tagTransgender & CrossdressersCaught and Hypnotized

Caught and Hypnotized


Author's Note:

First of all, I just want to apologize for anyone wanting the continuation to my other story, it is coming but I'm currently editing my novel so that has taken priority.

While searching for some notes on my book, I found this story I wrote years ago for a friend. I thought it was lost as some files got deleted from my Computer few years back, but I'm thrilled to have found it on an old flash drive and share it with you as it isn't that bad for a first attempt at writing erotica. I hope you enjoy this story as much as my friend did.

* * *

Tim is running late for School, he is frantically getting his things together while a towel is wrapped around his waist as he has just come out of the shower. He runs a hand through his thick wet brown hair and it mentally thinking if he has everything. Gym kit, check, books, check, homework all check. He dries himself off as much as he can, he is 18 years old, 5, 7 with a skinny body making him a constant target with bullies, but he just thinks how they are going to turn out with their poor grades while he studies hard and gets good grades. He turns and sees his School uniform is all set and his socks and... There is no underwear, he goes to his chest of draws and opens the top draw where he keeps his underwear, all gone. How can they be all gone? He grabs his towel, re-wraps it around himself and marches out of the room.

He gets down stairs and sees his mom asleep on the sofa with a bottle of Jack Daniels at her side. He feels pity and anger; his mother has turned to alcohol after his dad walked out on them two years ago. Rather than being strong for him, she fell apart. He feels pity for her but angry at her weakness to stay positive for him. He shakes her awake, she looks groggily at him. "Mom, where is my underwear?"

"Huh? Oh, washing them now." She replies lazily.

Tim can't believe what he is hearing. "Yes, but I had other pairs where are they?"

She again looks at him trying to think hard through the haze of being drunk. "They all had holes in them so I threw them away." She explains.

Tim feels his teen anger get to the boiling point. "Mom, what the hell am I supposed to wear to School if my underwear is currently wet in the washing machine and thrown away?"

She turns to her side to go back to sleep and answers. "Where some of Kate's for all I care."

Kate is Tim's older sister, she left for college a year ago and has refused to come back while her mother is still drunk, around this time she had a sudden growth spurt so her old clothes that don't fit her anymore were left behind while she purchased some new ones. "I'm not wearing Kate's panties to School, I have gym today." He says angrily.

His mom starts snoring as she has fallen back to sleep, he looks at her and considers his options, he could go commando, but he did that once and he felt uncomfortable in his School trousers and that too would be awkward in gym with his balls coming out of his shorts. He goes to the washing machine and it is still whirring away. He decides to check out Kate's draws and sees what he can find. Maybe she has a pair he can pass of as briefs or something.

He goes back upstairs and opens Kate's bedroom door. It is a very pink room with lots of Kate's old toys and School things littering the floor. He sees an old dressing table with a vanity mirror and chair and he walks over to it. He opens one draw to his surprise has a sex toy inside. "Jesus." He says as he sees a vibrator, bright pink and slightly see through. He shakes his head trying not to have a laughing fit and closes the draw. He opens the next to find stockings and garter belts, the next has bras and then he opens a draw full of panties. He thinks Kate must have been frustrated with the growth spurt as these look expensive and a lot are very slutty. He finds lots of thongs, g-strings and very pink or purple panties but none he could pass of as briefs. He rummages through until he finds the only white pair he can find. They are silky and thankfully this pair is not a thong, but they have a lace design on the front. He looks at his wrist watch, he has no time to consider his options or he will be late for School. "Fuck it." He says and puts them on. They fit quite well and he is loving the silky feel on his cock, which starts to go hard. He feels embarrassed and very horny, he knows he must do something about it fast. He pulls out a pink silky pair of panties and then frees his cock and starts to masturbate into the pink one. He groans from the mixed emotions and feelings and cums into the pink pair rather quickly.

He waits for his cock to go soft and puts it back into the panties and throws the other pair to one side, he then goes back to his room to finish getting ready for school.

* * *

Dennis sat in the principal's office looking pissed off, he is 6,1, 18 years old and well built and is tipped to get a Scholarship playing college football, the problem is he may not graduate, it is the last day before spring break and he needs to pick his grades up or he won't get into college, Scholarship or not. The Principal eyes him up. "I hope you understand what this means Dennis. Your whole life could depend on this. I understand you have a reputation as a Bully, that also won't look good on a college application."

"I'm playing Football not a popularity contest." Dennis grumbles.

