The ice in my ginger ale had already melted. I could feel each cube shift when my hand trembled, the glass sweating against my palm. Jenna’s apartment smelled like vanilla candles and something else—her shampoo maybe, or just her—and I was trying not to breathe too deeply, afraid she’d notice how each inhale made my chest tight.
“You comfortable?” she asked from across her coffee table, tucking one bare leg beneath her on the loveseat. Her skirt—navy blue, shorter than what she wore to class—rode up just enough that I had to look at the wall behind her. At her bookshelf. At anything but the smooth expanse of thigh.
“Yeah, I’m good.” My voice cracked on ‘good.’ Twenty years old and my voice still cracked around pretty girls. Around Jenna especially.
She smiled, that soft knowing smile that made my stomach flip. “You can relax, Peter. It’s just me.”
Just her.
As if Jenna Moreau was ever just anything. As if I hadn’t been replaying every hallway conversation for the past three months, hadn’t been timing my exits to accidentally bump into her at the mailboxes.
“Tell me about your classes,” she said, shifting position. Her leg—the one not tucked—extended toward me, foot flexing. The movement pulled her skirt higher.
“They’re… they’re fine.” I forced my eyes to her face, but they betrayed me, dropping for just a second. Pink. A flash of pink cotton before I jerked my gaze back up. My face burned.
“Peter.” Her voice was gentle, almost amused. “What color are my panties?”
The question hit like cold water. My mouth opened, closed, opened again. “I—I wasn’t—”
“It’s okay.” She leaned forward slightly, elbows on her knees. The position should have hidden more. It didn’t. “I saw you looking. That’s natural. But I want you to tell me what you saw.”
“Jenna, I—”
“What color, Peter?” Softer now, like she was coaxing a frightened animal.
My throat felt thick. “Pink.”
“Good boy.” The praise sent an unexpected warmth through my chest. “See? That wasn’t so hard. Being honest with me is easy.”
She shifted again, uncrossing her legs completely before slowly crossing them the other way. This time I couldn’t look away fast enough. Pink cotton, and something else—was that a little design on them? My face burned hotter.
“You think about me sometimes, don’t you?” Her question was casual, conversational, but her eyes held mine. “When you’re alone in your apartment?”
I wanted to deny it. Wanted to laugh it off. But her gaze was patient, waiting, and somehow the lie wouldn’t come.
“Yes,” I whispered.
“How often?”
“I don’t—”
“Peter.” That maternal tone, gentle but firm. “How often do you think about me?”
“Every day.” The admission tumbled out, and with it came a strange relief, like setting down something heavy.
“And what do you do when you think about me?”
My hands were shaking now. I set the glass on the coffee table before I dropped it. “Jenna, please—”
“It’s okay, sweetie.” The endearment made something in my chest tighten. “This is normal. Natural. But I need you to say it.”
“I… I touch myself.”
“Your penis?” she prompted, as if we were discussing homework.
I nodded, unable to form words.
“Is it big, Peter? Your penis?”
The question made me want to sink into her carpet. “No.”
“How big?”
“It’s—it’s small.” Each word felt pulled from somewhere deep, somewhere I’d kept locked.
“How small?” Her voice stayed gentle, curious rather than mocking. “Have you measured?”
“Four inches,” I mumbled, the number barely audible. “Maybe four and a half.”
“That’s a little penis, isn’t it?” No judgment in her tone, just stating fact. “A little guy.”
I nodded, shame and something else—something warm and strange—flooding through me.
“How often do you touch your little guy thinking about me?” She leaned back, watching me with those dark eyes that seemed to see everything.
“Every night,” I admitted. “Sometimes… sometimes in the morning too.”
“So you’ve been training it,” she said thoughtfully. “All this time, you’ve been training your little penis for me.”
The phrase made no sense and perfect sense at the same time. “Training?”
“Stand up, Peter.”
My legs felt like water, but I stood.
“Come here.” She patted the carpet directly in front of her. “Right here.”
I moved around the coffee table, each step feeling enormous, until I stood before her. She had to look up slightly to meet my eyes, but somehow I felt smaller than ever.
“You’ve been practicing, haven’t you?” Her voice was hypnotic, rhythmic. “Every night with your hand. Every morning. Practicing for this moment.”
“I don’t understand—”
“Shh.” She reached out, her fingers barely grazing my hip through my jeans. “You’ve been getting your little guy ready. But ready for what, Peter?”
“I don’t know.”
“Ready to show me.” Her words were soft, certain. “Ready to parade for me.”
“Jenna—”
“Undo your belt.”
The command was gentle but absolute. My hands moved before I could think, fingers fumbling with the buckle. The leather whispered through the loops.
“Good boy. Now the button.”
Click. Such a small sound, but it echoed in my ears.
“The zipper.”
The metallic whisper of the zipper seemed impossibly loud. My jeans loosened, hanging on my hips.
“Push them down,” she instructed, her voice maintaining that same gentle authority. “To your ankles.”
“Jenna, I can’t—”
“You can, sweetie. You’ve been preparing for this. Training for this. Push them down.”
My thumbs hooked into the waistband. The denim was heavy, resistant, but I pushed. Down past my hips, my thighs, until the jeans pooled around my ankles. I stood before her in my boxers—plain blue cotton, a wet spot already forming where my erection pressed against the fabric.
“Look at that,” she murmured, but not unkindly. “Your little guy is so excited. He knows what’s happening.”
“Please—”
“The boxers too, Peter. Time for the full parade.”
“I can’t—”
“You can.” Her voice was silk, was warmth, was inevitable. “Your little flagpole wants to come out. See? Look how it’s pushing against the cotton. It wants to stand at attention for me.”
Little flagpole. The phrase should have been ridiculous, but something about how she said it—gentle, affectionate almost—made it feel right. True.
