Educating Cuckolds Pt. 01

She nodded to the two women in school girl uniforms and they continued with their briefing. At the end of their briefing, we were sent to our rooms. Each of us had a solitary room. On the wall of the room was a monitor. After lights out, that monitor played cuckolding videos of wives being fucked in front of their husbands while they were either tied to a chair, dressed as women, or seated quietly next to the bed / couch / tent / car door / doorway / pool ledge. Each scene lasted about 10 minutes and each one had the same "theme". The wife was sexually satisfied by another man WHILE her husband watched and encouraged her. Some men encouraged the man.

The next morning, we were woke up early and taken on a walk - naked. Everyone was grouchy and irritable but each of us knew why we were there.

We took classes with a lot of role playing.

We had our measurements taken for sizing of women's clothing.

We did self-assessments, wrote essays, and were instructed to write a cuckold fantasy each day.

One question we ALL had was how was kidnapping all of us and taking us to an isolated property going to help us to move forward with this fantasy?

At the end of the first four days, two of the group had been sent home. Four of us remained for classes, walks, and very little food. We were all weak, but completely hydrated. We had learned that we could not talk a lot, but when we did we skipped the pleasantries and compared notes.

At the end of the second four days, two more of the group had left.

Myself and the other "wanna-be" were not treated any worse or any better. Instead of being taken to our rooms, we were taken to the classroom. A new woman that we had never seen before greeted us.

She wore the standard black leather miniskirt, a white see through shirt, black stockings, high heels, and a black lace bra, which was completely visible through the shirt.

"Congratulations." she started. "By now you have figured out that this is not for everyone that thinks it is for them. We learned a long time ago that mental assessments are important to this process. The other four found out the hard way that this is just a fantasy."

I started to clear my throat but was cut off by a scornful glare.

"Tonight, we are grooming the two of you. ALL body hair will be removed. You will be soaking in body oils and conditioning your skin to feel smoother, and more lady like. Its part of the pampering that we mentioned on day one. Your reward for reaching this level." she finished.

We heard the doors open behind us. We were taken to the bath house. We stripped off our clothing and showered. From there, we were rubbed down with hair remover, then scrubbed and rinsed.

After we dried off, we were inspected and then instructed on what and where to shave. Only after we passed inspection we were allowed to rinse off again. After we rinsed off, we were taken to the soaking tubs and submerged into warm vats of oil infused water.

Both of us fell asleep in the waters. After what I suspect was an hour, we were taken to a different room, patted dry and had a pedicure done.

After the pedicure, we were taken to our rooms and instructed to sleep in the nude. The monitors came on after the lights went out. It was a hypnosis video on how to give a good blowjob to a "real man". The video showed several men dressed in women's clothing sucking another man's cock. At first the video was fast and intense, flashing multiple scenes. Then it slowed down, and it showed how much the men enjoyed the sensation of having their cocks in another person's mouth. The video segments got longer, and they showed men dressed in women's clothing truly enjoying the sensation of having another man's cock IN their mouths. At first I was not interested. As the segments got longer, there were women encouraging the men to suck the cock. Some of the women made out with the guy that was getting the blowjob while the other man's head bobbed up and down. Some women held their heads, guiding them down "the path" as they knew what needed to be done. Some men held the back of those heads as their cocks slid in and out of those "virgin" mouths.

Then the video sped up and it was a series of cum shots, in these mouths, on those faces, and all over their clothes. Some swallowed. Some let the cum drip off their chins. Some women licked it off of their faces before dripping it into their husband's mouth. The voice over in the video kept replaying the same words over and over. It was sexy and condescending at the same time. The humiliation excited me so much that I got light headed.

The video slowed down and it showed a man and a woman taking turns sucking a large cock. The woman smiled as she mouthed the words, "GO ON." to her husband. I watched in awe as her husband closed his eyes and opened his mouth. He obeyed his wife obediently, allowing her to humiliate him by having another man's cock IN his mouth.

She lovingly encouraged him to take his cock as deeply as he could. She watched from inches away. The music faded away and was replaced by slurping sounds. Then her sexy voice whispered, "He is so close. Keep going. Let him cum in your mouth. I want him to fill your cheeks with his cum. Please make him cum... for me." More slurping sounds filled the speakers. I watched as this man worked to please his wife's lover, please her, and humiliate himself FOR her.

His wife stood up and her shaved pussy was in the background. The viewer could see it each time her husband's head slid back down the shaft of the cock in his mouth.

With a gentle hand, she cradled the back of her husband's head and helped his tired jaw and aching neck. She French Kissed her lover, holding his head in her other hand, and allowing her hardened nipples to rub against his chest.

Her pussy was getting wet, and her husband could smell it. He opened his eyes and looked up. The camera panned backward, and the viewer could see his wife's tongue and her lover's tongue touching.

