A Good Challenge

"Jennifer" (surely not her real name) finished setting up the restraints on the four corners of the hotel bed. I looked on as she carefully set the for-now empty cuffs on the crisp white bed sheets. I was fully clothed, but already hard in anticipation of what was to come.

"Okay, let's go over the rules again," she said.

I responded from my place in the overstuffed chair, my mouth slightly dry from the arousal that was slowly building inside me: "The hotel safe over there"—I gestured to the room safe tucked into the open closet—"contains $500 in cash. I know the code for the keypad, and you don't. Once I'm tied down, you have two hours to get the code from me. There are a few rules:

"First, you are not allowed to use pain.

"Second, you can tickle, but it can't be used as torture to get the code—this is supposed to be about tease and denial.

"Third, the safe word is only to be used by me if I'm in physical pain or distress. It can't be used to avoid teasing."

"Sounds like a good challenge," she said. "And the $500 is as a bonus on top of my usual fee?"

"Of course." I nodded toward the plain envelope on top of the dresser. Jennifer sauntered over, making a point to brush lightly against my legs on her way by. She picked up the envelope and, after a quick peek inside, dropped in into her purse.

Then, she turned, her expression now a sultry, piercing gaze. "Let's get started. Clothes off, now."

***

I undressed and reclined on the bed, suddenly self-conscious to be nude and so very exposed in front of the fully-clothed Jennifer. The bed had been stripped of the covers and pillows leaving me lying atop just the clean, white sheet in the middle of the hotel room's king-sized bed.

"Arms up," she commanded.

I did as I was told, and Jennifer quickly secured my wrists in the padded velcro cuffs attached to the top corners of the bed. She then did the same to my ankles, and methodically tightened the slack out of each restraint so that only the slightest bit of play remained in my arms and legs. It was not uncomfortable, but being stretched out further exacerbated the feeling of helplessness that engulfed me as Jennifer looked down with a grin.

"Comfortable?" she asked. "Speak now, or hold your peace for the next two hours."

"Comfortable enough," I responded, my cock beginning to harden after hearing Jennifer say "two hours."

"Good," Jennifer replied. "Now, to set the timer." Jennifer grabbed the bedside clock/radio, currently reading 8:37pm, and set and alarm for 10:37pm. She set the clock back on the nightstand, before turning it away from me to face the wall.

"No need for you to have any distractions," Jennifer said with a smirk. My penis responded to her words by tightening further, and jerking slightly off my stomach to bob in the air.

"Oh, this is just going to be too easy, isn't it? You can barely control yourself and I've barely gotten you tied down. Just imagine what you'll feel like once I start to play with you."

Jennifer reached down beside the bed and grabbed one of the pillows. She lifted my head and replaced the pillow behind it, propping my head up so that I had a panoramic view of the room. "You're going to want to see this," Jennifer said.

Jennifer retreated to the foot of the bed, never breaking eye contact with me. I'd obviously already surveyed her body, but my heightened arousal somehow made all the details stand out even more. She was about 5'7'', thin but with ample breasts—maybe C-cup-size—and seductive curves at her hips and ass. She was wearing a thin t-shirt and denim shorts that went only a few inches down her long, lean legs.

"Well then, no time to waste," Jennifer said giddily. In one smooth motion, she removed her t-shirt and tossed it onto the floor beside the bed. Underneath was a pink lace teddy that was sheer enough to make out the outline of Jennifer's pert nipples, but opaque enough—and covered with just enough strategically placed lace pattern—to leave a little to the imagination. Jennifer unbuttoned her denim shorts and let them drop to her ankles so that she could step out of them.

"Like what you see?" she asked. It was a rhetorical question, since my now rock-hard cock was all the answer she needed. "Of course you do," she said, answering her own question.

Jennifer retreated to the corner of the room, where she had a small duffel bag. "Let's see what we have here," she said in a husky voice, rummaging through the bag. She let out little sounds of affirmation and discovery, "ah-hahs" and "mm-hmms," as she pulled several items from the bag and laid them carefully on the dresser. Although I couldn't make out every one, I took particular note of what looked like a long-handled artist paintbrush, as well as a small mess of cords and a rubber sleeve.

