Chapter 103
Deep explorations

Suddenly, Merry was grinning fiercely. She KNEW she was going to have fun! She had the first act, and it might prove to be difficult; after all, she'd never had to impale her ass on Robert's erection, and she'd CERTAINLY never licked a pussy! But her master HAD been in her ass before - so there was no question of fit - and HE'D licked HER to SEVERAL delicious orgasms, and HE didn't seem to be any worse for the wear. SHE should have no trouble; after all, she was female, and had a MUCH better idea what felt good down there! Merry planned to enjoy herself; after all, her master had made it clear that he expected that she would - why shouldn't it happen that way?

The second part of the evening might prove to be even more interesting! Certainly, it was unclear why Ann - after graphic warnings as to the dangers! - had entered into the dare Merry's master had presented. There was something deep and dark, here... Whatever drove Ann was undoubtedly different than what drove Merry. But her master seemed to know what he was doing... Still, Merry suspected that tonight's activities would be a learning experience for each of them.

No sooner had Ann uttered the words of her submission, than Robert pretended to lose interest in her. "Remove the clothing," he directed brusquely, and turned to watch Merry rummaging in the chest for the handcuffs and ankle binders.

Ann knelt there for a moment, ruminating. "Do I stand up?" she asked.

Robert turned a look of scorn upon her. "No - you aren't wearing anything that requires you to stand to remove it." He glared for a moment, then: "Why on earth aren't you naked yet?"

Ann was still framing an answer to the question when the slap struck. Ann's head rocked, and her eyes watered. She refocused on Robert, standing there looking irritated. "Noooow..." he directed, impatience clear in his voice.

Ann began to fumble at the button behind her neck. "Flip it over your head," Robert demanded, "I want to see 'em!" Ann forced the neck strap over her head, hands shaking as she worked at the button. "It's irrelevant now," Robert noted, "Move to the others." Ann silently cursed her stupidity and did so, managing to get them undone just as Merry arrived with the handcuffs and the binders. As she began fidgeting with the blouse, Robert directed, "Fold it neatly, and place it on the table. I may allow you to wear it again at some point."

Ann blinked. What did he mean by that?

"Now the skirt," Robert urged impatiently. "Come on, we haven't all night!" Ann unwrapped the skirt, revealing her furry mound. Thank God she'd thought to trim it up! As she folded the skirt, Robert circled her taking in the expected wide, cushiony ass. He reached down and grasped a handful with his right hand, then reached around her and grasped a similar handful of her left breast, mauling both as though he was comparing textures. The whole operation was pretty familiar for a man who had never touched her before and she turned wondering eyes on his. But he immediately became irritated, glaring at her and grating, "Yes? Slave?" Sensing her danger, she shook her head silently and turned away.

"Okay," Robert directed, brusquely, "Hop up on the table, and hand me a leg." Robert dropped back into his chair, and took an ankle, extracting a leather restraint from the pile of items in Merry's hands. Ann sat on the table facing him, knees together despite the fact that he had an ankle in his hand. The position was both somewhat unstable and less than esthetically pleasing. "What are you doing?" he demanded.

"Huh?" Ann mumbled, confused, "I..."

"Spread the legs!" Robert barked. "I now own it - I want to see it! Besides, you're unstable!" He demonstrated, lifting the ankle, and Ann promptly almost lost her balance totally and fell off the table. Her left leg went out automatically to help support her recovery and Robert nodded, "Better..." He went back to buckling on the restraint. "Normally," he confided, "I might have Merry do this - it's a waste of my time. But I don't want to present you with any confusion over who it is you answer to, so I'll operate directly upon you until I'm satisfied that you understand advanced concepts such as the idea that if she is following my instructions, Merry is an instrument of my will." Robert turned his head, picking up Merry with his eyes. "We're going to need that spreader bar. Looks like we're going to need to set up some training stations in the family room; I didn't anticipate having slave pens, but with you and Mandi around, and now this one, improvising is getting old." Merry nodded noncommittally and went to get the bar, handing the other items to Ann, who sat looking at them somewhat dazedly. She hadn't really expected him to be so well equipped...

