First Session with Daddy

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A shy Baby meets up with Ddaddy for their first session.
5.3k words
4.42
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9

Part 1 of the 2 part series

Updated 04/11/2024
Created 02/04/2024
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All morning I had been nervous. No, that's not the word for it. More like absolutely buzzing with excitement, mixed with nervousness. That was more what I was feeling.

We had planned this for months. Mostly due to him having a real busy period with work, and the new college year keeping me rammed with introductory homework after boring essays. But finally. Finally, the stars aligned and I got the text I had been waiting for what felt like an age.

"I'm free this weekend, are you, Baby girl?"

I let out an excited squeak, spinning around in my chair. Kicking my feet, as I re- read his words over and over. Before responding.

Our relationship started, like most, with a chance meeting in a coffee shop. I was catching up on the assigned reading for my English lit course, and had accidentally bumped into him on my way to get a refill. It was so fucking awkward, god I can be so fucking clumsy sometimes. But he was really sweet. Not only offering to buy me a replacement coffee, but to replace my ruined book as well. He would not take no for an answer.

So that's how it started. How John swept into my life. He owned a club, well a few clubs. Some high end fancy cocktail bars and a handful of stylish nightclubs. Although you would have never guessed, with how he dressed. Fine tailored suits that clung to him like a second skin. His salt and peppered black hair was slicked back, and his beard was always neatly trimmed. But it was his eyes that caught hold of my attention. Such a shade of pale blue, I almost mistook them for gray.

After that first meeting, I noticed he had slipped a piece of paper with his number in the new copy of Wuthering Heights he bought for me. Damn if that was not the smoothest thing a guy has done to me.

I took the time carefully picking out my outfit for our meeting. I wanted to look good, but did not want to look too desperate..John had mentioned he liked the fact I didn't dress like most girls at my college. Flaunting themselves off to passing men with their short skirts and low cut tops. "You're for my eyes only." I had gone cherry red at the message.

Finally I decided on a matching set of powder blue lacy bra and panties. A plain white shirt, with long puffy sleeves, and a black plaid knee-length skirt. Alongside some short heels and thigh high black socks. Hopefully I would not get id'd when I went to the club. Even with the cute outfit, my baby face gave my true age of eighteen away. I pinched my cheeks, as I looked at myself over. I was short for my age, around 5ft 2 without the heels. My white shirt clung to my perky C cup tits and narrow waist. Only for my skirt to hug my full hips. I had recently had my hair cut, styling my short Auburn hair with a slight wave. I hoped it would help with my ' not being turned away at the door problem.'

As I made my way to John's club, I felt my stomach flutter with excitement. I was no virgin, but I had a very ... limited experience with sex. When I say I had... limited experience. Well. I had one previous partner. He took my virginity in a quick in out session. No foreplay, no kissing. It was quite unpleasant. So no surprise when he broke up with me not long after. John had not backed away from my lack of experience. Nor had I backed away when he told me he was in his early 40's. There was something about the thought of an older man that made my stomach flutter.

The cab I had booked pulled up outside the club. There were no lights outside, but the long line of people suggested I was in the right place. John had told me to talk to the bouncer, not to line up, and I would be let straight in. I felt bad skipping the queue. Making my way to the tall tough looking bouncer, I felt glares aimed at me, alongside a few muttered curses. The bouncer didn't even ask for my id, simply letting me in once I told him my name.

Inside was not too loud. That was a surprise, the music was loud enough to be enjoyable, but not too loud that you needed to shout over it to be heard. Scanning the room, I could not see John anywhere. Biting my lip slightly, I walked over to the bar and sent him a text to let him know I was here.

"There you are, Baby girl." John's voice drew my attention instantly. Looking up, to find him standing right in front of me. He was so handsome. The black shirt he wore fitted him well, clinging to his wide shoulders and slight build. He had rolled up the sleeves to his elbows. Along with his black slacks and dark leather shoes, he was a breathtaking sight. Did I also mention the man was tall. About 6ft odd, he towers over me when he stands.

"My, my aren't you a delight." His lips twitched into a smile as he held a hand out to me. Taking hold of it, only for him to tug me to my feet and twirl me around slowly.

"Hi" I muttered, feeling my cheeks glow red as he looked me over. Using his hold on my hand, he pulled me so my back was flush against his chest. His hands rested on my hips, holding me in place.

"Now Baby, is that how you greet me?" He purred in my ear, a low rich sound that made my knees weak.

