A Randy Retirement Pt. 11: Megan

When they entered his dim lit playroom, her eyes grew wide and her face broke into a lascivious smile.

Without looking at him she purred in her smokiest voice yet, "I always did like play dates."

He grabbed the leash and led her to a device the was in the shape of an L and made of sanded and lacquered oak posts that were three inches by three inches. The seat was two feet off the ground and the backrest extended up another four.

He told her to sit and she placed her ass on the foot of wood that extended from the backrest, long enough to hold her but still allow access to her holes. The three inches of width was also just wide enough to support her weight and still narrow enough to be uncomfortable to the part of her ass that sat upon it.

Randy cinched her waist and pulled it tight to the backrest using a length of rope that was coiled nearby, wrapping it around her several times. Extending out at right angles from the seat were two pipes that turned down and bolted to the floor and he used more of the rope to secure her thighs and ankles to them, forcing her legs to remain opened wide in a vee for as long as he wished. Her feet dangled off the floor.

He smacked one butt cheek hard, receiving a howl in return, as he reached for the final coil of rope and bound her wrists and arms down and behind her around the back rest, again with several loops, tying them off so that she had little movement.

As he worked, Megan watched as best she could in fascination but did not speak, the only sound being her breathing, which had taken on a sensuous tone.

Randy left her for a moment to retrieve some items from a smaller room and returned carrying a grey box and some clear tubing and other items she could not identify.

She had rested her head against the back rest that extended above it and had a faraway look in her eyes as he took in her tanned body, naked and helpless. He picked up one of the items and held it out of sight against his naked thigh as he tried to read the inscription tattooed on her side, but the writing was so small and crude that it was impossible.

Placing his left hand on the top of her head, he told her to open up and once she had, his other hand brought up a 6" black dildo, which he began to push down her throat.

"Okay, we're going in. All the way down the throat," as he slowly but relentlessly pushed it home. Once the leather pad on the end was against her mouth, he encouraged her, "That's a girl," and he buckled the straps of the gag behind her head.

Megan struggled a little with the intrusion, slightly gagging and he stroked the bulge in her throat and told her, "Relax, just relax. You just took me and I'm bigger so you should be able to handle this."

What he didn't say was that the gag wasn't going in and out of her throat, it was stuck there, filling her, and forcing her breath to come from her nostrils as it found its way down her now restricted airway.

"Relax okay, it's going to be in there for a while," and she moaned and tried to shake her body to no avail. Randy added one more restraint; a leather belt the he placed around her throat and buckled tight until he could just slip his little finger between it and her skin.

"There you go, now you can choke yourself if you're of a mind to," and he chuckled as her wide eyes regarded him.

He removed the leash and plugged the grey box into an outlet. It was a vacuum pump and he brought two hoses around with flat-ended cylinders that were 2" in diameter. He wet them with his own saliva before taking each thimble-sized nipple in his mouth and wetting them as well. Megan mewed in pleasure.

He stood in front of her and slowly brought the cylinders closer as Megan, now whimpering, strained in her bondage to look down as the cylinders grew ever closer. She couldn't see when her nipples expanded and lengthened as the seal was made, but she certainly felt the pull and the jolt it provided. He had set the pump to light suction so as not to blister her, but over the next few minutes those nubs of hers would certainly become more sensitive as the pump would slowly increase it's vacuum over time.

"One more little item," he announced to her as he reached down and picked up a plastic syringe. It was six inches long and an inch wide and he had cut the needle end off and drilled two opposing holes in the plunger about four inches from the end.

Megan regarded it with the slightest hint of fear in her eyes as Randy approached. She moaned through her penis-gag as if to say "Oh no" as he bent to her sex. She could not see what he was doing, but she could certainly feel him play with her clit and knew that what she feared was now inevitable.