Robert finished the first restraint, dropped the leg, and announced, "Next!"

Ann shifted position and lifted the other leg, maintaining a spread position. She rubbed her cheek, murmuring, "Are you sure all this is necessary?"

Robert quirked an eyebrow, assuming a look of somewhat frayed patience. "All what?"

"Um, binding me up? The slap?" Ann began to worry about what might happen if she continued asking questions, but...

"Yes, and yes," Robert replied. The binders are necessary - you'll agree when the time comes. As to the slap - it was the quickest way to get your attention. You're responding well, too - but it's still voluntary." He paused a moment, working on the buckles, then continued, "You're new to this, so I'm going to allow you to do things like asking an incredible number of stupid questions during the initial phases. When the time comes, I'll take action to see to it that you're quiet for a while." Robert directed a significant look at Merry, who blinked, thought a moment, and nodded, returning to the box.

"There!" he announced, moments later, as the buckles of the other ankle binder settled into position. "Is that comfortable? Does it slide around? It shouldn't. You won't want it to."

Ann worked at the leather. No, they didn't move freely - but they weren't too tight, either. "I think they're okay."

"Good. You may resume kneeling, then," Robert ordered. Merry appeared with a three to four foot bar with snap hooks on either end, and something else Ann didn't recognize. Some kind of harness with a rubber ball... Robert took it from Merry, nodding approval, "Exactly."

Ann knelt, and Robert examined the effort. "Spread the knees a bit. Merry, demonstrate. Basically, if I decide to hold you in a bowling ball grip by sticking two fingers in your vagina and my thumb in your ass, I should be unimpeded in doing so."

This comment was designed to shock Ann, and it was effective. Slowly, the enormity of what she had bought into was dawning on Ann. Eyeing Merry, she adjusted her position, spreading her knees. "Like this...Master?"

"That'll do," Robert replied critically. "Fortunately, you have a nice wide ass..." he mused.

"M-Master? I'm scared!" Rude words and rough treatment were beginning to take their toll on Ann.

"Too late. Sorry," Robert announced in a tone of total indifference. "Actually a bit of fear is healthy at this stage. You'll be fine." Robert was walking a fine line, sparking fear, then allaying it - leading Ann to the point of no return. Merry, by now thoroughly well-versed in the psychological aspects of the situation, kept her mouth shut and tried to give away nothing by action or expression. Robert regarded Ann, asking, "Is this fear an immediate issue that I need to make allowances for? It's time for Merry's demonstration, and I prefer that you were able to assist..."

Merry couldn't help smiling at the big, juicy worm at the end of THAT line! She watched as Ann took it, too, visibly settling herself. Ann returned Robert's gaze and replied, "No, Master, I'm okay."

"Good," Robert replied, as he stood, laid the harness on the table, and began divesting himself of the track suit. Merry shook her head. The difference between them was that Ann probably thought that Robert would have ended the demonstration, while Robert would merely have handcuffed her and maybe installed the ball gag. "All right," Robert continued when the track suit was removed, "You two move the coffee table that way," pointing off toward the other end of the couch, "while I reposition this chair." As the women moved the table out of the way, Robert replaced the chair in a position close to its original location, facing the end of the couch at a distance of a few feet. "Now, Merry, spread out your pad here, between the chair and the couch... Good," Robert approved as Merry moved to obey. "Now, hands and knees, Merry. Come over here and make sure my erection is nice and firm," Robert directed as he settled on the edge of the chair. "You," Robert picked up Ann with his eyes, "can apply the lube."

Ann recovered the lube bottle from the table and knelt behind Merry, but her attention was on the action on the other end. 'Robert has a nice cock,' she mused. It wasn't huge, but it looked to be filling; it was definitely bigger than her ex-husband's. Still fumbling with the cap of the lube bottle, she stammered, "M-Master? Can I..."

