Mentoring a Cuckoldress Pt. 02

I stood in my home office holding Carmen's panties in my hands. I had a shit eating grin on my face that sandpaper could not remove. I was pretty proud of myself. I was not expecting this strong of a response and I was very pleased with the results.

I held her panties to my face and took a deep breath through my nose, savoring her scent on them. My grin turned into an uncontrollable smile.

I was looking forward to this summer term. I wanted to text her. I needed to call her. I knew better on both fronts.

What I knew was that she had to find her own way through the initial period. She had to set the boundaries she wanted to impose on her husband and SHE had to decide how far things would go.

I had done my part in the process. If I had to guess, I would say things were going to move in the direction I had anticipated and Carmen would eventually cuckold her husband. There was no reason to feel guilty about anything at this point. It was what the husband wanted. I hoped he was ready. The very idea seemed to entice Carmen and (since I was assuming everything at this point) I had made the cut for the "short list" of men that Carmen wanted to fuck, I was definitely rooting for her to be successful at this endeavor.

I looked at my phone. No notifications.

I unpacked by computer and decided to change my clothes before I poured myself a drink and reflected on where I was in life.

"With this goofy grin on your face and a pair of woman's panties in your hands things must be pretty good Jake." I told myself.

ACROSS TOWN ...

Carmen cradled her husband's head as he dutifully ate her pussy. It had been a stressful week and with everything behind her, she was getting an early start on a relaxing weekend.

She had already came once, almost instantly when she thought of Jake touching her. She wanted to scream out his name ... but it was too soon.

She was working on a second orgasm. She could tell her husband to stop at any time, but she didn't want this to stop. She enjoyed the long slow build and the strong wash that those kinds of orgasms made as they rushed over her body. Her favorite orgasm was the surprise orgasm. Powerful. Intrusive. A complete ambush on a woman and pure satisfaction wrapped in complete happiness.

Carmen had gotten really worked up on the drive home. Driving from campus back to her house with no panties on WAS exciting to her. She vowed to repeat this in the future. "Well, maybe I can make it a "Friday Thing" for the summer." she thought to herself.

In hind site, she was wet when she and Jake walked to the coffee shop. She really noticed it when she came out of the bathroom and the breeze from her legs moving under her skirt moved across her freshly waxed pussy lips. The sensation awakened new senses and she felt more alive. This was the strongest sensation of sexual arousal she could ever remember.

It had been months since she had anything more than her husbands tongue between her thighs and she was beginning to notice just how horney that made her. It was difficult to focus on her final exam with Jake sitting inches away from her. When she was in class beside him, she felt aroused by the unknown.

Jake was a man of principles and she respected that. Carmen was a volcano of sexual energy. She recognized all of this and none of it changed her urges.

As her husband did his best to bring her to orgasm, Carmen closed her eyes and imagined herself laying in Jake's bed. An open window with full moon light illuminating everything below. Maybe a gentle breeze that makes the thin white linen curtains sway. She imagined it was Jake's lips and tongue pressed against her smooth pussy lips. She focused on the smell of his cologne, his smile and those calm blue eyes.

A rush of heat passed through her body and her orgasm made her cry out uncontrollably. She aggressively pulled her husband's face into her pussy and worked her hips against his face. The contact between the two made a sloshing sound as her hips and thighs twitched against his face. She could not control her cries of passion. The heavy breathing or the whimpers that followed.

When it was over, she nearly passed out. She slid her leg off of his shoulder and regained her balance by the desk before he noticed. She turned away from him and leaned against the desk for a minute to regain her composure. In more than 20 years of marriage, her orgasms had never been this intense. It frightened Carmen and it confirmed what she needed to do.

She handed her husband some tissues and asked him to fix her a glass of wine for her. He bolted out of the office into the kitchen.

Carmen took a deep breath. She could feel some juices trickling down her inner thigh. It made her smile. She looked at her phone. She thought about Jake. Surely he had found her "token gift" to help him through the short summer break by now. She considered texting him for a long minute. "Not yet." she told herself.

Carmen pulled herself together and pushed Jake to the back of her mind. His advice had hit home with her and made perfect sense. What little research she had found on line fell in line with what Jake told her. He had gained her trust and she was going to follow his advice to the letter.

