Tom's Appointment

Tom should have known better. It was something between a bet and a dare; something he'd been goaded into by his half-drunken buddies on a particularly boring night. The four of them were halfway through splitting a case of cheap beer when Sam had brought out one of those cheap "XXX" newspapers from a vending machine a few blocks from the airport.

They'd chuckled at the attempt to write news articles, then they'd laughed and howled at the huge variety of ads for "adult services" in the back. Hell, the ads were three-quarters of the whole thing. Sure, some of them looked nice and professional, but the majority were poorly-worded, misspelled, and the pictures in them were blurry, if there were pictures at all. There were women offering massages, men offering massages, even folks who seemed somewhere in-between offering massages and other services.

Tom's buddies were pretty familiar with the folks in-between; they'd had fairly open city upbringings and were at least familiar with the concepts. Tom's midwestern background became painfully apparent as he just got more and more confused as the night and the beer went on. Eventually, Sam, Ralph, and Jack couldn't resist goading him a little.

The bet was simple enough. They'd open to a random page, drop a quarter on it, and whatever ad the quarter landed on, Tom would call and make an appointment for "services." Whatever it was or whoever it was. Tom was both ill-informed enough and drunk enough to go through with it; if he actually went through with the appointment and meet-up, it was a hundred bucks. That, and the other three would pay for any "services" involved.

Tom was just sharp enough to flip past the majority of "men offering services" ads, and the quarter landed on a blurry picture of a blonde in a corset and stockings. The ad offered an "unforgettable night, five minutes at a time, with a beautiful T.S. model and guaranteed full-release." It was also fairly cheap.

"What's a T.S. model?" asked Tom, his alcohol-riddled brain reeling from the possibilities. He kind of had a sense of what "full-release" was, and he didn't hate the idea.

"I think that's a 'Totally Satisfying' model," said Sam, barely holding back the laughter.

"Looks like you lucked out. Yeah, we'll pay for that. Make the call!"

So, it was that a few hours later, Tom was ringing the bell on an apartment in a worse part of town, his buzz fading and wondering what the hell was about to happen.

Anticipation had him half-hard, worry kept him at half.

A sultry blonde in a silk robe opened the door, and Tom had to raise his eyes to look into her face. With the heels she was about six foot four, and built solidly.

"Tom?" she asked, her voice low and dusky. Tom just nodded, trying to find his voice.

This was NOT what a boy from the Midwest was supposed to be doing with his Friday night.

She chuckled, low and sexy. "I'm Vicky. Come on in."

Tom entered the darkened apartment, eyes taking in every detail. The furniture was old, but well-maintained. It was mostly covered in purple velvet and other dark cloths, lending to an air of mystery and sensuousness. There was a sweet incense in the air, and soft music. Vicky closed the door and smiled at him.

"It's pay up front," she said. "I like to get that out of the way so there's no stress. You can always tip me afterwards, if you think I've earned it," she said, holding her hand out.

Tom fumbled for the crumpled bills his friends had put together. They HAD added some for a tip, so he held that back. It seemed like the right thing to do. He handed the money over, and Vicky straightened, organized, and folded the bills before sliding them into the pocket of her robe.

"You've never done anything like this before, have you?" she asked, leaning back against an inner doorway. Her breasts thrust out against the robe, and Tom shook his head.

"Not ever," he said. "It... it's kind of a dare, really," he admitted, blushing a little.

"You're adorable," said Vicky. "Let's get you your money's worth, all right?"

Tom just nodded, and Vicky took his hand and led him into a back room.

The room featured a four-poster bed in the same purple velvet and a large dresser with a LOT of drawers. Vicky slipped the robe off and hung it on a hook, revealing the corset and stockings she was wearing in the ad. Tom swallowed hard; even if she was kind of solidly built, that outfit said "sexual activity." She turned to him and gave him a long, appraising look.

"You'll want to get out of those clothes. All of them."

He nodded, and started to disrobe. Whatever this thing was, he was in... his hard cock was making the choices at this point, and it said "do this thing."

Soon he was naked, his clothes neatly folded on top of the dresser. Vicky walked a slow circle around him, then playfully shoved him towards the bed.

"Don't worry, I'll make your first time a good one, baby. Just relax."

Tom laid flat on his back, hard six inches sticking straight into the air. Vicky went to the dresser, opened a drawer, and took out a handful of silk scarves. Tom's eyes widened, but he laid still.

