Skip to content I was a bit nervous as I stared at the text from my girlfriend, Cassandra. It was summer break, and we had just started dating. The first few dates had gone smoothly. I took her to a movie on the first one, and on the second, we went to the beach to play volleyball with her friends.
She was a little more experienced than I was. She wanted me to come over to her place tomorrow, and I was old enough to understand what that meant. She wanted to fuck. We were both twenty-one, but unlike her, I had never done it before. I knew how to kiss, I had decent social skills, and I was confident in most situations, just not when it came to sex. That made me nervous. I dreaded the idea of finishing too early and ruining the moment, or perhaps doing something that made her feel uncomfortable.
Luckily, I had a great relationship with my mom. We were open with each other, especially when it came to relationships and intimacy. She had always given me advice on how to talk to women, how to be confident, and how to take initiative, and if it hadn’t been for her, I probably wouldn’t have gotten this far.
I was sitting in my bedroom, and I decided to put my phone down. I searched for sex tips online, but all of them had something different to say and it ended up being more confusing than enlightening.
When I heard my mother’s car pull up outside, I looked out the window. I was always caught off guard when I saw her, but in a good way. I hated to admit it, but she was sexy, and I had some taboo fantasies about her that I struggled to ignore.
My mom worked as a secretary at a big bank downtown. She had long legs, a toned waist from hours at the gym, and thick, light brown hair. Her chest was full, and her cleavage drew more stares than anything I’d ever seen on a teenager. She wore a pair of stockings, a blouse, and a black pencil skirt. The whole outfit was unbelievably sexy, and I could feel myself getting hard just looking at her.
Once she stepped inside, she called out. “Ryan, are you there?”
I got up, happy to see her, and went downstairs. Her thick lips curled into a smile when she saw me. My eyes dropped to the valley of her tan breasts before I quickly looked back up to meet her almond-shaped eyes. She had a soft tan from her latest vacation. With her job, she could afford to travel frequently, and we lived comfortably as a result.
“How did the date go?” she asked.
“Pretty well,” I said.
“You’ve got to give me more details than that,” she said with a laugh. My mother was in her mid-forties but had the energy and warmth of someone half her age. “I’ll grab something to drink and we can sit outside.”
She was always curious about my personal life and made sure I was doing okay. She poured us some iced tea, and we sat together in the sun. She crossed her legs, showing off more of her thighs. I asked how her day had gone, which always made her smile.
“It went fine. How’s Cassandra?” she asked, taking a sip before setting the glass back on the table. She shifted a little closer to me, and I caught the scent of her floral perfume.
“I really like her,” I said. “We made out at the beach.”
“Anything more?” she asked, raising an eyebrow. “I mean, second date… It’s kind of common to take the next step.”
I scratched the back of my neck, unsure how to answer her question. I felt a little awkward bringing it up, and I think she could tell.
She leaned in a little closer, her warm thigh brushing against mine, making her warmth radiate up to my core. “What is it?” she asked, placing her hand on my thigh, which made the heat flow quicker. Her fingers moved in slow, sensual circles, but the warmth of her touch only made my thoughts spin faster. I shifted slightly in my seat, trying not to react, but I was already starting to get hard. My mother had that effect on me. She was just too sexy to ignore.
“You know you can talk to me about anything,” she said, giving my thigh a little squeeze. She was patient and kind, like always. But that touch, and the way she looked at me with genuine care, only added to the tension building inside me.
I exhaled slowly. “Well … Cassandra wants to take the next step. I think she wants to have sex tomorrow.”
She smiled a little, the exact answer she was looking for. “That’s not a bad thing.”
“No, I mean … It’s good. I want to. But I haven’t done it before. I’m still a virgin,” I said, dropping my eyes. “I’m scared I’ll mess it up. Or finish too fast or something.”
She didn’t laugh. She didn’t even look surprised. Instead, she gave my leg another gentle stroke, this time just a little higher, near my rising tent. I hoped she didn’t see it, and I hoped she didn’t believe it was she who was causing it. “Ryan, there’s nothing embarrassing about being a virgin. Everyone starts somewhere.”