She walked into the kitchen and started to prepare her husband's favorite meal. She sipped wine and kept finding things for him to do so he was not in the way.

After dinner was in the oven, Carmen ran to the shower and rinsed off. She got dressed in the same top and skirt, but put the bra in a padded envelope and placed that in the pocket of her bathrobe.

Her nipples were still stiff from her orgasm earlier. She HAD calmed down, but not completely. The shirt did not hide her nipples and it would be to her advantage this evening.

Carmen and her husband sat down to a very nice meal. He tried to make small talk, shared some office gossip and discussed the improvements the yard needed. She tried to not come across as a distracted school girl with her first crush, but she was exactly that ... a distracted school girl.

Carmen's husband John had learned to not beg, or nag Carmen when it came to the chastity device. He had almost accepted the fact that his orgasms were no longer under his control. He had come to understand that his behavior hurt her in a way, and there was a price to pay for that hurt. Until tonight, he had accepted the fact that he was not having orgasms on his terms. He was positive that was going to change tonight, so was Carmen. The problem was John was not reading the same script.

John finished his plate and sat patiently while Carmen took her time. John studied her movements and tried to not become aroused by the fact that her nipples were shining through her shirt. A shirt he had never seen before.

John's cock squeezed against the tube. It strained and there was no controlling it. It was painful, but John had gotten used to it. The "promise" that there was some relief in the near future eased the pain.

Carmen had laid down the law ever since John woke up hungover and caged. He had read about husbands that were in chastity for months at a time and he promised himself he would not end up like them. Or would he?

John hadn't quite added it all up yet.

Carmen finished her meal and instructed her husband to clean the kitchen.

"I am going to go get the bedroom ready for our ceremony. Don't be long." Carmen teased.

John feverishly cleaned the kitchen, loaded the dishwasher, ran the trash out and wiped down the counters. He stood at the end of the hallway waiting for Carmen to call him in. A few minutes passed and Carmen opened the door.

The bedroom was staged just like Jake had suggested. The video camera was already recording when John walked in. Carmen stood in the corner and gave John instructions.

"Take off your clothes and lay in the middle of the bed." she ordered.

Without hesitation, John peeled his clothes off and laid down in the middle of the bed.

Silently, Carmen moved to the side of the bed and handcuffed John to the headboard. John looked perplexed, but wasn't about to risk an orgasm over a foolish question that might change the mood, so he said nothing.

Carmen moved to the footboard and restrained his ankles. She moved to the camera and double checked that John was in the frame. She zoomed in so anyone else watching this video could clearly tell who it was.

Out of the frame, Carmen stepped to the side and removed her top. She wore a gold chain with a small key resting against her cleavage. She walked over to the side of the bed and picked up a 5x8 card.

"Look into the camera and state your full name Sweetheart." Carmen opened up.

John looked at the camera and replied, "John Bailey".

"Do you promise to behave if I remove the CB3000 device?" she asked.

John nodded in response.

"Answer the question verbally Dear, or we will wait another week." Carmen demanded.

"Yes I will behave." John replied.

"Do you promise to follow all of my commands to the best of your ability and if you cannot, do you accept the punishment?" Carmen asked.

"Yes, I promise to follow your commands or accept the punishment." John answered with some doubt in his voice.

"Will you ask permission to ejaculate?" Carmen asked.

"Yes I will." John answered.

"Do you agree to clean yourself up after you ejaculate?" Carmen asked.

John replied, "Yes I will clean myself up."

Carmen smiled with approval. She slipped the skirt off and let it hit the floor. It was the first time in months that John saw her completely naked. It was the very first time he had seen her without any pubic hair. He was getting more aroused than he was this afternoon. Carmen allowed him to admire her.

Carmen let the card hit the floor. She walked around the bed to the back side so she would not block the view of the camera. She kept the chain and key around her neck as she bent over and unlocked the brass lock on John's CB3000. It added to the moment.

John whimpered when he heard the "CLICK" of the lock.

Carmen slid the key out and placed the lock on the nightstand. She slowly removed the chastity device and placed it by the lock. She returned to the "task at hand" and loosely stroked his shaft.

