© March 2013

Chapter One: Bad News

    Jonathon Phipps sat in the empty flat looking at the photo of himself and his ex girlfriend Kirstin. Jonathon had been very much in love with Kirstin, but his temper had forced her to leave him. Jonathon wasn’t the largest of men, and he sometimes found larger men would tease him about his size, and how much he was like a girl. He had got into more fights because of this than he could count.

    He’d been out one evening having drinks with Kirstin when a couple of drunken guys started hitting on Kirstin and him. They didn’t stop even after Jonathon explained that he wasn’t a woman.

    Jonathon lost his temper when one of the guys tried to kiss him, and Jonathon ended up getting into a fight, which saw him being taken away with the two guys that had started the trouble in the first place, when the police arrived on the scene.

     “What’s going on?” Jonathon asked the next day when he walked into the flat after the police let him go, and he saw Kirstin’s bags packed just inside the front door.

     “I can’t deal with this anymore Jonathon.” Kirstin said close to tears. “I’m sick of watching you get into fights every time someone makes a joke about your size.” She added with a pleading in her voice, but she didn’t know what she was pleading for, she had to watch helpless as she saw the person she loved become more and more out of control.

     “Those guys called me a woman and tried to kiss me! What was I suppose to do?” Jonathon asked angrily. “I showed them that I’m more of a man than they are.” He added with a manly grunt.

     “You can be such a sexist asshole sometimes.” Kirstin growled as she forced her way past him and headed for the front door.

     “Please don’t go, I’ll change.” He promised. “No more fighting...” He added as he tried to stop her leaving.

     “You already have changed, and I don’t like what you’ve become.” Kirstin said just before she picked up her bags and left. That was the last time Jonathon had spoken to Kirstin, and that was three months ago.

    Jonathon had been a much kinder person when he first met Kirstin, but he started a new job just after they moved in together, and he was soon spending more and more time going out with some of his work mates, and he started to act more like them because that’s what he thought a real man should be like. The trouble was, he ended up getting into fights, and he would demand Kirstin cook his meal and have sex whenever he wanted it, just like his new friends said their wife’s and girlfriends did for them.

    Now for the past three months he’d been on his own, unable to find another woman to put up with him, and he missed Kirstin. Jonathon felt even more alone because he’d lost his mother to cancer a couple of years back, and he’d had a falling out with his father because he called around to check on him, and he found that his dad had been seeing another woman. Jonathon never bothered hanging around to meet this new woman, he just found her clothes scattered all over the bedroom, and Jonathon was angry that whoever this woman was, she had already made herself at home in his parent’s house.

    His father had called trying to explain that it wasn’t what he thought, but Jonathon had hung up on him, but not before telling his father to never call him again, and as far as Jonathon was concerned, his father was also dead to him.

    Jonathon had always argued with his father, and it was only his mother that managed to keep the peace between them, so with his mother gone, Jonathon stuck to his guns and never spoke to his father again. Jonathon blamed his father on some level for his own small size, because his father wasn’t a tall well muscled man either, but unlike Jonathon, his father was happy with the way he looked.

    He was snapped out of his thoughts when the phone rang, so he placed the picture back down on the coffee table and picked up the phone.

     “Hello...?” He asked.

     “Is this Jonathon Phipps?” A woman asked on the other end of the line.

     “Yes, this is Jonathon Phipps.” He answered.

     “Hello Jonathon. I’m sorry to be the one to tell you this, but it’s your father.” The woman said.

     “What about him?” Jonathon asked in a flat tone.

     “He passed away in the early hours of this morning. I’m so sorry for your loss.” The woman said with sorrow in her voice.

    Even though Jonathon hadn’t spoken to his father in a couple of years, he was still shocked to hear that his father was dead, and he’d never get the chance to make things up between the two of them.

     “How did he die?” Jonathon found himself saying.

     “He’d been ill for some time, and he died peacefully in his sleep.” The woman explained.

     “Is there anything I need to do?” Jonathon asked. “I’m sorry, but I don’t even know your name Miss...?”

     “I’m Mrs Joan Green, and I’ve been taking care of your father’s affairs for him these past couple of months.” She started to explain. “He knew he was going to die, so he got all his affairs in order and made you the benefactor of his estate.” She added.

     “Did he have much to leave?” Jonathon asked, not sure if his father had anything worth leaving or not.

     “He owned his own house, and the mortgage was all paid up, and he had some money in the bank as well.” Joan said as it sounded like she was reading it from a piece of paper. “I just need you to come down here and sign some paperwork and help to sort out the funeral.”

     “I’m not sure what help I’ll be with the planning.” Jonathon said with a shrug. “My father and I haven’t spoken in nearly two years.” He pointed out.

     “Your father took care of most the details, but he did give me an envelope for you, and we need you to sign this paperwork, as you’re the last relative still alive.” Joan explained.

     “Alright, I can come down tomorrow.” Jonathon said, as he was between jobs at the minute, and he had nothing else to do, other than drink more whisky while feeling sorry for himself.

     “That’s wonderful.” Joan said with a smile in her voice. “I’ll book you a room at the local hotel for a couple of nights while we get everything sorted out.” She added.

    Joan gave Jonathon all the details on how to find the office she worked at, and Jonathon said he’d see her the next day before ending the call. Jonathon spent the rest of the night drinking whisky and thinking about his dad, and some of the things they argued about.

    David, Jonathon’s father had never been a man’s man, but he always tried to make sure Jonathon had a father he could be proud of. Jonathon didn’t like sports, but his father still pushing him to do them, just made them argue even more. David and Sarah, Jonathon’s mother had made their marriage work for thirty years before Sarah died of cancer, and Jonathon found his father was seeing another woman so soon after her death.

