Third Mistake a Charm? 03

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Cal's Day with Ann and Hilary.
9k words
4.3
9.9k
5

Part 3 of the 3 part series

Updated 06/08/2023
Created 10/21/2016
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This is the third and final story for Ann and Cal, unless my readers think this effort is worthy of continuing. Please enjoy.

A special thanks to my editor, lover, Mistress and wife, M.

*****

Ann's success entering the disciplinary realm, coupled with Hilary's sincere encouragement, emboldened her to develop a rhythm of discipline for her husband. Cal was spanked every two or three weeks depending on Ann's desire to make a point about his moodiness or just replenish the rush she got when she bent him over her knee.

As the spankings became more regular, Cal found himself growing emotionally into the discipline through Ann's soft words of encouragement, when she told Cal how much progress he was making in attitude adjustments. That coupled with her warmth and comforting she so lavished on him after thrashing his bottom beet red.

With the continuity of his spankings, Ann began to increase the duration and severity of his sessions. At first Ann would try to count the hand and brush spanks, increasing them each time. Thereafter, Ann spanked for what felt like a reasonable amount of time. However, she was learning to watch CAL's breathing patterns and how he broke out in a sweat during her longer sessions. Ann also noted that the color of his backside was changing from pink to bright red with her escalated spankings. Her adept use of the hair brush was now embedding a crimson color interspersed with purple blotches from repeated spanks targeted at one spot and the snap in her wrist, she had mastered.

Cal found sensitivity sitting in his chair at the office, reminiscing fondly on the event that caused his subtle discomfort. In fact, he began to appreciate the changes Ann was having in his mood and behavior. Cal liked the anticipation, envisioning being over her knee on the bench in their bedroom.

'Anticipation', Cal thought? 'How crazy is this?', as he connected yearning to be spanked with the length of time between intercourse with his wife, yet it was true. Cal's desire to be disciplined and punished by his wife grew. As crazy as it seemed to him, he craved that intimacy despite the discomfort that came with each session.

Ann too, found the link between his horniness and his desire to be spanked and liked this connection. She began to use it to her advantage when she felt the need to make a significant change in Cal through a punishment, in lieu of a disciplinary session.

The first time Ann introduced the strap into her repertoire, Cal was dumbfounded. Cal could see the strap was well worn and his inquiry where she got it, was met with Ann's devious comment, "All you need to know when I use this strap, the intensity of my discipline will be enhanced through its use."

Cal wondered where Ann's comfort in shopping for these implements of discipline and her skill in wielding them came. As Ann complimented the use of her hand, the brush and strap with each other, Cal became increasingly aware of the impact they were having on him. He knew when his wife would tell him to mentally prepare for "some time with the strap," he struggled to separate his daily business to the transition from awareness, to yearning, then readiness and to finally, dread. The more Cal went through this mental gymnastics, the more accepting his desire to be whipped with the strap. He truly looked forward to these sessions, as they were something so personal and intimate, of the love they continued to build.

These thoughts were evident in Cal's mind as he reflected it had been almost two weeks since they last made love. Cal's libido was growing and evident in his restless nights, waking frequently thinking about lovemaking. Those nighttime thoughts were inextricably linked to being spanked. This night, his thoughts were enough to lead him to ask Ann the next morning when they could have a love making session.

Unbeknownst to Cal, Ann was carefully planning such an opportunity. She pounced on Cal's question with a nonchalant, "Sure, but are you ready for what comes first?"

Cal flinched at her question, thinking there was no reason for a spanking. He could not remember anything that would warrant discipline. "Why, honey? I have not done anything to deserve that," Cal quipped.

Again, Ann was prepared. "Oh you most certainly have earned it! In fact, a severe spanking. Don't you remember that night at the club when you stopped to have a beer with your golfing buddies? One beer became four AND you were late for dinner. AND you drove home when you promised me you wouldn't drive in that condition. AND remember I asked you to check the tire pressure in my car's tires? Did you do that for me? AND you have not cleaned the pool like I asked" Ann barked!

Cal retreated with her onslaught. She was right on all accounts. He debated a rebuttal, but decided it was not worth it. He chose instead to drop his request. Ann let his silence sink in for several minutes before she told him casually, "Ok, whenever you are ready, you just let me know so I can be ready too," she said smiling with that sexy grin that melted his heart many years ago.

