Cathy's Vacation

by Dodgerfan

Email Feedback | Forum Feedback

© Copyright 2008 - Dodgerfan - Used by permission

Storycodes: FF/m; bond; chain; trunk; fem; tattoo; hum; toys; reluct/nc; X

Cathy worked for a very controlling Boss. She was forced to wear tight micromini skirts, hot pants and short tight latex dresses. Cathy talked to her lover and a plan to take care of her Boss was hatched.

Cathy decides the best way to control the Boss is to collect evidence of the sexual harassment. Cathy began to record his sexual comments and to take pictures of his sexual advances. She would make sure that a Secretary was always close by with a digital camera. This went on for a month. Cathy would now have complete control of Paul’s life.

Cathy’s lover is a lawyer she had all the documents prepared. She cameminto his office wearing a trench coat and carrying a briefcase and suitcase.

"Why are you dressed in these clothes? You know my terms of employment only tight fitting clothes no coats."

"Paul those days are history I’m in charge now. If you don’t agree to my demands? I will file a sexual harassment lawsuit. I have pictures and tape recordings of your behavior."

"What are your demands?"

"You must sign all these documents."

"Where do I sign?"

"At the bottom of each page."

" What have I just signed away?"

" You have signed a statement that you are guilty of sexual harassment. The second one says that you’re quitting. The third one says that you will give every Secretary a pay raise. The forth one says that I get a four week vacation all expenses paid by you."

"Strip and be quick about. Everything nude I’m in a hurry."


"No more talking open your mouth." She quickly shoved a leather crop in his mouth. "If that leather crop hits the floor twenty times on your butt?"

She opened the suitcase which contained handcuffs, rope, chain and locks. She removed her coat to reveal a sexy policewoman outfit. Cathy had on a police officer shirt with a short leather skirt.

"Up against the wall hands on top of your head. Spread your legs wide. Wider! That’s better." She slowly began a strip search. Every part of his body was searched. She then took her nightstick and slowly moved it beneath his cock. "Now you know how I felt every time you touched by body. Give me your right hand and now your left." She tighten the handcuffs around his wrists. "Put your legs together."

Cathy tighten handcuffs around his ankles. Next Cathy began to tightly wrap chains around his body. She would put locks every place that would keep the chain extremely tight. Once satisfied she took a handcuff and put in around his cock and balls. Then she made him hop to the door and handcuff him to the door.

" Paul I suggest you don’t struggle too much. You wouldn’t want to damage your balls. I need to buy some clothes and adult toys for our trip." She pinched his butt and spanked his behind. "Back up I’m in a great deal of hurry to begin our trip."

Paul slowly moved back to open the door for Cathy. Cathy was in the elevator when she remembered she needed his gold card for shopping."

"Paul open the door I forgot your gold card."

She again pinched and spanked his behind. "Don’t forget if that leather crop hits the floor it's twenty times on your but. Paul have a nice day I know I will."

For the next two hours every Secretary gave Paul a pinch and a spank on his behind. Some came back four or five times. Others would take the leather crop and whip him repeatedly.

"Paul open the door," Cathy entered with two trunks. "Paul I have a bunch of presents for you. I’ll think I’m going to change your bondage. I have some leather straps and a ball gag for you."

Cathy removed the chains and replaced them with leather straps. She next put an armbinder over his leather straps.

"I want your elbows to touch. I just need to pull these laces a little tighter fantastic. Paul, open your mouth like a good boy for me." She tightened the ball gag till his eyes looked like they would pop out.

"Paul it’s been a long day goodnight." Cathy took hold of his balls. "Paul I suggest you stay awake tonight you don’t want to lose your balls." Cathy pinched and spanked his behind. "Goodnight Paul see you in the morning."

Paul had a very difficult night in his bondage. If he fell asleep the pain from his balls would awaken him. Most of the night was spent trying to stay awake. As the Sun began to rise Paul felt that things could only improve.

"Paul open the door I need to get you packed away for our trip."

Paul slowly moved back his legs could barely move from standing up all night.

"Paul lets get your handcuff off of the door. Lie down on the floor, I’m going to put you in a tight hogtie. I've brought some breakfast for you."

Cathy removed his gag and put a bowl in front of Paul. She opened the trunk and removed it’s contents. Paul quickly finished eating his food.

"Could I have something to drink?"

"Paul I’ll put some water in your bowl. I’ll be back in an hour to pack you up for the trip."

