The day came when we were going to Mallorca. And as a 15-year-old inexperienced when it came to girls, I was looking forward to lying at the pole and sneak-peeks at bikini-dressed girls.
My grandmother had invited me and my mum to Mallorca to celebrate her 60th birthday.
We were now at the end of our week. Every day had looked the same sun, watching the girls around the pole, going out for dinner with mum and grandma, then home, and when I got the chance, wanking myself off with pictures of the girls in my mind.
But this evening when we got home, mum had drunk too much and fell asleep straight away.
When I said I was tired and was going to bed, grandma said ‘please, can’t we sit here and talk a bit’ I didn’t have the heart to say no, so we sat on the sofa and made small talk.
Then, “What is your experience with girls?” my grandmother suddenly asked. I felt my face grow hot and stared down at my hands. No one had ever asked me something so personal before, especially not my grandmother.
“Um, not much really,” I mumbled, wishing I could disappear into the sofa cushions.
Grandma sipped her wine and leaned back. In the dim light of the apartment, she looked younger than her sixty years.
“I was just curious,” she said. “At your age, I was already quite experienced.”
My eyes widened. This was definitely not a conversation I’d expected to have. The room suddenly felt too warm, too small.
“I haven’t really… you know… done anything,” I admitted, surprising myself with my honesty. “Just looked, I guess.”
Grandma nodded thoughtfully. “I’ve noticed you watching the girls at the pool. That’s perfectly normal at your age.”
I squirmed uncomfortably, not sure where this conversation was heading. The silence stretched between us, broken only by the distant sounds of music from a nearby resort and my mother’s soft snoring from the bedroom.
“You know,” Grandma continued, refilling her wine glass, “sexual curiosity is a natural part of growing up. Nothing to be ashamed of.”
I nodded stiffly, still avoiding her gaze. My heart was pounding in my chest.
“Would you like me to teach you some things?” she asked casually, as if she’d just offered to show me how to bake cookies.
My head snapped up, and I stared at her in shock. “What do you mean?” I managed to choke out.
Grandma smiled, setting her wine glass down on the coffee table. “Just some basics. Things that might help you when you do meet a nice girl.” She shifted closer to me on the sofa, her perfume—something floral and expensive—filling the space between us.
I couldn’t believe what I was hearing. This was my grandmother. My sixty-year-old grandmother. And yet there was something in her eyes I’d never seen before, something that made my stomach twist with a mixture of confusion and unexpected interest.
“I… I don’t think that’s…” I stammered, unable to complete the thought.
“Just educational,” she clarified, her voice soft but confident. “Nothing inappropriate. Just some advice from someone who’s lived a full life.”
I swallowed hard, relief and disappointment battling within me. Of course that’s what she meant. What had I been thinking?
“Oh,” I said, my voice cracking slightly. “Okay.”
Grandma smiled, seemingly pleased with my response. “First lesson—confidence. Girls can sense insecurity like sharks smell blood.” She shifted on the sofa, turning to face me directly. “Look a girl in the eyes when you speak to her. Not just at her body.”
I nodded, feeling like I should be taking notes. This wasn’t so bad—just advice, like she’d said.
“Second,” she continued, “listening matters more than talking. Ask questions about her interests, her dreams. Girls want to be seen as whole people, not just bodies.”
“That makes sense,” I said, relaxing slightly. This was actually useful information.
“And third,” she said, her voice dropping a little, “when it comes to physical intimacy, always go slower than you think you should.”
I felt my face flush again but forced myself to maintain eye contact like she’d just instructed.
“Most boys your age rush everything,” she explained. “The secret is patience.” She reached out and patted my hand. The touch lingered a moment longer than necessary, and I felt a strange flutter in my stomach.
“Um, thank you for the advice,” I said, shifting slightly away. My mind was racing, unsure of what to make of this conversation.
Grandma took another sip of her wine, studying me over the rim of her glass. “You know, when I was young, I had a boy teach me everything. He was older, experienced. Sometimes that’s the best way to learn.”
I nodded awkwardly, not sure how to respond. The air between us felt charged with something I couldn’t name.
“Would you like me to show you how to properly kiss a woman?” she asked suddenly, her voice casual but her eyes intent.
My heart nearly stopped. “I… what?” I sputtered, certain I’d misheard her.
“Just the basics,” she said, waving her hand dismissively. “Nothing you couldn’t see in a movie. It would be purely educational.”
My mind raced, thoughts colliding like cars in a pile-up. This was wrong, wasn’t it? She was my grandmother. But something about the situation, the secrecy of it, the forbidden nature, sent a thrill through me that I couldn’t deny.
