Many people say that winning the lottery is the worst thing that could ever happen to you; murder and an early grave seemingly an unavoidable aspect of the prize. As I sat in my Honolulu penthouse looking out over the beautiful Ala Moana beach to my south and the Waikiki skyline to the east, I couldn’t help but laugh at the notion that I had been unlucky. 

Gone was the stress of “how was I to afford a home?” Gone too were the thoughts about how I would always be alone because I couldn’t even earn enough to go on dates, let alone the sad prospects of me actually getting one. No, the idea that the worst moment of my life was when I looked down at that lottery ticket and saw all of those beautiful matching numbers was preposterous.

To be fair, I didn’t completely discount the worries of what winning the lottery could mean. I was in my new attorney’s office the very next morning and an accountant’s office that afternoon. A little under three months later, my winnings were deposited in a trust and the keys to my brand new fully furnished penthouse in Honolulu were in my hands.

Grinning at the absurdity of it all, my thoughts turned towards that night. After taking a few days to settle in, I had finally signed back up on the dating apps. My pictures were unchanged from the profiles that delivered so little prior success, but my new bio had scored me a dinner date with a 24 year old surfer-chick named Sky. Funny how much less popular the standard “Looking for a real connection, not just a one-time thing,” is than just saying that you’re, “Looking for someone to spoil in exchange for some fun.” Subtle it was not, but subtlety was not in my plans for anyone honest enough about their intentions to respond approvingly. 

Our meeting place was an upscale seafood place just across the street from my building that seemed to get Sky excited when I suggested it for our first date. Before heading down, I did one last check to make sure that everything was in place for later; the underbed restraints were secure, the toys were all organized, and Sky’s gift bag was ready. Feeling confident, I stepped in the elevator and walked over. 

Walking into the restaurant, I laid eyes on its gorgeous maitre d’. Perhaps it was just my overconfidence, but I could have sworn that her face betrayed a quick blush before her greeting met my ears. Smiling, I confirmed my reservation and requested to be sat at an open table near a window looking out at my building. The maitre d’ - her name was Kate, was happy to oblige and the thoughts that passed through my mind as she walked back to the front got my blood pumping. 

As I began to settle down, I was met with Kate’s face once again, this time blushing uncontrollably. The reason was made clear as soon as she stepped to the side; Sky’s choice of clothing made it apparent that she likewise shared an aversion to subtlety tonight. 

Every bit of the 5’10 her profile promised, her tanned athletic figure was draped with the skimpiest black mini-dress my eyes had ever seen. From the front, a thin halter neck strap gave way to a criss-crossing design at her bust, displaying her ample cleavage. Moving downwards, the black dress clung to her sides, connected by a strip of fabric just above her hips, framing her visible toned abs perfectly. The most astonishing sight was that of her legs nearly fully visible up to the hip thanks to slits on both sides - each step carrying a suggestion that perhaps its successor wouldn’t be quite as successful at obscuring everything from view. From the looks on those behind her, I could only imagine what the view from behind looked like. 

Quickly standing up as Kate pulled out the chair opposite me, I reached out for a quick hug to greet Sky and was met with a full embrace - my excitement quickly turning to arousal as she pulled her hips aggressively into mine. As we moved to sit down, I was thankful that all eyes were still on Sky as my own choice of clothing was locked in its own struggle to obscure my arousal from view. 

As she took her leave, Kate gave me a chuckle and wished us both a wonderful meal. Smiling now across at Sky, I complimented her on her outfit, joking that she was liable to give some of the older guests a heart attack due to how stunning she looked. Her playful thanks were followed by her own compliments - she loved my short hair and apparently my time in the gym was paying off as she excitedly commented on how much more muscular I looked in person than in my photos. 

Over drinks and dinner, I learned that Sky had moved to Hawaii from a smaller city in Southern California to study marine biology. Following graduation, she had balked at the idea of leaving the islands for additional years in graduate school, so decided to pick up a job as a surf instructor and part-time model to stay in Honolulu instead. Her eventual dream was to save up enough money to purchase a boat and equipment to support a social media channel where she planned to explore the marine life surrounding the Hawaiian islands, but she still had a ways to go before her savings outran reality. 

I told her that I had just recently moved to the islands all the way from Florida where I’d lived for years. That in the past, I had waited around for life to happen, but that moving to Hawaii felt like a new beginning - one where I am not going to wait to do the things that I want to do. I could sense her approval at this and all doubt was removed as I felt her foot softly brush against the inside of my knee. She smiled and asked what plans I had for her after dinner?

