The Tight-Bodied Tuition Teacher
My first ever attempt posting events (Albeit dramatized and sensationalized.) with my tutor a few years back. Hope everyone has fun reading. Here goes…
The long, re-bonded hair tied up ever so neatly in a ponytail, facial features so sharp she could easily be mistaken as a Eurasian; she was seated right in front of me in a knee-length floral dress with her legs tightly crossed. I cannot help but ogle at that sight of perfection. That, is my younger brother’s tuition teacher, who just a few years ago, was my Maths tutor as well. Seated on the couch pretending to read a book, I take occasional glances at her, with a look of total concentration tutoring my brother. It got me reminiscing, back to the days when I was still an impressionable teenager, she was my tutor, and the crazy things I did.
I was in a prestigious secondary school, but my grades started slipping in the most crucial year, my ‘O’ Level year. Due to the intense competition, my mum (Typical kiasu Singaporean.) took the liberty to employ a tutor without my knowledge to prevent my results, especially the Maths subject, from spiraling out of control. I was livid at that point because with a tutor, it meant more work for me, and I wasn’t a very hardworking student to begin with. All I was told was that her name was Cheryl and I was to expect her that day.
The doorbell rang, I knew it had to be Cheryl and was not looking forward to go through 2 hours of tormenting equations and shit. It all changed when I stood at the door to welcome my new tutor, Cheryl. She looked barely in her twenties, which I later found out she was actually a fresh University undergrad. Clad in a blue denim dress which looked just like the picture, it accentuated her svelte figure. Her hair cascaded just beyond where her boobs were, barely shielding her lady lumps. What caught my attention at that moment was in fact her never-ending legs, presented in clear view without obstruction due to the length of, or lack thereof, her dress.
A saccharine voice abruptly broke me out of my trance. “Hi, I am Cheryl, your tutor. But you can also call me Miss Koh if you like.” She reached out her right hand as she spoke. I gingerly reciprocated her gesture with a firm handshake. I pointed her in the direction of my room and walked behind her as I watched her sashay her way to my study table, my eyes unable to deviate from her smooth, sexy legs. I proceeded to close the door behind me and sexual fantasies started to cloud my mind as I glanced at my bed just beside the study table. I had half a mind to just push her onto my bed and fuck her brains out, but I knew that was just crazy.
She was taking her materials out for the lesson while I came up with the idea of taking her up-skirt on the pretext of moving the fan closer to our table. So while Cheryl was still bent down, reaching for more items from her handbag on the floor, I shifted the fan just behind her ass with my left hand, and my right was armed with my phone as I sneakily went between her legs and snapped freely before she was done.
The tuition session commenced, and I could barely focus, my gaze fixated on her beautiful face as I was seated adjacent to Cheryl at the table; and my arm was still under the table snapping furiously at her legs, hoping to catch more of what she was wearing beneath that blue denim dress. I excused myself to the toilet after and surfed through the shots that I had taken. She was wearing light blue undies beneath, which turned me on even more as I thought all along that girls who match their underwear with the clothes that they wear are especially hot.
The lesson finished in no time as it felt like it just flew by, I guess the adage ‘time flies when you’re having fun’ is true after all. I bade goodbye to my new pretty and hot tutor, looking forward to my subsequent lessons with her, with my precocious mind already devising a multitude of ideas in getting to see her naked in the near future. I already knew what I could do the next time I see her and was eagerly anticipating for her next appearance.
I had only been having sexual fantasies about Cheryl for months, not daring to do anything extreme for fear of any consequences; but I actually occasionally flirted with her over texts to sort of know where her limits were, simultaneously trying to get to know more about her life. Due to our small age gap (She was 3 years older than me at 19), we could actually sustain conversations without any awkward silences over messages. One thing for sure was that she didn’t reject my flirty banter, which I took as a sign of attraction. That was when I decided to do something crazy in the next tuition lesson.
Cheryl was here again for tuition at my place one day. On this fateful day she was dressed in a white spaghetti strap dress, a day I would never forget. Her silky black hair was tied in a ponytail this time, leaving a side fringe which swept from the left of her forehead to her right ear, partially covering her right eyebrow. Her firm breasts were displayed proudly with the help of a high waist belt tightening her midsection which led me to think she had to be at least a B cupper. A slight hint of cleavage can be seen peeking out of the relatively conservative dress, sadly leaving much to the imagination. The highlights still had to be those legs of hers, slim, toned and fair, looking so smooth and inviting.
