© March 2013

Chapter Three: Jessica’s Birth Day

    Jonathon met with Joan the next day for lunch, and he felt nervous about going shopping for female clothing.

     “You don’t need to look so worried Jonathon.” Joan said as they were entering the first of many shops Joan planed to take him in that day.

     “I feel like everyone knows what we’re doing.” He admitted as he looked around expecting someone to start screaming he was looking for girl clothes to wear.

     “Everyone will just feel sorry for you, thinking you’re being dragged around the shops by your mother.” Joan said, waving off his worries. “And they will soon start smiling when you crack open your wallet and start spending money with them.” She added with a grin.

    Joan was right, and they were soon getting lots of help when they started gathering shopping bags. Jonathon was even shocked when Joan told a girl in one shop that they were shopping for him and she just smiled as she started helping them pick out some items.

     “I think you should go and try this skirt on to make sure it fits you alright.” The girl said as she held one skirt up to Jonathon’s waist.

     “Is it okay for me to do that?” He whispered.

     “We have an open policy, and your money is just as good as the next woman.” The girl smiled. “We make most our money from gentlemen like yourself, that is why we have a higher turnover than some of the other shops around here that frown on such things.” She added with a proud smile.

    Jonathon was soon being pushed into a changing room so he could try on the skirt. He was worried about Joan and the shop assistant laughing at him when he was forced to step out and let them take a look at him, but they just started talking to each other, and the girl ran off to get something. Jonathon was glad they had a separate set of changing rooms for him to use, he didn’t know what he would do if he had to get changed and then step out into the main shop for everyone to see.

     “Has she gone to get me a different size, or is she calling for security?” Jonathon asked with a nervous chuckle.

     “Neither.” Joan giggled. “She’s gone to get you a padded panty girdle; we need to see what you will look like with some padding to give you a more feminine shape. I’ve seen more curves on a pencil than you have.” Joan added.

    The girl was soon back with some padded girdles, and he went back into the changing room to take off the skirt so he could put the girdle on. He then slipped the skirt back on and stepped out to see what they thought now.

     “That’s much better, and it makes your waist look smaller as well now you have a little more shape.” Joan grinned with pride. “How does it feel?” She asked.

     “Weird...” Jonathon answered.

     “Apart from weird, how does it feel?” Joan frowned.

     “It feels nice.” Jonathon admitted as he ran his hands over his much more rounded bottom and hips under the skirt.

    Joan smiled once she’d got him to admit he liked the feel of the skirt, and he was soon trying on a number of different styles, some he liked, and some he didn’t like because they were a little tight around the knee. Joan informed him these were called pencil skirts, and a lot of women wore them to the office, and for doing shop work in, which was proved by Judith the shop assistant that was helping them kit Jonathon out with a new wardrobe for Jessica.

    Jonathon was soon being handed a bra and some breast forms to put on, so he could try on some tops. He did as he was told, due to the fact Joan didn’t take any notice of him when he tried to complain, and he was having a lot of fun trying things on. He’d always hated going shopping with Kirstin because he would spend most his time stood with a group of other boyfriends while Kirstin was trying things on, but this was much more fun, and he never realised just how nice some of the fabrics felt to wear.

     “We really need to do something about your legs.” Joan said as Jonathon stood modelling a dark grey pencil skirt and a cream coloured blouse.

     “I thought you said we were going to a spa to get it sorted out?” Jonathon asked as he leaned forward and looked down over his breasts at his feet sticking out the bottom of his skirt.

     “We will, but that won’t be for another week or so.” Joan said looking deep in thought. She soon snapped out of it and carried on talking with Judith about some things she wanted to try.

    Jonathon soon found himself putting on a corset, or as Joan called it, I waist clincher. This really helped to make Jonathon’s waist look slimmer, and the clothes seemed to fit much better after that, so it was added to the buy pile.

    Joan finally called it a day and they went to the check out with Judith, so she could total everything up. Jonathon gasped when he saw the total, but he had the money now, thanks to his father leaving him a small fortune. Jonathon didn’t think he’d have it long if he kept spending it like this. They thanked Judith for all her help, and she said to ask for her whenever they went in the shop again.

     “We better take all this back to the car.” Joan said after they left the shop.

     “You plan to do more shopping?” Jonathon asked.

     “Not shopping, but we do need to make one more stop before we leave the town and head back to your place.” Joan smiled as she started walking back towards the car without filling Jonathon in on any more details.

    Jonathon had a feeling she was up to something, but she wasn’t about to spoil the surprise, so he caught up to her and they walked quietly back to the car.

     “You can’t be serious...!” Jonathon said as he stood outside a salon looking at a sign that said they did full body waxing. “They’ll laugh me out of the shop.” He added as he turned around and went to walk away again.

     “They get men in there all the time having their bodies waxed.” Joan said as she grabbed his arm and stopped him dead in his tracks.