"Hi Daddy." I turned my head slightly, so I did not need to speak loud for him to hear me. Although I was interested in this... dynamic he had brought up, I was still new to it.

"Come with me." John pulled back, taking my hand in his once more, he led me away from the bar. Through a packed dance floor and towards the back of the club. I felt a few eyes flick over me as I followed him, and began to feel a bit self conscious about my outfit. Was it too ... safe. The women we passed were beautiful, dressed in sexy outfits that left nothing to the imagination. And here I was looking like I was going to an office meeting.

A door at the back of the club opened with a soft beep. With his hand firmly on my lower back, John ushered me inside. As it clicked shut behind us, I was greeted by a staircase. Standing at the bottom I felt my stomach do little flips from nerves.

"You ok Baby?" He asked softly, while his hand still rested on my back, he did not force me to start moving. Looking down at me, I could see his gray blue eyes filled with concern. "We don't have to do anything tonight, if you don't want to. We can simply just have a few drinks and relax."

"I want to." I blurted out, looking away in embarrassment. He moved closer, backing me into a wall. Using one arm to block me in place, while his free hand gently took hold of my chin, tilting my face up to meet his eyes.

"My baby is so nervous, isn't she?" He offered me a slight smile as his thumb brushed against my lower lip. I slowly nodded, my brain losing the ability to talk with him so close. The feeling of his warm body against mine. The heady scent of sandalwood and musk that swirled around me, bathing me in his aftershave as he leaned close. I let out a soft moan as his lips finally claimed mine. It was a soft kiss, but I melted into it. Clutching his shirt as I lost myself to him. His beard was surprisingly soft against my skin, it tickled rather than scratched.

As suddenly as it started, he pulled back from the kiss. Earning a low chuckle from him as I whimpered at the loss. "So needy." He brushed his thumb over my heated cheeks. "If you can get up the stairs, I'll give you another kiss, how's that?" I set off up the stairs, hearing him follow close behind.

The door clicked behind us. His office was large. To the left there was a u shaped dark sofa with a floor to ceiling metal pole in the middle of it. To the right a large dark wood desk faced the door. Behind it, large windows looked out over the busy dance floor. The decor was dark and modern, giving the space a classy feel. "Don't worry, no one can see in." He must have seen me eye the windows as we entered. Leaning down he pressed his lips to mine once more, a light quick kiss that left me wanting more.

"Now, I have you all weekend?" John asked as he pulled away.

"Yes Daddy."

"Good." He pulled me against him. "So I have you all to myself. I have some things in mind. Would hearing it help, baby?" I nodded. "Ok, so I am going to take off this absolutely adorable outfit, bend you over my desk and fuck you. Then, I am going to take you to my home, tie you to my bed and keep you there until Monday. You'll go back to school and all you'll be able to think about is how my cock felt in your pretty pussy." He purred in my ear, and I couldn't help but bite my lip at the thought. But my stomach did little flips of anxiety.

"Ok baby." John pulled back, locking me with a concerned look. "I need you to tell me what's going on in that pretty head of yours. We're not going to do anything until you do."

I fidgeted with my fingers as I looked at the desk. I wanted this. Wanted to have him take me. Fuck, it was all I had been thinking about since we started talking about it. But the thought of someone walking past, hearing the weird noises I made. Made me shudder. Hell, I even muffled my cries when I masterbated at home. Even if I was alone.

"Can we.. can we not do the part with the desk?" I turned to look up at him. Wanting to show him how I was up for this. But I was worried he would be disappointed.

"Oh baby.." He let out a low chuckle. "Of course. We do what you're comfortable with. What type of Daddy would I be, if I did not look after my little girl." His lips pressed against my head, and I felt my growing anxiety melt away.

"You're not disappointed?"

"No baby." His large hand trailed down my arm to entwine our fingers together. "So let me take you home, we can fuck on my desk another time."

John..no, Daddy led me out to his car. Making sure to keep a tight hold of my hand, as we walked through the pact club, keeping me close. Sitting in the passenger seat, he had pushed up my skirt, so his large hand rested on my sock clad thigh. I could not help but squirm in my seat, as his thumb drew lazy circles on the soft material, occasionally thumbing the edge of my sock out the way, so he brushed against my skin.

Before I knew it, we were standing in the elevator of a fancy apartment complex. The soft pings of each floor we passed, filled the space. I could feel Daddy's large hand palm my butt casually as we waited for it to stop on his floor. I bit my lip, muffling the soft whimpers at the feel of his hands on my body. When the elevator finally stopped with a soft ping, he kept his hand on my butt, patting it to spur me to move.