I wasted no time in executing my plan. I headed to the kitchen to pour the both of us two glasses of cold water and hurried back into my room. This was when I engineered a trip while close enough to her seated at my study table. A considerable amount of cold water was spilled over her dress, mainly around her chest area. Cheryl let out a shriek and was taken aback, quivering slightly due to her being drenched in cold water. I pretended to be really sorry and apologized profusely, set the cups down and reached for her bra cups instead. I innocuously brushed her chest, which was dripping wet, pretending to help her sweep off any excess water on her dress. She was way too preoccupied to notice that I was actually taking the chance to feel her boobs. Her next words shocked me.
“I need to change, it is all wet! Do you have any clothes that I could borrow?”
I only thought I could only get the cheap thrill of feeling her boobs for 2 seconds before my dream was over. I never expected that to happen. I reached into my wardrobe and handed her an oversized soccer jersey, and deliberately not handing her a pair of shorts despite knowing she was in a dress. Amazingly, she didn’t ask for one either.
Cheryl returned to my room after changing into the jersey I gave her and my, she looked stunningly sexy wearing just an oversized t-shirt. I could tell that she was blushing when walking back to her seat. She then whispered, “This shirt is a little short ah, but no choice my whole dress is already wet”, before placing her dress over the chair to air it dry. While she was turned around placing her dress, the silhouette of her boob could be seen from the side of my jersey. I think the brushing of her breasts along with the fabric of my jersey made her nipples stand tautly.
I subconsciously commented out loud, “You not wearing bra?” She instantly looked down at her chest and covered her heaving bosoms by crossing her arms before playfully exclaiming, “Don’t look la! My dress has padding so I didn’t wear a bra okay!” I could tell from her reaction she was not averse to the teasing so I got more daring. “Then can I touch? Don’t need to cover la,” I smiled at her while replying.
Cheryl went quiet and didn’t move, she just stared blankly at me. I didn’t know what was going through her mind, but I took the silence as consent and reached for her arm and pulled it away without any resistance. I was thinking in my mind ‘ji pai hoh seh liao’, pulled her other arm away while maintaining eye contact with her. At this moment, I saw her bite her lips seductively with one eye closed. I held her hand with my left, my right reached and fondled her left breast. All Cheryl did was let out a soft moan which was enough to get me erected. Me being inexperienced, just caressed her breast and did nothing else for some time and I could tell she was slowly getting tired of it. I then instinctively went for what was protruding most, her nipple. This time, Cheryl let out a sensitive moan as her head arched back, savoring the amateur tuning from my fingers. I got bolder and went for both tits, which elicited a more aggressive response from her.
Suddenly, I felt her pouncing on me from her chair to mine. Next thing I knew, our lips were locked. Cheryl did most of the work in the tongue action, while my hands ‘upgraded’ and slid into her loose top effortlessly to finally feel her bare skin on my hands. I cupped my hands against her boobs and grabbed them really tightly while squeezing them with considerable strength. They were perky and of the right size, each breast just slightly spilling out of my grasp.
I couldn’t hold it any longer, I carried Cheryl which somewhat surprised her, and threw her onto my bed. I then forced myself on top of her and continued kissing her while moving my right hand down south. I then pulled the flap of her panty aside and reached for her love hole. I was not really sure what to do and just forced my middle and fourth finger into her vagina. Cheryl let out a cry and said that it hurt. I was left really disappointed when she next said, “Hmm, maybe next time, okay?” I was hopeful though, as she said it with a wink before pulling her top back down and returned to the table. We had not much work done that session, but this was the lesson that marked the beginning of a two-year affair with my undergrad Math tutor.
I could never forget that day, which was seven years ago, the day I managed to feel my tutor Cheryl up her top and nearly getting to finger her. I was 16 and had never gotten that far with any girl in my life at that time; the fact that I got into an all-boys school made it worse and harder to meet girls.
But Cheryl, she was all that I could ever wish for in a girl, pretty face with flowing hair, athletic fit body with sizeable breasts, and who could tahan those slim long legs. I never would have thought I had a chance with Cheryl, but it had taken months since our first lesson to slowly move from the tutor, to an acquaintance, to a friend whom I could harmlessly flirt with, to a fuck buddy – all of it started with texting (Student plan unlimited sms helped.).