"This is going to be something very special for you," said Vicky. She laid the scarves next to Tom's head, then released the top of her corset. Tom's eyes drank in her big, round, stiff breasts; he'd never seen the like, and he was immediately mesmerized.

Vicky took up one of the scarves and, after making sure Tom had gotten a proper eyeful, she wrapped it around his eyes, blindfolding him.

"This makes it better," she said as he murmured in concern. "You feel everything more. Do you trust me, baby?"

"I... yeah," said Tom, the last of the beer fueling his bravado. "Let's do this."

Vicky chuckled deep in her throat again, and took his wrist in her hand. "Relax."

Tom laid still as she tied his wrists and ankles to the four corners of the bed, laying him out spread-eagled. His cock throbbed with need, and the strangeness of the situation only made the need more intense. He heard her move to the dresser and open another drawer, then felt her weight on the bed next to him.

There was a brief mechanical whizzing, then a ticking next to his head.

"Five minutes at a time, baby. I'm good at this... very good. You just relax and let Vicky work."

"Not much choice," said Tom, as he heard some sort of container being opened. Then, after a moment, her warm, oiled hand softly grasped his throbbing prick.

Tom moaned out loud as she slowly stroked his raging cock, fingers just tight enough to glide over his stiffness. She knew just how to touch him, just where he needed a brush or a rub of the pads of those fingers. She teased the man vein along the underside, the sensitive spot just below the head, and the super-sensitive cleft. Tom squirmed, unable to control his body's reactions to the lascivious stimulation.

"I'm going to really enjoy this," said Vicky, as she kept her stroking slow. Her fingers traced the length of him, up and down, over and over, bringing him incredible stimulation, but never quite enough.

"Oh... oh shit," said Tom, his voice quivering. "Please... please, Vicky... just a little more... PLEASE..."

"Shhh," said Vicky, keeping the speed slow. "Just let Vicky work. It's all good, hon."

Tom gritted his teeth as his hips thrust without his permission, her hand tightening ever so slightly on just the right spot. Then, suddenly, she sped up. Just a little. Just the right amount, fingers gently clasping at the slick head of his cock as her fist slipped up.

The timer next to his head rang, and Tom yelled as his cum boiled out in huge ropey spurts. Vicky milked five hard spurts out of him, his cum landing on his stomach and thighs as she continued to jerk him just so.

She finished milking out his orgasm, then released him. Tom, exhausted and happy, basked in the glory of his orgasm. Then he heard the mechanical whirring of Vicky turning the dial on the timer, and the ticking was set back next to his head.

"Vicky? What..."

Then his cock was surrounded in wet, tight heat, and Vicky moaned around the head of his super-sensitive cock. Tom groaned loudly again, partially in pain. Was this what she meant by "five minutes at a time?"

"Oh... oh FUCK!" cried Tom, as she slowly and gently sucked his too-sensitive cock. Tom threw his head back and pulled at his bonds, but he was well tied and not going anywhere. As the nerves in his prick screamed, he started to wonder if maybe he'd done something that wasn't entirely safe.

He'd had a blowjob or two before, but this was different. Vicky had skills. She knew just what every part of her mouth was doing; from the tight, slick lips that gripped his cock in a ring of pleasure to the tip of her tongue dancing along the underside; even the teeth that occasionally grazed the rim of the head of his cock, bringing ice-cold electric shocks of too much pleasure. His nerves wanted a chance to come down from the first orgasm, but she never gave him the chance.

Again, it was slow... just, barely, too slow. Tom tried to beg her to stop a couple of times, but every time he started to speak, Vicky would let her teeth graze the head of his cock and the shock of sensation would take the breath out of his lungs. She was in total control of him through his cock, and there was nothing he could do to stop her.

She would work the head for a little bit, drawing yelps and little screams from him, then take him all the way down her hot, tight throat. She had no gag reflex to speak of, and every time her nose mashed into his pubic hair, Tom would let out a low groan and pull hard on his bonds. His muscles were getting quite the workout even as he laid there helpless to stop Vicky's attentions.

Suddenly, she sped up just a little, her head bobbing up and down at a furious pace, sucking him all the way in with each descent of her light, wet lips. The timer next to his head rang and Tom cried out as his cock fired off again, his cum blasting into Vicky's hungry mouth.

She milked him completely with lips and tongue, then slowly pulled off, gasping a little. Tom was breathing heavy, covered in sweat.