The next several days were long and routine, actually boring for Cal, as his horniness grew. 'Fever', he called it...and his temperature was rising. But the nights became even more difficult as his sleeplessness was fueled by the passion to make love with his wife and knowing he deserved to be punished first. On Thursday morning, he caved. "Honey, I am ready. I know I did not behave as I should. And I drove when I should not have. And I failed to do the 'honey do's' as you asked. I think I am ready," Cal said softly.

Ann coolly asked if he was sure he was ready. "As I told you several days ago, this one will be severe. I will be strict since you deserve it. Are you sure you are ready?"

Cal dropped his head, sighed and humbly answered, "Yea, I guess so." Ann quickly asked again, "are you sure you are ready...no guessing with this one. Are you ready to be sternly punished?" Looking her directly, Cal gave Ann a soft and defeated, "yes."

"Very well," since I have volunteer work this afternoon and a church meeting tonight, let's plan for tomorrow. Can you get home early," Ann asked cheerfully, knowing she had sprung her plan on him perfectly?

"Sure," came the response.

"Great," Ann confirmed, sealing the deal.

As soon as Cal left for work, Ann made a phone call.

Thursday painstakingly drug on for Cal. His mind was not on work, or golf or on the nice fall weather, but on his date with punishment. Thursday night was the worst. Cal normally would get up once a night to relieve himself of the water they religiously drank before bed. This night, he was up three times. Couldn't sleep...needed a drink of water. Couldn't sleep...bathroom. Couldn't sleep...was the garage door closed? When he finally gave up at 5:30 AM, he was exhausted, both physically and mentally. A quick read of Strict Julie's Spanking site with his morning juice, reinforced his conviction that he was not the only male that wanted, no, yearned to be spanked.

Breakfast was normal for the two of them. Coffee, a fried egg and toast. Feed the dog, then to work. As Cal made his way toward the door, Ann dropped another bread crumb along her trail, "so we are still on for this afternoon?" Cal gave her a quick peck on the lips, and sealed his fate with a "yep" and a resigned look.

"Good. What time do you think you will be home," Ann asked? "Since it is Friday, how about 2," Cal offered.

"So before you go, let's get you ready for this afternoon," Ann said matter of factly. With beckoning finger and that sexy smile, she lured Cal back to their bedroom, telling him, "Take off your pants and underwear." As Cal obeyed, she disappeared into their closet, only to return with a box of Legg's pantyhose. Size Q+, nude and sheer to the waist, he noticed after Ann placed it so lovingly in his hand. Cal gulped and paused but it was too late. He was hooked.

Cal's uneasiness grew when she opened the drawer where they kept their 'toys'. As Cal fumbled opening the hose, Ann pulled out a new toy, a 6" butt plug and grabbed the KY. Cal had never seen a butt plug in person. Sure, on the sites he frequented, but now in his wife's hands? He was shocked and wary of what was next. Cal went to the bench at the bottom of their bed, where in but a few hours he expected to be whipped, to pull on his hose. Ann stopped him and motioned for him to kneel on the bed.

"Assume the same position you do when I use the strap on your bottom," Ann ordered. Cal knew this position all too well. Once on his knees on the bed, Ann ordered Cal to reach back and pull open his cheeks. Cal shuddered. Ann, enjoying the view and her husband's visible apprehension, waited for Cal to get them completely apart before she opened the top to the KY. Cal heard the familiar 'click' when it was opened. Ann took her time lubing up the tip and wiping the KY down the sides being sure to liberally coat the widest part. When the plug was ready, Ann began her speech.

"This is new. It will be a bit uncomfortable as I insert it. You will wear this frequently as part of your training, so you had better get used to it. Now relax and I will be gentle. Do you understand?"

"Yes, mistress," Cal responded resting his head on their bed.

Ann placed the plug on its target and began to push. Cal flinched, tightening his sphincter. Ann slapped his bottom with her right hand and admonished him to relax. "This is going IN...because I want it IN you ...all day. So relax, or I will add another set with the strap to what I currently have planned for later today... and I'll make sure they wrap way around onto the sides of your thighs. Now relax," Ann cooed.

