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Chapter 3
by QueerKestrel
Spend some time with Emily, or soldier on to face down your ex alone?
Can't say no to that smile
You glance behind you, toward the distant soccer field. Imagining Tony out there, stretching, running, laughing with his teammates, relaxed in the knowledge of his power over you. Shuddering, you turn back to Emily.
Emily.
Her sweet smile, warm and inviting with just a hint of shy insecurity. Her emerald eyes pulling you back to a time before complications, before hurt and heartbreak. Why had you been avoiding her for so long? Just being near her is enough to push all the stress and anxiety of today into a distant corner of your mind. She always had that power. Like the sun on a September afternoon, her presence warmed you, relaxed you, made you feel like it could always be this easy.
Of course you want to be alone with her, even if she really does just want to catch up.
"Yeah, Em. That sounds... that sounds really nice, actually." You take a step toward her, already feeling that old warmth inside.
She lets out a breath that ends in a single giggle. "Cool. I've really missed you."
The two of you start walking together through the back entrance to the girl's locker room, and you feel a melancholy joy shudder through you at how easily you fall into step with her. As the two of you emerge into the wide open space of the changing room, lined with lockers on the walls and open showers on one side, you jab her arm with your elbow. "Sure beats the hell out of the locker room at old Lincoln Elementary, huh?"
She gives that little snort laugh of hers, the one that always made you crack up. "You can say that again, Charlie."
You don't remember exactly when you had met Emily. It had felt like you'd always been friends. Every memory of your childhood featured her. The two of you had been inseparable in that way only young best friends could be. Just a pair of rambunctious tomboys, terrorizing your teachers and exasperating your parents. Your early life together was a story of scuffed knees, torn clothes, and no acre of woodland left unexplored. The two of you used to make detailed plans about how you would run away together and live a free fantasy life in some hidden valley in the mountains, surviving off the land and having endless adventures.
Even as the two of you got older, and Emily left her tomboy side behind for the world of makeup and shopping malls and boy bands, the one thing that never changed was your friendship. At first it had been a joke, with you teasing Emily for her newfound interest in "girly" things, and her teasing you right back for never outgrowing your tomboy phase. Eventually, though, you got the feeling it was more than just a phase you were stuck on. Watching Emily embrace her femininity more and more, you'd started to realize you were embracing something else.
"So, uh, what did you want to talk about?" You turn to face her as the two of you reach a bench by the lockers, feeling ridiculous about the butterflies in your stomach.
Emily looks down at her feet, her freckled cheeks turning an adorable shade of pink. "Oh, you know... I just wanna know... what's up with you." She suddenly looks up, locking eyes with you. "I... I like the new cut." She reaches a hand up to your face, her slender fingers brushing your purple hair away from your eyes. "It's.. it's really... you."
You don't recall a conscious decision. One moment you're watching her familiar, lovely face dance through a dozen emotions, feeling her warm breath across your lips. The next your mouth is on hers, hesitant at first, but soon strong, hungry, ****. Her hands are gentle, one cradling the back of your head while the other rests on your hip. Your hands grab at her back, pulling her against you, wanting to feel her softness and warmth and that old simple happiness that used to be your life.
Her lips part to allow entrance to your urgent tongue, and she pulls in a sharp breath through her nose as you squeeze her even tighter against you, one hand making its way down to her ass. It had always been like this, with her, ever since you gave each other your first kiss, so long ago. She had always been so soft, so sweet, so inviting. You had always made the first move, but every time it felt like she was the one making the decision. You could never say no to her.
Practice. That's what she called it. She wanted to practice being with a boy. There wasn't a boy she trusted enough, or liked enough, but there was you, her best friend. When she asked you to "pretend" to be a boy with her, a fire had flared deep inside you. At first you'd thought it was just the realization that the feelings you had for Emily were stronger and deeper than friendship. Soon, though, you started to realize there was something else happening. The euphoria you experienced wasn't just from seeing and touching and tasting the most important person in your life. It was because, when you were together in that way, you really did start to feel like a boy.
Emily breaks from the kiss but doesn't pull away, pressing her cheek against yours as she whispers "Oh Charlie... I missed this... I—"
You don't let her finish, pulling her mouth back onto yours and kissing her even harder. She makes a soft moan, almost a whimper, drawing something out from inside you. Before you know it, you've pressed her back against the lockers, your hands roaming over her body, pushing under her skirt and up her blouse, feeling her smooth warm skin once again.
You break the kiss this time, nibbling your way across her cheek and jaw to her ear. "And what about this, Em? Did you miss this?" Your hand in her skirt slips into her crack, your fingertips tickling the space between her puckered asshole and rapidly moistening pussy, and you smile as she pulls in a sharp gasp. She always loved when you teased her there.
"Oh Charlie... yes... please... I need more." Her voice in your ear is a **** whisper, pushing you to go faster, farther.
You feel the tips of your fingers start to sink inside her. "More, Em? More like this?" Repeating the tickling motion from earlier, a smile grows on your face as you hear her whimper and tremble. No matter how many other people you both dated, no matter how much you both insisted it was only a silly game, those "practice sessions" kept happening. In fact, you can remember them more clearly than any of your early encounters with other partners.
The feeling is impossible to resist now. You spin Emily around so she's facing the lockers, cupping a small perfect breast with one hand as your other starts to vigorously tease her clit. Nibbling and sucking on her neck, unable to suppress a giggle at the delicious sound of her moans, you start to squeeze her stiff nipple. Her breath catches in her throat, and she presses her ass back against you. You respond by thrusting forward with your hips, repeating the motion again and again to **** her slick pussy against your hand. If someone saw you it would almost look like you were fucking her.