    Jonathon finally made his way to bed after packing a bag for a couple of days away from home. His father was only a couple of hour’s drive away, but Jonathon wasn’t going to pass up on a couple of nights away from home stopping in a hotel.

    Jonathon had made good time, and he found a place to park just down the road from the building where Joan Green worked. Jonathon was a little shocked when he saw the name of a solicitor’s called ‘Green and son’s Solicitors on a brass plaque to the side of the main entrance. It was a modern looking building that had been built since he moved away; it was all glass walls and marble looking floors. He made his way into the building and told the woman on reception his name, and she said he was expected and then she explained where he needed to go.

     “Hello, I’m Jonathon Phipps; I have a ten o’clock appointment with Mrs Joan Green.” Jonathon said nervously as he entered the part of the building the receptionist directed him to, and he found another woman sat behind a large desk.

     “Good morning Mr Phipps, Yes Mrs Green is expecting you.” The woman said with a smile. “Please take a seat and I’ll let her know you’ve arrived.” She added as she pointed him towards a sofa across from her desk.

    Jonathon took a seat and picked up a magazine to look through; he was shocked to see that it was the latest issue of the magazine, and not something that was ten years out of date. He’d just started reading an article on some famous rap artist that was fronting an anti-drug campaign after getting out of rehab, when he realised that a woman was stood in front of him.

     “I’m sorry.” Jonathon said as he put the magazine down and got to his feet to greet the woman.

     “Don’t worry about it Mr Phipps.” The woman laughed as she held out her hand to shake Jonathon’s. “I’m Joan Green; we spoke on the phone yesterday.” She added. “I’m sorry that we’ve had to meet under these circumstances.”

     “So am I, and please call me Jonathon.” He smiled back as he shook her hand.

     “Okay Jonathon and you must call me Joan.” She smiled back at him. “Please follow me into my office, and I’ll explain things to you over a cup of coffee.” She added as she turned around and made her way back into the room she must have come out of.

    Joan wasn’t a young woman, but she’d taken good care of herself, and Jonathon couldn’t help checking out Joan’s slim figure as he followed her into her office.

     “Please take a seat and we can get to know each other a little better.” Joan said as she directed Jonathon over to a large sofa she had over near the window. “I hope you don’t mind me saying this Jonathon, but you do look a lot like your father.”

    Jonathon used to get upset when people said he looked like his father, but he just couldn’t bring himself to get upset with Joan, she was just too much of a nice person to get angry with. “He used to say I looked like my mother.” Jonathon chuckled.

     “I can see both of them in you.” Joan said looking thoughtful as she studied Jonathon’s face in more detail.

     “You knew my mother as well?” Jonathon asked.

     “Sadly not, but your father showed me some pictures of her.” Joan explained. “He was very much in love with her you know, and I don’t think he ever really got over her death.” Joan added with a sad look in her eyes.

     “He had a funny way of showing it.” Jonathon said tinged with anger over what he’d found at his parents’ home the last time he was there.

     “Your father wasn’t seeing another woman Jonathon.” Joan said.

     “I know what I saw, and nothing you can say will make me think otherwise.” Jonathon snapped, his temper getting the better of him.

     “Did you see this woman in your father’s house when you were there that day?” Joan asked, not letting Jonathon’s sudden mood change bother her.

     “No, but I saw all the clothes in his bedroom, and none of it belonged to my mother.” He smiled sarcastically.

     “Did you ever read any of the letters your father sent you after you stopped talking to him?” Joan asked.

     “No, I was too angry over what I saw in the house, so I just threw them all away, and then he stopped sending them.” Jonathon said.

     “Will you read this one?” Joan asked as she held up a posh looking envelope with his name wrote on the front in his father’s handwriting.

     “It’s the least I can do now he’s gone.” Jonathon said as he tried to fight back the tears he wanted to shed. He quickly wiped away a tear that was running down his cheek.

    Jonathon took the letter off Joan in a shaky hand, and he looked at it for the longest time. He realised that this would be the last thing he ever read from his father, and that his father had died thinking his son hated him. Jonathon took a couple of deep breaths to steady himself again before he opened to letter and started reading it.

 

    Dear Jonathon

    If you’re reading this letter then it means I’m no longer with you. I wish we could have talked before I died, but no matter how many times I reached out to you, I never got a reply, so I’m asking my good friend Joan to give you this letter for me in the hopes you will sit and read it.

    Before I go on to explain everything to you, I want you to know that I died loving you as much as the day you were born, and I know that you were hurting over the death of your mother. I was hurting as well, but we both dealt with her loss in our own way.

    I can say with my hand on my heart that your mother was the only woman I ever loved, and ever slept with. I know what you saw that day you called in to see me, but it wasn’t another woman living in our house. The female clothing you found was mine. I was a crossdresser, and your mother knew all about it, and she even enjoyed spending time with her part time best friend.

    I thought that letting Donna out, might make me feel better at the time, but all it did was drive us apart, and for that I am sorry. I must explain at this point that Donna is the female name your mother gave me when I was dressed as a woman. I know you must think me all sorts of things at this point, and you may even find this all hard to believe, but Joan has a folder with some pictures of me and your mother doing things together as two girlfriends.

    Joan’s husband was one of my closest friends and he was also a crossdresser like me. That is how I got to know Joan. I did ask if it would be alright for me to tell you that little detail and she said I could.

