It was self-study night and we were allowed back on the school compound for group studies if we so chose.
Cheryl and I planned to study in our usual group that evening, especially with the national exams coming up soon. There wasn’t much time to be spent looking for seats in a fast food restaurant or waiting around aimlessly in the neighbourhood library where every other student from every other school would be vying for the same. Therein laid our greatest incentives to study in school.
Readily accessibility to tutors and friends who were subject experts on the myriad of topics we had to prepare for. We couldn’t be more sold on the idea.
When we had made the decision to study as such the night before, I would have never expected Cheryl to do anything else but study. A straight A’s student, school counsellor, team captain for the school’s swim team, and the one who pretty much organises her cell group’s activities, who would be as straight as her? Who would imagine her to be anything else but?
I couldn’t help but notice the subtle difference in the way her blouse sat on her shoulders, when we met for our usual breakfast routine in school before heading for the day’s assembly to kickstart the day. I couldn’t tell what exactly.
We didn’t have this routine in the beginning. It started out when we were in this year when we were supposed to prepare for our exams, where it somehow seemed that she’d both spontaneously decided to meet earlier in school for breakfast after an incident where she came earlier by chance to see me have my breakfast alone. About a week into the routine then, I realised that by seating myself at a particular corner, she’d seat herself next to me on my right to face the field as we’d have our morning coffee. I had reasons for doing this, one would be to have something other than crowds of students to look, save for the other ladies, the other would be to sneak a daily early peek at her bra between the gaps the placket offered. Sometimes though, I’d be forced to miss the peeking at the peaks because it’d be too risky, or that we’d have another friend joining us that morning, or that I wasn’t lucky enough to catch a glimpse because the placket didn’t simply buckle the other way.
As more time went by, it became a habit that she’d be on the right side of me as if it became part of our routine, breakfast or not. Lo and behold, I also slowly became more acquainted at the time of brassieres she wore – nothing ever too exciting and the occasional sports bra. Not that I never enjoyed the variety, but I loved how some times of the month where her breasts will swell a little and give the view a little more shape than usual. It’d always been wonderful to leave it to the imagination as to what was truly below.
This morning was that one day where I wasn’t lucky because the placket didn’t let me have it my way. I was distracted in a way. I tried to spy for the tell tale signs of the bra straps the moment she turned her back to me, needless to say that didn’t help much. Throughout the rest of the day I couldn’t figure it out nor could I see anything meaningful. However Cheryl was visibly different today. Not just from appearances, but also her behaviour. She was fidgeting a lot throughout the day, crossing her legs repeatedly, leaning forward on her arm tucked under chest against the desk and darting her eyes across the classroom as if she was looking out for something, distracted and unfocused. Even while we had to change our location, she’d hug her textbooks in front of her. This only piqued my curiosity further.
There wasn’t any real way for me to approach the subject. A school friend asking why the female friend had been out of sorts for the whole day – out of the blue.
An hour into our studious activities, I decided to take a short break to digest a few chapters of European History and made my way to the toilet. As usual, Cheryl was seated to my right and I noticed that she looked up at me as I got myself out of the long benches of the canteen and walked along the tables towards the direction the toilet was at. Feeling the buzz of my phone as I turned the corner, I read a message for Cheryl to wait for her at the stairs near the toilet as she wanted to use the toilet as well, but heard that the ground floor toilet was choked thus hoping that I could accompany her to the toilets on the upper floors.
I could understand her hesitation to venture alone as the school wasn’t lit save for the school canteen and the corridors leading to the nearest toilet and the staff room. What puzzled me was that she’d rather ask me for my company than to get Amanda to accompany her instead.
Wiping my hands against the back of my pants as I came out, I found Cheryl leaning with her hands behind her lower back, leaning against the wall smiling cheekily as I approached her. She spun eagerly towards the stairs and walked in front of me. Except for the ambient lights coming from the EXIT signs at the stairwells and whatever dim residual light coming from the HDB flats towering outside the school, it was dark. I couldn’t make out anything in the dark except for the whites of her shoes and her fluttering skirt as we made our way up. I took this opportunity to stare at her butt, swaying as she walked up the stairs – I couldn’t imagine what it would feel like to cop a feel. Lost in her bosom, I didn’t notice Cheryl turning her head slightly as we turned around the stairs, neither did I notice that we’d already past the second floor and were reaching the third.
She stopped us under the EXIT sign and turned around. Then I realised the height difference between us when she tip-toed up closing the physical distance between us, her breathing down my neck as she looked up into my eyes as I squinted under the pale bluish green light of the overhead EXIT sign buzzing away.
“I know you’ve been looking, in the past months since we started having breakfast together.” Cheryl whispered, never breaking her stare as if she was determined to find some semblance of guilt and shame in my eyes.
I was in denial that she might know. “Could you be a little bit more specific? I don’t quite know where this is coming from.”
“You know, some times it’s black, skin tone, if not blue. Amongst other colours.” This gave it away. She knew what I’d been doing, and she smiled when she realised I was stunned.
