Note: Elaine rewrote this for me to show the differences and asked me to post this . I am happy to repost Caught part one as she put so much work into it.
As all ways feel free to email me Debra002@hotmail.com

 

Caught               by: Debra Rachel             rewritten by: Elaine

 

Bob had just walked in the door when his mother called him, "Bob is that you?"

"Yes mum, it's me," Bob replied.

"Come upstairs right away," his mother yelled at him. She sounded angry. Bob slowly and reluctantly went up the stairs wondering what was wrong that she was so angry.

"In your room," she called as he reached the top of the stairs.

When he got to his room he hesitated at the door. There on his bed was all his femme clothes and his mother was holding them up with a look of disgust on her face.

"BOB!!!" She shouted, "what the hell is the meaning of all these clothes?"

Bob leant back against the door his heart heavy. He didn’t know what to say, he just hung his head down tears falling from eyes.

"You promised me you would never do this again!" his mother said sounding angry. "Explain to me where you got these from?"

Bob struggled to speak, unhappy that she had found his clothing. "I…. am sorry."

His mother seeing the dejected look on her son decided to calm down a bit.

"Bob we have to talk about this," she said in a controlled and calmer voice. "Is this what you want?"

Before he could reply she continued, "You want to dress like a girl? Do you want to be a girl? You need to tell me how you feel son."

Bob was stunned that his mother should ask such questions. He enjoyed dressing in female clothes and despite her warning the last time that real men don’t wear dresses he had continued his passion for female finery. He quietly struggled with words, "it's something I enjoy."

She stood up and approached him, "tell me I need to know, have I done something wrong? I know its been hard with your father not being here and living with your sister and I."

"No Mum, it's not your fault," Bob replied.

"Remember the last time when your sister found out about your dressing before and how she made your life a misery for weeks. You know that she will kill you if she finds that you have been wearing her clothes."

"Mom it's nothing that you have done, I don’t know how to explain it. It's just that it feels so right when I wear them. Like it feels natural. "

"So that's it then you are one of those transsexuals." His mother's worst fears confirmed by his last statement.

"I honestly don’t know, but when I see a pretty girl I get jealous of her because she is a girl and I am just an ugly boy. I get jealous of Catriona when she goes out at night," Bob replied.

Bob’s mother just looked at Bob, then tears started rolling down her face.

"Mum what’s wrong?" Bob asked suddenly worried.

"Its nothing " she replied then she said, "get down stairs and do your homework, I need to think about all this."

When Bob's elder sister Catriona came home from her work, her mother took her through to the sitting room and then told her what she had found in his bedroom.

"I'll kill the little sod," Catriona said immediately after learning what had happened.

"No there is a deep seated problem here, it is not going to go away. He really feels unhappy as a boy and I think he needs our love not our hatred," Mum replied at Catriona's show of temper.

"Yes you could be right, he promised he wouldn’t do it again and now look what has happened. Maybe we should help him see what a silly foolish idea it is being the way he is," Catriona replied calmly again. "What bugs me is that he has to take my clothes."

Mum smiled, "well I think mine are just a little too big for him but I'm sure my clothes have been disturbed. Despite all his promises it is not going to go away. He will dress up whenever he can."

Catriona thought about it for a moment and then she announced, "Why don’t we make him see that being a girl isn't so great, you know letting him see that it takes effort to apply make-up and choose a wardrobe."

"Well we could try," said Mum, "what would you have in mind?"

"We could insist that he dress as a girl all weekend. If he wants to be a girl that will soon make up his mind."

"I'm not sure about that Catriona," said Mum, "what if he likes it?"

"What's to like, he can come shopping for food, and do all the ironing, washing up and cleaning around here while he is dressed. I mean he can hardly go out and play with his pals wearing a skirt can he?" Catriona laughed.

Mom thought about it and nodded her head, "it might just work, it would also let him see things as a girl not just dressing up and playing at it."

"OK, I’ll dig out some of my old clothes that should suit him, he'll either be in paradise or regret this for a long time to come," said Catriona and then added, "my wardrobe was long due for a clear out anyway."

"We must make sure that he doesn’t feel ridiculous and we must treat him like a girl the whole time," Mum replied.

"It's going to be fun having a wee sister instead of a nerd of a brother," Catriona smiled.

"Remember this isn't a game Catriona, we have to take this very seriously, Bob needs our love and understanding not our hatred," Mum said trying to ensure that Catriona would treat this as a serious exercise.

"Yes Mum, I have a hard day tomorrow so I'll see you in the morning," said Catriona and they kissed good night.

A little later Mum went to bed still wondering what she should do. She decided one thing that was that she needed professional help to deal with this problem.

The next morning instead of her usual Saturday morning sleep in, Catriona was up early and began to coax Bob up out of his bed.

"Come on Bob wake up," she stroked his cheek gently.

Bob opened his eyes and wondered what she wanted.