"Watch? I guess," Robert responded grudgingly. Merry had crawled forward and was just coming into contact with Robert's cock. She smiled, locking eyes with him, then stuck out her tongue to cradle the bulbous head before slowly engulfing it. Ann, who had repositioned a bit to see it, inhaled sharply. Merry worked her mouth up and down the shaft a couple of times, taking the first four or five inches, then went deeper, trying to get it all in - and doing a creditable job!

Ann was fascinated. She'd given a number of blow jobs during her six years of marriage - now over almost as long - but her husband's cock had never really challenged her, so deep throat wasn't in her repertoire. Robert's cock was apparently good-sized enough to make it interesting...

Merry was watching her master, and she knew almost before he did what he was going to do, and what she would have to do about it. She was unsurprised, then, when he placed his hand behind her head, nodding just the tiniest bit to let him know she understood.

Robert, his hand behind Merry's head pulled her to him until her nose was buried in his pubes - and held her there, for a full five seconds. Ann, whose hand was on her back, felt it begin to arch as Merry tensed, and she held HER breath, too, in sympathy - but Merry's hands never left the floor, and she didn't buck or make any effort to fight Robert's grip. Instead, she merely watched him, trusting, until he released her, then withdrew unhurriedly, sucking air into her lungs through a slightly red face.

Robert smiled. "Another demonstration," he announced, "One not part of our dare. Do you think YOU can do that?"

"Ohmigod! That was incredible!" Ann was as flushed as Merry from the excitement. "I don't know - I've never..."

"Given a blowjob?" Robert finished, visibly surprised.

"Well, not like that!" Ann retorted. "I've done it, but not... deep."

"Well, undoubtedly you can; the question is, are you properly motivated?" Robert remarked pointedly. "We'll see what we can do about that..."

"You're plenty firm, Master," Merry observed, removing her mouth from his cock, "Do you want me to continue?"

"No," Robert replied, "I agree with you. Besides, I want to supervise the lubrication." He moved around to a position off-side, leaning over Merry's back to watch as Ann again fumbled with the cap on the lube bottle. Finally, she got it open and dispensed some on her fingers, then gingerly attempted to apply some directly to Merry's anus.

"You'll have a tough time like that," Robert observed, then directed, "Pour some up here," indicating an area higher up, but in the crack between the cheeks, "and let it run down to the insertion point. You DO need to actually BE there..."

Ann, who had been fumbling around the area with the pads of her fingers, felt give in the sphincter, and positioning a finger for insertion, began to press. Merry winced, and Ann withdrew. "Fingernails," she apologized, indicating their painted length.

Robert took a look, and frowned. At that length, they were probably artificial... He sighed, "You'll just have to be careful... If you injure Merry, I'm not going to be happy! More lube, especially on the fingers."

Ann did as directed, applying more lube, then she placed her hand, palm upright, so that she could lay the nail of her index finger at the opening of Merry's anus. Reaching out with her other hand, she spread the cheeks, locally, which opened the little puckered rosette a bit, and she slid part of the nail in. Robert caught on and helped by spreading Merry's cheeks as she again opened the lube bottle, and used the long fingernail to decant a small amount of the lubricant inside Merry's anus. This appeared to work; when Ann pushed forward, the ball of her finger met little resistance from the gobbling little mouth. Working gingerly, Ann pushed the finger in to the first joint, withdrew it, added some lube, and worked it deeper, trying hard not to scratch the delicate inner tissues.

Robert sat back and watched Ann's look of total concentration as she worked. Ann was flushed, and her nipples were quiveringly erect; obviously, she found the activity erotic. "Good," he approved, "but I want two fingers in there - deep!"

Ann looked up, nodded, bit her lip, and organized the insertion of her middle finger. This wasn't as difficult as expected, the same nails that made the initial entry problematic, placed one over another, provided a smooth ramped surface that eased the insertion. Ann continued to work, slowly working the fingers in and out of Merry's clutching sphincter and into the buttery depths of her anus.

Robert backed off to get a look at how Merry was handling the effort. Merry was holding still, her eyes vacant as she concentrated on sensations occurring in her nether regions. After a moment, she became aware of her master's regard and nodded in response to his unasked question. "Okay... Good, even," she murmured.

