Dressing Eileen
by All These Roadworks
Dressing Eileen
Story by All These Roadworks (2021).
Author's Note: If you enjoy this story, please support its creation with a purchase from my e-store. I have a range of hypno-erotica e-books, other stories, and membership plans available! (Click here to view the store.)
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When Eileen attended Greg Bentley’s hypnotherapy practise, she claimed to be seeking treatment for her fear of air travel.
However, Dr Bentley could see that her real problem in life was that she was a rich, entitled bitch, who didn’t know that realise that her curvaceous body and irritating personality made her fit only to be a submissive fucktoy.
He took her into trance, promising to address her phobia - and, to be fair, he did address that, as he was a professional, after all - but while he was there, he did a little extra work.
Specifically, he made her forget how to dress herself. And he increased the sense of shame and humiliation she felt when anyone saw her tits or cunt. And he gave her the idea that he, Dr Bentley, was the only one who could help her with her newfound difficulty.
He sent her home after the treatment, unaware of what had been done to her, and he expected to receive his first phone call from her the next day - if not that very night. But the call did not come, at first, and he began to believe that his hypnotic suggestion hadn’t taken hold.
But two days later, his phone rang, and it was Eileen on the line. Her voice sounded small - meek, confused, and not at all like the superior bitch who had walked into his office.
“Please, Dr Bentley,” she whispered. “I need your help to… to put my clothes on.”
When he arrived at her house, he found her wearing a filmy see-through lingerie bodysuit and a pair of high heels. She hadn’t even managed to get the nightgown on properly - it was falling off her shoulders, and her left breast was fully exposed. She blushed as he stared at her naked tit.
“I’ve been trying for two days to dress for work,” she explained, nearly in tears. “And I just can’t seem to get my clothes on. I don’t know what’s wrong with me. I just knew that no one else could help me - and I couldn’t bear for anyone to see me like this… so I called you.”
“Something must have gone wrong with our hypnotism session,” he told her. “Why don’t you have a seat over there, and I’ll take you down into a trance, and we’ll see if we can fix this?”
She agreed eagerly, her face filled with hope. She sat obediently, and dropped into a trance almost immediately. But Dr Bentley had no intention of fixing her embarrassing problem.
He started by adjusting her clothes, to expose her other breast, and then pulling up the crotch of the bodysuit until it nestled lewdly between her pussy lips.
Then he went to work on trapping her further in her predicament.
First, he deepened her sense of shame. He told her that women who let men see their tits or pussy were sluts, and sluts were disgusting and shameful. Sluts deserved to be humiliated, and sluts deserved to have bad things happen to them. No nice girl let a man see her tits or pussy - that was something only sluts did. He made her whisper the words back to him, like a mantra, and told her that she would continue to whisper those words to herself any time she was alone, without realising that she was doing it.
Then he deepened her vulnerability. The more she was unable to dress herself, the stupider she would feel - and the stupider she felt, the less she would trust her own judgement, and the more she would accept the viewpoints of others without question - particularly the viewpoint of her trusted hypnotherapist, Dr Bentley.
And every time she asked Dr Bentley for help, she would become more unable to dress herself, or make her own decisions about what she should wear. It would be a self-reinforcing cycle.
And finally, just to make sure she continually found herself needing help, he suggested that when anyone asked her to take off any of her clothes - no matter who they were, or where she was - she would obey without question.
When it was done, he brought her back up out of trance.
“I can’t fix your problem, Eileen,” he told her. “The issue is that you seem to *want* to have trouble with dressing. Part of your subconscious *wants* to be naked and helpless.”
“That’s not true!” objected Eileen.
“If you wanted to dress yourself, you could do it,” he told her. “If you don’t want this, then put your clothes on properly.”
But she couldn’t. She fumbled helplessly at her outfit, but somehow was unable to cover either breast, or extricate the crotch of her bodysuit from her cunt. Her face was bright red - knowing that she was showing off her tits to Dr Bentley, and that she was therefore a disgusting slut.
Dr Bentley sighed. “Stand up and undress, Eileen.”
