Secretary job (F/M)

[Boocola]

Gary is playing his Playstation 4. He is playing Dead or Alive 5 last round using Kasumi, the outfit she is fighting in is black thigh high stockings and a black and white teddy. His fingers is moving on the controller left hand gripping the left side of the controller with the thumb moving a joystick with right hand gripping the right side of the controller with his thumb pressing buttons. The Kasumi the woman on the screen is in a fight against another woman dressed as a maid her name is Kokoro.

Gary controlled Kasumi to do a double cartwheel kick forward. The CPU controlled Kokoro blocked both attacks and counters by low sweeping kick, medium roundhouse kick and high roundhouse kick. After getting hit with the sweep, he managed to block the medium and high kick. The he makes Kasumi jump backwards doing a somersault kick hitting Kokoro after landing he spams the punch button Kasumi unleashes a fury of hand knife edges at Kokoro knocking her out. "Lay down!" He exclaimed with excitement.

His mother Karen entered his room. "Keep your voice down." She told him.

"I'm playing a game." Gary said playing his game. "I am almost done."

"You're done now." Karen said unplugging the system.

The game shut off and Gary just stared at a blue screen. "Why did you do that." He said as he kept staring at the blue screen. "Now I have to wait for the system to repair itself the next time I play."

"I pay utilities for you to play." Karen said. "I'm cutting the electricity until you get a job and pay rent."

"I looked for a job and the only thing available is for women." Gary said as he got up got his cellphone and showed her.

Karen took his cellphone. "Secretary..." She said. "...is that all you could find?" She asked.

"The only requirement is typing..." Gary said "...I can do that."

"Son,it's not that easy..." Karen said "...you might have to make coffee or print copies." She said looking through his cellphone. "How about stocking at the supermarket."

"Absolutely not my friends shop there." Gary said.

"Fine..." Karen said. "...you're eighteen." She said with a scowl. "You want to be a secretary, I'll help you get the job."

"No, I didn't say I wanted the job." Gary said.

"Well, I need you to start helping out with payments around here." Karen said.

"What if I get discovered posing as a woman just so I can get a job?" Gary asked.

Karen looks at her son. "Either you dress up as a woman or go apply for a job at the grocery store." She said crossing her arms in front of her chest. "Or I'll get you out of my house."

"I'll take the secretary job." Gary said getting up from his gaming chair. "Okay, I am going to apply for the job." He said grabbing his car keys and walking to the front door.

"Aren't you forgetting something." Karen said.

"No, I am just going to get an application." Gary said.

"Dressed like that." Karen told him.

Gary looked at his blue jeans, black shirt and white shoes. "What's wrong with these clothes?" He asked.

"For one..." Karen said. "....you're look like a man."

"I am one, mom." Gary said grabbing his keys. "I can say I am picking it up for my sister."

"No." Karen said. "You have to go as a woman."

"Mom, I'll be back with the application." Gary said.

"I'll get the application online..." Karen told him. "...I'll download it while you're in the bath tub." She said. "I have body wash you can use on your body and face, don't put it on your head."

"So you are going to make me a woman..." Gary said. "...good luck." He said putting his keys down and walking in the bathroom to draw the bath water.


One week later

Gary arrives for his first day of work as a secretary. He is wearing a white blouse over a stuffed bra. A brown skirt over nude pantyhose with heels on his feet. His mother taught him how to put on makeup to make him look like a woman. He is carrying a purse with extra makeup if he has the touch up his face. If he wasn't so nervous he would be scared out his mind. He changed his voice so he could pass as a woman. He picked Peggy for his girl's name.

Gary walked into the office for the first time seeing a bunch of women dressed like him. "Hello..." He said in a feminine voice. "...I'm Peggy Thompson, I'm the new secretary."

A woman looked at him with scepticism. "You are replacing Tina." She said pointing to a desk in a cubicle. "That is you cubicle, all the information you need is in the computer on the desk." She instructed.

"Thank you." Gary said looking at the cubicle she pointed to and started walking towards it.

"One more thing." The woman said. "The woman you work for has a fetish." She said. "I would give three to one odds that you don't last."

"What do you mean I'm just here to take notes and type." Gary said.

