used my middle and ring fingers for maximum girth on her young, tight hole. She let out a controlled squirm as my fingers entered. I went rough and fast, this time not stopping for any shit, pure game. As I started shafting her with my fingers, I grabbed her tits and french-ed her roughly, giving her maximum pleasure on all fronts. To top this up, I increased my speed as she was starting to grab my hair and chest as she was reaching her peak very soon. I gave it my all for her pleasure, shafting in and out with all the strength I had, my forearms were starting to burn. And still I kept on going, increasing the tempo even further, like it will go on increasing faster forever…
I felt the hands gripping more tightly and bringing me closer, and waves of pleasure overcame her as she twitched her whole body. I still kept at it. Her juices began to come out in spurts and waves. I felt like a fucking adult man, ego filled being able to pleasure a girl. Her love hole tightening on my fingers sporadically as the waves of pleasure overcome her. Her slender legs gave way and she knelt down. It was natural that she reached for my pants, taking out my rigid cock so swiftly, I felt the difference in temperature immediately in the cooler toilet than it was in my pants.
“No.” I whispered, as I held each of her hands and brought them palms facing in, to behind her head. I shifted us towards the wall and pinned her hands on the wall, cushioning her head for the impact that I was going to make. Once I knew her hands were right behind her head, safely, I released my hands and grabbed her head and using the other hand to guide my cock. She already knew what I was going to do, she smiled cheekily and let a tongue out, circling around my dickhead and teasing it. I shifted my hips and positioned my cock lower as she opened her mouth to invite me in. I pushed my hip in gently, letting her take the feeling. After a few pumps, I started to rough up and go on fast, both hands on her head that seemed small in size compared to my large and long manhood. Occasionally I pinched her nose and held my cock in, it was amusing seeing her face go red, I knew she would get a light fuzzy experience as she lacked oxygen, it would enhance her feeling. I took long enough for me to feel that I should go faster.
“I will go faster now and cum into your mouth, Samantha.” I grinned as I decided this was an exciting moment to tell her, with her mouth gagged and all.
I thrust my hips faster and violently, knowing that the beans had been spilled and wanting to spill my seeds next, I took her all into the base of my balls, long and hard, but making sure she does not gag and make any loud noise. I wanted to cum so bad now, I went for speed, just 3/4 of my cock in and out of her petite mouth, and the only thing I cared for was cumming. Roughing her blouse and feel her breasts, I greedily tried to feel everything pleasure I could from my position and still pumping into her, mouth-fucking her with strong intent. I took in her head with both my hands, lifted her head away from her hands, and started attacking the top inside her mouth. She was holding onto my hips for support. I began to reach my point of no return as I looked into her eyes, she knew I was edging it. The look of confusion in her eyes was amazing, a come-fuck-me look it was, as I thrust-ed even faster to my peak.
“Fuck!” I couldn’t help it as I felt the intense waves of orgasm through my whole body as I cummed directly inside the top of her mouth. It was the best I ever had. I stood there for a while, holding her head in as she wanted to pull out and I used her mouth again to stroke a few long times before tilting her chin up to prevent her spitting out my semen before popping my cock out of her delicate lips.
I knelt down beside her and whispered, “You are my sister’s friend, Samantha. I knew you from Jaslyn’s Facebook. Now, we had a great time and I do not want you to worry about anything, just swallow my cum. Then it is over.”
Samantha thought about it and hesitated, but she swallowed it anyway, like a good girl, and it boosted my ego knowing that.
“I had my best cum ever.” I told her honestly.
“(: me too…” She said earnestly.
We had the best time together.
I exchanged numbers with her. I had thought about using that voice recording to coerce her into having sex, but I was spent anyway.
Afterwards, I guess it is better to have sex with ‘Love’ and freewill instead of threatening or blackmail. The future is yet undecided.