    Jonathon went to argue she was just saying that when the salon door opened and two large looking guys walked out the place. Both of the guys looked like they spent most their time in the gym, and just one of their arms had more muscle that Jonathon had on his whole body.

     “Excuse me...!” Joan said to the men. “Have you just been in there getting a wax?”

     “What are you doing...?” Jonathon asked in an angry whisper.

     “Yep, we sure have.” One of the men said, not looking bothered he’d just been asked such a personal question. “Best place around, and they don’t charge you the earth either.” The man added.

     “See, I told you.” Joan said turning to look at Jonathon.

    Jonathon wanted a worm hole to open up and swallow him as he found Joan and the two large men all stood looking at him now.

     “Don’t look so worried man; the chicks love a smooth bod.” The other man said as he flexed his pecks at him while grinning.

    Jonathon just gave the man a weird smile before he let Joan drag him into the salon. Jonathon was just glad to be away from the two men that he didn’t argue with the fact he was now inside the salon.

     “Is this going to hurt?” He asked Joan in a whisper while they were waiting to be served.

     “Yes, but only to begin with, then you kind of get use to the pain.” Joan admitted.

     “Are you sure I can’t just shave my legs?” He asked like a whiney teenager.

     “No, this will give you a much better result, and if you come on a regular basis you will end up with much finer hair growing, so it will make looking feminine more easy for you.” Joan explained.

    Before Jonathon had time to argue with her, they were approached by a woman, and Joan was soon explaining what she wanted done to Jonathon, and he found himself being taken through the shop and into a back room.

    Joan had been right about it hurting, and the fact that after a short time it was just a dull pain he felt. It did make him want to scream out when the woman did some spots, especially when she got close to his groin. He was shocked when the woman asked him to lie on his belly and she then waxed his butt crack for him. He never realised he had hair around that area.

    Jonathon was glad when the woman said she was done and he could get dressed again. This is when he realised the different he felt now he had no hairs on his legs. The jeans he was wearing felt much rougher now.

     “That wasn’t too bad was it?” Joan asked when he walked up to her in the waiting area.

     “No, but it sure felt weird.” Jonathon admitted. “I guess I better go and pay for this torture.” He added as he pulled his wallet out his pocket.

     “No need, I’ve already paid.” Joan said as she put the magazine down and got up so they could leave.

     “How much was it? I’ll pay you back.” Jonathon said as he opened his wallet.

     “This was my treat for being such a good sport this afternoon and making me want to laugh again.” Joan grinned as she left the shop with Jonathon following close behind. “I’ve not had this much fun since before John died.” She admitted with a giggle.

    Jonathon found himself smiling, because he’d not had as much fun since before Kirstin walked out on him. He did find the fact his legs were now hairless a little strange, but also quite nice at the same time. He wondered what it would feel like to have pantyhose wrapped around them now.

    They made it back to the car and were soon on their way back to Jonathon’s. He was grateful for this, as he’d been worried Joan might take him some place to get his ears pierced, or something just as crazy, but they were soon parking up on the driveway outside his parent’s home.

     “Would you like a coffee?” Jonathon asked once they had all the bags in the house and they were both sat in the living room.

     “That sounds like a wonderful idea.” Joan said looking tired.

    Jonathon was soon returning to the living room with two mugs of coffee for them both, he handed Joan one and then sat down again with his own.

     “I can’t believe how much I spent this afternoon.” Jonathon said as he looked at all the shopping bags.

     “You did spend quite a bit of money, but you also needed a lot of things if you want to pull off being Jessica in the daytime.” Joan said just before taking a sip of her coffee.

     “Daytime...?” Jonathon said when he realised what Joan had just said. “What do you mean? I don’t plan to go out in the day or night time.”

     “Then why did you buy all these things?” Joan asked just before hiding her smirk by taking another sip from her mug. Joan already knew that Jonathon would want to go out and let the world see Jessica once he was fully dressed. She’d seen the same look in her husband’s eyes many a time.

     “I don’t know why I bought it all; I guess I just got lost in the moment.” Jonathon shrugged when he realised he didn’t know why he spent so much money to just wear it around the house.

     “I’d like to meet my new daughter.” Joan hinted, in the hopes Jonathon would get changed and show off his newly discovered feminine side.

    Jonathon looked nervous all of a sudden and he didn’t say anything right away, but he finally met Joan’s eyes and spoke. “Would you help me bring her out?” He asked looking hopeful.

     “I wouldn’t be much of a mother if I didn’t help my daughter.” Joan replied as she placed her mug down on the coffee table and then got to her feet.

    Jonathon did the same and then the two of them collected all the shopping bags and took them up to his parents’ bedroom so they could bring out Jessica.

     “The first thing we need to do is apply the breast forms.” Joan said once they were stood in the bedroom.

     “Apply them...?” Jonathon asked nervously. “I thought I’d just place them in the bra once I had it on?”

