Third Mistake a Charm? 03

Cal looked at Hilary. She was gorgeous in her 'domme' outfit. She too, smiled and nodded.

With that, Ann reached in her purse and retrieved the hairbrush. She stroked the ridges on the back of the brush, knowing the impact it could deliver.

Ann placed the brush on the coffee table between the three of them, with the business side up. Cal looked at the ominous brush.

"Cal, you have a choice today. Do you want to continue in this lifestyle," Ann asked softly, continuing to look into his eyes?

"If so, show me by doing what I have trained you to do before you get spanked," Ann calmly stated.

Cal knew exactly what Ann was referring to. He knew exactly what he was to do. He had been there so many times before, thereafter draping himself across his wife's knee.

The long silence was broken by Ann's final question, "What's it going to be, Cal?"

While Cal was beginning to recover, he recognized he was physically exhausted from the lack of sleep, mentally exhausted from the shock and awe of the last 15 minutes. He could feel his junk, tucked firmly between his legs encased in pantyhose as his wife had ordered earlier in the day and the pressure of the plug was ever present, throbbing after its extended stay in unfamiliar territory. And he was burning with sexual desire. He tried to process all of it, struggling for clarity.

Cal sighed and slowly stood. He picked up the brush and began to step around the table, pausing as he did. Cal moved to Ann's right side and offered the brush to her in the manner he was trained. "Would you please spank me very hard, Mistress," Cal asked timidly?

Ann accepted the brush, rose ever so slightly to hike her skirt up exposing the tops of her stockings, settled back into the couch and tapped the brush against her right thigh and looked into Cal's eyes.

"Slip off your loafers, remove your socks, unbuckle your belt and step out of your pants," Ann ordered.

Panic rushed over Cal again, as he realized he was about to show Hilary he was wearing women's pantyhose. Nevertheless, he did as ordered by his wife. When he unbuttoned the waist clasp on his pants, they dropped quickly, sliding smoothly over his silky hose. Hilary was directly in front of him and broke into a wide grin.

"Oh, Cal, you look so sweet. Nice work, Ann," Hilary exclaimed.

Cal began the slow droop over his wife's lap. As he assumed his fateful position, he gazed directly at Hilary's white nylon stockings, open toed shoes, showcased by the fresh scarlet toe nail polish. As Cal settled in, he thought looking at Hilary's legs and up her skirt was the only thing he had going for him.

Using her left hand, Ann pulled Cal tightly against her waist and clamped down. She rubbed the back of the brush against the sheer to the waist hose that held Cal's buttocks together. She admired the end of the plug still deeply embedded in Cal's darkness. Eight measured slaps from the brush, followed one after the other, signaled the start of Cal's punishment.

Ann paused after the eight 'preparatory' spanks, telling Cal, "Honey, you earned this. Cal, you asked for this. As I have told you all week, this will be a long and intense session. Behave in front of Hilary, or know it will get worse." With that, Ann began the consciously slow and deliberate rain of spanks, alternating between cheeks. Ann had perfected the stroke, punctuated with a snapping of her wrist just before the brush met its target, and after 10 strokes, Cal could tell, this was a stern spanking. He struggled as she approached 20, and breathed deeply when she paused.

"Cal, you are here for a reason. And I have invited Hilary to participate in your punishment. You will always obey me. Today, you will obey Hilary as you do me. Do you understand?"

"Yes, Mistress," Cal said meekly.

Ann began anew with long, slow paced spanks, reddening both cheeks further. The heat from the first 20 strokes, dissipating during Ann's speech, quickly returned.

Cal remembered to work on breathing steadily and deeply. As he established his pace, Ann, quickened hers, finishing the next 20 strokes with precision and intensity.

"Cal, you may get up. But I expect you to treat Mistress Hilary just as you have treated me," Ann ordered firmly.

With that, Cal lifted himself off Ann's lap and reluctantly reached for the brush. Ann smiled that sexy smile and handed it to him, approvingly.

As Cal stepped toward Hilary, she piped up, "Ann, I love my men in hose. Thank you so much for this unexpected surprise." With that, Hilary arose ever so slightly to raise her skirt higher than Ann did. In doing so, she exposed a picturesque view of her garter belt, framed by her ruby skirt and bright white tops of her sheer stockings. Cal breathed deeply again. He graciously offered the brush to Hilary, which she momentarily refused. Hilary raised her eyebrows, signaling Cal, something was missing. Perhaps it was his numbed brain or his hot buns, Cal slowly picked up on the que, asking Hilary, "Would you please spank me very hard, Mistress Hilary?" The word 'hard' was slow to cross Cal's lips, yet there it was.