Cal took a deep breath and upon exhaling, relaxed. The tip went in smoothly. As the diameter grew toward its 1 1/2" girth, Cal moaned. It began to hurt. Ann slowed her penetration, working the plug in and out, ensuring the lube was evenly distributed. Ann told Cal, "Reduce the pull with your hands a bit." As Cal gave his cheeks a bit of a reprieve, Ann told him softly, "Here we go...this time it goes all the way in...relax...take a deep breath and exhale." Cal did as ordered. As he began to exhale, Ann pushed the plug slowly but with resolve. As it approached its widest part, Ann intentionally paused her penetration. "This is what it feels like when you enter me...now you know what it feels like. Maybe in the future, you will be gentler," Ann asked?

Having made her point so convincingly, Ann pressed the plug's maximum girth into Cal. As the plug began its final slide, Ann put her thumb on the base and made sure it bottomed out firmly, fully embedded in her husband. Cal let out a deep sigh as the pain subsided with the plugs final resting place.

"Ok, it is in. You can let your cheeks go," Ann said softly. As he let go, Cal began to rise up from the bed. He immediately felt the plugs presence. He was full, with a dull ache from within. As he stood, the plug pressed against his prostate. Cal had never felt this sensation before. He was sure he did not like it. Yet, when he looked at Ann, she had that same sexy smile he loved. She winked at him and gave him a kiss on the lips.

With that, she placed a towel on the bench and told Cal to sit to put on his pantyhose. Cal was embarrassed, not knowing how to put on pantyhose. He looked inquisitively at his wife.

"Oh, for goodness sakes, you have gawked at me so many times watching me put on my stockings. Roll the top of each leg down to the toe and pull it over your foot," Ann said. Ann made sure to stand directly in front of Cal to secure full view of his feminization and to maximize his embarrassment.

When Cal sat down on the towel, the plug bore deep into his gut. The pain he had endured when Ann stopped its advance at its thickest point, returned. As Cal bent down to put his toes into the gunshed up hose, the plug painfully pushed against his gland. Cal pulled the first leg up to mid-calf before bending forward to start the second foot's entry into the hose. Again the plug bit into his gut. It hurt. But he had no choice but to endure. With both feet and ankles inside the hose, Cal stood, thereby relieving a fraction of the pressure of the plug inside him. He began to gently roll the hose up to his knees. As he pulled them to mid-thigh, he looked at Ann. She was smiling, confidently.

"I want you to pull your junk back between your legs when you get the hose to your crotch. I want you to keep them between your legs all day. And when you go to the bathroom, you be sure to do the same. You can expect me to inspect that when you get home. You got that, mister," Ann stated firmly?

Another "yes, mistress" ensured Cal would be constantly reminded he would be plugged and in pantyhose until after he completed his punishment, still 6 hours away.

"Ok, finish getting dressed and off to the office with you. No underwear! You will text me when you are on your way home later today," Ann required. "You prepare your mind for this one, won't you? It will be severe. Beyond where I have taken you in the past. And I want you to know you have your safe word. You remember it don't you," she inquired?

"Yes, I know the safe word and I will text you," peeped Cal.

Cal slipped into his E350 gingerly. Every time he would sit down, the plug would serve its purpose as a reminder he was owned by his increasingly dominant wife. And he had all day to endure!

As Cal drove off, Ann had things to ready for 2:00. Immediately, she placed a call on her cell phone. At 1:00, she showered. Ann curled her hair into the alluring bob for which she knew Cal lusted. After applying extra heavy dark blue eye shadow, dark eye liner and her best mascara, she dressed in her new, nude, ultra-sheer, seamed stockings. A light green skirt, slit to upper thigh, exposed the tops of her stockings which were fastened to her best corset with 3 garter belt hold up's on each side. Diamond earrings and a choker necklace, both from a prior anniversary completed her outfit. No bracelets or watch as Ann did not want any interference with what she was about to do.

She dropped the spanking hairbrush into her purse, and readied a long thin box with its content. Ann stepped into her 3 1/2" heels and headed for the door. She let the dog in, turned on the alarm since she expected to be gone for several hours. After closing and locking the door, she placed the box at the back door.

Ann walked regally next door to Hilary's house and let herself in. She was stunned at Hilary's appearance. Hilary had pulled her hair back into a pony tail and slicked back her hair. Her horn rim glasses complimented the white, high necked blouse, perfectly creased at the sleeves. The deep ruby pencil skirt that stopped just above her knee, framed Hilary as the strict disciplinarian. With a smile from Ann, Hilary twirled once, showcasing her white seamed stockings that aligned perfectly with her 4 inch open toed heels. Ann noticed the bright red polish on her toes through the sheer stockings. "He will go crazy when he sees you, especially with his favorite white stockings and red toe nail polish," Ann laughed, as Hilary gave her a warm hug.