     “They tend to move around a little too much, and you risk them falling out when you bend over.” Joan explained.

     “I will be able to remove them again though won’t I?” Jonathon looked worried.

     “Yes, they will peal right back off again.” Joan giggled at the worried look on Jonathon’s face. “We’re only using these sticky pads.” Joan explained as she showed Jonathon the pads that would go on the inside of the breast forms and help stop them moving around inside his bra cups.

    Jonathon was soon letting Joan help him attach the breast forms to his now smooth chest. He kept hold of them like they might fall off if he let go, but he was soon removing his hands and found it odd to feel the extra weight on his chest.

     “Are you sure I’ll be able to remove them again?” He asked when the breast forms didn’t fall off his chest like he thought they might.

     “Yes they will peel off again, but you do need to be careful when you do it.” Joan warned. “John used to get in the shower to take his forms off, he use to say the warm water helped to loosen the stickiness of the pads.” She explained.

     “This feels really weird.” Jonathon said as he bounced his chest around and watched his new breasts moving around all over the place like they had a mind of their own. “How do you get use to having these things stuck to your chest all the time?” He asked as he jiggled his chest around some more.

     “You don’t just wake up one morning and find them this size.” Joan giggled as she watched him dancing around and making his breasts jiggle. “It happens over the course of a few years, and I just learned to live with them being there.” She tried to explain, but it wasn’t something she’d ever really thought about until now.

     “Do you think I’ll ever get used to them?” He asked while still looking down and watching his breasts jiggle.

     “That depends on if you’re planning to keep them?” Joan asked with a raised eyebrow.

     “No...!” Jonathon said suddenly. “But they do feel kind of nice tugging on my chest like they are.” He added with a shy smile.

     “Get this bra on; unless you would rather me just find you a set of tassels to stick on the end of them for you.” Joan giggled as she handed Jonathon a bra to trap his new playthings in.

    Jonathon giggled as he took the bra off Joan and then he placed it around his waist back to front and clipped it together, just like he’d seen Kirstin do many times while they lived together. He did find it a little harder to do this time, due to him now having the breast forms stuck to his chest and he was trying to look past them.

     “Where did you learn that little trick?” Joan asked as she watched him fasten the bra on back to front before he twisted it around and then seated his new breast in the cups as he pulled the straps up over his shoulders.

     “I’ve seen Kirstin do it.” He said while he played around with his new chest, making sure it looked okay.

     “Most men try to put the thing on and then clip it closed around their back.” Joan smiled. “John use to struggle and do it that way until I showed him the way you just used.”

     “I’d still be trying to put the bra on from yesterday if I tried to put it on that way.” Jonathon admitted.

    Joan giggled at Jonathon’s honesty, then she handed him some panties and the padded girdle. “Go to the bathroom and put these on.”

    Jonathon did as he was told, but felt a little strange as his breasts bounced with every step he took towards the bathroom. Having the breast forms attached to his chest felt very different to the day before.

    Once in the bathroom he stripped off his shoes, socks, trousers and underwear before he picked up the panties and stepped into them, he tucked his manhood away between his legs and then he picked up the padded girdle and stepped into that before pulling it up his legs and into place. He was feeling less and less like a man and more and more like a woman now he had larger hips and a set of breasts.

     “I hope I don’t need to make a quick trip to the bathroom in all this.” Jonathon said when he returned to the bedroom.

     “There is no such thing as a quick trip to the bathroom for any lady, and even less for a lady like you.” Joan smiled. “Jenny and Donna would be gone half the night when they finally did need to go.” She added with a roll of her eyes.

     “What do you want me to put on next mother?” Jonathon asked, trying to sound more like a female, so he kept his voice soft and just above a whisper.

     “That sounded pretty good.” Joan grinned as she picked up a pack of black pantyhose and handed them to him. “Jenny bought some CD’s on how to make your voice sound more feminine, I’ll have to see if I can find them for you.”

    Jonathon opened the packet and then sat on the edge of the bed to put them on. He was soon being told how to do it properly, so he wouldn’t ladder them.

     “Why do these tights feel so much better than the ones I wore yesterday?” Jonathon asked as he ran his hands up and down his nylon covered legs.

     “That will be the waxing.” Joan pointed out. “You don’t have any leg hair to mask the soft feeling of the nylon.” She smiled. “I also see that you inherited your Aunt’s legs.” Joan pouted.

     “What do you mean?” Jonathon asked looking confused.

     “Your aunt Donna had amazing legs, just like you do.” Joan frowned at the fact she needed to explain it to him.

     “I always thought they were a little thin and lacked any muscle.” Jonathon said as he looked at his legs now wrapped in the black pantyhose.

     “Your lack of muscle is what makes them look so stunning now.” Joan said sounding jealous. “I think you will make quite the pretty young woman when we’re done with you.” She added with a smile.

    Jonathon just blushed, not knowing how to respond to that complement. “What do I put on next?” He finally said, trying to get them back on track with bringing out Jessica.

     “You will need this.” Joan said as she handed him a silk robe to put on.

     “Am I not going to try on one of the new dresses or skirts I bought?” He asked sounding disappointed.

     “Yes later, but we need to do your makeup, and I don’t want to risk getting any of it on your new clothes.” Joan said in a scolding tone as she pulled Jonathon to his feet and then helped him to put the robe on. Joan then tied the belt around his waist and he looked like a woman from the neck down, something he couldn’t help grinning about.

     “Wow, I see what you mean about my legs.” He said as he checked himself out in the mirror.

     “Are you trying to upset me...?” Joan asked as she stood frowning at him with her hands on her hips trying to look angry.

     “Sorry mummy.” Jonathon pouted as he battered his eyelids at her.

     “Just get over here and take a seat missy.” Joan giggled as she pulled out the chair at the dressing table and turned it around so she could do his makeup for him.

     “Do you not what me to do my own makeup?” He asked.

     “You will have plenty of time to practice, and I will help you, but tonight I want to let you see just how good you can look as a woman.” Joan said as she set to work on hiding his eyebrows using the same glue stick method he’d used the day before.

     “Did you used to do Jenny and Donna’s makeup for them?” Jonathon asked as he let Joan work on his face.

     “Yes, and I taught them both how to do different looks, but neither of them had skin like you do, and these eyelashes are wasted on a man.” Joan said sounding jealous again.

     “It’s a good job that I won’t be a man in a minute then.” Jonathon smiled.

     “You’re enjoying all this aren’t you?” Joan smiled.

     “Yes I am to be honest with you.” Jonathon admitted. “Does that make me weird?” He asked sounding worried.

     “Some would say yes, but I just think it’s a way to relax and do something different with your time.” Joan gave her honest answer. “I think accepting your feminine side will help you to grow as a person.” She added as she worked on his lips.

     “I wonder what Kirstin would say if she could see me now.” Jonathon laughed.

     “She wouldn’t be able to call you a sexist pig, that’s for sure.” Joan giggled.

     “I came to realise over the last three months that I was just trying to be something I wasn’t because I didn’t want anyone to see my softer side.” Jonathon admitted. “It’s just a shame it took me losing Kirstin to realise that, and the death of my father.” He added with a sigh.

     “I think your father would be proud to see you now.” Joan smiled.

     “That’s a weird thing to say to a guy that’s letting a beautiful woman turn him into her daughter for the evening.” Jonathon smiled back.

     “I’m not beautiful.” Joan said, waving off Jonathon’s compliment.

     “Have you looked in a mirror lately?” Jonathon asked with shock in his voice. “If I was a little older, and not dressed as a woman, I’d be asking you out on a date.” He admitted.

     “And I’d say yes to you, but I like the idea of having you as a daughter, and an adopted son, so we will stick to being really good friends.” Joan said with a tear in her eye. “I also had too much respect for your father to get up to anything with his son.”

    Jonathon let Joan finish his makeup, and then she put a wig cap on him and got the wig out that he’d worn the day before and fitted it to his head before she started brushing it into shape.

     “Can I take a look now?” He asked when he thought she’d finished.

     “I’d like you to wait until I’ve finished, so you can get a look at the finished article.” Joan said as she stepped behind him and covered up the mirror. She’d already turned the floor length mirror around so he couldn’t see himself in that one.

     “Okay, do your worst.” Jonathon smiled up at her.

    Joan smiled back as she helped him to his feet and then helped him to remove the silk robe. She then handed him the waist clincher to put on. Once that was in place, Joan took one of his father’s evening dresses off its hanger and handed it over to him to put on.

     “I spend all that money, and you want me to wear one of my father’s dresses.” Jonathon said, and then looked confused just before he giggled. “I never thought I’d be saying those words.” He added with more giggles.

     “I just want you to look extra special tonight, and all the clothes we bought today look fine for every day looks, but not for an evening meal.” Joan explained as she helped Jonathon to step into the dress and pull it up over his much curvier body, thanks to all the padding.

    The dress was black with a flared skirt which he later found out was called a cocktail dress. The dress had short puffy sleeves and a round neck, so he didn’t have to worry about anyone seeing that his breast weren’t real. Joan pulled up the zipper, sealing him inside the dress until she decided to release him, unless he wanted to struggle with the zip on his own, not that he was in any rush to take it off.

     “Now can I look?” He asked with a pleading in his voice.

     “Not yet.” Joan said in mock annoyance as she lightly slapped his arm. “We need to get your shoes on, and I also want to do your nails.” She added as she walked across to the collection of shopping bags with all their purchases in and pulled out a shoe box.