    So now you know my darkest secret son, and I hope you can forgive me, as I’ve forgiven you. Your mother wouldn’t be happy to see how we drifted apart, and I hope that by the time you’re reading this, your mother and I are sat on a cloud making each other laugh, just like we did when we were alive.

    I’ve left you everything I own, and I’ve also taken care of all the funeral costs, so if you don’t feel as though you can forgive me, Joan will take care of everything and you can just walk away and pretend that I died two years ago.

    With all my love.

    David (Donna) Phipps.

 

    Jonathon folded up the letter and placed it back in the envelope before he put it on the sofa next to him. He’d had to stop reading the letter a couple of times due to his eyes filling up with tears and stopping him from being able to see. He couldn’t hold back the tears anymore and he just broke down and sobbed like a baby. Joan moved closer to him and he was soon being hugged as he sobbed, and he didn’t care what anyone thought of him at that moment, he was morning the loss of his father.

     “How are you feeling now Jonathon?” Joan asked once he’d finished sobbing and he was just letting Joan hold him.

     “I feel like such a fool.” He admitted.

     “You feel like a fool for crying?” Joan asked, not understanding what Jonathon was getting at.

     “No, I feel like a fool for hating my father all this time.” He chuckled as he sat up and wiped his eyes with the tissue Joan offered him.

     “So it doesn’t bother you that your father spent some of his time dressing as a woman?”

     “It might have if I’d found out while he was still alive, but now I find myself wondering what he looked like.” Jonathan admitted.

     “I can help you with that.” Joan said as she picked up a folder and handed it over to Jonathon.

    Jonathon remembered his father saying in the letter that Joan had a folder with pictures in it, so he sat back and opened the folder. He let out a gasp when he saw a picture of his mother stood next to another woman, and they both looked really happy together.

     “Is that Donna?” Jonathon asked as he ran his finger along the picture.

     “Yes, all the photos in there are of your mother and father, or Donna as she liked to be called.” Joan said with a sad smile.

    Jonathon was shocked at just how good his father looked while dressed as a woman. He found some photo’s of Donna with Joan and another woman.

     “Is this your husband?” Jonathon asked as he held up the folder for Joan to see.

     “Yes, that is my Jenny.” Joan said with a tear in her eyes now. “They were a right pair when they got together.” She giggled.

     “I’m sorry I’ve upset you Joan.” Jonathon said as he closed up the folder and he gave Joan a hug this time.

     “You’re so much like your father, just much younger looking.” Joan giggled as she let Jonathon hold her.

     “Thank you for that Joan. I just wish my father was here to see it.” He sighed.

     “I think he knew all along.” Joan said as she sat up again. “He never once had a bad thing to say about you.” Joan added with pride in her voice.

     “I wouldn’t have blamed him if he had.” Jonathon admitted. “I hope you don’t mind me saying, but I think you better do something with your face.” He pointed out.

     “Do I have panda eyes?” Joan asked with a giggle.

     “Panda eyes...?” Jonathon looked puzzled.

     “That’s what we call it when a woman makes a mess of her eye makeup.” Joan explained as she got to her feet and retrieved her purse out a desk draw and sat down to fix her makeup.

     “You learn something new every day.” Jonathon chuckled. “Or more than one thing in my case.” He added as he thought about the fact he’d just found out that his father spent some of his time as a woman called Donna, and his mother had known all about it.

    Joan soon had her makeup fixed and then she picked up her phone and called out to her assistant and asked her to bring them in some coffee. Jonathon and Joan then got to work sorting out all the paperwork, and by the time it was midday, Jonathon was the new owner of all his father’s property and bank accounts, or he would be once all the papers had been filed.

     “Will you let me treat you to a spot of lunch?” Jonathon asked once they had finished.

     “No, but I’ll buy you lunch.” Joan smiled.

     “Okay.” He agreed.

Chapter Two: Trying new things.

     “I’m sorry, but I’ve not had time to find you a hotel yet.” Joan said while they were enjoying their lunch.

     “That’s alright, I was thinking of stopping at my father’s place anyway.” Jonathon said. “I do own the place now, or I will once all the paperwork has gone through.” He added.

     “I think your father would like that.” Joan smiled.

     “What was he like as Donna?” Jonathon asked, still having trouble picturing his father as the woman he’d seen in the photos.

     “I always thought he was more himself as Donna.” Joan said looking thoughtful. “He dropped all the macho stuff and became a much happier person to be around.

     “Sounds like we’re more alike than I first realised.” Jonathon admitted. “So were you and my father close?” He asked.

     “Yes, but not in the way you think.” Joan started to explain. “I was close friends with Donna more than David. He was there for me when I lost my John. We kind of became best friends to each other.” Joan said looking thoughtful.

     “I’m thinking of stopping down here for a while, I hope we can get together, so I can find out more about my father and his secret life as Donna.” Jonathon looked hopeful. “I was between jobs, so I don’t have anything to rush back for, so I might as well move into my parent’s place and save some money.”

     “I’d like that, and it would be nice to have someone to talk to about him.” Joan smiled. “I don’t have anyone in my life that understands any of it.” Joan added with a sigh. “You’re not short of money now, but I can understand you not wanting to waste it on a place you’re not living in.”

    Joan had driven them to the restaurant. So she drove them back to the office and Jonathon left to head over to his parent’s home and see how the place looked after two years.

    Jonathon pulled onto the empty driveway outside the house he’d grown up in, and he just sat there looking up at the building. He thought it looked the same as the last time he was here two years ago, but he knew that his father wasn’t inside this time, and never would be again.

    He got out the car and pulled out the set of keys Joan had given him and the card with the alarm code on it. The alarm was new to Jonathon, so he didn’t know the code for it.