Hilary accepted the brush and followed Ann's lead, tapping the brush against her right thigh. Cal began his familiar descent. When he was fully bent across her lap, Hilary noticed the end of the plug, recognizing it immediately.

Hilary glanced at Ann. "My you have grown in the control of your husband, Ann. I am so proud of you. Really, quite delicious," Hilary said grinning ear to ear. As Cal readied himself for the next volley, Hillary rubbed her left hand across his nylon clad bottom. She could feel the heat Ann had embedded in his now swelling flesh. But Hilary momentarily wandered into the past, recalling how she had routinely dressed her husband in stockings or hose, then thrash his bottom purple as she lectured him. As Hilary returned to reality, a wistful smile emerged as she completed a full circumference of his encased ass.

"Cal, I know firsthand, how discipline and strict punishment can improve a marriage. You have taken the right position to be submissive to Ann and accept your fate. I am proud of you, too. Now, behave and don't move," Hilary ordered.

The first spank from Hillary quickly reestablished the heat in Cal's flesh. Like Ann, Hilary worked effortlessly, yet the sounds of each spank seemed to be more intense, like the popping of wood from a burning fireplace. Cal was struggling to get back to his measured breathing as Hilary stopped at 20 strokes. Cal gulped in air and dropped his head. There were Hilary's toes in her ultra-sheer stockings. 'Damn, small favors' he mused.

To provide her husband a slight, but undeserving respite, Ann chimed in, "Hilary, I see his bottom is reddening nicely. Yet, given the magnitude of his crimes, he is deserving of more. Please really lay into him with your next volley."

Hilary followed orders and delivered 20 of the most intense brush spanks Ann had ever seen Cal take, and he was showing the effects. Cal's breath heaved as Hilary smartly delivered blow after blow, stopping when she reached her count of 20. All in all, Cal had taken 48 strokes from Ann and 40 from Hilary.

Ann wasted no time in re-evaluating the level of red on Cal's backside. "Nope, not there by a wide margin. Hilary, where is the strap," turning around looking for the returned treasure?

Cal sunk into Hilary's lap. Hilary picked up on que, chirping for Cal to get up and follow her. As Cal did, he felt the plug press against his prostate. Both Hilary and Ann moved ahead of Cal, toward a hall leading further into Hilary's home, beckoning the condemned to follow. As he did, he was gifted quite a prize, two shapely women in super high heels with laser straight seams rising from their Cuban heeled stockings and disappearing above the knee length skirts. As Cal walked barefoot, he experienced yet another first, his toes squished easily in the tips of his hose.

As they approached a room at the back of the Hilary's home, the girls stepped in quickly, moving to the side, revealing the spanking bench. While Ann and Hilary had planned this step, Ann was surprised at the openness and alluring light of the room compared to the first time she saw it. Ann was impressed. This room was meant for punishment on the bench, and they had the ideal candidate.

Cal instinctively balked. Ann stepped forward to take his hand, encouraging him to continue.

"Cal, you know you need this. And I know you need this. You have needed this for several weeks," Ann said as she began to unbutton his shirt. As the shirt cleared Cal's wrist, Hilary stepped forward to join Ann in leading Cal up to the bench.

Hilary quickly instructed Cal to kneel on the two padded outriggers on each side of the leather haunch. Cal complied. With Cal in place each punishment mistress fastened the small leather strap across his calves. This was followed with the cinching of slightly larger straps, just above Cal's knees.

Cal gazed down at the leather bench before him. It was worn. Obviously, well used. There were darker parts of the deep brown leather that appeared to be heavily massaged with oil and sweat Cal concluded. At the end was a bump, obviously a pillow covered with a clean, white towel.

Both mistresses moved alongside the leather runway and smiled at Cal, pausing. Their smile blended into tightened lips, concluding with nods from each. Perfectly choreographed, Ann and Hilary reached behind Cal's shoulders and gently eased him forward over the bench. As Cal transitioned his weight onto the support, he dropped his head onto the towel and rested his left cheek on the pillow beneath. Both helped direct Cal's forearms onto similar outriggers at the front of the bench, wherein smaller straps were snugged tightly securing his upper arms.