    Jonathon was soon looking at the open box and saw that he would be wearing a pair of black sandals with lots of little fake diamonds stuck to the straps that wound their way all over the toe and ankle area. The sandals only had a two inch heel, so Jonathon was able to walk in them without any trouble.

     “These are much easier to walk in than the ones I was wearing yesterday.” Jonathon admitted as he walked up and down the bedroom with a grin on his face as he felt the dresses fabric brush against his nylon covered legs.

     “Given time you will become an expert at walking in all of Donna’s heels, but I think this is a much better height for you to begin with.” Joan beamed as she saw how much he was enjoying himself. “Come and take a seat, so I can do your nails for you.” Joan added as she patted the seat at the dressing table. Joan had pulled up a small stool and was all ready to start applying fake nails to his short chewed ones.

    Jonathon walked over and sat down on the offered seat. Joan smiled when she saw how he brushed the skirt of the dress under himself as he sat down.

     “Did I do something wrong?” Jonathon asked looking worried when he saw Joan smile.

     “No far from it.” Joan started to explain. “You just looked so natural when you sat down; you even remembered to brush your skirt under yourself to stop it getting crinkled up.”

     “I’ve seen other women do it when they sit down, so I just did the same.” Jonathon shrugged; he’d not really been thinking about what he did, it just felt like the right thing to do at the time.

    Joan couldn’t help realising that Jonathon looked more relaxed and even happier to be dressed as a woman, and he seemed so natural in the part. All his movements that looked odd for a man to do, looked natural now he was dressed as Jessica. Joan didn’t want to worry him, so she decided to keep her thoughts to herself for the time being, and just let him enjoy his first time as a woman.

    Jonathon sat and watched Joan work on his nails, so he could have a go himself at some point in the future. He’d not been able to watch her do his makeup, but this was something he could watch her do to him, and he was amazed as he saw his normal male looking hands slowly vanish with each false nail Joan applied. He was soon sporting two sets of pale pink claws, or they looked and felt like claws to Jonathon.

     “How am I supposed to pick anything up with these things stuck to my hands?” Jonathon asked as he wiggled his clawed fingers around.

     “They’re not that much longer, you’re just not used to them yet.” Joan said as she waved off Jonathon’s complaints. “Give it a little time and you won’t even notice them, but I guarantee you will miss them when they’re gone again.” She added looking smug.

    Jonathon just gave her a doubting look as he started experimenting with picking things up on the dressing table. He did like the way his hands looked more feminine now he had long pale pink nails. He was snapped out of his thoughts when he heard Joan speaking to him.

     “So are you ready to take a look at Jessica then?”

     “Yes please mummy.” Jonathon said sounding more like a little girl than a grown woman.

    Joan giggled as she helped him up and stood him in front of the floor length mirror before she walked over and turned it around. Jonathon still couldn’t see anything though because Joan had covered it with a blanket.

     “Jonathon, I’d like you to meet my daughter, Jessica.” Joan said as she pulled off the blanket.

    Jonathon’s mouth fell open in shock, and the girl in the mirror did the same. He lifted his left arm, and the girl in the mirror did the same. “Is that really me?” Jonathon asked as he lifted a hand to his feminine looking face, which was now framed by blonde curls from the wig he was wearing. He looked at the hand in the mirror that was now touching his cheek, but it looked more like the hand of a woman, he thought everything about the girl in the mirror screamed woman. “She’s beautiful, I mean I’m beautiful.” He corrected himself and saw the girl in the mirror speak at the same time.

     “I never expected my daughter to be anything but beautiful.” Joan grinned as she stepped over and wrapped an arm around his much thinner looking waist.

     “Thank you mother.” Jonathon said as he turned to look at Joan just before he threw his arms around her so he could give her a hug.

     “You’re most welcome sweetie.” Joan said as she hugged her new daughter back. “I feel a little under dressed now myself, so if it’s alright with you, I’m going to borrow one of Donna’s dresses for the evening.” Joan asked once they had broken the hug.

     “Please feel free to borrow whatever you want mother.” Jonathon said in his best version of a female voice. He knew he needed to work on it, but it still sounded much better than his normal male voice, which really wouldn’t suit the way he looked at the minute.

    Jonathon couldn’t stop looking at his new female self, so he didn’t take any notice of the fact Joan had stripped out of her skirt and blouse, and was now slipping into another one of Donna’s cocktail dresses. Jonathon didn’t notice anything until he saw Joan come and stand next to him, then he was left looking at two beautiful women in the mirror.

     “Wow, Joan, you look amazing.” Jonathon said.

     “It’s mother to you while you’re dressed like that.” Joan scolded him in a playful way.

     “Sorry mother.” Jonathon giggled, sounding just like a girl again.

     “That’s much better.” Joan smiled. “Shall we head out for a spot of dinner then?” Joan asked with a grin.

     “Go out...!” Jonathon shouted, “With me dressed like this...?” He asked in a much softer tone, but still looking just as worried.

