Teenage Tearaway Tamed – A Novelette

A Novelette


Steve was a young football hooligan from a children’s home. But when he went to live with Jill, a childless widow, it all changed and Steve was to be transformed into a beautiful girl called Samantha…

Jill Withers lived in a secluded house off the main New Forest Road. She was a professional writer in her early forties, who was still attractive but had lived alone since her husband died five years earlier. Sometimes she felt depressed, lonely and less than a woman because she had no children, but the outside world saw only her brave smile.

She helped fill the void by fostering problem children from time to time – she had a good record of success, and it brought in a little extra money too.

The phone rang: “Hello, Jill?” said a voice that she recognised as that of Jeffrey Griffin, a local social worker.

“I’ve got a case for you, if you’re interested. Young tearaway, sixteen, called Steve Bell. He’s at the orphanage, but they’re on the point of throwing him out. Went to court today for football violence and got a £200 fine. Looks like a cherub, but he’s a proper little hooligan.”

“Any offences against women?” asked Jill. “I don’t want a rapist on my hands.”

“Nothing like that – all for football. I can’t make up my mind whether they’re acts of frustrated anger or misplaced loyalty. You can look at the case file when you come to my office.”

Jeffrey came out to greet her as she arrived, ushered her in and gave her Steve’s case file. “Steve Bell, aged 16, nationality British” Jill read as she opened the file. The facts were bleak. Steve was quite an expert football hooligan, had recieved several fines and was presently on probation.

“Makes unhappy reading” she said to Jeffrey.

“If he’s nicked again, they’ll send him down. They’re running out of time and patience. The strange thing is there’s a different side to him that few people see. A quiet, sensitive boy, a very frightened boy. I just can’t get to the bottom of him, Jill. There’s something hidden inside of him that he’s afraid to show the world, something he’s ashamed of.”



Jill always insisted on meeting a client alone. When Steve Bell arrived she was surprised – he was slender and about 5 feet 4 inches tall. He wasn’t just handsome; if he had been a girl he would have been beautiful – what a waste of such looks!!

“Sit down Steve,” said Jill, holding up the file. “Are you really the perpetrator of all this?”

Steve looked sheepish. “Yes Ma’am”

“My name is Jill, not Ma’am,” she said. “Steve, you realise that next time, the people with power are going to lock you away?”

“I guess so.”

Jill sensed his embarrassment. “Doesn’t it matter?”

“Not really. I’ve no job and no home. Who’d care?” he shrugged.

“Then you’re finished, aren’t you? I mean, if you’ve no hope then your life is all but over.”

Steve simply sighed.

“Steve, given the chance, your life could be different.”

He looked at her curiously. “How?”

“You’ll stay with me and work for me. If you don’t like me or I don’t like you then we go our own sweet ways and you’re on your own.”

“What would I have to do?”

“Not a lot. Housework, some gardening and a few chores. You’ll be paid.”

He looked at her carefully. “And what do you get out of it?”

“Enough money to cover your board – and satisfaction if you make the grade.”

“Satisfaction, that’s a joke.”

Jill could see Steve’s need to believe but he was still suspicious. Jill threw the file down on the desk. “In 2 minutes I walk out of this room, with or without your answer. I could be your last chance, Steve. One day, you could have a fight and someone could be killed. Is that what has to happen so you can earn a manly reputation?”

Jill pushed her chair back and made to walk out. “I’ll come.” he said quietly.



Steve arrived at the house two days later, and was impressed by the size of the property. Jill met him at the door and smiled, then showed him into the lounge where there was a sense of calm and tranquillity. It was as if a load was being lifted from his shoulders.

Jill studied her new lodger; he seemed somehow even more beautiful and vulnerable than before. There was a look of longing, pain and sadness in his eyes that made her want to grab him and hug him like a mother.

Jill was amazed at Steve’s ability to amuse himself. Within days of his arrival he became a different person. He was full of thoughtful acts and was surprisingly sensitive, yet Jill still felt that he was holding something back from her. In most things, Steve was quite forward, but something was obviously bothering him.

One morning Jill was driving towards town when she remembered she’d forgotten her bank ATM card. She swore under her breath and turned back. As she climbed out of the car she could hear Steve’s record player. Well, she thought, there was no need to disturb him, she would go straight to her room, find her card and go back to the shops.