“I don’t think that’s a good idea,” I said weakly, even as I found myself leaning slightly toward her.
She smiled, a knowing look in her eyes. “Perhaps you’re right. I’m sorry if I made you uncomfortable.” She leaned back, creating distance between us, and I felt both relieved and disappointed.
“It’s okay,” I mumbled, staring at the carpet.
“Let me ask you something else then,” she said, her tone shifting to something more casual. “What kind of girls do you like? At the pool, I mean. I’ve noticed you watching them.”
I shifted uncomfortably, grateful for the change in subject. “I don’t know,” I said. “Just… pretty ones, I guess.”
Grandma laughed, the sound surprisingly youthful. “Everyone likes ‘pretty,’ but pretty means different things to different people.” She crossed her legs, her summer dress riding up slightly on her thigh. I forced my eyes away.
“The blonde one,” I admitted. “With the red bikini. And the Spanish girl with the long dark hair.” My voice grew quiet with embarrassment.
“Ah,” Grandma nodded. “You have good taste. Both beautiful in completely different ways.” She studied me thoughtfully. “You know, when I was younger, men would stare at me like that too.”
I couldn’t imagine it. Not that my grandmother wasn’t attractive for her age—she kept herself in good shape, dressed well, and clearly took care of herself—but I couldn’t picture her as a young woman surrounded by admirers.
Then she put her hand on my thigh while bending over and whispered in a hoarse voice would you like to enter the adult world tonight.
I felt like I’d been struck by lightning. Her warm hand on my thigh sent electric shocks through my body, and her words hung in the air between us like smoke. My throat went dry, and I couldn’t seem to form words. Was this really happening?
“I… I don’t understand,” I finally managed, my voice barely above a whisper.
She smiled, her face so close to mine I could smell the wine on her breath. “I think you do understand, darling. I’ve seen how you look at those girls. How your eyes linger. The desire in them.” Her fingers made small circles on my thigh.
My mind raced with conflicting thoughts. This was my grandmother. This was wrong. But my body was responding in ways I couldn’t control, and the forbidden nature of what she was suggesting only made it more exciting.
She leaned in closer, her lips brushing against my ear. “Tonight, I’m not your grandmother. I’m just a woman who wants to show a handsome young man the pleasures of intimacy.” Her hand moved higher on my thigh, and I felt myself hardening despite my confusion.
“What about Mom?” I whispered, glancing nervously toward the bedroom where my mother slept, wine-sedated and oblivious.
“She won’t wake until morning,” Grandma assured me, her fingers now dangerously close to the growing bulge in my shorts. “We have all night if you want it.” There was something predatory in her smile that both frightened and excited me.
I knew I should say no. I knew this crossed every boundary imaginable. But something inside me was responding to her words, to her touch. My teenage hormones were overwhelming my sense of right and wrong.
“I don’t know if we should,” I said weakly, even as I made no move to push her hand away.
“We shouldn’t,” she agreed, her voice low and seductive. “But that’s what makes it exciting, isn’t it?” Her fingers traced the outline of my erection through my shorts, and I inhaled sharply. “Your body seems to have made its decision already.”
My breathing was shallow now, my heart hammering against my ribs. The rational part of my brain was screaming at me to stop this, to get up and walk away. But another part—a primal, urgent part—wanted to let her teach me everything. I wanted to experience what I’d only imagined in my late-night fantasies.
“Yes,” I whispered, hardly believing the word had left my mouth.
Her smile widened, triumphant and hungry. “Good boy,” she murmured, leaning in to press her lips against mine.
The kiss was nothing like I’d imagined my first would be. There was no awkwardness, no fumbling. Her lips were soft but commanding, guiding mine with practiced ease. When her tongue slipped into my mouth, I gasped against her lips, my hands hovering uncertainly in the air before settling tentatively on her waist.
“Touch me,” she encouraged, breaking the kiss to look into my eyes. “Don’t be afraid.”
Her hands moved to the buttons of her blouse, undoing them slowly while maintaining eye contact. I watched, mesmerized, as she revealed a lace bra underneath, black against her pale skin. Despite her age, her body was surprisingly firm, curves still defined where they mattered most.
“Do you like what you see?” she asked, her voice husky with desire.
I nodded, unable to form words. My inexperienced hands reached out tentatively, hovering over her exposed skin.
“Go ahead,” she encouraged. “Touch them.”
I cupped her breast through the lace, marveling at how it felt both soft and firm beneath my palm. She sighed with pleasure, her eyes closing briefly.
“That’s it,” she whispered. “Now, let me show you how to touch a woman properly.”
She took my hands in hers, guiding them to the clasp of her bra. With shaking fingers, I fumbled with it until it came undone. The bra fell away, and I stared at her exposed breasts, unable to look away. They were smaller than the young women at the pool, but somehow more enticing because they were real, here, offered to me.
“Every woman is different,” she explained, “But most enjoy being touched like this.” She arched her back slightly, pushing herself further into my hands.
I was lost in sensation, barely able to believe what was happening. My grandmother—no, I reminded myself, tonight she wasn’t my grandmother, she was just a woman that was teaching me things I’d only dreamed about.
“Stand up,” she commanded suddenly.
I obeyed, rising unsteadily to my feet. My legs felt weak, my entire body trembling with anticipation and nerves. She knelt before me, her hands moving to the waistband of my shorts. I held my breath as she slowly pulled them down, along with my underwear, exposing me completely.
“My, my,” she murmured appreciatively, looking up at me with those knowing eyes. “You have nothing to be ashamed of.”
Her words sent a surge of pride through me, mixed with embarrassment and excitement. No one had ever seen me like this before. I watched, transfixed, as she wrapped her hand around me, stroking slowly.
“Tell me how this feels,” she instructed, her grip tightening slightly.
“Good,” I gasped, then, without warning I came and sprayed her right in the face.
“I’m sorry!” I gasped, mortified beyond words, my face burning with shame. “I didn’t mean to—I couldn’t—”
To my surprise, she laughed softly, wiping her face with the back of her hand. “Oh, darling, there’s nothing to apologize for. That’s perfectly natural for your first time.” Her voice held no judgment, only amusement and something like satisfaction.
I stood frozen, exposed and vulnerable, unable to look her in the eyes. My mind was a whirlwind of conflicting emotions—pleasure, shame, confusion, and a lingering arousal that hadn’t fully dissipated despite my release.
“Sit down,” she said gently, rising to her feet with surprising grace. “Let me clean up, and then we’ll continue your education.”
“Continue?” I repeated, uncertain if I’d heard her correctly. “But I just… I mean…”
“Oh, sweet boy,” she purred, cupping my face in her hands. “Did you think we were finished? That was just the beginning.” She pressed a soft kiss to my forehead. “The night is young, and you have so much more to learn.”
She walked to the bathroom, her hips swaying with deliberate sensuality. I remained on the sofa, my shorts around my ankles, trying to process what had just happened—what was still happening. Part of me wanted to pull up my pants and retreat to my bedroom, to pretend this was all a vivid, inappropriate dream. But another part, a stronger part, wanted to see where this forbidden lesson would lead.
Grandma returned moments later, her face freshly washed, her blouse still open to reveal her bare breasts. She carried a damp washcloth in her hand. “Let’s get you cleaned up too,” she said, her voice gentle but commanding.
I sat frozen as she knelt in front of me again, carefully cleaning me with the warm cloth. Her touch was tender, almost maternal, which only added to my confusion. Yet there was nothing maternal about the way she looked at me, her eyes dark with desire.
“Young men your age have remarkable recovery times,” she murmured, noticing my body’s immediate response to her touch. “Perfect for what I have in mind next.”
She took my hand and pulled me to my feet. “Come with me,” she said, leading me toward her bedroom. I followed in a daze, my shorts still around my ankles. I awkwardly kicked them off, nearly tripping in the process.
Her bedroom was dimly lit by a small lamp on the nightstand. The sheets were already turned down, as if she had been planning this all along. I wondered briefly if this had been her intention from the start, even before our conversation on the sofa. The thought sent a confusing mixture of unease and excitement through me.
“Take off your shirt,” she instructed, her voice soft but firm.
I obeyed, pulling my t-shirt over my head with trembling hands. Now I stood completely naked before her, exposed in every way. She circled me slowly, her eyes appraising me like a fine piece of art.
“Beautiful,” she murmured. “Youth is such a gift.”
She began to undress herself fully, slipping off her skirt to reveal matching black lace panties. Despite her age, her body was well-maintained—slim with gentle curves, her skin pale and surprisingly smooth. She must have noticed my stare.
“I’ve taken good care of myself,” she said, noticing my expression. “Good genes, regular exercise, and avoiding the sun.” She smiled, a hint of pride in her voice. “And now, I get to share the benefits of my experience with you.”
