First Time, First Play – Abroad

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Meeting up for the very first time and a once in a life time trip…

I am a lover of Art. Ever since childhood, I have always seen things from a creative eye, and naturally excelled in anything that required a creative force. When I would draw or paint, I had to feel the emotion of the topic before I could put anything down on canvas. For some people, it could be “how light hits…” or “the color of it does this or that etc.,” but for me, there had to be something that stood out special or sparked an emotion, similar to the method of the famous American Artist, Andrew Wyeth.

When I was 18, my mother would not let me attend my senior prom and so, I ‘acted out’ by creating a prom dress collage-like mural of a girl showing up at her prom, wearing a shocking strapless dress made up of a sea of faces of pretty models and prom dresses, permanently glued to one bedroom wall! My mother was livid!

Anyway, back to the story…

It wasn’t long ago that in the location that we chose for our first meeting or play session for the first time, many of the local Capetonians steered clear of the city’s Victoria & Alfred Waterfront and surrounding shore. The area was known as both an industrial shipping hub and a tourist magnet, dealing in knick-knacks and sightseeing cruises.

That perception changed however, when the Zeitz Museum of Contemporary Art Africa opened in late 2017, in a former grain feed storage, which was redesigned by the famous London architect named Tom Heather-wick. The museum holds one of the world’s largest collections of contemporary African art, much of it from the personal holdings of Jochen Zeitz, the former CEO of Puma. The artwork is just breathtaking!

The hotel we settled on was the new 28-room Silo Hotel, which sits on top of seven floors of the Zeitz Museum of Contemporary Art Africa.

It had bright, lofty rooms, with plush furnishings, crystal chandeliers, and separate lounge areas— with pillowed glass windows that gave the rooms a futuristic note. We booked our own hotel rooms because for me, it would be somewhere to retreat to if necessary. I will also need to unwind, take off the “mask” and just be myself -not his sub.

While heading to up his room and stepping off the elevator, I was just in a daze or in like a dream with a rope tied around me, pulling me forward with each step. I passed by others completely unaware as I counted room numbers until I arrived at his door and knocked.

He answered the door with a smile.

“Hello. Please come in,” he said and then stepped back into the center of the room, giving me a wide berth to enter.

“Hello Nicholas,” I said in a weak voice before clearing my throat. And after a pause, I stepped over the threshold and closed the door behind me. The hotel room felt warm. It was one of those large posh ones, with a sunken seating area, a large flat screen TV, stocked minibar, a bathroom to one side and a lovely large bed, in a separate room. (His room was better than mine. Darn it!) Here I am, finally facing the most sensual, tantalizing, and intellectually exciting man, walking the earth at the moment.

My mouth went dry and I pasted on a smile, but my heart started to pound like it was about to jump out of my chest! I felt like I couldn’t breathe suddenly from the grips of nervousness engulfing me.

He was even more attractive in person, with this incredibly disarming smile that started to have a positive effect as I stood leaning against the door, just staring at him. I have not stood in front of another man like this, in over ten years. I was somewhere in between fear and utter exhilaration! He was wearing a dress shirt and dark suit pants, all neatly pressed.

The collar of his shirt was unbuttoned and I could see his skin and this made me sigh slightly. His dark hair looked damp and slicked back, most likely from a recent shower and I could smell a hint of mint shaving gel and Acqua Di Gio cologne.

My eyes lingered and settled on the leather belt at his waist. He continued to smile, studying me, while I checked him out, but remained silent. Maybe he sensed my inner turmoil, and wanted to give me time to calm down and present myself to him willingly, – rather than in a ball of anxiety. I know that he will want me calm, uninhibited, confident, relaxed, focused, and ready for his use.

“Before we begin, um …anything, may I use your bathroom?” I asked nervously.

He put his hands in his pants pockets, never braking eye contact with mine and said, “Sure,” and nodded toward the direction of a door toward my right.

I practically ran into the bathroom, locking the door behind me. “Shit! I must look like a really silly girl! OMG! I can’t believe that I am even here -with him! I have to get myself together!”

I closed my eyes and took a deep breath to try and calm my nerves. I listened for sound, any sound coming from the room, but there was none. I opened my eyes and looked in the mirror to check my makeup.

