Mentored By A Dowager

This story is a continuation of my story 'Night Flight' about a young FLR couple (Lisa & Jack) that an older woman (Marie) meets on a flight. After teasing Jack for the duration of the flight and leaving him with a ruined orgasm, Marie gives Lisa her card and suggests that they meet for some advanced instruction on controlling Jack. Lisa decides to take her up on it.

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It had been a week since their trip and the flight where Lisa and Jack had met Marie. Now Lisa was looking at the card Marie had handed her. It read simply:

Maria Antonia Freemantle

Duchessa Vedova del Ducato di Gabbiato

56 E 73rd St, New York, NY 10021

and on the back of the card was a handwritten phone number. Lisa had been quite impressed after Marie had handed it to her and as they deplaned Marie explained that her husband Frank had been managing partner in the New York office of Credit Albion. After a business trip to Italy (and a heavy night of drinking), he decided to buy the peerage associated with the ruins of Gabbiato Abbey in Lombardy by buying the abbey.

When Lisa asked about the abbey, imagining a grand estate like the one in the Downton Abbey TV series, Highclere Castle, Marie laughed and explained that it was literally a pile of rocks on the edge of a cliff in the Italian Alps.

Then she chortled "That action made Frank the 'Duca di Gabbia' which literally means 'Duke of Caged'!"

Lisa knew where Marie lived, it was a Queen Anne style row house in the historic district, and she decided it was time to visit with her and take her up on her offer. She dialed the number.

"Hello?"

"Yes, hi, is this Marie? This is Lisa."

"Lisa! Indeed, from the flight, and your husband, Jack--such a nice boy."

Lisa smiled, then said, "Well, I wondered if I might take you up on your offer...you know...to show us a few things?"

"Oh my dear girl, of course. What are you doing Saturday? I could send my car to pick you up at around 10 in the morning, would that work for you?"

Lisa was almost giddy at the idea of a chaffered car and agreed to the time. After a bit more discussion they hung up.

When Jack arrived home from work that afternoon, Lisa decided to test his state of mind. His ruined orgasm on the plane had calmed him down a bit, but now almost a week later she could tell the pressure was building. This morning he had been 'the perfect pet' and that usually was a lead up to a request for release.

"Hi honey," she said sweetly as he embraced for their kiss. Lisa prolonged it, shoving her tongue into his mouth.

Jack was caught off guard, he didn't think Lisa would be amenable to a release for him and now she was practically ripping his clothes off. After a long kiss she pulled away.

"I've got steaks for dinner, does that sound good?"

"Yes it does!" Jack suddenly had a moment of suspicion wondering why she was being so nice. It didn't much matter because his dick was painfully attempting to harden in his cage--a reminder that he really wanted out.

"Well then my studly man, why don't you set the table while I get things going in the kitchen?"

"Yes ma'am!" Jack practically yelled as he headed to the dining room. In his mind he was thinking "Tonight's the night!"

They had a great dinner, cleaned up the kitchen and were relaxing in the living room when Jack took his shot. "Lisa, you are just a helluva cook, those steaks were great and that pie was over the top," Jack said as he moved a bit closer to his wife.

"I'm really glad you enjoyed it."

"You know what I would really enjoy," Jack replied, spreading his legs a bit.

"I know honey," Lisa consoled, "after that episode on the plane, and now it's been a while and you must be really congested down there." Then she slid her hand onto his leg near the knee letting it slide up the inside of his thigh towards his crotch.

Jack reacted with a guttural sound and spread his legs apart, tilting his head back with his eyes shut as she touched him.

"Speaking of the plane, I called Marie and she invited us over to her place tomorrow," Lisa said as her hand moved upward.

"What?!!" Jack exclaimed as he sat up and drew his legs together protectively, "No, no way, absolutely not!"

"OK honey, if that's how you want to be," Lisa said as she got up and walked towards the bedroom. Jack quickly realized that his chances of release were quickly leaving the room and his dick, having tried to harden painfully in his cage in anticipation, was deflating quickly. Jack jumped up and went after his wife.

"Ok, ok, if I agree to go will you let me out now?" Jack whined.

Lisa turned, smiled and put her hand on Jack's crotch, her fingers touching the cage behind the fabric of his briefs and pants.

"You know very well that is not the way this works, but I will say that your chances of relief will dramatically improve if you go with me."