    Once inside the house, he noticed that the place had been redecorated, and it had a more feminine feel to it, which made Jonathon wonder how much time his father spent as Donna after he stopped coming to see him.

    Jonathon made his way into the kitchen expecting to find the fridge full of mouldy food, but it had been cleaned out, but left on ready to use. He wondered if Joan might have turned it on expecting him to come here and stay, rather than stopping in a hotel.

     “I’m home, mum, dad.” He said to the empty house. “Sorry for being such an asshole to you dad.” He added with a chuckle.

    Jonathon couldn’t hold back the tears anymore and he fell onto the sofa in the living room and sobbed his heart out again. He sobbed because of everything he’d lost in the past two years, and the fact he blamed his father for something he never did, and it was too late to ask his forgiveness, even if he’d already had it in the letter his father left him.

    He finally pulled himself together and carried on walking around the house. He was shocked to find his room just the same as it was the last time he’d been at home. All his books and models were in the same place, but with a layer of dust covering them. He went into his parents room expecting to find women’s clothes all over the place, but it was clean and tidy with the bed made, just like it use to be when his parents were alive.

    Jonathon went over to the wardrobe and opened the doors, he found one side was full of suits and male clothes, and the other was full of female clothing and wigs.

     “So this is all Donna’s stuff then?” He asked the empty room as he ran his hand over some of the fabrics in there. “I wish I could have met you Donna.” He added with a sad smile.

    Jonathon suddenly remembered meeting a woman while he was very young, and her name was Donna. His mother had called her Aunty Donna, but she stopped coming to visit as Jonathon got older.

     “Was that you dad? Did I actually get to meet you as Donna?” He asked the clothing like it might answer him.

    He closed up the wardrobes and then made his way back down stairs and into the kitchen looking for something to drink, but the place had been cleared out, so he decided to get in his car and go do some shopping. If he was going to be stopping here for a while, he would need to eat.

    Jonathon had put all the shopping away, and had placed a ready meal in the oven to cook while he went into the study and fired up his father’s computer. The machine was password protected, but Jonathon had a pretty good idea what the password was, and he was right, his father always used his mother’s date of birth or his, and the password was his date of birth. Jonathon wondered if this was another way for his father to say he forgave him.

    He took a quick look around the files and found a number of mpeg movies in one file, all to do with putting on makeup, so he played a couple of them. He was quite impressed as he saw a male face slowly become that of a female. He had to stop when his dinner was ready, but he knew he’d be giving the other movies a look at some point.

    Once he’d finished his dinner and washed what little dishes he’d used, he returned to the computer to carry on looking for more info on Donna. He found a folder with his name on it, and when he tried to open it he found out it needed a password. He tried his date of birth first, and it told him he was wrong, and only had one chance left to get it right. Not being worried by this, he typed in his mother’s date of birth and the folder opened.

    Jonathon found himself looking at a list of account and passwords for all the email addresses that Donna owned, as well as other details.

    Hello Jonathon

    I’m really glad you’re reading this, that means you didn’t run away again *Smile* in this folder you will find every bit of information on Donna that you will need. I made a lot of friends around the world during my time as Donna, and I need you to contact them and let them know I passed away. I know it’s not going to be an easy thing for you to do, but you could find out some things about your Aunt Donna along the way. *grin* Yes I was your Aunt Donna.

    Jonathon couldn’t stop himself from laughing after reading that little bit of information, even if he had worked it out for himself earlier. He opened some of the files he found in the folder and was soon opening up Donna’s email account and looking at all the contacts she had made. Jonathon couldn’t think of Donna as anything but a woman, so that’s why he decided to think of her in that term. Donna seemed like a lot of fun to be around anyway, judging by the opening note he found from her.

    He spent some time drafting out an email to send to all the people in Donna’s contact list, and then he sent it once he was happy with how it read. It didn’t take long for him to start getting replies from Donna’s friends, thanking Jonathon for letting them know the sad news, and offering to talk to him if he needed a shoulder to cry on, in a cyber way.

    While he was waiting for more people to reply, Jonathon launched Donna’s Skype account, and he was soon being invited to chat to a couple of Donna’s friends from Canada. He was nervous about talking to them in the beginning, but he soon relaxed, and started to hear some stories. Jonathon even found out Donna had wrote a couple of stories, which he made a note off and said he would go and give them a read later.

    Time got away from Jonathon, and it was the early hours of the morning when he finally called it a night and shut down the computer before going to bed. He decided to sleep in his parent’s bed, rather than his old room at the house. He was out of practice sleeping in a single bed, and that is what he had in his old room at his parents.

    Jonathon was sat with a mug of coffee and a slice of toast the next morning when he got a text message on his mobile. He smiled when he saw it was from Joan. She was asking how he was doing, so rather than text her back, he decided to call her and have a chat instead.

     “Hello Jonathon, you didn’t need to call me back.” Joan said with a smile in her voice. “How are you feeling about everything you found out yesterday?” She asked sounding worried.

     “I’m doing as well as can be expected, given what I found out.” Jonathon sighed. “I emailed all of Donna’s contacts and let them know what happened.” He added.

     “I know; I found one in Jenny’s email account last night when I checked it.” Joan said.

     “Do you think it read alright? I was a little worried about what to say.” He admitted.

     “I thought it was well written, and I’m sure that all of Donna’s friends would have thought the same.” Joan sounded proud of Jonathon.

     “Thank you Joan. I’ve already had some replies, and I even had a chat with a couple of girls from Canada.”

     “I’m glad that you’ve been talking with some of Donna’s friends, and I bet they will want to chat with you again.” Joan giggled. “They all love some good gossip.” Joan added in a fake whisper.