She obeyed, immediately, her blush going even brighter red as she stripped off the lingerie until she was completely nude.
“Would you like my help in dressing you in a work outfit?” he asked her.
She was silent for a moment. She was acutely aware of the power relationship in the room - her naked, helpless; him staring at her tits with more than professional interest.
But eventually she answered. “Yes, please,” she whispered.
“Then give me a kiss,” he told her.
She paused again - then hopped forward, quickly and planted a peck on his lips.
It was enough for now.
He went to her wardrobe, and dressed her in what she said was her normal work blouse and skirt. But he gave her no panties, and no bra.
“If you went to the toilet and pulled down your panties,” he told her, “you might have difficulty pulling them back up. Better to go without.”
He gave her no explanation for the missing bra, and she didn’t ask for one. He sent her off to work, and went back to his own office.
That evening at 7 pm he called her on the phone. When she answered, he said only, “You must undress now, Eileen,” and then hung up.
The next morning she called him again, once again seeking help.
She was naked when he got there. She had tried to put on a pair of panties, and ended up stuffing them halfway into her cunt instead.
He took her back down into trance, and strengthened the idea that this was all her own fault, that it was something she secretly wanted, that these things were happening to her because she was secretly a disgusting slut.
Then he told her if she wanted his help to dress her, she had to kiss him again. But when she gave him a peck on the mouth, he told her to try again, properly. This time she kissed him with an open mouth, and tongue, her naked tits pressing against his chest, and he accepted it as sufficient.
He dressed her in work clothes again - without underwear - but this time he gave her a test. He was going to cut the buttons off her blouse, he said. If she really didn’t want to be dressed like a slut, she would try and stop him.
She didn’t try. She whimpered, clearly wanting to try - but unable to interfere in his choices about dressing her. He used scissors to cut all the buttons off her blouse, until it wouldn’t close in front, and then sent her off to work. He enjoyed the way she was forced to desperately clutch at the front of her blouse to avoid exposing her tits.
He called her again at 5 pm, just as she would be leaving work, and said, “You must undress now, Eileen.” Ten minutes later, she called him back, begging for his help. She was trapped in the public toilets outside her work, completely naked and unable to dress herself.
He drove to meet her, but rather than dress her, he merely wrapped her in a bedsheet and ushered her to his car. Then, rather than start the engine, he suggested that she “show her gratitude for his help”, and enjoyed himself as Eileen desperately and passionately made out with him in the front seat of his car for a quarter of an hour, kissing him, rubbing her tits against him, and thanking him for his intervention.
He drove her home wrapped in the bedsheet, took her inside the house, stripped her nude again, and then left.
The next morning he was back again at her house. She was still unable to dress.
“I don’t know why I’m like this,” she whimpered. “I’m such a slut. You say that if I wanted this to stop, it would stop - but it keeps happening. I must be a complete whore.”
“You *are* a complete whore,” Dr Bentley agreed. “Give me a kiss, and I’ll help you.”
She kissed him on the lips, but after a moment, he pushed her away. “Not there,” he said, and pointed downwards - to his erect cock, which he had extracted from his pants. “There.”
She blushed, and dithered - but then, slowly, sank to her knees, leaned forward, and kissed the tip of his cock.
He had intended to let a kiss be sufficient, but the bitch’s lips touching his cock felt too good, and so he reached down, grabbed her hair, and forced her face down on his phallus. His cock slipped into her mouth, her tongue ran up the length of his shaft, her lips touched his balls, she started to gag, and he sighed with happiness as he began to forcefully fuck her mouth.
Soon he was orgasming, ejaculating into her unwilling mouth, and when he was done he released her. Before she could complain, he pulled her to her feet, and then used one hand to feel her pussy. It was sopping wet, as he had known it would be, and he deliberately wiped a handful of her pussy juices over her face.
“Slut,” he spat - and she knew it was true.
He dressed her as he had the day before, in a skirt, a blouse with no buttons, and no underwear. But this time he gave her no shoes - knowing that such a subtle omission would make her feel even more lewdly inappropriate and exposed at her office - and he took the time to rearrange her hair into childish, bimbo-like pigtails.
