Crossdressing with my Girlfriend and Boyfriend -4- 'Is it Wrong for me to Enjoy it?'

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Crossdressing with my Girlfriend and Boyfriend -4-
‘Is it wrong for me to enjoy it?’

By Cindybelle

Part 4

Janette brings Tim closer to understanding why his mom behaves so weirdly and has some news about his dad, but the embarrassing preparations for his upcoming female lead role in the musical are becoming more intense and then his mother springs an even worse surprise, maybe Aubrey can help Tim though his self doubts.

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Ending of Part 3…..

Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn’t understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave.

I sat with my own thoughts for a while and then I noticed we were not driving home.

“Where are we heading Janette?” I asked.

“Somewhere very special Tim, the place where I last saw your Dad” she replied.

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Part 4

We drove in silence until we reached a local beauty spot, Trensham Ponds, a series of small lakes in a woodland park. Leaving the car, Janette led me to one of the lakes and to a seat in an overlook. It was a beautiful place, peaceful and secluded.

“Tim, your dad brought me here seven years ago just before he left for America, he said he wanted me to understand why he was leaving, I was 15 then and he felt I should know,” Janette explained.

Mom had always led me to believe that my dad had taken off with his secretary and left us. However Janette explained that he and my mom had been estranged for years before this. Mom would have terrible mood swings and berate dad for a whole series of things, big and small, some real but most imaginary. He tried to cope with it, even tried to arrange medical help.

Mom used to call his office and leave angry messages with his secretary, which is how she got to know of his problems, She was a divorcee, and gave him help and sympathy and over time this developed into a relationship. Eventually, he was offered promotion and a transfer to the New York office. Mom said she would not go with him. About this time mom found out about his relationship with his secretary, Brenda, there was an almighty bust up which led to the separation.

“But why has he never seen us or contacted us since he left? Doesn’t he care about us anymore?” I asked. This was the big question that I could never get out of my mind.

“Mom insisted on it,” Janette explained, “Brenda had two teenage sons, if he took off with her, mom made it a condition of not contesting the divorce that she got the house and everything in it, and that he paid for our education through college, but he had no rights of access. He was not to be allowed even to contact us. That’s why our birthday and Christmas gifts come from his office.”

“So I’ll never see him, ever?” I said sadly.

“Tim, I last met your dad, here, 6 months ago!” Said Janette. “It was here, because this is where I said goodbye to him,seven years ago.”

“What! Here? How? I thought he wasn’t to contact us.” I exclaimed.

“That was until we were 21. A few days after my twenty first birthday I got a call at college from your Dad, he said he was coming over to England on a business trip and could we meet? He had traced me from my school office and they told him which university I was at.” explained Janette.

“What was he like? What did he say?” I asked eagerly.

“Tim, do you remember your Dad at all?” Janette asked in return.

“I can remember going to the park and playing on the swings and when he used to throw me up in the air and catch me. I also have this.” I said, reaching into my wallet and bringing out the small dog eared photo of him holding me when I was about four.

“How did you get this?” Janette asked, “Mom destroyed all the photos of him.”

“I found it at the back of a drawer in the desk about three years ago. I never told anyone else.” I said.

“Tim, he is very like you, even to the fair hair, he is kind, considerate and obviously very clever, he is a Vice President of the company now, and he was full of questions about you. He wanted to know everything about you, what you looked like, your hobbies, sports, your school activities. He begged me for a photograph, the only one he had of you was taken when you were four, it may even have been this same one.” She said, holding out my little photo.

“I look at it every day,” I said quietly, looking over at Janette.

“Oh heavens! That is exactly what your dad said,” exclaimed Janette in a strained voice.

I grabbed hold of Janette’s arm and said, “I must meet him Janette, I want to see him, I want to speak to my dad. My life is so messed up and confused right now and mom is only making things worse and she won’t listen to me when I try to tell her.”

“Tim, you will have to be careful, mom has sole custody, she could make it awkward for you and dad if there was contact without her permission. What do you mean about mom making things worse?”

I explained to Janette about the modelling work and being paraded in front of Mrs Pugh and her daughter and about the see through underwear I had to wear for the bridal scene in the Mikado.

“On my, this is getting worse than I realised.” said Janette, “It started with that ridiculous outfit for the wedding. I’ve just had a big argument with your mom about the wedding pictures. Mike and I decided it was unfair to have the photos of you in that outfit circulated, so we deleted, edited, or cropped them and in our thank you letters to our guests we’ve asked them to destroy any pictures of you they may have.”

“Wow, thanks Janette, but what did mom say?” I asked.

“She really lost it and accused me of making her look ridiculous in front of everyone, I told her she should have thought about that before she and Cathy dreamed up the idea and embarrassing you.” said Janette.

“ Cathy has apologised to me about that and has been much nicer to me recently,” I said.

“Well be careful Tim, just like you take after your dad, Cathy takes after mom. Now what can we do about the Mikado bridal underwear she wants you to wear? You said mom bought that at a bridal shop?”

“Yes, a place called Amelia’s in Bramfield,” I replied.

“Oh, I need to tell your dad about that, it could be important. But what can we do now about those Mikado clothes?” she said.

“I think I might know how to get round that” I said, explaining about the outfit that Miriam Jenkins wore at the Opera, my singing there for her, and that I thought that she and I could explain to Mrs Cartwright my drama teacher that a simpler outfit would be more suitable.