Shrugging, I suggested that we play a game up in my condo - the winner chooses our next date. Sky laughed and asked what games I had and how far away? I told her that I had a few board games and some other options if she was interested - for the second question, I pointed across the street and up to the top of my building. Her foot sneaking slightly further up my thigh was her answer. 

After paying our bill, we stood up and I was met with the backside view of Sky’s mini-dress for the first time. I fully understood what everyone had been looking at. Her halter neck left her toned back fully bared and each step threatened to partially unveil the hottest ass I had ever seen; clearly, a lifetime of surfing and swimming had been kind to her. As Sky led me past the front of the restaurant, Kate thanked us for joining, wishing us a quick return, and a wonderful night. I thanked her in turn and could’ve sworn that I saw her blush again before Sky pulled me through the doors and out onto the street. 

Looking up, she asked me to point to which floor my condo was on; standing behind her, I wrapped her right hand in mine and pulled her arm up to point towards the top floor as I draped my left hand on her left hip. As I did so, I felt her take a half-step backwards so that her ass was firmly against my waist and with a slight turn of her head to the side, asked whether I was ready to show her the inside? 

Just as I began to move in for a kiss, she laughed and stepped forward, dragging me across the street. Walking past the security desk, I caught the guard staring at Sky’s outfit and laughed to myself about who could blame him? As the elevator doors closed and we began our journey up, Sky asked whether I had decided on a game? I said that I had a few ideas - was she interested in a board game or something more active? A kid’s game or an adult game? Before she could respond, the doors opened and we walked into my private foyer. While I opened the door into my penthouse, “Your choice. I will tell you if I want to do something else,” was Sky’s response as she walked inside. 

I invited her to look around while I freshened up and thought about our game and steered her towards the main living room where the best views were located. While I walked towards the bathroom just off the kitchen, I could sense her amazement. As I walked back out to find Sky and start the fun, she was gone - or at least I thought she was. On the kitchen counter was a small note with the words, “Hide & Seek - find me within 3 minutes of reading this note and you win.”

As drop-dead sexy as Sky is, I was beginning to like her personality even more. Smiling, I called out that I am beginning the timer, setting my Iphone timer to 3 minutes and beginning to search for her. 

First, I did a quick round through the kitchen - checking the pantry and around the separate bar area. Nothing. There was nowhere to hide in the main living area where I’d last seen her, so I next moved towards the entertainment room just off the living area. No sign again. A full minute had elapsed. Moving across the entertainment room and into the first guest room (which I’m planning on converting to an office), I looked in the bathroom, closet, and under the bed. Still nothing. It’s the same story in the next guest room and the laundry room. Looking at the timer, there's only 30 seconds left. Starting to worry, I quickly think where she might have hid - maybe laying down in the tub in the master bedroom? Hoping beyond hope that I’m right, I rushed back to my bedroom, seeing only 15 seconds left. Bursting in, I’m met with gleeful laughter as Sky shouts “You found me!” while excitedly jumping up and down near the foot of my bed. 

As the timer goes off, I stop it and put my phone on the table without taking my eyes off her - the partial light from the hallway somehow elevates her silhouette even more than before. My body immediately signals its agreement as my pants get noticeably tighter. Sky stops jumping as we lock eyes, her grin softening as she glances downwards before quickly meeting my gaze again. 

While moving closer towards her, I tell her that I want to claim my prize for winning - that our second date will begin now. Responding in a notably huskier voice than before, she asks what we’re going to do on our second date? Stepping past her to the right side of my bed, I remove the under bed restraints from their hiding places. Passing her while I move to reveal the right side restraints, I take her hand and pull her with me, letting her watch as the final restraints are shown. A small gasp escapes her and I turn around, quoting her earlier statement that, “We are going to do whatever I choose to do unless you tell me otherwise.” 

A small tremor moves down her body as she nods her head in agreement. I pull her into me as if to go for a kiss and find her ready to return in kind. At the last moment, I pull away and go to the drawer where my toys are stored, pulling out a blindfold, vibrator, and paddle. Turning back towards her, her eyes are wide with anticipation. 