"What do you mean by pack me up?"

"Paul that’s too much talking." Cathy put a penis gag in his mouth and tighten the leather strap. Cathy left the room and locked the door.

Well at least I’m not attached to the door. I’ve never thought she was capable of such a great plan. I can’t ask for help from anyone or my wealthy wife will find out about my sexual advances. She told me when I married her if I ever kissed another woman. I would be left with nothing. The prenuptial agreement was ironclad. My only chance is to go along with Cathy’s plan. Hopefully after the four weeks I will be set free.

Cathy began to remove the leather straps. She replaced each leather strap with rope. The rope was extremely tight and secure. When she was done I was in a tight hogtie. Cathy had tied a thin cord around my cock and balls. She then tied the cord around my wrists. She hogtied me by tying my elbows to my feet.

"Do you need to use the bathroom?"

Paul shook his head yes.

"Christine I need your help. Help me lift him up hold him while I get the bucket."

Cathy shoved the bucket under his cock.

Christine and Cathy put Paul in the trunk.

"I need a trunk shipped to the Hilton hotel room 237 in Lake Tahoe."

The delivery man picked up the trunk. As he was wheeling Paul away every Secretary stood up to applaud.

When Cathy and Mary arrived at the hotel they decided to relax by the pool. Cathy and Mary were madly in love with each other. They began to kiss and hug passionately. "Let’s go to our room and make love."

They arrived at their room to find the trunk had been delivered. Cathy securely tied Paul to the bed post. "I need a massage table sent to room 237."

While waiting for the table to arrive. They began to kiss and use vibrators on each other. Poor Paul couldn’t even get to enjoy their lovemaking he’s head was tightly strapped to the post. He’s sexual frustration was to much for him to deal with. Paul struggled to break free from the ropes. But Cathy’s knots only tighten the more he struggled.

A knock at the door Cathy wraps a towel around her to answer the door. "Just set it up the table over here."

Mary laid down on the massage table. Cathy began to slowly massage Mary.

"Mary his penis is erect we have to do something about that."

Cathy got a bucket of ice and stuck Paul’s cock into it. Once his cock was soft Cathy tightly tied a thin cord around his cock and balls. She then pulled his cock down between his legs and tied the cord securely to the post. Cathy began to kiss and massage Mary for two hours. Mary then gave Cathy a very sensual massage.

" Mary I have an idea. We need to securely tie Paul to the massage table."

They untied his legs and put Paul on top of the table. With Paul’s arms still tied behind his back. Cathy tied each ankle to the table leg. So his legs were spread wide open. Cathy began to tie his chest to the table. Cathy whispered something to Mary and then they got dressed. Mary began to laugh hysterically. Cathy and Mary left the room.

Paul wildly struggled to loosen the ropes. The harder he struggled the tighter the ropes became. Paul began to wonder why she laughed like that. Paul would soon find out. Cathy entered the room with some packages. She walked over to the table and she began to run her fingers thru his hair. Cathy then plugged in a hair trimmer. Cathy was cutting off all of Paul’s hair. Mary started covering his cock and balls with shaving cream.

" I suggest you stay quite still. I wouldn’t want to cut your cock and balls." She moved the razor slowly around his balls and cock. "Perfect now for your legs." After his hair was all gone Cathy shaved Paul’s head.

"I need a tattoo artist sent to room 237 as soon as possible thank you."

They untied Paul from the massage table. Cathy retied his ankles and knees. Paul had to hop to the bath tub. Once Paul was in the tub Cathy dumped three buckets of ice on him. Paul made a futile attempt to get out of the tub. "You do that again and I’ll hogtie you."

Cathy turned on the cold water. He again made a futile escape attempt. "You asked for it!" Cathy turned Paul over and tightly hogtied him. As the water rose Paul would struggle to keep his head above the water.

Cathy shut the water off. "You relax while I get out of these wet clothes."

Cathy came back in the nude. Cathy held Paul’s head above the water and she finished giving him a bath. After releasing him from his hogtie. Paul hopped to the massage table. Cathy strapped his head to the table. She then strapped his chest and legs. An hour later the female tattoo artist arrived.

"Why is he strapped to the table?"

"He hates needles! Here is a list of what we want done to him."

"That'll cost 900."

"Here’s his gold card. How long?"

"About six hours"

"Call my cell phone when your done." Cathy and Mary went to dinner and a movie.

