He wished his life could be happier, but here, on the road, he felt better. It was like the stories of boys going out to seek their fortune; like Dick Whittington. But he was very, very hungry.

A car pulled along side and the lady inside asked, “Would you like a ride, young man?” Seeing an open bag of cookies John decided to accept the ride. “Hi - I am Mrs. Ann MacDonald. May I ask your name?”

Staring at the bag of cookies, he replied, "Oh, John Summers Ma’am.” Ann noticed John looking intently at the cookies. “Go ahead, take what you want,” handing him a bottle of soft drink from the back seat.

John ate six cookies and drank half bottle of soft drink as if he were starving.

“John, may I ask, when did you eat last? “John told her about the boarding school, and not being allowed to eat because he was one of the smallest boys there and had to do what the older boys wanted, and do as they told him, or not eat. The car stopped and Ann told him to wait in the car - she would be right back. When she returned Ann had a large sandwich and milk, “Here John, enjoy yourself.” She handed him the sandwich and the milk. When the car stopped again it was at the police station.

“John, come with me please.”  The lady at the front desk asked if she could be of help. Ann told her what John told her, and testified to his hunger. Stepping out from behind the desk, the lady police officer sat, and asked John to sit beside her.

“John, my name is Kathy; please tell me your full name and how old you are.” Looking up at her, John answered, ”John Summers, and I am twelve year old.”

After talking with John a few minutes she went to the computer and typed in John’s name. In a matter of seconds the printer started to spill out paper. "Mrs. MacDonald, do you know where John is staying?” John overheard Kathy, and interjected, “I have no place to stay. I will just sleep in the park Ma’ am.”

Kathy said firmly, “No you can’t, we will have to find you a place to live, or stay for the night, John.” Ann hinted to Kathy, ”John could live with me? I have a big house and he would be no bother; as a matter of fact I would love to have him.” The perfect boy for her to make a girly boy out of, or better yet a girl, she thought to herself dreamily. She had always wanted a pretty daughter so badly.

"What a find!" John thought to himself.

Kathy made a phone call. Hanging the phone up, Kathy asked, “John would you like to live with Mrs. MacDonald, as her son for a while?” Nodding his head, he replied, “Yes.”
“Then it is settled. The custody papers for you to sign will be arrive as soon as can be arranged, and that is it.”

At Mrs. MacDonald house John fell asleep on her couch, so Ann let him sleep, turning off the lights and going to bed herself. When Ann got up John was still dead to the world. The last three days had exhausted him. Smiling, she went to the kitchen to fix breakfast for the both of them. She had made the hot chocolate when John woke up.

“Good morning sleepyhead, are you hungry?” Wiping his eyes, John answered sleepily,”Yah…” Sitting at the table, they both ate eggs and toast and hot chocolate and talked and giggled.

“Honey, there is a bathroom right down that hall to your left, why don’t you start your bath while I find you some clean clothes to wear, okay?”

John went and started his bath. Ann wanted to dress him in pretty panties and a dress straight away, but knew better. She thought to herself, not until tomorrow, or at the earliest tonight… John found boys' underpants, jeans and t-shirt, with some clean socks, supplied for him.

Knocking on the bathroom door, Ann called, ”Here are some clean clothes you can put on.” John put his hand out and took the clothes. ”Thank you Mrs. MacDonald.”

pulling the clothes in. It was after lunch when the custody papers came. Ann read them to John, and answered all his questions before she signed the papers. In her mind Ann had it all plannd out, and now she was going to put her plan into action. “Would you like to help me sort out some thing in the spare bedroom today?”

“Sure, I’d love to.” said John.

In the spare bedroom John I take in wayward girls sometimes, so I keep a variety of clothes. One can never tell when one might need them.”

Smiling to herself, she was picturing John dressed in a pretty dress and frilly panties. Intentionally Ann started sorting the girls’ panties handing them to John to pile on the bed. John’s face turned deep red. Pretending to suddenly notice this, Ann said,” Oh! I’m sorry John; I didn’t mean to embarrass you.”
John blushed even more, feeling shy and confused.

“They do feel really nice, don’t they?” John didn’t answer but nodded his head - yes. “Have you ever touched girls’ panties before?”