“Lately, I’ve been finding out ways to de-stress. Exercising’s too much effort, swimming doesn’t cut it any more. I spoke with Amanda about this. She told me that..she masturbates to relieve the pressure. She showed me once, and what in the world have I been missing out on.” Cheryl whispered into my ear and all I could focus on was the intoxicating fragrance of her hair and the exceedingly disturbing confession I heard from her.
I’d be lying if I said I wasn’t turned on by her confession. Cheryl never came across as the type who would experiment. I was still trying to come to terms with her words when I instinctively put my hands on her waist and pulled her in to kiss her. When we broke the kiss then it dawned on me how she looked, bright round eyes, a smile that brightened up the world, and the cutest dimples you’d find. Absolutely the most innocent looking catholic in a ponytail you can find in a school uniform. Definitely a far cry from Amanda.
“Come, the Counsellor’s room is unlocked.” leading me towards the corner where the said room was located.
I’ve long wondered what gorgeous bodies the unflattering school uniforms had underneath. Cheryl’s was kind of an open secret given that she’s on the swim team, so I had an idea of what it might look like bare. But tonight I was going to find out. Just when she grasped the door handle while holding my hand in the other, she snapped towards me.
“I’ve been really, really horny today. I’ve just recently discovered porn and orgasms. Now, I’ve had nothing but images of cocks and fucking in my head for the whole day. All I’ve been really wondering about is how a cock feels at all. This isn’t the way I imagined I’d be losing my virginity, but if it’s you.”
I reached out for the door handle, placed my hand on hers, gently turning the handle to let ourselves in quietly locking the door behind us. We ignored the fact that turning on the air-con then would turn on the the external unit on the first floor, as we made our way by the window where the leather sofa sat beneath. Finally being able to be completely frank with her, “What’re you wearing for your bra today? I couldn’t see it.” as we sat down by the sofa having left our footwear and socks by the door.
She placed her arms on my shoulders, wrapping them behind my neck and looked me wryly in the eyes, “I was hoping you’d ask this today. Why don’t you take a look?”
With trepidation, I unbuttoned her blouse and found myself staring at the skin tone strapless bra as I pushed her blouse to her sides while she quickly withdrew her arms to shyly cover her chest.
“Don’t just stare.”
I understood then gently laid her on her back, kissing her softly and released her ponytail. It was her virgin experience and it wasn’t appropriate to rush, but I’d been having fantasies of fucking Cheryl for the longest time. Oh – what plans I had for her, but the reality of the situation demanded something else. A slow, tantalizing experience for Cheryl to take away before I may have her in the manner I preferred.
I sat myself up, to see her back to covering her breasts as she looked towards the middle of the room. The confidence she had from earlier had all but gone away. In order for me to start playing with her nipples, I had to gently pry open her arms then and undo her bra – conveniently the one she wore was clipped at the front. Cheryl was very turned on by the situation at this point, as I pulled apart her bra to reveal her breasts in the full glory they deserved, I paused for a moment to commit the view to memory.
Cheryl – school team swim lead, arguably one of the smartest students in the school, counsellor, and probably one of the more coveted girls; lying there on a sofa with the top spread wide open with pair of perfect B cup breasts, gently lit by whatever grey ambient light that crept in from the urban jungle.
Her moderately sized nipples appeared black under the lighting and didn’t do justice to what they really were. I eagerly placed my palms around on each of her breasts, feeling the firmness of it as I gently applied pressure through my fingers as if squeezing a balloon. Her eyes were closed and her face was clearly showing anxiety. Strangely, Cheryl wasn’t moaning yet and ironically, haven’t met my raging hard on either.
I then proceeded to pay attention to her nipples. While shifting my weight, Cheryl seemed to understand my intention and widened the gap between her legs slightly, allowing me to put my weight on my left knee as I placed it against her groin. In doing so, I felt something cold just above my knee – she was soaking through her panties. This only got wetter, but warmer when I twirled her right nipple between my fingers and licked the other with my tongue, gradually sucking it while flicking the nipple. She gave her approval and endorsement of her virgin experience of a guy giving physical carnal attention to her breasts by grabbing the back of my neck and moving her hips against my leg repeatedly, though her moans were still repressed.
Finally having enough of her breasts, I left her breasts to unbutton my shirt while she stared at the bulge in my pants.
“It’s not the first time I’ve noticed that. For the past two months, I’ve been coming in the mornings wondering what was under it. Sometimes, I’d deliberately let you sneak at peak under my shirt and see that grow in size a little.” Cheryl sat herself up and pulled her bra from behind, leaving it hanging from the backrest of the seat then turned her focus to my pants.
She placed her hand over the zip as if to gauge the size it, then lowered the zip and undid the button at the top and slowly lowered the flap while pulling down my pants on one side. After I’d thrown my shirt on the table I lowered the other side of the pants she neglected as I saw her still staring down at my crotch. While she stared at my underwear, I stroked her hair to silently hint to her that it’s the the way forward.