After that lesson which I pretended to trip and wet her dress, I wasn’t sure if Cheryl was going to be so open again the next time we met. I initiated a text, apologizing to her that I had gone way overboard that time. I could recall how the exchange of smses went.
Me: “Really sorry, Miss Koh, I know I shouldn’t have done that just now.”
Cheryl: “Nvm la (: and call me Cheryl, I am not that old haha!”
Me: “I have to confess that it was fun though. 😡 Hahaha.”
Cheryl: “Hmmmm yea I guess? It was good till it hurts lol. :\”
Me: “You promised me, remember? You said maybe next time.”
A reply never followed, which got me worried. I knew that initially I had only wanted to brush her boobs to cop a feel, but after expectations were exceeded and getting so close, I wanted more, just like any hot-blooded teenage boy. I sent another text a few hours later to confirm the next lesson’s timing and got an acknowledgement. I then carefully switched topics about miscellaneous stuff, and tried to flirt at every opportunity. I even managed to engage in some sexting soon after which lasted for a few days.
Cheryl was due to come for our scheduled lesson at 4 that day. I was anticipating some progress from getting to her first base last week, so I made a short trip to the 7-Eleven near my place and bought a pack of condoms. I could tell that the cashier attending to me was giving me the look of disdain, maybe due to how young I looked and how young I was; but I couldn’t give two shits about it then, I just wanted to be inside of Cheryl.
I got back just 10 minutes shy of 4, nobody was home, placed the pack of condoms under my pillow and waited. The doorbell rang soon after, I knew Cheryl was here.
There was a spring in my steps as I went to the door to eagerly welcome what’s in store for me that day. I had previously put in a request for Cheryl to specifically wear an outfit which I absolutely love. And true to form, she turned up in a tight-fitting white tank top accompanied with daisy dukes. What a sight and what a major turn on for me that was. I didn’t say much, but only went as far complimenting her by saying “Whoo, nice” before letting her in and giving her a tight hug. I cheekily let my right hand down to her butt and gave it a firm grope, only to be half-heartedly rebuffed with a light smack and pushing away of my arm. It was apparent that Cheryl‘s face was flushed from that gesture. We then adjourned to my room once again and the flirtatious walking of this leggy lass in those tight daisy duke shorts, made all the more enticing with the slight hint of her butt cheeks, instantly got me on a semi hard-on.
On normal occasions, there would be the ten-year series, calculator, foolscap pad, pencil case and random worksheets religiously placed on the table. But not today. I intentionally left the table empty, hoping she would take the hint that I was not in the mood for tuition, but for something else today – continuing where we left off the previous lesson.
Upon seeing the empty table, Cheryl playfully quipped, “Today, no lesson ah?”
I replied mischievously, “Have, but Math is boring, why not we do something else?”
Cheryl: “So what do you suggest?”
Me: “I don’t know, what do you think?”
Cheryl: “We have two hours to spare, quite long ah?”
She said that with a twinkle in her eyes. Without hesitation, I guided her handbag away from her slender shoulders and it glided down her arms as I lay it on the floor. Sit down, I said as I led her to my bedside. Cheryl dutifully obliged and settled on the fringes of my bed, swiftly followed by me sitting next to her. I gently lifted her head by tipping her chin and moved her face toward mine, shyly giving her pecks on her lips. Cheryl, sensing that I was timid in my actions, took the initiative and held the back of my head, pushing me even closer to her and frenched me passionately. I merely went with the flow while she was the one dictating the tempo and rhythm of the kiss. Her tongue was really agile, which got me thinking how sensational it would feel if it were twirling expertly on my raging hard cock instead. I just let myself get carried away kissing Cheryl and soon found myself feeling up her entire upper body incoherently, from her shoulders to arms, breasts and even her tiny waist. What I was doing was akin to a frantic blind man who lost his guiding stick and just using his hands to flap around trying to make sense of the surroundings. That was how inexperienced and nervous I was at that time.
Cheryl then hinted me to focus on her breasts by shifting my roaming hands to her chest, which I gladly reciprocated by fondling with enthusiasm; all this with our lips still locked tightly and tongues intertwined. It was getting hot and heavy, but I was still not making much headway which probably got Cheryl a little frustrated. She proceeded to remove her tank top which was so tight that it brought her boobs up slightly only for them to fall back down and jiggle sensuously, supported by a lacy black bra that was struggling to contain her huge knockers.