The husband could see her pleasure in controlling the situation, and her assurance in humiliating him. He closed his eyes and began moving up and down the length of the shaft faster, keeping his lips tight around this man's cock.

The camera moved in tighter. All the viewer could see was the wife's hips, and her husband's head moving up and down feverishly.

Within seconds, there was a muffled grunt as the lover orgasmed in the husband's mouth. The wife continued kissing her lover. The lover continued to push more and more semen into the husband's mouth, and the husband swallowed each surge the best that he could.

Instinctively, the husband knew when to "let go" of the lover's cock.

The wife kissed her lover and ignored her husband. The husband watched and admired the situation.

When she finished, she looked down at her husband. She smiled at him.

"I think we have found a new talent in the room." she said to her husband.

The husband nodded yes.

The wife smiled. She reached down and held the semi limp shaft in her hands. She lifted it up and told her husband, "Clean his balls off. He needs to go home just as clean as when he got here."

The husband obediently took the balls into his tired mouth and licked them clean while his wife watched and held her lovers head in her arm.

When he was finished to her liking, she instructed him to sit in the chair in the corner of the room.

The wife kissed her lover. She smiled at him. "Tell your friends."

The camera closed out but the monitor did not go off. A familiar face appeared on the monitor.

"If you are watching this part of the video series, that means you have made it to day 10. Tomorrow, you will have a couple of surprises. Training will take a different tone, and a new schedule. There will be no more of these coveralls. UGH." the woman from the plane video said.

She tossed the coveralls aside in the video and then turned her face back to the camera.

"In the morning, you will have an assistant help you get dressed. What you wear in the morning will be what you wear for the remaining few days here at the compound. Tomorrow is busy day in deed, so get some sleep Bitches." she finished.

The video shut off and the next thing I knew, we were getting woke up MUCH later than normal.

We were allowed to sleep in. We NEEDED it.

As I woke up, two women dressed in school girl uniforms entered my room with a rolling wardrobe rack.

I was dressed in lace thong panties, stockings, garter belt, high heel shoes, a ruffled skirt, and a lowcut top with molded breasts in the top.

After I was dressed, locks were attached to metal loops that had been sewn into the fabric of the dress, and the ankle straps of the shoes.

A small breakfast was brought to our rooms. After we had the chance to eat, we were fitted for wigs, then make up was applied. When the girls were finished, I was given a small mirror. I was amazed at the way I looked.

As I held the mirror, a Hot Pink dog collar was wrapped around my neck and buckled. "It really ties it all together." one of the girls said.

Our room doors were both open and we were across the hallway from each other, so we both saw what was happening in each others' rooms.

My dress was hot pink and black. I wore coordinating undergarments and black open toed shoes. Hot Pink was my wife's favorite color.

I had a few seconds to admire my look before I heard a familiar voice in the hallway yell, "NAILS. NOW. Hurry up, our visitors will be here in 45 minutes."

"VISITORS?" I thought to myself.

I was seated in a chair and my nails were painted to match my toes, which coordinated with my clothing.

My fellow inmate had a similar dress style on, but he had bigger arms, so his was long sleeved. His was purple and grey.

As our nails dried, we were ushered into the lobby of the house. As we stood in the lobby, the familiar black van pulled up and stopped. Instead of schoolgirls rushing out to meet the van, nobody showed up. The doors opened and four men stepped out of the van. Rugged men that looked like they just walked off magazine covers like People or the Rollingstone. Men that reminded you of Indiana Jones, college football players, and underwear models all at the same time. We stood at the entry as they walked through the doors and smiled at both of us as they moved with purpose and authority down the hallway into the conference room.

Behind us, the Head Mistress from the plane video spoke in a low tone. "Those men have a place in your lives, and you will find out where that place is in the near future. For now, I want the two of you to wander around the property in your new clothes to "break them in". After their briefing, you will be serving our new guests their lunch by the pool."

The art of the mystery was not lost on the Head Mistress. We took a short walk and returned to the kitchen for a snack. After we finished our snack, the men that had arrived earlier made their way out to the pool. Two of them sat as a table with a pink umbrella. The other two sat at a table with a purple umbrella.

We served them a 3 star steak dinner, cold beer, and cleared their plates when they were finished.

They were then led to their rooms by the other girls in schoolgirl uniforms.

We were taken to the conference rooms where we were instructed to write another fantasy. After we finished writing, we were given a bathroom break and then taken to a portable trailer outside.

Each trailer had two doors. We were both told, "Go in the left door on the trailer, close it behind you, pull the blinds down tight, and to sit in the chair in the middle of the room. That chair faces a wall, do not move the chair. On the chair, you will find a set of headphones. Put them on and push the blue button. The lights will dim and an audio recording will start playing. Listen to it all the way to the end."

We each entered our own color coordinated trailer door, put on the headphones, pushed the blue button, and listened.