I nodded, but the anxiety was still there. “But I don’t even know what to do.”
She leaned back slightly and gave me a thoughtful look. “Well, it’s not about doing everything perfectly. It’s about being there for each other. You start slow, make out a little and get comfortable with each other.”
She talked in a lecturing and loving voice, and as she spoke, I couldn’t help but imagine it wasn’t Cassandra she was talking about, but us. Her hand was still on my thigh. I could feel her warmth seeping through my shorts, and my mind drifted and sexual images of her and me popped up. I couldn’t sense any performance issue when it was with her, but I was too scared to bring it up.
“Let your hands explore a little,” she lectured me. “Touch her gently, let her touch you. You’ll learn what feels good by doing it. Go for her breasts, her hips … between her legs. Take your time and feel the heat build between you.”
As she said it, I felt that heat myself. My cock throbbed with each word, and the image in my mind wasn’t Cassandra at all anymore. It was my Mom. I imagined her lips on mine, her body pressed against me, my hands running over her curves, her voice whispering what to do as I explored her. The idea was so vivid, I had to shift again in my seat to adjust.
“You okay?” she asked, smiling at me.
“Yeah,” I said, swallowing hard. “Just … thinking.”
She brushed her fingers along my thigh one last time before pulling her hand back. “You’ll be fine, Ryan. Trust yourself. And remember, sex isn’t just about performance. It’s about love. Just relax, and enjoy it.”
I nodded again, trying to calm myself, even as my arousal kept pressing against my shorts. I sighed, my shoulders slumping. “I don’t know. I’m just nervous.”
She tilted her head slightly. Her hand moved over to my thigh again, but this time it slid higher. Then she pressed her palm over the bulge in my shorts, holding it there. Suddenly, I froze, but my cock hardened even further, and she felt it.
“Who are you thinking about?” she asked, searching my gaze.
I hesitated, then forced myself to say it. “You.”
Her eyes didn’t widen. She didn’t pull away. She just kept her hand there, listening.
“I know it’s wrong,” I added quickly. “But I’ve had these thoughts. About you. For a while now. And it’s not just about sex. I feel safe with you. I trust you. Honestly, it would mean a lot more to lose my virginity to you than to Cassandra.” I paused, heart racing. “God, that probably makes me sound like a freak. I get it if you think I’m weird.”
She shook her head and gave me a slow, reassuring smile. “Ryan, you’re not weird. We all have fantasies, even the ones we don’t admit out loud. There’s nothing wrong with how you feel.”
I swallowed hard, the tension pulsing through me, made worse by the way her hand still rested on me, gently stroking me through the fabric of my shorts. That touch felt insanely good. It made me wonder how intimacy would feel with her.
“I love you,” she said, leaning in just a little. “And if this would help you, if it would make you feel more confident, then yes, I’ll have sex with you.”
I stared at her. “Are you serious?”
She nodded, brushing her fingers lightly along my bulge as if she wanted this herself. “Of course. I know my body’s distracted you more than once. I’ve seen your eyes on my chest. That’s okay too.”
“Sorry,” I said, dropping my eyes. “There’s more to you than nice breasts.”
She giggled, the sound comforting in this tense situation. “That’s a good compliment, but remember, this has to stay between us. We don’t want to cause a scandal in this neighborhood, and I don’t want to lose my job either.”
“I won’t tell anyone about this, I promise.”
“I know I can trust you, Ryan.”
To my surprise, she dived straight into it. She leaned forward and pressed her thick lips against mine. I froze for a moment, then kissed her back. Her hand stayed on my lap, stroking gently while she let our mouths explore. I was awestruck at how smooth they felt, and the sweet taste of cherries on her lipstick. It drew me closer to her, making me a bit too excited.
“Take it slow,” she whispered between kisses, a string of saliva stretching from lip to lip. “Relax your jaw and let it flow. Kissing is about warming up and feeling each other before moving on to the hotter stuff.”