“No,” answered John shyly, trying hard not to make eye contact with Ann. The rest of the afternoon they worked cleaning the living room, never mentioning anything about panties again. Later she had him help her carry slips and petticoats to her room. “John, come here let me hold this half-slip up against you - just to see what it would look like, please!”

“No! Please don’t do that,” said John, now feeling more embarrassed than ever.

“Ah, pretty please? I don’t want you to wear it; unless that is what you want to do of course.”

John moved to where she was standing and let her hold the half slip up against him. ”Very nice, too bad you are not a girl. Look at all the fun you’re missing.” They ate dinner and walked to the park nearby, and then headed back home.

At home Ann asked John,”Does the word ‘panties’ scare you? Be honest, does it?” John’s face turned crimson red,” W…well kind of. Only because they're for sissy girls,” said John, reddening and looking at the floor. He frowned, wondering where all this was leading.

“Let me see your hands, John.”

“Why?”

“Just let me see your hands, ok?” John held his hands out for Ann to see. “Hmm, they look okay to me. Your fingers didn’t fall off, and your hands didn’t turn green. So it is safe to assume that touching girls’ panties is harmless to the male species of the human race.”

John started laughing. Ann pushed the point harder: “John you really want to wear girls’ panties don’t you?” John shook his head - no.

“John tell me the truth, you want to, but you’re scared.”

John retorted,” I am not scared, I just do not wear panties; I’m a boy!” He sat beside her squirming at her embarrassing interrogation.

“It would be fun and you know it, don’t you, sweetie?”

“Please stop talking about panties. I don’t wear them and won’t wear them.” Ann smiled. Nothing more was said about panties while they ate their supper.

“John, check to see if you have clean underpants would you please?” asked Ann, knowing full well he had no clean underpants to change into.

John came back. “No, I have no clean underpants to wear,” he said with worried feelings tingling his spine.

Ann smiled, “We have a problem; I want you to take a bath tonight but you have no underpants that are clean.”

John knew what she was up to, ”No panties, I’ll take the ones I’m wearing and wash them out by hand and dry them over the heater, I’ve done that at school, then take my bath.” Seeing the look on her face, “What is it with you and panties? Oh well. Do you have any pajamas to wear to bed?” John shook his head, indicating no.

“Then would you wear the pajamas I want you to wear - I’ll be honest, they’re baby dolls. I do not want you running around with no underpants on.” John just stood there, not saying a word. “Sweetie I’ll make you a deal. I will let you go to bed with just your jeans and t-shirt on tonight, but tomorrow when you get up you will take a bath and put on a pair of panties of my choice. Or you can do it now, it’s your choice.”

“Okay let’s do it now and get it over.”

Ann hugged John, “Take your bath and meet me in the spare bedroom. After his bath, John wrapped a towel around himself and met Ann in the spare bedroom. He walked unwillingly towards Ann.

“Honey you will be alright, I promise. Now you just cannot go around in just your panties. That would look funny. She held out a yellow dress with the very same half-slip from that afternoon. Then she produced a pair of pink ruffled panties, holding the waist open.

“Step in, Honey.” John reluctantly stepped into the elaborately trimmed panties, and the feel of the silkiness against his legs as she pulled them up and settled then neatly around his bottom excited every nerve in his body.

“There, not as bad as you thought.” He smiled with embarrassment. Next she ordered him to step into the silky half-slip, adjusting it at the waist. It felt delicious, but John tried to not let it show. Once the dress was in place she put white knee socks on him with yellow Mary Jane shoes. John danced around the bedroom, loving the sensation of the panties with the slip and dress. “I like it, really I do!”

Ann gave him a kiss, “You look like a boy in a dress, but that is okay for tonight, and tomorrow I’ll fix your hair.” They spent the evening watching TV and eating popcorn with butter on it. For bed Ann put a pink nightgown on him with ruffles at the bottom, and with a lace collar and with lace on the sleeves.

In the morning Ann went in to wake John, but to her surprise he was wearing his own clothes again. The panties and slip and dress were in a pile on the bed, along with the nightgown.