“But you have to ask it to come out,” she continued. “Ask your little flagpole if it wants to parade for me.”
This was insane. I was standing in my crush’s apartment with my pants around my ankles, and she wanted me to talk to my penis. But my mouth opened anyway.
“Do you… do you want to come out?” I whispered downward.
“It says yes,” Jenna answered for it. “See how it twitches? That’s your little flagpole saying yes. Now take down your boxers. Slowly.”
My hands trembled as they found the waistband. The elastic resisted, then gave, sliding down. The cool air hit my erection immediately—all four and a half inches of it, standing straight out, a drop of pre-cum already glistening at the tip.
“There he is,” Jenna said softly. “Your little flagpole, standing at attention. How does that feel?”
“Exposed,” I managed.
“But also right?” she suggested. “Like this is where you’re supposed to be? Pants around your ankles like a little boy who got caught being naughty?”
The comparison made me shudder. It was exactly how I felt—like a child caught doing something wrong, waiting for… what? Punishment? Forgiveness?
“You’ve been naughty, haven’t you?” Her voice was gentle, understanding. “Touching yourself every night. Every morning. Thinking about me.”
“Yes,” I whispered.
“But that’s what little flagpoles do,” she continued. “They stand up. They parade. They show what they’ve been practicing.”
She studied me for a moment, taking in everything—my flushed face, my trembling legs, my eager erection bobbing with each rapid heartbeat.
“Show me,” she said simply. “Show me how you practice.”
“What?”
“Touch your little flagpole. Show me your training routine.”
“Jenna, I can’t—”
“You can, sweetie. Just like when you’re alone in your room. Like when you think about me.” Her voice dropped lower, more intimate. “I want to see what you’ve been practicing all this time.”
My hand moved without conscious thought, wrapping around my shaft. The familiar grip, but completely different with her watching. My skin felt hot, electric.
“Slowly,” she instructed. “Show me how a little flagpole practices.”
I began to stroke, my hand moving in the rhythm I knew so well. Up and down. But slower, as she’d said. Each movement deliberate, displayed.
Up and down. Up and down.
“That’s it,” she encouraged. “Look how well-trained it is. All those nights of practice.”
Up and down. Up and down.
“Tell me what you think about,” she said. “When you practice alone.”
“You,” I gasped, my hand maintaining its rhythm. “Always you.”
Up and down. Up and down.
“What about me?”
“Your smile. Your… your legs. The way you laugh.”
Up and down. Up and down.
“And what do you imagine?”
“Kissing you. Touching you. Making you—” I stopped, embarrassment flooding through me even as my hand continued its motion.
“Making me what?” Her voice was patient, coaxing.
“Making you happy,” I finished lamely, but we both knew that wasn’t what I’d meant to say.
Up and down. Up and down.
“Your little flagpole can’t make me happy that way,” she said gently, no cruelty in it, just fact. “It’s too small for that. But look how happy it is just parading for me. Just showing me what it can do.”
Up and down. Up and down.
She was right. Despite the humiliation—or because of it—I was harder than I’d ever been. My erection throbbed in my grip, precum flowing steadily now, making everything slick.
“Say it,” she instructed. “Say ‘My little flagpole is on parade.'”
“My little flagpole is on parade,” I repeated, the words falling into rhythm with my strokes.
Up and down. Up and down.
“Again.”
“My little flagpole is on parade.”
Up and down. Up and down.
“It’s been practicing for you.”
“It’s been practicing for you,” I echoed, feeling myself getting close.
Up and down. Up and down.
“Every night.”
“Every night.”
Up and down. Up and down.
“Every morning.”
“Every morning.”
Up and down. Up and down.
“For this moment.”
“For this moment,” I gasped, my legs shaking.
“Get your other hand ready,” she said quickly. “Cup it below. Catch everything.”
I positioned my left hand beneath my erection, forming a cup, while my right maintained its rhythm.
Up and down. Up and down.
“My little flagpole is on parade,” I chanted without being asked, the words automatic now.
Up and down. Up and down.
“That’s it,” she soothed. “Let it show me what all that practice was for. Let your little flagpole finish its parade.”
Up and down. Up and—
“Now,” she commanded softly. “Show me now.”
The orgasm hit like a wave, my whole body shuddering. I watched, mortified and mesmerized, as my semen pulsed into my waiting palm—three, four, five spurts, more than I usually produced, as if my body had saved up for this moment.
“Good boy,” Jenna praised as I stood there, panting, pants around my ankles, one hand still gripping my softening penis, the other cupping my release. “Such a good little flagpole. Look what all that practice accomplished.”
I couldn’t speak, couldn’t move, could barely breathe. The room smelled like vanilla and sex and shame and something else—relief, maybe. Or belonging.
“From now on,” she said, her voice gentle but firm, “when you practice, you’ll think about this. About standing here with your pants around your ankles like a naughty little boy. About your flagpole on parade for me. Won’t you?”
“Yes,” I whispered, knowing it was true. Knowing I’d never be able to touch myself again without remembering this moment, this position, her eyes watching my most private ritual.
“And sometimes,” she continued, “you’ll come over here and show me your practice routine. So I can make sure your little flagpole is training properly. Would you like that?”
“Yes,” I said again, stronger this time, because despite everything—despite the humiliation, the exposure, the complete surrender of dignity—I wanted nothing more than to do this again. To parade for her. To show her my practice.
“Clean yourself up,” she said kindly, nodding toward the tissues on her side table. “Then pull up your pants. We’ll have some tea and talk about your new training schedule.”
As I reached for the tissues, still shaking, she added one more thing:
“Welcome to where you belong, Peter. Your little flagpole has found its purpose.”
And somehow, impossibly, I knew she was right.