     “I was wondering if you felt like joining me for a spot of dinner this evening after you finish work.” Jonathon asked nervously.

     “Sounds like fun, where do you want to eat?” Joan asked.

     “I was hoping to eat here at my parent’s place... I mean my place; I’m not a bad cook.” Jonathon had to correct himself over who the house belonged to now.

     “That sounds even better.” Joan sounded excited now. “I’ll come over for seven, is that alright?” She asked, trying to brush over Jonathon’s little slip.

     “That’s perfect; I’ll see you later then, bye.” Jonathon said with a smile in his voice. He was happy to have someone to talk to, and he did like spending time with Joan, she reminded him a lot of his mother.

     “Until later then, bye.” Joan replied just before she ended the call.

    Jonathon had everything in that he would need to cook the meal, so he had the whole day to himself; he was soon sat at his father’s computer again checking to see if he’d had anymore replies. There were a couple, so he wrote back to them to thank them for their kind words. He then found himself going through the videos again; he was still stunned to see how some of the men in the videos could go from looking so plain as a man to looking quite sexy as a female. Jonathon even thought his own father had looked quite sexy as a woman, but his father wasn’t a tall man, and he had a very pretty face, which meant he passed very easily as a woman when he was dressed.

    Taking a break from watching the how to put makeup on videos, Jonathon went to make himself a drink, and he ended up in his parent’s bedroom again. He found his father’s makeup and started going through some of it. Jonathon recognised some of the things from the videos, and he opened one of the lipsticks to check out the colour.

    Looking in the mirror, and then down at the deep red lipstick again, Jonathon was soon sat at the dressing table applying the lipstick to his own lips. It took him a couple of tries to get it looking right, but he was soon sporting a set of deep red lips that looked very kissable.

    Happy with the way his lips looked, he decided to try some of the other things he’d seen on the videos, so he started to play around. He found the things to make his eyebrows vanish, which was a glue stick and some stuff called cover up, and he started to copy what he’d seen in the video. He thought he looked weird when he’d finished. He’d added some foundation to his face, and he now looked more like a woman than a man.

    Finding a curved piece of card, he soon had some thin eyebrows pencilled in, and then he set to work on his eye shadow and mascara. He added some false eyelashes, which took some practice to get in the right place, but he did it in the end, and then he added the mascara.

    Jonathon was quite shocked by the time he finished. Sat at the dressing table looking back at him was a short haired woman in her early twenties. Lost in the moment, Jonathon was soon going to the wardrobe and pulling out one of the wigs he’d seen in there, and he went back to the mirror and started to fit it to his head. He found a wig cap and placed that on his head to cover up his own hair, and then he placed the wig on and pinned it in place, just like he’d seen in the videos.

    He giggled as he looked at the woman in the mirror with her long curly blonde hair framing her face. Jonathon was getting quite turned on as he watched his male self vanishing, to be replaced by a cute looking girl.

    Looking at the open wardrobe in the mirror, and seeing all the female clothing just hanging there, Jonathon was soon on his feet and looking for some underwear to put on so he could try out the full look of being dressed like a female.

    He soon found the underwear, and he stripped out of his clothes, this was tricky to do because of the wig, but he didn’t want to take it off again. Once he was naked, he picked up a bra and had some trouble trying to get it on, but he remembered watching Kirstin put a bra on once, and he copied that. He was glad that he and his father were about the same size, because this meant all Donna’s things fit him perfectly.

    Once the Bra was on, he found a set of breast forms and slipped them into the cups and then he giggled as he felt the weight pulling on the straps as they went over his shoulders.

    Next he found a pair of panties that matched the bra and he slipped them up his legs. He loved the soft silky feel of the fabric as it went up his legs. He’d also spotted a patted girdle in the same draw, and he was soon pulling that on as well. He’d seen a guy in one of the videos tuck his manhood between his legs, so he did the same.

    Jonathon thought it felt a little odd to have his penis tucked away like he did, but he did like the way it looking when he looked in the mirror. He was soon wanting to do more, so he found some pantyhose and sat on the edge of the bed to put them on. This proved to be harder than Kirstin had made it look, but he managed it and was soon looking at Donna’s dresses to see what he liked the best. He found a little black number he liked the looks of and was soon stepping into it and having trouble getting the zipper closed.

     “How do woman ever get dressed on their own...?” Jonathon asked the empty room as he turned this way and that trying to get the zipper closed.

    He finally managed to get it closed, and he went to check himself out in the mirror. Jonathon was quite shocked at what he saw looking back at him. The girl wasn’t the most pretty, and she could do with waxing her legs, and needed a little more practice with her makeup, but for the most part he thought he made a nice looking woman, just like his father did in all the photos he’d found. Jonathon now looked like he could be Donna’s daughter.

     “I need shoes.” He said to the girl in the mirror as he looked at her stocking covered feet.

    Donna had a large collection of shoes and boots to choose from, and it took him some time to find a pair that he thought he might be able to walk in. They were a pair of shiny black pumps with what looked to be around three inch heels on them.

    Sitting on the edge of the bed again, he was soon wearing the heels and trying to walk around the bedroom in them. The heels felt much higher now he was wearing them. It took him some time to feel safe not holding on to something, but he slowly started to walk around the room.

    Jonathon looked at himself in the mirror as he walked back and forth with his larger looking hips swinging from side to side, all thanks to the heels. He found himself getting excited when he saw his breast jiggle when he took each step. He’d never realised just how exciting it could be to wear female clothing.