Her body tenses, and a keening sound escapes her wide open mouth. You let out a contented sigh, your hands continuing to play with her through the orgasm. You had been her first. None of her early partners had been able to make her come, but with you she had been able to relax enough to allow the thrilling ecstasy of release to flow though her. You'd been a bit more experienced by that point, but she had been the first girl you'd gotten off. The memory of that moment comes flooding back now, and as you cradle her trembling body against you the echo of that youthful intimacy pierces your heart with bittersweet longing.
Why couldn't you have held on to that feeling a little longer?
Emily sucks in a few gulping breaths and twists around in your arms, covering your mouth with a kiss. After a moment she draws back and looks you in the eyes, her face flushed. "Oh Charlie, that was..." her eyes drop down, and her hands come up to squeeze your shoulders. "You still make me feel like no one else."
A lump forms in your throat, and for once you find yourself at a loss for words. It had been so long since you'd allowed yourself to think about your feelings for her that the strength and intensity of those feelings now threatens to overwhelm you.
Thankfully, she saves you from needing to respond. Her eyes come back up to meet yours, and you see a look of thrilling heat in them. "Alright Charlie, now it's my turn." She pushes you back and down, forcing you to sit on the bench behind you. She comes down to her knees in front of you, her hands deftly undoing the front of your black jeans. "I need to taste you again."
As she pulls your pants and panties down and off your long legs, you're frozen by a potent mix of lust and longing. Mesmerized, you watch as she kisses her way up the sensitive skin of your inner thighs. She gently blows on your damp bush, making you shudder. A look of bliss fills her gorgeous face as she closes her eyes and breathes in through her nose. "Oh Charlie, you always smelled like heaven." With that, she leans forward, and her tongue meets your wetness, and your heart sings out.
She was always ever the only one who could make you feel like this, heart and body and soul united in pure joy. After a lifetime of being closer than sisters, and years of exploring each other's bodies, you finally ended up making things official the summer before sophomore year. It had been incredible at first. Perfect, like her. The feeling of holding her hand the first time you walked through the halls of your school as a couple had been like flying. Being able to declare to all the world that she was yours, and you were hers, made you feel like the king of the universe. What more could you ever want?
But it had been too much. The depth and intensity of your feelings for each other made even the smallest stumbling blocks feel like immovable mountains. The unspoken expectations of moving from best friends to girlfriends started to weigh on even the most innocent of interactions. Instead of making the sex easier and better, every encounter was now fraught with the knowledge that you were supposed to be doing this, and suddenly things became complicated. All of it was simply too much for your young selves to navigate, and after nearly a year of being a couple things suddenly fell apart. The fights and the words and the tearful silences were still seared into your memory. The friendship that had once defined your life, that had felt like the one unchangeable thing in the world, was changed forever.
So you ran. Blinded by tears, drowning in pain and regret, you ran away from Emily, unable to bear facing her again.
And that's when Tony found you.
Tearing yourself away from your memories, you return to the present, to the ecstasy of Emily's tongue dancing over and inside your pussy. Your hands are tangled in her hair and your breaths are heavy and ragged. A mirror across the locker room catches your eye. You can see your face, and just the back of her head as it moves. She's doing that thing that always drove you wild, moving her whole upper body to give her tongue different angles of access to you. It feels amazing, as it always did, but in the mirror it makes her head look like it's bobbing up and down. Almost like she were sucking a cock.
Your cock.
That spark of a thought ignites something inside you, blending with the intense pleasure of her tongue and the simple joy of being close to Emily again, and suddenly you feel an orgasm rush towards you. Body tensing, hands grabbing at Emily's hair, you groan in anticipation, and that's when she pulls away.
"Em-emily? I... that was... what are you doing?"
She gives you a wicked grin. "Sorry, I really need to be getting to practice." She stands and quickly strips out of her blouse and skirt, leaving you panting and watching her wonderful body as she changes into her athletic shorts and running top. "That... wow... Charlie I didn't realize how much I'd missed that... missed you."
You try to catch your breath as you look up at her. "Yeah, I... holy shit, Em."
She leans down, bringing her face close to yours. "I don't want to make things weird, but... I'd love if I could maybe finish the job later." She kisses you, gently, letting you taste yourself on her lips. You want to pull her closer, kiss her harder, but you can't seem to move. After too brief a moment, she pulls back. "Hold that thought, ok Charlie?"
You watch her walk out before you can respond, and you feel your heart yearn for her presence just as your body burns for her touch. When she disappears from view down the entryway, your eyes flick back to the mirror, and you take a closer look at your face. It isn't just lust and confused emotion you see. Your features seem sharper, your expression subtly different in a way that's hard to capture with words. That part of you that Emily first brought out so long ago, the part that wanted to do more than "pretend" to be a boy, is fully on the surface now.
This is all too much. You'd never been good at dealing with these kinds of feelings, and reckoning with your gender is the last thing you want to do on top of the tangle of emotions Emily brought up. Your hand reaches down to your pussy. Maybe just a quick orgasm to clear your head before anyone else shows up, and then you can go face down Tony. You'd nearly forgotten about him.
"Well look at that, girls! We caught someone with her pants down."
The sound of Jessica's voice and the giggles of her loyal pack of cheerleaders freeze you in place. Why her? Why now?
What else can this day throw at you?
Can you escape with your dignity?
Secret Masochist
A psychosexual journey
A high school senior has self-discovery upon her
Updated on Jun 4, 2025
by QueerKestrel
Created on Jan 21, 2019
by QueerKestrel
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