"Good luck with that." The woman said. "My name is Nancy call me if you need advice." She said.

Gary sat down at his desk turned on the computer for the instructions. He read the instructions and they were alot what he prepared for some of what he didn't know how to do. "Oh crap." He whispered to himself.

All of a sudden a woman strolled out of the elevator wearing a white dress, tan pantyhose and white high heels. "Nancy has my new girl arrived yet?" She asked.

"Yes Mrs. Smith." Nancy said.

"Good, have her meet me in my office with a pad and pen to take notes." Mrs. Smith said opening a door and entering her office.

"Peggy..." Nancy said "...you heard her get in there with a pad and pen.

"I don't have a pad of paper or a pen." Gary said.

Nancy walked over with a pad and pen. "Here use mine..." She said. "...you owe me." She said.

"Okay." Gary said wondering what that meant grabbing the pad and pen walking into Mrs. Smith office. He stood there looking at Mrs. Smith.

"Well don't just stand there like a stupid man..." Mrs. Smith said. "...take a seat."

Gary was confused he thought she discovered who he is, but took a seat, sitting with his knees together. "Yes ma'am."

"I require you to be ready to take notes at all times." Mrs. Smith said. "Wait a minute..." She said getting up and walking around to look at him sitting down. "....stand up and turn around."

Gary got up and turned around, he saw Nancy staring at him as Mrs. Smith walked over to shut the door. "Sorry ma'am..." He said. "...I forgot to shut the door."

"After all this time..." Mrs Smith said. "...I never had a man in this office."

"I can explain..." Gary said. "...I needed a job." He said.

"Well, I must admit whoever helped you become a woman did a fantastic job." Mrs. Smith said. "I have a challenge for you." She said walking back to Gary. "I gave the same challenge to my former secretary, she wasn't any good at it." She said reaching him.

"I'm up for any challenge this job has to offer." Gary said.

"Very well..." Mrs. Smith said. "My challenge is I tie you up and depending on how fast you escape the bigger the bonus." She said looking at him up and down.

"What about taking notes for you?" Gary asked.

"Well, I would write down my ideas while you are struggling to escape." Mrs. Smith said. "If you escape before I'm done with those notes the bigger the bonus." She told him. "If you don't escape an hour after I'm done taking notes you receive no bonus I release you to type a letter with my notes."

"Okay, I accept your challenge."Gary said.

"Very well..." Mrs. Smith said. "...keep your eyes forward." As she walked around her desk getting rope out of her drawers. "Put your wrists together behind your back." She ordered Gary to do. She tied his wrists together behind his back then took the pad and pen from him. She pinned his arms to his torso by tying rope above and below his fake breasts. The walked him to a floor mat.

"I'm going to struggle on that mat?" Gary asked.

"Unless you prefer the hard floor to roll around and struggle on." Mrs. Smith said walking over to her desk to grab more rope and a ballgag. "Get on your knees." She told Gary as she walked back to him.

"Okay." Gary said getting down on his knees struggling not to fall over because his hands are tied behind his back

Mrs. Smith dropped the rope and placed the ballgag in his mouth fastening it behind his head. "I take it this hair is your real hair not a wig.

"Mmmph." Gary said yes with the ballgag in his mouth.

"The purpose for the gag is that you don't talk." Mrs.Smith said tying his ankles, calves and thighs together with rope. "So shut up and struggle to escape." She said pushing him down on the mat then she went behind her desk and started writing her ideas on the pad of paper while Gary struggled to escape.

Will Gary get the bonus or fail?
To be continued...

[Boocola]

Gary is laying on the mat struggling to escape by using his arms, he never been tied up before and doesn't know how to escape. He tries not to drool with the ballgag in his mouth, but swallowing his saliva gets harder and harder. He glances at Mrs. Smith who is busy writing down notes that he's going to have to type in a letter. His arms are getting worn down from struggling, so he started struggling with his stockinged legs trying to get the ropes lose. Until he hears Mrs. Smith makes a sound of frustration. "Mmmmph mmmph?" He asked her what was wrong stopping his struggling to look at her sitting at her desk.

