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[FM] First time anal with my partner brings out a praise kink

Mar 20, 2024

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cheng cuiping

I'm no stranger to anal. A former fling was obsessed with it, and I've tried it many times since then. And I generally fucking hate it. I know it's not “cool” for women to hate anal, but I usually cannot stand full on anal sex. Butt plugs? 10/10. Pegging someone else? 11/10. But taking a full dick up the ass? Nah, I'm good. That being said, it's something I'll occasionally indulge for the sake of a partner's pleasure. It's a trade-off and a kindness, like when someone will rewatch Scandal with me even if they hate it and know I'll talk the whole time.

My then-boyfriend/now-husband Henry and I talked extensively about anal probably in our first month of dating. I laid out my reasons for disliking it (long prep time, lack of personal enjoyment, feels weird to sit down for hours afterwards, etc.), and he laid out his reasons for liking it (pretty much just novelty). After I described my trade-off mentality, it became the yard stick for how much one of us did or didn't want to do something.

Him: "Want to go to [insert sports match here] this weekend?"

Me: "I'd rather get fucked up the ass."

Or

Me: "How willing are you to help my sister move next week?"

Him: "How willing are you to get fucked up the ass?"

He never brought anal up in a serious context after that first conversation, so I figured that he had either lost interest or decided not to deal with my dramatics. Until one fateful day when the hypothetical trade-off became a reality.

When we were dating long-distance, we tried to alternate locations each weekend and drive to each other's cities to keep things fair. One month, however, I had three weekends of obligations in my own city, and he kindly joined me for each of them. In the days leading into the fourth weekend, I got an invitation to my boss's house for a Friday night dinner party. Wincing to myself, I called Henry, fully prepared to go stag to the dinner party but feeling guilty about spending yet another weekend in my own apartment. "Don't hate me," I blurted the second he picked up the phone.

"Good morning to you too! What did you do?"

"Shauna-asked-me-over-to-dinner-on-Friday-and-I-should-really-go-to-impress-her-but-you-totally-don't-have-to-come-with-me-I'm-so-sorry!"

"Are you fucking kidding?"

"I'm sorry! I promise I'll spend the next four - no - FIVE weekends at your place. I can't get out of this."

"Lily..."

"Please don't hate me!"

He sighed, and I could picture him wearily rubbing his forehead in exasperation. It's an expression I had caused many many times before. "What time do I need to be there?"

"What? No, you don't have to come!"

"Am I not invited?"

"No, of course you're invited, but-"

"I'm not gonna make you go by yourself. Text me the details and have a really big fucking drink ready for me. You're DD'ing."

"I promise. I owe you one, I'm so sorry, I'm the worst!"

"It's really ok."

"I love you!"

"Yeah, uh-huh, love you too. Asshole."

It clearly wasn't intentional, but his reference to that particular body part gave me an idea. At worst it would be a funny joke and at best it would be a chance to show him my appreciation. The night of the dinner party, I greeted Henry at the door with a kiss, handed him a stiff drink, and told him to meet me in the bedroom when he was ready. "Do we even have time?" he laughed, dropping his bag on the ground and taking a swig.

"Oh, no, we aren't having sex right now."

"Oh ok."

"No, just - you'll fucking see, don't be annoying."

A few minutes later, he peeked his head around the door to my bedroom to see me dressed up for dinner and sitting on my bed. "Reporting for not-sex, ma'am," he saluted.

I opened my bedside table and removed a sleek silver butt plug and a bottle of lube, displaying them for him like a magician's assistant. "I know you'd rather get fucked up the ass than come tonight," I smirked, bending over the bed, lifting my skirt, and pulling my panties to the side, "So I figured I'd even the score a bit."

"No fucking way."

"Way."

I dripped some lube on the tip of the plug and slowly slid the tip in my ass, tossing my hair over my shoulder to look him in the eye as my body adjusted to the cold sensation. Henry crossed the room so quickly I didn't even hear his footsteps, his hand replacing mine to slide the plug in the rest of the way. He gave it a cautionary pull on the flared base to ensure it was in place before roaming his hands across my ass. One sharp slap to my right cheek made me yelp, but I barely had time to react before Henry was pulling me harshly against his body, one of his hands reaching around to cup my pussy and the other grabbing my throat and pulling me upright. His teeth scraped against my ear as he leaned in to whisper softly. "Are you telling me that I now have to think about fucking that tight ass of yours all night while trying to impress your boss?"