I nodded, and then we deepened the kiss. Her tongue slid over mine, like a soft stick of sweets. She guided my hand up to her chest and pressed it against her breast.
“Go ahead,” she said, smiling against my lips. “Squeeze it.”
I did. Her breast was soft, full and heavy in my palm. I ran my thumb over her nipple through the fabric, and she let out a pleased little sigh. Then her hand slipped under my shorts, her fingers wrapping around my length, the first incestuous contact.
“Mmm,” she said. “God, I love younger men.”
Her touch made my hips twitch and thrust forward, seeking the friction of her hand.
“Touch me,” she said.
I reached between her legs and slid my hand under her skirt. Her panties were already damp, a thick wet blotch in the middle. I pushed them aside and slipped two fingers over her folds, feeling how soaked she was.
“Just like that,” she whispered. “You feel that? That’s how much I want you.”
It felt like a dream, a forbidden one. My mom was letting me touch her like this, guiding and teaching me. Every second felt unreal.
We stood and slowly undressed each other. Her pencil skirt slid down her hips. She unbuttoned her blouse, revealing a pink bra. She unhooked it and let it fall to the floor, then stepped out of her stockings and panties. My eyes landed right on her chest. Her breasts were full and round at the bottom and slightly narrow at the top, topped with peachy nipples that looked so delicious to suck on. Her waist was toned, curving into wide hips and a smooth, flat stomach. Her pussy was neatly trimmed, the folds blushed with arousal, framed like petals of a secret, forbidden flower and pink as cherry blossom petals.
She smiled as she saw me staring. “Come, let’s go inside.”
We were getting a bit carried away. We went inside the living room, and she pulled the curtains together. She lay down on the couch and spread her legs. “Start by tasting me, just lightly and get comfortable with it.”
Climbing on top of the couch, I knelt between her thighs and leaned in, tongue brushing across her wetness. She moaned softly and grabbed my head to guide it closer to her heat.
“Use the flat of your tongue. Keep it slow and don’t rush. Let me feel it.”
I followed her instructions, and she tasted like ripe strawberries as I kept licking every inch of her, exploring her sweet petals. Her body responded quickly, her hips pressing forward as she got wetter. Her hand stroked my hair, pulling me closer and closer.
“Mmm, good,” she said with a wide smile. “Now lie back.”
She pushed me gently onto the couch and lowered herself between my legs. She eyed my erection, grabbing it and stroking it. Then she pointed the tip at her lips, and then my mother slid me inside her mouth, her lips wrapping tightly around my shaft. It felt so good, I nearly lost control right away.
“Oh, Mom,” I said, watching the taboo scene unfold right in front of my eyes.
She bobbed her head forward, her lips stretching as she swallowed several inches of my cock till her lips were about to touch down on my pubic bone.
“Wait—” I gasped, grabbing her wrist. “I’m gonna…”
She giggled, pulling her mouth off with a pop. “Too good?”
I nodded, breathless.
She lay back and opened her legs for me. “Ready to lose your virginity?”
I nodded, and I moved over her, my cock poised right at the entrance of her slick hole. “Push it in,” she told me. “I’m as horny as you.”
I nodded and tried to find the hole by rubbing the head of my cock around. Then she grabbed my erection and pointed it at her love hole. “Right there,” she told me in her warm voice.
I pushed forward, seeing my length entering her. The heat, tightness and taboo of her vagina overwhelmed me. It was just one stroke, but the friction was so sweet and intense it was enough to trigger an explosion. I barely got halfway in before it hit me, and when I pushed in the last inches, so I was fully sheathed inside her, I came hard, pumping my incestuous seed deep into her pussy.
I moaned sharply, hips trembling, and face red with embarrassment. “I’m sorry,” I said, trying to pull back.
She held me close and kissed my cheek, pulling me closer so I was still inside her. “Don’t say that. It’s normal and you’re learning.”
“But I came too quickly.”
She smiled. “No, you didn’t. And you know what? That’s better than the ones who can’t get hard or can’t come at all. Trust me, those exist.”