Mrs. Smith glared at him like she forgot he was there. "Writer's block." She told him in anger opening up her drawer and getting out a paddle. "You know it's not polite to speak with your mouth full." She said getting up to walk over to him with her paddle in her right hand. "Although I do appreciate your concern, I am still going to punish you for speaking with your mouth full." She said bending down. "Oh don't worry this room is sound proof." She said pulling up his skirt and spanking his buttocks once.

"Mmmmph." Gary said ouch because it did hurt. "Mmmmph." He said as ouch again as she started spanking him. He tried to keep count as his face grimaced three, four, five then on the sixth one tears started to drop from his eyes.

Mrs.Smith stopped spanking Gary on the seventh spanking when she notices tears swelling up in his eyes. "First time being spanked?" She asked him.

Gary shook his head. "Mmmph Mmmmph mmmph." He says it just hurts.

"You want a tip to help you escape..." Mrs. Smith said "...it will only cost you thirty minutes." She said setting the paddle down by Gary's face.

Gary nodded. "Mmmph Mmmmph." Saying yes please.

"Try using your wrists." Mrs. Smith said walking back to her desk getting back to work. "Thanks for the inspiration." She said sitting back down to write down her ideas.

Gary had to wait a couple of minutes until his eyes stopped swelling up and the pain in his buttocks went away. He started feeling uncomfortable laying on his stomach, so he rolled over and sat up. "Mmmmph." Saying ouch as he sat up his buttocks still hurts.

"You might want to avoid sitting up on for a while." Mrs. Smith said with a giggle.

Gary had a look of frustration as he stayed sitting up dealing with the pain as he pulled at his wrists to no avail. "Mmmmph." He muttered to himself as he thought about needing that bonus because he didn't think he was going to escape before Mrs. Smith got done with her notes. He threw himself back on his stomach in frustration both arms and legs struggling and saliva getting on the mat.

Ten minutes later Mrs. Smith was done with her notes and Gary still layer there on the mat still struggling with drool in front of him all over the mat and on her paddle. "Easy Gary..." She told him. "...I'm done with my notes." She said. Do you want me to untie you now so you can get to work typing out a letter from my notes or do you want to attempt the thirty minutes escape time."

Gary stopped struggling with frustration in his eyes and sweat on his brow. "Mmmmph mmmph." He said thirty minutes because he needs the bonus.

"Okay, have it your way." Mrs. Smith said as she brought her chair closer to the mat and looked at her watch.

Gary saw Mrs. Smith sit down crossing her legs looking at her watch again. "Mmmmph." He grunted to himself wondering if he was missing something with using his wrist looking at the paddle he thought about baseball and how he would rotate his wrists with the swing. "Mmmph mmmph." He says as he got an idea he tried rotating his right wrist and then his left wrists trying to create a gap to pull his thumb free.

"Twenty minutes left." Mrs. Smith said calmly from her chair as she watched Gary struggle.

Gary almost had his right thumb free as he kept rotating and pulling. "Mmmmph mmmph." He muttered a response to Mrs. Smith saying Twenty minutes left. He rotated and pulled his right hand free. He then pushed the ropes on his chest over his head. He layed there with a rope around his left wrist, a ballgag in his mouth with his ankles, calves and thighs tied together.

"Ten minutes left." Mrs. Smith said. "You're almost there."

Mrs. Smith's voice snapped Gary out of his rest, he untied his thighs first, then his calves and his ankles then unfastened the ballgag from the back of his head. "There..." He said untying the rope on his left wrist. "...all done." He said breathing hard.

"You had five minutes to spare." Mrs. Smith said uncrossing her legs getting up walked to her desk getting two one hundred dollar bills out of her purse and grabbing the note pad and handing the money and the note pad to Gary. "You might want to freshen up before you start copying me notes." She advised him.

To be continued.

[BoundTightly]

Very good story, I'm tempted to become a cross dressing sectary

[Boocola]

Gary walked out of Mrs Smith's office with sweat ruining Peggy's makeup. There's two kinds of restrooms a women's restroom and a multi gender restroom. He grabbed his purse and then went into the multi gender restroom to be safe from trespassing. He looked in the mirror to wipe off the sweat and too touch up his make up, then Nancy enters the restroom.