"You were such a good boy this afternoon." Carmen said with a hint of condescension. "Finally gave me a good orgasm."

John said nothing.

"Fitting that it was from your tongue and not your cock." Carmen said, getting the insult bag opened up.

John squirmed a little.

"For doing all of your chores and eating my pussy the way you have been, I want to reward you." Carmen said.

"Is that okay?" She asked.

John nodded.

Carmen laughed. "Do you deserve to be rewarded, slave?"

John caught on real quick.

"Yes Mistress." John replied.

Carmen liked it. She turned her head and smiled at him with approval.

Carmen tightened her grip on Johns cock and started stroking it faster. She smiled for the camera. Her breasts swayed with the rhythm, her nipples were still hard.

"Oh Mistress ... that feels really good to me." John said.

Carmen looked at John. "You thinking about the sounds I was making in the office this afternoon while I was coming on your face?"

"Yes Mistress ..." John panted.

"May I come Mistress?" John pleaded.

"You may not ... Slave. It hasn't even been a Minute yet." Carmen replied.

"Oh NO ..." John moaned.

"DONT YOU COME .. I WILL PUN-" Carmen yelled.

It was too late. John shot a heavy load of cum all over Carmen's hand, his chest and belly.

John panted and grunted while Carmen stoked his cock until he stopped shooting semen all over himself.

"I TOLD YOU NOT TO CUM WITHOUT PERMISSION, SLAVE!!" Carmen yelled.

John looked up, "I am sorry Mistress. Its been so long for me."

"Its going to be even LONGER next time!!" Carmen threatened.

John opened his mouth to make another excuse and Carmen stuck her cum covered fingers in his mouth.

"LICK IT OFF!!" Carmen demanded.

Slave John did as he was told to do. Carmen was pleased and surprised that he was so submissive to her.

"Fucking pathetic." Carmen insulted him again.

She drug her fingers through more of the semen and fed it to John. She made that gesture several times over. "Get used to the taste, Slave." She told him.

Carmen repeated these steps over and over until most of it was gone. During the last "feeding" she told John, "Next time it will be easier."

Carmen looked up at the camera and smiled.

She found a puddle of cum near John's waist and she wiped the last of the cum on John's face and even ran her fingers through his hair to get her hands clean.

"THIS is how you orgasm from now on, Slave." Carmen informed John. "If you refuse to perform like this in the future, I will add a month of chastity to the standard 2 weeks. IS THAT CLEAR?"

"Yes Mistress." John responded.

"From now on, your orgasms will be supervised and you will clean your own semen up after you orgasm. Make sure you do a good job at it too. I don't think I need to explain what hangs in the balance, do I?" Carmen explained.

"I understand Mistress." John replied.

John's cock was still hard.

Carmen iced down his cock until it was soft again. She towel dried his cock and slipped the chastity device back into place. The plastic was cold and intrusive to John.

When Carmen snapped the device shut, John sighed with disappointment. She held the device in place, fed the lock through the loop and then the deafening "CLICK" that signified things were still the way SHE wanted them.

John was almost broken. There were a few more hurdles to clear for Carmen, but she was in the race.

Carmen left John on the bed, tied down. She walked over to the camera and zoomed back out. She looked at the camera, smiled and winked, then stopped the recording. She popped out the memory card and slipped on her robe before leaving the bedroom. She left the door open on purpose.

Carmen copied the file to a thumb drive. She put the thumb drive in the padded envelope with her bra. She pulled the necklace over her head and dropped it in the envelope as well. Then she stuffed a note in the envelope that said, "Hate to break up the set."

She sealed the envelope and addressed it to Jake. She looked at her phone. It was just after 10pm.

A car pulled in the driveway. The doorbell rang. Carmen met her friend Noreen at the front door and handed her the envelope. Noreen had no idea what was in the envelope. The two said nothing. Carmen whispered, "Thank you."

Noreen nodded and left.

Carmen went back to the bedroom and John had fallen asleep. She unlocked the handcuffs and covered him with an extra blanket.

Carmen slept in the spare bedroom. She made a list of changes that would be made tomorrow. She also made a list of new clothing to buy, including the bra and panties she needed to replace.