I checked my shoulder bag to make sure that I had packed everything that I was supposed to bring with me; a few flavored condoms, mints and chewing gum, a white wash cloth, two cherry flavored tootsie roll pops, my black eye mask, hand sanitizer, a (Daddy selected) bottle of anal lube, package of wipes, one white envelope. I removed the black eye mask and tied it in place. I placed a piece of gum in my mouth, took a deep breath, turned to face the door, opened it and walk back out into the room. Daddy was still standing in the same spot with his hands still in his pockets, waiting for me.

He raised one eye brow at my eye mask, but other than that, did not seem moved or bothered at all, by my weird behavior.

I blushed at the thought of how ridiculous I must have looked and a shy smile formed across my lips, as I met his eyes, “Um, I-I am sorry for the delay. I am extremely nervous. Please understand.”

Both his eyebrows lifted after my last statement and he says,

“You forgot something. Please understand -What?”

His face was serious, his smile was gone, and my knees suddenly went weak.

I cleared my throat before responding, “Sorry. Please understand, Sir.”

His smile returns, then he walked toward me and held out his right hand.

“Come here, Sharry.”

I took a deep breath and walked slowly toward him and placed a hand into his. He took a firm grip and I felt him pull me slightly toward him. I followed his lead, and as I came closer, Sir examined my face, before lifting my hand up to kiss it. The touch of his hand and his soft lips on my skin, caused an involuntary small intake of breath on my part, and I looked away slightly to hide my blush, as a small shiver ran up the back of my spine.

“Sit down here” he said and motioned to a set of chairs situated in a seating area.

“Now I need you to listen to me. As much as I want to rip your clothes off right now, I am a man of some self-control, and I want to make sure that you feel comfortable.”

It had been 13 months of LDR in messages, webcams, LDR toys, and Skyping online, and this was our first ‘in-person’ playtime session. He did not let my hand go, and started circling the back of it with his thumb. I also noticed the ‘vice-like’ grip on the armrest with his other hand, as he seemed to strain for self-control. If the armrest was made of glass, it would have shattered under the white-knuckle grip that I could see through his white skin! Seeing this impressed me, and helped me to relax a little. Sure, I could run from this room out of fear and never look back, but I really don’t want to because my need for him has become physically, emotionally, and mentally overpowering.

Should I be worried? I mean, I have never done this before, and he could be some kind of serial killer or rapist who selectively, strategically, and methodically, lures his willing prey into his domain, only to rape, beat and destroy! I am not here for that. No. I am not here for pain, but pleasure. Yes, I am here for the over-powering part, yes, to capitalize on my adventurous spirit, and use it to guide me places unknown to my inner slut. Yes! To cultivate the inner naught, that so wants to be released – but safely and in compassion – with caring ownership and guidance. Not to be slapped with a harsh hand, but instead, affectionately with a huge cock. I want to be used as a fuck toy, and not to be used as a punching bag! To be taken by force AT my will, not against my will. I want to release screams in the grips of passion, not in crippling torment. I want to quiver in admiration, wanton-passion, and respect -not in terror.

I am not a foolish girl. I don’t want to be tracked or stalked like prey -who wants that? I am more along the lines of a totally depraved hungry slut, trapped and hidden behind a conservative wall with no door, and suffer with NO intellectual or physical challenge –screaming for a passionate release!

I settled back into the chair and I searched his face for his seriousness, while my heart pounded like a drum in my chest as the effect of the movement with his thumb, started to create a warming sensation between my thighs! I was here now, and there was no turning back from this or from him -not now.

I smiled at him, pulled my hand away, swallowed nervously, took a deep breath, got up from the chair and stood in front of him. Both the desired and dreaded moment was finally here…

“I am ready.”

And with that, I unfastened my black trench coach and let it fall to the floor, revealing my black corset, black lacy gloves, black garter belt with stockings, and a black thong.

I expected him to jump on me right then and there, but instead, he took a moment, letting his eyes wonder the length of my body, exhaled, before settling back on my face. His facial expression was serious, as he studied my face for a long moment, before standing up. He did not say anything, took a step toward me, and snaked his hands around my waist, tugged me toward him, and slowly leaned in and pressed his lips to mine, starting a very passionate kiss. The smell of him engulfed my senses, as his lips and tongue made love to mine. Soft moans escaped me unconsciously, as he molded my body to his, his hands explored my body, gripping my ass hard, before sliding his hands up in front, to cup both my breasts.