***

Jennifer approached from the foot of the bed, slowly dragging her fingers across my ankle and up the inside of my thigh, narrowly missing my fully erect penis. As she got toward the middle of the bed she climbed on top of it and nestled her lithe, warm body into my side, resting her head on my shoulder.

"So, where should we start?" she asked rhetorically, as her fingers lightly tickled the front of thighs and up onto my stomach. "We have plenty of time, so we're definitely not starting with that cock," she said, answering her own question.

She continued to play her fingers along my stomach and chest, pausing every so often to caress my nipples. I hadn't often thought of my nipples as an erogenous zone, but every touch of Jennifer's fingers felt like an electric shock, and my cock jumped noticeably every time her fingers plucked at one of my nipples. Jennifer moved her head into the crook of my neck, letting her lips trail up my neck, over my jawline, and finally allowing them to nibble lightly at my ear.

"By the time I'm done with you, you'll be begging to give me the code," Jennifer rasped sexily into my ear. "And as a reward for being such a good boy, I'll give you the best orgasm of your life." I could only groan in response.

"I find that soft kisses have a way of breaking down a man's resistance," Jennifer said. "Do you think it will work on you?" With that, she began to plant soft, wet kisses along my ear lobe and down my neck, working her way to my chest. She kept this up for a minute or two, allowing her tongue to swirl around my nipples whenever her mouth approached them. Jennifer continued to descend slowly down my body, kissing my stomach down just below my navel. Her mouth was so close to my erection that I could feel the warmth and wetness of her breath on its tip. My hips thrust, almost involuntarily, but with all the slack taken out of the bonds my cock could only bob vertically, but I could not push it any closer to Jennifer's mouth.

She chuckled. "Look at you. We're not even halfway done with my kisses and you're cock is already begging for more. Not yet, baby."

Jennifer continued her torturous kissing treatment. She carefully avoided my penis as well as the small pool of precum that was gathering on my stomach underneath the bulging head. Her soft, sucking lips traced the outlines of my thighs, her saliva leaving a scorching trail down my body. Every nerve ending I had seemed to simmer just under my sensitive skin. Jennifer went over my thigh, dipping her head between my legs to kiss the sensitive flesh on their insides. This went on for what felt like hours, until she reached the bottom of my feet and, with a playful scrape of her teeth, she stood up at the foot of the bed.

"It's barely been 15 minutes, hon, how are you going to stand this?"

"15 minutes?" I choked out. Her expression, locked in a teasing smile, betrayed nothing about whether she was lying or not. But my level of arousal made it feel like I'd already been strapped down for hours.

***

Jennifer returned to the side of the bed, her eyes locked on my turgid member. "Does it always get so red?" she asked. "I bet not," she responded when I shook my head no.

She then dipped her finger underneath the head of my cock, grabbing the string of precum that hung from the tip. She looked me in the eye as she brought her finger to her mouth and tasted me. "Mmmm," she moaned. "I love the taste of a man's arousal. Would you like to taste mine?"

My eyes widened, both in excitement and fear of what I knew was coming. Jennifer slipped her fingers into the spaghetti straps on her lace teddy and dropped the straps from her shoulders. While looking me straight in the eye, she held the top up by bringing her arms together, giving me a glorious view of her cleavage pressed together over the rim of her lingerie. After just a second of time to take in this sight, she let her top drop, revealing her pert yet ample breasts and brownish, hardened nipples.

She turned away from me so that she could push the rest of her outfit down off her legs, and so that she could bend over and provide me a view of her ass while she did so. Now totally naked, before standing up she peaked at me coyly under the crook of her right arm.

She turned back around, this time dipping her finger into her own sex between her legs and bringing her finger to her lips. "Already wet for you," she told me.

Jennifer climbed on the bed and stood over me, straddling my chest. She stood there, looking down at me, for several seconds, allowing me to take in the sight of her nudity and her glistening pussy. Leaning over me, Jennifer grabbed the headboard and slowly lowered herself onto my face.

"If you do a good job, maybe I'll decide its time to touch that needy dick of yours," she said.

"Yes, Jennifer," I responded, the musky smell of her warmth filling my nostrils as she lowered herself onto me.

As soon as her pussy was in range, I parted Jennifer's pussy lips with my tongue, tasting her sweet nectar.

"Eager boy," she chided, a hint of a moan in her voice.