She opened the door and then stood rigid with shock. There was Steve, dressed as she had left him, except that he was wearing her high heeled shoes. A large pink bow tied his fairly long hair into a pony tail. He turned round and she immediately saw that his face was made-up like a beautiful girl’s. She felt breathless as she made her way to the bed and sat down.

Steve looked at her open mouthed. As Jill gained her composure she realised he was afraid. This was obviously what Steve had been holding from her all this time. Little by little over the weeks he had been opening up like a beautiful flower, dropping little hints that she should have recognised.

“I think you’d better put some coffee on” she said with a sigh.

“I’ll clean this off,” mumbled Steve.

“No, go just the way you are. I’ll meet you in the lounge.”

“Are you going to tell Griffin?” Steve asked nervously.

“I’m not doing anything until we’ve talked.” She watched him leave the room, amused by the way his high heels made his bottom wiggle, just like a girl’s.

Jill made her way downstairs after recovering from her intial surpsrise. Steve came into the lounge, taking dainty little steps because of the heels on his shoes and carefully balancing the tray of coffee. Jill was amazed at how a little make-up had changed him so completely. What would happen, she wondered, if he wore a dress? How had she missed it all before? She was usually proud of her woman’s intuition, but this time it had let her down.

“Well?” she asked, trying to sound relaxed. “Are you going to tell me everything?”. Steve took a deep breath and fell silent. “I don’t think I can.” he finally said.

“Steve, you have to. If you don’t, I’ve no option but to refer you back to Jeffrey Griffin. More importantly, for your own sake you have to unburden your soul. Trust me, give me a chance to help you.”



Steve sighed and started slowly: “Ever since I was a small child, life has been hard for me. When my mum remarried, my step-dad thought the world of my sister, but me, I was an obstacle. How I envied my sister. How I wished I could be a girl like her, and receive the same care and attention she got. My step-dad made Mum send me off to a home, and she tried to convince herself I’d be better off there. At first she came to see me, but eventually the visits stopped. There were no presents, no cards at Christmas or birthdays.

“I was teased about my looks. I was ribbed for caring about people, about things. That was okay for girls, but not boys. I thought: If this was the case, why wasn’t I a girl? I felt confused, I envied girls, their freedom of emotion, of speech.

“Nobody had time for me or the person inside, so gradually I built a different image, one that was more macho. It got to the stage where nobody ribbed me because I’d punch them in the mouth. I ridiculed any show of concern or care in others, because it had been ridiculed in me. I wouldn’t allow myself to see the beauty of the flowers in the field. I didn’t dare, I couldn’t, yet all the time I envied a pretty girl the clothes she could wear and the way she could live.

“I’d love for a while to be a girl, or to be like one. To let all the barricades come down and see if this is really what I should be.”

Steve paused for a second. His eyes were swollen and he shook with emotion. Jill was stunned by the intensity of Steve’s words and those beautiful eyes, enhanced by mascara, reflecting his pain. He was like a starving child reaching for a piece of bread, and she wanted to soothe away his sobs.

“I have this illusion of feminine purity and innocence,” he went on. “When I was with my mates I didn’t have to see or feel, I just had to be. It was acceptable for me to punch someone’s head in but it wasn’t acceptable for me to feel or dress like a girl. Believe me, it’s not for any sexual reason or because I fancy boys or anything like that – it’s a soul journey.”

He stopped, the tears now plainly visible in his eyes. “I’m mad, aren’t I?”

“No,” whispered Jill. “Just betrayed by people, by society, by yourself.”

She opened her arms and held him to herself, like a mother does her child. Her body ached with the injustice of it all. This was probably the first time in his life he had confided his thoughts and feelings to anyone. How could she betray him to Jeffrey Griffin, however good a friend he was?



“What will you tell Griffin?” asked Steve.

“Nothing yet, not until we’ve got things sorted out.” She managed to compose herself. “I’m going to town – I’ll be a couple of hours or so.”

Jill spent nearly four hours in town. When she returned she was laden with parcels. “Could you give me a hand and take these upstairs?” she asked. Jill sighed as she put the parcels on the bed. She tried to be natural, but was nervous as she rummaged in her bags and came out with a high-legged teddy, all in royal blue silk with inch-wide lace trimming. There was a matching pair of panties and a bra.