“John honey, why are you wearing your jeans and t-shirt, are you wearing your underpants too?” Tears running down his cheeks, John replied, “I decided I don’t want to wear girls’ clothes anymore.” It was all he could do to keep from crying. He felt so confused at all the mixed and conflicting feelings that were running through his mind and body.

“You told me last night before you went to bed that you love wearing those clothes. What changed your mind?”

John could see the anger in Mrs. MacDonald’s eyes. “I am a boy, I talk like a boy. I like boys’ things; really I do."

Standing up, he quickly pulled his underpants and jeans back up. “I want to go back to my father, please. My father and my mom know I’m a boy.

Ann started to move towards him. “No!" he cried. He ran from her making his way to the door. Ann picked the clothes left piled on the bed, “Okay John, you don’t have to wear girls’ clothes any more.”

John’s eyes never left her, “I still want to go to my dad.” Ann could see that John did not trust her, and that she had to do something or she would lose this very special child, never to gain him back.

“Honey," she said sweetly, "would you stay if I promised not to make you wear girls' clothes again?”

John stepped into the hall. “Would you give me three weeks as a trial to prove my trust? Then if I do could I be your mother?”

“I don’t know.” He wanted to get away.
“Okay, if I fail and you cannot trust me, then I will have Kathy take you to your father, okay?” She began putting the last of the clothes away, knowing she could wash them later. Ann knelt down holding out her arms, “I’m sorry Honey.”

John let her hug him. She was nice, and the next three weeks should clear things up, he thought. The next three weeks went by with a lot of good times. John agreed that he would stay and that he trusted her, calling her Mom.

Ann, meanwhile, was rethinking how to feminize this pretty little boy. One afternoon Ann called a professional friend of hers and agreed to meet her that evening while John was sleeping. “Honey tonight I have a business meeting so I would like for you to be in bed a little earlier.” John was tired, and agreed.

An hour later Barb Blake knocked on the door. Anne answered the door: “Thanks for coming over Barb.”

Barb grinned. “No trouble, what seems to be bothering you so much?” Ann told her about John and showed her a picture of him.

” Aw…he is adorable; you’re right he is too pretty to be a boy. Definitely a girl.”  Ann thanked her and continued telling what had happened four weeks earlier.

“Ann, you and John come to my office, and together we will have that pretty child of yours in dresses and pretty panties in no time,” said Barb brightly, her eyes twinkling.

“Thanks, Then John and I will see you tomorrow at three?”

“That is fine, see you both then.”

The rest of the night Ann danced through the house with renewed spirit and hope. Three the next afternoon John and his new mom were in Dr Barbara Blake’s office.

“Hi John, this is John?” Ann nodded - yes. “I am Dr Barbara Blake. I am a doctor of the... soul. I work with the mind, and how people think. John, would you tell me the worst thing that your new mother had you do?”

John looked over at Ann. “It is okay, go ahead and tell her. I will not get angry.”

“She had me dress is girls’ clothes, including girls’ panties.” he explained, staring at the floor bashfully.

“Does that…bother you?”

He shuffled his feet, replying "Ye…s.”

“Why, John?”

Because I’m a boy and boys don’t wear girls’ clothes.”

Barb put her hand on his shoulder. “When you helped Ann sort the panties out and you had to pile them on the bed, did they feel really nice and soft to you?”

Nodding, he said softly “Yes.” Very meekly holding back the tears, John spoke up, ”She asked me if I was afraid of the word ‘panties’.”

“John - are you afraid?”

John looked up at Barb. ”No not of the word… ‘panties’. I just don’t want wear them.”

Ann and Barb could see the red coming into John’s face. Barb held John’s hands. ”John, I want you to do me a favor. Like they do with people who are afraid of spiders, they have them handle them to show those people that they have nothing to be scared of. So I want you, starting today, when you get home with your mommy, for one hour before bedtime, to wear a pair of girls’ panties - the color does not matter.”

John glared at Barb. ” Why? I am a boy, not a girl.”

Barb laughed,” Yes that is right and no-one can take that away from you. That why I want you to wear the panties, to show you that you’re still a boy, still male no matter what you are wearing. I want you to prove it to yourself and then whether Mommy asks you to wear girls' pretty panties, or boys' plain underpants; you will not think any thing of it. Why; because you know you’re still a boy and wearing girls’ clothes does not make you a girl.”