Randy examined her clitoris as it was barely visible just out of its hood. He had reversed the plunger in the syringe and he now placed the smooth end that remained against the bud of her sex and began to pull on the plunger. Megan screamed into her gag as her clit was sucked up into the plastic tube. When the holes he had drilled in the plunger emerged from the syringe, he inserted a nail to maintain the pressure on her now captured love bud. His one concession to comfort, he had cut off the sharp end of the nail so that it would not scratch or cut. That was prescient as she was now attempting to thrash in her bonds, and he stepped back to admire her struggle.

He began to stroke her thighs and her abdomen to calm her and as she became accustomed to her situation she settled and he leaned in to whisper in her ear, "I told you when you started this shit that I'd rock your world. We're just getting started slut," and she began to thrash again. Looking down he saw the dangle slowly swing from her belly button with the limited movement she managed. "Ha, even you know you're a slut. Hell Megan, you advertise it," and he reached down and ticked it with a finger to add to its swinging.

Stepping behind her so she could not see, he picked up a multi-strand flogger made of cow leather.

"I noticed earlier that you kinda enjoyed when I used the leash and then my hand to spank you. It was interesting."

Megan did not know what he was doing until she heard the swish of the leather strands, followed instantly by a sharp sting on the outer half of her right ass cheek, the entire part not seated on wood. She flinched and made a small peep. Then came a second swish and another sting on her left. Another flinch and another small peep. Her breathing quickened as she tried to anticipate the next strike, listening for the swish.

Knowing this, Randy varied the placement and timing of his strokes on her bare ass. The only sounds were the mechanical one of the vacuum pump still sucking away at her nipples and the swish of the flogger. Occasionally she would cry out through her heaving, but otherwise the only other sound was her labored breathing through her nostrils.

At first Megan struggled with the pain from the lashing and then she felt her urge grow with each successive strike. For the ninth time the cowhide strands painfully wrapped around the curve of her ass and she flinched as much as the ropes allowed; her head unconsciously snapping forward and restricting her breathing.

She immediately relaxed her neck and resumed trying to breathe. It was then it dawned on her. When she forced herself forward and cut off her breathing, it turned up her internal dials. She thought at first it was the pills she took before she came, but then realized the high from those had worn off. 'No, it's the lack of air' she told herself.

She was sweating and she was hot, inside, and out. Slowly she pushed her head forward again and constricted herself with the belt at her throat; feeling a flood of sexual pleasure flow through her, which was magnified a moment later when the tenth strike landed.

She almost passed out, but maintained the pressure on her throat just a little longer until she relented and backed off enough to breathe. She leaned into the belt again and after twenty seconds and another stinging lash she was beginning to starve for air. The feeling in her nipples from the suction, the unending pull on her clit, the tightness of her bondage, the fullness of her throat with the gag and the work of the flogger all contributed to her heightened sexual state, but it was the lack of breath that sent her over.

Another strike and Randy saw her body stiffen in her binds. Her entire body shuddered as if to lift off the wooden device, held down only by the ropes. It was then he noticed that she was self-choking and he realized, 'She's a painslut.'

For Megan, it was a slow fade that suddenly shattered into white spots dancing wildly before her eyes and uncontrollable shaking as she desperately tried to hold on to the moment her pussy exploded in sexual nirvana. She thought she was having a seizure at first but the explosion in her pussy as she came explained itself and she wanted it to last. As it faded away, she relented her pressure against the belt and her body relaxed, now dripping in sweat.

Randy put down the flogger and stepped behind her. Softly caressing her ass, he began to rub the heat out of the small red welts that were barely visible there. Megan began to whimper, and he asked her if she wanted the tubes off her nipples. She slightly nodded her head yes and he dialed down the suction and turned off the machine. Reaching around from behind, he gently removed the tubes from her nipples and, after depositing them on the floor, returned to take them between his thumbs and forefingers and roll them.

"Can you see your nipples?" he asked her. She shook in the negative and he began to roll them with his thumb and middle finger, using his forefingers to tap the ends of her swollen nips.

"They are at least two inches long and twice as fat as they were," and she whined through her gag, "Oh little girl, don't fret. They're lovely."

With that, he pinched them hard and Megan cried out as she automatically shoved her throat against the belt, choking herself again. When he relented, she did as well, and he walked around to face her.