His apartment was decorated in the same style of his office. Modern furnishings, metal and exposed brick. Daddy clearly had an aesthetic. "Welcome home, Baby." he murmured into my hair, before stepping further into the living room. Holding a hand out to me, I slipped off my heels, before moving to take his hand. There were large windows that covered the span of one wall, showing a breathtaking view of the city below. "Now before we start playing, what are my rules?"

"Tell you if I'm unhappy with anything. Say 'red' if I want to stop. And n-no hiding." I stuttered on the last rule. I had told Daddy about my habit of muffling my moans, and he wanted to put a stop to that.

"Good girl." His hands took to tugging my shirt from where it was tucked neatly into the waistband of my skirt. "You know what I love about you Baby? How sweet you are. I barely have to touch you, and you get all flustered." His hand lifted my top, pressing his palm the flushed skin he found underneath. I let out a soft gasp at the feel of his hand on my tummy. "I want nothing more than to mold you into the perfect little slut. My perfect sweet little slut. Only for me." I groaned as his hand spanned over my ribs, his thumb brushed against the underside of my bra.

"Do you want that Baby?"

"Yes Daddy. I want..." I paused as he started to slowly undo the buttons of my shirt. "I want to be your slut, Daddy. So bad." My face burned red as I admitted my wants to him. Sometimes I hated how nervous I was around him. I wanted to be the sexy confident woman that should be with him. No this trembling, anxious mess.

Daddy's mouth claimed mine, his hand carding into my hair as he pressed himself flushed against me. I melted into his kiss, standing on my tip-toes as I wrapped my arms around his neck. My first kiss was nothing in comparison to this. A fumbling clumsy thing that left me wondering if these steamy make out sessions were only found in books. I let out a little moan against his lips, only for his tongue to dominate my mouth, brushing against mine. His skilled hand unfastened my skirt, feeling it pool at my feet, I stepped out of it. Reluctantly I pulled back, pushing my now open shirt to join my skirt on the floor.

"You wear this for me, Baby?" Daddy brushed his thumb over my bra strap. He stepped back slightly, taking in the sight of me clad only in my bra, panties and knee highs.

"I brought it for you Daddy. Do you like it?"

"Damn, Baby." He said with a slow exhale. Without warning he took hold of the back of my tights, lifting me off my feet, as if I weighed nothing at all. I let out a little shocked squeak, clutching onto him. With quick long steps, he carried me to his bedroom. The room was decorated in the same style as the rest of the house. A large bed sat in the middle of the room, black bedding spread over it. Gently Daddy lay me down against it. The sheets were buttery soft against my skin.

"Look at you." He groaned, taking a step back to look down at me. "So fucking hot." I watched as he began to undo his shirt, throwing it carelessly behind him.

When he started to unbuckle his belt, I shifted to my knees, reaching out to stop him. "Please." I bit my lip as I looked up at him. "Please let me do this." My hands trembled as I tried to get his belt undone, it took me a little while, but I managed to pull his slacks down his thighs. He did not laugh at my nervousness, simply running a hand gently through my hair. Murmuring soft praises to me.

Once I had freed him from his slacks, and he had kicked off his shoes. He stood In Front of me in just his tight boxers. I could see the outline of his thick long cock straining against the material.

"Daddy.. you're so big." I gasped. I had never seen a cock that big before. I did not know if it would even fit.

"That's because I am a man, Baby girl. You are going to have to learn how to take a real man's cock. Not the little boys' prick you have had before." he smirked down at me as he continued to sooth a hand through my hair. "Now, why don't you take a look."

Taking hold of the soft cotton boxers he wore, I tugged them down slowly. His cock slipped free, bouncing slightly as I pulled away his boxers. It was curved slightly, a thick vein ran along the length of its underside. He was cut, the bulbous head of his cock was flushed with arousal. Reaching a hand out, I could not even close my fist around its thick length. At its base, was a nest of neatly trimmed back hair, that joined the dark trail of hair from his belly button. Looking up at him, I began to slowly stroke my hand up and down the thick, heavy length of him. Daddy let out deep low groans that rumbled out of him. They brushed over my skin and went straight to my core. I could feel my panties growing damp just from the sound of him moaning. Feeling emboldened, I leaned forward and pressed a light kiss to the bulbous head of his shaft. A small bead of pre-cum coated my lips. Licking it off my lips, I was shocked by its taste. Not too unpleasant, but with a slight musky salty -ness to it.