    Not ready to end this little adventure, Jonathon left the bedroom and made his way to the kitchen so he could make himself a sandwich for his lunch. He found it a little odd having to look over his breast to see what he was doing, and it was tricky trying to make a sandwich and not get messy doing it.

    Jonathon found himself walking around the kitchen more than he needed to, as he loved the sound of his heels clicking on the hardwood floor. He giggled when he realised that it was ‘his’ heels making that sound.

    Once he’d finished making the sandwich, he took a seat at the kitchen table to eat it. This felt weird to him, as he sat down on the wooden chair and felt his padded bottom being squished. He had to lean forward to eat his sandwich, so as not to get crumbs on his dress, or more to the point the chest area of his dress that was being pushed out by his breasts.

     “Looks like I’ll need to visit the powder room when I’ve finished my lunch.” Jonathon said in a breathy sounding voice, trying to sound more like a female, when he saw the lipstick mark on the lip of the glass he was drinking some orange juice from.

    The powder room was actually his parent’s bedroom, because that is where he’d left the lipstick he’d used earlier in the day. He sat and added some more to his lips, making them look red and shiny again. He started looking through the wardrobe again and he was soon trying on some other dresses, he even found a pair of figure hugging black jeans and some boots that came just over the knee and looked like something a pirate would wear, except for the three inch heel they had. He had also found a white peasant top to wear, and he was soon walking around the house again looking at himself in any reflective surface he could find.

    Lost in the fantasy of pretending to be a woman, and trying on all the different outfits his father had owned, Jonathon had lost all track of time until he heard the local church bells telling him it was four in the afternoon.

     “Oh crap...!” He shouted as he looked at the clock on the wall and saw the time.

    He started to get undressed, and actually felt a little sad to be removing everything, but he wasn’t ready to be seen by Joan or anyone, while being dressed as a woman. Once he was undressed, he decided to jump in the shower to wash off all the makeup.

    On returning to the bedroom he looked around the room and realised he needed to put all the clothes away, so with a towel wrapped around his waist he set to work.

    Jonathon managed to get dinner sorted out, and he had the dining table set when the doorbell rang at just before seven.

     “Hello Joan, I’m glad you could join me.” Jonathon smiled as he opened the door and let her into the house.

     “I’m the one that’s glad you wanted to spend more time with an old goat like me.” Joan laughed as she let Jonathon help her off with her coat.

     “You’re not that old.” Jonathon argued. “I’d still chat you up if I saw you in a bar.” He added with a smile.

     “You’re a breath of fresh air to have around.” Joan blushed. “I brought us some wine to have with the meal, but I wasn’t sure what you were cooking, so I brought a red and a white.” Joan added as she held up the gift bag with the wine bottles in.

     “Will you be okay to drive home again later if you have some wine?” Jonathon sounded worried about Joan being stopped and losing her licence if she’s over the drink drive limit.

     “I already thought of that and got a taxi over here, so I can have a drink, and not worry about needing to drive home after.” She smiled.

     “I’ll pour us both a glass out then.” Jonathan grinned as he led the way into the living room.

    Joan took a seat on the sofa, while Jonathon poured them both a glass of red wine. Then he joined her on the sofa to enjoy her company while he waited for the dinner to finish cooking.

     “Thank you.” Joan said as she took the wine glass off him. “This place doesn’t feel right without your father pottering around.” She added as she looked around the room.

     “I miss both my parents, but it’s my mother I miss the most.” Jonathon admitted. “I think that was the main reason for me not coming back for two years. I always thought I would have time to patch things up with my dad.” He added with a sigh.

     “Your father understood your reasons, and he did try to contact you when he found out he was dying, but he still loved you.” Joan tried to comfort him.

     “I better go and check on dinner.” Jonathon said as he got to his feet and went into the kitchen. He didn’t want Joan to see him getting upset again.

    The two of them were soon sat at the dining room table enjoying steamed salmon, salad and jacket potato. Joan was quite impressed with Jonathon’s cooking skills.

     “This is really nice, where did you learn to cook like this?” Joan asked half way through the meal.

     “My mum and dad taught me while I was growing up.” Jonathon shrugged like it wasn’t a big deal. “Did my father ever cook for you?” He asked.

     “Yes he did, well it was more Donna than your father that did the cooking.” Joan smiled as she looked to be remembering some of the good times she’d had with Jonathon’s father.

     Jonathon noticed Joan looking at him in an odd way and he started to worry that she might be expecting more than just dinner. He jumped when Joan spoke to him again.

     “Did you get up to anything interesting today?” Joan asked in a matter of fact way.

     “Nothing much, just looked around the place, trying to work out what I wanted to keep, and get rid of.” Jonathon shrugged. He went back to eating his dinner when he saw Joan studying his face.

     “How far did you go?” Joan asked with a smirk.

     “How far did I go where?” Jonathon asked, not understanding the question. “I’ve not left the house today.” He added with a puzzled look.

     “I mean did you just try out the makeup, or did you go all the way and get dressed as well?” Joan was grinning now.

     “I don’t know what you’re talking about.” Jonathon said, getting flustered as to how Joan knew what he’d been doing.

     “I can see the traces of makeup around your eyes.” Joan grinned. “I bet you never used any makeup remover did you?”

    Jonathon thought about lying to her, but a small part of him was glad she already knew the truth, even if he did feel shame over what he’d spent most the day doing. “No, I just washed it off in the shower.” He said looking down at the table, and the remains of his dinner, which he’d lost his appetite to eat.

     “It’s nothing to be ashamed of Jonathon.” Joan said in a comforting voice. “You still haven’t answered my first question though. Did you just use the makeup, or did you try dressing as well?” She asked again.