He retrieved a stool and sat close by her spread thighs, reaching down to pull on the syringe that held her clit hostage and she once again brought her throat hard against the belt.

"Interesting," and he let go of the tube and a moment later she relented. "You know what this means Megan," a statement, not a question, "It means you're a painslut."

"Waa?" she tried to ask through her gag.

"A painslut. Someone who can orgasm from receiving pain. Doesn't mean you won't cum from sex, just means that pain gets you off too."

Megan's first reaction was to tell him he was wrong, but he reached down and thumped the tube on her clit and the sparks of want shot through her body and she knew he was correct. She then was reminded of the belt around her neck as her breathing was cut off and she backed off it. She hadn't even realized she had begun to choke herself again. In her mind, that sealed it. She was indeed a painslut.

Randy then began to work on her recently enlarged body parts in unison, alternating from roughly massaging her nipples to wiggling and tugging on the tube that encased her clit. An idea came to him and he stood to unbuckle the belt from her neck, letting it drop to the floor and then sat back down and started again the manipulation of her body.

"Let's see if you can cum from pain without choking yourself," and he began to work a nip and her clit at the same time and then switching off to the other nub.

Megan's breathing became more pronounced and slower, her hands fidgeting in their rope bindings as she tried in vain to close her legs. Her feet were moving up and down at a furious pace as they hung in the air.

He brought both hands to her nipples and stretched them out, bringing a muted squeal from behind the gag, and told her, "You know what I'd really like? I'd really like to pierce these with some large gold rings," and her breathing quickened. "Permanent rings. Maybe pump them up big and fat and long and put some 10s in them. Or maybe even some 8s. If I'da had more warning I woulda had the stuff to do it with tonight." He let her nipples go and she raggedly sucked in air through expanded nostrils as best she could.

Running his hands down her sweaty sides, he felt the heat emanating from her body and he reached her lap and took hold of the syringe. He noted her juices as they dripped from her open snatch and then pulled the nail out and followed by pulling the plunger the last inches from the tube. It was a difficult pull and so it momentarily increased the suction and sent her into a spasm that started in her hips and radiated throughout her body to every extremity as another orgasm was wrenched from her.

"Nnnnnnnhhhh," filled the room as he worked off the tube and began to manhandle her engorged clitoris and she continued to cum.

"I wish you could see this Megan, your clit is as big as the last joint of my little finger," and he held his left hand up to her face as his right continued working her engorged love bud.

"Nnnnnnnhhhh," and the shaking in her body continued, her arms and legs straining for release.

He released her clit and watched as she slowly climbed down from her apex. Her chest was heaving, and he rose to release the gag from her mouth and after a quick retch, she spit it into his open palm. Megan did not attempt to speak; she was too intent on air, thick mucus hung from her lips and was beginning to form strings.

She had never cum like this and it scared her to an extent, because she wanted more.

"Want. Your cock. Inside," she blurted out between gulping air.

"Now?" he questioned, and she nodded her head.

"Any way I want?" and she nodded again.

"Are we having fun yet?" and she nodded a third time.

He reached down and untied the part of the ropes attached to the frame, keeping her legs roped and then did the same with her hips. Her arms he released completely, saving the rope for another purpose.

Bringing a thick metal circle overhead, he lowered it with a winch and attached the loose ends of the ropes still around her hips to the ring.

Megan was preoccupied with acquiring air and the feeling of soreness that was seeping into her tits and clit to notice what he was doing. It wasn't until he depressed the 'UP' button on the winch that she realized she was headed airborne with her back towards the floor.

The winch brought her body off the L-shaped seat, so that she hung waist high in the air by the rope at the small of her back, Randy holding her steady so that she did not tip over. He used the rope he had removed from her arms to secure her further, running it around the bottom of her glutes and tying it off to the ring, joining the rope from her lower back.

He stepped back and looked at her body, her pelvis, and thighs parallel to the floor, her head and shoulders hanging down as were her feet and arms. He then used the rope still attached to her legs to bind her arms individually to each ankle, forcing her to stressfully arch her back and widen her legs and then he spun her around as she hung.