"Well, looks like you left that office early." Nancy said. "Tina, the woman that you're replacing been in there a lot longer." She said. "I'm curious what happened in there."

"I took notes for Mrs Smith's ideas..." Gary said in a feminine voice touching up his makeup. "...nothing more, nothing less."

"I don't believe you." Nancy said.

"Believe what you want to believe." Gary said finishing touching up his makeup.

"I'm supposed to believe that you could take notes faster than Tina..." Nancy said. "...I don't think so." She said. What really happened?" Nancy asked suspiciously curious.

"I only took notes." Gary said.

"Having to touch up your makeup was an side effect." Nancy said. "I don't think so."

"So it was hot in her office." Gary said walking out of the restroom and to his desk to type the notes. He sat down to type spotting Nancy giving him the evil eye the rest of the day.


At the end of Gary's shift he finished typing Mrs Smith's note. He got up to go to his car grabbing his purse before Nancy stopped him. "Can I help you Nancy?"

"I want to invite you to a get together with the girls that work at this office." Nancy said. "Do you want to come?" She asked.

"No sorry." Gary said. "I want to go home." He said wanting to play video games when he got home, but he doesn't want to tell Nancy that.

"Come on, Peggy it would be fun." Nancy said. "We go skinny dipping in my pool."

Gary thinks that he definitely doesn't want to go. "Truth be told, I want to play video games." He said as he started walking to the elevator.

"What your handle?" Nancy asked. "Maybe we can play together."

"I would rather not." Gary said as the elevator opens and he steps inside. He is glad to be going home so he can get out of these clothes. He thinks that Nancy is a chatter box that quiet down.

Nancy stepped on the elevator. "Come on give me your gamertag..." She said. "...gamer girls need to stick together."

What is her problem Gary thought. "Never really thought of me as a gamer girl just a regular gamer." He said.

"You have to think that being a gamer girl is something special." Nancy said. "It would be fun playing together."

"I don't think so." Gary is now feeling guilty because he wants to play as himself not as thus alter ego his mother created just o get him out of the house. "We'll see." He said as the elevator opens and walks to his car.

Thirty minutes later Gary drove up in the driveway turned the key to shut his car off, grabbed his purse and got out. He walked up to the door. Before closing the door he spots a car parked in front of his house. Ignoring the vehicle he closed the door. Then there was a knock at the door and the doorbell rang.

"Who's that?" His mother Karen asked coming out of her room.

Gary looked through the peep hole and saw it was Nancy. "Oh man." He whispered.

"Well who is it?" Karen asked.

"It's a woman from work." Gary answered. "I can't show her my room, do you have an idea on what to do with her?"

"I have an idea..." Karen said. "...open the door." She said as she went to the garage to get something.

Gary opens the door to see Nancy smiling at him "Nancy what a surprise..." He said "...you followed me home."

"Yes..." Nancy said. "...I figured you can show me you gaming set up."

"Come in, come in..." Gary said looking at her purple shirt, black skirt and black stockings with high heels. "...do you make it a habit following new employees home." He said closing the door.

"Oh no..." Nancy said. "...this is my first time." She said. "So where's your room?"

Karen walked out of the garage with a bunch of rope and two ballgags. "First..." She said. "Let's play an escape game."

"What's this Peggy..." Nancy said. "...your mom is pretty kinky." She said. "Like Mrs. Smith." She said putting her wrists behind her back. "I'll go first."

"Okay..." Karen said."...this one's has spunk." She said setting the rope on the dinning room table grabbing a long piece of rope. She started tying Nancy's wrists behind her back bringing the rest of the rope up to wrap around below and above her breasts. "There now the ballgag."

"I'll get the ballgag mom." Gary said picking up the ballgag placing the ballgag in Nancy's mouth and buckled it behind her head.

Karen got three pieces of rope to tie up Nancy's ankles calves and thighs. "I have you dear..." She said holding her arm. "...I need you to bounce to the living room."

"Mmmmph mmmph mmmph." Nancy said okay I'll bounce. Bouncing making her breasts bounce up and down. Then Karen set. Her down on the couch.