“You continue to surprise me Tim, you sang at the Coliseum and now you have Miriam Jenkins coming out to your school to see you! That’s amazing. Well, let’s see if that works. But we need to have a plan to help you if mom gets worse.” Said Janette.

“Here’s what we should do,” she continued, “Although dad can’t contact you, there is nothing to stop you writing to him, I’ll give you his address and then, if and when you want to, you can tell him about yourself and your problems. If he wants to reply he can send it via me and I’ll make sure it gets to you without mom knowing. She mustn’t know anything about this Tim.”

“And now I am also going to give you some money which you must keep hidden. You must promise me that if things get too tough you will use it to come and join me and Mike in Bristol.”

With that Janette handed me  £100 and wrote out my dad’s address and her new address. It was the most money I had had in my life. I looked at the address, - John Bramlett in a place called Manhasset in Long Island, I felt closer to my dad just looking at it. I folded it and put it in my wallet next to my photo of him.

“Tim, I need to start back for Bristol now, I’ll drop you off near home.” She turned to me and held out her arms, “Are you too big a boy to give your sister a hug?”

In answer, I put my arms around her and huddled in close to her. “I really can’t thank you enough, Janette. I was getting desperate, I have so many problems, but with the news about my dad they don’t seem so important anymore. I must meet him though.”

“Don’t worry Tim, after what I’ve learned about you today I will make sure you meet him.” Said Janette.

With that we walked back to the car. Later, when she dropped me off, I said my goodbyes to Janette and then I walked back home deep in thought. I was already composing the letter to my father.

“Where have you been?” shouted mom as I walked in , “ You’re normally back from that old folks home ages before this. If you are going to take this long I will have to stop you going there, I don’t know why you bother anyway, they are just a load of old has beens. Well, while you’ve been doing that I’ve been working all day and I need your help, so upstairs and get into your dress modelling underwear I need to finish off your dresses tonight.”

I went resignedly upstairs. Now was not the time to pick an argument I reasoned. I now had the chance of meeting my dad, this had become the most important thing in my life. So I felt strangely detached as I removed all my clothes and slowly put on the panties and bra and rolled up my tights, I was getting quite used to this now I thought as I put on the slip.

When I had finished I walked over and looked at myself in front of the full length mirror, for some reason I thought of Jason seeing me like this. With the excitement over the news about my dad I had not discussed my involvement with Jason with Janette as I had intended. Then again I wondered if I ever should or ever could talk with her about that kind of thing.

Of course there was talk about boy to boy relationships at school, but that’s all it was, young boys talking. Just like they talked about girls, at first with some disdain, then in time with rising curiosity and then with a growing interest. I imagined Jason approaching me and holding me as he had at Bramfield station and moving to kiss me. Somehow this thought aroused me and on an impulse, or was it an instinct, I walked over to the wardrobe and took out Aubrey’s handbag, the one I brought with me on the train after the swim meet, and pulled out the lipstick and slowly moved it over my lips. Looking at myself I became more aroused and pulled out the mascara and blusher and I somewhat inexpertly applied them. Remembering how Jason reacted when he saw me in Aubrey’s dress at the wedding I wondered what he would do if he saw me now, maybe he would…. And then the phone rang.

My mom shouted up the stairs “It’s for you, its Aubrey, use the extension up in my bedroom and hurry up,”

I shouted OK, and waited until she had gone back into the lounge and dashed across to her room and picked up the phone.

“Tim, Jason’s just told me about what happened at the Coliseum, you really met Miriam Jenkins and you sang on the stage?” she said excitedly, “Why didn’t you call me to tell me about it.”

Suddenly I felt awful, dressed and made up as I was and talking with Aubrey, it seemed wrong and I was ashamed. I stuttered out a reply.

“Oh, sorry Aubrey, I really meant to, after I got back from London mom had me dress modelling again and I was just too tired after that, today I’ve been on the go all the time, swimming all morning , then on to the Old folks home and I’ve just got back in after saying goodbye to Janette.”

“Are you all right Tim, you sound short of breath?” she replied.

“Yes, I’m fine. Its just been a bit of a tiring time I guess, the opera and saying goodbye to Janette were sort of emotional moments as well.” now rushing, I said “Look Aubrey, mom wants me downstairs now, I must go. I really want to talk to you, please say you’ll come next Saturday, there is so much I need to tell you.”

“Hey, calm down Tim, of course I’m coming, don’t worry. What am I saying, you’ve got me worried now. Are you sure you’re all right?” she said.

Then mom walked in and saw me sitting on her bed and had obviously noticed I was wearing makeup. She signalled to me to get off the phone. I said a quick goodbye to Aubrey, trying at the same time to think of an explanation for my mom.

“Well, don’t you look pretty, did you want to look nice if Teresa and her mother come round?” she said looking closely at me.

“No mom, I guess I felt that as you want me to model girl clothes all the time I might as well look like a girl.” I replied, it didn’t sound convincing to me nor by her look did it to mom.

“If that’s what you want, then lets do it every time. I’ll get you a full make up kit and you can learn how to do a proper job. Well, its good that you’ve done this as I bought your wig today for the Mikado and I’ve finished the wedding dress so let’s go and try them on first,” mom ordered.” Don’t forget your white bridal shoes.”

