Dirty Daddies: 2020 Anniversary Anthology

by Maren Smith

  “Yes, Daddy.”

  “Good. Give Daddy a kiss.” At the order, he tipped his head back, and I lowered my mouth to his. I groaned as they conformed so easily to mine. Everything about him was made to fit me. I nibbled and gently sucked at his bottom lip as he pushed our mouths harder together. His breathing was as harsh as mine. His left hand was fisted in the front of my shirt, tugging at the hair underneath it.

  “Boy, you're about to get yourself fucked on the first date,” I growled, as I kissed him harder, touched and squeezed every inch of him I could reach. My hand cupped him between his legs, and I felt the soft bulge behind his zipper. I pushed on it, and he gasped.

  “My packer rubs just the right spot when you play with me.”

  I worked it until he was panting, his hips restless. I couldn't take my gaze off his face. It was flushed, sweat beaded his forehead, and his eyes were tightly shut. I eased my touch until he looked at me.

  “You know what you're going to do?” He shook his head, and he whined as I increased the pressure just a bit. “You're going to come over next weekend on a Friday night. With a bag packed for the weekend. Bring all your favorite Little items, and we'll have Daddy and boy time. Would you like that?”

  My touch had turned lighter, more teasing. All it would take for me to come was just a few strokes of his ass rubbing on my cock. I wouldn't use my little boy that way.

  “Yes, Daddy. You're not going to let me get off, are you?”

  “No, because our first time is going to be special. You're going to come to me freely, without indecision. Daddy wants the boy and the man.” I arched my hips upward to show him how much I wanted him. “This is a serious start for me. Our talks. The way you feel.” I hugged him. “The neediness of your Little. I want it all. I'm hoping that you find your Daddy worthy enough to want to keep. Do you understand?”

  “Yes, Daddy. Can I at least have another kiss and more cuddling? I like this. Like calling you Daddy.” He thought he was sneaky, but I didn't miss he'd worked some buttons loose to get his fingers into my chest hair.

  “And I like calling you my boy,” I said as I brought my lips back to his. He whimpered at the first touch, and I kissed him, touched him, but avoided his groin. I wanted to do this right, not some quick fuck on the first date. He was special, and I wanted to make sure he knew it; that he knew he was important. He was mine.

  Chapter Five

  Whisper

  My hands shook as I tightly held my overnight bag and stood on Anderson's steps. We'd been sharing meals, either getting together for dinner or lunch somewhere, and every day, we'd talk before and after work. I was too excited to stand still. My Little was going to finally have a Daddy.

  I'd thought I'd be nervous, maybe even scared, but I'd been smiling all day. My coworkers had even asked about it. I'd told them I had a date. Anderson hadn't joined me for lunch. He had a meeting he wanted to get out of the way so he could give me his full attention. Bell had called to ask me to come out with him that weekend. I said I had plans, but I hadn't shared what they were. I wasn't sure how my best friend was going to react to this.

  The door opened, and I tilted my head back a bit to see him smiling at me.

  “Hi, baby boy, you're early.”

  “I was too excited to sit at home. Is it okay?”

  “Of course, come on in. Let me take your bag.” I handed it over and crossed the threshold. “Does this have all your things in it?”

  “Yes, all my favorite things. I also brought my cup, plate, and all, too.”

  “Good, I did do some shopping for you this week. We'll look at your presents later. Right now, Daddy wants a kiss.” He pinched my chin and tipped my head back, and then his lips came down on mine.

  He didn't let it go nearly far enough, and then he was leading me upstairs with his fingers through mine. We went to his bedroom, and he placed my bag on his bed. He released my hand to unzip it. When he laid the contents on the bed, he made two piles—big me and Little me. He placed everything but my Little items back into the bag.

  “I'm going to strip you now. Just strip. I won't touch you in an inappropriate way. Tonight is about your regression and letting you have Daddy and baby boy time, is that okay?”

  “Yes, Daddy,” I answered without hesitation.

  I watched him as he closed the few steps between us and he reached for the hem of my t-shirt. I couldn't take my attention from his handsome face. He didn't remove it quickly. He seemed to sense I needed time. As much as I wanted to be his, I was still uncertain if he'd change his mind.