"Now it's your turn Peggy." Karen told Gary.

Gary turned around placing his hands behind his back. "If you insist mother." He said.

"That's a good girl." Karen said grabbing some rope to tie her son's hands behind his back, above and below his fake breasts. "Now for the ballgag..." She said grabbing the ballgag. "...I can't have you screaming for help." She said putting the ballgag in his mouth fastening it behind his head.

"Mmmmph mmmph mmmph." Gary said it's too tight.

"Deal with it sonny." Karen said with an evil tone as she lead him to the living room. Then went to get more rope came back to finish tying his ankles, calves and thighs together then pushed him on the couch. "Okay, whoever escapes first gets a prize." She said walking over to Gary's purse and going through it finding two hundred dollars.

Gary saw his mom going through his purse and taking his money. "Mmmmph mmmph mmmph." He said he wanted to buy games with that, but his mom pretended not to understand. This was the second time that he got tied up today and wondered if he will ever get to play video games.

To be continued.

[Boocola]

Nancy is bound and gagged on the couch apparently there's something no one wants her to see. She gets an idea to get Peggy to help her out of this trap.she wants to see the room. "Mmmmph mmmph mmmph?" She asked if she could help untie her.

"Mmmmph mmmph." Peggy agrees to help. Then the two bound women puts thier backs together. She feels the ropes and finds the knot. It took a few tries but she freed Nancy's hands from behind her back.

Nancy removed her gag. "Thank you very much." She said untying the rest of the rope on her body and legs. "Unfortunately for you I am going to check out your room." She said walking to the first door. "This is not a room of a lady, this is a boys room." She said looking at Peggy bound and gagged on the couch. "I'm going to lift up your skirt."

"Mmmmph mmmph mmmph." Peggy called help momma help.

Karen came out of her room. "Of course it's a boys room..." She said. "...it belongs to my son, who is not here at the moment."

"Where's your son?" Nancy asked.

"You're a nosey girl ain't ya..." Karen went to open the door. "...I think you should leave my house."

"There's something fishy going on and I'm going to figure it out one way or the other." Nancy said walking out to her car


Gary is bound and gagged in his female work clothing, he feels like a fool after being tricked into helping Nancy escape her bondage trap. His mother is standing there with her hands on her hips. He knows that look on his mother's face she's about to lecture him for being stupid.

"Are you proud of yourself." Karen said. "You almost blew it." She said scolding him.

"Mmmmph mmmph mmmph." Gary said that his boss knows he's a man.

"That may be true..." Karen said. "...but the other women don't know." She said "you're going to remain bound and gagged until dinner or until you can escape..." She said turning back to her room. "...you need the practice, so you can escape faster to get a bigger bonus."

"Mmmmph mmmph." Gary complained because he wants to play video games. He attempted to twist his wrists, but couldn't. He sat up on the couch trying to twist his wrists again, but still couldn't move. "Mmmmph mmmph mmmph mmmph?" He yelled trying to ask his mom where she learned to tie people up like this.

"Your uncle..." Karen yelled "...was a boy scout, he practiced tying knots with me." She said without leaving her room

Gary was able to remove the heels on his feet. He tried to get comfortable on the couch by laying down stretching out his bound legs. He tried twisting his wrists again this time he moved a little, then tried again. The knot kept getting tighter as he twisted, he was being fooled again by the knot.

Two hours later, Karen decided to cook dinner she leaves her room seeing her son still bound on the couch. "I am better at tying than your boss." She said to her son.

Mmmph Mmmmph mmmph." Gary says I suppose so.

"Perhaps I should hogtie you while I cook dinner." Karen teased.

"Mmmph." Gary said no.

"Have you gave up trying to escape?"" Karen asked.

"Mmmph." Gary said yes.

"I'm going to cook dinner." Karen said approaching the couch untying a knot on Gary's wrist. "Now untie yourself." She said as she watched her son free his wrists, taking off the ropes wrapped around his body then removed the ballgag.

"That was interesting." Gary said untying his thighs, calves and ankles. "That was kind of relaxing."

"Now you can change..." Karen said. "...dinner will be ready soon."

Gary went to his room to change his clothes for dinner.