I retrieved the shoes and came slowly downstairs. Mom placed a wig cap on my hair and then arranged a long black wig on my head and proceeded to style it, Japanese style, in a series of elaborate curls and buns held in place by large stick like pins. It felt heavy on my head.

“Now for the dress, be very careful as you step into it, I will only be able to do up the back velcro straps part of the way because you are not wearing the corset which brings your figure in a shade more. But it will do for now.” she said.

It really is difficult getting into a dress with layers of inbuilt petticoat swaying around and oh my, I thought, I’ve got to do all this on stage in Act 2. I felt mom tighten up the back fastening and realised once I’m in this dress there is no way I could get out of it without someone else’s help, I was trapped in it.

“There, how does that feel?” asked mom as she finished.

I walked over to the mirror. The dress was made of what I later learned was white taffeta overlain with silk organza lace frills in a series of scooped layers round the very full skirt, it was shaped around the bust and had what are called three quarter length sleeves in the silk organza, which looked transparent. Now I had the wig on and was wearing makeup the effect was shattering, there was no sign of Tim left.

“Mom, I don’t think I can do this. The dress is heavy, it’s uncomfortable and I would have to wear it for over an hour, most of the time on stage while I’m trying to sing and act, its too much. For the Dorothy part it was just a simple dress, I still wore my own underwear as well.” I was about to go on, but mom interrupted.

“Is that the thanks I get!” shouted mom. “Don’t forget you were specially chosen for the role and I have spent about 15 hours making the dress so you would look the part and all you can say is it is uncomfortable and heavy.”

She went on, “You saw the Mikado on Saturday, didn’t seeing the opera played like that inspire you want to try and do your best for your school? What was it like, what did you see?”

Then I remembered although I had wanted to tell her when I got home, she had accused me of being late and wanted me to model for her as soon as I got in. So I told her about the opera and meeting Miriam and singing for her.

“You mean that you sang on the Coliseum stage and Miriam Jenkins is coming to your school to help and to see the show, and you don’t want to do the role! Oh no Tim, she is going to see you and she is going to see my dressmaking as well you can be sure of that. This is so exciting! I must have Mrs Pugh come round to see you and you can tell her about it.” so saying mom headed for the phone.

“Mom, no, no, please. I’ve had enough for today. I was up early and did 3 hours swimming then I went round to Sunhill until 5 o’clock and then” I nearly said I met Janette, but stopped myself in time, “ and then I want for a walk until I came back home now. I’m really tired.”

“I suppose it is a school day tomorrow and you have rehearsals afterwards don’t you? When do the dress rehearsals start? Asked mom.

“I don’t know mom I’ll ask Mrs Cartwright tomorrow” I replied.

“All right then, let me take the dress off you and remove the wig, then you can get ready for bed, we can show you off to Mrs Pugh and her daughter later this week” she threatened.

When she had taken them off she handed me the dress and the wig and told me to take them up to Janette’s old bedroom as I would be moving into there during the week.

I trudged upstairs and walked into Janette’s room. It still smelt of her perfume and scent. I looked at the pink and white décor and the frilly curtains and bedspreads and groaned. I caught sight of myself in her mirror and with a jolt I noticed that with the clothes and makeup I was wearing I almost looked like Janette.

I ran into the bathroom, almost tore off the underwear and showered for nearly twenty minutes trying to wash the make up off and become Tim again.

Then I went back to my room, I put the little photo from my wallet on the desk and started to write a letter. A letter to my dad.

The next morning I hid the money Janette had given me and the letter I had started to write to my Dad. There was so much I wanted to say and wanted to ask that I was finding it very difficult to write, especially has I never spoken properly with him.

At school I found it difficult to concentrate and was revived when school lessons finished and I went along to the rehearsal room for the cast of the Mikado. I was there first and greeted Mrs Cartwright.

“I’ve now seen the Mikado onstage. I went to the London Coliseum last Saturday, Mrs Cartwright, it was brilliant! I even had a chance to sing on the stage myself.” I had been bursting to tell her this.

“Tim, what on earth are you talking about? How could that happen?” she exclaimed.

I told her the whole story and when I mentioned that Miriam Jenkins was planning to get in touch and help and wanted to see the show she got really excited. By this time the other members of the cast were arriving, so I had to go through the story again.

I suppose it’s fair to say that a number of the boys who had been pressed into playing roles, especially the female roles, had been less than enthusiastic, but the thought of having a real opera star come to rehearsals really stirred everyone up. So things went really well after this and at the end of the evening they were all asking me questions about the London production and the Opera House.

I hung around until everyone had gone so I could get a chance to talk to Mrs Cartwright alone.

“Could I talk with you about the costumes for the show Mrs Cartwright? Having seen the Coliseum production I wanted your views on what my mom is planning for our production.”

“Of course Tim, is there a problem?” she asked.

I explained about the transparent peignoir and corset garment that mom had bought at Amelia’s and the more sedate costumes the Miriam wore at the Coliseum.

“You mean your mother had these garments especially made? Mrs Cartwright queried.

“Yes, she said you had a grant to cover the purchase and could use the garments again,” I explained.

“Oh, the money I have is to cover the purchase of material only , the idea is your mom and the other moms help make up the costumes, we don’t have that much money we can afford to buy made to measure garments like you describe Tim. Plus they are unlikely to fit anyone else.” Mrs Cartwright said. “Don’t worry Tim, I will speak with your mother and sort things out. I agree that the kind of outfit you describe would hardly be appropriate for a school production”

Much relieved, I said “Thanks, Mrs Cartwright. It really has been worrying me. Having sung for Miriam I am feeling more confident now that I can do the role but I do not want to have the extra worry about the costume”

I felt better after that and on getting home found mom did not need me that night for dress modelling, so I went up to my room, finished some homework and resumed composing the letter to my dad.

