Part 1

“What’s next?” I repeated as if it was truly a question. After taking a long look up and down Sky’s body, I said, “get my paddle from on the bed and hand it to me.” Sky’s eyes got wide as she bit her lip ever so slightly. “Yes Sir,” was her response. As she turned towards the bed to grab my paddle, I looked down at her beautiful heart-shaped ass and slid my hand between her legs, gliding my fingers through her soaking wet pussy, earning a small gasp from Sky.

She began to turn around, paddle in hand, so I sat down on the bed and ordered her to hand me the paddle and then lay across on her stomach. As she did so, Sky made sure to slide her breasts over my dick, grinning, “Yes Sir.”

I had played games like this before, but never with a woman as sexy as Sky - her submission turning me on in a primal way I had never experienced. I had only been wealthy a short time and already the returns were seemingly beyond my wildest dreams.

Returning to the moment, I said, “We’re going to play another game - Truth or Spank. I am going to ask you a question, and you can choose whether to answer the question truthfully, or be spanked. I will then repeat the question; if you again refrain from answering, I will spank you as many times as I desire. Upon your answer, I will stop immediately. Do you understand?”

Sky turned her head toward me, her wide eyes communicating a mix of fear, excitement, and arousal, and said, “Yes Sir.”

“Ok, we’ll start with something easy. Do you like being spanked?”

“Yes Sir.”

“How hard?” I asked.

Smack.

“How hard?” I repeated.

Smack. Smack. Smack! Smack! Smack!

As I reared back for one more, Sky turned her head back toward me with a sly smile and said, “As hard as you want, Sir.” I could feel the blood rushing away from my head as she did.

“Good girl,” I nodded. “Do you like having your hair pulled?”

“Yes.”

“Do you like being fucked roughly?”

Smack!!

I could tell this one had left more of an impression as Sky let out a gasp while her back arched involuntarily. “Do you like being fucked roughly?” I repeated. “Yes Sir!” she moaned.

“Why did you match with me and agree to a date?” I was curious about this - was she only in it for financial reasons or was there something more sexual behind her intentions?

SMACK!!!

“Why did you match with me and agree to a date?” I asked again, more forcefully, her leg twitching while I stared at her increasingly reddening ass.

“I thought you looked cute and got turned on by the idea of having a sugar daddy that would use me in exchange for their pleasure.”

Her answer excited me. "Have you ever been with a woman?”

“Yes.”

“Have you ever done anal?”

“Kinda?”

“Kinda is not an answer.” Smack. “Have you ever done anal?

Sky’s grimace betrayed how much of a toll her ass was beginning to take. “I’ve only been fingered, but have both rimmed out someone and been rimmed out by someone.”

“Good girl. We’re almost done. What is the sluttiest thing you have done, Sky?”

I tried to hide my genuine surprise as she answered that she had sucked off a college professor for a better grade. “Have you ever done anything like this before?”

“No Sir.”

“Are you ready to proceed?” The silence that followed surprised and then worried me. Had I pushed too far already?

Smack.

“Are you ready to proceed?” I asked again. The silence now broken only by the sound of my heart beating, I brought my hand back, the paddle glaring menacingly at Sky’s tanned ass now tattooed with red. Sky took a deep breath.

Smack. Smack! Smack!! SMACK! SMACK!!

Sky’s legs began trembling uncontrollably as her back arched once more as she let out a long, loud moan of pleasure. The intensity of her reaction surprised me - I had thought she was reaching the end of her rope, but instead she had been getting off on it. As her body calmed down, she turned towards me, whispering “Yes Sir,” before pulling in for a passionate kiss.

This chick was nuts - in a good way. Sliding out from underneath her, I stood up and looked down as she shifted onto the bed, staring up at me expectantly. Taking a deep breath, I reached my hand towards her face, softly caressing her right cheek, my smile returned in kind. “Lay backwards,” I told her. “We’re going to see how strong these restraints are,” I laughed.

Her eyes growing wide again, she scooted her ass backwards on the bed as I began securing her ankles. As I did so, Sky secured her left wrist, leaving only her right arm free. I slid up on the bed, taking care to slowly kiss her legs up towards her pussy - her moans increasing as I got closer. After a few kisses alongside her labia, she began shifting her legs against the restraints in anticipation. Glancing up at her, I saw that she was staring down at me with hopeful eyes.

One long, deep lick of her pussy and the extreme state of her arousal was undeniable. Her back arched upwards as my tongue brushed against her clit, her gorgeous breasts reaching for the ceiling. But instead of continuing to pleasure her clit, my tongue slid upwards towards her stomach and to her breasts.