With a gentle tug, Daddy pulled my head away from his cock. "As much as I want nothing more then to fuck your throat baby, tonight's about you. Not me."

"But Daddy." I pouted slightly. I wanted him to feel good too.

He let out a low chuckle, taking hold of his cock in one hand, while the other held my head still. Shifting forwards, he brushed the head of his length against my plush lips. "You like this baby? Like the thought of your Daddy teaching you to suck cock?" I let out a needy moan, as he tapped his cock against my lips. "Don't worry. We'll get there soon. Now." He let go of my hair. "On your back."

Laying back against the sheets, I pressed my thighs together, only for Daddy to press them wide apart, slotting himself between them. "What did I say about hiding?" he tutted, his large hand palming the flesh of my thigh. "Last warning, baby." I nodded, balling the blanket in my fist. His hands roamed over my thighs, sending shivers over my skin where he touched it. I could not help but stifle my moans with my hand, as he brushed his fingers against my panty clad core. "That's it." Daddy let out a rough sigh, pulling away as he rummaged for something. Suddenly he took hold of my hands. Using his belt, he fastened my wrists together, not too tight as to cut off supply. But enough so I could not free myself. Satisfied, he secured my bound wrists to the headboard.

"What did I say about hiding?" Daddy spoke forcefully as he took hold of my chin, forcing me to look at him.

"I'm sorry Daddy." I squirmed under him, worried that I had upset him. My lowered lip began to tremble as I looked up at him. Damn it, why did I have to go and fuck this up.

"Color, Baby girl?" The question snapped me out of my growing panic.

"O-orange." I stammered out after a short pause.

"It's ok." He cooed, taking to soothing his hand through my hair again. "Remember I warned you, that if you broke my rules, you would be punished." His voice was so soft as he spoke, easing my anxiety even more. "I didn't mean to scare you, Baby."

"It's ok." I leaned into his touch as much as I could. "Can we.. Can we continue? Please Daddy."

"Color?"

"Green" His lips spread into a wide smile, before he leaned down to press his lips against mine. Slowly, he trailed sweet kisses down my neck. His hands pulled down the cups of my bra, baring my perky breasts to his hungry gaze.

"Such pretty tits." He spoke into the flesh of my breast, before biting it gently. Palming my other one with his free hand. His hand was so large it engulfed my whole tit. I was always self conscious about how small they were, but all of that flew out the window as Daddy fastened his mouth around my rose pink nipple, sucking it, and swirling his tongue around the stiffening peek. While his over hand, took too teasing its twin into a little pebble with his skilled fingers. I could not take it, not being able to touch him. Arching myself into him, I let out breathy moans at the new sensation.

"Daddy." I whimpered. Looking up at me with my nipple still in his mouth, he let it go with a pop. Before taking to press more kisses down my chest, heading over my tummy. He bit lightly at my hip. Catching me with his wicked gaze, he bit down slightly harder. Sucking at my skin as he did. When he pulled away, there was a small love bite left behind. His beard tickled my skin, as he moved closer and closer to my core.

"Do you have stockings?" Daddy asked, as he ran his hand over my thigh highs.

"N-no I don't."

He let out a soft hmm. "I'm going to buy you some lingerie. Have it sent over to your dorm." He bent close, pressing his lips to my thigh. "Would you let me do that? Treat you like my little princess."

With my arms still bound above my head, I could not hide my blushing face from him. "Yes, Daddy. I want you to spoil me." I mutter, earning a low chuckle from him.

"Oh sweet Girl. You know I love nothing more than the thought of spoiling you." He paused, pressing another kiss into my thigh, a little higher than the last. "Of showing you how you should be treated." Another kiss, this time where my thigh joined my crotch. "Of making you happy." The next kiss was placed on the skin of my lower tummy, just above my panties. Looking up at me, through hooded eyes, he slowly kissed my panty covered core.

He quickly pulled my panties off, when I arched my hips towards his lips. Burying his face back between my legs. The low groan Daddy let out went straight through me. "Fuck, baby. Your pussy tastes so sweet." He took his time, lapping along the length of my core, before circling his tongue around my clit. His large hands took hold of my bucking hips, draping my thighs over his shoulders, he held one in place. His free hand took to joining his hungry mouth. Teasing against my slick lower lips, then one finger slid inside my core.

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