On Thursday when I got home from school I received a shock. On going up to my room I found it was now full of mom’s dressmaking equipment, even the bed had gone. Fearing the worst I went along to Janette’s old bedroom and sure enough all my kit, my swimming trophies and toys and clothes had been moved in there. I looked in the wardrobes and saw my few clothes and all the dresses and underwear had also been moved as had Cathy’s clothes from her old wardrobe.

I looked around the room. The walls were painted pink with white outlining, there were white lace curtains and the bed had shiny pink satin sheets with lace lined pillows, there were pictures of fairies and ballerinas on the walls, but no shelves to put my trophies or room to hang my posters. This was to be my room.

Mom came in at this point. “Ah I see you’ve come into your new room, as you see it’s much bigger than your old room and I know I can trust you to keep it nice and tidy,” she said.

“But mom it’s like a girls room. Can’t we redecorate it, so I can put up my posters and have some shelves for my trophies?” I asked,

“Tim your need to remember that money is short and now your sisters are grown up we may soon need to move to a smaller house, so I don’t want to redecorate another room as a teenage boys room, it wouldn’t help to sell the house.” Said mom.

Both these bits of news depressed me, I felt utterly defeated by the way mom was treating me. My only hope now was that my dad may be able to help.

“Oh yes,” said mom, “ Mrs Cartwright called today while I was out and said she wanted to talk with me when I came round with some dresses for the Mikado cast tomorrow, she said it was to do with your part. Do you know what this is about?”

I decided to duck this one. I knew mom would be mad when she found that I had told Mrs Cartwright about the purchase of the underwear, but I couldn’t face telling her myself even though I knew I would be in trouble. “I don’t know what it could be mom,” I replied.

Friday, when I got home from school mom descended on me straight away.

“ First Janette makes me look ridiculous in front of everyone with her attitude to your wedding photos and now you’ve been telling tales to Mrs Cartwright about my buying underwear for your role. She said she had talked to Miriam Jenkins about it and she said she thought it inappropriate for the role. So now you’ve made me look silly as well. I hope you are proud of yourself, you are becoming more and more like your father,” she shouted at me.

“But mom, it’s just that I saw how Miriam was dressed playing the role and it looked so much better.” I said.

“Better eh. Well you will be pleased to know I agreed that the peignoir should not be used, but as your wedding dress is tailored to fit you when you are wearing the corset, then that will have to stay. Oh, yes, and when you go up to your room you will find the makeup kit I promised you after your attempts earlier this week. You had better start practising because I have another nice surprise for you.” She said.

“Surprise, what surprise mom?” I asked

“ I have decided to have some photographs taken of my dresses to use as advertising and in a catalogue, Amelia is helping me as she does a lot of this herself with her wedding dress business. She is coming around here tomorrow morning to help take the pictures, so I want you to model the dresses for me, Teresa is coming around as well.” Said mom.

“But, mom, do I have to? Aubrey is coming here in the morning and then she is going with me to the swimming competition at school in the afternoon,” I said urgently.

“All right then, she is a pretty girl, if Aubrey helps model as well we should finish in time so you both go to the swimming,” mom said.” You had better see if that is OK with her”

I went upstairs and called Aubrey.

“You may not want to come now Aubrey,” I said, “Mom wants to make a catalogue of photos of her dresses and she wants you to help model them tomorrow morning if you come” I said wanting to put her off..

“But it sounds fun. Who else is modelling?” she asked.

“Just me and Teresa a nine year old from next door,” I replied.

“You mean your mom wants you to model for a catalogue of girls dresses, that’s really weird Tim”. She said.

“You think I don’t know that. It gets worse, she has just bought a whole host of makeup for me to use.” I replied.

“Tim, I am definitely coming. I want to see you and you said you had things to tell me didn’t you?”

“Yes, Aubrey, but its going to be awful, with mom in one of her weird moods and it’s all so difficult and embarrassing for me as well.” I said.

“We’ll get away as soon as we can and have that talk. I really want to help you Tim.” said Aubrey in reply.

“Thanks Aubrey I don’t know how I’d get by without you, thanks so much, I’ll see you tomorrow.”

With that we said goodnight and I tried to return to writing my letter to dad. I was on my third draft but I could still not find the right words for what I wanted to say.

I was usually first up on Saturday mornings, but this morning mom put her head round my door and said “Time to get up Tim. Amelia is here and its time to start getting you ready. After your shower just put on your bra, panties and a slip and the housecoat I gave you and come down for breakfast.”

This is going to be a terrible day, I thought as I slowly showered. Aubrey and young Teresa are going to be here as well, while I am parading around in mom’s dresses.

Amelia was at the breakfast table when I got downstairs, “Well here’s our beautiful model, good morning Tim, you look fetching in that housecoat. You are a good boy to help your mother with the catalogue.” she said.

I just said good morning and sat down with my breakfast, trying as I do on these occasions to tune out and think of something else. So I concentrated on today’s swimming session and my tactics for the races I was in.

When I had finished breakfast, mom said, “It’s time to go up to my bedroom and Amelia will put on your makeup for the photographs.”