At 5 pm he rang her and told her to remove her skirt. When she asked for his help to dress again, he declined.
“You didn’t seem grateful enough this morning for my help,” he told her. “I’m sure you can get home by yourself.”
He wished he could watch her scuttling to her car with her pussy exposed, her face flushed with humiliation.
But it seemed to have the desired effect, for when he attended her house the next morning she sank to her knees to service his cock without being asked, working with eagerness and desperation to please him. He pulled out before orgasm, so that he could ejaculate all over her tits. Then, without letting her clean the cum off herself, he dressed her in a tight pink babydoll tee that stretched lewdly over her breasts. The word “CUTIE” was printed over the bosom.
He spread her legs and pushed an internal vibrator up into her cunt. Its humming was distractingly loud and obvious. He put a pair of white panties on her to keep it inside her. And then he gave her her high heels.
“Now go to work,” he told her.
She didn’t want to. She was aware that what she was wearing wasn’t appropriate to wear anywhere in public, let alone to work. She still had cum on her breasts, and it was soaking through the shirt.
But he told her that this was what she deserved for being a slut. “Maybe the humiliation will cure you,” he said. “Maybe you won’t want to be a slut anymore.” And he hinted that if she didn’t obey him, he would stop helping her dress, and she would be naked forever.
She did as she was told, and went to work.
That evening, she called him, in tears. She had been fired from her job. Her boss had called her a slut and a whore. In desperation, she had offered to give him a blowjob to avoid being dismissed - and he had allowed her to give him one, and then fired her anyway.
He told her that he was bored of her, and bored of dressing her, and that she shouldn’t call him again.
In desperation, she pleaded for him to help her - any way he could.
He told her he would give her one chance to retain his interest. She should drive to his place, right now, and make him feel that it was worth helping her.
She arrived within a quarter of an hour, completely naked, and from the moment he opened the door, she was all over him, kissing him, grinding against him, stroking his cock. He fucked her on the lounge sofa, ejaculating into her pussy, and then made a show of still being unconvinced that she was worth his time.
Desperate, she begged him to slap her, rape her, abuse her, act out any fantasy he could think of, if only he would help her conceal her shame.
So he took her back into trance.
He was going to offer her a new job - as his secretary, and as his fucktoy. But he needed to make further changes to her.
First, he primed her to slowly forget that her name was ‘Eileen’. With each day she would find it harder to recall that name, and become slower to respond to it. Instead, she would accept and internalise the new name he would give her - ‘Tits’, which was easy to say and which appropriately summarised her value. She would forever find that new name demeaning and humiliating - feelings that he used hypnosis to amplify, because it amused him to - but she would respond to it, and soon would not question that it was her true name or a name that she deserved.
And then he began to fascinate her on an object - a dog cage, which he kept in the corner of his study. When she saw it, and learned she would now live in it, she would be horrified - but at the same time the hypnosis would make it seem *right* to her, as thought it were the natural place that her life had been leading.
Tomorrow he would take her shopping, and make her try on all the sluttiest and trashiest outfits he could find, and parade them in front of the shop assistants, and he would only buy her the clothes that made her cry. They would be all the clothes she would ever wear from now on.
But tonight, he thought he would enjoy fucking her another two or three more times.
“Wake up, Tits,” he told her, and watched her emerge from trance, blushing at the name that seemed so demeaning and yet so familiar.
He watched her face, and said, “I’ve just helped you, Tits. Are you grateful for my help?”
She nodded immediately, eagerly, desperately. “Yes, Dr Bentley,” she breathed.
“Then why don’t you show your gratitude, Tits?” he told her. “And then we’ll go and show you to your new home.”
And from the excitement with which she moved to sit on his lap, and let his cock sink into her cunt - and from the wet, passionate eagerness of her kisses, and the way she frantically humped against his groin until he once again ejaculated inside her - you would think she really was grateful for everything he’d done.
(END)