"Uh huh," I breathed smugly, arching my back to rub my ass against his hardening cock, "And I heard their dinner parties last for hours."

With a gentle squeeze of my throat, he released me, shaking his head and muttering to himself as he walked into the bathroom to get ready.

The dinner party was honestly uneventful. As much as I'd like to pretend that Henry and I sneaked into the bathroom for some steamy make out sessions or that I repeatedly flashed him the sight of the plug in my ass, we spent the evening acting like a wholesome couple who wanted nothing more than to entertain and get to know my boss and her wife. Around the time ten o'clock rolled around, we made a graceful exit, our arms full of leftovers that my boss's wife insisted on us taking home "to stay fed for the rest of the weekend."

I honestly thought he might have forgotten about the promise of anal until I turned on the light in my apartment, locked the door, and found myself pressed against the wall as Henry's mouth devoured mine. A moan escaped my lips, and I stood on my tiptoes to wrap my arms around his neck. He kissed down my throat, whispering softly against my skin. "I couldn't stop thinking about this," he murmured, shrugging his sport coat off and letting it fall haphazardly to the floor as he lowered himself to his knees.

Henry spun me around and lifted my dress, pulling my panties down roughly and spreading my cheeks to stare at the plug. "Fuck," he groaned, "I really need to fuck you."

And, at the worst possible moment, I yawned. We both paused. "Hey," he said softly, standing back up and turning me to face him, "If you're too tired, we can definitely press pause. Don't feel obligated to do this tonight. Or at all."

"No, I want to!" I answered truthfully, "It was just a long week. I am the absolute worst for making you come here again, and I really really want to do this."

"You're not the worst," he laughed, pressing gentle kisses on my lips as he guided me towards the bedroom.

"I'm a bad girl, and I deserve to be punished," I teased, kicking off my heels.

Henry lifted me in his arms to carry me the rest of the way, my legs instinctively wrapping around his waist. He rested me softly on the bed, trailing kisses down my body as he untied the front of my wrap dress and slid it off my shoulders. I unhooked and removed my bra, grabbed a towel to lay on the bedspread, and watched as he quickly undressed himself, the incredulous smile on his face making me laugh. He climbed on top of me, our lips crashing together. We wrapped our arms around each other. I couldn't get close enough to him. Henry pulled back after a moment. "Is this really happening? Do you need me to do anything before we start?”

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"Fuck yeah, it is," I laughed, grabbing the bottle of lube and putting it next to me on the towel, "Just please go slow."

"I promise."

He placed a pillow lower down on the bed and helped me turn over onto my stomach, my hips resting against the pillow. I waited patiently as he began liberally applying lube on his erection. After a moment, I felt Henry's hands spread my cheeks. He let out a low exhale. "Fuck. I don't know how long I'm gonna last."

"Bold of you to assume you're even gonna fit."

"Flattery will get you everywhere," he laughed, his right hand moving to gently grasp the plug's flared base, "Can I take this out?"

I nodded. "I need to hear you say it," he teased.

"Yes, you can take it out, dick."

"There's no need for name-calling."

"Sorry for being naughty. Are you going to show me what happens to bad girls now?"

He didn't say anything as he gently pulled out the plug. My body tensed and relaxed. Henry slowly rubbed a hand on my back. He squirted some lube on his pointer and middle finger and gradually inserted them in my ass. I heard the smile in his voice as he watched me force myself to relax. "There you go, Lily, you're doing so well," he whispered.

It was like an electric shock went up my body. My breathing quickened, my hands balling the sheets into fists. "Does that feel good, baby?" he asked quietly, his fingers slowly and rhythmically lubricating my ass.

"No, I mean, yes, but just - keep talking, please."

"You like it when I talk to you like this, sweetie?"

"Mm hmm," I murmured into a pillow, blushing wildly.

"You want me to keep telling you what a good girl you are?"

I buried my face in the pillow and nodded, embarrassment flooding my body. "Hey, it's ok," he whispered encouragingly, the hand that was not working my ass reaching up to stroke my hair, "I can keep talking."

"Thank you," I replied quietly, my voice unusually high-pitched.