Jack sighed and agreed. He had known it was going to go this way and at least if he let the old bitch fondle him a bit he would have a mind-blowing experience with his wife later.

The next morning, Jack awoke to the inviting aroma of freshly brewed coffee. He got up and stretched, feeling energized and ready for the day ahead. As he sipped on his favorite mug of dark roast, he pulled out his trusty tablet to check the game schedules.

Suddenly, Lisa appeared in the doorway of the kitchen, causing Jack to almost drop his coffee cup in surprise. She was dressed in what she liked to call her "good girl outfit," which always managed to captivate him just as much as her more scandalous attire. Her long hair was styled into two playful ponytails, framing her face perfectly.

But it was her outfit that truly caught Jack's attention. A skin-tight white crop top hugged her curves and accentuated her ample cleavage, leaving little to the imagination. The soft fabric gathered at the center, revealing just enough skin to make Jack's heart race. And below that, a pink micro-mini skirt barely covered her bottom, teasingly hinting at what lay beneath.

As if that wasn't enough, Lisa had topped off her look with thigh-high white stockings and adorable pink and white saddle shoes. Jack couldn't help but feel a rush of heat at the sight of her, thankful for the indecency test that saved him from losing complete control.

She was like a walking fantasy, and Jack felt lucky to have her by his side - whether she was dressed up or down.

"You need to know that I am wearing my crotchless lace panties," Lisa said matter-of-factly as she poured herself some coffee with an exaggerated bend over. Jack had gotten up and was 'walking funny' as he approached her, she always knew when he had a hard-on working at his cage.

"No you don't," she said sternly as he reached out towards the hem of her skirt and she playfully batted his hand away. Looking at the clock she said, "It's almost ten, go put on the clothes I laid out for you in the bedroom."

"Yes ma'am," he said as he turned away, thinking that the sooner they got this over with, the sooner he would get under that skirt.

In the bedroom Jack found his clothes laid out on the bed. One of his smaller T-shirts that really showed off his guns along with skin-tight jeans that would make sure he didn't forget for a moment he was caged. He sighed and got to work getting dressed. When he went out in to the living room, Lisa smiled and said "That's my boy!" staring at the bulge at Jack's crotch. With both hands she felt the bulges in his arms. "You knocked out a few push-ups out, didn't you?" she smiled.

Jack blushed and admitted that he had, "Got to do something to get that old bag's attention."

Suddenly Lisa's demeanor changed to anger as she pushed Jack away. "Don't talk like that about her, she's a Duchess and you will treat her with respect--AT ALL TIMES, do you hear me?"

"Yes, ma'am!" Jack replied, somewhat stunned by Lisa's reaction to what he said.

"Better," Lisa said, "now come on, it's almost 10 and the driver will be here any minute.

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At exactly 10 AM a small limousine pulled up in front of their building. The driver got out and held the door for them after confirming who they were. During the short ride Lisa had her hand on Jack's thigh, slowing rubbing it just below his crotch, driving him crazy. He was relieved when the car pulled up in front of Marie's house, clearly just oozing wealth from the stone steps leading up to the double-door entrance and fancy wrought iron railings. Jack was impressed and Lisa just looked spellbound. After the driver let them out they walked up to the door and Jack hit the bell.

After a moment the door opened and they were confronted with a large man wearing a tux said to Lisa, in a British accent, "You must be Mrs. Thompson, welcome. My name is Otis, the Duchess is expecting you."

Otis ignored Jack as he gestured Lisa inside, but turning to him said "The Duchess would like me to make sure you are comfortable, so please follow me." Jack didn't know what to think as Lisa had gone ahead. Then he heard Marie say "Lisa! I am so glad you could come, and I see you have brought Jack. Well, come right in and let's have a glass of wine. Otis will make sure that Jack is comfortable."

Jack didn't like the fact that the women had a private agenda and that he was going "to be made comfortable" by Otis, the largest black man that Jack had ever seen this close--the guy could easily be an NFL defensive end. Otis towered over Jack's six foot frame and could have easily stared JJ Watt down. The tux fit him like a glove and it was clear that he was not only huge, but athletic as well. The British accent just finished the picture.

"Follow me" Otis said to Jack as he turned and went inside. He led Jack down a hall and Jack could hear Lisa and Marie talking and giggling as they passed a doorway. Otis led him through a side door and into a large room that held a frame of some sort in the center that Jack couldn't tell what it was. The walls were lined with tall, polished wood cabinets.