"Yes but academics are important, even for a Football player. I am also led to understand you are working on a Science experiment over Spring break."

"Yeah, I want to do a hypnosis study. I learned how to do it online but no one wants to help me." Dennis says frustratingly. He wants to see if there is any truth to the study that you couldn't hypnotize anyone into doing something they didn't want to do. But some guy in the UK, Darren Brown, proved otherwise so Dennis wants to try the same, but no one will come forward.

"With your reputation are you surprised? Hypnosis is dangerous and I must implore you to do another study. A good grade will get you enough of a boost to graduate but even after this project you need more. Now I don't want to hear of you bullying anyone, and I want nothing but hard work from you. You can leave, and work hard over Spring Break."

Dennis storms out of the office and nearly runs into Tim.

* * *

"Move it Sissy." Dennis says and pushes Tim hard into some lockers.

Tim feels a shooting pain in his back and then feels emotionally hurt from hearing everyone laugh at him. He watches Dennis storm off and Justin, his best friend, helps him up. "You OK?"

Tim feels tears start to boil after this morning with the panties and Dennis pushing him over. "I'm fucking fed up."

Justin pats him on the shoulder and they march off to class. The day is uneventful, and then after lunch it is Gym class, here Tim feels more afraid than ever, usually it is praying you don't get an unexpected hard on before you have to change as being a teenager you have no control over your cock. Two years ago Justin got hard and everyone saw, it was humiliating for him and Tim thought of everything possible not to get a boner. Today is different, today is making sure no one sees him in panties.

The changing rooms are huge with a shower to the left and a room with Toilet cubicles to the right, he then thinks of a plan. He changes his shirt then mocks needing to go to the bathroom and grabs his shorts and runs for the cubicle. With the door locked his changes and no one sees.

Then after Gym class everyone comes back to change, he has a free so he has time to think, he again mocks needing the bathroom and enters the cubicle. But as he locks the door he realizes he jumped the gun and forgot his pants. He knows he has to wait it out until everyone has had a shower and changed. He waits for what seems like forever and then Justin knocks on the door. "You OK man?"

"Yeah." Tim says thinking quickly. "Listen, I'll catch you up, it's embarrassing but I have had issues going to the bathroom recently and..."

"Ah, so no more man, really please don't. I'll see you later."

Tim waits and then he hears no more voices. He steps out of the cubicle and looks in the changing rooms. They are empty. Posted on the wall in Coach Smith's timetable and no Gym class is in this hour, he breathes a sigh of relief, he has the whole changing rooms to himself. He goes to his clothes and starts to get changed.

* * *

Dennis is talking with his friends and looks at his wrist, his watch isn't on. "Shit, I left my watch in the Changing rooms; I'll catch you guys up."

Dennis goes back towards the changing rooms. As he walks he is still thinking about his hypnosis project and how he can find a volunteer to help him, even his friends don't trust him. He thinks he needs a miracle then he turns to the changing rooms, and he sees Tim.

* * *

Tim bends over in just the panties to reach for his pants when he hears the sound, the sound that makes his body go numb, and the sound that makes his cheeks flash an embarrassing red. His heart thumping he hears the wolf whistle die and he turns to see Dennis, his constant tormentor standing in the door way. "Very nice Tim, I always knew you were a sissy."

Time feels tears of embarrassment about to come and he pleads with Dennis. "Oh god please don't tell anyone please."

Dennis walks into the room laughing. "Why shouldn't I tell them? Give me a damn good reason why you are wearing a sexy looking pair of panties and I'll think about it."

Tim breath heavily and tells him about how his Dad walked out on him, how his mom is now an alcoholic and how she decided to throw away half his underwear and how the rest were washing in the machine. "I had to wear something, it's not by choice." He says pleading with Dennis.

Tim wasn't really looking at Dennis during this time but looking away, but now he sees Dennis, he isn't smiling, he isn't mocking, he just looks shocked. "I didn't know about your Dad, nor that your Mom is an alcoholic."

Tim wipes a tear away. "I don't like to spread it around."

Tim then sees Dennis walk forward and he pats Tim on the shoulder. "Hey, it's OK man. My Mom's sister drank herself to an early grave, alcoholism isn't a joke. I think I have some bull shit going on in my life you forget others have problems too. I'm sorry about your Mom, and about what a rat bastard your Dad is."

Tim smiles at Dennis. "Thanks."

Dennis nods understanding. "Hey, put your pants back on, I promise not to tell a soul."