When Sally was finished she called Cathy. "Cathy I’m finished he looks very beautiful."

"Thank You I’ll be there in an hour."

Cathy and Mary entered the room to find Paul face down on the table. His behind said 'slave Pauline' with a picture of a nude man in a hogtie beneath the words. Cathy lifted his face to reveal her beautiful work. Sally had transformed Paul into Pauline.

"Sally you do fantastic work give yourself a 500 dollar tip."

"Thank You goodnight."

"Goodnight Pauline it’s late were going to bed."

Paul’s life that he knew had ended. He was now forever more Pauline. The tattoo artist had made a permanent makeover. His lips were bright red with a dark colored lip liner. His eyebrows were shaved off and replaced with permanent female eyebrows. She also gave him permanent eye makeup. She also pierced his ears and put some large hoop ear rings in his ears. The ear rings were permanently soldered together. Pauline struggled all night to escape from the leather straps. Sally had tighten down the straps with incredible strength. She wanted to be sure he couldn’t move while she worked.

"Room service I like breakfast for three sent to room 237 as soon as possible."

Cathy and Mary were in the shower when the the breakfast came. "Bring it in were in the shower."

The female room service attendant entered with the breakfast. "I need you to sign for this."

Cathy wrapped a towel around her and came in the room.

"Wow his makeup is exquisite."

"Sally the tattoo artist did it last night."

" If you glue some breasts on him it would be perfect!"

"I will thank you for the idea. Would you like to go to a party tomorrow night?"

"I would be delighted."

"Do you have a leather catsuit"


"What size are you"

"Size 2"

"Meet us here at 8:00 pm tomorrow"

"Enjoy your breakfast"

Cathy removed Pauline’s leather straps. She then hogtied him on top of the table. She put the food in front of Pauline.

Pauline had to wriggle forward to reach the food. "Could I have some juice." Cathy put a straw in his juice. After Pauline finished eating Cathy helped him go to the bathroom. She took hold of his cock so he could use the toilet. Cathy had complete control of Pauline’s life!

After Pauline was done using the bathroom he hopped to the table. "Lie down on the table." Cathy began to spread super glue on his chest. Mary pressed the breasts to his chest for ten minutes. Cathy spread more glue on his head and Mary attached a blond wig to his head. She bent Pauline over the table and spread his legs wide. Mary began to tie each leg to a table leg. Cathy tied his chest to the table.

Cathy and Mary left the room with big grins on their faces. Pauline made a valiant attempt at escape. The ropes only tighten more securely. Pauline would soon know the reason for their grins. Ten minutes later Cathy and Mary came back in wearing hotpants and go go boots. They also each had strap on dildos.

"You call it heads or tails" Cathy flipped the coin in air. "Heads I get the tail". Mary hopped up on the table. She scooted over to Pauline and took off the penis gag. Mary immediately stuck her strap on dildo in Pauline’s mouth. Cathy went to the tail and she began to shove the strap on dildo in with gusto. "Pauline just relax and enjoy it we will!" After an hour they changed positions.

"Yehha riddem Cowgirl Yehha!" Cathy and Mary took off their strap on dildos after four hours of great sex. Mary shoved the penis gag back in his mouth." Let’s take a nice hot bath together." Cathy tighten all the knots just to be safe.

After the bath Cathy untied Pauline from the table. Cathy put a hobble skirt on Pauline. She put a coat over his bound arms to hide his bondage. Cathy and Pauline were going to take a midnight walk. She put a short tight latex dress on for the walk. They found the streets mostly deserted. Pauline needed to be exercised he’s been in constant bondage for two days. Pauline was struggling to walk in the hobble skirt. He could only slightly move his legs. Cathy became impatient with his slow pace. "Pauline you better walk faster or I’m going to whip you." He attempted to walk faster but with the hobble skirt on it was not possible. Cathy began to whip him with her leather crop.

Two hours later they entered the room. "Do you need to use the bathroom?" Pauline shook his head yes. Cathy removed the hobble skirt and high heel shoes from Pauline. Cathy held his cock in her hand while he used the toilet. This is my chance to escape my legs are untied. When he was done he tripped Cathy with his leg. Cathy fell to the floor. Pauline made a run for the door. He turned around to open the door and ran as fast as he could. Cathy got up and grabbed several coils of rope.

"That SOB going to get it now!"

Pauline was an amazing sight running down the hall. He was nude hands and elbows tied behind his back with a set of breasts. There was a room service cart in the hall. Pauline pressed the elevator button. The elevator door opened and Pauline was about to step in. Cathy threw her lariat at Pauline. "Gotcha you know you can’t escape from me." Cathy quickly hogtied Pauline and with the help of Mary placed him on top of the cart.

"Room service I need ten buckets of ice sent to room 237." Pauline was put in the bath tub. "Hold him up while I put ice beneath Pauline." Pauline was going to have a very uncomfortable long night! He was covered in ice. The only part of him uncovered were his two big toes. Pauline rocked from side to side to keep warm. "You try to escape again and I’ll hang you from a tree by your balls!" Cathy checked to make sure the drain was open.

Cathy awoke from a good nights sleep. She went into bathroom to check on Pauline. He was sleeping all the ice had melted. Cathy shook Pauline awake. "I need to get everything ready for the party." She released him from the hogtie. "Room service I want three orders of breakfast sent to room 237." Pauline used the toilet while Cathy held his cock in her hand. Cathy hogtied Pauline on top of the table. She put the food in front of Pauline. He quickly ate the food.

"Can I please have some water." Cathy put a bowl of water in front of Pauline.

Mary and Cathy decided to find a sexy outfit for Pauline to wear to the party. Mary put Pauline in a leather hobble skirt, leather corset and a leather bra. The bondage was also all leather. Leather straps for his arms and leather cuffs with a three inch chain for his ankles.

"Mary I love to see Pauline in leather and bondage hands behind very sexy It’s missing something? I know a posture collar perfect."

Cathy put Pauline in a short tight latex dress. The bondage was all steel. His hands and elbows were handcuff behind his back. His ankles were also in handcuffs. "Cathy Pauline looks very sexy I would add a cock cuff for his cock and balls."

Mary put Pauline in a French maids outfit. The bondage was only rope. His hands were tied together in front. She also tied his elbows and knees.

"Mary I would prefer the hands behind the back. You could attach a tray to his waist."

" Why choose will take all three and change Pauline into the different outfits."

Mary held him while Cathy stripped and tied Pauline.

"I need to buy a leather catsuit for Susan the room service waiter." Cathy strapped Pauline to the bed post. Cathy and Mary left the room.

"Room service it’s me Susan" Susan entered the room. She decided to wait for Cathy and Mary to arrive. "I see Cathy took my advice the breasts look great"

Cathy and Mary arrived with the leather catsuit. "Susan lets see how it looks on you? Exquisite it fits like a glove."

Cathy released Pauline from the post. "Pauline you need a cold shower." Cathy took him into the shower and turned the cold water on. Pauline tried to hop out of the shower. "If you move again I’ll give you another ice bath?" Pauline stayed put for the rest of the shower. Cathy slowly washed his cock balls butt and the rest of his body. After Pauline hopped out of the shower Mary dried him. Mary and Susan held him while Cathy untied his arms. They left his legs tied. Cathy put a short tight latex dress on Pauline. Cathy applied the handcuffs on his wrists, elbows and ankles. Mary lifted the dress to put the cock cuff on Pauline.

Cathy and Mary took a long sensual shower. They dried each other and then put leather panties on each other. Cathy and Mary had a very intense kiss. "We need to get dressed were going to be late for the party"

The elevator door opened to reveal three women in leather catsuits and Pauline in his short tight latex dress. Cathy hit Pauline with her leather crop to get him to walk faster. The Secretaries had started the party. All the Secretaries wore fetish attire. Two were dressed in short rubber dresses. Another one had leather hot pants with a leather corset. The Secretaries had rented a yacht for the party.

"You all look so sexy in those outfits." All the Secretaries crowded around Pauline. "He looks incredible well he got exactly what he wanted " They attached a tray to his waist and Pauline began to serve drinks. Every time Pauline would serve a drink to a Secretary. He was getting spanked or groped. Susan lifted his dress and tighten the cock cuff. After an hour they changed his outfit to a hobble skirt, leather corset, posture collar and a leather bra. "It’s time to get this party in overdrive."

Cathy, Susan and Mary took Pauline away so they could strip and tightly bind him. A half hour later they carried a table into the party. Every Secretary began to applaud. Pauline was bound nude and bent over the table. His legs were spread wide and tied to each table leg. Cathy had a strap on dildo in her hand. "Who wants to be first?"