“I can’t be doing everything you know? Don’t expect me to be your tutor in this too, okay?” Cheryl mentioned, with a tinge of dissatisfaction.
I knew I had to up my game or risk missing out. I just had to follow what I watched from porn and replicate it in my first ‘Hands-on’ session. I thought to myself ‘mai tu liao’ (Don’t wait any longer.), and reached behind her back and attempted to unclip her bra. Took me quite a while, but it was a considerable achievement for a first-timer. What greeted me next left me cooing with a barely audible “Wow”. A set of perfect twin peaks unfolded the moment her bra fell off her shoulders. That glorious pair of tits were round, full yet perky and milky white, with nipples that were soft, pink and fully erected. What truly caught my attention, though, was a tiny mole she had right above her left boob, which was cute as a button. I did not give Cheryl a chance to continue kissing me as my mouth went straight for her boobs after marveling at such a sight.
I knew that Cheryl was now more pleased with my spontaneity, evidenced by her soft giggles and the leaning of her chest closer to my face. I squeezed both her tits together and licked her cleavage which seemed to excite her as she pulled at my hair lightly. I then alternated the sucking of both her pink nipples, ensuring they both remain erect. Cheryl was by now far more responsive to my actions as her unbridled moaning grew louder. She was enjoying it as much as I did when I saw her increasingly arch her back as I sucked on her nipples harder. Her hands were now wrapped tightly around my back and I could feel her fingernails digging into my flesh through my shirt but it was the sort of pain-pleasure that I would gladly receive as a ‘reward’ for arousing her.
I abruptly stopped what I was doing and pushed her down onto my bed, lifted her legs and placed them on the bed as well to make sure she’s fully lain, defenseless and vulnerable. I pinned her arms down by grabbing her wrists, placing them above her head as I started from her forehead and kissed slowly all the way down to her belly button. I moved back up and frenched her once again while releasing my grip on her wrists, caressing her breasts while my other hand made its way down to her daisy duke shorts and fumbled with the button.
“Are you ready, Cheryl babe?” I asked. No words were spoken and she just responded with a slight nod.
I had less trouble undoing her shorts button compared to her bra. The zip was next and I can feel my pulse rate rising as I unzipped Cheryl‘s shorts. As expected, what was unveiled was a pair of lacy black panties, of the exact design as her bra. I was very tempted to just rip the underwear off her crotch and force myself into her. I had been keeping this fetish of mine to myself since I became aware of sex, and I was not ready to let Cheryl know that I get extremely turned on when watching rape being role-played in porn. I did not know if she was receptive to the idea and so did not want to scare her. By now, Cheryl was doing her own version of a striptease, removing her shorts by sexily gyrating her hips to facilitate the pulling down of her shorts. She was now only wearing that lacy black panties and nothing else, while I was still fully clothed.
“So are you gonna be like this all the way? Only I get to be naked?” Cheryl was stifling a giggle as she pointed at my shorts which could no longer hide my full-blown erection.
“Oh, no la, ok, I take off now,” I stammered as my t-shirt and shorts came off in an instant, leaving only my boxers on. I then wasted no time to get back on top of Cheryl, who was still lying down comfortably on my bed. I continued to passionately kiss her while rubbing her vagina with her underwear still on. She let out soft moans and even twisted her hips to accommodate the tempo of my rubbing of her crotch. I then lowered to kiss her neck, followed by her protruding collarbones, a feature in a girl that never fails to arouse me as well. I loved seeing girls wearing tank tops or spaghetti tops that reveal their collarbones, not too skinny and not too fleshy, perfect that way. I could tell that she was totally at my mercy now. Cheryl was taking it all in with her eyes wide shut, sensually biting her lips and letting out moans intermittently. While moving all the way down south to her pussy, I noticed that I inadvertently gave Cheryl a love bite at her collarbone region, just above her cute tiny mole on her left breast. This is how I am going to remember you, I thought to myself as I looked once more at her distinctive yet subtle mole on her perfectly sized tits.
I found her underwear a hindrance now and slid it down her silky long legs with ease, throwing it on the floor close to where all her clothes lay. The girl whom I constantly fantasize about since my first meeting with her was now totally naked on my bed, finally. I took this moment to savor such a splendid sight, ensuring that this image would never be forgotten. It was now time for some action. I went down on Cheryl and placed my lips on her vagina lips, licking at the flap of her pussy in a circular motion. My thumb was also vigorously vibrating at her clit to give her the maximum pleasure. Cheryl‘s moans began to crescendo, her sex sounds filling my room.
