Skip to content This is part 3 of the Daddy’s Sex Lessons Series. For part 1 My Daughter’s First Blowjob Lesson Or for part 2 My Daughter’s First Sex Lesson
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A few days passed after our night together. I tried to process what had happened between Emily and me, the line we’d crossed and what it meant for us going forward. I told myself it was a one-time thing, just a lesson to help her feel more confident, but I couldn’t stop replaying every moment in my head.
I first noticed something was off with Emily yesterday morning. She came down for breakfast, walking with a slightly stiff gait, and eased herself carefully into her chair at the kitchen table. When she shifted her weight to reach for the orange juice, a tiny wince crossed her face.
Today was no different. At lunch, she’d sat down gingerly, adjusting her position several times before finding a comfortable way to sit. I didn’t say anything, figuring maybe she’d pulled a muscle at the gym or slept wrong.
That evening, I gathered her laundry to wash. Emily was in the shower, so I took the opportunity to drop off her clean clothes in her room. As I set the folded pile on her bed, I noticed the corner of something poking out from under her mattress. I shouldn’t have looked. I knew that. But parental concern, at least that’s what I told myself, got the better of me.
I pulled out a small black drawstring bag. The material felt silky between my fingers as I loosened the string and peered inside. There was a bottle of clear anal lubricant, a small tapered butt plug with a jeweled base, and a medium-sized silicone dildo in a shade of purple.
Emily had been experimenting. It all made sense to me now, what she’d been attempting and why she’d been moving so carefully.
I should have put everything back and walked away. Instead, I stood frozen, the items still laid out on her bed, when I heard a sound from her en-suite bathroom. The shower had stopped running without me noticing, and she’d forgotten to close the door.
I moved toward the partially open bathroom door before I could think better of it. Steam billowed out, and through the gap, I saw Emily standing naked in front of the mirror. She had her back to the glass, looking over her shoulder at her reflection.
Her hair was wrapped in a towel, but the rest of her was completely bare. Water droplets still clung to her skin, running in rivulets down the curve of her spine and over the perfect round globes of her ass. Her waist was narrow, flaring into soft hips that gave her that hourglass figure. The backs of her thighs were smooth and toned, slightly tensed as she balanced on her toes.
In her hand was a purple dildo that looked identical to the other one, and she was trying to position it against her backdoor. She looked determined and frustrated as she tried to push the toy inside. She’d barely applied any lube, just a thin sheen of massage oil that caught the bathroom light, and her body was resisting the intrusion. She was too tense, muscles clenching instead of relaxing.
“Ah!” she gasped softly as the tip pressed against her tight ring. She bit her lower lip, brow furrowed in concentration.
My cock hardened instantly, straining against my jeans as I watched my daughter’s failed attempt. The sight of her perfectly round ass, the way she arched her back trying to find the right angle, the soft whimper of frustration that escaped her lips when the toy wouldn’t go in, it was too much.
I backed away silently, and then I left her room as quietly as I could, taking her laundry basket with me as an alibi.
For the rest of the evening, I couldn’t get the image out of my mind. At dinner, Emily sat across from me, still shifting uncomfortably in her chair. She wore loose pajama bottoms and a tank top, her damp hair loose. Every time she adjusted her position or winced slightly when she sat back down after getting up for a drink, I knew exactly why.
I watched her push food around her plate, lost in thought. The silence between us stretched until I couldn’t take it anymore.
“Em,” I said gently, setting down my fork. “You’ve been sitting funny all day. Is everything okay?”
Her head snapped up, eyes wide with alarm. A deep blush spread across her cheeks, traveling down her neck and disappearing beneath her tank top.
“What? I’m fine,” she said too quickly.
“Emily … I’ve noticed you wincing when you sit down. If something’s wrong, you can tell me.”
She stared at her plate for a long moment, the blush intensifying until her ears were pink. Finally, she took a deep breath and looked up at me through her lashes.
“I…” she started, then swallowed hard. “I’m wearing a butt plug right now. I bought some stuff online a few days ago. I wanted to try preparing myself so I wouldn’t be completely clueless.”