"Well, here we go. Are you ready," Ann asked Hilary?

"Oh, so ready," Hilary gushed. "I miss this so much. I can't thank you enough for this. We are a good team."

As Ann replied, "you are welcome," her cell phone dinged with Cal's text that he was on his way. Ann quickly typed the final orders in her plan.

'Ok, honey. But need you to take the box I left outside our back door next door to Hilary's before you come in.'

'K', came Cal's response.

Ann and Hilary used the 15 minutes it would take Cal to get home with the final rehearsal of their plan.

As Cal drove home, he was torn. He couldn't wait to get the plug out of his ass and make love to his wife. Yet he knew he would be severely punished first. Cal pulled into his drive way and with a deep breath, admitted he was ready.

Cal grabbed the box at the back door and briskly headed next door. He wanted that over so he could get on with what had been mentally consuming him for the last two days. As Cal rang the doorbell, he planned the conversation to be short and sweet. When the door opened, Cal was stunned! There stood Hilary on her 4" heels, in white hose, a short skirt with the look of a domme. He was speechless.

Hilary smiled. "Why don't you come in for just a minute," Hilary said seductively?

Cal was shaking. He had a pit in his stomach that was compounded by the plug in his rear. He didn't know what to do. "Cal...Please step in to my home, there is someone here to see you," Hilary said in a different tone of voice, much more sternly. He did as he was instructed and was ushered into the living room where he found his wife on the sofa. He was taken aback by her professional, yet seductive attire. But there again, was that sexy smile.

"Hello, honey. Why don't you sit there," Ann ordered, pointing toward a chair directly across the coffee table from her. Cal sat as instructed. Once he was seated, Hilary stepped in front of Cal to sit in a chair to his right. As she did, Cal couldn't help but notice her seamed stockings. 'White seamed stockings', my favorite Cal mused. But what had he gotten himself into?

Ann let silence frame the moment, smiling. "What are you doing here, Cal," she calmly asked?

"Delivering the box to Hilary's as you asked, honey," Cal offered.

"Then do so, please," Ann cooed.

Cal handed the long thin box to Hillary. As she gently accepted it, she gazed deeply into Cal's eyes, whispering 'thank you' through the bright red lips. She was close enough to Cal to whisper, "Cal...Please help me open it."

As he did, he panicked. There was the strap that his wife had added to her arsenal of punishment toys.

A wave of cold sweat flowed from Cal's body. His mouth was dry. He was still shaking.

"Why thank you for returning my strap, Cal. I trust you have learned to respect it as much as my late husband did when I used it on him," Hilary inquired?

As Cal began to piece together the intense thoughts flying through is head, Ann spoke up, "Hilary knows about our lifestyle, Cal. She has known for some time. Remember the first time I caned you when you were suspended from the orange tree in the back yard?" How could Cal forget that? "Hilary was outside that night and heard me use that cane against your bottom. She recognized that unmistakable 'swish' and 'splat' when the cane strikes human flesh. She knows that because she used to discipline and punish her husband. Hilary has coached me a bit, even loaning me her strap which you have felt so many times, haven't you Cal?"

"Yes," peeped Cal.

"What did you say," Ann hissed?

Cal paused, trying to clear the lightning bolts flying through his head. "Yes...mistress," Cal sighed.

Ann's smile signaled he found the right answer.

Again, Ann paused, using silence to make her next point. "Today is new. Many things today are new. But they will be constants going forward." Again, a long pause for Cal to ready himself for her next thoughts.

"I have met your expectations with stockings and the lingerie. I discipline and punish you as I deem appropriate. But you have a decision to make, Cal. You can opt out of this lifestyle if you so choose. If you do, there will be no more lingerie. No more stockings. No hosiery of any kind. The spankings will stop," Ann said matter of factly. She paused to let Cal digest the dilemma racing through his engineering brain.

"If you elect to continue, your discipline will escalate, beginning today. Beginning now," Ann continued.

The wave of cold sweat was chilling his body, making his shaking worse. He gulped and swallowed. His breathing was heavy. Cal was in uncharted waters. He looked at his wife. Ann gave him a sense of reassurance in her look, followed by that sexy smile again.