“Is that necessary mom?” I queried, “I thought it was a catalogue of dresses.”

“It will be photographs of pretty girls wearing the dresses with you, Teresa and Aubrey doing the modelling, You don’t want to look like a boy wearing a dress in the catalogue do you?” said mom.

“I guess not mom,” I said as I walked resignedly upstairs.

Once upstairs, Amelia had me sit at mom’s dresser where she started to do a thorough job of applying my makeup, she spent a lot of time on my eyes, shaping my lashes and applying mascara, eye liner, eye shadow and pencil to outline the fair hair on my eyebrows.

“The eyes are important Tim,” she said, “With the right emphasis on your lovely wide eyes the rest is easy, you have a nicely shaped face, just a little emphasis on your cheek bones, here and here and now just a hint of lipstick and gloss on your lips and you will be perfect.”

“Next, we want you wear this wig today Tim,” said Amelia, holding out a blonde wig, it was long, below shoulder length and fell in a cascade of loose curls.

She placed a wig cap on my head first and then placed and adjusted the wig. I had never worn hair this long and found it strange to feel the hair resting on my shoulders and hanging down my back as I sat in the slip. I looked in the mirror at my fully made up face, now crowned by this mass of blonde tresses. I unconsciously moved to brush the hair out of the corner of my face and noticed how feminine this looked, a gesture I had seen girls do so many times as they preened themselves. Again I felt a strange tingle as I looked at myself.

At this point there was a knock on the front door. It was Aubrey. I heard my mom telling her to come upstairs where she would find me.

She walked in as I turned around, she stopped dead in her tracks.

“Is that you Tim? Oh my god you look awesome. So you are going to model for the catalogue then?” she said.

“I wasn’t given any option Aubrey, mom wants me to do it This by the way is Amelia her friend.” I explained.

“Yes Aubrey, and I understand you want to help as well. Let’s see if we can make you as beautiful as Tim,” said Amelia, “We’ve put all the dresses in Cathy’s old room Tim, you go in there now and your mother will help you into your first dress.”

So I said see you later to Aubrey and went into Cathy’s room and found my mom putting a little girls party dress onto Teresa.

“Why can’t I wear make up and have long hair like Timmy, I want to look like Timmy, “ Teresa cried out.

“Now, now Teresa, you will have to wait until you’re a big girl, stand still while I adjust this dress.”

“It’s not fair, Timmy’s not even a real girl and he gets to wear pretty underwear and make up and things.”

Shut up, you little brat I thought, this is bad enough without you going on about pretty underwear. This is going to be a long morning.

“Tim you put on that pink and green floral sun dress on the rail over there, be careful it has a flounce down the side which is meant to hang loose,” said mom.

I put on the dress and stood waiting until after a while Aubrey came into the room now fully made up, her beautiful hair did not need any further attention. Then mom made her take off her skirt and top, this in front of me, and put on a light green satin formal dress. Aubrey was only wearing a bra and panties so both she and I were embarrassed, I turned away. Again, I felt mom was getting way out of hand in this business.

“Come downstairs when you are all ready” said mom, and left us in the room.

“I’m sorry Aubrey to let you in for this, mom is out of control when she gets into one of these moods,” I said.

“Don’t worry Tim, I’ll see you through this. She can’t go on like this. Let’s just get this over with now and then we will plan what to do. Here let me adjust your dress, your bra strap is showing. I have to say though Tim you do look very good in that dress and your hair is wonderful,” said Aubrey trying to cheer me up.

We went downstairs where photos were taken by Amelia of the three of us, sometimes together, sometimes separately in front of a cloth background they had rigged up in the lounge, also there were some shots taken in the garden. We each wore four different dresses, each time changing in the same room. By the end I felt I really was a dress model, I couldn’t help noticing how I looked as I saw myself in Cathy’s full length mirror, there was no indication of Tim the boy, I looked like a teenage girl.

At the end I took Aubrey into my room to start to take off the clothes.

Aubrey looked around, astonished, “Is this really your room Tim? It looks like a girls room, why are your trophies on the floor?”

“It used to be Janette’s, mom has taken over my room for dressmaking and she won’t let me change it. Just wait here Aubrey while I go for a shower and get rid of this make up and stuff, I want us out of here.” I hurriedly said.

When I got back, showered and changed, Aubrey was standing looking puzzled.

“Tim, I hope you don’t mind, but as the doors were open, I looked in your wardrobes, all you’ve got is two school uniforms, four pairs of jeans and half a dozen T shirts and sweaters. Half of those are girls fit as well. The rest is all girl’s clothes in this wardrobe.” she said.

I explained again that money was tight and that I had often had to wear Cathy’s cast offs, and now had all the clothes she left behind when she went to college.

“Tim, this is just not right. For a start, Jason has a lot of clothes he never wears and I am going to get him to give them to you, his older stuff should fit you anyway,” Aubrey urged.

“And another thing Tim,” Aubrey continued, “What is this dress doing here in your wardrobe, it looks like a wedding dress?”

“It’s my dress for the Mikado.” I explained.

Aubrey removed it and held it up, “But it’s so elaborate, I mean it’s beautiful, but it’s better than some real wedding dresses I’ve seen and you will only be wearing it for two shows won’t you?”

“Yes, but for the whole of the second act, its really heavy and uncomfortable and I have to wear the corset underneath which is even worse.” I said.

“Our costumes are nowhere near as elaborate as this and a corset as well!, “This is incredible Tim and your mom wants you to wear all this as well? Said Aubrey.

“Its entirely mom’s idea, our drama teacher has already had an argument with her about what I wear when I come on stage before I put on the wedding dress and has asked her to tone it down.” I replied.

“Well I think that’s right. I really must come to your show, can you get me a ticket? Asked Aubrey.

“I’m scared enough already, but if you really want to come I’m sure I can get you a good seat, but you must promise not to laugh.” I said.

“Tim, I’ve already heard you sing don’t forget, You have a better voice than Felicity Chapman who is our Yum Yum and she isn’t a great actress either, nor has she appeared at the London Coliseum!” joked Aubrey, “No, Tim, I know you’ll be great in the role, I want to be there to cheer and applaud.”

“Its just having to dress up so much scares me. It’s weird, when mom tried the whole costume on me with the wig, makeup and everything and I looked at myself in the mirror, I was stunned when I saw how much like a girl I looked. Part of me was pleased I could do it so well, so convincingly, then I feel sort of ashamed that I’m enjoying it. Is it wrong of me to enjoy dressing up? I asked.

“Tim, you have to remember you are acting out a role.” said Aubrey, “To make it work properly you have to look like a girl, not like a boy in a girl’s dress, and no I can see how any real actor would be pleased if he could transform himself like you can, its nothing to be ashamed of. Look, I know you are also a first class athlete and that you can beat boys two years older than you are. If you have a problem it’s that you’re just too good at everything you try to do, the only thing you have to worry about is other people being jealous of you”

“That’s funny, that’s exactly what Cathy said to me, that she was jealous of me” I replied.

“Well, if it helps, I’m not jealous of you, I just happen to think you are the nicest boy I’ve ever met. Hey, shouldn’t we be heading for your school and the swimming competition?” Said Aubrey.

In answer I said, “Not before I hug the nicest girl I’ve ever met and Aubrey, thanks so much for saying that about acting out a role, that’s helped me a lot.”

Then we both got changed and ready, I picked up my sports bag and we cycled off to my school, Aubrey had borrowed Cathy’s old bike. When we arrived I took her over to the spectators area where there were just a handful of people, a few parents and some of the boys from school.

“I’m afraid there aren’t as many people here as at the Leisure Centre last week, do you mind?” I asked Aubrey.

“No Tim, in fact you can call me kinky if you want, but I rather like looking at a bunch of athletic guys in skimpy swimming briefs, one guy in particular however,” she said reaching for my hand, “Have I ever told you that you look really cute in those little speedos.”

“You know how to make a guy feel embarrassed, don’t you?” I said, reddening, “But that’s really nice to hear after this morning’s horrors. Thanks, I love you for that” As I said this I realised I had used the ‘love’ word, we had never said that to each other before.

Aubrey was now looking at me, her mouth slightly open and seizing the moment I moved forward, heedless of the people around and kissed her straight on the lips, turned and walked quickly into the changing room.

In the room, after I undressed, I had another shock. I noticed that the impressions of the bra straps could still be seen on my skin, I quickly draped a towel around my shoulders and sat like that while I waited my turn.

When it came to my races I was really wound up after the tension of the morning and my feelings for Aubrey, such that when I hit in the water, I raced flat out the whole way in both of them. Normally you pace yourself in relation to the other swimmers and try to leave a reserve for a strong tactical finish. This time I just swam hard paying no attention, just determined to swim the opposition into oblivion. I set up my best times ever and won both races and the second race was the one that won the competition for the school, so I felt elated and ran over to Aubrey and hugged her.

“That was brilliant, Tim, but next time can you dry yourself off first!” she said. However she hugged me back just as tightly. “Thanks for coming straight over though, I love you for that too, now you had better go back, I think your team mates want to congratulate you as well.”

I was really making a spectacle of myself, I realised and I took an amount of joshing from the rest of the guys in the team as I walked back over to them.

However the team captain came up and said to me “Tim, it was your last race that won the competition for the school, I want you to go up and collect the cup on behalf of the team, that’s if you can tear yourself away from your girlfriend,” as he slapped me on the back. Seb. Johnston was seventeen and a County champion as well as our Team captain so I was taken aback by his request, but he pushed me forward.

As I stepped forward to accept the cup I had a thought. If only my Dad was here to see me, as well as Aubrey, that would make up for all the trouble and torment I’m going through at home. Well, soon maybe, but I must finish that letter to him, the letter I was finding so difficult to write.

After I had changed I said to Aubrey, “Lets get some snacks and a drink from the shop at the corner then I want to take you somewhere for a picnic and our chat.”

We cycled off to Trensham Ponds and the same secluded overlook that Janette had taken me to.

“This is a lovely spot Tim, but why here, now?” asked Aubrey.

I told her all the news that Janette had given me about my dad and how he and mom broke up, when I mentioned the link with Amelia which Janette had noted, Aubrey immediately picked up on it.

“Tim, how long has your mom known Amelia? Aubrey queried.

“Not long I think. When I went to get fitted for the corset and stuff she greeted mom as if she had only spoken on the phone before” I replied.

“That can’t be right Tim, this morning I overheard her talk to your mom about having met your dad and an argument they had had and that you and Cathy were in the room at the time, that must be over seven years ago. Why should she lie? Were there other people in the room at the dress shop?” said Aubrey.