"That... that was great... thank you," he said, nervously. "I... I think that's good, you can let me up now..."

Then she was back at the dresser, opening another drawer. Before Tom could ask what was going on, there was the whir of Vicky setting the timer, and the ticking resumed next to his head.

"Oh... oh shit no, please... no more..."

"We've barely started," said Vicky, her voice even lower. "You come to me for services, you get what you pay for. Now relax. I think you'll like this."

Tom pulled hard on the scarves, finding them just as tight and binding as when they'd started. Then her hand was on his scrotum, softly caressing his nuts, rolling them in the sack. Tom relaxed a little. That wasn't so bad.

Then she was gently lifting his nutsack, and rubbing something cool and slick on his anus.

"Wait... whoa... don't do that..."

"I said relax," said Vicky. Then Tom heard the sound of something buzzing just before something cool and hard was pressing gently at his shitter! It was vibrating and it didn't feel entirely bad; at least not until Vicky started forcing it up his ass!

"AH! NO! DON'T WANT! STOP IT!" yelled Tom as the vibrator penetrated his sphincter.

Vicky only chuckled and let the blindfolded young man yell as she violated his asshole.

It hurt, it felt wrong, it was nightmarish, and then she expertly hit his prostate. Tom's yelling ceased, replaced with a deep gasp as his exhausted, too-sensitive penis started to rise again. His exhausted limbs went limp in their bonds as she pressed the vibrating tip of the hard-plastic vibrator to his inner love gland and made excruciatingly slow, tiny circles with it.

The inexperienced young man had no concept that these sensations were possible, and he went just a little mad. He groaned, his breath squeezed tight from excitement and lust even as his tears wet the blindfold. He was taking something up his ass, and he was loving it!

Vicky kept gently massaging his aching, tortured balls as she probed and prodded his prostate, his anus quivering around the vibrator. It was pain, it was pleasure, it was excruciating and exhilarating, and it was just... too... slow...

Tom's mind was lost in a haze, trapped between begging her to stop and begging her to go just a little faster. Suddenly, she scraped her long fingernails along the underside of his scrotum as she pressed the vibrator in just a LITTLE harder. The timer rang and Tom hollered as his cock valiantly tried to fire off again. A couple of weak spurts, and Tom had experienced his first prostate orgasm.

Vicky gently removed the vibrator and released his nuts, and Tom felt her weight come off the bed.

"I... I think I'm done, now," said Tom, his voice weak. He felt like he'd run a marathon, his nuts aching from the unaccustomed activity. This was pleasure and it was torture and it was more than he could take. Vicky's weight fell back on the bed, and she slipped the blindfold down off his eyes.

"You're almost done," she said, smiling. "Not quite, though. I think you're ready for the good part."

"The good mmmmphhh!" Tom started to ask, as Vicky tightened the scarf that had been around his eyes over his mouth. He was effectively gagged, his eyes wide and adjusting to the light.

Vicky stood next to the bed and lowered her panties, then released a strap between her thighs. Her hard eight-inch cock sprang up, throbbing and ready. Tom yelled behind his gag, only barely comprehending. T.S. did not mean "Totally Satisfying."

Vicky lifted the timer, and looked down at Tom with a combination of lust and pity. "You get one more," she said, twisting the dial with a mechanical whir. "Then I get mine."

The ticking timer went next to Tom's head, and Vicky reached down and caressed Tom's aching cock.

It was overly-sensitive, but the prostate orgasm had given the nerves just a bit of a break. It took only a few moments for her gentle caresses and a few kisses to bring Tom to a semblance of hardness, and a minute of slow sucking brought him to another full erection.

Then she was straddling his waist, her bigger cock bobbing over his stomach.

"Now relax, Tom. I'm going to do all the work, and you're going to cum again. Just accept it."

Tom shook his head, his fear of the unknown and the pain in his groin bringing more tears to his eyes. As he watched, helplessly, Vicky rocked back, reached behind herself, and lifted the tip of his cock to her own anus.

With a gasp, she sank down on him, taking his whole length up her butt. Tom closed his eyes and felt his head go limp. It was wrong, it was bad, it was... heaven.

His cock had never been gripped so tightly, never been in so much wet heat, never felt such pleasure. Vicky raised herself upright on him, her big artificial breasts glistening in sweat, and slowly rose. When only the head of his cock was clasped in the harsh tightness of her tight sphincter, she squeezed it a couple of times, drawing gasps and yelps from the gagged young man.