  “Lift your arms, boy.”

  I did as he asked, and he pulled it over my head, then he dropped it to the floor. His fingertips traced the scars, and he smiled at me. He brushed a kiss to my forehead, and I savored the gentle caress. Then he was kneeling in front of me. He took off my shoes and socks. I held my breath as he popped the button on my jeans and stripped them down my legs. I stepped out. All that was left were my boxer briefs with my soft packer inside.

  His serene and loving expression didn't change, and that last sliver of insecurity started to fade away. When the elastic and cotton eased down my legs, he groaned. “I’m sorry. Just one, baby boy.” He leaned forward and pressed his face into my pubes. I felt him inhale, and he kissed me. And just as he said, it was one kiss and he moved back.

  “It doesn't bother you?”

  “It's your body, and I love it. Do you want your packer in your training pants?”

  “Don't need it. It doesn't fit right in my training pants.”

  “Okay,” he said, as he reached for the clothes he'd separated out. He pulled the thick cotton underpants up my legs, adjusted them until they were straight, and helped me slip my feet into my onesie footie pajamas. I ran hot, so they were thin, super-soft cotton ones. He dressed me easily.

  He zipped it all the way up. The rubber nipple of my pacifier rubbed across my lips, and I opened my mouth. As soon as I clamped my lips around it, a calm came over me. My Little was probably too old for a paci, but I liked it.

  “My baby boy is adorable,” he whispered, almost in awe as he stood and cupped my cheeks, another kiss brushed my forehead, then the tip of my nose. When he lifted me, he braced my bottom on his forearm and effortlessly carried me downstairs to the kitchen after grabbing my purple plastic plate and utensils.

  He set me on one of the barstools. “Don't move while Daddy fixes your dinner.”

  I nodded, and again, I couldn't take my gaze off him. He filled my plate with chicken nuggets and macaroni and cheese. He cut up the nuggets to cool as he took a cup from the dish drainer, and he poured some juice into it before screwing the top on. I was just happy to sit there and watch everything he did. He kept glancing at me to make sure I hadn't moved.

  “Ready for dinner?”

  I slipped my paci out and held it in my hands as I lowered them to my lap. “Yes, Daddy, thank you.”

  “You're welcome,” he said as he served me dinner.

  I went to pick up my fork, and his soft no made me stop.

  “I'll take care of that. I love feeding you. This is something you're used to doing for yourself, but Daddy needs to take care of you. While you're in your Little space, I'll attend your every need, from feeding you to taking you to the potty. This makes me happy. Will it do the same for you?”

  I nodded and smiled as he fed me, and he easily ate his own dinner as he focused on me. I gave myself over—felt the peace because it was different from when I did this alone. Something missing and finally found. He didn't rush. He praised me and rewarded me with gentle kisses to my cheeks or forehead.

  Time passed, and I didn't count the minutes or check the clock to calculate how long I had until the end. Adult me took a backseat.

  “Last bite.” I parted my lips and took it. “Such a good boy. I'm going to put you on a blanket in the living room to play while Daddy washes the dishes. I have it all ready for you.” He handed me my cup, and I hugged it to my chest as he lifted me i
nto his arms.

  I softly gasped as I saw the big yellow blanket with coloring books, oversized crayons, and a few toys, along with a brown teddy bear with a purple bow. He lowered me to the blanket, made sure I had everything I needed, and he left the room only after turning on cartoons.

  My face hurt from smiling as I laid down on the blanket, picked the coloring book I wanted, and started filling in the space between the lines. Occasionally, I'd play with one of my toys or cuddle with my bear. It was all too perfect, and the tears started building in my eyes. I dried them by burying my face against the plush belly of the teddy.

  I wasn't upset or sad because it was a relief. When we'd planned this, I'd anticipated awkwardness. Someone else seeing me like this, in my onesie and training pants, wanting to be fed or bathed. While I didn't feel it was wrong, having someone else observe it was exposing me to rejection. He'd looked at me naked and had been turned on by me. My Little had his full attention and care. I'd unconsciously prepared for the worst.