     “Yes, you look more than passable, and it would be a shame to not let the world meet my daughter.” Joan said in a matter of fact way.

     “I’m not sure I’m ready to go out just yet.” Jonathon said as he looked at himself in the mirror again, but in a more critical way this time.

     “Your first trip out is always going to be the scariest one Jessica, so let’s just get it out the way, and you will see that no one will see you as anything but a beautiful young woman out with her mother for an evening meal.” Joan said in a soothing tone that did make Jonathon feel a little better. “If we have any trouble, I promise to bring you straight home again, and I’ll never ask you to set foot out the house as Jessica again.”

    Jonathon kept looking at the girl in the mirror, and he couldn’t see any sign of that girl being a man underneath, so with a sigh he agreed to give it a try. He watched as Joan excitedly ran around the room sorting him out with a coat and a purse, which she told him to place his wallet in, and she added some makeup for any powder room breaks they needed to take later in the night.

     “I can’t go to the restroom while I’m out.” Jonathon argued. “What will all the other guys say when they see me enter the room?” He asked as he waved his hands up and down his female looking body.

     “I think you have the wrong room Miss?” Joan smirked.

    Jonathon went to say something else, but he ended up smirking back at her. “You’re loving this aren’t you?” He finally asked with his hands on his hips, he’d tried folding his arms across his chest, but couldn’t with his new breasts getting in the way.

     “Just a little bit.” Joan grinned as she held up her hand with her finger and thumb an inch apart. “I’m willing to make a bet with you.” Joan added.

     “What kind of bet...?” Jonathon asked looking suspicious of what her bet might be.

     “If you get through the dinner and I deliver you back here without anyone realising you’re not a woman called Jessica, then you have to come away for a weekend as Jessica. No male clothes at all, just a mother and daughter trip away.” Joan explained, making sure Jonathon understood that it wasn’t a trick for her to get him in a room alone.

    Jonathon looked in the mirror again, and he had a feeling he had already lost this bet, but part of him wanted to spend the weekend pretending to be this woman he was looking at in the mirror, so he was actually hoping he didn’t get noticed. “It’s a deal...!” He said as he held out his hand to shake on it.

    Joan took hold of his hand and then pulled him into a hug. “Woman don’t shake hands to seal a deal, we hug.” Joan lied, she just wanted to hug her new daughter, because she also knew he was about to lose this bet.

Chapter Four: Jessica’s First Meal

    The two of them had gone in Joan’s car to a small restaurant she knew they could have a quiet meal without any trouble. This still didn’t stop Joan having trouble getting Jessica out of the house and into her car. Joan had even more trouble once they were in the restaurant car park.

     “You’ll be just fine Jessica.” Joan said as she took hold of Jonathon’s shaking hand.

     “I’m not sure I’ll be able to keep anything down if I do go in there.” Jonathon argued.

     “Well I’m hungry, and I’m going in to have some dinner.” Joan said sounding more like a parent now as she let go of Jonathon’s hand and she got out the car. Joan then walked around to Jonathon’s side of the car and opened the door before leaning down to speak again. “Are you coming in, or waiting out here in the car, all on your own.” Joan made the last part sound creepy.

    Jonathon looked around like there were people just waiting for Joan to move away so they could attack him, so he let out a sigh and undid his seatbelt and got out of the car. Joan was smirking as she watched how natural he made it look as he spun his legs around and then he rose with feminine grace, brushing out the skirt of his dress after placing his purse over his shoulder.

     “Shall we go eat then mother?” Jonathon asked, sounding more like a Jessica than a Jonathon.

     “I thought you’d never ask Jessica.” Joan grinned as she linked her arm through Jonathon’s and started leading her new daughter into the restaurant.

     “Good evening ladies.” A man in a suit asked as they entered the restaurant. “Table for two...?” He asked with a smile as he looked the two of them up and down.

    Jonathon gripped Joan’s arm a little tighter, but soon relaxed when he saw that the man showed no signs of realising that one of the women he was checking out wasn’t really a woman.

     “Yes please, a table for two.” Joan answered with a smile.

     “Follow me right this way.” The man smiled back as he led the way to a table set for two.

     “Thank you.” Jonathon said quietly as the man helped him with his seat. Jonathon was careful to keep his voice soft, so as not to give himself away; it must have worked because the man seamed to smile even more as he looked Jonathan in the eyes.

     “Can I get you both a drink while you look through the menus?” The man asked as he ran around the table to help Joan with her seat.

     “We’ll just have two glasses of sparkling water please, I’m driving, and my daughter doesn’t drink.” Joan informed the man.

    The man nodded and then turned to a waiter that had appeared, and he told him to go and get them their drinks before he himself went to sort out another couple that had entered the restaurant.

     “I don’t drink...?” Jonathon asked in a whisper, but still keeping his voice soft and feminine.