"Umm, what are we doing?" she croaked as the blood started flowing toward her head.

"You wanted to fuck, this is how I fuck," he growled, and he stopped her spinning by grabbing a knee and stepped between her legs to her low-slung hips.

Megan couldn't see what he was doing, but she felt the giant head of his cock as he rubbed it the length of her slit and then used it to play with her clit.

"Oh god please," she pleaded when the full realization came that he was going to fuck her.

"What did you tell me in the living room when I asked you how you wanted me to fuck you Megan?" he asked.

In her current state, she couldn't remember, it seemed a week ago now.

After waiting a half minute while he continued to tease her, he answered his own question, "You told me to fuck you any way I wanted. That's what I intend to do," and he drew the length of his rigidity forcefully across her clit and forced the head into her pussy.

"Ahhhhhh, damn," she responded as her hanging body flinched and self-buried more of his girth into her.

Randy was not gentle. He plowed the entire ten inches of his cock into the petite woman, watching as it spread her labia at least two inches wide. He pivoted his hips to fuck her hard and steady, bringing a hand up to thumb her still engorged clit as he did so.

Megan did not attempt to speak. The only sound was a loud grunt each time he hit bottom with his entire length. She knew as soon as he entered her that she was going to cum hard. It had started to build as he had rubbed his dick on her pussy. When he had put it in, it felt as if she would split open, but the pleasure that flowed had overcome any concern there might have been. The pounding of her heartbeat that she felt in her head seemed to compound her coming orgasm or at the least, it added a new dimension to it.

It was when Randy grabbed her suspended ass with both hands and began to pound her pussy as hard as physically possible that her grunts lowered in tone and became animalistic and she began to yelled for him to fuck her harder as her body shuddered with each stroke.

"What are you Megan?" he yelled at her.

"A slut," she screamed back in her hoarse voice.

"What kind of slut?" he yelled again.

"A painsluuh, arrgghh," and they came at the same time, her body again quivering as it fought her bonds to grind herself on his dick.

Without hesitation, he withdrew and spun her around, holding his cock near her hanging head as he continued to shoot cum onto her body. He entered halfway into her mouth with ease as her head was hanging down and then pushed the entire length home, feeling the stud on her tongue as it dragged along the top of his dick.

Catching her unaware, she struggled for the breath she had not taken, her arms and legs bound together and flailing as he held her throat captive. Relenting, he withdrew and allowed her to gulp air. When her mouth began to search out the monster cock again, he obliged and wondered if she was even aware of what she was doing in her desperate need for another orgasm.

"Clean me off Megan," and he held his cock just far enough away that she could not engulf it, but close enough that she could lick the head. As she did, he grabbed two hands full of sore nipple and began to work them again, allowing her access to his entire length.

When she had licked every drop of cum and herself from his dick, he walked away and lowered her to a padded mat on the floor and untied her.

Grabbing a handful of her hair that was oiled from her sweat and matted with cum, he forced her up on her knees and stuck his still-hard penis in her face. Her head rose like a snake about to strike as she opened her mouth and then she went down on him to the root in one motion, her gullet spasming as she did so.

"That's a good slut," he stroked her ego as his fists tightened in her tresses and he began to stroke her mouth, the little white bead egging him on.

"No hands. Put them behind your back," he ordered as he began to pound her face and she then began to gag, her throat constricting around his cock.

Randy had no desire to see her puke, so he eased up and her gagging calmed but did not cease. He asked her while he rocked his hips slowly, "Have you ever been fucked in the ass Megan?"

She shook her head no once as he continued to slowly move his cock in and out of her throat. On the next downstroke he did not withdraw, pressing her nose lightly into the flesh above his dick and asking her, "Do you want me in your ass?"

Megan did not respond, she just held station there, her throat impaled on his cock. When the oxygen deprivation hit her, she tried to breathe through her nose and he pushed her head deeper into him, closing her nostrils off before she could get her lungs full.