I got the hint and probed more softly, teasing around her opening with my tongue, and using my lips to find her clit buried in her folds. Finding it, I used my mouth to encircle her clit and applied gentle suction, just enough to allow my tongue to find it and flick along its tiny length. This drew genuine moans from Jennifer, and I knew I was on the right track.

I alternated between that medium-speed licking of Jennifer's clit and pausing to dip my tongue into her pussy. Within a couple of minutes I could tell she was approaching orgasm. The muscles in her calves, resting on my arms beside my head, began to tense and release in rhythm, her hands gripped more tightly on the headboard, and her moans grew more urgent and rapid. I turned all of my attention to her clit, lashing the little nub with my tongue.

That did it. With a groan, Jennifer tumbled over the edge, releasing the headboard with one hand to entwine her fingers in my hair and pull my face further into her sex.

"Fuck!!," she shouted, shuddering from her orgasm, before collapsing on the bed beside me, her head resting on my chest. My face glistened with her juices and I licked my lips to taste her some more.

"Clearly not the first time you've done that," Jennifer said, looking up at me.

"I can hold my own," I joked, my cock throbbing and pulsing.

"Your cock must be quite needy by now," Jennifer said, "but you've been a very tough boy. I'm not going to ask for the code, because I can tell you won't give it to me yet, but why don't you just tell me how many numbers the code is? No harm in that. And I could touch your cock if you tell me," she slyly dangled her fingers just over the head of my raging member.

She was right, of course. There was technically no harm in telling her how many numbers were in the code. She could have figured that out just by looking at the instructions on the safe if she wanted to. And I so desperately needed my cock touched.

"Four," I said, "there are four numbers."

"What a good boy," Jennifer said. "And good boys always get what they want."

Jennifer dipped her fingers underneath the head of my cock, into the ever-growing pool of precum draining from the head.

"I find that a man's precum is a great lubricant. So slick and plentiful—at least if you take the time to tease it out."

Jennifer gathered some of my precum onto the fingers of her right hand and rubbed her fingers together, coating them liberally. "Ready, baby?"

She didn't wait for an answer, instead applying her slippery fingers to the underside of the shaft of my cock, lightly and slowly rubbing back and forth, base to just under the tip.

I shuddered at the first touch. Nothing had ever felt as good as Jennifer's fingers teasing my long-denied cock. My hips bucked, trying to get just a little more pressure from her teasing fingers. But she was too good, allowing her hand to rise and fall with the motion of my hips, just remaining in ever so slight contact with my penis.

"Oh, yes baby," Jennifer moaned, almost pouting. "I bet that feels so good after not being touched for so long. Can you believe we've only been here for 40 minutes?" I groaned deeply in response.

"That's right, we have so much more to go." She continued to run her lubricated fingers up and down my cock, never speeding up, always going just fast enough to stoke my arousal, and slow enough to ensure I wasn't going to approach the edge just yet.

***

After several minutes of devastating finger treatment, Jennifer popped off the bed. In the haze of my urgent need, I barely registered her departure. I certainly didn't notice her grab the mass of wires attached to a lubricated silicone sleeve. But I most certainly did notice when she lightly gripped my cock at the base and slid the sleeve over the head of my cock, pushing it firmly to the base. The sleeve was the first contact she had made with my sensitive cock head, and I jerked my hips in response. Once the sleeve was in place, it covered about the bottom two-thirds of my shaft, and left my head exposed to the air.

"You know, as much as I love watching you jerk around uncontrollably, it doesn't really work for what I have in mind for the next hour," Jennifer said, just a note of disapproval in her voice. "I think we need to fix that."

Jennifer went to her duffel bag and returned with a long strap. She tossed one end underneath the bed, letting its end come out on the other side. The other she draped over my stomach to the other side of the bed. She used a fastener situated on one of the ends to connect the two ends together, and pulled tightly to remove the slack. As she pulled, the strap grabbed my hip bones, the strap passing just underneath my cock head and fixing me firmly to the mattress.

"That's better," Jennifer smiled. I tried to wiggle my hips up and down, but found I could barely move them at all. My cock trembled slightly as I jerked, but my hips barely moved at all.

Jennifer rounded the bed and again sat down next to me, grabbing a small control box attached with wires to the silicone sleeve. She turned the box over in her hands, as though examining it.