I set my silverware down carefully and cleared my throat. “Emily, sweetheart, that’s not something you need to wear during dinner or all day,” I said, keeping my voice calm and caring. “You don’t have to rush or do this alone. That kind of thing takes time and patience.”
She looked relieved that I wasn’t angry or disgusted. “Really? Because it’s been pretty uncomfortable. I’ve been wearing it for hours trying to get used to it.”
“Hours is way too long for a beginner,” I said. “You should start with just a few minutes, then gradually increase the time.”
She nodded, absorbing this information. Then her expression turned curious.
“Have you ever done anal before?” Emily asked suddenly, her eyes wide with curiosity. “Like, with Mom or anyone else?”
The question caught me off guard, but I saw no point in lying. This was supposed to be educational, after all.
“Yes,” I admitted, setting my water glass down carefully. “I have. Your mother and I tried it a few times. And I’ve had other partners who enjoyed it too.”
Emily’s face lit up with interest. She leaned forward, wincing slightly as she shifted on the plug still inside her. “Did it hurt her?” she asked eagerly. “Mom, I mean. How did you make it feel good for her? Do you have to go really, really slow?”
I cleared my throat, surprised by her directness but appreciating her genuine curiosity.
“It was uncomfortable for her at first,” I explained. “But we took it very slow, used plenty of lube, and made sure she was relaxed and aroused before trying anything. That’s the key, patience and preparation.”
Emily nodded, absorbing every word. “What does it feel like for the guy? Is it… better than regular sex?”
“It’s different,” I said thoughtfully. “Tighter in a different way. More intense sometimes. But what makes it good is that both people are enjoying it. If your partner is tense or in pain, it’s not going to be good for anyone.”
After we’d eaten, we decided to talk more about this in the living room. I did the dishes, and when I entered the living room, Emily was already settled on the couch, her phone in hand. She patted the spot next to her, and I sat down.
“I’ve been watching some videos,” she said, her voice dropping to a shy whisper. “To try to learn how to do it right.”
Before I could respond, she tilted her phone screen toward me. On it was a porn video, paused at the beginning. From the thumbnail, I could see it was clearly labeled as gentle anal for beginners. She pressed play, and we sat in silence watching as a young couple on screen engaged in gentle foreplay before moving to anal sex. The man was patient, using his fingers first, applying plenty of lube, and checking in with his partner constantly.
“How do they take it so deep?” Emily asked, pointing at a particular moment. “It looks like it should hurt, but she seems to like it. How do you relax enough for that? Can you really enjoy it?”
I swallowed hard before answering. “It takes practice and trust. The muscles need time to adjust and relax. And yes, with the right preparation and stimulation, many women do enjoy it. The area has a lot of nerve endings.”
She paused the video and turned to face me fully, those big blue eyes looking up at me with a mixture of vulnerability and determination.
“Daddy…” she said softly, the word hanging between us like a physical thing. “I tried by myself and it felt weird and uncomfortable. I don’t want to do it wrong or hurt myself.” She took a deep breath. “Will you teach me? The right way? Like you taught me the other stuff? Please… I trust you more than anyone.”
I closed my eyes for a moment, my heart hammering in my chest. Every rational part of me screamed to say no, to draw the line here. But when I opened my eyes and saw the trust in her gaze, the hope mixed with fear of rejection, I felt myself nodding.
“Alright,” I heard myself say. “But we go slow, and we stop the moment you’re uncomfortable. Promise me.”
“I promise,” she whispered, relief flooding her features.
We moved to her bedroom, closing the door behind us even though we were alone in the house. Emily stood in the center of the room, suddenly looking nervous despite her earlier boldness.
“We should undress,” I said gently. “And you should take that plug out first. You’ve had it in long enough.”
She nodded and turned away from me, pulling her tank top over her head. I stripped off my clothes as well, my cock already hardening at what was about to happen.
Emily was stunning in the soft light of her bedroom. Her chestnut hair fell in loose waves around her shoulders, framing her face perfectly. Her breasts were high and full, nipples pebbled in the cool air. Her waist dipped in before flaring to those soft hips, and between her legs, her pussy was already glistening with arousal.