As my tongue began to play with her rock-hard nipples, my left hand moved to secure her right wrist, completing her helplessness. Her moans of pleasure intensified as my hands began rubbing her breasts while my tongue continued teasing her nipples; my right hand slipping down towards her pussy - and feeling how soaking wet she is - began rubbing her clit too. As I felt her body begin to tighten in anticipation of another orgasm, I slid off to her frustrated shock and reached for the blindfold and vibrator. Securing the blindfold, I turn on the vibrator and begin my new game. Placing it directly on her clit, Sky’s reaction is immediate. A loud moan begins echoing around the room as her legs and torso struggle against her restraints. With my free hand, I begin rubbing and squeezing her tits, telling her how sexy she looks while so helpless. “Oh my god, this feels so fucking good!” Sky shouted as her toes curled backwards and her body began tightening once more. Just before she was to cum, I removed the vibrator from her clit, setting it down a foot away on the bed between her legs so that the muted vibrations only teased her.

“Oh fuck please just let me cum!” Her frustrated yell nearly causing me to laugh.

Patting her pussy softly - her body’s surprise evident as she let out a small yelp - I leaned down and whispered in her ear, “You will cum when I want you to cum. If you ask me again, you will be punished.” Her head tilted back in frustration as she let out a deep breath. “Yes Sir.”

Placing the vibrator back on her pussy, her body began straining against her restraints once more. With my free hand, I began rubbing her breasts more forcefully - alternating between squeezing her nipples between my fingers and aggressively playing with her breasts. Sky’s breathing began to get more shallow in response as her arms struggled more strongly against her restraints.

Smack. Smack.

A mixture between a shocked gasp and moan escaped Sky’s lips as I slapped each of her tits. “It turns you on to know that I want to slap your tits while you can’t do anything about it?”

As her head tilted back, she whispered something unintelligible. “What was that?” I asked.

Softly, Sky whispered, “It turns me on thinking about you doing anything to my body, regardless of if I’m restrained to your bed or walking on the street.”

I flicked the switch on the vibrator to maximum power, leaning down to whisper into Sky’s ear, “This is the first part of your reward for being such a good girl. There will be more if this continues.”

Her body began its telltale tightening as the orgasm, twice denied, began building inside of her. As the first waves of pleasure began cascading through her, I used my free hand to once again squeeze her nipples as she let out her loudest moans yet. With the vibrator still firmly placed on her clit, the pleasure continued building and her body began desperately pulling against the restraints, attempting to free herself from my control. As another set of waves began crashing against her, Sky’s moans grew louder and more frenzied, as if she was a wild animal in heat. Staring down at her, I moved my free hand from her tits to her mouth, covering it. Her muffled moans now equal in volume only to the vibrator’s buzzing.

As another wave began building, I moved myself on top of her, straddling her chest with my knees, my ass sitting just above her hips and my cock resting between her tits. Her body now more effectively immobilized, only her legs still strained against their restraints. Lifting my hand from her mouth, I was met by her desperate pleading to stop. Instead, I leaned forward and pressed my lips to hers while my free hand began massaging her throat. As her body began to tighten again, my hand’s massage turned into a strong grip and I leaned back to look at her.

Sky’s mouth now opened, but no words or moans escaped. Her body breaking as the waves crashed down on her once more, the only noise she could muster being small gasps, as she struggled for air. With one final, violent effort against my weight on her torso and restraints, Sky’s body suddenly became loose as full body tremors took over. I removed my hand from her throat and stared as her body continued to shake uncontrollably, completely lost in pleasure while she gasped for breath.

Sliding off of her, I removed the blindfold from her face and was met with only half-opened eyes looking up at me. Her tremors began to subside while I undid her restraints. Attempting to sit up and stare at me, the experience had taken its toll and she quickly dropped back down.

“That was…incredible,” Sky meekly whispered from her back.

“I’m glad you enjoyed it,” I replied as I stood up at the foot of the bed, spreading her legs as I pulled her towards the edge. “We’re not done,” I said, as I positioned my cock next to her soaking pussy before slowly entering her. Sky’s loud gasp of surprise followed as I thrust into her. Her performance had turned me on to the bursting point and I knew I wouldn’t be able to hold off much this time around. Her moans began to match mine as I thrust deeper, sliding effortlessly in and out of her. Grasping both legs, I shifted them towards my shoulders and began thrusting faster and faster.

Another orgasm wracked her body as she lost control of her legs. Just as I was about to lose control myself, I pulled out and twisted her body around, grabbing the back of her head and pulling her mouth onto my cock. As the tip reached the back of her throat, streams of my cum shot out, my legs becoming weak. Sky began sucking the cum out of my cock as I struggled to remain standing and free myself from her. With determination, she kept her mouth locked around me as her tongue danced around the tip. Just before I thought I was about to pass out, she finally relented, allowing me to free my cock from her mouth’s control as I slid down next to her on the bed.

Gasping for air, I struggled to whisper my thanks.

As she repositioned herself to lay across my chest, Sky slid her hand down to rest on my still spasming cock, locked eyes with me and whispered, “I’m not the only one who is going to be spoiled in this relationship.”

Part 3