It had been three days since you’d brought it up–how the thought of anal filled you with an excitement mixed with dread. And though I’d never push, you brought it up again while you were nestled against me watching Netflix. Your fingers drew a languid circle around the button on my shirt.
“Daddy?” you asked softly.
“Yes…”
“You know what we were talking about the other day…I think I’m ready. I think I want to give you my ass.”
“Oh, baby,” I replied, tucking a strand of hair behind her ear, “I’m glad you’re feeling ready. We’ll go slow. Daddy will take care of you.”
You fingers found purchase on my shirt as you pulled your body into mine, pressing your face against my chest. I gently kissed your hair as my hand stroked your back. A moment of silent caresses and snuggled warmth.
“Do you feel ready now?” I asked. You nodded yes, still so close.
I took your hand and led you to the bedroom, pulling off your shirt as I sat you down. I leaned in to kiss your neck, unhooking your bra. My mouth following you down as you lay, then tracing down your body to your nipples, taking them into my mouth, gently sucking them into that warm wetness. I continued to kiss down your stomach. I raised up, saw your eyes catch mine and stopped for a moment to take you in. The anticipation in your eyes. The slickness around your tits. The slight bite of your lip as my hands reached to the waistband of your shorts.
I slid down your shorts and panties, and could instantly see how wet you were. “You’re such a good girl to trust daddy like this. I know how much you want it. But first, I need to taste you.”
I kissed up your thighs as you parted them more, my mouth finding the electric warmth of your skin. My tongue licked up your slit, parting your lips, and circling your clit before heading down again. As my tongue added to your wetness, I felt your hips rise to meet my mouth, pressing against my face, driven instinctively by those pleasure-seeking impulses I knew resided deep in you.
“Oh, daddy…you feel so good” you haltingly said as you began to pick up your pace. My hand traced over your stomach, palm against you, and took the place of my mouth as I rose.
“I know how good this feels for you. Focus on that build as my tongue explores” I directed as my hand moved to your thigh and pushed back. I licked up your pussy once again but now returned lower, letting my saliva and your juices mix as my tongue ranged over the taut ring of your asshole.
Your breath caught, surprised by the sudden warmth and slick searching of my mouth. I circled, as your hips returned to their rhythm that I knew so well.
“You are so beautiful. Every inch of you” I said momentarily taking my tongue away from your ass. I returned quickly and began licking back up to your dripping pussy. “Ok, now I want you to focus on your breathing and on my tongue on your clit” I said as my thumb pressed into your ass. A sudden gasp as “Daddy!” erupted from your lips paused my action. I held still inside you, and softly said, “It’s ok. We’ll go as slow as we need. You’re doing such a good job for daddy. Feel my tongue and sink back into that feeling.”
My mouth continued to lavish your pussy as I felt your hips move again, relaxing into being filled in a new way. My hand underneath your ass helped raise your hips to my mouth. I could feel your juices flowing over my thumb and knew you were getting close.
“You’re ready. Show me you’re a good girl and turn over for me.” As you positioned your ass in the air, I took in the shapeliness of your curves. I undid my shirt and quickly dropped my pants. You heard the click of the cap on the bottle of lube as I spread a generous amount on my stiff cock. You recoiled momentarily from the coldness of the lube as I spread it around your asshole. Then, my index finger slowly entered you.
You took in deep breaths and said “Ok daddy…that feels ok.”
“Good. You tell me if we need to go slower.” My finger had slightly picked up the pace of fucking your ass, feeling your muscles relax around me. I slid my hand out of you, seeing the gap momentarily where my finger had been and slid my cock down from the top of your ass to your awaiting hole. I started to press in, my hands on your hips, holding you steady.
Your deep breath broke sharply into a gasp as the tip of my cock started to enter you.
“Ah! Daddy, no wait!” you called out as your breathing quickened.
“Shhh, shhh. It’s ok. I’m right here,” I said calmly. We stayed locked, motionless, both on the brink. My hands slid up from your hips across your back, over your shoulders and back down. One hand slid underneath you, finding your still wet clit. “You’re such a good girl, and I know you can do this. Just focus on this feeling and your deep breaths.” My hand gently played over her clit. “Relax into that feeling.”
I don’t know if you felt like you were disappointing me. I imagine you wanted to be able to take daddy’s cock in you ass without an trouble. But what I’m certain of is that you only know the surface level of my profound appreciation for you in that moment. You trying desperately to take my cock, wanting daddy to feel all of you. As I stood there, my cock barely in your ass, I had laid before me the universe of your longing for me.
While our other movements froze, my hand found its rhythm against your eager clit. I could see the muscles in your back unclench as you settled in once again.
You couldn’t see, but I smiled as I said, “You’re such a good girl, but you have to lead now. Press back onto me when you feel ready.”
You exhaled and replied, “Thank you, daddy. I love you so much.”
Your hips moved, finding slightly different angles against me as I continued rubbing your clit. Your breathing deepened as I felt your first move backward, pressing my head full into you. You whimpered as I held there, letting you get used to my girth. It took a full minute before you tried to move back further, going even slower this time. My eyes, filled with anticipation and pride, watched as you took nearly every millimeter of me.
“Daddy…are you all the way in? You feel so, so big, daddy…”
“Almost. Do you need a little help?”
“Yes, daddy…I can take it.”
I placed one hand back on top of your hip and with a slow, measured thrust sank my cock the last inch fully into your ass. As I bottomed out, you released a deep groan, breaking into a squeaky whimper.
“Fuck… you’re so big, daddy. Fuck…you fill me so much! Daddy…do you like it daddy?”
I could hear your stuttered breathing interrupt your question. I could feel my cock twitch in your clenching ass and said, “Daddy loves it. You’re such a good girl and make daddy so happy and proud.”
It is a remarkable thing to see your limits and press up against them–to see the way you want to transcend them. You had done so, so much, and I wanted nothing more in that moment for you to feel some of the pleasure I took in being so proud of you.
I continued playing my fingers over your pussy, saying “You’re such a pretty girl for daddy. I want you to cum while my cock fills your ass. Breathe into it and cum for daddy. Cum for me.”
You took a little to really ease back into it, your hips moving shyly up and down, not yet able to rise freely with me in your ass. You were slow and you were perfect. I could feel you getting closer as you said, “Daddy, you make me feel so good!”
As you came, as pleasures crashed over you and your hips bucked more wildly than before, I knew it was tinged with pain. And I knew you relished this novel sensation. Your moan broke from deep in you. My hands steadied your hips as I whispered, “You’re so fucking beautiful.”
Your breathing slowed as you came down from your orgasm, my cock still stiff inside you. “Keep breathing,” I instructed as I started to slide myself out of you. Your hips shifted as I started to leave you, but my hands kept you still. “No, don’t move. I want you just like this,” I said as I slid my free cock over your ass. I stroked for a few seconds before I came hard across your ass, watching my cum drip down into the small void left by my cock a moment before.
As you felt my warm cum hit you, you and I both knew that your anal training had only started.
Source: reddit.com/r/eroticliterature/comments/t7nq29/an_especially_good_girl_tries_anal_for_the_first