“Oh yes there were two other assistants. Do you think mom and Amelia were covering up for them and me about knowing each other? Why would they do that?” I asked puzzled.

“Tim, I don’t want to alarm you and I may be completely wrong, but I thought that your mom and Amelia were being more than just familiar and helpful to each other, I think they are really good friends, very close friends, if you understand?” said Aubrey.

“And you think that has something to do with how mom treats me, but how, why?” I asked.

“I think the only people who can answer that are your dad or maybe Janette,” said Aubrey, “Perhaps you could ask your dad? Have you written to him yet?”

“No I can’t figure out what to tell him and ask him. I don’t want to put him off by going on and on about my problems,” I replied.

“What do you really want to say?” she asked.

“That I miss him and I want to see him and talk with him, I want him to see me swimming, I want him to meet you,….” I said, but Aubrey interrupted..

“Why don’t you just write that and nothing more, you can leave all the talking and explaining for when he comes to see you. Tim, if he really wants to see you again that should be enough.”

“Yes maybe you’re right, I was trying to cover everything up front, I didn’t want to mislead him or risk that he would be disappointed in me.” I explained.

“Tim, I really could grab hold of you and shake you at times.” Said Aubrey earnestly, “The last thing any father of yours would be, is disappointed in you. Just write the letter, once he meets you and gets to know you he will be prouder than anyone, apart from me, that is.”

With that she grabbed me in a giant hug and I responded and held her tightly. We sat on the seat overlooking the lake until it was almost dark, sometimes we spoke but mostly we just cradled each other and started gently touching each other. I had never felt so close to anyone until that moment.

We rode home in the gathering darkness. Mom actually made us supper, even asked about the swimming. I let Aubrey tell her as she seemed to be getting on well with mom who had thanked her for helping with the catalogue photographs.

Afterwards as I walked with Aubrey to the station she asked me, “Tim, have you called Jason recently and fixed up meeting with him again? He was really impressed with the way you wowed them at the Opera and I think you both enjoyed the visit to the Bramfield Arena. Please call him and keep in touch, I think he’d appreciate that.”

“Well I am rather busy, with rehearsals, swimming and schoolwork, but yes Aubrey, if you want me to, I’ll call him. I feel bad about not being able to pay my way though, that’s why I haven’t been in touch, ” I replied.

We said our goodbyes at the station promising to meet if we could the next weekend, then I walked home, up to my room and started writing the letter to my dad. I vowed I would finish it that night. I still have the copy of the first draft I wrote, before writing a final neat version.

“ Dear Dad,

I hope you don’t mind me calling you “dad”, I’ve always thought of you that way rather than “father.” I can remember you from when I was 3 or 4, when you took me to the park and we kicked a ball around and played on the swings. I still go down to that playground and look at the one photo I have of us both together, I think it was taken in the park, you are holding me up on your shoulders and look as if you are shouting something. Janette told me you have a photo of me, is it the same one?

Janette said she had told you about what my hobbies and school activities are so I won’t repeat that here. Today I swam in a competition at my school and won both my races, I wished you could have been there. I really would like to meet you next time you visit England if you have time. There are so many things happening in my life I want you know about. I tried writing about them but when I wrote it down, it all seemed so trivial, I think its better if we could just talk about things. That’s what my girlfriend thinks as well, she told me not to worry, just keep my letter short.

There is so much more I want to tell you, but I will just say that I still remember you, I really want to meet you and talk with you and share my life, the nice things and the worries.

I need you dad, please come if you can.

Your loving son,

Timothy

I put it in an envelope and carefully addressed it and took it to the post box at the end of the road. Now it was on its way I felt a sense of elation, but also I thought about what Janette had told me about the conditions of the divorce. Could he really make contact with me and what would it do with the agreement with my mom? Then I was overtaken by another series of worries. Would it make my mom’s attitude even worse?

Then there was Aubrey, asking me to keep seeing Jason. If I was honest, part of me wanted to, but I was aware we were touching another area that gave me both pleasure and worry. There was a lot we had in common that made for a good friendship. But Jason’s feelings for me had another aspect to them, an aspect I felt as well, but did not fully understand.

One way and another I knew things would have to come to a head, between me and Aubrey and Jason, and just as importantly between me, my mom and my dad. I was beginning to realise that the next few weeks could set the course for the rest of my life, the thought filled me with both dread and anticipation.

++++++++++++++++++++++++++++++++++

To be continued

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Comments

WOW !!!!

Jezzi Stewart's picture

I think he should just take off and go to Janette's. Enough has been going on that a good lawyer could get him away from crazy mom. But he's too nice of a guy, most likely, and, most importantly, there wouldn't be a story. Keep up the good work!

BTW, waiting for dad to come rescue him is quite feminine - the white knight on horseback thing. Is that intentional.

The mystery of the mom/Amelia relationship is a nice touch.

What if Tim comes to the conclusion that he likes dressing/looking/acting like a girl for it's own sake, not just as an acting challenge? Aubrey accepts Tim's dressing now because it is acting and because he doesn't have a choice; will she accept a truly transgender Tim?

I hope Tim can stay friends with Jason without a romance. Jason certainly appeals to the girl that is being brought out in Tim by his mother's and his teacher's actions. But Tim is not an effeminate boy just waiting for that girl to come out, his masculine side will fight it, and has Aubrey to give reason. I think the masculine and feminine in Tim are pretty equally balanced and he could end up truly schizophrenic or in a nervous breakdown.

Congrats; you have really made me care about Tim and Aubrey.

"All the world really is a stage, darlings, so strut your stuff, have fun, and give the public a good show!" Miss Jezzi Belle at the end of each show

BE a lady!

"You have really made me care...."

Jezzi,

Thanks again for your comment/analysis of the characters in the story. I'm pleased in the way - at least with my 3 or 4 fans !!- that the characters are believable enough for readers to care about what happens to them.

On reflection, maybe I've made the nice guys too nice ( one reveiwer called Tim "terminally nice") and the nasty ones too nasty -but hey, this is fiction - but within the limits of the genre and of my limited (in fact, only) writing experience I've tried to make the characters have some depth - So thanks again, you've given memore encouragement to carry on with the story.

Luv & Hugs

Cindybelle.

Cindy

Mom is more than a few bricks shy of a load and her friend?

Poor Tim,

he'll be lucky to get out of his mom's and her loony friend's clutchs with his anatomy intact and funtioning.

Is mom bipolar, untreated paranod/schitz. , has a slow growning brain tumor -- something is seriously wrong with her. The oldest daughter seems healthy but the middle child could be showing early symtoms of metal illness, unless she simply went along with mom.

Mom does something hideously embarasing to her son and its *out of love or necessary for her livelyhood* or some such crock but he objects or someone else does and they are *bad like her ex* or *don't appreciate all she does for him*. She even twists his being forced to wear makeup as -- I quote this time,

>>“It will be photographs of pretty girls wearing the dresses with you, Teresa and Aubrey doing the modelling, You don’t want to look like a boy wearing a dress in the catalogue do you?” said mom.

Mom and maybe sis need help but Tim needs a safe place. At a minimum mom is dumping all her frustration on Tim. And what is with her friend, a man hater or just a friend?

Interesting characters and not your run of the mill forced fem story.

Sorry I didn't comment earlier. I don't often like this genra -- to each his/her own -- but this is special.

John in Wauwatosa

John in Wauwatosa

I think mom would have had Tim ...

Jezzi Stewart's picture

... in makeup no matter what he did or didn't do, but to be fair, Tim let "Timmie" get control for a moment and is responsible for giving mom an excuse for perhaps speeding up the feminization program, and also a basis (not that she needs much) for rationalizing that he wants it to happen. In the words of Professor Higgins, "Let a woman in your life ..." :-)

"All the world really is a stage, darlings, so strut your stuff, have fun, and give the public a good show!" Miss Jezzi Belle at the end of each show

BE a lady!

No one was harmed...

in the writing of this story and thanks John for calling it 'special'.

As I wrote earlier, I do believe in happy endings, so you can relax ! - What I'm tyring to do is tell a 'coming of age' story against a background of feminisation from his mom and the pressures of discovering his own sexual identity. This is an echo, in a very dramatised form ,of my own life experience at that age - hence some of the emotion I try to express.

My life turned out happily and I'm determined that Tims will as well - but lets not hurry:-) - adolescence seemed interminable at the time.

Cindybelle

Cindy

Thanks for the tip

I'm glad Tim's life will turn out okay.

This is a compelling story and you have developed some interesting characters. That *I* care what happens to them is a messure of how well you have crafted this. I only hope mom and the younger daughter come out of this whole and sane as well.

He is such a kind, intellegent and thoughtful child -- fictional as he is -- that to see him being abused for whatever reasons hurts. And I include the teacher for putting him in this position yet again of playing a female in front of the school.

I do some writing and beyond gud grammer and propper spelun the thing that many of my commenters ask for is *why*? What motivates a character to do what they do?

I look forward to more.

John in Wauwatosa

John in Wauwatosa

please

Please continue your beautiful story!!!!!

This is a story that I am

This is a story that I am waiting to read more of. You have made the story plot and characters in it very life like and true to life. I feel Tim is being pushed to femaleness by his Mother and her friend and his sister Cathy when she is around. Aubrey likes Tim either way and doesn't seem to mind that her boyfriend can also be her girlfriend. Jason is "hung up" on Tammy even tho he knows who Tammy is; so all in all, this is a complicated story that pretty much seems like a good soap opera. 'Tune into tomorrow for the next thrilling episode of Timmy's Life'. (giggle) J-Lynn

Me too.

laika's picture

Me too ......... I got all wrapped in this saga and was sad to see it go into such a long dormancy.
One can always hope. I've been pleasantly surprised before when a story that I liked,
but had almost forgotten suddenly popped back up. Hope you are well Cindybelle
and scribbling away at Part Five even as I write this.
~~~hugs, Laika

Holding my breath,

Interesting, not liking how some people want us, but it doesn't change that we like who we are. Timmy/Tammy. But would like to be oneself in doing it. Powerful. It goes in areas I haven't read other stories. A very unique writer.

Hugs again, Jessie

Jessica E. Connors

Jessica Connors

Good story

Enjoyed it very much,can't wait for next chapter.

Topanga

Do what your Mom asks...

... and you'll find a girlfriend who loves you for what you're going to become! My advice to a young hero/heroine! Get closer to Aubrey and keep away from that Jason! And Mom...be gentle! xx

I'm nervous about where this

I'm nervous about where this is going. Tim's mother is crossing the line here. Where is dressing up and modeling ok behavior ?

Cefin