His lips devoured mine with a smoldering hunger, which was over a year in the making. A whimper escaped me as I braced myself for more of his ‘kissing assault’, by resting my palms against his chest. Daddy’s tongue sought mine, as he deepen this passionate kiss and the mere intimacy of it, caused a spark of pure unadulterated hunger, to ignite in me. I wanted this man so terribly that I could barely maintain my own balance, while wrapped in his embrace.

This strong desire forced a little of my hidden boldness to surface, and I strengthen my efforts by kissing him back, eagerly exploring his mouth with my tongue, while my fingers trailed to the nape of his neck. He was taller than I was and so his rock hard cock pressed into my tummy, just below my belly button, as he let out what sounded like a growl, and I felt his muscles twitch under my fingertips, as I threaded the hair at the nape of his neck, while wrapping one leg around him for support.

His fingertips traced a fiery path up the back of my neck until they were intertwined in the strands of my braided hair.

Soon Daddy slowed the kiss and I moaned and gasped for air, when he finally tore his lips away.

He then kissed along my jaw line, trailed his tongue to my neck before nipping my right earlobe with his teeth and whispering,

“You are such a lovely girl and I have been waiting to do that for a very long time but damn, I want to fuck you right now and I cannot, no, I will not wait any longer.”

His words rough with bridled lust, as he ran a hand up my inner thigh, cupping my soaking wet pussy, and I almost fainted!

“Mmmmmm, something is really ready for me…”

My breath got caught in my throat and I struggled to swallow and gain composure, as Daddy released me. (Only then did I notice that my chewing gum was gone -and I did not swallow it!)

“Now, please go to the bed.”

My breathing was still trying to return to normal, as I turned my attention toward the direction of the bed.

“Did you bring everything that I asked for?”


“Yes, what?” he asked.

“Yes, Sir” I responded in half a whisper and half a whimper.

“Good girl. Now, go and stand in front of the bed and wait.” I slowly walked over and stood at the front of the bed as my heart began to pound madly in my chest. Daddy walked over to where my bag was next to the chair, and pulled out the special brand of lube that he had requested I bring and tossed it on the bed.

I closed my eyes as Sir walked toward me, while starting to unbutton his shirt and with his next statement, proved to me that he was not to be one who plays games, when he said…

“We are about to ‘break the ice’, baby girl.”

My eyes shot open wide in surprise! I turned to look at him, but his facial expression was serious. He was not joking.

He was actually serious about, for our first time together, fucking me in the ass! My inner response was, “Wait a minute! You want to do THAT and for our first time? OMG, what have I gotten myself into?!”

I didn’t know if I should feel irked because he did not want my pussy first or excitedly impressed at his ‘thinking outside of the box.’

“Sir, are you serious?” I asked. “This is our first time.”

He remained silent and left me waiting, while he removed his shirt, cuff links, watch, and suit pants and placed them folded neatly on a nearby chair.

“Yes I am, and remember, it was originally your idea.”

He was referring to a brief comment that I made almost a year ago, when we were discussing the strong possibility of me experiencing extreme nervousness during our first play session, and I nonchalantly recommended that he ‘break the ice’ by fucking me in the ass – right out the gate!

But I did not mean for him to take me literally!

Sir stood behind me and ran his hands up my body, cupped my breasts and pulled me backward into his embrace, while kissing the right side of my neck. I started to moan as he skillfully squeezed my breasts and needed my nipples until they were stiff points. He rolled my nipples between his thumbs and forefingers, causing waves of pleasure to shoot through my body!

I reached up behind me to put my fingers in his hair as encouragement, and Daddy ran one hand down to my upper thigh and squeezed.

“Lay on the bed face down please.”

“Yes Sir.” I said breathlessly, as I leaned forward out of the circle of his embrace, and onto his bed.

Sir climbed onto the bed, but surprisingly, sat beside me, looking down at me. “Dadd-” I started, but he raised a hand signaling for me to stop and then said, “SHHH. I just want to make sure that you are relaxed.”

And with that, he leaned over and started to massage my shoulders and back, to my otter amazement! At first I stiffened under his surprising touch, but then relaxed into the warmth of his hands and the pleasure of his skilled touch on my back. It really felt amazing because I was quite tense!

After a while, he said “Now, baby girl, could you turn over. I want to see you.”

As I slowly, started to turn over and Daddy suddenly slapped my right ass cheek! I yelped in surprise, and hurriedly turned over onto my back.

“You were not moving fast enough,” He said with a wicked smile, now standing at the edge of the bed, looking down at me.