“I’ll go and clear the rubbish area” said Steve. Jill smiled. He was obviously embarrassed, thinking he was unpacking her smalls.

“No, Steve, don’t go. These are for you.” she said in what she hoped was a natural voice. Jill took out a white, sleeveless, polo-necked woollen top and a black skirt. Steve stood transfixed, suddenly afraid. “What if it was all a mistake, a fantasy?” he asked.

“There’s only one way to find out, isn’t there Steve?” Jill said, throwing him a pack of designer tights. “Put on your bra and panties, then the tights, then the teddy. Roll the tights up your legs, don’t pull. When you’ve done that, give me a call.”

She turned and left her bedroom. Steve felt nervous, butterflies fluttering in his stomach. He wanted to put on the clothes but was afraid. Yet he also felt a strange excitement as he found himself divesting of his clothes. He could not believe how soft and sensuous the panties and bra felt. He filled the bra cups with tissues. The tights felt erotically electric, seductiveley gentle as he rolled them up his legs and into place. The teddy hid the filling of the bra cup and he felt sensuous, but more than that he felt feminine.

Jill entered the room and smiled, “Suits you,” she said.

All hint of masculinity was now hidden, and with the padded bra, Steve’s shape had become decidedley feminine. She handed him the slip and then helped him into the sleeveless jumper. Then she fastened the skirt around him and tightened the wide black leather belt. He pulled on the white shoes with their three-inch heels.

Next, Jill made him up, showing him how to apply foundation, blusher, eyeshadows, mascara, eyepencils and lipstick. She shaped his broken nails into some sort of feminine style before applying two coats of varnish. Despite Steve’s half-hearted protests, she highlighted and permed his hair into a distinctly feminine style.

It was when she lit a candle and began to heat a needle that Steve became concerned. Jill picked up a cork – “Sit still” she muttered.

She put the cork behind the lobe of one of his ears and pierced it quickly, repeating the performance on his other ear. Steve yelped in pain and surprise, and ignoring his unlady-like curses, she put sleepers into his newly pierced ears.

Finally, she hung a choker necklace around Steve’s neck and a large silver bracelet on each wrist. She took Steve’s hand and led him to the mirror.

“Is this really me?” he asked, his voice taking on a softer tone.

“Yes, it’s you. Steve, I’m going to put myself on the line for you. For one month you’re going to be the girl you think you want to be. But remember, being a girl is fulltime, not just when you feel like it. The only way you will know whether your feelings are real is to live them out.”



She collected the make-up, the handbag and a trendy jacket. “Take these to your room.”

Steve looked out of the window, it was already evening. He gently opened a carrier bag and pulled out a negligee with two pairs of matching knickers and a wrap. There were also two bras and further knickers.

Jill made dinner and waited to hear footsteps on the stairs. She smiled as Steve minced almost daintily into the kitchen and sat at the table.

“There are certain ways ladies sit, Steve, with their legs together or crossed. They also eat slowly, take smaller mouthfuls and chew in a more delicate fashion.”

Steve blushed slightly, and all through the meal he found himself being corrected. After dinner they sat in the lounge, and Jill looked at Steve carefully.

“Okay, these are the rules. I can’t go on calling you Steve, so from now on you’ll be Samantha. Tomorrow we’ll go to town and choose some more clothes. When we return you’ll spend an hour cleaning and doing chores.”

Jill looked at the pouting figure with ‘her’ arms laid delicately in ‘her’ lap and legs tightly crossed. It was hard to visualise that this ‘girl’ could possibly be Steve. “We’ll try some dressmaking and typing, I’m sure you’ll get the hang of it. You are entering a female world. You may be beautiful but there’s more to femininity than sitting pretty, if you decide you love this life you will need a job.”

Steve finally spoke: “Jill, I’m scared…”

Jill touched the hand that lay in Samantha’s lap and squeezed it.

“But isn’t this what you wanted, Samantha? Learn to let your soul take over. Learn to feel and be yourself.”

Samantha?? Well, it wasn’t too bad. He would have to think of himself as that. He would look stupid telling someone his name was Steve dressed like this.

“Thanks, Jill” he said.

Jill smiled. “Go to bed, and sleep well. You have a big day tomorrow.”

Part two >>>

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