"This is a vibrator," Jennifer said, almost as if to herself. "It has three settings. The beauty of the sleeve is that it stimulates your cock, but because it does not cover your head, it will be a slow ride for you to the edge of orgasm. Let's give it a try."

Jennifer flicked one of the buttons on the device, and my body flexed as the sleeve began vibrating gently on my cock. The feeling was like nothing I'd ever experienced. And I could tell Jennifer was right. While I could feel myself climbing the hill toward orgasm, the progress was maddeningly slow.

Jennifer put the control box back down on the bed and climbed between my legs. I lifted my head to watch as she lowered her head toward my crotch. She looked at me with a sly smile right before she poked her tongue from her mouth and swirled it around one of my tightening testicles.

"Ughh," I gasped in response. Jennifer continued to torment my balls with her pleasurable ministrations. She worked around each globe with her tongue, and then began to gently suck each one into her mouth, only to swirl her tongue around each one once more.

If the vibrator was ensuring a slow journey to orgasm, Jennifer's play was certainly speeding it up. My cock began to flex on its own, almost begging for some stimulation on the head. Jennifer lifted her head just long enough to give me a knowing glance and shake her head. "Not yet."

The vibrator and Jennifer continued their torturous tag-team of my engorged member, the sleeve bringing me closer and closer to orgasm while Jennifer's mouth stoked my desperation with her laser focus on my balls. I realized that I was moments from orgasm. The sleeve seemed to be coaxing the cum from deep in my balls. I closed my eyes and let the vibrations and Jennifer's tongue work on my penis. My balls pulled toward the base of my cock, ready to release their seed. And all of a sudden, with a click, all stimulation was gone.

"Gahh!!," I nearly shouted, my eye shooting open. I immediately saw Jennifer staring back at me, smiling, almost giggling, and holding the control box in her hand.

"You know, the great thing about having your balls in my mouth is that I can feel exactly when you get to the edge. . . . And then I can stop it."

Jennifer gave me about 30 seconds to calm down, before repositioning herself between my legs.

"Let's do that again, shall we?"

Jennifer continued this treatment for what felt like hours. Using the sleeve to edge me, and her mouth to both torment me and gauge just how close to orgasm I was. She was a magician, a wizard, a guru. Each time the stimulation was withdrawn, I groaned in erotic agony, slamming my head back into the pillow. Over and over, she edged me, only to pull me back at the last moment.

"Please!!" I shouted after what may have been five or six slow, agonizing edges.

"Don't please me," Jennifer said. "You know exactly what I want from you."

***

Jennifer approached the bed again. I was a mess of precum and desperation, my cock twitching and dripping, the skin a deep red color that can be explained only by true, unyielding need. She held up her hand so that I could clearly see two long, soft artist's paintbrushes.

"Let's see what kind of fun we can have with these and that sensitive cock." Jennifer again sat between my legs, this time putting her own legs over mine. This had the effect of further restraining my movement while ensuring her full access to my cock and balls. For the first time, I saw a hotel water glass that Jennifer had filled with a yellowish substance.

"Olive oil," she said, following my gaze. "I find it increases the torture of the paintbrushes. I'm told it feels almost like little, warm tongues licking your cock. Very sexy. You'll have to tell me if you agree."

Jennifer coated the paintbrushes in the oil, held one in each hand, and applied them to my cock, "painting" from base to tip. She couldn't have been more right, it was like two small tongues torturously licking and tickling my dick. I wrenched my head from side to side at the sensation. Again, the contact was just light enough to slowly build my need.

Unlike her other techniques, Jennifer did not avoid my cock head with the paintbrushes. Far from it. Instead, recognizing how extremely sensitive it was from such lengthy teasing without contact, she would pause periodically to focus the brushes on the ridges connecting my head to my shaft, and to run the brush over the magic spot on the bottom of my cock head.

After a couple minutes of this treatment I felt like I was rocketing toward orgasm. But Jennifer saw it too. She retreated with the paintbrushes to the base of my cock, a slightly less sensitive area that allowed her to prolong by just a little bit the rise to orgasm. She carefully watched my balls as though they were a meat thermometer, waiting for the telltale tightening that precedes orgasm. When she saw it, she withdrew the brushes.