Tim breathes a sigh of relief and as he puts his pants on his says five words he shouldn't have said, five words that will ultimately alter his life for good. "Thanks, I owe you one."

* * *

Dennis' sympathy for Tim was not a joke, he genuinely felt for the guy, and then Tim said those five words and Dennis froze, He turns to Tim as he is putting his shirt on and tucking it in. "Wait, there is a favor you could do for me."

Tim looks at Dennis looking a little worried. "What?"

"I have a science project that needs doing, I'm doing a hypnosis study but I need a subject."

Dennis sees Tim hesitate. "I'm not sure."

"Please, it may not even work. I just need something for my project; I need this to help me graduate. Please you would really help me out. Hey, I can even make you forget about this shitty day, how about it?"

Dennis watches as Tim struggles with the decision and nods. "I said I owe you one. When do you need me?"

"Are you on a free like me?"

Tim nods and Dennis claps his hands together. "Cool, let's find an empty class room where we won't get disturbed."

Dennis finds his wrist watch and then he leads Tim out of the Changing rooms and just down the corridor is an empty Class room. They go inside and Dennis locks the door behind them. "What do I need to do?" Tim asks.

Dennis points to the teachers chair by the desk in the darkened class room and Tim sits down. "Right, I am going to do a simple induction and see if you are hypnotisable, then we shall see if I can use you in a project." Dennis cleared his throat and thought back to what he read online and he takes his watch off of his wrist and starts to sway it in front of Tim's eyes. He says all the stuff he has to say, he says it in a soothing voice and to his surprise he see's Tim's eyes flutter, and then he sees Tim's head flop to its side asleep. "Tim can you hear me?"

"Yes." Tim says lazily.

"Good, now Tim you find my voice soothing, as I count back from Ten to one, you will fall deeper and deeper into an hypnotic sleep, a sleep so deep you won't have any control of your mind. Your mind will be under my control, anything I say no matter how degrading or how much you won't want to do it, you will still obey, do you understand?"

Dennis feels his heart racing with anticipation as Time says lazily. "Yes."

"Good, ten, nine, eight you feel yourself falling deeper, seven, six, still falling, so deep you won't be able to wake yourself. Five, four, three, you are so deep your mind is open to suggestion, two and one you are deeply asleep and in my command."

"Yes, in your command."

"You will obey only my voice, this is the voice of you master."

"Yes Master."

Dennis walks about trying to think what he should make Tim do, when he thinks back to Tim bending over wearing nothing but the panties, for some reason Dennis gets hard thinking back to seeing that. He has an idea and he unlocks the door and leaves the classroom. He runs for the girls changing room which is empty, and he finds the lost property box. He rummages inside until he finds an old blouse, skirt and a light blue hair band. He decides that's enough and runs back for the class room.

Tim is still asleep in the chair and he locks the door behind him again. "Tim, tell me what you felt when you first put on your Sister's panties."

Tim lazily answers. "I got hard; I had to masturbate into another pair to calm down."

Dennis smiles and asks another question. "Why did you get hard Tim?"

Time shuffles for a bit and answers. "I felt sexy; I have never felt sexy before."

Dennis puts the girl clothes down. "Tim, when I snap my fingers you will awake, but you will still be in a hypnotic trance, do you understand?"


Dennis snaps his fingers and Tim's eyes open. "Tim, take off your clothes except for the panties."

"Yes master." Tim says and starts to take off the clothes. Soon he is standing still in only the panties.

Dennis feels his cock get hard looking at Tim, mixed and confused feelings going through his mind. "Bend over." Tim bends over and Dennis walks behind him and sees his pantie covered ass sticking into the air. Dennis with a trembling hand reaches out and cups Tim's ass. He loves the feel of it, almost feminine in a way as Tim is very skinny. He pulls back. "Stand straight." Tim stands up and Dennis sees that Tim now has a hard on, he must have aroused him from feeling his ass. "When I snap my fingers, you will put on this skirt, blouse and hair band, do you understand?"

"Yes master."

Dennis snaps his fingers and watches as Dennis grabs the blouse and puts it on, he struggle with the buttons being on the wrong side but gets it on, then he puts the skirt on and then puts on the hair band making his hair look more feminine. Dennis is almost shocked by the transformation, he just needs make up and to shave off his body hair and he would be one fuckable slut. Dennis gets a dirty idea and smiles. "Dennis, when I say awake, you will awake from your trance and see you are wearing girl clothes. Then you will be overwhelmed by how sexy you are and you will uncontrollably jizz in your Sister's panties, after you do you will go back into your deep trance, do you understand?"