“Oh Ethan, don’t… stop…” Cheryl cried aloud as her hands reached back and grabbed the sides of the pillow. I complied with her request and even increased the frequency of her clit rubbing. I stuck my tongue out and reached as far into her pussy as possible, curling my tongue inside of her walls, feeling the warmth and tasting the juices that flowed from her wet vagina. Cheryl seemed not to be able to hold it much longer as her eyelids were furiously fluttering with every slurp I make in her pussy. All of a sudden she grabbed and tugged at my hair before letting out an orgasmic sigh, “I am cumming… Ahhhhhhh!” By then, Cheryl‘s body was shaking uncontrollably with her eyelids still fluttering. I ceased my tongue action and stuck my middle finger into her pussy, with my thumb still firmly at her already swollen clitoris. She once again reached towards the pillow at the back of her head and grabbed onto them as I did some hooking motion inside of her vagina. My finger started to tire and I slowed down with the fingering. That was when Cheryl felt something under the pillow and pulled it out.
She found my pack of condoms.
Cheryl looked at me slyly with a smirk on her face. “You’re well prepared huh,” she commented. I did not reply and only forced an embarrassed laugh.
“We don’t need to use this today, not yet at least. Be patient alright Ethan? Not too fast, just relax,” as Cheryl spoke with such a seductive tone.
She placed the box of condoms by the bedside and shifted herself to be on all fours, before slowly crawling to me and taking off my boxers to free my raging hard cock.
“It’s MY turn now,” Cheryl said, as she displayed a come-hither look by playfully licked her lips.
Still on all fours, Cheryl brought herself up to a kneeling posture and wrapped her dainty hand around my cock, only managing to cover around half the length of my shaft. “It’s big,” commented the surprised Cheryl. I was overwhelmed with a sense of pride. I felt a tingling sensation when she first touched my penis, pre-cum then seeped out at the tip of my dick. She proceeded to use both her hands to fully engulf my dick in her tiny palms. Cheryl started to pull her hands back and forth jerking my intense hard-on forcefully. I was feeling sky high at that moment; it felt heavenly. The sight of my hot and beautiful tutor wanking my penis never would have happened in my wildest imagination, but it was now a reality.
As much as it felt good, I was hoping for something more than just her using her hands to do the job. Yes, it was true that I was impatient, I was dying to try out how sex felt like. “I wanna fuck you Cheryl,” I plucked up enough courage to signal my intentions. “We’ll see,” was her reply. I was too horny at that time and did not want to just settle for a hand job.
I had to take control.
I stood up, got off the bed and positioned myself as close to the bed as possible. I got Cheryl to face me while she was still kneeling on the bed. “Blow me,” I answered curtly. Cheryl seemed to be aroused by my command and was turned on by my attempt to assert some authority. She placed her mouth close to my penis and teasingly licked off my pre-cum. God, it felt shiok. I took hold of her head by the sides and pushed it towards my dick with her mouth agape. Cheryl stopped short of swallowing my entire length by grabbing my hips as it was clear she was about to choke. Looking at her so vulnerable caused my penis to throb in her mouth; it could not get any harder than that. It felt like I was making her do something against her will, which gave me the thrill I gain when watching role-playing rape pornographic films. Even so, I did not want Cheryl to feel too much of a discomfort. This time I slowly thrust my dick into her mouth while keeping her head still. She seemed to be getting a hang of it as I could now push almost the whole of my tool into her mouth. I experimented further and tried shoving my entire length deep into her throat.
Cheryl had the whole of my penis in her mouth without a gag reflex. After gradually introducing my dick in her mouth, she was now able to deep throat me in such a professional manner. I stood still as I pushed Cheryl‘s head as low as possible, forcing my dick as deep into her mouth as possible. The feeling was ecstatic. Cheryl was now doing a blowjob with adequate suction like a pro, without hands. I freed my hands from her head as she was now in auto-pilot mode, and reached to fondle her perky tits, filling each of my hands with her sizeable mammaries. The look that Cheryl gave me while blowing my cock was so memorable; the pleading eyes perpetually fixated upon mine.