"Take off your clothes," Otis ordered.

Jack hesitated, eyeing the strange frame in the center of the room warily. "I'm not sure I'm comfortable with that," he said, crossing his arms defensively.

Otis's expression remained impassive. "The Duchess was quite clear in her instructions, sir. You are to disrobe completely so that you may be properly prepared for the ladies."

"Look, I don't think..." Jack began.

"Your wife has given her consent," Otis interrupted smoothly. "And you agreed to follow her wishes today, did you not?"

Jack swallowed hard. He had agreed, desperate for release after days of denial.

Jack slowly began to undress. His hands trembled slightly as he pulled his tight t-shirt over his head. He could feel Otis's eyes on him as he unbuttoned his jeans and slid them down his legs, revealing the chastity device encasing his manhood beneath the thin fabric of his briefs.

"Everything off," Otis instructed.

Jack removed his socks and underwear, leaving him completely naked except for the metal cage locked around his genitals. He instinctively moved his hands to cover himself, feeling exposed and embarrassed.

"Hands at your sides!" Otis said forcefully.

Jack reluctantly lowered his hands, face burning with humiliation as he stood naked and at attention before the imposing man. Otis circled him slowly, appraising his physique with a critical eye.

"Turn around," Otis commanded. Jack complied, rotating in place as Otis continued his inspection.

"Very good," Otis nodded, "Now, step over to the frame and lean into it, grab the two handles there and put your feet into the footrests."

Jack's eyes widened as he finally realized what the strange contraption in the center of the room was - a sturdy metal frame with restraining hand and foot holds. His heart began to race.

"I-I don't think I want to do this," Jack stammered, taking a step back.

In a flash, Otis closed the distance between them. His massive hand clamped down on Jack's shoulder.

"Now, now," Otis said calmly. "The Duchess and your wife have plans for you. It would be most unwise to disappoint them. Into the frame, if you please."

Jack hesitated, his mind racing. Part of him wanted to bolt for the door, but he knew he'd never make it past Otis. And Lisa had agreed to this... hadn't she? The promise of release after days of denial beckoned.

Swallowing hard, Jack stepped forward and complied, his naked body bending at the waist as he gripped the cold metal bars. He felt incredibly vulnerable as Otis guided his feet into the pads at the base of the frame, spreading his legs wide.

"That's it," Otis encouraged as Jack positioned himself in the frame. "Hands on the grips, feet on the pads."

Jack complied, his breathing quickening as he felt cool metal against his skin. With practiced efficiency, Otis secured Jack's wrists and ankles using velcro straps attached to the frame.

The frame that Jack was secured in was supported by two beams attached to the ceiling of the room and it could pivot from vertical to horizontal and then vertical the other direction. Whoever was secured in it could be rotated through 360º. Additionally, the hand holds and foot pads could move.

"Now let's get you properly positioned," Otis said as he began adjusting the frame. Jack felt his body being tilted backwards until he was nearly horizontal, his legs spread wide and elevated, his back supported by a padded crossbar. The position left him completely exposed and vulnerable.

"There we are," Otis said, stepping back to survey his work. "The Duchess will be pleased. Now, let's prepare you properly for the ladies."

Otis moved to one of the polished cabinets lining the walls and said "The Duchess prefers her guests to be thoroughly cleaned before joining her," Otis explained as he opened a door revealing a tall cabinet with what looked to be a miniature antique gas pump inside, the kind with a glass reservoir.

"This is a reproduction of a Wayne 615 Visible pump that the Duchess had made for its current purpose. This may be a bit uncomfortable, but I assure you it's quite necessary."

Jack's eyes widened in alarm as he realized that Otis had grabbed the hose of the pump which was fitted with what looked like a large enema nozzle instead of a pump spout.

"Wait, no - you can't -" Jack sputtered.

"Not to worry," Otis said calmly, "this is not a punishment enema, but I do need to add some ginger oil and soap to the water, so let's get this in place first."

Jack felt a cold, slick sensation as Otis applied lubricant and then carefully inserted the nozzle into Jack's bung. He gasped at the intrusion, face burning with shame.

"Deep breaths now," Otis instructed as he squeezed the handle and Jack felt the end of the nozzle inflate, effectively securing it in place. Then the huge man moved to another one of the polished cabinets lining the walls and retrieved several items. Jack craned his neck, trying to see what the man was doing, but his position limited what he could see.