I heard the voices of a man and a woman meeting. The man was flirting with the woman. The woman was very receptive of his advancements, and interested in what he had to say. It was exciting to listen and imagine my own wife being seduced by a stranger.

I could feel my own cock strain against my cage. My heartrate was getting faster. My own imagination was getting carried away. Things seemed very "real" for an instant or two.

I continued listening.

The man asked if he could remove her panties.

"Yes." the woman hissed.

She was DEFINATELY horny as hell and wanted him.

The woman asked if she could unbuckle his pants.

"I would like that very much." he said.

I heard the buckle flop around. I heard fabric slide across skin.

The woman gasped. "Oh my God. LOOK AT THAT THING."

The man chuckled. "Do you want to touch it first?"

"UH HUH" the woman said eagerly.

"OH MY GOD." I thought to myself. "This is some intense shit."

"You have very soft hands." the man said.

"You have a very HARD cock." the woman replied.

The woman whimpered after a lengthy pause.

I heard her moan. I could only imagine what was happening.

"I - I'm not going to last too long. It has been a while." she stammered.

"No worries. I don't stop with one orgasm." the man's voice said confidently.

I heard the woman draw a huge breath in. It was followed by slurping sounds and some stifled screaming. "Jesus. That was the fastest I have every came."

The slurping sounds stopped. "You don't have to be quiet if you don't want to be."

The slurping sounds continued.

The woman's voice was louder. Her voice was heavier. She sounded just like my wife in some ways.

The slurping sounds were louder just before I heard the woman say, "oh SHIT...."

What followed that "oh shit" was the sound of water splattering on the floor.

The woman's voice grunting and moaned in pleasure as the sounds of the hottest sex scene I have ever imagined in my head unfolded in my ears.

I did not realize it at the time, but the woman was experiencing her first squirting orgasm, and the man "on the job" was executing it perfectly.

Just as the woman's voice tapered off and she regained control of her breathing, this cycle would repeat, and she was louder than the time before. After three consecutive (and intense) orgasms, she pleaded for him to stop.

Her voice made it so easy to believe it was my wife and a strange man. My cock strained against my chastity device. The more I listened the more my heart raced, the faster my pulse became, and the lighter my head was.

"I need to put that cock in my mouth." the woman's voice said.

The sounds that followed were sexy to me. The man encouraged her, and told her what felt good to him. He complimented her over and over.

"Baby that is SO fucking nice, but I want to fuck that little married pussy of yours. I want to cum inside of you, and show you how a real man fucks a woman to orgasm." the man's voice said.

The sounds that followed painted an intense scene in the deepest creases of my brain.

The struggled to slide his cock inside of her, and she let him know several times over that she needed to pause.

He took that as long as possible, then I heard her squeal quietly as I can only imagine THAT was the moment when he pushed himself all the way into her "tight little married cunt".

She was literally panting, and in between her deep labored breaths, she told him, "DO NOT MOVE."

I heard gentle kissing and deep moaning sounds. Sounds identical to those that my wife made when we first started dating.

Then I heard the man moaning with her.

"You are touching my clit from the inside. I am about to explode." the woman's voice said urgently.

After that, I heard some grunting, and skin slapping skin. After a few minutes of SLAP SLAP SLAP SLAP SLAP..... I heard the woman scream the loudest I had ever heard any woman scream.

"FUCK ME HARDER." she grunted.

The slapping sounds increased in tempo and I heard her cum again, this time she cried out, "Oh JOHN...." as she orgasmed all over his cock.

Shortly after, I heard him grunt loudly. I imagined his hips driving into hers and his balls jumping as he shot a heavy load of semen into her married pussy (aka her tight married cunt).

"FILL ME UP John. Fill up that married pussy." the woman panted.

The man grunted again and the woman moaned.

All I could hear was heavy panting and the name John.

"Jesus fucking Christ. That was the absolute best dick I have ever had." the woman's voice said.

The man's voice replied, "You are one of the tightest pussies I have even been in."

"I'll give you the chance to loosen it up." the woman suggested.

"I would like that very much." The man's voice said.

"Why don't you take my panties?" the woman asked.

"You won't need them?" the man asked.

"Keeping all of this in mind, there isn't much use in wearing them. My pussy is going to be so wet that I will just be wasting my time." the woman confessed.

Her voice sounds JUST LIKE my wife.

The sounds that followed were of John getting dressed, and the woman kissing him goodbye.

I heard a door close, and the recording stopped.

As the recording stopped, the lights in the trailer turned off.

A single red flood light turned on, shining on a spot in the middle of the wall.

I reached for the headphones and pulled them off of my head.

A voice from the opposite side of the wall said, "Stand up. move to the red spot on the wall."

I did as I was told.

As I got closer to the wall, a small door opened. The door was about waist high from the floor.

"Kneel in front of the small door." the voice ordered.

I was not prepared for the events that followed after I curled my legs under my thighs.