"I want to be first. I asked him for a raise and he said go screw yourself!" Christine took the strap on dildo from Cathy. She put it on over her leather catsuit. "Wait put a condom on the dildo." Christine gripped the sides of the table and began to slowly thrust the dildo in and out. Pauline was going to get what he always wanted. He was going to have sex with every Secretary. They also would be dressed in all his favorite outfits.

After every Secretary and Susan had sex with Pauline. Cathy Mary and Susan replaced Pauline’s ropes with wet rawhide. He was hogtied on top of the table with wet rawhide. "That was the best party I’ve ever been too." Everybody went to their cabins to sleep. "Goodnight Pauline"

When the Sun rose in the sky Pauline’s rawhide began to dry. The rawhide began to tighten all over his body the pain was unbearable. It would be a very long day for Pauline. The Secretaries put on string bikini some went swimming and others sunbathed. Cathy put suntan lotion on Mary. Christine put suntan lotion on Pauline while spanking his butt. Susan feed Pauline some fruit and eggs. He asked for some water and Susan gave him some. "Do you need to use the bathroom?"

" Yes I do" Susan and Christine untied his legs and took Pauline to the bathroom. Susan held his cock so he could use the bathroom.

Christine held Pauline while Susan replaced the rawhide with leather cuffs on his wrists, elbows and ankles. Susan locked a chain from his wrists to his ankles. Christine attached a tray to Pauline’s waist. Pauline began to serve breakfast to the Secretaries. Mary took the plate and then she pinched his butt. Cathy hit Pauline with her leather crop and he fell on top of Christine. "Pauline you must be punished! " Christine tied a rope around Pauline’s ankles and then she raised Pauline to the top of the mast. Pauline twisted in the wind for five hours.

Cathy and Mary took the Secretaries to the airport. "When you get back I need you to get the address of the Secretaries and email them to me."

After Pauline was lowered down Cathy, Mary and Susan dressed him in a hobble skirt, leather corset and a leather bra. Susan put leather straps on his wrist and elbows. Mary put an armbinder over the leather straps. Cathy finished off the bondage with a posture collar. Pauline would have to walk back to the hotel. Cathy and Mary took turns whipping Pauline with the leather crop. Pauline tried to keep up with Cathy and Mary. But with the hobble skirt walking was very difficult. He could barely move his legs. Finally the hotel was in sight.

Mary strapped Pauline to the table. "Goodnight Cathy, Goodnight Mary" Cathy and Mary made love for two hours and then went to sleep.

"Could you have Susan bring three breakfast to room 237"

Susan brings in the breakfast into the room. Susan released Pauline and then hogtied him on top of the table. She removed the ball gag and put the plate in front of Pauline. He ate the food quickly. "Susan could I have some juice?" Susan put a straw in a glass of juice for Pauline.

Cathy and Mary came out of the bathroom wearing policewoman outfits. They had on a policewoman shirt with a short tight leather skirt. "Susan in the bathroom is another policewoman outfit. Please put it on for us."

Susan went into the bathroom to change. Pauline was stripped and stood against the wall. Cathy shoved a leather crop in his mouth. Susan came out of the bathroom in her police woman outfit. "Put your hands on top of your head. Spread your legs wide. Wider! That’s better." Cathy took her time searching Pauline. Finally she took her nightstick and slowly moved it between Pauline’s legs and cock. Mary was next she took hold of his cock and balls. "If you give us any trouble? Will hogtie you and put you in a bath tub full of ice."

Susan put her hands all over Pauline. She held his cock in her hand and whispered something in Pauline’s ear. Cathy handcuff his hands and elbows. Mary handcuff his ankles. Susan put thumb cuffs on his thumbs and toes. Cathy wrapped chain around Pauline’s body. She put locks every place that would keep the chain extremely tight. Susan took the leather crop out of Pauline’s mouth and gave him a kiss. She then put a ball gag in his mouth and gave him another kiss. Cathy and Susan put Pauline inside the trunk.

Cathy checked her email for the Secretaries address who had been fired by Pauline. He would become a boss chain letter. When the Secretary was done with Pauline. Each Secretary would chain him and send him to the next name on the list. Cathy filed her sexual harassment lawsuit. Pauline’s wife made a out of court settlement to Cathy. Cathy and Mary were able to live out all their wildest dreams. Susan asked to be on the list. Susan and Pauline lived out all of their bondage fantasies.

You can also leave feedback & comments for this story on the Plaza Forum