  “Hey, baby boy, what's wrong?” His question was quickly followed with me being pulled onto his lap. He rocked me as the tears came a bit faster.

  “I don't know.”

  “Is this too much?”

  I shook my head. I didn't want it to end.

  “This is your first time with a Daddy taking care of you. Of course it would be a bit overwhelming. Is that it?”

  “A bit.”

  “We'll sit on the couch, and I'll hold you. What happens between us is about us being happy. As long as these”—he used his thumb to swipe away my tears—”are happy tears, we're good.”

  “Happy and relieved.” I held tight to his neck with one arm as he carried me to the couch and sat down with me cradled on his lap.

  “You have an hour of cartoons, and then it's time for your bath.”

  “Yes, Daddy.” I only half-watched the show that was on. As he rocked a bit and patted my bottom, the too much too soon feeling faded away. My eyes became heavy, and I tipped my head back to find him staring down at me. His eyes were crinkled at the corners, his soft smile framed by his mustache and beard. I brought my hand to his cheek, stroking the short length of his beard. He brushed a kiss to my mouth but didn't go any further. There was no trying to move me out of my Little space. No headlong hurry into some other main show—appeasing me for the sake of fucking me. He was as content as I was just to hold me to his chest and let me simply be.

  “Are you ready for your bath?”

  My head bobbed, and I squeaked as he leaned forward, giggling as he crushed me a bit getting to the remote. He chuckled as he moved me off his lap to turn off all the lights and making sure the door was locked. Once I was back in his arms, I completely relaxed and let every muscle go loose.

  No more second thoughts. I'd delayed my own happiness too long, and I was going to hold on to the acceptance.

  Chapter Six

  Anderson

  I carried him to bed, and he was relaxed in my arms. All night he'd loved being Little. We'd watched cartoons. I'd made him food and fed him every bite, giving him his sippy cup, and then we'd colored. There were a lot of cuddles. My long-dormant Daddy had loved it, reading him a story and having him trust me to care for all his needs from feeding to potty time.

  It was time for a bath then bedtime. I couldn't wait to hold and touch him. I'd kept our time platonic, his regression was nonsexual, but when he got in my bed, I wanted to love on him. When I'd stripped him and changed him into his cloth training pants and his onesie, he'd been gorgeous. Slimly built with a slightly defined chest and a soft little paunch to his belly. I loved every part of him I saw.

  I'd seen his nervousness when I removed his pants. His body was perfect because it was his, and he was comfortable in his skin. He'd told me he hadn't been naked with anyone since his transition. That he was happy with where he was. That's all I wanted. I stopped in my bathroom and let his legs go so he could stand next to the tub.

  “Come on, boy, it's time for your bath, and then you're getting into Daddy's bed. As much as I want you there, I do want you to be sure. I want to love on you so badly, but I don't want you to wake up tomorrow with regrets. Tell me now if you want to wait, and we'll just sleep.”

  “Will you stop if I'm suddenly not ready?”

  “Baby, you can tell me no at any point. Even if I'm inside you, you tell me it doesn't feel right, and I'll be happy just to hold you while we sleep. I've spent every second I could with you, making sure you were comfortable with me…that you'd come to trust me. And I won't break that developing trust for anything. Okay?”

  He nodded, and I turned to start filling the tub, making sure the water wasn't too hot. I added bubbles, and bath toys were lined up on the ledge for him to play with if he wanted. I pivoted to turn back to him. I stripped him as gently as I'd dressed him until he was naked. My hands went to his waist, and after I lifted him into the tub, he lowered into the water. I washed his hair and rinsed it with a cup, slicking the silky strands back from his face.

  “My boy is adorable.”

  There was his blush again. He was terrible at taking compliments. It didn't matter how small they were, they always embarrassed him. I bathed him slowly, taking pleasure in touching him—caring for him. He tensed slightly when I washed between his legs.

  “We're going to address that? Do you not want me to touch you there?”

  “You're the first person to do it except myself since I started testosterone. It just took me by surprise. I love when you touch me. Um, can we put Little me to metaphorical bed, right now?”