     “You’re welcome to start sweetie, but if you start drinking alcohol, then you will need to go to the restroom that much sooner.” Joan pointed out in a mother knows best tone of voice.

     “Oh... Good point.” Jonathon agreed as he realised he didn’t want to use the restroom here and have to practically undress himself to go.

     “I’m also sure you don’t want to get drunk and lose your focus either.” Joan smirked. “I’d hate to see you win our little bet, just because I got you drunk.” She added with a pout.

    Jonathon thought that was another good reason, but only because he didn’t want anyone to know he wasn’t really a pretty young woman out with her mother for a nice dinner. So not having an answer to what Joan had just said, he started looking at the menu. Jonathon had to hold the menu up to his face to hide a giggle when he saw some man at a nearby table get kicked by his date. The man had been looking him up and down rather than listening to what his date was saying.

     “What’s got you giggling?” Joan asked with a grin.

     “I think I just got some man in trouble.” Jonathon whispered as she looked over at the table where the man was now rubbing his shin and looking daggers at his date.

    Joan’s grin got even bigger as she looked at the couple on the other table and then looked back at Jonathon as if to say ‘I’ve already won this bet’. Jonathon knew what she was grinning for, and he felt glad that he would be losing his bet with her.

    The waiter returned with their drinks, and they placed their orders, Jonathon wasn’t the world’s biggest eater, so it didn’t look odd for him to order the same as Joan.

     “How do you feel Jessica?” Joan asked once they were enjoying a prawn cocktail for their starter.

     “It’s kind of scary, but exciting at the same time.” Jonathon giggled as he looked around the room at all the other people eating. He found himself wondering if there was anyone else in the restaurant pretending to be something they weren’t.

    Joan was glad Jonathon was enjoying himself, and he did start to relax into the part little by little, and by the end of the meal he was totally at home being Jessica, as he spoke with Joan about the things they had bought that day, and about some of the things he would like to get in the future, now he’d been out.

     “Would you like to come out shopping with me again soon then Jessica?” Joan asked with a look in her eyes that said she wanted Jonathon to dress as Jessica to go shopping.

     “I think I would enjoy that, but wouldn’t I get in trouble if they find out?” Jonathon asked.

     “Who are they...?” Joan whispered back like someone might be listening in on their conversation.

     “The people who own the shops.” Jonathon said in an angry whisper.

     “I doubt any of the people working in the shops would even realise you’re not what you appear to be.” Joan said waving off Jonathon’s worries. “No one here has jumped up screaming anything, and you’ve had more than a couple of men checking you out, I’ve even noticed a couple of woman giving you the once over.” Joan smirked.

     “I’m sure they’d be disappointed if they saw me naked.” Jonathon shrugged.

     “Who, the men or the women?” Joan smirked some more when she saw the look Jonathon was giving her.

     “The women...” Jonathon finally got out when his mouth started working again. “A man is never going to see me naked.” He added in a whisper.

    Joan just took a sip of her sparkling water to hide the grin she had on her face over Jonathon’s shocked look and blunt answer.

     “What are you doing?” Joan asked when the waiter brought the bill over and Jonathon picked it up just before she was able to.

     “I’m paying for the meal.” Jonathon said in a tone that let Joan know he wouldn’t be argued with.

     “I really think you should let me pay.” Joan said. “That is unless you have enough cash on you, or you’re not bothered about them seeing the name on your credit card.” She added with a grin as she looked Jonathon up and down to make her point.

    Jonathon looked down and saw his chest stuck out, and his long slender fingers with the pale pink nails holding the bill for their dinner, and he realised that all his cards and ID had Jonathon on them, and he already knew he didn’t have enough cash on him to pay for the meal.

     “Point Taken, but I will find a way to pay for our meals in the future.” Jonathon warned as he handed her the bill to pay.

     “Does this mean I’ll be getting treated to a night out again then by my daughter?” Joan smirked excitedly.

     “I hope so.” Jonathon smirked back.

    Joan paid the bill and they left the restaurant and walked back to the car. Joan noticed that Jonathon looked a little sad about something. “What’s wrong Jessica? You sad you lost our bet?” She asked before pulling away from the car park.

     “No, far from it. I’m sad that it’s all over.” Jonathon admitted. “I wish we could go someplace else, so we can just walk around and keep pretending that I’m your daughter.” He added with a pleading in his voice.

     “I do have one idea, but you may find it a little boring.” Joan said looking hopeful.

     “What is it?” Jonathon asked sounding eager to do anything that kept them out doing things while he pretended to be Joan’s daughter.

     “Jenny and I use to visit a local art gallery that is open late.” She started to explain. “I’ve not been since John died, and I’m sure you would enjoy some of the artwork.”

     “That sounds like a wonderful idea mummy.” Jonathon said sounding more like a young teenage girl, more than a young woman in her twenties, or even a young man in his twenties.

    Joan seemed to perk up as well, and she was soon pointing the car in the direction of the city and the art gallery.

    Joan didn’t have any trouble getting Jonathon out the car when she parked just down the road from the art Gallery, and Jonathon was eager to link arms with his new mother and let her lead him up to the gallery doors where a man just entering the gallery quickly ran past the two of them and held the door for them.

     “Ladies...” The man smiled as he looked the two of them up and down as they walked past him and into the gallery.

     “Thank you.” Joan smiled.

    Jonathon just smiled and nodded to him, not wanting to give the man any reason to speak to him. Jonathon was glad to see the man had more interest in Joan than him, but the man was much older than Jonathon, so it stood to reason he’d show more interest in Joan.

    Joan was soon guiding Jonathon around the gallery and telling him about the pictures she liked the most, and which Jenny had liked to come and look at. Jonathon had never done anything like this before, mainly because it wasn’t a manly thing to do, but he’d come to realise that he wasn’t a manly man, or even a man at the minute, but he was enjoying the feel of the clothes and the company.

     “Thank you for a lovely evening, mother.” Jonathon said in his feminine voice once they were back in the car. “I can’t remember ever having such a wonderful evening.” He admitted.

     “I’m glad you had such a wonderful time, and it was nice having you play my daughter.” Joan smiled back at him. “I must admit you did seem to be very natural in the role.”

     “Have you ever realised that you’ve been fooling yourself?” Jonathon asked. “I mean like you’ve been lying to yourself about who you are.” He added looking confused.

     “Do you think you should have been born a female?” Joan asked, thinking she understood where this conversation was going.

     “No, I don’t want to have anything cut off.” Jonathon said with a shudder. “I just think I spent all my time trying to deny that I have a feminine side in me that’s been fighting to get out.” He added with a sigh.

     “There is nothing wrong with wanting to dress as a woman, and there is most definitely nothing wrong with having a softer male side.” Joan said.

     “I can see that now, and I wish I’d seen it before I lost Kirstin, but I’m not sure how she’d have taken me being dressed like this.” Jonathon giggled as he looked at his nylon covered legs stuck out from under his dress, and his long pink nails.

     “I’m sure you’ll find love again one day, but just remember to be honest with the woman when you find her, and you know she’s the one you’d like to spend the rest of your life with.”

     “I hope she’s like you and my other mother.” Jonathon said with pride in his voice.

     “You could be asking a lot there daughter.” Joan grinned, which let Jonathon know that she was just teasing him.

    Joan finally got Jonathon back to his parent’s home and she offered to go in with him and help to take the makeup and clothes off, but he said he could cope. He did get Joan to pull the zip down on the back of the dress to save him some time once he was in the house.

     “I’ll see you tomorrow when I come over to pick you up and take you to see your father.” Joan said looking a little sad for Jonathon now. She would be happier for him when the funeral was out the way and Jonathon could start to move on with his life.

     “Okay mum.” Jonathon smiled, still maintaining his female voice and mannerisms as he got out the car. “Thanks again for a wonderful evening.” He added as he leaned back into the car and gave Joan a hug and a kiss on the cheek. Joan returned the hug and then she waited for him to enter the house before she drove away.

    Jonathon wasn’t tired when he got in the house, and he wasn’t ready to take off any of the makeup, wig or false nails, so he went up to his room and changed into a simple top and skirt before going down to the kitchen and pitting the kettle on to make a drink. While the kettle was boiling he went into the study and fired up the computer and logged onto the net using Donna’s details.

    By the time he got back to the computer, he was already being asked to chat by the same two girls’ from Canada. They asked him how he was doing, and he decided to come clean and tell them both about his last couple of days.

    He was soon getting out his father’s camera and taking some photos, due to the two girls not believing him, and even when they saw the photos they thought he was just teasing them, so he ended up firing up the web cam and having a live chat with them.

    Both girls finally believed him, and they both said they were really jealous because he could pass so easily, but they had been just as jealous of Donna as well for the same reason.

    The sun was coming up when Jonathon finally called it a day and logged off, after promising to email his two new friends, but not before he opened up an email account for Jessica. He still had to remove all the makeup and wig, but he decided to leave the nails on and worry about them the next day, or later that day when he woke, mainly because he couldn’t find anything to remove the nails with, and he didn’t want to call Joan at just after five in the morning.

    Jonathon finally got into bed after looking through Donna’s things and finding a pair of pink silk pyjamas and putting them on. He found himself feeling nervous, he wasn’t sure how he would feel when he saw the body of his father laying in a coffin, but he knew it was something her needed to do, and he was glad that Joan had agreed to go with him. Jonathon just wished his father could have met Jessica, and Jessica had gotten to meet Donna.

    He soon found sleep though, even with all the worrying, and he found himself dreaming of going shopping with Donna and Joan.

 

To Be Continued Next Tuesday  

 

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