She turned and bent over the edge of the bed, reaching back to carefully remove the jeweled plug. I watched as her tight ring stretched around the widest part before it popped free, leaving her puckered hole slightly open before slowly closing again. She set the toy aside and looked back at me over her shoulder.
“What now?” she asked.
“Get on all fours on the bed,” I instructed.
She climbed onto the mattress and positioned herself as I’d asked, her ass high in the air, back beautifully arched. I followed, kneeling behind her, taking in the perfect heart shape of her rear. Her pussy was visible between her thighs, pink and wet, and above it, the tight rosebud of her ass waited for my attention.
I reached for the bottle of lube she’d left on her nightstand. “First, you need much more lube than you think, sweetheart. Anal is different. The area doesn’t get naturally wet like your pussy, so we have to make everything slippery and relaxed.”
Emily stayed on all fours, looking back at me with those big blue eyes, nervous but trusting. I squeezed some thick lube onto my fingers, warming it between them before letting a long drizzle fall directly onto her tight little rosebud. She gasped at the cool sensation as the lube trickled down over her puckered hole and mixed with the wetness already leaking from her pussy.
I used two fingers to gently spread the lube around her entrance in slow circles, coating every fold. “Feel that? Nice and slippery. That’s what makes it possible without pain.” I pressed the pad of my middle finger lightly against her ring, not pushing in yet, just letting her get used to the pressure. “Relax, breathe out and push back a little, like you’re trying to open up.”
She took a deep breath and did as I asked. I felt her tight ring soften slightly under my touch. Slowly, I eased the tip of my lubed finger inside her. Emily let out a small whimper, her body tensing for a moment before she forced herself to relax again.
“Good girl,” I said, keeping my voice low and steady. “Just the tip for now. Tell me how it feels.”
“It feels… strange,” she whispered. “Full, but not bad. Keep going, Daddy.”
I pushed my finger deeper, inch by inch, until it was buried to the second knuckle. Her ass clenched around me as I gently twisted and pumped the single finger, spreading more lube inside her. I added a second squirt of lube directly onto my finger as I worked it in and out, making wet, obscene sounds. Her breathing grew heavier, and I noticed her pussy was dripping steadily onto the sheets.
“See how much easier it is with real lube?” I said, adding a second finger. I scissored them gently, stretching her slowly and carefully. “You were trying too hard by yourself. This is how we do it right, slow, lots of lube, and constant checking in. Does it hurt at all?”
“No… it feels weird but kind of good,” she moaned, pushing back against my hand. “I like it when you move them like that.”
I spent several minutes fingering her ass, gradually increasing the depth and speed while my other hand reached underneath to gently rub her clit. The combination made her moan louder, her hips rocking back to meet my fingers. When I felt her start to loosen up nicely, I pulled my fingers out and wiped them on a towel.
“Now for the real thing, baby. I’m going to use my cock, but we go extremely slow. If it’s too much, you tell me immediately.”
I coated my hard cock liberally with lube, stroking myself until every inch glistened. Then I added even more directly to her hole, watching it drip inside. I pressed the thick head against her slick, relaxed rosebud and held it there.
“Breathe out and push back gently, sweetheart. Let Daddy in.”
Emily nodded, gripping the sheets. As she exhaled and pushed, I applied steady, gentle pressure. The head of my cock slowly breached her tight ring, popping inside with a soft, wet sound. She gasped sharply, her whole body tensing.
“Ow… it’s big,” she whimpered.
“Stay relaxed,” I coached, freezing in place with just the head inside her. “The hardest part is the first inch. Breathe through it. You’re doing so well already.”
After a long moment, her breathing evened out and her muscles started to relax around me. I pushed forward another inch, then another, feeding my cock into her incredibly tight ass. The heat and pressure were intense, much tighter than her pussy. I groaned, fighting the urge to thrust hard.
“Halfway in now, baby. You’re taking Daddy’s cock in your ass so beautifully. How does it feel?”
“Full… so full,” she said. “It burns a little, but it’s starting to feel better. Keep going slow.”
I continued the slow invasion, watching every inch disappear between her perfect round cheeks until my hips finally pressed against her ass and I was buried to the hilt. I stayed completely still, letting her adjust to being completely filled.