"Of course, honey."

Henry gently removed his fingers and climbed up the bed to straddle my legs. "I'm going to try pushing in now, ok?"

I nodded, willing my body to relax and for the blood to leave my face. He placed one hand on the bed to the left of my face and leaned forward, his lips brushing against my back as the tip of his cock kissed the rim of my asshole. My muscles clenched as his head pushed inside, stretching my ass to accommodate him. I whimpered softly. "Shhh," he consoled, "You're doing so well, just a little bit more."

"I don't know if I can do this," I breathed.

"Color?"

He knew me so well. "Green."

"You can do this," he whispered encouragingly, slowly pushing more of his length inside me as I let out a long exhale, "Just breathe, baby, you can take it."

A whimper-moan burst from my throat as Henry pushed the rest of himself inside me. "Ohhh fuck," he groaned, "You feel so good, Lily. Fuck, you're so tight."

His chest rested against my back, his body weight pressing against me and his fingers lacing through mine. "I'm going to start fucking you, ok, baby?" he asked quietly.

I nodded, my whole body feeling warm. He let out a series of moans as he gave a few tentative, shallow thrusts. "Oh my god, Lily. Oh my fucking god."

His thrusts became smoother, longer. My clit ached to be touched, my pussy occasionally pulsating whenever Henry's grunts of pleasure sent shockwaves up from my cunt to my fingertips. "I'm not gonna last long like this. Can I cum inside you?"

I nodded again. "Please cum inside me," I begged, squeezing his hands.

"Fuck, you're such a good girl. You're doing so fucking well, you're gonna make me cum. Are you starting to enjoy yourself, baby?"

I nodded yet again, my cheeks unbearably warm. "Good. Fucking. Girl," he grunted, punctuating each word with a harsh thrust, "Fuck, I'm so proud of you."

A loud whimper exploded from my mouth, my ass rocking back to meet his thrusts and placing delicious intermittent pressure on my clit against the pillow beneath me. "Henry," I moaned, "Henry I need-"

"You're doing so well, I just need a little bit longer. Can you do this for me a little longer? Can you keep being so good for me?"

"Mmm," I moaned, a clitoral orgasm rapidly building as his thrusts turned into pounding, the rhythmic pressure of his body forcing me to rub me against the pillow, "Oh fuck, please don't stop talking."

"I need to hear you moan," he demanded, "I love making you feel good."

"Henry! Fuck, I'm getting close."

"Are you gonna cum from this, baby?" he panted in my ear, "You're such a good girl, letting me use your tight ass like this."

"Please don't stop please don't stop please don't stop!"

"I'm not gonna stop, sweetie, but I'm getting close. Can you take it if I go harder?"

"Yes," I breathed.

He slammed into me over and over again. I released one of his hands and reached beneath me to rub my clit. "Oh fuck, that's a good girl. Rub your clit for me. I need you to cum for me, can you do that for me, baby? Please be a good girl and cum for me while I fuck your ass, Lily, please."

I screamed into the pillow, my body spasming softly while my orgasm ripped through me. "There you go, baby, there you go. Breathe into it, you're doing so well," he praised, his forehead resting against the back of my shoulder as his voice grew tense, "Just a little while longer, I'm so proud of you. I'm almost there, baby, I'm so close."

Another couple of thrusts and Henry suddenly stilled, his loud groans blowing warm air across my face as his cock pulsated inside me and filled me with cum. "Fuck, Lily. You did such a good job."

He kissed across my shoulder and down my cheek, searching for my lips. I met his mouth hungrily, allowing his tongue entry as a tear of exertion escaped my eye, dripped down the bridge of my nose, and fell onto the bedspread. "Are you ok, baby?" he asked gently.

I smiled. "I didn't realize how much I liked being encouraged and taken care of," I admitted shyly.

"Well I didn't know how much I love encouraging you," he laughed, "I'm gonna pull out now, ok?"

I nodded. Henry kissed my cheek again and propped himself up on his forearms, slowly removing his softening cock as I let out another slow exhale. "There we go," he murmured, kissing down my back, "You did so well, sweetie."

“Really?”

“That was amazing.”

"Do I still have to drive the next five weekends?"

"Obviously," he laughed, "You're not getting off that easy."

"Fuck."

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