     “I dressed as well.” He replied in a small voice that was just above a whisper. “I don’t know what came over me.” He added, still not able to make eye contact with her.

     “How did it make you feel?” Joan asked, still using the same calming tone of voice to let Jonathon know she wasn’t shocked by any of it.

    Jonathon finally looked up and met her eyes, and he looked to be thinking about how to answer her question. It did help Jonathon to see that she was smiling at him, but not in a mocking way.

     “I liked it, I liked the way the clothes felt, and the fact I looked pretty, not plain like I do right now.” He admitted with a sigh, like a large weight had been lifted off his shoulders. “Does this make me gay?” He asked with worry in his voice.

     “I’m not sure.” Joan shrugged. “Did you want to be held by a man while you were dressed, or have a man make love to you?”

     “No...!” Jonathon snapped, looking shocked. “I just liked the fact I looked nice, but I never once wanted a man to see me, or touch me while I was dressed.” He added, sounding as macho as he could.

    Joan couldn’t help giggling when she saw how Jonathon was trying to act more manly. “I’m sorry Jonathon, I’m not laughing at the fact you tried dressing as a woman, it’s just that you’re trying to act all macho now.” She giggled some more.

    Jonathon opened his mouth to argue with her, but he stopped when he realised just how silly it was to act all macho when they were talking about the fact he’d spent most the day wandering around the house wearing female clothes, makeup and a wig. “I guess it is a little silly of me to act that way.” He laughed himself.

     “To answer your question, I don’t think you’re guy.” Joan smiled. “I just think you finally got in touch with your softer side, and you had some fun doing it.” She added.

     “What brought on this sudden urge to wear female clothes and makeup?” Joan asked. “Have you ever done anything like this before?”

     “No, not that I can remember.” Jonathon said as he tried to remember if he’d ever felt like wearing female clothes before today. “I was looking through some of the videos my father had on his computer. Some of them were how to apply makeup, and I found it a bit of a turn on, and before I knew it, I was having a go.” He admitted.

     “So you started with the makeup?” Joan smiled as she pushed him to keep talking about it.

     “Yes, I did my makeup and then added a long blond wig.” He let out a sigh as he thought back to how he remembered looking earlier. “As I looked at myself in the mirror, I saw the open wardrobe behind me, and I just had to see what I looked like as a woman from the ground up.”

     “Do you think you’ll do it again?” Joan actually sounded hopeful he’d say yes to this question.

     “I felt sad when I had to get changed back, so I would have to say yes, I will be doing it again.” Jonathon admitted.

     “Do you want me to help you do it right?” Joan asked.

     “Help...? In what way?” Jonathon looked confused.

     “Did you shave your legs, or your chest? Did you apply any false nails or nail polish?” She asked.

     “I can’t shave my legs or chest.” Jonathon sounded shocked again. “What would a girl say if she saw me with hairless legs?” Jonathon didn’t have more than a hand full of hairs on his chest anyway, so he couldn’t argue that point with her.

     “If you do like dressing as a female every once in a while, and you want to look good when you do, I think it best you come clean with any girl you date. My John found out the hard way what can happen if you keep this sort of thing from your partner.” Joan warned.

     “In what way?” Jonathon asked.

     “He was married once before, and he tried to keep his dressing a secret from her, but she found out about it, and took him to the cleaners.” Joan sounded angry over what the woman had done to her late husband. “He never put up a fight and she agreed to keep his dressing a secret.” She added with venom in her voice.

     “Did you know from the start then, that he liked to wear female clothes?”

     “Yes, but not because he told me.” Joan giggled as she remembered something.

     “So how did you find out?” Jonathon sounded eager to hear this story.

     “I was at some conference to do with law matters when I first met John; he was a solicitor as well.” Joan started to explain. “He was really nice to chat with, and we had a couple of drinks together one lunchtime, but he shied away from wanting to do anything more than have a drink, and I was sad, but let it go.” She added with a sigh.

     “That still doesn’t explain anything.” Jonathon said with a whine in his voice, he wanted to hear the story of how they met and fell in love.

     “I’m getting to that part.” Joan giggled at just how impatient he was. “I’d found out John was stopping in the same hotel as the conference, which I was also stopping in, so I decided after taking a walk one evening that I was going to go up to his room and tell him I liked him.” Joan sounded like she was determined about this as she repeated what happened that night. “I got in the elevator and pushed the button for his floor, but a woman in the lift had already pushed the same button. We both got off on that floor and I ended up following the woman down to John’s room, I thought he was already seeing another woman and was about to walk right past, but something about the woman struck me as being odd, so I asked her for the time.”

     “Was it John...?” Jonathon asked.

     “The minute she turned and looked at me, I knew it was John dressed up right away.” Joan smiled. “He did look good when he was dressed, but I knew it was him by the eyes, He had such amazing eyes.” She added in a dreamy voice.

     “What happened next?” Jonathan asked; eager to find out more.

     “He looked worried, and I just threw my arms around him and started to kiss him.” Joan giggled. “I’m not sure what it was, but he just looked so dam sexy dressed like he was.”

     “How did he react to you kissing him?” Jonathon chuckled.

     “He started kissing me back, and we ended up in his room making love, and I must admit that his first wife was a fool to let him get away.” Joan grinned. “He was such a loving man, and also my best friend when he was Jenny.”

     “Do you miss him a lot?” Jonathon asked.

     “Every second of every day.” Joan admitted. “What about your love life, do you have anyone special in it?” Joan asked, eager to turn things back towards Jonathon.