After a moment or two, Daddy leaned forward, grabbed both of my ankles and pulled me down to the edge of the bed. He reached up and practically ripped my panties off, before lifting my legs up to rest against both of his shoulders. Apparently, he was not planning on wasting anymore time…

“I will be keeping these so don’t try to put them back on…” he said.

He stroked his delicious cock, before ripping open a condom packet with his teeth, and then slipping it on.

“As you wish, Sir,” I smiled, noticing the near perfect height of the bed, as he looked down and began to rub his already steel-hard cock, up and down my soaking wet pussy, letting my juices help lubricate him. He then leaned over and picked up the bottle of lube that was already on the bed, and squeezed some onto his cock and then squeezed some into his hand, which he then rubbed between my parted ass cheeks and around its puckered entrance. The lube felt cool against my skin but not uncomfortable or distracting. My heart was pounding so loud that I could hardly hear anything, as the time had come!

Daddy had given me training anal plugs and beads to use over the several months, in preparation to prepare me for anal sex, since I was a newbie to anal sex.

Daddy loved big breasts and a nice full ass, and was definitely a “Tits and Ass’ kind of guy. My body was shaped like a ‘back-in-the-day’ Coca-Cola bottle, with 38K sized breasts -and I was also an ‘Anal Virgin’ with an adventurous spirit. Perfect!

Sir bent my legs a bit, so that he could spread my cheeks and slid his cock down to the puckered entrance of my ass, and then slowly started to push the head of his cock, through the tight opening. I inhaled and then gasped against a quick, sharp pain and then pressure, before closing my eyes. I believed that if he had not instructed me to practice with various anal plugs, I would have screamed. His cock was much bigger than any of the training anal plugs that I had been practicing with. Sir let out a deep gasp, as he slowly continued to push his cock in and paused when his head was completely inside.

“Are you okay?” “Do you want me to stop, sweet girl?”

“NO!” I partly gasped – partly yelled in response. I started to enjoy the wide stretched feeling of impalement that his cock gave me, as he slowly pushed his cock in deeper, but with small retreats, as my muscles gave way to his invasion.


“OH G-”

“Uh…Ah…OH…OH…OOOOH…Mmmmmmm,” I moaned and groaned continuously, as he continued to, slowly and steadily, pull in and out, invading my anal cavity further and further each time, until his thick cock was finally deep inside me, and I bit my lip upon his final thrust forward!

“Mmmmmmm, god baby girl, you feel amazing,”

He completely filled me. I flexed my anal muscles, around him, feeling his warmth and hardness. I was surprised. It felt really, really good and I liked how deep he was inside my body. It was so different but yet still intimate and pleasurable.

Sir sure seemed to know a great deal about anal sex. I knew that it wasn’t quite like intercourse, since he wasn’t thrusting in and out, as fast and furious, as one expects during vaginal sex. I started to savor the slow back and forth motion, as his cock only moved a couple of inches in and out of my sensitive rectum, as he started again. The clasping, overstretched ring of my ass, slid slightly in and out around his cock as he fucked me. And all the while, I squeezed and clenched my ass around him, sending ripples of pleasure through us both, as my ass muscles applied steady even waves of squeezing power all along his cock, as he inched in more. I had tried to read up on the topic and watched several porn videos on what to do, so that I could be pleasing to him somehow.

“Mmmmmmm…” “YESSSSS…” Sir moaned, as he started to move, pulling slowly out, leaving his head embedded, before reinserting his cock all the way in.

As Sir pulled out again, he paused and with a serious expression, asked, “Baby? Do you remember your safe word?”

I nodded and gasped “Yes, Sir, Yes!”

“Good, because this is for me-” and Sir thrusted his cock all the way inside me! I responded in a single high pitched Yelp, in surprise. Sir leaned forward on both hands and began to thrust in and out faster, moaning each time. I squeezed his cock a few times, without realizing it and he seemed to like it, “Mmmmmm, baby, your ass is wonderful!” he groaned, as I began to enjoy the feeling of his large cock moving inside me. Sir began to move faster and my moaning increased, and I had to grab hold of the head board to steady myself, has his thrusts increased until he let out a long primal moan, more like a roar, as I felt him explode inside me. Sir slowed down, pulled out and collapsed on top of me, between my legs, with his face buried in my neck, breathing heavily. “Mmmmmm. Fantastic.”

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