  “Is that what you want?”

  “Yeah.”

  “What do you like your genitals to be called?”

  “Pussy and clit are fine. I'm a man with a vagina. I know everyone is different. Thank you for asking.”

  “If that ever changes and you want to call them something else, all you have to do is say so. With that out of the way…” I growled as I took his lips in a rough kiss. I stroked his clit—it was a few inches hard and peeked from his slit. His breath shuddered against my mouth. I jacked him quicker with my fingers, and he was tearing at the front of my shirt.

  “Anderson.”

  “That's right, baby, show me how you like being Daddy's big boy.”

  A strong shudder went through him, and my cock hardened almost painfully. I manhandled him out of the tub to set his feet on the mat. I barely got him dried off as he was fighting me, not knowing if he wanted my shirt off or my pants open.

  “Do you have lube? I don't get wet like I used to.”

  “I've gotten you taken care of, condoms and lube are waiting for us.” As soon as the words were out of my mouth, he was rushing out the bathroom door. His sexy ass was jiggling a bit with his strides. I tore my shirt over my head and followed him in time to find him on my bed, the covers thrown to the foot of it.

  His legs were raised, his feet flat on the mattress, and he was rubbing his long clit. I quickly retrieved the new bottle of lube and a few condoms. Tossing them on the bed, I leaned over, curling my arms under his legs and scooting him more toward the middle of the mattress.

  I'd been waiting for this. “Fuck, you're sexy all ready for me. My fantasies and jerking off didn't come goddamn close.” I didn't give him a chance to answer. Instead, I wrapped my lips around his clit and felt the distended peak on my tongue. His hands were fisted in my hair, and his strong thighs squeezed my head as I sucked him off.

  “Don't stop, fuck.” His voice cracked, and he jerked as I smacked his thigh for cursing.

  I buried my face between his legs, snuffled as I opened my mouth, every time I flicked him with my tongue, he humped his hips. I jerked upright, tearing at the front of my jeans to get them undone. I shoved them down my legs, kicked them aside, and then opened the lube. I coated my middle and index fingers, spread my hand over his belly, and worked my fingers into his tight pussy.

  He was violently riding my hand as he played with himself. I added more lube to
get him nice and ready for me. I couldn't take another minute.

  “Are you ready to get fucked?”

  “Beyond ready.” His fingers took over where I'd left off, and my hands were shaking as I barely got the condom on. My dick was hard and flushed, so ready to feel my boy wrapped around it. I got on the bed, stretched out between his spread legs. I held my dick in one hand and lined it up. As soon as I kissed him, I thrust my hips forward causing our groans to meld.

  “Fuck, boy, that's like coming home,” I rumbled against his lips as I placed my hands on the mattress so that his knees were braced on my arms.

  His fingers were twisted in my hair, our kisses awkward as he bounced with the force of my thrusts. He removed his mouth from mine and looked down—he was watching me fuck into him.

  “You like watching Daddy fuck you?”

  “Uh-huh.” His answer was nothing more than a moan as I quickened the pace. He grunted and clenched his fingers in the thick hair on my chest.

  Our bodies were slicked with sweat, our pants and groans getting louder, and my hips slapping against him was pushing me closer to the edge.

  “Dammit, baby, stroke that fat clit for me,” I ordered through clenched teeth as my muscles protested my restraint. “Fuck,” I shouted as he did what I told him to do, and his fingertips stroked my cock at the same time. His free hand wrapped around the back of my head, and his lips met mine in an open-mouthed kiss as I closed my eyes that were stinging from sweat.

  I bit down hard on his bottom lip as I forced him to take every inch and spilled into the condom, his shout followed closely behind, and he clamped down hard on my cock. When I collapsed on top of him, he wrapped his arms and legs around me. Then I combed my fingers through his damp hair. We lazily kissed as we came down from our orgasm high.

  “You doing okay, baby boy?”

  “Very okay, Daddy.” His voice was husky as he drew his fingertips up and down my back. “My jack off sessions have become ridiculous since meeting you.”