"Come on Bob we're going to have some fun today," Catriona said, "you are going to love it."

Rubbing his eyes, Bob yawned and then asked, "what do you mean?"

"Mum told me that you haven't stopped your little hobby despite your promises and we both decided that we should help you," she continued in a vague manner.

"Oh no, She didn’t, why did she tell you?" Bob asked concerned that his secret was out to Catriona.

"Don’t worry Bob, you want to dress up in girl's clothing then fine, you can do that. I've even selected an outfit for you," said Catriona pointing to the dress on the chair. "I picked out a sundress for you as you can see the sun is shining."

Bob thought, 'Oh my god, what's she going to do to me!"

"Come on, Bobbie," said Catriona "you want to be a girl then that's what you'll be but once we start you don’t go back to being Bob again until tomorrow."

"You can't be serious?" He asked suddenly aware of the implications of her last statement.

"Perfectly serious, your hot perfumed bath is waiting sis," said Catriona, "so come on get out of bed."

He rose and walked into the bathroom and stood up in front of the toilet seat to pee.

"Sorry Bobbie girls always sit, so you must too now, besides you won't have to clean up the missed spray later," she smiled enjoying his expression when he re-lowered the toilet seat and sat down. "When you are done, into the bath and I want you to shave your body, legs and armpits."

She handed him a razor as he sat down in the deep perfumed water. He looked at her as though she had grown horns on head.

"Shave," she commanded, "you'll be wearing tights and a dress and I don’t want any hair to be visible."

He lathered his legs with plenty of bath soap and started to shave his legs.

"When you are done, wash and condition your hair too," said Catriona.

He found his legs were smooth after removing his thin fair hair from his legs. He didn’t have much hair elsewhere but dutifully stroked it across his body. He didn't need to shave his face and just got on with washing his longish hair. He had resisted getting it cut despite his mother's objections.

When he got out of the bath, he dried himself using a soft fluffy towel instead of his usual hard one. He strolled into his bedroom and was stunned when Catriona threw him a pair of pink frilly panties to wear.

"I can’t wear these!" He exclaimed.

"Why ever not?" asked Catriona . "Girls wear them and you are a girl today."

He conceded her statement and started to step into them. As he did so his little penis started to get hard.

"Ah a picture always tells a story," said Catriona sensing that he did indeed enjoy the satin panties. "We will need to do something about that unladylike bulge in your panties later."

Catriona passed him a matching padded bra and a pair of tights and she asked," I'll leave you to put them on, I'm sure you know how."

He completed the task and sat waiting on the bed until she returned with a hair dryer and brush. She started to dry and style his hair and soon had it looking full and bouncy. His usual greasy hair was soft and distinctly feminine.

"You face is a mess, we need to use a face cleanser on your nose and chin to clean out those pores," she said in passing before going to get his sundress.

He stepped into it and found her assistance in zipping it up disconcerting.

"You don’t have much cleavage Bobbie but then like Mum and me we don’t have much up top. We'll just slip a little cotton wool in there for now. Who knows you might be able to grow your own one day."

The idea made Bob wince but he said nothing.

"Sit at my vanity and I'll be with you soon," she continued.

Bob loved the feel of the dress and his legs rubbing together as he walked through to her room. He dutifully sat down and crossed his legs and looked at the make-up that lay in front of him. He had played with it before and had often made a mess. Now he was going to have a proper lesson in make-up. He felt his heart flutter.

She brushed his hair when she rejoined him.

"I've just told Mum you'll be ready in a few minutes," said Catriona. "Now then look up and down when I tell you."

"Why?" He asked.

"I'm going to do your eyelashes, silly," she said.

Then she took the blue black mascara wand and applied it to his upper and lower eyelashes.

"Now sit back and relax," she said. He did just that and closed his eyes.

She pulled out some of his straggly eyebrow hairs and trimmed the others much shorter with nail scissors. She put on some cream foundation and finally a little pink lipstick.

She looked at his nails and fortunately found that he hadn't cut them in a few weeks. She took an emery board and filed them into a rounder shape before applying two coats of pink translucent polish.

"Stand up," she commanded when she was done.

"What's the matter?" He asked as he faced her.

She stood back and looked at him and gasped, "I thought that you might look pretty, but you are gorgeous!"

"What do you mean?" Asked Bob.

"Just take a look in the mirror," she said and then shouted "Mum come here a moment."

Bob looked in the mirror and was amazed at what he saw! He saw this beautiful girl who looked very like Catriona staring back at him. When he moved so did she, he gasped when he realised that he was that pretty girl in the mirror.

"Now then put these on," she commanded handing him a pair of brown sandals with a modest wedge heel. "These should be easy and comfortable to wear all day."

Just then his Mum entered behind them and her mouth opened, "oh my god, you are beautiful. Bob you are like a swan."

"It's Bobbie now," corrected Catriona.

Mum gave Bobbie a hug and they went downstairs.

 

(continued)

 

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