As the girls stepped back, they smiled at each other, knowing they had accomplished the most important step in Cal's transition into a truly punished man. Hilary bent, grasping the 2" leather belt on her side and handed it across to Ann. Ann took the lead threading it into the buckle and pulled smartly, pulling Cal tightly against the bench with the belt just above his pelvis, across mid back. Cal was completely secured.

Ann stepped to the front of the bench and bent down to look Cal in the eyes.

"Honey, this will help you. And it will help me, we both know that. Now relax, practice your breathing and let it in...you will take all of this in" Ann said reassuringly. As Ann was talking, Hilary ran her hands over Cal's butt, still clad in pantyhose. Hilary thought to herself, she would enjoy every second of this, remembering it had been too long since she was last in this position.

Ann announced that each of them would alternate giving Cal, 20 strokes of the strap, and there would be two rounds for a total of 40 each, 80 in all. Ann offered the first 20 to Hilary which she ceremoniously declined in favor of Ann's newfound prowess.

Ann slid her slender hand through the wrist strap and clamped back down on both the strap and solid handle, ensuring a dependable grip. As Ann stepped back to measure, Hilary admired the set-up, shutters slightly closed to filter the light, lights dimmed resembling a restaurant set for dinner, two sexy and empowered women and a man about to be beaten with a 24" long, 2" wide, well-oiled strap.

Before Ann could draw back to deliver her first lash, Hilary blurted, "Hold it, I almost forgot your gift"! With the reprieve, Hilary bounced across the room in her 4" heels to an antique chest. Upon opening the top drawer, she produced a small package, wrapped in pink paper with red hearts and handed it to Ann. Forced to release the strap to open the gift, Ann did so, laying the strap across her husband's cheeks.

Unwrapping the gift revealed a perforated ball gag with a black strap. Ann looked quizzically at Hilary, silently asking 'now what'?

Hilary picked up on the que, saying simply, "This will help him remain relatively quiet during what must be accomplished." With that, Hilary instructed Cal to raise his head off the pillow.

As he did, Hilary commanded, "Open your mouth" and she pushed the ball beyond his front teeth. Hilary traced the straps behind Cal's neck and drew it tight, fastening it more firmly than Cal had expected. He could breathe through his nose and the holes in the ball gag.

"Ok," Hilary confirmed moving back to Cal's right side so she could see his face during his strapping. She sat down on a small stool, spreading her legs so he could see her white stockings and up her skirt.

Ann resumed her position, steadied herself on her 3 1/2" heels and drew back the strap.

'THWACK', the first lash landed centered across his pantyhose clad buttocks. Cal flinched at the searing heat, rekindled with just the first stroke, yet he didn't go anywhere. The restraints were snug and did their job.

As when she wielded the hairbrush, Ann settled into a slow but steady pace, delivering one stroke every 30 seconds or so, but with all her might. Cal used the pauses to process his predicament, helping him to establish his deep breathing. As the count grew, Cal knew he was in for a whipping beyond anything he had experienced before.

The stinging of the strap was intense and as Ann worked her count to 20, Cal struggled to keep his mental focus. The only thing he could see was Hilary smiling at him. He noticed she began to hike her skirt up so he could see the tops of her stockings, she was not wearing any panties and was sporting a Brazilian.

Cal lost count in the haze of the burning in his backside, but was relieved when Ann stopped at the end of her first turn. Ann rubbed her hand over the target zone and felt the familiar heat rising from his flesh. She also noticed the telltale welts so indicative of smartly delivered lashes from the strap.

"I can see increased reddening, but it's not turning purple yet," Ann quipped.

"I don't see any either," Hilary chimed, arising from her stool and smoothing her skirt back down her thighs. "Let me see what I can do about that."

The strap changed hands, and upon being securely embedded in Hilary's right hand, she stopped to relish a moment she had not experienced since her husband's last trip to the bench. She took a deep breath and drew back.

It didn't take long for Cal to return to his state of agony as Hilary clearly had not lost her touch with the strap. Measured stroke after stroke landed with familiar slapping rhythm. Hilary concentrated moving her delivery from below the top band of Cal's hose to below the cleft of his cheeks.

And the searing heat grew as if charcoal on fire.

After Hilary completed her 20, she and Ann met on either side of Cal's now crimson red butt.

"I don't see any purple yet, either," lamented Hilary. "I always enjoyed whipping my hubby in his hose because I thought the restrained flesh couldn't move as much, bringing out the purple and forcing the sting deeper. Maybe Cal reacts differently," she asked?

They studied his butt for a moment. It was striped with outlines of the strap. A few lashes had wrapped abound Cal's right hip and Ann found those welts uniquely raised.

"Let's really concentrate the next go around at the peak of his rounded flesh...his sit spot," Ann suggested.

"OK, but we should probably move to the other side of the bench to balance out a bit," added Hilary. "And, let's try this." With that, Hilary ran her hands up the back of Cal's thighs, softly rubbing from the outsides of his legs to the inside, soaking in the smoothness of his pantyhose. When she got to the top, she reached her fingers under the waistband and began a slow and ceremonial lowering of the nylon. She stopped lowering the hose just above where the larger belt restrained Cal's thighs.

"Now we whip from the top of the hose up to the peak," Hilary instructed. Ann nodded her approval.

Ann again rubbed her fingers across Cal's abused bottom. She marveled how hot it felt, and how there were so many welt lines.

"OK, let's turn this purple," Ann proclaimed!

With the strap back in her hand, Ann moved to Cal's right side. As she did, Hilary moved the stool to the other side. Cal took the opportunity to twist his head to rest on his right cheek to look at Hilary one more time. Not to disappoint, Hilary again lifted her skirt, revealing her womanhood. Ann flipped Hilary a sneer but drew back nonetheless.

The 'THWACK's' recommenced. All Cal could do was breath, slobber into the towel and hope it would soon be over.

Ann worked at her steady pace again, and began to notice a deepening of the crimson flesh as it blended to splotches of deep garnet. She was having the desired impact, in more ways than one. As her count rose, she realized this was her last turn with the strap and slowed her rhythm further. Ann concentrated on precisely delivering the hardest strokes she could muster. Hilary watched in amazement, marveling in the resolve and strength Ann used in whipping her husband.

As Ann's turn expired, she noticed her right arm was tired. Cal noticed he was closer to the end, but still had to endure Hilary's finale.

Hilary bounced up off the stool, her skirt almost falling back to its normal position, but she didn't seem to care. All she wanted was another turn with her second favorite implement. The strap secured, Hilary began anew with punishing blow after blow. She, too whipped with all she had. Hers were not as spaced as Ann's and Cal suffered mightily for it. There was no respite during which to attempt to rest. Cal groaned.

And the purple blotches spread under Hilary onslaught.

Hilary's tour was concluded with two strokes, clearly delivered to wrap around Cal's left side, and they were devastating. Cal flinched against the restraining straps, blubbered and slobbered, moaning uncontrollably.

The girls stepped back to see Cal's back heaving with each breath. They looked at the pile of saliva running from his mouth and nose, down the pillow.

"Wow...that was intense," Ann exclaimed as she ran her hand across Cal's back. It was soaked in sweat and he was trembling. She felt for her love mate, and sighed, quickly remembering his offenses that had landed him prone across the now soaked leather. She pieced together the correlation of the stains on the leather and the wet flesh across it.

Hilary lamented the end of that which gave her intense satisfaction and obvious moisture between her legs. Not to let Cal's predicament unfulfilled, she stepped into the closet, returning with two implements Ann had not seen during her first visit to Hilary's punishment room. Both delrin canes were of equal length and equipped with a smooth black handle. However, Ann noticed a distinct difference in the thickness between each cane.

Hilary smiled, looking directly into Ann's eyes. "He is close. But not there just yet, I can tell. I've been here before. Trust me," Hilary begged.

Ann thought for a moment, digesting Cal's slower breathing. She also processed her tired arm. The deciding factor was the inconsistent purple blotches spread widely across Cal's behind. Ann stepped toward her husband, unbuckled the ball gag and remove it. This allowed Cal to swallow and gather himself a bit. As Ann paused, she assembled her thoughts, deciding to pick up where she started the events.

She looked into Cal's eyes, smiled and began anew, "Cal! You are here because you drove when you should not have. And you have repeatedly failed to do the things I expect you to do like checking the tire pressure in my car and clean the pool! I am disappointed in you and you are being punished for your bad behavior! Do you understand," Ann barked?

Cal nodded which was easy given the lubricant provided by his bodily fluids spread liberally across the, now soaked, pillow.