“There we go,” I murmured, rubbing her lower back soothingly. “All the way inside your tight little ass. You did it, sweetheart.”
After giving her time to get used to the feeling, I started to fuck, tiny, shallow thrusts at first, barely pulling out before sliding back in. Each movement made wet, slick sounds from all the lube. Emily’s whimpers gradually turned into soft moans as the discomfort faded and pleasure started to build.
“Fuck… it’s starting to feel really good,” she said, pushing back against me.
I fucked her gently like that for several minutes, one hand reaching around to rub her clit in slow circles while my cock worked in and out of her ass. The dual stimulation had her moaning louder, her pussy dripping onto the bed.
Then I carefully pulled out, my cock glistening with lube. “Let’s switch positions, baby. I want to see your face while I’m inside you.”
I helped her roll onto her back and pulled her legs up, resting her ankles on my shoulders in a modified missionary position. I added fresh lube to both of us and pressed back against her slightly loosened butthole.
“Keep breathing and relaxing,” I reminded her as I pushed inside again. This angle let me sink in smoother and deeper. Once fully buried, I started slow, deep thrusts, watching her expressions closely and also her stretched ass.
Emily’s face was flushed, blue eyes locked on mine. With every thrust her breasts bounced gently and soft moans escaped her. I reached down and rubbed her clit again, keeping the rhythm steady but gentle.
“You’re taking Daddy so well in your ass,” I groaned. “Such a good girl for me.”
I kept fucking her ass with controlled strokes, building her pleasure until I felt her start to tremble.
“When are you gonna cum in my ass?” she asked with an impatient giggle.
“A couple of more thrusts,” I said.
I gripped her hips tighter and started thrusting harder, still controlled but with real depth now. Each stroke pulled my cock almost halfway out before I drove back in, her lubed ring stretching smoothly around my thickness. The lube made wet, filthy sounds as I fucked her, my hips slapping softly against her round cheeks.
Emily looked overwhelmed in pleasure. Her blue eyes widened with each deep thrust, lips parted in a constant soft “ah… ah…” moan. Her cheeks were flushed bright pink, eyebrows furrowed in concentration, but the discomfort had completely melted away. Every time I bottomed out, her mouth opened wider and her eyelids fluttered, a look of pure, surprised bliss crossing her features.
“Fuck, baby… your ass feels so good.”
I started thrusting harder, faster, the bed creaking beneath us. Her full breasts bounced with every impact, nipples tight and dark pink. She reached up and grabbed my shoulders, nails digging in as her moans grew louder and more desperate.
“Daddy… it feels so deep,” she gasped, her voice breaking. Her eyes stayed locked on mine, wide and glassy, that innocent yet hungry expression I’d come to crave. Every hard thrust made her gasp sharply, her tight ring fluttering and squeezing around my shaft as I slid in and out.
The pressure built fast. Her ass was milking me perfectly with every stroke. I could feel my balls tightening, the intense heat and grip pushing me right to the edge.
“I’m gonna cum, sweetheart,” I told her. “Daddy’s going to fill your ass.”
“Go on, cum in my ass,” she said, giggling again.
With a deep, guttural groan, I buried myself as deep as possible and came hard. Thick, hot spurts of cum erupted raw into her ass, pulsing deep inside her. I kept thrusting through my orgasm, grinding against her to push every drop as far in as it would go. The feeling of filling her tight little hole was overwhelming: warm, slick, and intensely intimate.
Emily’s eyes rolled back slightly, a soft, satisfied moan escaping her as she felt me flooding her. Her ass clenched around my cock, as if trying to milk out every last drop.
When the last pulse finally faded, I stayed buried deep inside her, both of us breathing hard. I leaned down and kissed her forehead, then her swollen lips, gently stroking her flushed cheek.
“You were perfect, baby,” I whispered as I pulled out from her ass, seeing her hole gape open before closing. A trickle of cum spilled out from her thoroughly-fucked ass.
She smiled up at me, still glowing and a little dazed. “Thank you for teaching me… I liked it more than I thought I would.”
“That’s my girl.”
The end.
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