Robert nodded, and returned his attention to where Ann was again dribbling lube down Merry's ass crack in support of ever deeper penetration. Robert got a look at the level in the bottle and announced, "Better be a bit more sparing - you'll need it, too. Maybe you can recover some spillage."

Ann nodded. Merry's pudenda and upper thighs were soaked, after all. Ann started gathering drips on Merry's thighs, but recognition of an opportunity to... touch... another woman... there... quickly brought her hand to Merry's pubic bush. Merry jumped, inhaling quickly, as Ann's finger swept over her clitoris and upward along her labia, gathering the excess. After a moment, Ann repeated the action, as with her other hand she prepared to insert her ring finger in Merry's distended anus. Merry again rewarded her effort with a wriggle and a gasp. Ann, totally involved in her effort, was trickling her own natural lubricant under the impetus of her arousal. 'I could do this all night!' she thought.

Robert, watching, held his peace. Obviously, when he got her past the initial embarrassment and self-examination, Ann was going to open up like a flower. He waited until the third finger was fully involved, and Merry was undulating from the penetration and the now unnecessary sweeps along her cleft, then rumbled, "I'd have thought that you'd want her to fail! Instead, you've exceeded your instructions!"

Ann looked up, and whispered "Oh!" at the realization that she'd gotten carried away. Robert suspected that given time, she'd have been fisting Merry's ass while masturbating her before she surfaced. While he might have considered it entertaining, it would have defeated part of the evening's demonstration, so... "Wipe off on the towel, and present your wrists."

Ann scooped up the towel and went to work on her musky hands. The smell of Merry's natural lubricants was everywhere, and Ann was surprised that she didn't pick up more fecal matter; there was only a bit around the nails. She presented her hands to Robert.

Robert handcuffed Ann's right wrist, then ordered," Turn around." He captured her left and cuffed her hands behind her. "Okay, let's get this show on the road. Merry, grab the bar there, and lay it along the foot of the couch. You need to be facing that way, anyway." Turning to Ann, he remarked, "I should have had you lube me while your hands were still covered. Ah, well..."

He positioned himself behind Merry, and directed, "Okay, bring it back a bit. I'll pick up some lube from the drips."

Merry backed up, and Robert began running his cock all over her thighs, then worked into a position where he was running it up and down her nether lips. Merry dropped on her elbows and moaned as his cock slid along her labia, rubbing her clitoral hood. After a few moments of this, Robert announced, "Okay, I think I'm good. Showtime!" He motioned Ann to a ringside seat and positioned his glans at Merry's winking orfice. "It's all yours!"

Merry nodded, and walked her knees back so that she was in an extended position, then slowly drove her torso back. For a moment, it looked like there would be a problem, but then her anus flowered open and flowed over Robert's glans. Merry kept moving, slowly absorbing the first four to five inches, stopping only when it became apparent that she had reached the limits of previous lubrication. Then she levered herself forward two inches and worked in a bit more.

As Merry slid forward again, Robert grabbed the bottle of lube and drizzled a bit on his exposed length. Merry stroked twice more, and Robert was embedded to the pubes. "How does it feel?" he asked.

"Mmmmm. Nice and full!" Merry replied, obviously happy. She began to rock back and forth, doing the work of the ass fuck. From her smile, Ann had to assume she was enjoying it... Ann watched the whole proceeding, fascinated, from the start to the point where Robert caught her eye and announced, "Okay, go sit on the couch."

Ann complied, maintaining her view as much as possible. "I've got it!" Robert announced, and took over being the motive power behind the pounding that Merry's ass was taking. He actually slowed it down, murmuring, "This isn't the point of the exercise. Merry, move up and hook her ankles to the bar." Robert buried his cock to the hilt, then moved with Merry as she adjusted her position. He grabbed Merry's hips and took the support of her body from her arms.

Merry, relieved of having to support her upper body, was able to use both hands to connect Ann's ankle restraints to the snap links at the ends of the bar. Ann offered no resistance; it didn't seem necessary, despite the undignified position it left her in. Ann was an observer, floating outside her body as she watched these preparations going on, pliantly moving each foot into position. When Merry had finished, Ann sat on the couch with her hands cuffed behind her and her feet locked to the bar, about three feet apart. Merry resumed her all-fours position.

Robert leaned forward, gently rubbing Merry's flanks, moving slowly in her ass as he murmured, "Okay, Merry. I know you've never done this before, but I've done it to you, so you should have a pretty good idea what's going on." He smiled, something Ann could see, but Merry couldn't. "Since you're connected to the same type of equipment, you may even have some ideas I'd have never thought of! Are you ready?"

Merry locked eyes with Ann and smiled. "Yes, Master!"

"This is a learning experience," Robert noted, "so feel free to express yourselves, both of you. Make her scream!"

Merry, eyes locked on Ann's began slowly moving forward, so as not to dislodge Robert. Robert, spying a potential problem, directed, "Move it up to the edge, we're not digging in the cushions for it!" Ann moved forward, positioning herself on the edge of the seat, restraint links rattling as the bar moved. Robert urged, "Use the bar to control her, as necessary. We don't want her running off." Merry nodded, never taking her eyes off Ann's. "I'm gonna take it easy, so as not to joggle your elbow. What you're doing is more important than what I'm doing. Understand?" Again, Merry nodded, slowly closing on Ann.

Ann watched Merry as a rabbit watches a rattlesnake. She didn't fear what was about to happen, exactly - she wasn't sure what the emotion was that was building a huge bubble in the back of her mind, but she knew that that bubble HAD to burst!

Merry moved in VERY close, and Ann watched her nostrils distend as she took in Ann's musk. "Now I know where the fish remarks come from," she chuckled, warm breath washing over Ann's mons, "But it isn't quite that, is it?"

"No," Robert agreed, huskily, "it isn't. I find it VERY arousing; I can't guess what you think of it."

The touch of Merry's warm breath had broken Ann's lassitude, bringing her sharply into contact with her surroundings, but the bubble of emotion, huge, still hadn't either burst or identified itself. Ann knew, however, that the moment was upon her. A woman was about to tongue her sex - what emotion would that contact generate?

Merry dropped her eyes momentarily to examine the target critically. Ann's pussy was undoubtedly larger than hers on the outside, the lips looser. The top of her mons was padded a bit more, and the clitoral hood was quite long. But the lips were retracted, and an inch-wide damp, pink furrow was revealed, the darker mystery of the vaginal opening at the lower end, and a bright coral bundle peeking out from within the gathering point above. Unless Merry missed her guess, Ann was VERY aroused! Merry again locked eyes with Ann, extended her tongue, and ran it along the open furrow from perineum to the bundle of nerves at the top.

"AUUUUGHHHH!" Ann threw her head back and howled, galvanized! The bubble in her mind announced that it was pure lust, as it doubled in size!

Merry, smiling, regained her lock on Ann's wide eyes as soon as they reopened. She settled her lips over Ann's now fully-distended clitoris, and began drubbing it with her tongue.

Ann was far up the slope toward her orgasm, her arousal jumpstarted by the events of the evening and her inability to escape her captivity. She couldn't even hold Merry's hypnotic eyes. It had been some months since she had had anything better than masturbation, and that didn't even compare to the things going on here! Her head lolled back and she began a litany that would prove to be all to short: "Ohh!... ohh...ohh...ohh ...ohh... yesss...ohh... ohh... there!... ohh...ohh... OHH...OHH... OHH...THERE!...OHH!... OHH! ...OH GAAAWWWWDDDDD!!!!!!" Ann began convulsing, unable to close her legs because of the bar, her torso undulating as powerful contractions convulsed her vagina. "AAAIIIEEEEEEE!" Merry pinned Ann's feet to the floor with the bar and abused her clitoris unmercifully as Ann thrashed, screaming her joy. The bubble in her mind burst into a million stars, and Ann lost consciousness.