You could tell she wasn’t all that experienced. But all that went away when she pulled down my underwear and wrapped her cold fingers around the shaft, her eyes opened wider as if she struck gold. She kicked her hair back and looked back up at me with those eyes in wonderment, smiling as she gripped my cock and stroked it. I could barely make out her dimples in the darkness of it all, not the mention that the sight of her face against the contrasting backdrop of her moving her hands along my cock and her bare breasts hanging loosely not too far below – she definitely wouldn’t let me take a video or even a picture of this scandalous, yet most memorable moment.
Evidently, she was more comfortable now. I gestured her to lay back on the sofa while I dropped my pants onto the floor and lifted her legs into the air to remove her soaked through panties and threw that onto the table next to my shirt. I didn’t bother to take a look at her pussy to take advantage of the moment as she spread her legs, lifting her skirt up onto her flat tummy, and placed my cock in front of her vagina.
Cheryl was unbelievably wet there was obviously no need for foreplay. The realisation didn’t come until I rubbed my the tip along the length of her vagina in an attempt to spread her fluids out before I inserted into her. There was no visible resistance from her except for her concerned expression that reminded me to be gentle with her. When I placed my cock slightly inside of her vagina, she winced out slightly in pain. At that point, I found myself instinctively moving myself forward over her, assuming the missionary position to kiss her while I inched my way slowly into her.
Tight, warm and very wet. Fucking Cheryl was different from the others. There was no compulsion to just fuck her, unlike when it came to fucking Amanda. Instead, greater pleasure was derived from giving her long, slow strokes into her. Her deep breathing and the restrained moans from both pain and pleasure was a great incentive to fuck her harder and faster, but I wanted to savour the moment of taking Cheryl’s virginity away from her.
“It’s painful, but keep going.” Cheryl managed to say this much between the moans after I broke the kiss.
I could feel her getting wetter down below, but I couldn’t tell if it was from the blood that came from the hymen. It wasn’t just feeling her wetness any longer, I could hear it. Each stroke came with the satisfying sound of her moan and the audible slip of my cock thrusting in and out of her. After, she unexpectedly took the initiative and hooked her ankles behind me and gyrated her hips upwards, increasing the tempo slightly, tightening her vagina each time she moved herself up.
Her moans became increasingly laboured but she no longer held back as it resounded across the small room we were in. She then paused for a short moment when she released the unlocked her ankles behind me and dropped herself onto the sofa, shuddering in pleasure as she gripped my back while my unspent cock slipped out.
Standing up while she was still lost in her orgasm, I heard the dull vibration of my phone come on from my pants lying on the floor. Retrieving my phone, I saw Amanda’s name flash across the screen with the green telephone icon to pick up her call.
“Are you two lovebirds done with the toilet yet? You’ve been gone for what. 20, 25 minutes? Isn’t that enough?” Amanda knew exactly what was going on. She probably had a part in this.
Looking at Cheryl still lying there spent, eyes closed and with her uniform crumpled. Admiring her beautiful body lined with layer of sweat reflecting the little light that barely lit the room, “I don’t think it will ever be enough. But we’ll come down after she finishes me.” I hung up the phone and went back to Cheryl.
Her face was filled with a peaceful serenity. She looked satisfied. Taking a picture was too tempting, but the flash would give it away. I decided against it and placed the phone on the armrest of the sofa.
I lifted up her hand and guided it to my still hard cock. She reacted by kneeling on the sofa and removing whatever clothes she had left on her.
“That’s going to leave a stain.” she gestured to the damp patch of her skirt as she started stroking me. Clearly, she was intent on having me finish on her breasts. Then she paused for a moment.
“Wait.” She reached into the pocket of her skirt and removed her phone. After a few quick taps and turning on the torchlight on the phone, she handed it to me. “Take a video of you cumming on me. I want to keep it.”
She was audacious. I’ll give her that, but that also meant I lost the golden opportunity to take other videos.
The phone sounded off a tone signifying that the recording started, I raised the phone higher to capture her face looking up into me as she squinted her eyes against the light and worked on my shaft. What I didn’t expect her to do was to lower her face to my slightly bloodied cock then cover the tip with her mouth, sucking it as she continued to stroke the rest of my rod, looking back up into the camera with her large eyes. That was the sexiest sight of the night and sealed it. She swiftly raised herself back up just before I released my load unto her breasts and continued to look into my eyes. I wasn’t sure if she was a virgin before all this any more with all the mixed signals.
“Was it good? I remembered that from a video Amanda showed me.”
“It was sexy as hell, and it was awesome.” a smile spread across her face as the phone continued the recording. “Okay, time for us to go. We still have studying to do. You good now?”
“Yes. And since our last paper is next Friday, I was wondering if you’d be free in the afternoon? I’ve no interest in going out to town with the rest. There’ll be no one at my place either.”
“Only if you give me the video we just took.”
She pondered this over for a while I handed her some wet wipes I found lying around. “Find out if I’ll give it to you when you’re over at my place.” There’s just no way this girl was letting up, and I’m not going to complain.