Jake woke up with a splitting headache. The doorbell was ringing and he stumbled to the entry as the Fed Ex driver was stepping away.

"I'm here!!" Jake yelled out.

The driver turned around and requested his signature for the swollen envelope. Jake smiled as he signed for the package. He recognized the hand writing in the address box.

"Things are about to warm up." Jake thought to himself.

Jake walked back into the house, started the coffee pot and then chugged most of a Gatorade.

He walked back to the bedroom and grabbed his phone. There were SIX test messages from Carmen.

Jake feverishly opened his phone up and opened his text message app.

Carmen was standing in front a mirror. Her hair was pulled up into a messy bun and she wore her black framed reading glasses. She had a sensual look on her face. Jake could tell she was naked, but the pic was only from the armpits up.

The second pic she sent was of her toes, painted Crimson Red (Jake's favorite color). Carmen had purchased a toe ring with the letter J engraved into the band. She was wearing it on her left toe.

"That sends a message." Jake thought to himself.

(Jake didn't realize that Carmen's husband's name was John.)

Third picture was of Carmen standing in front of a full length mirror with her robe pulled off the shoulder. Her hair was down and messy but still sexy. The robe was open but all Jake could see was her shoulder and part of her thigh sticking out the opening.

Fourth picture was of Carmen in front of the full length mirror completely nude. She had her back to the mirror and the phone over her shoulder.

"She has a wonderful looking ass." Jake thought to himself.

The 5th picture was of Carmen from the waist up. She had her arm across her breasts and a "surprise" look on her face.

"Well that is more skin that I have neve seen on her." Jake said out loud.

Jake paused for a minute. He anticipated a full nude shot for the 6th picture. He opened the attachment and saw what he had hoped for all this time. Carmen took a full front al nude in front of the full length mirror. She had repositioned the mirror into the doorway of the bathroom so in the background, the reflection in that mirror was of her ass.

Jake's cock twitched.

He knew that Carmen wanted to fuck him. He knew that she had been physically and emotionally neglected and now that he had provided her a way to ethically fill this void, she was definitely "all in".

John woke up and walked to the bathroom. urinating with the chastity device on was a challenge he had mastered earlier in the week. Now he was starting all over. As he finished, he saw a note on the counter from his wife. He opened it:

SATURDAY CHORES:

Dust

Vacuum

Remove Trash from all rooms

Wash cars / have cars washed

sweep and mop kitchen

clean out fridge

make coffee

make breakfast (Ideas listed in fridge)

Make the beds

Wash and dry dirty towels and linen

SUNDAY CHORES:

Wash and Dry laundry

Cut the Lawn

Trim Hedges

Do grocery shopping

PAGE TWO READ:

"I will need additional time to study this summer because of the condensed classes so you need to pick up some of the slack around here. I will still cook through the week, you will clean the kitchen. I also need time to process our current arrangement. Its not permanent, but its not going to be the way it was before either. I have needs and those needs have not been met in the past. I fault you for not stepping up and being the man I need. It feels like you are not interested in me any more and when I found you beating off in the shower, that confirmed those suspicions. We need to talk about that and a few other things in the near future. For now, you need to earn back some of my trust by showing your level of dedication to us."

C

John swallowed hard. He got dressed and took on the list for the Saturday. He KNEW this would get better, he just didn't know when or how. He knew one depended on the other and all of it depended on him. So he threw himself into it and hoped it would be enough.

As far as John knew, his "secret" was safe and secure on the computer. He knew Carmen had been using the same computer but she had not let on that she had found his pictures of Mistresses or the stories he had read about powerful men that found pleasure in letting their wives fuck other men, sometimes right in front of them. John found himself thinking about his more and more.

"Maybe now is the time to broach the subject?" he thought to himself.

John had his doubts about the fantasy but not about Carmen. "Would she be upset?" Absolutely. he answered himself.

As John carried out the trash, he vowed to find a way around his wife's emotions and bring this up. He knew he was risking the marriage, but he felt this would help explain his behavior.

He wanted to confess to her so badly. He knew a few of his co-workers wanted to sleep with his wife. He thought about arranging that a few times but chickened out at each possible opening.