Otis moved back into view and Jack saw him open the top of the pump reservoir. He poured the contents of two different bottles into the water and Jack gulped as he noted it was one gallon on the scale.

"Well then, I think we're ready."

Jack heard a switch snap and the start of a gentle humming. Then an intense rush of warmth filling his insides followed as the pump filled him with fluid. The ginger oil created a tingling, burning sensation that made him squirm against his restraints.

"Oh god," Jack groaned as the warm liquid slowly filled him.

"Just relax and breathe through it," Otis instructed calmly. "The Duchess insists on thorough cleansing."

Jack squeezed his eyes shut, trying to focus on his breathing as the enema continued. After what felt like an eternity, the flow finally stopped.

"Very good," Otis said. "Now we'll let that sit for a while before expelling."

Jack's insides churned uncomfortably as he squirmed and writhed in the frame.

Otis retrieved a small key from his pocket and unlocked Jack's chastity cage. As he pulled it off Jack's cock sprang to stiff attention.

"It looks to me like you are enjoying this," Otis smiled approvingly.

Jack's face burned with shame as his erection stood proudly on display. He wanted to protest that it was just a natural physical reaction, but he couldn't deny the intense arousal coursing through him.

Jack gritted his teeth, fighting the urge to expel the liquid. After what felt like an eternity, Otis said "I'm going to remove the nozzle now, so hold it in."

Jack clenched his muscles as Otis carefully deflated and removed the nozzle. The burning sensation from the ginger oil intensified, making him squirm against his restraints. Otis pressed on Jack's abdomen massaging the enema.

Jack swallowed hard, his cheeks burning with shame and arousal. "Please, Sir," his voice trembling. "I... I can't take much more."

Otis's large hands paused their ministrations, one resting on Jack's stomach while the other gripped his hip firmly. "I beg your pardon," he said mockingly, his deep voice rumbling through Jack's body. "I don't recall asking for your opinion on what you can or can't take. The Duchess and your Mistress will decide that."

"Please," Jack whimpered.

"Please?" Otis asked, "I think given this circumstance you may want to show a bit more respect, boy."

"Yes, Sir. I'm sorry, Sir," Jack managed to say, his breath coming in short gasps.

"That's better, now just a moment longer," Otis replied calmly. He then produced a large plastic container.

"Here we are. You may release now."

Jack's face burned with humiliation as he expelled the enema into the container Otis held beneath him.

"Now for the delicate part," Otis said, retrieving a small silver tray from one of the cabinets.

Jack's eyes widened as he saw the items laid out - a straight razor, shaving cream, and various bottles.

"The Duchess prefers her guests to be smooth," Otis explained as he began to lather Jack's groin with the shaving cream.

Jack tensed as he felt the cool touch of the razor against his sensitive skin. Otis worked methodically, removing every hair until Jack was completely bare.

"Now, let's get you cleaned up," Otis declared, retrieving a basin of warm, soapy water and a soft cloth.

Jack gasped as Otis began washing his exposed body, paying meticulous attention to every inch of skin. The gentle touch combined with his vulnerable position had Jack's cock throbbing almost painfully.

Jack bit his lip, fighting back a moan as Otis washed his anus, balls and cock. The man's touch was professional yet somehow intimate, each stroke of the soft cloth sending shivers through Jack's overstimulated body.

After the cleaninng, Otis massaged a fragrant oil into Jack's freshly shaved skin.

Otis selected a small bottle and began applying a cool gel to Jack's most sensitive areas. The substance tingled on contact, making Jack gasp.

"A special blend of stimulants and mild aphrodisiacs," Otis explained. "The Duchess insists her guests be in a proper state of arousal."

"...and this," Otis said as he fitted a silicone glans protector tightly over the tip of Jack's penis, "we can't have you dripping all over, can we?"

Jack's cock throbbed almost painfully as the gel took effect. Every nerve ending seemed to be on fire, sending waves of intense sensation through his body. He squirmed against his restraints, overwhelmed by the onslaught of stimulation.

Otis smiled as he finished his ministrations. "The Duchess will be most pleased with your preparation," he said approvingly. "Now, let's get you presentable for the ladies."

Otis rotated the frame until Jack was vertical. Then he moved the bolster from in front of Jack's stomach to behind him and rotated Jack face down with his butt high and his legs spread.