I spin her around as I reach her, dropping the toys on the bed so that she is facing them. Stepping directly behind her, I use my left hand once more to grasp her hip as my right moves further up to her right breast, using both to pull her against me as I nibble softly on her right ear, whispering that I can’t wait to use my toys on her. Another full body tremor betrays her excitement as I move my right hand across her chest to her left breast and squeeze as my left hand reaches down inside the slit in her dress at the hip and across to her panties. Now, it’s my body’s turn to betray my excitement as Sky begins moving her hips slowly against my pants while she turns her head to the right and our lips passionately meet. Slight moans escape both of us as my hands explore her body and her ass teases mine. 

Spinning her around face to face, she steps aggressively into me and restarts our passionate kissing while my hands slip up underneath her dress and grasp both sides of her tight ass. As my pants begin to get uncomfortably tight, I move my hands back up, slipping them first up her hip and side, until they’re on either shoulder. I pull my face away from hers and lock eyes as I push her shoulders down, forcing her to kneel down in front of me. Sky immediately begins to kiss the outline of my cock while her hands run up and down my legs, snaking behind to grab my ass. As I begin to moan, she slips both hands back between my legs, making sure that I can feel her fingers moving underneath my crotch and towards my front.She quickly undoes my pant’s button and slowly pulls down the zipper. 

As she begins pulling down my pants entirely, she looks up and makes eye contact with me and smiles, then turns back down and stares at my cock as she pulls down my briefs. Slowly, Sky’s mouth envelops my cock as I try to untangle my feet out of my pants and lift off my shirt. A soft moan escapes me as she slowly begins moving her mouth back and forth, one hand moving underneath my balls to cradle them while the other takes turns finding more handfuls of my ass or rubbing my chest. Waves of pleasure begin washing over me as her tongue teases while her mouth remains sealed over my cock. I move my left hand to the back of her head and grab a handful of her blonde hair while the right sneaks down to grab a handful of her opposite breast; her moan nearly matches mine as I give a gentle squeeze - whether caused by having her hair or her breast grabbed escapes me. 

As I feel I’m getting closer, I use my handful of her hair to pull her head backwards and off my cock and gently pull her hair down so that she’s forced to look up at me. Slowly, I pull her up so that she’s back on her feet and begin to forcefully kiss her, keeping my left hand full of her hair while the right desperately slides all over her body until I get too frustrated by her dress. Without warning, I let go of her hair and pull my lips off hers, bending down so that my face is even with the bottom of her dress and using both hands, I lift her dress up and over her head, throwing it on the floor. Kneeling back down with my face now eye level with her exposed panties, I tease her pussy with a kiss through the fabric, earning a small moan, before pulling them down and discarding them near her dress. 

Immediately, my left hand moves behind her hip to squeeze her ass as my mouth and right hand simultaneously find her pussy and left breast respectively. Her body tremors again as my tongue traces an outline along her labia. She’s soaking wet and tastes wonderful - slightly sweet and moans approvingly when I tell her so. My tongue moves to the back of her vagina and I take one slow, long lick up to her clit, soaking up as much of her wetness as I can. My mouth then moves to create a small suction over her clit while I use my tongue to begin teasing her. My hands switch positions, with my right now squeezing her ass from underneath her leg rather than around her hip, giving me better access to slide it teasingly underneath her. 

As my tongue adopts more intention, I can feel her body beginning to tighten as an orgasm builds within her. Staring up at Sky from my knees, I see that her eyes are closed and her head is slightly tilted upwards to the side; knowing that I’m getting closer, I turn back down and begin rhythmically licking her clit, up and down, over and over. As I feel her body tighten more, I feel her hand aggressively reach down for my hair as she grabs a handful for stability while beginning to grind her pussy back and forth over my mouth. It takes all of my jaw strength to keep my mouth positioned right over her clit and my tongue on the same rhythm as she moves herself faster and faster against me while her body continues to tighten. Suddenly, just before it feels as if she is about to snap, uncontrollable waves of pleasure crash across her body and her moans threaten to wake my downstairs neighbor. 

Her grip on my hair is now all that is keeping her standing as I continue pressing my mouth against her and my tongue remains on the same rhythmic flicking against her clit. As I feel a new set of waves crashing over her, her grip on my hair loosens and I can feel her starting to stumble backwards. Quickly standing up with my arms around her back to brace her, I pull her naked body against mine and give her a kiss as she melts into me. As the waves begin to subside across her body, I trace one hand back down to her pussy and softly feel her warmth and wetness with my pointer and middle fingers before bringing one finger to my mouth and sucking her juices while she looks on and inviting her to do the same from the other as I look into her eyes. 

Popping my finger out of her mouth, she looks hungrily at me and asks, “What’s next?”