     “I was seeing a girl called Kirstin, but it ended three months back.” Jonathon said with a heavy sigh.

     “Was that the girl you moved away to be closer to?” Joan remembered Jonathon’s father saying something about his son living with a girl called Kirstin.

     “Yes it was, but she got sick of me trying to pick fights with anyone who commented on my size, and the fact I looked like a girl.” Jonathon admitted. “I was such an idiot.”

     “Did you not try to get her back after she left?”

     “I tried calling her, but I think she had my number blocked, and when I went around to the place I heard she was stopping at, she’d already moved away.”

     “Sounds like you miss her.” Joan sounded sad for Jonathon.

     “I do, and I hate myself for what I did to her, she fell in love with me and I became something she couldn’t even bear to look at.” He admitted. “I don’t blame her for running away from me. I screw up everything; look at what happened between me and my dad.”

     “How do you feel about your size now?” Joan asked.

     “I stopped hanging around with the guys that made me change, and after what I did today, I’m glad that I am the size I am.” Jonathon chuckled at just how silly it had been for him to act all macho. “I think that was one of the reasons I fell out with my dad, apart from the thinking he was cheating on my dead mother.”

     “You blamed him for your size and the way you looked?” Joan looked a little shocked at this.

     “I’m not sure why I blamed him really; I guess it was because I was never taught to do more manly things.” Jonathon shrugged. “I think I was just trying to be something I wasn’t.” He admitted to himself.

     “And you felt like dressing as a woman today was something you want?” Joan pushed for an answer.

     “I don’t want to become a woman, but it was nice to escape from trying to act male for a short time.” Jonathon tried to explain how he felt.

     “So do you want me to help you bring out the inner female?” Joan grinned, she already knew the answer, but she wanted to hear Jonathon say it anyway.

    Jonathon looked to be thinking about it for a couple of minutes before he finally spoke. “I think you’re an amazing woman Joan, and I’m glad that my father had you as a friend, but I feel I should get something straight before we go any further.”

     “And what is that Jonathon?” Joan asked looking a little confused as to where he was going with this conversation.

     “I’d like to have you as a friend, but I could never be anything other than that with you.” Jonathon let out a sigh, glad to finally have that out in the open between them.

     “I don’t look at you in that way.” Joan smiled. “I’m not a cougar.” She giggled. “Think of us as being more like a mother and daughter.” She added once she’d got her giggling under control.

     “I can live with that.” Jonathon agreed. “When do you want to start training me?” He asked.

     “It’s a little late tonight, and we’ve both had a little too much to drink.” Joan said as she picked up her wine glass and finished what was in it. “I think you could do with a trip to a spa as well, so we can let the professionals take care of the hair problem.”

     “A spa...? But won’t they ask too many questions?” Jonathon sounded worried now.

     “I know a little place that caters to men like you that like to get in touch with their feminine side.” Joan smiled. “It’s been some time since I went there myself, so it will be nice to have a relaxing afternoon being pampered.”

    Jonathon wasn’t sure what he was getting himself into, but part of him was excited to see what Joan could do to help him look better when he was dressed as a woman.

     “I do have one request to ask of you.” Jonathon said looking nervous.

     “And what is that?” Joan asked.

     “If you want us to be more like a mother and daughter, then I think you should get to name my female side.” Jonathon laughed nervously as he said it.

     “You’d let me name you?” Joan asked with shock in her voice.

     “Yes, I think it will form a bond between us.” Jonathon smiled.

     “I’ll need a little time to think about this then.” Joan said looking deep in thought.

     “Take all the time you need mother.” Jonathon grinned back at her.

    Jonathon refilled their wine glasses while Joan looked to be thinking about what name to give Jonathon’s female side.

     “I know what your name can be.” She suddenly said looking excited.

     “And...?” Jonathon asked when he saw that Joan wasn’t going to tell him.

     “Candy.” She grinned.

     “Candy...?” Jonathon pulled a face. “You want a daughter with a name that makes her sound like a stripper?” He asked.

     “Don’t you like it?” Joan pouted, but she was soon grinning again, and then it became a giggle. “I’m just teasing you.”

     “Good, because there is no way I’m going to let you call me Candy.” Jonathon said looking relieved.

     “I was going to call our daughter Jessica, so I think your female name will be Jessica.” Joan said looking serious this time.

     “I like that name. “Jonathon smiled. “So my female self will be known as Jessica from now on.”

     “Thank you for letting me name you.” Joan said with tears in her eyes.

     “Did you and John never want to have children of your own?” Jonathon asked.

     “Yes we did, and I was pregnant once, but I had a miscarriage which led to me not being able to have children.” Joan explained.

     “I’m sorry to hear that.” Jonathon said as he reached out and took hold of Joan’s hand.

    They finished off the wine and then Jonathon called a taxi for Joan, and he waved her off at the door, but only after he promised to have lunch with her the next day, so they could do a little window shopping. Jonathon wasn’t sure about letting Joan take him shopping in boy or girl mode, but he did want to start experimenting, and Joan had said he could do with some clothes more suited to a girl his age.

    Joan had taken a look at the clothes Donna had owned, and some of it would be alright for an evening out as Jessica, but she wanted Jonathon to have a natural daytime look as well. Joan planned for Jessica to visit the spa with her, not Jonathon, but Jonathon didn’t know this yet.

 

To Be Continued Next Friday  

 

Story by SaraUK

 

Edited and Posted by SamanthaK

    EDITORS NOTE: Please Comment and/or leave Kudos and let Sara know you like her work please, Any comments on spelling, grammar or the layout of the story please PM me “Samanthak” not Sara. Thank you