John knew somehow he had been hoodwinked by Dr Blake and his new mother. ”Okay. One hour before bedtime, right?”

Barb confirmed, ”Yes, one hour before your bedtime.”

John said nothing, but the look on his face showed he was terrified by what was to happen an hour before bedtime. The thought of the frilly lacy panties alone mortified him to the point of just about passing out.

”John, a week from today at the same time I want to see you and your mother again.”

Ann’s eye sparkled, “Thank you Dr Blake, and we will see you next week at three. “

Back home, John and Ann were watching television.

“Take your bath John, you have something you have to do before bedtime, don’t you?

John finished his bath, and, wrapping a towel around himself, walked out to the woman who was desperate to be his mother. Lying on her lap was a pair of white satin lace panties with pink bows. Slowly he moved towards Ann as she held them out for him to step into.

“There! At eight o’clock you can take them off. How about some ice cream?“

They ate ice cream and talked. At eight o’clock John removed the panties and put his boys’ pajamas on, and then went to bed.

The next morning Ann asked him,” John what did you think of wearing those panties last night?

”He could feel the blood running to his face. ”They were okay, at least they didn’t hurt me.

”Ann put her arms around him, hugging him and kissing him. “John, you are every bit a young man; and because of what you did last night I’m proud of you.” She kissed him again.

The week passed, and they were back in Barb’s office. “Well John did you do as I asked you to do?”

John nodded his head.

Ann spoke up, ”Doctor, he did very well; he didn’t make one complaint.

”Barb asked John, ”Tell me now how you feel about wearing girls’ panties; and i mean directly and honestly.”

John hemmed and hawed, ”The panties didn’t hurt me any, although I was scared someone would come in and see me wearing them.”

“If you were asked to wear girls’ panties for a week or maybe a month or better, how does that make you feel?”

Looking at Ann, John answered, “I wouldn’t like it, but if I had to I could, it’s not that bad.”

Barb grinned, “Felt kind of nice didn’t they, the only real fear was that someone else like, another boy, might see you; that is the real fear you have, isn’t it?”

Looking at the floor, John  answered, ”I guess so.”

“You guess so? You mean you know so for sure. Am I right?”

John was forced to look her in the eyes. ”Yes… you’re right,” he answered, feeling as though he might cry.

Barb pulled a pair of pink rhumba panties out of her coat pocket. ”Put these on right here in front of your mom and me, now. ”John did as he was told without crying.

“Very good; you can put your jeans back on now over them. You are wearing the panties home. And,
along with them, you will also be wearing skirts and dresses. Not for just an hour before your bedtime either, but for the whole day.“

John asked, ”Why? To prove to myself that I am still a boy, no matter what I am wearing?”

Barb smiled. ”Now, that is what I like to hear! I will see you both in six months, and John, you are to do what I told you. That means away from home as well as at home; in other words all the time until I tell you otherwise.”

Looking closely at Ann, Barb said, ” If you let him off, I promise you will lose him. I’ll see to that.” She winked at Ann.

During the ride home John asked, “Does this mean I get to go to my father now? You did promise that you would not make me wear girls’ clothes.

Ann parked the car. ”I am not the one making you wear girls’ clothes, Dr Blake is - read the papers
yourself. In fact I can prove it.”
The car came to a stop, “Come with me John.”

Getting out of the car, John realized it was the police station. ” Why are we here?”

“To show Kathy those papers, and let her tell you who is forcing you to wear girls’ clothes.”

Inside Kathy read over the papers. “John, your new mother has no choice - either you wear what the doctor says, or I’ll have to put you in some place where they will make you do as the doctor says.”

John said nothing all the way home. Inside, Ann hugged him and led him to the spare bedroom.

“Now John, take off your clothes except your panties. She pulled a very full and richly belaced slip over his head and into place, and then a bright yellow dress buttoning firmly up the back. There followed white knee socks and yellow Mary Jane shoes, and John felt the pretty girls’ clothes weakening all resistance in him.

The months passed, and by the end John would have nothing to do with boys’ clothes, and had changed his name to Jocelyn MacDonald. Ann finally gained a daughter who loved her, and whom she could love back.
Dennis