"Yes master." Tim answers.

Dennis smiles and giggles but he is hard with anticipation as well. "Awake."

* * *

Tim awakes and sees Dennis standing in front of him sniggering. "Did it work?" He asks. He then feels his legs are cold. He looks down and sees he is wearing a blouse and skirt. He is horrified and embarrassed and aroused, very aroused. "What have you...done...I trusted. Oh, god I feel so sexy." He starts to rub his hands over his body. "Yes, I'm sexy, so hot, so...yes, oh god yes." He says as he starts to feel his cock twitch and cum into his sister's panties.

* * *

Dennis is frozen watching Tim have an orgasm in front of him and then go back into the hypnotic sleep. He then smells the musky smell of Tim's cum. Feeling curious he goes to Tim and lifts the skirt. He sees a wet patch on the panties from Tim's cum and the smell gets stronger and Dennis' cock is now straining in his pants. He undoes his trousers and pulls his cock out, he is about to stroke it when he sees Tim and gets another wicked idea. "Tim, get on your knees."

Tim gets on his knees and then Dennis puts his cock in front of Tim's face. "Give me a blow job."

Tim without resistance takes Dennis' cock and puts it in his mouth. Tim starts to suck and move his head up and down along his shaft. Dennis can't believe how well he is doing it; he even starts to use his tongue along the bottom of the tip of his cock. Dennis groans and he hears Tim make a noise as he gag reflex is kicking in but he still sucks his cock eagerly. Dennis can't take it anymore and grabs Tim's head to keep him there and shoots his load into Tim's mouth. "Swallow it." He says and he hears Tim swallowing all he gives him. He looks down and sees some of his cum coming out of the sides of Tim's mouth, he smiles and pulls his cock out and some gets Tim in the face. "Clean yourself then clean my cock with your tongue."

"Yes master."

Tim uses the blouse to wipe his face clean, and then licks clean Dennis' deflating cock. Dennis puts his cock back in his pants and tells Tim to put his clothes back on. As he does this, Dennis has a thought; his parents have gone on vacation today for the Spring Break week as he is 18 and can be legally left on his own, Tim's Mom will be so drunk she won't care where her son is for the week. He smiles wickedly and sees Tim has put his boy cloths back on. "Tim, I heard rumors about your Sister, she was a bit of a slut I heard. Does she have Slutty clothes?"

"Yes, I saw some in her room today; they don't fit her anymore since she grew suddenly."

"Tim, here is what you are going to do tonight."

* * *

Tim snapped awake and saw Dennis, he looks around the deserted class room and sees he is wearing his School uniform and standing in the middle of the class room. The last thing he remembers is sitting in the chair. "Did it work?"

Dennis nods. "Yeah, you were under for awhile, School's over man you missed your last class. I struggled getting you out of the trance. You feel OK?" Dennis asked sounding concerned.

"Yeah, I feel great. Listen, I got to go, have a good spring break."

"I'm sure we both will." Dennis says smiling as Tim leaves the class room. On his way home he feels a strong need to go into the Pharmacy and he goes inside. He mindlessly browses the isles until he finds a body hair remover. He pays for it and leaves the store. He gets home and his Mom is passed out on the sofa again. He shakes his head in anger and heads upstairs. He goes straight into the bathroom and starts the shower and reads the instructions on the hair remover. He showers for a bit then applies the Hair Remover to his body. He stands still for awhile until the burning sensation gets to the point of being unbearable then steps back into the shower. He watches as he small amount of chest hair comes off, followed by his pubes, under arm and leg hair. He can't think why he had to do this be he felt it had to be done.

He gets out of the bathroom and instead of going into his room, he walks into his Sister's.

* * *

Tim stops dead in the middle of the street, unsure how or why he got here. He tries to think back, he has vague recollections of removing his body hair and then leaving his Mom a note saying he is staying with a friend for the whole of Spring Break. He feels strange and he looks down to see he is wearing a blue Track Suit and sneakers and he is dragging a suitcase behind him. He feels a wedgy going up his crack and he feels something soft underneath the tracksuit. He shakes it off and carries on walking until he sees a big house up the street. He doesn't know why but he walks up the drive to the house and knocks on the door.

Report Story

byMiles63© 30 comments/ 254523 views/ 150 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: