Thanks Maddy for your story. It gave me the push to get this short story done. ~Samantha
 
 
 
A year ago I was a down and out. So down and so out that I was on the verge of committing suicide. I was rescued by a girl called Angel who made me promise to help someone in need like she was going to help me.
She took me home to her place after she had finished her duties at the shelter and told me she was going to get some sleep and to wake her around three.
Whilst Angel slept I decided to have a long soak in the bath, something I hadn’t done in a long while, and to see how much cleaning I could do without making too much noise.
At three I went into her room, placed a cup of coffee on the bedside table and gently awoke her. She looked at me, I was wearing a towelling robe, then at the coffee.
“Why thank you, kind sir.”
“It’s the least I can do. I hope you don’t mind me borrowing your bath robe, but I didn’t want to get your nice clean home dirty.”
“It looks good on you. Pink suits you.”
I left her alone to get dressed and began to get her breakfast ready. I had checked the cupboards and made an educated guess at what she might eat.
She entered the kitchen ten minutes later wearing just knickers and a bra. She looked at my offering and said, “You are such a dear, just a little milk on the bran flakes and no sugar. I need to watch my figure.”
“And it’s a lovely figure.”
“Thank you again, kind sir.”
She took the offered bowl of cereal and sat opposite me at the breakfast bar. I refilled the kettle and prepared to make another cup of coffee.
“There’s a spare bedroom and I want you to make use of it. I’ll help you get a job and I can begin to help get your life back together.”
“Thank you, I don’t deserve this you know. There must be people worse off than me?”
“There probably are, but you are the one I have picked to repay my debt. Now one of the first things we have to do is to get you some clothes, both male and female.”
“Male and female?”
“Yes, you said you are a transvestite and I want you to be able to wear our clothes as well as yours. I need to do some research as I know very little about people like you.”
“People like me are just like anyone else with the exception that we sometimes like to dress in clothes of the opposite gender. Whereas you get away with it, I am ridiculed.”
“What do you mean I get away with it. I don’t wear men’s clothes,” Angel sounded puzzled.
“You wear jeans don’t you?”
“Yes.”
“Trousers were once a male only item of clothing.”
Angel thought for a moment and then said, “Ah I see what you mean, jeans, slacks and shirts are so much part of a female’s wardrobe that we forget that it wasn’t all that long ago that they were classed a male only clothing. I see that I have a lot to learn.”
“I will help on that score.”
After she’d finished her breakfast I started to cleanup and she went and switched on her laptop. She browsed for a couple of hours whilst I finished cleaning the house.
“Do you know your sizes?” she asked.
“I take a six in shoes, fifteen inch collars and twenty four inch short trousers.”
“Bra size?”
“Thirty Two.”
“Perfect,” and she went back to her bedroom.
“You are just a bit bigger than me,” and she handed me a pair of pink knickers and a matching bra.
“Have you got some sticking plaster strip?”
“Why?”
“I’d like to tuck to wear these.”
“Tuck?”
“The art of pushing my balls back into my body and securing my penis out of the way.”
“Ouch,” she said and went to fetch the plaster.
Ten minutes later I was wearing the bra and knickers and was getting the once over from Angel.

During the year I discovered that Angel owned a dress shop, she had inherited the shop and money from her parents, and I began to work there. I was dressing in female attire during work hours and Angel found that more and more men were shopping with us. She bought the shop next door for me to run and set it up especially for cross dressers. We went from strength to strength and I found a whole new niche in life. I was forever thankful to Angel and we became very close.
That very brief account brings us upto date. As yet I haven’t found someone to repay my debt.

It was whilst I was opening up the shop that I saw her. She couldn’t have been more than twelve and I was surprised that she wasn’t at school. I watched her as she checked out her surroundings and disappeared down an alley. During the morning I kept an eye on the alley and didn’t see her come out.
At lunch I took a look down the alley and found nothing unusual about it. It was just a normal loading area, a couple of dumpsters and nothing else. I wondered where the girl could have gone and then noticed that one of the properties was derelict. I went back to the store and decided to keep an eye out for my mystery girl.
I didn’t see her that day, but I saw her again the next morning disappearing down the same alley.
“Angel, did you see that girl?”
“What girl?”
“Dark haired, about twelve years old and looks like she lives somewhere in that alley opposite.”
“Sorry love, I didn’t,” she answered.
“Can we get here a little earlier tomorrow?”
“Of course, ten minutes be enough?”
“More than enough. Thanks, you are such a dear.”
Again, I kept the alley under watch and didn’t see her reappear. We had to get some shopping that night and I got a couple of things for the girl.
The next day I hid behind the dumpsters and watched the alley entrance. It wasn’t long before I saw her coming down the alley.
I stepped out and holding out the chocolate bars said, “I thought you might like these.”
She looked scared. Very scared.
“I’m just offering you some chocolate, no strings. I’m Stella, I work in the store across the road and I thought you’d like some chocolate.”
She looked at the bars, then at me and then at the bars. She came close, grabbed the bars and backed off.
“Enjoy them, I’ll bring some more tomorrow.”
I left the alley without looking back. I was hoping to gain her trust and I didn’t want to frighten her anymore than I had.
I was in the alley the next morning with a couple of bars of chocolate. I hoped that she would return and as time went on I started to get worried. She came into alley and I noticed that she seemed to be looking for me.
“Morning sweetie, did you enjoy the chocolate? Here’s some more. If you want anything just let me know and I’ll get it for you.”
I offered the bars and she accepted them and I left her. She didn’t look as scared as yesterday. I hoped that she would begin to accept and trust me. I knew that it could take some time.
That night I spoke with Angel.
“Sweetheart, I think I’ve found the person I’d like to help. She’s the girl from the alley and I really think that she could do with some help. I think she’s living rough in one of the derelict shops opposite us. Because she’s young I believe she sleeps during the day and looks for food at night.”
“You recognise the signs?” Angel asked.
“Yes.”
“But why sleep during the day? I would have thought it was more dangerous at night.”
“If she’s as young as she looks then she should be at school and there would be more people around to ask her why she isn’t. If she’s running from someone or something, then she wouldn’t want to run the risk of being asked awkward questions.”
“Ah, of course. Any kid of school age walking the streets during the day is likely to be noticed, but she could get away with it at night and at weekends.”
“Yes and that really worries me as she is more at risk at night.”
“If you need any help just let me know.”
“Looking ahead, would it be okay to bring her here, I haven’t got anywhere else to take her?”
“Of course. She can use the spare room now that you are sharing mine.”
“I wanted to talk to you about that. Angel, you are the best thing that has ever happened to me. I am grateful for everything you have done for me and I would like to know if there is any hope of us getting married?”
“Is that a proposal?” Angel asked.
“I suppose it is. I’m just so worried about being rejected.”
“You silly girl, I would never reject you. And yes there is every hope of us getting married.”
We both began to cry as we hugged each other to death.
I was in the alley the next morning waiting for the girl to turn up. When she finally turned up I thought I saw a glimmer of hope in her eyes. She accepted the chocolate and I said, “Tomorrow’s Sunday, so I won’t see you till Monday. Are you going to be okay?”
She nodded and I left.
I worried all Sunday. I couldn’t settle. Angel kept me going as best she could and on Monday I was thinking all manner of nasty things.
When I saw her she appeared to be okay and I sighed a big sigh of relief. She noticed this and asked, “Why the sigh?”
“I was so worried that something had happened to you.” I handed her the chocolate, “Same time tomorrow?”
She nodded.
The rest of that week was like the previous week. Then on Saturday morning she wasn’t there. I began to come unglued with worry. Angel calmed me down and I went about my job mechanically. I was in the stock room when I heard Sandy, my assistant, shout for me. I dashed back into the shop to see Sandy holding a girl, my girl.
“Into the staff room,” I said.
“Sandy, will you be okay out front for a little while?”
“No problems, Stella. If you need anything, holler.”
“Thanks,” I looked at the girl and said, “You okay?”
“Yes,” she replied.
“What happened?”
“I got beat up, it happens, but this time it was the worst I can remember.”
I looked at the bruises, the swelling around the eye and the torn clothing and asked, “Are you sure you are okay?”
Before she could answer Angel came in and gasped.
“Angel, call Greta and find out when we can see her privately.”
Greta was our doctor and had become a close friend of Angel’s. She was the one Angel’s benefactor had taken her to to get her drug free and she was the one Angel had taken me to to make sure that I was okay. I could trust Greta.
Angel went to make the call and I turned my attention back to my girl.
“What’s your name, I can’t keep calling you ‘my girl’?”
“Jo,” she answered.
“Well Jo, welcome to my store. Sandy is my shop assistant and Angel is my partner, both in business and in life.”
“Who’s Greta?”
“Greta is our doctor. I’m going to get you checked over and see if we have to take you to hospital. Don’t worry, she won’t say anything to anyone, but if you need to go to hospital then we will go, there will be no argument over that. I will make sure that no one asks any awkward questions.”
“I don’t want to go to hospital and I don’t need Greta to check me over.”
Jo began to get up, winced and collapsed back onto the chair.
“Jo, don’t worry. You are coming home with Angel and me, once you’ve recovered you can decide whether you stay or whether you want to leave.”
Angel returned and said, “Greta will meet us at home, I’ve promised her a meal, so you’d better make sure it’s a good one.”
“I suppose you want me to dress up as the maid?” I asked with a smile.
“You haven’t been one of those for a while so yes, and not to be left out, I’ll dress as a nurse.”
“You just want your wicked way with me,” I said.
“And you don’t?” Angel got in.
“Yes, but we will have guests and one will be staying with us for a time.”
Angel looked at Jo and said before leaving, “I’ll get some clothes to take home with us.”
Jo wasn’t left alone for the rest of the day. At home time I gave her a coat and Angel put some bags in the boot of our car.
At home, I changed into Marie, the French maid, while Angel watched Jo.
“Bonsoir Madame, mademoiselle. My name is Marie and I am your maid for this evening,” I said when I entered the living room. I was wearing a traditional French Maids uniform with a white cap pinned to my wig. I had a small white apron protecting my skirt, seamed stockings and four inch heels.
“You look delightful, Marie, now if you excuse me I’d like to change also.”
It took Angel ten minutes to change and all the time Jo never took her eyes of me. Angel entrance was dramatic. She was wearing a low cut and very short nurses uniform, white stockings (you could see the tops and garters) and black four inch heels. She had put on a long, waist length, blonde wig topped with a nurse’s cap.
“Where’s my patient?” she asked.
She sat down next to Jo and said, “Now don’t worry, Nurse Bennett is here to look after you.”
“I’ll start dinner Nurse Bennett,” I said.
“You do that Marie and I’ll look after the patient.”
I started to prepare the meal. I decided on a simple dish as I didn’t think Jo’s stomach would be able to handle a large meal. Spag Bog was a simple meal and Jo could eat as little or as much as she could eat. I had plenty of pasta for the spaghetti and I could use one of the propriety bolognaise sauces with the mince.
The door bell rang and I went to open it.
“Bonsoir Monsieur Adams, Madame Adams. I am Marie. Nurse Bennett is expecting you,” I said as I took their coats.
“Nurse Bennett?” Greta asked.
“If you would follow me please.”
I opened the living room door and said, “Monsieur et Madame Adams, Nurse Bennett.”
I stepped aside and allowed them to enter.
“Oh my. I’m glad my nurses don’t dress like that otherwise I wouldn’t be able to keep Tom out of my surgery.”
“Nurse Bennett, you look ravishing,” Tom said.
“Watch it Tom, or I’ll let Marie dress you,” Greta said with a smile.
“Doctor Adams, you can examine my patient upstairs,” and Angel helped Jo to our bedroom.
Tom followed me to the kitchen and asked, “Peter..”
“Marie,” I corrected.
“Marie, sorry, how do you do it?”
“Do what?”
“Look so convincing.”
“Lots of padding and painful tucking and thank you for the compliment.”
“You’re welcome and you make a very beautiful woman.”
“Makeup covers a multitude of sins.”
With Tom’s help I had the meal ready and got Tom to join the others at the table, Angel had told me they had finished the exam.
I served the spag bog and was just about to leave when Angel said, “Marie, won’t you join us. I insist.”
“As you wish Nurse Bennett.”
Over the meal Greta said that the injuries Jo had were not serious and would heal and that Jo wouldn’t any medication. I thanked Greta and the relief showed on my face.
Tom and Greta stayed for a couple of hours after the meal and I gave both of them a kiss on the cheek as they left. I went back into the living room where the sexy nurse grabbed me and gave me a very passionate kiss on the lips.
“Peter, please sit down,” Angel said.
I noticed Jo’s eyes get very wide.
“Jo, I think you have just realised that the beautiful woman that has befriended you and who is currently dressed as a maid is actually my male boyfriend and, I hope, my future husband. Let him tell you something and you can then can decide whether you want to respond.”
Angel sat back and waited for me to begin.
“Jo, about a year ago I was a living in a bed and breakfast hovel paid for by Social Services. I was at my wits end and had decided to commit suicide. I was in a shelter run by a charity over Christmas where I met Angel. She decided to help me as she had been helped, but she made me a promise that I would help someone in the future to repay my debt to her, just as she was repaying her debt to her saviour.”
I paused and then continued, “I know you are living rough, although I don’t know why and I would like to help you get your life in order. I know that you are too young to make a promise to help someone in need…”
“I’m eighteen,” Jo interrupted.
“Sorry?”
“I’m eighteen and I promise to help someone in need in the future, just like you are going to help me.”
“But I thought you were a twelve year old girl.”
“I’m sorry to disappoint you, but I’m an eighteen year old boy, as Angel and Greta found out earlier.”
“Jo, will you accept my apology in mistaking you for something you are not.”
“It’s not your fault, Peter is it?”
“My given name is Peter, I work with Angel in her dress shop…”
“Your dress shop love,” Angel interrupted.
“Thank you dearest. My dress shop. I cater mainly for men who dress as women where I go by Stella. As you’ve seen tonight we also like dressing up as other people and use whatever name seems appropriate.”
“Well with long hair and my short stature, people often assume I am something I am not. I have gotten use to being mistaken as a girl so it doesn’t bother me anymore.”
“Jo, would you like to see what you’d look like as an eighteen year old girl?” I asked.
“But I’m only just five foot.”
“Which is just under the average height for a teenage girl,” I said.
“I’m game. I’ve been mistaken for a girl for so long, it would be interesting to see what I’d look like.”
“Angel, would you do Jo’s makeup and you are much better at it than me?”
“Of course.”
“Jo, take a shower and wash your hair, there’s some conditioner on the shelf. Put on a bathrobe and join me in Angel and my bedroom.”
Jo went to the bathroom whilst I went into the bedroom to look for the things I would need.
When Jo entered I had him sit on the edge of the bed.
“This is called a gaff,” I was holding up a pink pair of elastic knickers, “you use this to keep things under control and give you a flat front. You push your testicles back into your body and your penis between your legs. The gaff then holds everything in place.”
Jo, with my help, got the gaff in place.
“These are knickers which are nicer to wear than male pants. Well I think so,” and I handed Jo the knickers and a bra.
“When you’ve done it a few times fastening a bra behind you back becomes second nature, or you can fasten it in front of you and pull it round. But I will fasten it for you.”
I then gave Jo a silicone breast to hold.
“These are breast forms. They can be attached to the body with medical adhesive, like I do during the week, or can be placed in the bra cups. I sometimes do this if I am only going to dress for a short time.”
I put the forms into his cups and showed him how to position them.
“We now have a choice between tights, knee highs or stockings. Tights are worn with very short skirts unless, like Angel did, you are dressing for effect. Knee highs are worn with slacks if you don’t want to wear tights or stockings and stockings are worn with skirts, dresses or slacks. There are two types of stockings, hold ups or the type that need garters to hold them up,” I handed Jo some tights.
“They way you put them on is to gather the leg up into a ball and slip your foot into it. Then you pull the material up your leg releasing it as you go.”
Jo understood what I meant and soon had the tights on.
“Teenager girls often dress to attract men. Now I’m not saying you have to attract a man, but to fit in with being a teenager you will have to dress appropriately.”
I gave Jo a tight t-shirt to show off his breasts and a mini skirt to show off his legs.
“Heels really show off the legs. I would wear three inch heels with that skirt and I think these might fit.”
Jo slipped his feet into the shoes, “They’re a good fit and they are not too high for me.”
“Now let me let Angel loose on you.”
Angel, who was sitting quietly on the other side of the bed took over.
“If you have no objection, I will fit false nails to your fingers and make up your face. Then we will let you look at yourself in the mirror.”
Angel worked for fifteen minutes before she declared herself satisfied. Jo stood up and Angel opened a wardrobe door to reveal a full length mirror. Jo looked at himself, turning first one way and then the other. He walked up to the mirror and inspected his face.
“I look..”
“You look terrific,” I said.
“Thank you Angel,” Jo said.
“Angel, do you think Josephine could work with me in the shop?”
“I think that would be wonderful. Sandy could train her and that would release Sandy to work with either of us.”
“Josephine, how about it?”
“About what?
“Living here and working with us. Just until you get back onto your feet and then you can find your own place and job. And when you are ready, you can tell us why you are in the position you were in,” I said.
“You would be Josephine during the day and Joseph at night, or be Josephine all the time. It’s upto you,” Angel added.
“I ran away because I was bullied at school and beaten at home. I have been homeless for two years. I thought that I would never live a normal life and now you have given me an opportunity to begin again. I never ever thought about this, but I like it. I really do, but what about girls?”
“Oh there’s a lot of girls who would just love you the way you are. You, like Peter, are the best of both worlds. A girlfriend to talk to and go shopping with and a boyfriend who knows how to pleasure a woman and not just to pleasure himself. I am grateful for finding Peter,” Angel said.
“And you could be one of Angel’s bridesmaids when we get married.”
“I accept your proposal dearest. You can’t get out of it now, I’ve got a witness,” Angel said as Josephine laughed.