I chuckled. She sure knew how to make me feel better. “Yeah, but I want to last longer. I want to actually do it right.”
“You will,” she said, cupping my face. “You’re just excited. That’s not a bad thing. You just need to learn how to control it.”
I nodded, eager to hear more.
“Breathe deeply,” she said, running her hands over my back. “That’s the key. Most men hold their breath without realizing it. That makes them lose control. You have to stay calm. Let yourself feel, but don’t rush toward the edge.”
“Okay,” I said, taking in a slow breath.
She smiled again and kissed me, her lips tracing the seam of my lips before pulling back. “Let’s try again.”
I pulled back from the kiss, still rock hard but a little less sensitive. Then I guided myself back between her legs, and this time I found her hole by myself. I thrust my hips forward, pushing in inch by inch, watching her face as I filled her with my raw cock. The sensation was just as incredible as the first, tight, warm and slippery, but I focused on my breathing, like she told me. She wrapped her legs around me again and smiled.
“That’s it,” she whispered. “Nice and slow at first. Feel the heat between us.”
I started to thrust gently, and she met my movements, moaning softly into my ear.
“Don’t go too deep right away. Let her open up to you. Use your hips, not just your body weight. Feel the rhythm.”
I adjusted as she guided me, and the difference was immediate. I started to feel more in control. Her voice, her body, her scent, everything kept me turned on, but I stayed focused.
“You’re doing amazing,” she said between breaths. “You’re fucking me, Ryan. You’ve got it now.”
Her words made me proud, and I started thrusting faster, the wet sound of our bodies slapping together filling the room. Her moans grew louder, her nails digging into my back as her hips rocked with mine. I felt bold and more adventurous now. I couldn’t take my eyes off her bouncing, jiggling breasts, and I leaned forward to grope them both while I fucked her.
“That’s wonderful,” she said, biting her lower lip. “Try kissing my neck, too.”
I leaned in, resting some of my weight on her as I kept moving inside her. I found her neck and kissed it intimately. She moaned against my ear, then kissed my neck in return, making me gasp. Our lips met again, her breasts pressed between us, warm and soft as we kissed deeply. I kept a steady rhythm, each wet thrust drawing me closer to the edge.
I pulled back from her lips and glanced down, watching my cock slide in and out of her soaked pussy. Her lips stretched around me with each deep thrust, slick and shining as wetness spilled down her thighs and across her mound.
“Oh, Ryan, that feels so good,” she whispered, her voice full of pleasure.
“I know,” I said, breathless. “I’m almost there.”
“Go on. Don’t hold anything back.”
Her pussy fluttered around my shaft, tightening just enough to make the friction even more intense. I couldn’t help myself. I went harder, and the sound of our bodies clapping together grew louder. It was one of the most satisfying sounds I’d ever heard.
The pressure inside me built quickly, but this time I didn’t panic. I let it rise naturally, staying in sync with her rhythm.
“I’m close,” I whispered.
“Let it happen,” she said, her voice trembling with pleasure. “Give it to me.”
With a few more hard thrusts, I groaned, hips slamming against hers as I came deep inside her. I stayed buried, trembling as the orgasm rocked through me. She gasped and held me tightly, her body shaking along with mine. We shared that moment in silence, skin to skin, wrapped in something that felt surreal.
I pulled out slowly, almost in a daze, and watched my cum trickle from between her glistening lips. It looked unreal, like something from a dream.
We lay together for a while, catching our breath. She gently ran her fingers through my hair and kissed my temple.
“That felt like a dream,” she said.
I nodded, still overwhelmed. “I don’t even know what to say.”
She smiled and cupped my cheek. “You don’t have to say anything. You’re definitely ready for Cassandra now.”
“Thank you,” I said, leaning in to hug her, wrapping my arms around her warm body. “I don’t feel any performance anxiety now.”
“I’m glad … I just want to enjoy your life,” she said, pressing her lips to my cheek. “And if you want to do this again … it wouldn’t hurt.”
“I would love to,” I said.
“Me too,” she said, her eyes swimming with love and lust.
The end.
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