Smiling down at him, she sank down on him quickly again, bringing pain and pleasure to them both.

Tom's first assfuck was not a gentle affair. Vicky started to bounce up and down on his hard prick with wanton abandon, taking his cock again and again, squeezing it tightly in her depths and growling from the sensation of it. Tom's head lolled about, the sensations overcoming him. His overly-sensitized cock screamed for relief; if not the release of orgasm at the very least the cessation of activity.

She fell forward, her hands on his chest, clawing at him as she drove her hips down on him again and again, grunting and mewling. Her eyes went wide, looking down into his, and she squeezed down a little extra hard.

The timer rang, and Tom fired the remnants of his nut juice into Vicky's bowels with a whimper. There wasn't a lot left, but she used her tight asshole to milk out every single last drop.

He ached from the bottom of his chest to the top of his knees. He groaned slightly when Vicky pulled herself up and off of his softening cock, unable to do so much as pull at his bonds any more. Vicky took a moment to calm her breathing, then bent down and nibbled the side of his neck.

"You ALMOST made me cum with your cock up my ass, you naughty boy," she said. "Then I wouldn't have properly gotten mine. Just for that, I'm setting the timer for TEN minutes, this time."

Tom barely heard her. He wanted to drift off to sleep; he was more tired than he could recall ever having been, and the dull ache in his lower body only drove him to deeper exhaustion. He didn't know what she was talking about, and at the moment, he didn't care.

He was relieved when she released the scarves on his ankles, anticipating freedom. Then she was lifting his right leg by the back of the thigh, and using a scarf to tie his knee to the upper corner of the bed. As he started to weakly struggle, Vicky tied his other knee to the other corner, leaving his legs spread wide and his ass completely exposed.

He moaned behind the gag as she slid a pillow under his hips, lifting his ass just a bit. He was starting to get it.

Smiling wickedly, Vicky gave the timer twice the twist she had given it before, and settled down on the bed between his widely-spread thighs.

"The ad promised full release," she said, as she rubbed some lube on her throbbing cock. "That means both of us, baby. Pucker up, now..."

The feeling of the hot, slick head of her cock against his asshole gave Tom a burst of adrenaline and he struggled and cried out behind the gag. He shook his head and pulled at the scarves so hard that the wood of the four-poster bed creaked with the effort. Vicky nodded; it was so much better when they were a little lively!

Slowly, SO slowly, she forced the head of her big cock up his tight, virgin asshole. The penetration of the vibrator earlier had loosened him a bit, but his terror and pain made him tighten up good and proper for her. Putting her hips into the effort, Vicky slowly sank her whole length up the exhausted, helpless young man.

Once her balls rested on his, she got a grip on his hips and started to fuck him, good and slow. This wasn't one of her five-minute quickies; she settled in for a long, hard screw. The young man and his protests had been exciting her all evening, and it was time she took her pleasure and satisfaction from him most fully.

Tom's burst of adrenaline made him quite a ride for her; he bucked and squirmed and yelled behind the gag, straining the bonds and the bed with his attempts to free himself from the situation. It made his ass twist and thrust back on Vicky's throbbing cock, and inspired her to thrust in more and more vigorously.

Over a few minutes the adrenaline surge waned. Vicky was almost disappointed as fatigue settled into the young man's frame like a big, heavy blanket, sapping all of his strength and even the token of resistance.

She fucked him good and hard, grunting as her cock bottomed out in his bowels again and again. A sheen of sweat covered her body, matching the one on his, and her muscles trembled with the effort of fucking Tom deep and hard.

She wrapped her hands around his straining thighs and pulled his ass onto her cock harder and deeper, her hips slapping into her ass with a clapping sound that filled the room and drowned out his pitiful whimpers.

To Tom, it went on forever. Her big, throbbing cock rubbed against his already stimulated prostate and brought him waves of pleasure, but the pain from his violated asshole merged with the ache from his strained, tortured balls and turned into a whole-body agony that dragged heavily on his very consciousness.

He was barely cognizant when the timer rang, and Vicky's muscles locked in a rictus as she fired rope after rope of hot, sticky cum into his bowels. She trembled with the effort of cumming into the young man's ass, and then slowly thrust into him a few more times. His unwilling, quivering anus milked out every drop of her pleasure, and seemed to release her only regretfully.