She slipped off her panties, revealing herself completely. I swallowed hard, my eyes fixed on the triangle of neatly trimmed hair between her thighs. This was nothing like the airbrushed images I’d seen online. This was real, intimate, intimidating.
“Lie down on the bed,” she instructed, her voice gentle but leaving no room for refusal.
I moved to the bed, lying on my back, feeling exposed and vulnerable. The sheets were cool against my heated skin. Grandma—no, not Grandma now, just a woman—came to lie beside me, her body close enough that I could feel her warmth.
“Tonight is about learning,” she whispered, her hand trailing down my chest. “About discovering pleasure—both yours and a woman’s.”
Her fingers circled my nipples, sending unexpected jolts of pleasure through me. I hadn’t realized that part of my body could be so sensitive. She seemed to read my surprise.
“The body is full of secret places that bring pleasure,” she explained, her voice taking on a teaching tone despite our intimate position. “Most young men focus only on the obvious parts. That’s why they disappoint their partners.”
Her hand continued its journey downward, over my stomach, which tensed beneath her touch. I was already hard again.
“Tonight, I’m going to teach you how to please a woman,” she said, her eyes holding mine. “How to touch her, taste her, make her body sing. And in return, you’ll experience pleasures you’ve never imagined.” Her smile was both predatory and nurturing, a combination that left me dizzy with anticipation.
She leaned down to kiss me again, deeper this time, her tongue exploring my mouth with practiced skill. I responded eagerly, my hands hesitantly moving to touch her body. She guided my hand to her breast, showing me how to caress her, how to tease her nipple between my fingers.
“That’s it,” she encouraged when I tentatively tried the technique without her guidance. “You’re a natural.”
Her praise sent a surge of confidence through me. I grew bolder, my other hand exploring the curve of her waist, the softness of her hip. She made a sound of approval deep in her throat.
“Now,” she whispered, “I want to teach you something most boys your age know nothing about.” She took my hand and guided it between her legs. “This is where a woman feels the most pleasure.”
I felt the heat and wetness beneath my fingers, so different from my own body. She guided my hand, showing me how to touch her, where to apply pressure, how to move my fingers in slow circles.
I watched her face, fascinated by the way her expression changed with my touch. Her eyes closed, her lips parted slightly. I was causing these reactions, I realized with a surge of pride. Me, the inexperienced fifteen-year-old who’d never even kissed a girl before tonight.
“Inside now,” she whispered, guiding my fingers. “Curl them slightly, like you’re beckoning someone to come closer.”
I followed her instructions, amazed at the silky warmth that enveloped my fingers. She gasped as I found a spot that seemed particularly sensitive, her back arching slightly off the bed.
“There,” she breathed. “Right there. That’s the spot most men never bother to find.”
I committed the location to memory, fascinated by her reactions. Her breathing had become faster, her chest rising and falling rapidly. A flush had spread across her skin, and I realized with amazement that I was bringing her pleasure—real pleasure, not the fake performances I’d seen in videos online.
“You’re a quick learner,” she murmured, her voice tight with need. “Now, I want to teach you something else.”
She gently removed my hand and shifted on the bed, positioning herself over me, her knees on either side of my head. I stared up at her, understanding what she wanted but suddenly nervous.
“Use your tongue,” she instructed, lowering herself until I could feel her heat against my face. “Explore, learn the taste, the texture. Pay attention to my reactions to guide you.”
I hesitated only for a moment before tentatively extending my tongue. The taste was unlike anything I’d experienced—musky, slightly salty, not unpleasant. I licked experimentally, watching her face for reactions.
“Yes,” she encouraged, her fingers tangling in my hair. “Now focus on the small bud at the top. Gently at first.”
I followed her instructions, circling my tongue around the spot she’d indicated. Her thighs tensed on either side of my head, and a small moan escaped her lips. The sound sent a surge of confidence through me. I was doing this right.
“Firmer now,” she gasped. “Don’t stop.”
I increased the pressure, establishing a rhythm with my tongue. Her hips began to move slightly, rocking against my face. I grasped her thighs to steady her, emboldened by her reactions.
Her breathing grew more ragged, her movements more urgent. “Inside,” she gasped. “Your fingers too.”
I slid two fingers inside her while continuing the motions with my tongue. The combination seemed to intensify her pleasure. Her thighs began to tremble, and a series of soft moans escaped her lips.
“Don’t stop,” she commanded, her voice tight with need. “I’m close.”
I maintained the rhythm, ignoring the ache in my jaw, the difficulty breathing. Her pleasure had become my sole focus, a challenge I was determined to meet. When her body suddenly tensed, her back arching dramatically, I knew I’d succeeded. She cried out, trying to muffle the sound with her hand, her body shuddering against my face. After what felt like an eternity, she collapsed beside me on the bed, her chest heaving, a satisfied smile on her face.
“Oh my,” she breathed, stroking my cheek with trembling fingers. “You’re certainly a natural at that.”
“Now,” she said, her breathing gradually slowing, “it’s time for the main event.” She shifted on the bed, positioning herself between my legs. “This is what it’s all been leading to.”
My heart hammered against my ribs. This was it—the moment I’d fantasized about countless times. But never, in my wildest dreams, had I imagined it happening like this.
She straddled me, taking me in her hand, positioning me at her entrance. “Watch my face,” she instructed. “See what brings a woman pleasure.”
Slowly, she lowered herself onto me, enveloping me in a warmth so intense I gasped, my fingers clutching at the sheets. Nothing had prepared me for this sensation—not my own hand, not the whispered locker room tales from schoolmates who claimed experience. This was overwhelming, all-consuming.
“Breathe,” she reminded me, her voice gentle despite the intensity of the moment. “Don’t rush. Feel everything.”
I fought against the urge to thrust upward, to lose myself in the pleasure. She moved slowly, deliberately, her eyes never leaving mine. I watched her expressions shift, learning what movements seemed to please her most.
“Now,” she whispered, “you can move too. Find our rhythm together.”
I began to move with her, tentatively at first, then with growing confidence as I discovered the pleasure increased with each stroke. Together we found a pace that built our pleasure gradually, our bodies moving in harmony as if we’d done this countless times before.
“That’s it,” she encouraged, her voice thick with desire. “You’re doing wonderfully.”
My hands reaching up to cup her breasts as she rode me. She leaned into my touch, a smile of approval on her lips.
“I want to try something,” I said, surprising myself with my assertiveness.
She raised an eyebrow, intrigued. “Show me.”
I gently rolled us over so that I was on top, never breaking our connection. The new position gave me more control, allowing me to set the pace, the depth. I watched her face carefully, learning what movements made her breath catch, what angles made her eyes flutter closed.
“Yes,” she gasped as I found a rhythm that seemed to hit something deep inside her. Her nails dug into my back, urging me on. I was lost in the sensations, in the power of bringing her pleasure while experiencing my own.
“Harder,” she commanded, her voice barely more than a whisper. “Don’t hold back.”
I obeyed, driving into her with increased force, my inexperience balanced by youthful enthusiasm. The bed creaked beneath us, and somewhere in the back of my mind was a fleeting worry about waking my mother. But the thought disappeared as quickly as it had come, overwhelmed by the intensity of the moment.
I felt pressure building inside me, a familiar sensation but somehow different, more powerful than anything I’d experienced alone. “I’m going to—” I gasped, unable to complete the sentence.
“Yes,” she urged, her hands gripping my buttocks, pulling me deeper. “Let go. Come with me.”
Her words pushed me over the edge. I cried out, my body shuddering as waves of pleasure more intense than anything I’d ever felt crashed through me. I collapsed against her, breathless and trembling, my face buried in her neck.
For several minutes, we lay tangled together, our breathing gradually slowing. I felt different somehow—changed in ways I couldn’t articulate. My body hummed with satisfied exhaustion, but my mind was racing, trying to process what had just happened.
She stroked my hair gently, her touch now almost maternal again, which sent a confusing mix of emotions through me. “You did wonderfully,” she murmured. “A natural talent.”
Eventually, she shifted beneath me, and I rolled to the side. We lay facing each other in the dim light, her expression unreadable. I searched for something to say, some way to acknowledge what we had shared. But words seemed inadequate, trivial in the face of what had just occurred.
“You’re wondering what happens now,” she said softly, reading my thoughts with unsettling accuracy.
I nodded, suddenly acutely aware of our nakedness, our relationship, the enormity of the taboo we had broken.
“Now you sleep,” she said, brushing her fingers across my cheek. “And tomorrow, we return to our normal roles. I’ll be your grandmother again, celebrating her birthday with her daughter and grandson.”
“Just like that?” I asked, my voice barely audible.
She smiled, a hint of sadness in her eyes. “This night exists outside of time, outside of our regular lives. It’s a secret we’ll keep.” She pressed a gentle kiss on my mouth, got up from the bed and left the room.
I didn’t sleep many hours that night, and on the last day at the pole I looked more at my grandmother than at the young girls I had spied earlier in the week.
